Fun Friday: Startup Creation Stories

I absolutely love Paul Graham's story of how Y Combinator started. It has all the makings of a great startup story. Paul and Jessica came up with the idea on the way home from dinner walking through Cambridge. The sand in the oyster was the fact that Jessica hated her job.

It made me think we should share startup creation stories today on fun friday. I will start with mine.

It was 1996, I was restless in my job as a Partner at Euclid (do all startup stories start with a job thing?). My friend Mark Pincus said "you should start a venture capital firm." I said, "I'd like to do that but who would be my partner?" Mark said "Jerry Colonna of course."

So I reached out to Jerry. We arranged a dinner for us and our wives. I left the Gotham Gal inside with Jerry and Barbara while I was on the phone helping with the negotiation of the sale of Mark and Sunil's first company Freeloader. It was rude, but what was I going to do? That was a big deal for me. Fortunately the Gotham Gal closed the deal with Jerry for me.

On the way home across the Throgs Neck Bridge, I asked the Gotham Gal what I should do. She said "go for it." And so we did.

That's the creation story of Flatiron Partners.

Do you have a fun startup creation story? If so, please share it with us in the comments.

#Random Posts

Comments (Archived):

  1. Alexander Close

    A friend and I with culinary backgrounds started throwing household dinner parties in university.  First with friends, then friends of friends.  They got pretty big, they got pretty outta hand.  Random people started showing up.  The more random and eclectic they became, the more fun they ended up being.  We finished school and thought, can we keep doing this as an advertising service for restaurants?  Enter thesocialfeed.We’ve got a long way to go, and a lot more to figure out, but we did get in the local paper yesterday. :)…

    1. fredwilson

      “they got pretty out of hand”now that’s how you know you’ve got something good!!”well played” as JLM would say

      1. AP

        Was fed up of Investment Banking (healthcare) in NYC. Transitioned (sort of) to work for a high-end VC on Sand Hill Road. Wanted to explore healthcare services in developing countries. Worked for the vc as their India healthcare transactions guy. Discovered that big (huge) mismatch in healthcare investing opportunities in India and the money chasing healthcare. The real opportunity in healthcare not growth equity as is commonly understood but to have a point of view on how healthcare should develop in india and incubating companies to do just that. Moved to india and doing just that.Changed from banking to investing to entrepreneurship.   Currently (almost) closed my first seed round and incubating my first companyand loving every moment of it. Yes Fred,   

        1. AP

           Yes, Fred, I do believe (with no empirical evidence) that being in a job that one does not like can morph into entrepreneurship…

        2. Prashanth P

          Hi,I’m looking for some VC funding in health-care space in India. Would love to chat with you and possible mentorship :-)Thanks !

  2. jason wright

    “Flatiron” – how did that choice come to be?

    1. fredwilson

      i’ve always been obsessed about that building and that neighborhood. our first apartment in NYC was a few blocks north of madison square park. i wanted to move down there (we started the firm in midtown) and name the firm after the building. the owner of the building sued us for copyright infringement. we settled. we paid them something for the rights to the name and the logo.



        1. fredwilson

          right. i stand corrected. it was a trademark suit

  3. Carl Rahn Griffith

    That’s a cool story :-)In the middle of one right now…I had been working on and off with some lovely folk in Vienna, over a number of years (a decade plus, thinking about it) and a while ago, in the beer garden of a favourite London pub (naturally, lol) – ‘The Atlas’ (Earls Court area) – we were discussing how we’d like to do things better in the future; focused on strong ethics and emerging markets – and very importantly also have some fun.And so, here we are – web site only went live yesterday, so please bear with us – we are also on Twitter and Facebook. If you are interested, and want to learn more, please see – Fingers crossed!

    1. Emily Merkle

      Sweet – I developed an operating philosophy that is so integral to our every move it truly simplifies things – that and an ethical approach slays our competition.Woukd you be interested in swapping credos?

      1. Carl Rahn Griffith

        Cool. Sure thing – drop me an email sometime – carl(at)egoboss(dot)com or carl(at)ropeventures(dot)com

    2. RichardF

       good fortune Carl

      1. Carl Rahn Griffith

        Thanks, Richard. Ditto!

    3. awaldstein

      Good luck with this Carl.

      1. Carl Rahn Griffith

        Thanks, Arnold! Hope all is well with you.

        1. awaldstein

          Yes…things are great.In London end of May so maybe we can meet up.

          1. Carl Rahn Griffith

            Cool – that would be great – just ping me nearer the time and I can also intro you to Rob and Petra, who are now based in London – remember Petra gave you some tips re: Vienna a year or so ago when I introduced you to one another on Fb?

          2. awaldstein

            Yup. I remember. Only there for four days but I’d love to meet.

          3. leigh

            come visit Toronto Arnold.  So much closer 🙂

          4. awaldstein

            Been thinking about a visit to engagio….The Sky Dome used to be my account when I was selling live video compositing with a startup called Digital F/X. Toronto is a great town. 

    4. fredwilson

      Mazel Tov! Pubs make for great startup creation stories

      1. Carl Rahn Griffith

        Rav todot! (I think – I was OK at a few such expressions/phrases when I was working in Tel Aviv quite often – how I miss that place/people – anyway, I have forgotten many of them, or at least certainly the spelling of, now – apologies if incorrect – I am sure you get my gist, Fred!)  ;-)The proliferation of fine pubs in London and Yorkshire/etc should make for a vibrant startup community over here (just like Manhattan) – maybe we’re missing a trick, here – being too focused on the continental cafe-culture for meetings, chat, nurturing ideas and startups – we need to do more brain-storming in pubs, clearly! :-)Shalom!

      2. markslater

        i’ve counted 5 companies started thanks to a drink!

  4. John Revay

    Thanks for sharing.1. Throngs Neck – so it seemed like you traveled to the Island to close the deal w/ Jerry,2. I recall reading once that you blew off one of your first meetings w/ Jerry – your daughter was graduating from Kindergarten,3. It’s great that The Gotham Gal supported and encouraged your start-up move – gutsy call on her part – It must of took some soul searching w/ your family just starting to come of age.#GreatRun

    1. Fernando Gutierrez

      Re 3, I think nothing as important as that can be made without family support. And it shouldn’t, decissions affect everyone a lot.

  5. Fernando Gutierrez

    I was slightly drunk on a Friday night seven years ago. I made a bad move while going down the stairs in a bar (i.e., I fell) and injured my knee. Back then I was working in ad sales and the physical therapist that was helping me made me a few questions because she wanted to get new clients. I had had a difficult time to find a good therapist that could work on the hours and places I wanted, so I created a business around that. They new nothing about sales and ads and I new very little about their craft, but I hired a few of them, filled their time with new clients and made a nice cut. Nothing really new or fancy, but it’s paid the bills since then and recently it has allowed me to focus on other things.I guess I could say I owe my freedom to vodka.

    1. Kasi Viswanathan Agilandam

      Did you check there was an apple on the ground where you fell?  🙂 (reverse_Newton effect).Now that is an interesting story for funny friday start-up … What was the name of the company … anything that sounds like Vodka or reminds of Vodka?Interesting story… you solved your pain and others. 

      1. Fernando Gutierrez

        No apple to blame, just alcohol!The name is A Mano Fisios, which can be translated as ‘physical therapists at hand’. Never thought about including vodka in the name, but maybe you are right and I should have been more grateful to my drink 🙂

    2. fredwilson

      Falling down stairs! That’s great

  6. Me

    That was crazy no funny! 😉

    1. Me


  7. Kasi Viswanathan Agilandam

    My first start-up … the start-up was not funny … but how it failed was funny will share when there is a Funny Fail Friday’s. (FFF -day)

    1. Emily Merkle

      Oh I have a gem as well…

  8. Tom Labus

    Late 90’s I was managing a jewelry manufacturing co with plants in Thailand, Japan and India.  It was pure wholesale to department store chains and QVC.The Internet was at hand and this business screamed to be taken direct to the consumer.  I some how convinced the board to fund this as a hands off subsidiary (they were terrified of their US customers finding out).The culture and model were at opposite ends of the spectrum but it was a lot of fun.  Talk about winging it, there was nothing in place from talent to shipping to software.  It was cobbled together daily and sometimes a few times a day.I loved every minute of it.

  9. Brad Lindenberg

    In 2004 my dad cut his hand really bad while building shelving for a customer. He is a carpenter. He also loves golf. He couldn’t work for a month as his hand had to heal. He was browsing the web for golf clubs and found that sold golf clubs for $11 from China. He showed me and I decided to import 50 of them. They sold on eBay for $90 each and I sold out in two weeks.Four years later, my golf brand, Lind Golf, was acquired by Australia’s largest online department store. I’ve never played golf before :)I’m now using the proceeds to roll the dice again and seed my next startup and loving every second of it.If my dad hadn’t cut himself, I don’t know what I’d be doing right now. Don’t know if its funny, but its my story.

    1. fredwilson

      You never played golf and started an online golf store?? Wow

      1. Brad Lindenberg

        Yes! We manufactured – so it wasn’t just retail. I set up supply in China with our own branding across the entire range, had tooling made etc. actually kickstarter would have de-risked it if it was around. The funny part was that in the early days I was fielding calls to a 1-800 number from golfers who saw my ads in Golfers Digest. I was being asked things like ‘what clubs should I use to correct a slice?’ then I’d say ‘do you mind holding the lines are busy here’ and quick hit up Wikipedia for ‘golf slice’ – I learnt how to sell golf clubs over the phone pretty quickly. :))

        1. sbmiller5

          Brad, you should meet the guys at MatchBox Labs – let me know if you want an intro.

          1. Brad Lindenberg

            That would be awesome ­ brad [at]

        2. Ruth BT

           Hey Brad, love your story been following since the early days and know a few guys you inspired to be just as audacious!

        3. Donna Brewington White

          That is so funny about using wikipedia to answer questions.  I’ve experienced a few moments of instantaneous expertise in the middle of a phone convo thanks to Google.

  10. Emily Merkle

    I don’t know if you guys will consider this a “fun” story, but here goes:Grew up in the digital media space working for Bucketheads, to use a Brad Feld-ism. Learned the ropes working in viper pits for underdog startups with very little room for slacking – 100% commission plans, etc. working at a disadvantage hones silks like a mother. Met my husband and partner in crime at my first gig. Grew up in the space working for a variety of companies representing different but complementary facets of the digital media ecosystem. Got burned a couple times. Learned what not to do. We – my man and I – finally reached the point where we had the confidence to go for it, and found a likeminded partner to hook up with. Mediality was born Q2 of last year. Profitable without question. We know what we are doing, we are doing it for the right reasons, and best of all – this is my life. I love what we do, I live and breathe for this word. And I know we are more than capable. Now Emily inserts abject appeal: I am trying to take things up a notch. I want to connect with mentors to help us navigate the greater space. I want to keep learning. We are intelligent, humble, obsessed, and ruthless in a good way. If anyone in this community wants to take a flier on someone you don’t know – rock on. It is exceedingly difficult to break into professional circles as an unknown. But I am not giving up until I do. Because I know we have more than a fledgling startup here. We are working on a gamechanger. Amen.

    1. Emily Merkle

      And did I mention – no backing.

      1. leigh

        that’s the most fun part of your story.  what’s the url of your company?

        1. Emily Merkle

          http://mediality.comSite not at all illustrative of our actual value prop etc – it’s an ad network.

  11. Matthew Lenhard

    Good thing you had your wife there to save the deal :). Anyway I have an interesting start up story to share myself. I attended a class at the Wizard Academy ( a 21st century business school ) where the goal was to go from concept to revenue in 72 hours. We ended up going into 3rd day about 2 days behind schedule after hitting setback after setback. Somehow we managed to pull it all off and we launched on the 3rd day getting something like 18 orders over our first night are still going strong today. 

    1. falicon

      I love the Monday morning memo for the Wizard Academy (and all of Roy H. Williams books actually)…look forward to it every week 😉

      1. Matthew Lenhard

        Great to meet another Roy Williams and wizard academy fan in the AVC community. BTW, I am a huge fan of the Monday Morning Memo as well.

  12. aysha ali

    Hi Fred, great topic! My startup story so far goes like this…In 1998 a kind person donated a PC to my class, that day my teacher explained the concept of the world wide web. Since then I couldn’t get this idea out of my mind. 14 years later at 23 years old i have started to build it. Its a revisualisation of the browser experience 😉

    1. fredwilson

      Have you evolved the idea in those 14 years?

      1. Aysha

        Yes the idea has evolved, but the central vision is still the same. Its crazy but having started the build in late December, we have found that the technology needed is only now becoming powerful enough to support our product Hopefully we will be able to show you our alpha?

  13. RichardF

    Mine started in a nightclub.  I was on my third VC backed start up in finance. As the main finance guy I was winding down a dotbomb for the investors to enable a redistribution back of the remaining cash and thinking about my next gig.  I’d always enjoyed working in start up but really wanted to work for myself.I was in a club with some friends and was at the bar getting the drinks in when I received a text message from one of my friends across the room who happened to comment on the pretty girl standing next to me in a red dress.  When I returned to where my friends were the conversation went from the girl in the red dress to wouldn’t it be funny to be able to send a text message to a screen in the club.  So that’s what we decided to do, enable business to send and receive sms, including text to screen.We are now working on an app, that is in beta with some of our existing clients which incorporates sms but is not the focus of it.  Out in the wild v soon.

    1. Fernando Gutierrez

      And what about the girl????

      1. RichardF

         I’m a married man, Fernando, as my wife says  “you can look but you can’t touch”

        1. Fernando Gutierrez

          That’s a great way to keep problems away :-)BTW, best of luck with the new app.

        2. JLM

          It does not matter from whence your appetite arises as long as you always go home to eat.

          1. sigmaalgebra

            Reminds me of the ketchup ad that said: “He gets it at work.  Why not give it to him at home?”.Soon they pulled the ad!

          2. Donna Brewington White

            Oh, Siggy… you are at it again.

          3. Donna Brewington White

            However, you may want to add…  If she is not the appetizer, it is wise not to let her know this.  Otherwise you may find yourself having to skip dinner… and dessert.  Just sayin…

    2. Carl Rahn Griffith

      That’s cool – for all the sophistication of modern messaging, etc, I have mulled over something similar for a long time – just a simple scrolling LCD type display that can affix to a fridge/whatever at home and family can send SMS messages to it – running late, won’t be home, get the oven on, etc. Simple is good.Look forward to hearing about your project – sounds fun.

      1. RichardF

        simple is good and also really hard to do well, feature creep has been a constant issue.

        1. Carl Rahn Griffith

          Exactly. So hard to resist – especially if one’s development team is of the ‘rock star’ culture. Mind-blowingly frustrating. Pragmatism is KIng, often.

    3. markslater

      aghh ha! we should talk!

      1. RichardF

         we should, I’d like your take on Twilio because we will be looking at a US supplier but I don’t think Twilio are tier one, not that it matters much initially.

        1. markslater

          Twilio is the single best piece of technology i have seen in years. its a simple choice rich:- deal with the carriers, pay out the nose, wait months and be stuck trying to innovate on the SMS stack or- integrate twilio, be live in days, pay as you go, and get on with the important stuff within your business.remove the telco challenge rich – otherwise you will be carrier addicted. twilio is live in europe – we will rollout with them there when we get there – it will be like flipping a switch. if you want to know more or chat with my CTO about it just PM me.

          1. RichardF

             tx muchos Mark

          2. falicon

            +1 on Twillio …it’s the secret weapon that got GroupMe off the ground…and it’s simple, reliable, and very affordable when starting out (great for startups).I also use a service called for a handful of my projects that I’m in love with…the reason I bring it up is that it’s basically Twillio for email (at least that’s how I explain it to everyone).  If you have a need for transactional email (I’m a big believer in transactional email), or even just want to make sending/receiving email via your service super easy/clean, check them out. 

          3. RichardF

            thanks Kevin, looks like Twilio it is a part of our new service, currently using Amazon SES, which I have to say we have no problems with but will check mailgun out.

          4. kidmercury

            agree totally on twilio being the best piece of tech in years……outstanding work they’ve done. 

        2. markslater

          oh and twilio integrates with EVERY carrier that matters here.

    4. fredwilson

      I’ve seen variations of this idea. Nobody has nailed it yet

      1. RichardF

        it’s just a niche product for us, clubs will use stuff like this for about 6 months and then move onto something else.  It might be streaming twitter or  facebook comments.It’s the boring stuff that makes the recurring  money.

        1. Rohan

          ‘Variety may be the spice of life, but monotony is what pays for the groceries.’

      2. markslater

        people do it with twitter – i’ve seen it in clubs. #<clubname> <message>

  14. Rohan

    Oh wow. Quite the topic. Let the craziness begin!

    1. Max Yoder

      I will never tire of reading your comments in my head in a Yoda voice.

      1. Rohan

        Just like I never tire listening to ‘old couple in a caravan’. 😉 

        1. Max Yoder

          🙂 thank you for saying that, Rohan. Means a lot.

  15. Ariel Di Stefano

    Our latest idea (Shopperception) started while we were dinning with a friend from marketing research industry in my house and he saw my 3 years old son playing with the Kinect. He asked if that “thing” could be used outside gaming…. Long story short, after some pivots and lot of work, we came with a very innovative usage for MS Kinect and found a great response from everywhere.

    1. fredwilson

      Kinnect as a platform. Should be more kinnect based services. How many Kinnects are in the market?

      1. Ariel Di Stefano

        Well, before the launch of kinect for windows (FEB. 2012) there were something around 18MM Kinect for XBOX.

  16. Mark Mc Laughlin

    I purchased 2 standing tickets for Oasis at the Clapham Grand in 2005. It was a warm up show in a very small venue and there was only room for a couple of hundred standing tickets available so was delighted to get them as they were my favourite band during the 90s. When my tickets came they were 5th floor seating. The Clapham Grand was more of a late night club that you would go to whenever every other option had been ruled out (i.e. nowhere would let you in) so I had frequented the venue more times than I would care to admit so I knew the layout of the venue well so was not happy with getting the wrong tickets. I was taking a week off between jobs so it became a mission for the week to get this sorted. I initially called Ticketmaster customer service in the UK and got nowhere. I then tried Ticketmaster in the US and got nowhere. I then looked up the names of those on the board and figured out their email addresses. I sent them all a group email saying that their UK operation was fraudulent and that I had taken legal advice all of which was rubbish. I got an email back from someone on the board saying they would sort this. They emailed the head of Ticketmaster in the UK who called the venue to get this sorted so I got my tickets and the show was a great one. The whole episode got me thinking that there must be a better way of doing ticketing so I put the words tickets and technology into Google and started reading which started my journey into start ups and ticketing with experiences and learning that I never imagine would happen so I’m grateful for Tickemaster trying to screw me on my Oasis tickets!

    1. kidmercury

      oasis is my favorite band too. #madferit

  17. Emily Merkle

    my last venture I was running ops – PPC ad network. No interface. No Analytics. No talent ’cause we were bootstrapping. Scraped our way to break even in 4 months. Very lean times. I had invested in this venture on the basis of advanced and pliable traffic filters to do the kind of granular optimization I wanted to do. Delays. Delays. More delays. I grew increasingly concerned then impatient. Finally practically forced our lead (he financed) to level with me. Turns out – the technology was for all intents and purposes nonexistent. And was not going to materialize. Not cool. That was a deal breaker. I could not in good faith continue ops with clients and partners under false pretenses. I walked away the next day after notifying my clients. Startups are a bitch – but I can surf anything except deception.

  18. William Mougayar

    I started 3 different businesses over the last 17 years, and a couple more products inside the first one. The common element among them was the result of Dissatisfaction with something. Dissatisfaction is the mother of Action. 

    1. Dan Epstein

      Solve your own problems!

      1. William Mougayar


        1. Dan Epstein

          Loved your quote: Dissatisfaction is the mother of Action. I think great ideas come from people deciding to solve their own problems, rather than wait for someone else to do it. Mine have.

          1. William Mougayar

            Got it. Thanks. If you see your own problems before others do, then you have a huge market opportunity in front of you!

    2. Kasi Viswanathan Agilandam

      Necessity is the mother of invention.Dissatisfaction is the mother of Action.Pissed Off is the mother of Start-ups….and Kick-ass is the father of the start-up.

      1. leigh

        I fall into the pissed off category (of course)Tired of people i worked for giving me the gift of feedback on the one hand (could you just do it more like how i want you to?) and then taking all the money I helped make them in the other hand (oh apparently your way worked mea culpa)Sometimes it’s just time to put your own money where your mouth is.  

    3. JLM

      Harnessing anger and dissatisfaction is the source of energy that changes the world.When you get angry enough, you WILL act.

      1. William Mougayar

        I’m angry everyday about something 🙂

        1. Rohan

          Hope you’re watching out for your blood pressure as well, Will.. 😉

          1. William Mougayar

            Not that kind of angry 🙂

    4. panterosa,

      I was a springboard diver, so I say Anger is my springboard into action. I get things done when I’m pissed off at how stupid something is. 

  19. John Best

    I think the trend will universally be dissatisfaction with a business or industry. I think that the startup is born when instead of saying “surely there must be a better way to do this”, someone says “I could do this better”.

  20. ei_dscanlon

    Only thing I’m “starting-up” at the moment is my family: when #3 arrives next week we’ll have 3 under 4 years of age…Thought it would be worth sharing this collection of start-up stories over on OpenIDEO, it’s part of a challenge from the European Commission to help more Web entrepreneurs to grow and scale:…

    1. JLM

      Technically, you are going from man to man defense to zone.  Good luck w/ that.

      1. ei_dscanlon

        Any and all defensive strategy tips welcome 🙂

  21. andyswan

    Visiting brother in NYC.  Told him I hated law school, said “we have to start something to get me out of this.”  So we sat down and…1.  Wrote 3 pages of the worst copy ever2.  Bought a “hosted URL” and posted our copy up using Dreamweaver3.  Plugged in PayPal and made up the price of $249/month because “4 customers will pay our rent.”4.  Spammed the shit out of Yahoo message boards5.  Went out, got drunk and talked about how awesome this was gonna be6.  Came home to a signup:  Jeffrey EarlDaytradeTeam was born.  Didn’t go to another class.  Dropped out (Boston U) after cashing my final stipend check for the semester.Makes me think I’m an idiot for putting so much thought into our third one.  LOL

    1. Cynthia Schames

      Good Lord that made me feel really old for some reason! Hahah!

    2. Aaron Klein

      Love this story. I’ll never remember Dreamweaver the same way again.Aptly named product, if you think about it…

  22. $3236

    Had a great job in the early 90s helping Knight-Ridder diversify away from newspapers.  In 1995 Knight-Ridder CEO (Jim Batten) dies suddenly and the new CEO is Tony Ridder who decides to make Knight-Ridder a pure newspaper play.  Really!  So it was time to go…

    1. fredwilson

      I bet a bunch of startups were born at yahoo this week

      1. Elia Freedman

        Let’s hope anyway.

  23. Cynthia Schames

    My first startup was born from being laid off from two high paying enterprise sales jobs within two years (during the first dot com bust).  The second layoff happened literally the day before my wedding and I just got really, really pissed off.  So I came back from my honeymoon and started my own company following my passions: sales, buying stuff online, and collecting really expensive handbags.  Within the first 18 months I was doing over $2M in sales at shockingly high profit margins and had three full time employees.  Kept it up until I had twins in 2008 and wanted to scale back the constant international travel. Oh–and I never solicited or received a penny of outside funding. Totally bootstrapped for nearly 6 years, and profitable after the first 9 months.So that’s my startup story so far.  Who knows what the next chapter will hold, but I think it will be an intriguing one! 

    1. Donna Brewington White

      Now, your tag line makes sense.  “I sell.”  Love the simplicity of that, and yet it says so much.

      1. CynthiaSchames

        Thank you, Donna. My secondary aim in life is to convince certain people that “sales” isn’t a dirty word. At the core of it, we all sell.Some of us are just more forthcoming about it.

        1. FAKE GRIMLOCK


          1. Cynthia Schames

            ME GLAD YOU SEE.:)

  24. EmilSt

    It was April 1992, I was 18 and last year in high school. A friend of a friend was about to close his flower store. I borrowed 700$ from friends to buy his furniture and take over the lease. I was hiding this from my parents for 3 months until I entered into coledge. By that time I was also making enough profit to justify my venture. This was my first startup almost 20 years ago. Since then many other followed that defined my life.

  25. William Mougayar

    It seems that getting drunk or drinking is an emerging theme. I wonder if that should become part of the Lean Startup process. Wanna start a company? Get drunk & it will come.

    1. bsoist

      I noticed that theme myself. Interesting how drinks are are mentioned in several of these stories.

      1. Carl Rahn Griffith

        Ahem 😉

    2. Fernando Gutierrez

      That makes some sense. When drunk we are fearless and fear is one big obstacle you have to overtake to start something new.Or maybe it’s just that alcohol can be funny and this is fun Friday, so we all bring our drinking stories here.

      1. JLM

        Genius observation.  Pure genius.Well played x 10!

      2. William Mougayar

        Add to the fact that Fred’s handle is Bartender. hello.

    3. Kasi Viswanathan Agilandam

      NO.That tells drinking is part and parcel of every day life of many entrepreneurs.Now. If you excuse me …. i am off to the real bar….sorry…. going to start the next Google :-).P.S. btw. You forgot Fred’s title in this blog.

    4. markslater

      call it the leaning startup process

    5. andyswan

      Honesty, boldness, social interactions, inhibition and a mind uncluttered by “facts”, “reality”, and “restrictions”.It works.

      1. William Mougayar

        Unlike cars or machinery, when drunk a pen or keyboard are safe.

    6. Fernando Gutierrez

      Having kids or being pregnant also seems to be quite a common trigger. So if the company doesn’t come while drunk you can at least work on the pregnancy issue to get a second chance then 🙂

      1. Donna Brewington White

        It’s amazing how having kids makes you want to change the world.And how much it changes your world.

  26. JustCurious

    Just curious, do you call your wife Gotham Gal like, during, private, moments?

    1. markslater

      or after a few drinks! (seeing as drinking is a theme on this comment thread)?

    2. Rohan

      This really is fun fridays.. eh..

    3. fredwilson

      Never. But I try to always refer to her that way online

  27. falicon

    I have a few, but the most interesting/successful one I’ve done mostly by myself to date started with me running a small fantasy football league for a group of my friends. It was in the mid-to-late 90s and I had built a fairly simple web-based fantasy football management system for us to track and play the game, but every week one of us had to sit down and manually enter the stats for every active player. It was painful, took at least a couple of hours, and often had errors (which ALWAYS led to internal bickering).So I started reaching out to every other person I could find online that did something with stats or fantasy football. All I was looking for was an affordable way to automate our league scoring. The main provider at the time (and still actually) was Stats Inc. but they were really only for large companies (huge up front fees, large revenue share, horrible legacy technology) – simply not an option for a group of 12 friends just trying to automate one league. The more people I reached out too, the more I realized that lots of people had this same problem (and many at a much larger scale than me).Throughout this search, I got a lot of “if you find it, let me know because I’ll subscribe too” comments…and I started to realize that my best option to solving my problem was probably to just build what I needed myself. Around that time, I also hooked up with a few key players in the fantasy sports association that was just getting off the ground and they really pushed me over the edge to finally build it (they convinced me that if I built it, they would subscribe themselves and they would get a handful of others to also subscribe — so basically I had clients, and I had ‘sales’ support, which meant it was time to start building).The business quickly developed into a nice lifestyle business that I basically ran as a one-man show for a number of years (it had lots of potential to be more than just a lifestyle business, but there were legal risks around stats at the time that I was not willing to challenge and so I intentionally kept the business small and mostly under the radar; happy to gobble up the small to medium sized clients that nobody else wanted to serve affordably).

    1. bsoist

      “if you find it, let me know” – that’s a great thing to keep hearing, huh?Excellent story! 

      1. falicon

        For sure! Thanks 😉

        1. bsoist

          My wife and I actually ran a very small home based business related to fantasy sports based on paper and pen – back before normal people knew about the Internet. 🙂

  28. karchitecture

    Great topic! I wrote a blog post last summer that captured our founding story – “Why I named our company Knowledge Architecture.” this conversation took me back to it and it actually helped me solve a problem I have been wrestling with this week. Sometimes the old you can inspire the new you, a clear benefit of writing things down.http://knowledge-architectu

  29. bsoist

    My first startup actually never launched but it was the catalyst that put me where I am today. In the late 90s, I had a friend who had dropped out of high school because his mom died of cancer and because he was much smarter than most of his teachers. He worked hard and saved as much as he could. He and I connected one day about making something out of this Internet thing. He knew I was a programmer, and he had some cash to make things happen.Meanwhile, my brother, an MBA finance guy, and I put together a team of 10 for a separate project. We had some very smart people on the team. We met for dinner, ( and drinks 🙂 ), which led to a great brainstorming session on a Fri/Sat, where we made a plan to start researching our ideas (we joke now that we invented something very similar to Facebook that weekend). Only 3 of us were actually following through on our research, so I made the decision to cut loose and continue working on “small time” ideas with my friend. We launched a few successful websites which taught us some very valuable lessons. The most important lessons – 1) not every idea will succeed, 2) some of them will, and 3) this Internet thing does have profit potential.I am currently working with a new startup related to game-based education. Too early to finish that story.

  30. Adrian Palacios

    “Fortunately the Gotham Gal closed the deal with Jerry for me.”That’s awesome. Such a dynamic duo!

    1. Carl Rahn Griffith

      The ultimate in teamwork – my wife, Helen, is similarly my rock, my mentor, my compass.Best feeling in the world.

    2. JLM

      Haha.So now we know who was the real founder and deal Princess extraordinaire of USV.Well done and well played all around.I hope in moments of great triumph the GG smiles and whispers — “Well, darling, just remember who put YOU in the VC business.  You’re welcome.”I wonder how many great business decisions have been made mid-span on the Throgs Neck Bridge. Throgs Neck Ventures

      1. Carl Rahn Griffith

        ‘Throgs Neck Ventures’ – lol – well, it’s certainly distinctive! 

      2. Rohan

        As they say.. behind every successful man……..

        1. Max Yoder

          Are his parents taking the credit 😉

        2. LE

          (Pertains to spouses: wife husband..)To see how true that cliche is, you have to be married for some time to the wrong woman/man and see how it difficult it makes everything. 

          1. panterosa,

            My wasband had no real interest in me succeeding. That’s half my divorce motivation, and how I put the “was” in husband.

      3. fredwilson

        Yes. That’s pretty much how it goes

  31. Lisa Mogull

    Was at a sushi bar that doesn’t have hot towels and the guy next to me looked panicked when his huge, expensive meal arrived.  I reached into my bag and said “I have a seven-year-old — would you like some Purell?’  To be polite he asked me my name and what I did and I asked the same.  I was horrified when he said “insurance” thinking I was wasting my evening out (was happily solo reading the New Yorker) and the 40 bucks the sushi cost while stuck chatting about insurance.  The next day he sent me some links to trucking websites and CentricSocial was born. My co-founder Michele and I knew each other from negotiating a strategic partnership a decade ago.  We met again a few days before insurance sushi dinner two when it turned out our kids were both starting at a new school and were in the same class.  I was a little nervous and asked her to join me as my “wingman.”  She turned out to be the perfect co-founder.

  32. markslater

    its not mine its my friend Greg but i am going to tell it anyway. It was 2002 i had just left CMGi and was thinking about what to do next. My wife and i lived in an old piano factory which was a community of artists and entrepreneurs here in Boston. i was looking across my courtyard one morning and saw my friend Greg moving boxes in to a unit. I walked over and asked what he was doing. “i am starting an ecommerce company called karmaloop”. “good luck with that” i said – bad timing would be the understatement for starting an ecom company then. (he was also doing his masters as the kennedy school) He asked if i wanted to help. I was “in between” and said “yes why not. IF i am going to make a stupid decision why not do it with a friend” Fast forward to 4 years later and he was still struggling but had made good progress – he asked if i would invest – i said yes because he was my friend and there was something about him that refused to quit….and most importantly he needed help. so i helped some more. Fast forward to today. Karmaloop is the number 1 global ecommerce site for street culture. It employees over 300 people, will do $240M in revenues this year and is on its way to being a billion dollar company. Not a single VC invested in boston – in fact most have not even heard of it.And the best part – my little company today has greg as an investor and on my board, and karmaloop as a partner and we are still good friends. he mentored me just last week through a sticky issue with an employee.It has to be about more than money – it always has to be about more than money.

    1. andyswan

      Three key points to this story:1. there was something about him that refused to quit2. there was something about him that refused to quit3.  there was something about him that refused to quit

      1. markslater

        and if you were to meet him you would realize how completely right you are.everybody told him no. i mean everybody

        1. Alex Murphy

          except for himself … 

          1. Fernando Gutierrez

            and Mark!

          2. markslater

            his cellphone is on the about us page of the site. it actually rings him. he takes calls from customers all day and night. its 617.216.1013 – tell him i said hello and congratulate him! – tell him we were chatting about him on here!

          3. markslater

            here is his story in fast company… 

      2. William Mougayar

        Common trait in entrepreneurs. Count me in.

    2. Givengi

      I absolutely love this story! Thanks for sharing! Super inspirational!

    3. Bubble Baths

      I love Karmaloop! Haha, this story is so inspiring to me and you are a great friend

  33. mike gilfillan

    Was job-hopping out of college (quitting, getting fired, or both) but kept landing better and higher paying jobs as a contract IT professional.  Friends and future wife said “you should write a book about the contracting industry so others can do what you’re doing”.  So I did.  Self-published it using the income/savings my gf and I had. Got it into bookstores on my own, but my book distributor went bankrupt and kept half my inventory (I could only store so many boxes of books in my small apt). While attending a job fair to look for a job and hawk my book, many of the recruiters  commented on how much they spend on classified ads in the local paper.  I promptly went home and counted up the total cost of all the wanted ads by line-inch using my ruler and figured “there had to be a better way”.  Was looking into a BBS software (this was late 1994) when a friend told me about this new thing called the world wide web.  I got online and realized the potential to reach other IT professionals and help them find jobs.  I learned html and used my database programming skills to create my first site, a job board.  Launched it the same month I got married.  We paid for small ads in the local IT publications (ComputerCurrents?), got listed on Yahoo and grew to a $5m profitable business with 30 employees in the first few years.  Life was good making money & helping thousands find better jobs. Took on VC in late ’98 and rode the dotcom boom and bust until we sold it in late 2006.   Now back in startup mode teaching myself rails so I can bootstrap all over again (at 43).

    1. Richard

      Great Story. Trying to learn ruby/rails as well. Dont think twice about your age. Other than the lanaguage processing, there is little the the brain does not due better with age (that is if you take care of it). See the recent harvard study published in the peer reviewed Archives of Internal Medicine. 110,000 person / 30 yr study.

  34. jptucker

    In my first year of college, I was one of the first members of a little-known website that helped connect buyers and sellers of tickets.  At the end of the year, the founder of the site announced to its members that he would be graduating, and would be auctioning the site off to its members.  I saw potential so I started collecting my thoughts around what to bid.That summer, I was playing poker with some high school friends, shooting the shit.  My buddy, a guy that I grew up across the street from, mentions that he’s considering bidding on a website.  We were, of course, about to bid on the same site, so logically we pair up and go in together.  We win the auction and were the new owners and operators of our own business.And that’s how I became an entrepreneur over a game of poker.

    1. fredwilson

      poker and business are two sides of the same coin

  35. Max Yoder

    I grew up in northern Indiana in a county called Elkhart in a city called Goshen. When it came to year-over-year unemployment rates, the recession hit my area harder than any other place in the nation. I watched a lot of wonderful people lose their jobs, and I spent a lot of time praying that my mom wouldn’t lose hers. I’m forever thankful that she didn’t, but the impact was made. From those days on (though I’m not sure I fully realized it at the time), I was in startup mode.

    1. sigmaalgebra

      Been there.  It’s not far from Warsaw, and 15 miles south is Claypool, mostly just a crossroads about a mile east of NS route 15.  Go a little east is NS County Farm road running south out of Warsaw.  There are two churches in Claypool, and I got married in one of them.  Her father had a farm on the east side of County Farm and long ran the REMC in Warsaw. His family had some amazing girls — a Fair Queen, a Ph.D., an LLB, Craveth, two PBKs. He was a great guy, like 20 hours a day for six days a week and 10 hours on Sunday, built his house and farm buildings nearly all with his own hands. The family looked like something out of a Norman Rockwell painting.

      1. Max Yoder

        Yeah, traditional farmers in general possess drive that is beyond me. You nailed it! I’ve been through Claypool, but never really in it, and I’ve spent plenty of time in Warsaw :)I was also raised to love Rockwell, but I was always partial to Edward Hopper.

  36. Alan Warms

    When I was 12, I asked my Grandfather how he started his own butcher shop (Melrose Butchers on Columbus and 96th for those of you who were around before it burned down in ’74).  His response was if you want to start your own business, go work for someone else in the same business first and learn it.I was fortunate to work with Mark and Sunil at Freeloader, and then with James Tito at eShare. After being the number 11 guy at two startups, my attitude was, I am ready to do this myself.  I think half (at least) of every origin story has got to be the moment you step out and say, ok, no W-2, no nothing, this is on me.Great post, Fred!

    1. fredwilson

      I had a front row seat to your story Al

      1. Alan Warms

        Likewise on yours! 🙂

        1. fredwilson

          true, true

  37. andyswan

    This thread should be tagged as evidence in the argument against prohibition.

    1. Carl Rahn Griffith

      I just wish we had this kind of ‘social media’ back when I lived in New York (2003) to help the old serendipity along, so back then I could have bumped into Fred/Jerry/etc in Chumley’s (RIP) – I tell you, the world would have been a different place! Or, we’d have had a few fun evenings, at least 😉

    2. fredwilson

      i think we are done with that experiment in this country

      1. andyswan

        Only with alcohol…

        1. fredwilson

          correct. there’s a few other vices i would legalize and tax if it were up to me

  38. Carl Rahn Griffith

    I wonder how often it has been accomplished (ie, a successful startup) in isolation or with a co-founder who is not a soul-mate – not just without a partner/spouse, I mean – but without other key people/friends who you develop the initial ideas with and subsequently establish the venture with? Also, I suspect that other key person/s being a friend is vital in helping chances of success – ie, someone you have an empathy with. If it’s all done too clinically – eg, I am the techie but I had better get someone on-board to do the commercial stuff – it must surely make the task a lot harder, less intuitive…?

    1. Brent Weber

      Carl,In my experience co-founding with a close friend has more cons than pros.  You are less likely to be brutally honest when needed.  I prefer the “clinical” style for business.  Tough business requires tough decisions.  To me meetings should be “This is a business meeting, so our personal feelings stay outside that door.”  It is amazing how close friendship can drop a group’s maturity a few notches.That is my personal experience and I know there are all kinds of people.  Some people probably would have more issues with someone who wasn’t a close friend.I would be interested in Fred’s or other investors perspective.  Does a team being close friends pre-business affect your decision to back them?

  39. Aaron Klein

    @Riskalyze:twitter was a two year process to get started and it almost didn’t happen.The retired inventor of the core tech approached me and a friend two years prior about doing a company around this. The model – charge people $35 to construct a portfolio of investments that fit them – didn’t feel right to me. And even though it looked great to me, I couldn’t quite figure out how to validate that the core tech worked.So I turned it down.Two years later, I’d been working with people from the brokerage side of the business and had a much deeper set of connections and understanding of that business model. I had been in discussions to join a different company as VP Business Development, but the talks weren’t going anywhere. Unbeknownst to me, my friend had found a physics grad to build a rough proof-of-core-tech prototype and had the validation we needed.At a dinner, I casually asked “anything ever happen with the portfolio technology?” and the response was “I sure wish you weren’t tied up with a new job.” I blinked in surprise. “I’m not.”I pulled out a blank sheet of paper and started diagramming where I thought we could take this. It took a few more months, but we negotiated the technology into the company with the inventor, the physics grad agreed to come on board as a co-founder, I convinced one of the world’s greatest design engineers to join as the third co-founder, and the investors came aboard.We got rolling March 1, 2011. We’ve been going 90mph ever since…and loving it.

    1. andyswan

      You’re onto something, without question.

      1. awaldstein

        Couldn’t agree more.

    2. Richard

      Harry Markowitz!

      1. Aaron Klein

        The inventor of our core tech built on a lot of Markowitz’ work. Amazing guy.

    3. sigmaalgebra

      So, you did the Harry Markowitz optimization? So, that’s find a portfolio that minimizes risk subject to a given expected ROI where risk is a convex function and a quadratic form of the portfolio and the expected ROI is a linear constraint in the portfolio? So, attack this via the Kuhn-Tucker conditions, the Wolfe dual, and linear programming?Why is this physics instead of operations research?Operations research references could include:Willard I. Zangwill, ‘Nonlinear Programming: A Unified Approach’, Prentice-Hall, Englewood Cliffs, NJ.Olvi L. Mangasarian, ‘Nonlinear Programming’, ISBN 07-039885-2, McGraw-Hill, New York.G. Hadley, ‘Linear Programming’, Addison-Wesley, Reading, MA.It would also be good to do an integer programming solution as in, say,George L. Nemhauser and Laurence A. Wolsey, ‘Integer and Combinatorial Optimization’, ISBN 0-471-35943-2, John Wiley & Sons, Inc., New York.Then there’s the issue of ‘portfolio re-balancing’ which may want a stronger role for integer programming?Then there’s the issue of good input data on the expected ROIs and the variance-covariance matrix.If believe W. Sharpe, then all this has been done already by ‘the market’ and, thus, should just buy ‘the market’ as in an index fund.

      1. Aaron Klein

        Too busy today to get into a deep discussion of the underlying math. Suffice it to say that our core tech is a dimension above Modern Portfolio Theory, iterating both risk and reward to optimize for the quantitative mathematical function we capture from your unique Risk Fingerprint.In other words, we allow you to make objective what portfolio allocation has historically left subjective.I hope you’ll give it a try and see what you think, though someone with your set of ISBN numbers might feel a bit constrained. 😉 We’re going for the broader market with this product.

        1. Dave Pinsen

          In other words, we allow you to make objective what portfolio allocation has historically left subjective.Well said. Great, pithy description of the unique value @riskalyze:twitter adds to the process. 

          1. Aaron Klein


        2. sigmaalgebra

          Sounds like interactive multiobjective (i.e., for both objectives of low risk and high reward) optimization to get a Pareto optimal (i,e., non-inferior) solution that is optimal considering the user’s utility function of risk and reward!So, an interactive process can end up estimating the set of portfolios that are non-inferior for the user considering their utility function.There was a guy who named such a thing non-inferior set estimation or NISE! He was one of my dissertation advisors! But it was still operations research instead of physics!I know; I know: The physics people know some Lagrange multiplier theory! Well, so do the operations research people!You got me: I always thought that von Neumann’s axiomatic utility function theory was just a bunch of smoke blowing and generalized, abstract nonsense!

        3. sigmaalgebra

          At first screen I get is one about browser compatibility!The site seems not to like my Web browsers! So, I have Internet Explorer 8.0.6001.18702IC and Firefox 3.0.4.So, I should upgrade, right? Hmm …: I’ve spent way, Way, WAY, WAY too much time in computer system management and administration and hate upgrading software, especially since often the new, better version replaces the old version instead of just giving me one more program I can run; they believe they are doing me a favor; I believe they are risking my computing.Then, there’s setting the options for the new version, and if the options settings change at all, then I get angry enough, to borrow a technical term, pissed, to go into orbit around Andromeda.I care so much about the options since by a wide margin the worst thing that happened to my startup was a computer virus I got from a Web browser. That it could be possible even in theory to get a computer virus just from a Web browser makes me, that word again, pissed enough to blast at warp 10^10 speed across the visible universe. In the history of computing, there’s no excuse for a browser letting in a virus; none, zip, zilch, zero, nichts, nil, nada, absurd, UNbelievable, outrageous, contemptible.All a browser takes in is simple data, usually just simple text; that some programmer couldn’t read such simple data without making a mess of the user’s computer is beyond belief.It’s good I was never in a place with both a chain saw and a browser programmer at the same time.The last virus came from just one use of the Akamai download manager Asus insisted be used just to download a PDF on one of their motherboards. So, Akamai is a famous company, right? They like math, right? They write a lot of software, right? Their software, just for doing a download should be okay, right? WRONG. As I found out too late, their software was a common virus vulnerability.After the virus, I had to rebuild everything on my boot partition, which was a lot of work. Then I worked to put in place severe options for security, some work to permit rebuilding more quickly, etc. It was a lot of work. I don’t want to add up everything that cost.So, my browser options now have each check box, each pull down option list, etc. carefully considered, set, and documented. I’m embarrassed to say how long that work took, but one can guess how little I want to repeat it.That work was a good place to apply “Never give up. Never quit” and Kipling’s ‘If…’.Firefox has Java enabled by default. Outrageous. Java can do anything. Internet Explorer keeps talking about “ActiveX”. I believe I know what that is, and I don’t want it active and want it passive or dead.There’s a 101 level rule in computer security: Never but never, not even once, don’t even think about it, permit data from an untrusted source to execute as software. Just don’t do it. But, of course, Firefox, Internet Explorer, and Outlook are just obsessed with violating this rule.And there’s a rule for operating systems: No matter what code a user executes, there shall be no harm at all to an operating system. Microsoft seems to have large cathedral doors wide open with large, flashing, neon signs reading “East European hackers, enter here, take over the operating systems of Windows computers, look for financial data, and steal it!”.The functionality of my browsers is cut back to the level of a sub-cretin with a frontal lobotomy, with the answer to the frequent “Do you want to?” being, to put it delicately, hell no. So, I have all plug-ins and add-ons disabled except just for Flash. And I realize that Flash has had vulnerabilities. And I download (simple, old, simple text) PDF files and understand that active PDF files have had vulnerabilities.BeYOND belief. I’m supposed to, what, use such software only in a sealed room with hazardous materials precautions and sneaker net any data back to my usual world? Computer security has been rock solid back to Prime’s Primos, MIT Project MAC’s Multics, and IBM CP67/CMS, but now we can’t even read text over TCP/IP without wiping out our work?”Buffer overflows”? Can you believe that any programmer could ever be dumb enough to write code vulnerable to a buffer overflow? Yet as of a few months ago, Microsoft was still fixing buffer overflow errors. And Gates is worth $50 billion or so, with buffer overflow errors. Amazing.And both Internet Explorer and Firefox routinely permit any other software, e.g., RealPlayer, to install browser plug-ins without notice. That’s like going to Dr. Iatrogenic for an anthrax injection.Uh, some users don’t want to change browsers! If my business works, I won’t change a Web browser unless absolutely necessary for less than $100,000. We’re talking barrier to entry here.I know; I know: The latest Web browser has 395,558,239,884 new security problems fixed. Right. And that’s what they said the last time. But the new browser no doubt has some new functionality, I almost surely don’t want, with almost surely some more vulnerabilities. And then there will new options I will have to enumerate, select, and document — no thanks. I was wrong: Make that $200,000.For my Web site, I’m insisting on a browser right up to date as of, maybe 10+ years ago. My site will use HTML5 or CSS3 some decades after I retire to a 50,000 acre estate.Your site has:> The questions are almost never the same for any one person; the algorithm determines each question based on your answer to the last one.and I can’t parse that! One might say:> The questions are almost always unique for each person; the algorithm determines the next question based on your answer to the last one.Your version seems to have no way to determine the first question!At the page with:> Do your investments still fit you? Capture your Risk Fingerprint and find out. It’s easy, and free.the screen shot seems to be blurry. About all I can see is a lot of blurred text and some big, red arrows. The image is a PNG and not a JPG, and that’s good.If I pull the PNG into Microsoft’s PhotoDraw and magnify it by 400%, then the text is still blurry but readable. Usually magnifications of PNGs of screen shots have each pixel quite clear. Was there a JPG conversion somewhere on the way to your PNG?The screen shot seems to have an X-Y graph without any axis labels.I’ve designed all the screens on my Web site to be 800 pixels wide, fonts 25 and 35 pixels high, with high contrast, and everything dirt simple.Your phrasing “Risk Fingerprint” seems to be a technical term and maybe a trademark, thus, to have meaning not just from a dictionary, and, thus, to need some explanation.Your screen says:> It only takes 5 minutes. Get started now.I didn’t see how to do that! I clicked on everything on the page, and nothing happened! Looks like my browser problems!

          1. Aaron Klein

            We support Chrome, Safari, IE 8+ and Firefox 4+. We don’t use ActiveX or anything like that.That being said, I don’t think we’re the product for you. But thanks for giving it a click.

          2. sigmaalgebra

            Of course, with your site’s response to my Internet Explorer 8.0.6001.18702IC, there’s some question about your support of “IE 8+”.It’s your business, but, again, in mine I’m trying to please nearly everyone on the Internet from a desktop to a smart phone with whatever basic browser. Currently I’m working to eliminate the need for cookies. As of yesterday, I believe I see how to do it!

    4. Mark Essel

      Wild ride Aaron.

      1. Aaron Klein

        indeed 🙂

    5. awaldstein

      Riskalze has a lot of assets. You are one of the key ones!

      1. leigh

        ok tangent for you Arnold — but what say you of this adage thing with Budwiser – where they are asking resource scarce startups to pitch against each other for a — wait for 25K prize?Seems a bit shameful to me but maybe i’m just being my old cynical self.  Thought you’d have a good perspective for me.…

        1. awaldstein

          Hi LeighI gave it a quick glance.( On vacation this week.)At first blush, seemingly smart for them.Big brands have always had ‘Blue Ocean’ blindness and they are using the entrepreneurial space as that blue ocean in the same way that fashion brands photograph the street looking for an eye they don’t have.On second blush, big shame on them. $25K! Please.Have they learned nothing from watching the leadership of the incubators and how incubators like smart companies realize they have to make themselves attractive?The entrepreneur, just like the rock star candidate, is in the center of the world not the brands.So…I wouldn’t play nor would I recommend to play. I would use the word ‘clueless’ as much as ‘shameless.Thanks for bringing this to my attention.

      2. Aaron Klein

        Thanks Arnold, you are too kind.

    6. Donna Brewington White

      Even though I am a huge fan, I confess that it has been a while since I logged on — until a few minutes ago.  I can’t believe how many changes you have made and how great the UI/UX is!  (Edit: Well, actually I do believe it — figure of speech.)Sight unseen I knew this would be a wonderful product because you are behind it.  I understand what Fred means about investing in the team.

  40. Richard

    My first venture (not including my high school flea market days of selling previous seasons womens shoes) took place during my sophmore  year at college. I was on spring break on the beach watching people struggle to put on tanning lotion. Im an invention a day type of guy and started sketching a suntan lotion applicator with a telescoping handle. I called a machine shop and sold him on the idea. I negotited a deal where  i would pay 3x the quoted price if the applicator got funding. I got on the phone and somehow got a leading suntan lotion company interested. I worked on the prototype (i was a engineering undergrad) and after a few months shipped it off. Unfortunately,  the very next week, completly out of the blue, I woke up in extreme pain,  went to the ER and was diagnosed with Cancer. The “Tanfastic” never went any further bud it did help me land my first job out of college, building  stealth composite aircrafts. 

    1. sigmaalgebra

      Now, now!  The people really interested in sun tan lotion are young women, and the means of application they prefer is a boyfriend!  Boyfriends like it, too!One of the memories I’ll never forget is the day my naturally blond, beautiful, and mature beyond belief 13 year old girlfriend said  “Excuse me”, disappeared alone into her bedroom, soon reappeared in her bathing suit with a bottle of suntan lotion, and wanted me to apply it.As I learned later, “Always look for the hidden agenda.” and “Youth is such a wonderful time of life. Too bad it’s wasted on young people.”.

      1. Richard

        Yes, it was a dopey idea. It was designed for the single girl and not necesarily to be used by yourself. It looked like a large paint brush. That said, it was fun asking single women on the beach to give me feed back on it.

        1. sigmaalgebra

          So, let me get this straight!  The idea is to have the girl and/or her boyfriend spend money, that might have been spend on a movie, popcorn, beer, etc., for a paint brush to be used instead of the boy’s two hands? 

          1. Richard

            No. It was a Point of Sale single use. Lower cost vs bottle but higher margin.

  41. Anne Libby

    I won’t besmirch fun Friday with the story from a hairy turnaround that taught me the value of asking people to tell me the often-repeated stories.When people will share their myths and legends, you can pick up a lot about culture.   (Both positive, and not so much.)Stories are important!   I hope you’ll do more on this topic.

  42. JLM

    When you build high rise office buildings you invest your entire body and soul in them.  They become you.  You don’t see a building — you see the substructure, the foundation, the structure, the skin, the systems (elec, mech, HVAC, plg, elevators), the finishes.You go to the quarry in Italy or Mexico and pick out the stone that will skin that beauty.  You are seduced by the lobby.  You are creating life.  You are playing God.  Which by the way, is a very, very good gig.You can’t wait to convert the drawings into reality.  You work with people who possess real genius.  But only you make the final decisions.Then one day, it is finished and you breathe life into it and it lives.  Then you give it away to others.  And they tell you how well you have done.  But you already know you have done your best.If you have done your job well, you are drained like having spent the night with Catherine Deneuve or having run a marathon.  I like the Catherine Deneuve analogy better.You own that memory and it becomes part of your DNA and when next you do it again, you are better at it than ever before.You have planted a tree, fathered a child, been to war and survived and changed a down town in an irreversible way.  That is life.  Real living.So I had just finished the best building (One American Center in Austin, TX) I had ever been associated with, with a fabulous architect (Gene Aubry and John Smart) and had built it in record time.  I had rejected the first 7 designs before picking the final one.  Gene later said I had forced him to do his very best work.  That was quite a compliment for he had worked for years with Philip Johnson.We had Pres Ford at the grand opening.It was a moment of triumph and I was totally drained.I had a cup of coffee with one of my colleagues ostensibly to chat about the future of the firm and innocently asked how I fit into that future.  He insensitively said:  “I’m not sure you do.” Ugly, spiteful, jealous comment at my moment of triumph bursting my bubble completely.An hour later, I was no longer a member of that firm.  I was headed to the south of France and spent the next 3 months in Cape d’Antibes (Hotel du Cap, John Kennedy and Jackie O suite), Monte Carlo (Monte Carlo Beach Hotel in the Eva Peron suite), Nice (Carlton Hotel).Ran 10 miles a day.  Gambled until 4:00 AM.  Rose at 2:00 PM.  The $$$ was strong as horseradish.I came home by way of Paris and London and the QE II.  Sat at the Captain’s table so he could ogle my beautiful wife.When I got home, I hung out my own shingle.Funny thing is I loved the guy I had worked for and he was literally the best deal guy I ever met.  He treated me like a Prince.  He let me build buildings you could only dream about.  I would still be working for him today.One insensitive slip by another fellow and I was in business for myself.  What a lucky thing.

    1. Patrick Campi

      Great story. Love the design it, build it, with passion aspect. My micro version is I’d been hunting for space here in NYC to open a cocktail lounge in the West Village 15 years before it became the most expensive zip in the City. My 6 year search led me to a new building with bare bones. I built from cinder block scratch to what eventually was featured in Interior Design and  The Book “100 of the Worlds Best Bars”. It was always “why can’t we do this..? Why can’t we do that…? two businesses later and I’m now teamed with some great tech buddies and we’re tackling a huge issue with small business and the burdensome costs of credit card processing. Big pain for small business… but we have a solution that is not being focused on by the big players. The answer is “we CAN do this” and it’s about to happen…

      1. JLM

        The creative building process is one of the greatest rushes in the world — from nothing to something.Even better when it houses a business which is an extension of the creativity.Wow, one of the world’s 100 best bars?  No kidding?That is huge — maybe an entire week with Catharine Deneauve?I also renovated old office buildings which in their way were a different and sometimes better undertaking.Here is an old 1910 building I renovated and named two different companies after.It is across the street from the other building.  It was great fun and housed Austin’s best restaurant for years.  I love it.

        1. Patrick Campi

          Ha,Thanks! I’ll take Catharine D’ anytime but I didn’t get that payout. Appreciate your comments. They are always inspiring and insightful. 

        2. Donna Brewington White

          “The creative building process is one of the greatest rushes in the world — from nothing to something.”That is how I feel about recruiting. It is not “building” per se, but it is creating something from nothing.  It is a rush!

          1. JLM

            I suspect it is also very gratifying because many CEOs do not really know what they want or need.I used a recruiter to get my last CFO and he has been a Godsend.  Literally a liberator of my time and energy and the recruiter — who did a great job of evaluating me and what I needed/wanted — spotted him as the perfect candidate.She had real vision and wisdom and convinced me of what I needed.Funny thing was he came w/ a bit of a cloud as he did not really know why he had gotten canned but I knew his former employer and I thought him a jerk.One of the most gratifying hires I have ever made and I only did two things — listen to the recruiter and pay her bill.

          2. Donna Brewington White

            I love to hear stories like that about recruiters.I imagine the reason you could just “listen to the recruiter” is that she first of all listened to you, really listened.And, yes, meeting the need, finding the solution, especially when this involves skill in consultatively helping to define the need…and making a CEO’s life easier…is extremely gratifying.    

        3. William Mougayar

          I saw that building JLM built as he showed it to me with a twinkle in his eye just a few days ago, and I’ll attest it was the most beautiful office building in Austin. Actually, it made the downtown & gives Austin a big city feeling.(JLM- pls do me a favor and stop misspelling Catherine Deneuve’s name. It pained me to see it misspelled 3 times)Son of a gun, we’ll trade stories about the French riviera & Monte Carlo at another brunch.

          1. JLM

            Ouch, corrected my mis-spelling.  Sorry and thanks.

          2. William Mougayar

            I think she will be pleased ! Thx

          3. Donna Brewington White

            “Son of a gun”?Ha!  Now I know you’ve been to Texas!

          4. William Mougayar

            It deserves a Rohanesque Ha Ha Ha.

        4. fredwilson

          another handsome structure

    2. fredwilson

      i believe i’ve been in that building. it is an awesome structure.great startup story.

    3. DonRyan

      You seriously need to write a book. So awesome. 

    4. Mark Essel

      That’s a mighty fine palace of a building. Impressive.Glad to hear you got motivated by a sideways comment. Finding one’s calling and seeking their way is irresistibly nonlinear.

  43. Daniel Cole

    Urban living in Baltimore wasn’t working with young kiddo’s, moved to our first single family home and immediately dropped $3K on power tools.  I had to figure out a way to rent tools inexpensively from others in my community. Nothing existed, so built it. ToolSpinner should be live this month in our beta.It’s been a thrilling ride and we are just getting started, looking forward to the next 3-5 years.

    1. Richard

      Awesome, add high end kitchen appliances, mixers, juicers etc.

      1. Daniel Cole

        Thanks Rich. We’re focusing on the general tool rental market which is $9B. That should keep us plenty busy. You get a very different set of concerns with appliances vs chainsaws.

    2. JLM

      Add delivery and pickup plus consumables and you’ve got a winner.  Also a bit of instruction which already exists on YouTube.I am an inveterate tinkerer and have for years bought contractor quality used tools on Craigslist.  They are very inexpensive.

      1. Daniel Cole

         Thanks JLM, we are still figuring out how to treat tools with higher or more expensive consumables such as a tile saw. The whole idea of the site is allowing everyday homeowners to rent their idle tools.Post-funding we have plans for a whole line of safety/instructional videos for each tool category. Can’t wait. Right now we are just in proof of concept stage.Transportation is agreed to between owners/renters. We wanted to keep this as scalable as possible.

        1. JLM

          You don’t need to worry about the videos.  They are out there already.You’ve got a winner.Testimonials.The consumables are a huge opportunity.  A table saw is just a table saw but when you put a 120 tooth blade on it, it is magic.

  44. JLM

    Wow, talk about some highs and lows — Spring Break, cancer and stealth composite aircraft.Glad you licked the cancer, my friend.  Well played!

  45. JLM

    Brilliant strategy.  Well played!  Much success to you.

  46. Kern Patton

    My startup story is still being written, but reading the comments and the post gives me hope, at least I don’t feel completely insane. 

  47. JLM

    Teach them to swim when they are 2 or less, it may save their lives.Tire the crap out of them every day by letting them exercise and play.Don’t ever put them in Oshkosh overalls.  It will haunt them when they grow up.  If you buy them a sailor suit they will grow to hate you.Take pictures, videos — because 20 years from now that will give you great pleasure.Enjoy the little rascals because the time will fly by like a whirlwind and then they will be bankers in Phoenix.

    1. fredwilson

      when i was at MIT you could not graduate if you did know how to swim

      1. Elia Freedman

        That’s really cool. I wonder what inspired that requirement?

  48. brmore

    Hated my job and wife said “Ok … sigh”, although not necessarily in that order.

  49. Elia Freedman

    The year was 1997. I was a senior in college, majoring in accounting, wishing I had majored in CS. I worked in accounting the previous couple of summers and really didn’t want to do that for a living so tried to find some development work. A friend was working for a publisher who was taking shareware Newton titles and publishing them for retail. This thing called a Pilot just came out a few months before, he wanted to have some titles for it and I said why not. I’d get experience and if lucky pay off my student loans. He gave me a Pilot 1000 and I fell in love. The idea of carrying a computer in my pocket was mind-blowing.It took me months to write my first title — a hybrid calculator/spreadsheet that took advantage of the PalmPilot’s bigger (than any calculator’s) screen — but the publisher was playing games with me and tried to rip my friend off. We quit to start our own thing. Infinity Softworks was born. My friend left after a year but here I am 15 years later. (I’ll move on when I solve the problem I set out to fix.)

    1. fredwilson

      what is that?

      1. Elia Freedman

        We have the Internet, always on connections, touch devices we carry in our pockets and amazing amounts of computing horsepower but we are still working with numbers the same way we did in 1979.

        1. fredwilson

          got it. big idea.

          1. Elia Freedman

            Thanks! Been refining the intro since I emailed you. Also working on an actual demo I can put in your hands but paying the bills keeps getting in the way. (Almost done with two major projects and then can get back to the real fun.) I’m really curious what you think.

          2. fredwilson

            i understand

  50. Dave W Baldwin

    Mine started with a pancreatic operation… the drinking came later.

    1. fredwilson


      1. Dave W Baldwin

        The surgery or hangover?

  51. Patrick Dugan

    I was unhappy with my job in Vostu so I cold emailed Net Jacobsson who I had read about in an Inside Social Games article and we started working together on a game for – a year later our start-up plants hadn’t panned out, and we were waiting on a big money deal to do a Kardashian game. We got the sense after a few months of negotiation that the deal was bogus and I decided I wanted to employ my powers for good; use game design to solve the marketing problem of sustainably produced, real food instead of Sears’ Kardashian line. I had been talking with an indie developer named John Harris who was thinking about a farming game as one of his long-standing game ideas, and we started prototyping at the end of September 2011. That’s how Real Filling started. 

    1. fredwilson

      how’s it going?

      1. Patrick Dugan

        Good! I’m boot-strapping and maybe 6-weeks from Alpha. Aiming for a Q3 launch. 

  52. Mark Essel

    I was at work feeling frustrated and powerless in a meeting. I was given a task list by a tech supervisor who was on a phone call with one of our customers. I handed him the list back, saying something like “I can’t fucking do this anymore, I quit”.A few weeks later I bumped into Seth’s blog, then AVC and discovered the world of startups and disruptive marketing. It took another several months before I swallowed my pride and took a part time job at my old shop – my boss made my leave – a leave of absence. I haven’t stopped studying and experimenting since then.I’ve gotten the chance to work with some great builders since then, doing my own thing and collaborating with others.

  53. jimmystone

    Great post. Thanks for sharing.

  54. Robert Thuston

    On the Appalachian Trail in high school, “this thing runs from Maine to Geogia” outdoor director. “I can do that” me. “no you can’t”.1 year later… Meet a guy for the first time in college who does a bit of hiking… after a few drinks (we don’t even know each other)… “hey, let’s hike the AT when we graduate… He becomes a good friend, we joke around about it for 3 years.Junior year… I’m enthralled by the book Into the Wild, “I want my own raw first hand experiences”. I get into Dharma Bums by Jack Kerovak, and read a Walk in the Wood by Bill Bryson as well, which adds to it.Senior Year… the joking turns into “let’s really do it”. I would make a small commitment, “hey, I just bought a trail book on the AT”… Him, “hey, I just bought a pair of new hiking shoes”…into “hey, I just bought a train ticket to New Hampshire, and a bus ticket to Maine”… Next thing we know we’re on our way… And 5 months later we’re back in Georgia with 3 inch beards, having met some wonderful people, seen some great places – 2200 miles through 14 states.It ain’t a start up : ) but the whole time it had those roller coasters… “can we do this? Are we going to make it?”… You had the humps, the valleys, the “I want to go home” days, as well as the “I cannot believe I’m doing this, what an amazing experience” days – nobody hiked your miles for you, and no matter how fit you got – putting in 20 + mile days one after took effort.

    1. JLM

      Well played!The Appalachian Trail end to end is an unbelievable accomplishment.  World class.  The piece de resistance!I regularly hike a bit of it in the Smokies but I can’t quite screw up my courage to go for the whole enchilada.Did you ever seriously consider quitting?Next year in Jerusalem.

      1. Robert Thuston

        Thought about it. Started with 2 friends. I was the only one that finished. It wears on you mentally and physically. There are days you think, “maybe I’ll break my foot today, and be able to rest for the next couple of months”.The lesson I learned though was… keep hiking… that stuff passes. And inevitably, the next day i would find my grounding and realign with why I was doing it.

        1. JLM

          You have a strong mind.  Persistence is the secret to success.  Well played!

  55. Jay Parkhill

    I was an associate at a law firm in Silicon Valley and feeling bored doing the same transactions repeatedly. I looked around at a lot of possible job options (favorite memory – me to a VC contact in 2005 “I find this social networking stuff quite interesting”. Him in a dubious tone: “well… there’s Facebook…”).Finally I decided it would be more fun to work for myself, so I quit my job with $0 business of my own and a family to support. It took a long time to build a strong client base but 6 years later it is working out well. Leaving a salaried job to start your own business feels like being on a tightrope without a net below you. In the down periods my stomach clenches and and I can’t eat, but in the good times knowing that you built a business from scratch is the best feeling in the world.

    1. markslater

      well done. congrats.  

  56. ShanaC

    I grew up in a family of Entrepnuers.  A lot of them. My stories about what I am starting arne’t interesting so much (and not far enough along) – but some of my family stories have played themselves out well.Here’s one.My father’s first cousin actually started three business.  His second and third ones were very interesting.His second business was a major tex-mex restaurant in california during the40s-50s. His chef at the time introduced him to thing known as guacamole.  The restaurant was doing fine, but he was getting bored, and he really loved guacamole, and wanted to know what was in it.  In the process, he discovered Avocados, which at the time weren’t really available in most areas of the country (and he should know, his aunt, my grandmother, married into what was at the time one of the largest produce distributors in the US).He decided that because he loved avocados so much, and guacamole so much, that he was going to sell his restaurant and buy a large farm.  His large farm would do nothing besides grow Avocados.  He did this, and he helped make avocados (and guacamole) popular and became extremely wealthy.Opportunities are everywhere, and the stories of how things we think are ubiquitous should hopefully make us realize that there are opportunies to make the non-ubiquitous, ubiquitous

    1. fredwilson

      my son thanks him!

      1. ShanaC

        I honestly wish he could do so in person – unfortunately, this person is dead.I will say having lots* of stories like that in your own family helps make entrepreneurship normalized*By lots, I mean lots. I have a bizarre family that way.

    2. Donna Brewington White

      Great closing comment, Shana.BTW, I never had an avocado until I became an adult, after I moved to Los Angeles. Love avocados.  Just reading this set off a craving.

      1. ShanaC

        Well, its true – see now avocados are ubiquitous, especially in urban areas, and guacamole can be bought in supermarkets for the superbowl, but we’ve forgotten that at one point in fairly recent history it wasn’t so. Same thing with computing, or the internet, or many other things we interact with.Though on a more serious note: don’t hold up this person as a paradigm – he definitely had his issues.

      2. JLM

        I would bounce a basketball through a mine field for some really good guacamole.Spicy, fresh, with just a tad more lime juice than allowed by law.

        1. Donna Brewington White

          Ha — just picked up some from Whole Foods. Thanks to Shana and maybe her uncle. Sent via mobile

          1. ShanaC

            my first cousin once removed

    3. Ben LeBlanc

      Love the chain of events there and getting down to something so specific because it’s what he loved.

  57. K_Berger

    Not sure you can call my first story a startup, but after interning for an options trader in the OEX pit at the CBOE, I started trading on my own (lots of butterfly spreads).  This was in 1992, before anyone with a computer could be a day trader.  I wasn’t very good at it and got out after 6 months, but it was an experience to be part of that open outcry pit, pretty much gone now.  Pre-87, when people didn’t really know how to price options, was a great time there. I always held a small bundle of out-of-the-market puts at a 1/16, just in case.I am not the founder of our current business, but I invest so much time and energy here running it that I almost feel like I am.  Too make a long story short, the founder owned nursing homes and got into some legal trouble that she really didn’t deserve.  To deal with it, she needed to have better quality education and a better way to do the record-keeping.  (Believe it or not, most nursing homes still track their legally required training by keeping signed pieces of paper in a binder.  And yes, it often gets lost.  Really.)  So, she found some friends, developed some nice PowerPoint training courses, and had a simple database built to deliver the courses online.  She saw great success and had a neighbor who also owned nursing homes.  Together, they bootstrapped the company, made everything a whole lot better, and took it to market at the end of 2005.  Since then we have been growing consistenly, both in customers and profitability.Despite all the bad press that nursing homes get, there are a lot of dedicated people in that industry.  It is a very rewarding experience to have a product that really improves the quality of the care the residents receive, that brings technology to an industry that badly needs it, and that you can make money doing it.  It is also a true lemonade-from-lemons story because the same government agency that got her in trouble in the first place now recognizes her as a pioneer in improving long term care.

  58. Smithy

    awesome post and stories.alas, ive never been a founder ..just a joiner ..3 startups over the years and 2 bigcos. currently have an amazing job at a bigco ..but still something missing.funny thing – over the past couple of years a few years ive made some new friends, who, i have a sneaky feeling, will someday become co-founders..

  59. markslater

    the irony of this blog is thats its distracting me from building my start up!

    1. fredwilson

      that’s a feature not a bug

      1. markslater

        very true!

      2. CynthiaSchames


  60. Anon

    I’m writing it as we speak, here’s the generic version:1)  Oversaw audience monetization at a large publisher with a need to generate new sources of revenue.2)  Team stumbled upon a new revenue source for publishers3)  Made a lot of mistakes setting it up, huge problems and lack of transparency in current market players.4)  Saw a new to approach the market to fix these problems5)  Wanted to build at our previous Co, but disagreement with founders over strategy and vision leads to creating a 3rd party platform.Nothing unique here, but having lots of fun…

    1. fredwilson

      the job thing….

  61. Givengi

    Well, I was 14 when I started my first company and I didn’t have much of a choice! We had run a school fundraiser and contracted with a company to help us, said company didn’t pull through and we were left hanging. I really wanted to go to go on this trip to DC, and wanted the experience. I had saved up money over the summer working for my brother’s dad fixing up houses, I just tore stuff down, didn’t do any actual construction. It only took about $1800 to seed it and with the help of my peers, it grew into a $100,000 annual rev company before I was 18. Most entrepreneurs have a lot more experience before they start their companies, thankfully I had a Mother who had set out on her at a young age (23) and started up a restaurant chain. I wasn’t about ready to leave my fate and the fate of my peers in the hands of some slimy guy who took our money and ran – so we did what any entrepreneur would do. Create our future.PS – this is my first visit to this blog, I love all these awesome stories! 

    1. fredwilson

      please come back and share your thoughts more often!

  62. Matt Straz

    My story is unusual.I was a fine arts student in college and unfortunately became very ill. For four years I was completely home bound. I was very poor and on welfare but managed to get a Mac and self taught myself how to design and code from my bed. The web was just getting going so I started a web design company. I did most of my meetings via phone and email because I was too weak to leave the house. When I did a meeting in person I had to take taxis because my driver’s license had expired. Starting and running a business this way was difficult.Thankfully, my health eventually began to improve. I eventually expanded the company to 40 people. We developed ecomm sites. Then the company was sold to the world’s largest advertising agency where I worked for 7 years.Then I left to co-found Pictela which was sold to AOL. Now I’m doing Namely.I consider startups to be life affirming.

    1. LE

      That’s an amazing story Matt. Really impressive what you did and especially given the circumstances.

    2. JLM

      With the long catalog of obstacles to success, you confronted and overcome a most unusual one, indeed.Well played and glad to see you are healthy again!

    3. fredwilson

      serial entrepreneur and self taught coder. two things i have great appreciation for.

  63. jerrycolonna

    That dinner changed my life–for the much better. Thanks to The Gotham Gal for making that happen. 

    1. JLM

      Haha, there is nothing so sweet as having a legendary tale confirmed by another participant.LIke finding out the damn fish really was that freakin’ big.So, you really cut the deal w/ the GG.Well played and oh so sweet.Life is good and its adventures are even better.  Spread the news!

      1. jerrycolonna

        The story is absolutely true. Fred and Joanne came to our town and we ate at a Middle Eastern restaurant.Mark Pincus’ insight–that Fred and I should be partners–was brilliant and I’m forever grateful to him for pushing the thought.

        1. fredwilson

          is that restaurant still around?

          1. jerrycolonna

             Yep. Ayhan’s Shish Kebab…one of Port Washington’s more famous places. 😉

          2. Dasher

            Wow! Great story behind the place. Will check it out.

  64. laurie kalmanson

    not quite a startup story; but here’s my consulting/freelance story:  after working in agencies and startups in nyc, i was pregnant and on bedrest when a friend of a friend called with a pitch. it was awesome. it was huge. we totally clicked. the kicker: i was on bedrest. so i put together a tag team and worked remote until i was able to work onsite. 10 years later, my daughter now closer to middle school than to preschool,  i’ve had more engagements, clients and fun than i could have imagined then, and i’ve never looked back.

  65. Esayas Gebremedhin

    Nice story Fred. I have an extract story from our “Infinite Game”:6 month ago I met Nils at the coast of rhein, which is a river in Cologne. We have never been to this place before. Nils is an old friend and class mate of mine from Macromedia. He was sitting next to me in 2002. Nils and I were very different. He listens to Gothic, I listen to Hip Hop. But we had one thing in common from the very beginning: We always created stuff which is mind blowing. So after I had upgraded my studies with Applied Imagination (a course that Steve Jobs would have dreamed about) I had this great insight that our potential would be more valuable if we kick-started a business. Last year on a sunny day we were looking at the river and I made him an offer to join our team. It was like those scenes in movies where you go to jail to get the sharpest and most brutal criminal out of jail to fight other bad boys. And yes Nils is a prisoner in a company that just sells his ingenuity for a fraction of his potential. Yesterday we found a way how he can escape from the prison to tackle real bad boys – lol.

  66. Guest

    I can’t wait to read all of these tonight, but I’ll add my short version to the pile now for entertainment’s sake.  It was 2009.  I had been working in fashion in NYC for many years and my spirit was slowly rotting away in a trendy dress in a cubical.  I kept a 3×3 vision board in said cubical of what my life looked like when I was my own boss.  People thought, and rightly so, that I was crazy.  I kept a small notebook of ideas of companies I’d like to start ranging from juice bars to airport travel accessories.  Then out of left field my boyfriend of several years dumps me.  Ouch.  Not my best year.  So long wedding planning, hello vicious world of NYC singledom.  One night while visiting my mom in MS I had a dream that I was selling all of my ex’s stuff and telling the story behind each item.  My laughter woke me up.  I told my mom and she advised that I burn my notebook and get to work on this. I did and my ex thought it was so brilliant he offered to fund it.  It took a while to get off the ground, but finally it came together.  I sold a couple of things, including a fork from PJ Clarks and got offered a reality TV show.  Go figure.  My friends started to post clothes on the site and started to call me to ask if they could sell their closets and make up a story.  It became a market-place for clothing, and considering my background it shouldn’t have been a surprise.  I went back and re-read a few things our favorite bartender posted on AVC and Closet Groupie was born. Life has a funny way of bringing you around to what you are supposed to be doing and with the people you are supposed to be doing it with!   That’s the short/ PG rated version of the story.    

    1. fredwilson

      that’s a good one Kelly.

    2. Donna Brewington White

      Love this story, Kelly!  Heard the abbreviated version at Punch’s…good to hear more.BTW, Cheeky now has two fewer items in her closet and I am one happy camper.  😉

      1. Guest

        I love that Valentino skirt.  Great taste.  🙂  Cheeky actually lives quite close to you and I’ve taken a thing or two from her closet as well… maybe the next time we meet up we will both sport our stuff from her closet!  

  67. Dan Conway

    Late 2004.I had been at the same firm for eleven years.  In the year I joined it was Shearson Lehman Brothers.   I had seen a great market and then survived the dot-com bubble.  Loved my clients and loved managing money. There had been good timeswith the firm and I had made a lot of great friends but more and more I beganto distrust the decisions being made within the organization. And there seemedto be a lack of values.   It was discouraging.  I knew I wanted to go and began to keep a file inside my desk.  Across thetop I had scribbled “Why I Left”.  Every day, the sales manager would hand out sales sheets or bibles for new complex products for us to bring to our clients that had been created in New York.  If I thought it was a bullshit I would throw it into my “Why I Left” folder.   That folder became the fuel in my car’s gas tank in the months preceding my resignation.   I could see what the firm was and hold it up to and against who I was and what I wanted to be doing.Sandy Weill had at some point come in and had spoken to our team in-depth of the tales of his career and all the “great opportunities” we had in the business.   I took notes while he talked.  He told of how he had gone from Bear Stearns to Bergman and Company andthen….and it’s the one thing I circled three times: “We started a business.”    Thatwas the great opportunity he had gone for and was talking about. Those notes made it to the front of the “Why I Left” file.I soon knew I wanted to go about doing the same but had to wrap my head around what thatwould entail and the possible risks involved for our family of six.   But it became clear that the real risk was staying.  I was miserable there and I loved the idea of running my own show.I was fortunate in that I had come about some wonderful clients over the years who I believed I had always done the right thing for, who I had fun with, who I believed were inbusiness with me…. not because I was at such and such firm.  I had always marched to my own drum.  I had protected them and a good number had enjoyed seeing done well for over the years.   Amongst the group were some entertainment people, some great retirees who never ceased in getting me to laugh and a few dotcom executives who I had helped walked through doing the right thing with stock options in late 1999 and early 2000.  It was terrifying and exhilarating.  My plan had been to quietly resign after the close of the market and just before the office Christmas party on December 17, 2004 but somehow the government’s computer system notified my old firm of my new RIA registration and I got a 5 a.m. call at home from my branch manager.   I ended up faxing in my resignation, went in, said a quick “thank you for everything” and was gone.They were surprised.  Not because I left but because of over the sixty brokers that had left during my years there, I was the only one to leave to open up their own shop.   All of the others had just switched firms to pick up a check.

    1. Patrick Campi

       “I had always marched to my own drum”… the soul of entrepreneurship!

  68. LE

    I got the idea after graduation to start a computer supplies business so I went to talk to my father’s friend  who owned a printing company (I needed a printed catalog). It turned into an interview. But then he said something like “you’re a bright guy but you don’t know printing” so he didn’t want to hire me. But he let me spend a half day in his plant and I watched and asked a ton of questions and it really seemed easy to me.  I always did “ok” in school but I have more of a knack for reverse engineering and figuring things out based on limited info. So I thought I would start a printing company and then somehow segue into computer supplies after making some money.I started with about $2000 (earned by doing photography in school) and began to outsource the work until I had enough business to justify buying my own equipment (some of which was financed with bank loans and leases I think at 15% interest if I remember correctly).I was doing very well (my best year ever was the year I sold – everyone thought I was nuts) but I was bored and no longer enjoyed what I did. At the time I sold (9 years later) there were 17 employees.  The business is still operating today.One of the things I did at that business was buy a Unix multiuser system (my cost $40,000 in 80’s dollars)  and I wrote some estimating systems for the business. (I got the computer wholesale by posing as a reseller.)  We had Wyse terminals on everyone’s desk and I wired and setup and maintained the entire system. Back then there was a bound set of manuals.  As a result when the Internet came along I had the background to do what I do now.

    1. fredwilson

      what was the first domain you bought?

      1. LE

        First domain I bought was probably my last name.   One of the early 3 letter domains I picked up was company approached me (1999?) which was funded by KPCB. They offered $30,000 (I think),  $70,000 and then $100,000 which I turned down. (I had just sold another name for $250,000 and I think had tried to get either $170k or $200k for bbo) On the $250k deal I had them so lathered up I got $50,000 just to hold the name for a weekend so their board could approve. That’s right. $50,000 for an option to hold a name. Picked up the check at their lawyer in Philly and didn’t have to sign anything.)Back to After the 100k the guy negotiating was basically like “deals off forget it”. And he meant it I could hear it in his voice.I went to bed that night and thought “what are you fucking nuts”. I couldn’t sleep that night (you’ve been there I know..)The next morning I called ready to “try” to get the $100k. The minute he picked up the phone I could smell the fear in his voice. (He must have also had a bad night). So I changed course and said $150,000 and he said “ok” and I had the money within a short period of time. This is that company. They are no longer around:SOMETIMES STAR POWER JUST ISN’T enough. With one of the best pedigrees in Silicon Valley, Broadband Office was poised to become the next big technology celebrity. Nurtured by Kleiner Perkins under the tutelage of two of its top venture capitalists, Vinod Khosla and Kevin Compton, BBO was going to be an all-in-one provider of phone and Internet access, topped with a range of services — like Web hosting and software to automate human-resources tasks. But after two short years, Broadband Office is running out of cash, offering a lesson in humility. No matter how much a company has going for it — big backers, big partners, big budget — it can still miss the mark. Several people close to the company say BBO’s problems go beyond the economic downturn…

        1. fredwilson

          my last nameof coursei blew thatwe own solomonwilson.comthat’s the gotham gal’s maiden name and mine

  69. Cost2Drive

    Here’s kind of a fun story related to our startup (and actually ties to a questions posed by one of the comments on the Startup Curve post about the initial traffic spike).We’d just launched our site and you could hear the crickets chirp..very little happening.  A PC technician comes to my house to fix my wife’s PC and sees a powerpoint slide with the company name. He asked my wife “what’s that?” and when she tells him he says “Cool, mind if I put it on StumbleUpon?”.Neither she nor I had ever heard of StumbleUpon so she says sure.  A few days later we were getting 25K visits a day. 

    1. fredwilson

      stumbleupon is the number one referring source for this blogonly thing that is more is direct traffic

  70. kirklove

    Having a great partner who believes in you and tells you to go for it is such an awesome feeling. You’ve got a great one in GG.

    1. fredwilson

      that’s for sure. you do too.

  71. Adam B.

    I was in Argentina working for a VC company and was asked to play polo.. i have hated horses all of my life.. but I wanted to close the deal so I sacked up and agreed to go. The night before I was talking to myself about being strong and not having fear as horses can sense it. I was ready. The following day we arrived at the polo grounds and the barn boy showed me the horse I was to mount – I lept on. Reins and polo mallet in hand and  i was ready to rock and roll. I wanted to show the horse I was strong and not afraid so i gave him a kick and off we went. Boy was I wrong. Horse knew I was a failure of a rider and ran me into a tree within 90 seconds. This was the ONLY tree on the compound. After hitting the ground I had an idea and immediately starting writing it down after catching the horse. The idea took off and the product is now sold around the world. Not a conventional story, but it is my most memorable startup story.

    1. Dave Pinsen

      What’s the idea/product?

      1. Adam B.

         I didn’t post to plug the product/biz, but it is all made in the USA. Travel gear.

    2. fredwilson

      there’s been a few startup stories in this thread based on falls/injuries. who knew?

  72. Luke Chamberlin

    I started my first business when I was five or six. There was a big construction project down the road from our house and crews of construction workers would sit out front and eat lunch. I got my mum to buy a case of Jolt Cola from the supermarket and take me down there to resell the soda during the workers’ lunch break (I have no idea how I calculated my markup). I sold out and did that once per week for the duration of the construction project.Decades later I realize that the construction workers were probably happier to see my exceptionally attractive young mother than five-year-old me, but it was a huge boost in confidence at the time. While other kids got allowances I always had to earn my money and that’s stuck with me.

    1. fredwilson

      i never had that urge to do business as a young person. but the gotham gal has tons of stories like this about her childhood

  73. kidmercury

    2005. i was working at a currency broker and was given free reign to revamp their online learning division because it was failing and because upper management thought it would be a good project for me. i was able to turn it around, and thought i should do this as a startup and apply it to many niches. a friend of mine had been pitching me on business ideas for a while because he wanted to start a business and thought i had skills complementary to him. i quit and started working full-time on my startup in 2006. progress has been frustrating, and slow, especially after my cofounder quit in 2009. but the vision keeps getting clearer and clearer, so i figure so long as the vision keeps coming and so long as i can pay the bills and save a bit, i’ll keep plugging away. unless some other company with more financial muscle lets me pursue my dream of solving poverty by rebuilding the world’s money supply with virtual currencies introduced through game-based learning communities. 

    1. fredwilson

      big vision. hard to know where to start when its that big.

      1. kidmercury

        i’ve got the initial product, users, and revenue, i just need to make it more efficient so that i get more money out of it. same challenge for the past three years. i remain optimistic that i can do it, though. or maybe i’m just delusional! 🙂

  74. Ben LeBlanc

    My favorite startup story is my brother’s, which is a touch long, but it’s better framed from the beginning.After three semesters as a pre-med student, he remembered that he couldn’t stand the sight of blood, so changed his major to business. A close friend of his convinced him to start a record label with him in New Orleans, and they were going to produce rap, hip hop, and jazz acts. It was an interesting call for this former homecoming king, golden child, and everybody’s all American who had absolutely NO rhythm whatsoever. None. (Still doesn’t). They produced a couple of good acts, but lo and behold, it wasn’t paying the bills. So they leveraged the street team they had built to promote their concerts and began promoting parties and events at bars. This became a significant part of their business, but his partner left, and the music business began to fade away, except for one alternative rock band that held a ton of promise. He poured his heart into managing the band and drove a tour van across the country promoting them incessantly.  The band was getting some great exposure and seemed to be on the cusp of landing a record deal from a major label. Then one day, the band abruptly fired him. They had planned a coup of sorts, and he never saw it coming. Fortunately, he still had the other part of his business, which morphed into event planning, party promoting, product launches, producing fashion shows, etc, and it was quite successful. Then, on August 29, 2005, Hurricane Katrina hit New Orleans. Later that day, the levees failed, leaving the city completely devastated. With the loss of life that occurred in the aftermath, he was fortunate to only lose his business. But that business was totally wiped out. No clients throwing events. No people to attend events. No places to host events.It was a time of great turmoil, to say the least. He couldn’t decide whether to stay in New Orleans and rebuild his business, or move somewhere else to start a new life. Many people were having that same conversation. Not to mention, would there even be a New Orleans to stay in? If so, would it be the same City that Care Forgot? He was pretty close to packing it up and moving up to New York. But, he committed to staying and helping rebuild New Orleans. He and a friend decided that others who were staying needed a place to relax and unwind from all the stress of those months immediately following the storm. They planned to open a higher-end bar/lounge/club, combining some elements of places you’d find in NYC and L.A. but that would still appeal to locals. This was totally different than anything that existed in NOLA at that time, so there was no idea if people would like it. Plus, were there enough people there anyway to support it? And were they going to pay a little more for a drink than they were used to, or even order a bottle? This was a risky proposition, to say the least. Fortunately, it was a smash, and Republic became one of the most popular bars in the city. It was just what New Orleans needed at the time. He was out constantly, helping everyone have a good time. He became an ambassador for the city, welcoming all those who moved to New Orleans in the aftermath with open arms (and a shot of Jack). He’s since created a mini-empire, and has three great restaurants – Capdeville, Sylvain, Ste. Marie – in his portfolio (for now).The guts that it took to make that call, to place that bet on the city that hadn’t yet begun rebuilding because it was still drying, who’s population dwindled to nothing and may not ever return, to open a more-expensive place, the type that New Orleanians had consistently rejected over the years….all of that was, and still is, mind boggling to me.And it did take some serious stones, but he had a great team, and they also had a ton of support. There was a group of entrepreneurs, some from NOLA, some not, who committed to the city and had each other’s back as they recreated a great place to live. Those people and companies – The Receivables Exchange, Trumpet Group, Naked Pizza, Entrepreneur’s Row, Launch Pad, Idea Village, and more – provided so much support to each other as they built new things and kept picking each other up if another fell down. They have created a thriving entrepreneurial scene in New Orleans and have been a major part of its renaissance and kept it a special place to be. So I guess the moral of this success story, like many others, is one of guts and community and conviction and hard work.I’d apologize for the length of this story, but I am so proud of what my brother did, and of what he and his friends helped create in New Orleans, that I could write five thousand more words on it.

    1. JLM

      Fabulous.  I will have to go to NOLA now.If it were not March Madness, I would go tom’w.You have inspired me.Well played!

      1. Ben LeBlanc

        Thank you. Not sure who you’re rooting for, but the Final Four happens to be in NOLA this year. Hopefully the stars align!

        1. JLM

          Go Heels, screw Duke.  Wonderful day, Heels win & Duke is eliminated.Life is good.

          1. Ben LeBlanc

            What an amazing day of hoops and upsets. College football is my passion, but it’s hard to top the first weekend of March Madness. What’s your over/under on the number of F bombs Coach K dropped last night?

          2. JLM

            The Rat was relieved because he knew he did not have a contender.  He was out of gas at the post game presser.I am rooting for the Heels and hate Duke but I root for Duke when the Heels are not in sight.I am looking at 57 for the O/U.

          3. fredwilson

            we are headed for a week of vacation in the snow country. we’ll be skiing snowboarding and watching a ton of college hoops. i can’t wait.

          4. Ben LeBlanc

            That’s going to be awesome. Just began my own vacation yesterday, but took a different, warmer, route. Having breakfast on a beach in Belize. Going to miss live hoops for a few days, but looking forward to catching up on my reading list.

          5. Ben LeBlanc

            Enjoy the slopes!

          6. Emily Merkle

            easy there tiger, ex-Blue Devil here…. 🙂 

    2. ShanaC

      This is an incredible story.  Just reading it makes me glad that New Orleans still exists

    3. fredwilson

      i’m not a fan of blood either. i can’t look when they draw blood from my arm. i feel like such a wimp. but i’ve always been that way.

    4. Michael Karnjanaprakorn

      Great story! I was one of the early folks that Robert took us under his wing when I first moved to New Orleans in 2007. Truly remarkable guy.

  75. FlavioGomes

    Started my first high tech venture at 22 after a bunch of years traveling and gigging in a bar band. Incidentally, negotiating with bar owners and bikers really taught me the fine art of persuasion. The money I made from gigging put me through school and after a brief stint at a large networking company, I started an isp service provider, sold that and then a software infrastructure business.I concluded that my disposition wouldn’t have been very appealing to large political enterprises. I would call a spade a spade and delivered far to many “fuck you’s” …to gain any admission to the club. Sometimes i wish i had stuck it out and held my tongue, particularly after that startup period of going through the trough of sorrow – I prefer to call it disillusionment- But that was a long time ago and I made it past that heart wrenching period…with lots of scar tissue…and never looked back. And now Im having the time of my life…so much fun…so engaging…and built a great team that inspires me everyday to be a better founder. Oh and did I say…we like beer!!! Happy Friday everyone

    1. fredwilson

      i like beer too

  76. Ross Larter

    Here is the story of how got started in a pub in Bristol, England.A friend was asking people round the table how their day was and somebody replied with a 10/10.  My response was if today was the best day ever what happens if tomorrow is the same as today but then something else amazing happens (I think it included the “pussy cat dolls”), and we chatted for a while on this.The next day I started thinking about the question and told Jake (Co-Founder) about the idea and it went from there.We both work in software development so building the site was not an issue, but we had to learn a lot of new things, looking back the tech is the easy part its all the other stuff that was hard!We are on MoodPanda version 3 at the moment. For the first 2 versions of the site we built it to track just your own mood. It was only once we added commenting and “hugs” to the current version that we realised that people wanted the interaction with each other.This was the real thing that set us apart from similar sites and is when our user based really started to grow. ross @

    1. fredwilson

      the internet is a two way medium. i am reminded of that every day

  77. Ruth BT

    Ours is not so much start up as restart. After 2 gererations and 40+ years in business in an industry based on an ecomomic model of a bygone era my husband and I passed the last of the stock on to a 3rd party to sell and walked away to start again. A small business reliant on the internet was started, we felt our way through and had some minor success.  The week we recieved payment for the last of the stock, an old friend came to us, “here is some stock – try again – on the internet, don’t pay me until it is sold”. We reengineered, for every rule we had in the past – we did the opposite – or ignored it altogether. Fast forward 5 years. We did what everyone said was undoable. We are recreating an industry – online. Everyday we push it further, take the risks nobody in the industry is willing to take and make it work. Ours is a very narrow niche but the depth is there. It’s so much fun moving in unchartered waters!

    1. fredwilson

      which industry?

      1. Ruth BT

        Black Opal from Lightning Ridge Australia. Over 95% of the worlds black opal is found within a 100 mile radius of the town.The website is relaunching next month so excuse the atrociousness of

        1. fredwilson

          wow. that is so cool. i’d like to buy a black opal for gotham gal.

          1. Ruth BT

             And I am sure she would love it! Happy to help you out anytime Fred. My email is ruth at gemfish dot com dot au.

        2. panterosa,

          I am in love – black opals are so cool. I am a moonstone and fire opal fan, not a big leap to these stone. They look to have florescence in them.

          1. Ruth BT

             Oh good moonstone is hard to pass up too. Opals are a unique phenomena as it is the light refracting back out on different sized silica spheres that give it the enormous play of colour – making it look like your own personal light show!

  78. ForestGump

    I made a friend this man named bubba while I was fighting in Vietnam. We decided to start a shrimp company after the war was over. Unfortunately he died in the war. I started the company anyway and it became a huge success. I gave half of the proceeds to Bubba’s family as it was the right thing to do.

    1. Donna Brewington White

      What’s your exit strategy, Forest?

      1. ForestGump

        I don’t take exits. I just keep running.

        1. Donna Brewington White


        2. Donna Brewington White

          Hey, no fair changing your name mid-stream.  Now the joke is not as funny.Oh well, on Dasher…!

          1. ForrestGump

            You are right.I was trying to post another comment that would be a bit silly with ForestGump as the name, so changed it to my usual nickname Dasher. For some reason the name on my previous comments changed too. I am trying to change it back with this comment. Hope this works.

    2. ShanaC


      1. Donna Brewington White

        Did you make this comment before or after “he” changed “his” name to Dasher from Forrest Gump?

        1. ShanaC


  79. Donna Brewington White

    I have always wanted to start a company.  I put the dream aside along with my business career to do something entirely different for several years.  When my husband and I resigned at the same time from the same organization, I decided to go back to recruiting and, given that I was pregnant and had a toddler and a preschooler, decided to go out on my own.  It was also my chance to pursue a dream.I can’t begin to tell you how many odds were against me…well, besides being flat broke, pregnant and with two young kids.  The internet was completely new to me and this was in the middle of the dot-com bubble.  I barely knew how to work a computer!  I learned very, very fast (and fell in love with the internet).  And I learned how to run a business, even if a very small one.  It was successful enough that within a few months, my husband could continue as a stay-at-home-dad until his career kicked off.The best part is that I was no longer just recruiting but fulfilling a vision, creating a search practice where certain standards were just taken for granted. As much as I love recruiting, it was the sense of building something that kept me going.Things really fell into place when the co-founder of a startup negotiated with me to recruit their management team, and another founder in the portfolio joined in on the arrangement.  I had a blast helping to build these teams and becoming involved well beyond just recruiting. I’ve never had so much fun.  My passion for startups was ignited during that time and the love affair has never ended. My goal was to hire people and grow my firm.  But trying to raise young children and scale a business don’t mix well.  When I was aggressively recruited by a search firm after eight years, some personal family challenges made it hard to say no.  It was hard to say yes, too, because it felt like giving up a dream.  It was a great experience, but I eventually left the firm, mainly because I saw that it was taking me further away from exercising my passion for working with startups. I am sort of “in between” working freelance while deciding whether to fully re-launch my firm now that my kids are older or to exercise this love for startups in another way.  Stay tuned…

    1. fredwilson

      maybe a partner or two would help?

      1. Donna Brewington White

        I wonder how many people’s lives you have changed by asking a simple question?Been ruminating on this one all day.  Thanks.

        1. fredwilson

          that’s how i roll. always have partners.

  80. Donna Brewington White

    I love this!!!

  81. Dave Pinsen

    OT and deleted.

  82. Jerry Maguire

    I used to work for this sport agency that represented athletes. In one of the those frustrating moments, I wrote a meme called ‘The things we think and Do not say: The future of our business’ and sent to everyone in the company. Though my coworkers liked it the management didn’t and I got fired. I decided to start my own agency, but none of my clients wanted to back me in the new company, except for this one wide receiver. He had a strange request: ‘show me the money’. He was kind of a difficult to deal with but very loyal. I was lucky to have a believer like that. Oh, there was this girl that worked for the agency that fired me that also believed me and came to work for me. She is kid of cute, so I ended up marrying her. In the end things worked out great and I became one of the top sports agents. 

    1. JLM

      Man, you should make this into a movie.  It is awesome!Maybe you could get Denzel to star in it?

      1. Jerry Maguire

        Ha ha. May be Tom Cruise 🙂

  83. Donna Brewington White

    “go for it”A new variation of “three little words.”

  84. William Mougayar

    It’s an interesting observation that some posts like this one generate comments mostly from the 20-30 AVC regulars, whereas others (eg. Yahoo’s legal crusade) see a much broader range of commenters. I think when it’s about sharing personal stories, the less regulars tend to be more timid, but when it’s a more public subject, any reader feels more compelled to comment. 

    1. fredwilson

      yup. that Yahoo! rant traveled wide and far. it’s also true that the posts that generate mostly regulars commenting generate more of a community feel. not much hostility in this thread!

      1. William Mougayar

        Both types make a good variety & the ones that are dominated by regulars serve as a showcase for civil commenting community ideals (most of the times).

  85. Gregg Freishtat

    So many stories but why not start at the beginning….  One year out of law school (1993), I was working on a really complex piece of litigation and it was a real pain in the ass to access and control and the information, data, case law, depositions, court filings, notes, etc required to run the llitigation.  They were all digital but in different systems with I/O and format issues.   It was just very natural to build a system to dip into all those systems, normalize the data, and build a “case file” that had everything I needed to run the case and save huge amounts of time.  I will never forget the conversation with my father (senior partner of the law firm) when he said, “I get it” — but also, “son, I don’t think you understand our business.  We sell hours.  This will cut our revenues by 1/3 if it works.  No one will buy it”.  He was right of course, lawyers were not ready for the efficiency the Internet could provide.  Quitting was not an option.  We morphed/pivoted (not really a word back then) into a gen one unified messaging company.  Same vision different pots of data.  CMGI ended up investing in us out of its first fund (Jerry C joined our board – thanks Jerry – and Flatiron funded my next one – Thanks Jerry/Fred) and we sold the company successfully about a year later.   Have built and sold two more start ups with the same vision and are working on number four now (Scribit & Vertical Acuity).  My lesson:  Success is the unyielding refusal to fail….

    1. fredwilson

      jerry was working with you on that one when i met him

      1. jerrycolonna

         I like to think I learned as much as you did Gregg from that first deal we did together.

  86. Dave Pinsen

    A little hesitant to add my start-up story here, because it will end in media res, but here goes.After getting my head handed to me with my modest savings in the ’08 crash, I thought about ways to crash proof an investment portfolio. I knew in general terms that an investor could hedge with options, but I couldn’t find any tool that answered a simple question: I own X shares of a stock or ETF. I can stomach a decline of Y% — but not more than that. What’s the least expensive way of protecting me against any drop bigger than that?I ran into a few dead ends trying to find someone to help me solve that. I had flirted with applying for a finance Ph.D. program at a local university a couple years earlier, so I contacted the program coordinator there who put me in touch with a ABD Ph.D. student who had worked in risk management on Wall Street before going for his Ph.D. A week after we met, he called me to apologize — he didn’t know of a way to solve the problem without having someone like him constantly rejigger a model to match reality. I told him to keep the money and let me know if he thought of someone else to contact. A few days later, he had an epiphany which was the start of the algorithm for Portfolio Armor — a solution that didn’t rely on a model, so there was no chance of any model errors.That was the summer of ’09. We went back and forth on the algorithm for a few months, and the site went live in the beginning 2010. Within a month or two, it had its first user at $18 per month — a CFA in Silicon Valley. That summer the number of users spiked by 100%, to two. I spent most of my time focusing on another site, called Short Screen, one designed to help short sellers.Short Screen got a little bit of traction, but I didn’t use it often enough (or well enough) myself to feel comfortable promoting it. I sold it last year to someone who did, and spent my time working on Portfolio Armor, making some iterative improvements to it, based on user feedback.I wish I could report one of those exponential spikes in users for Portfolio Armor, but it’s been more of a gradual grind so far, thanks in part to the anti-buzz I’ve built around it. On the plus side, it turned profitable enough in 2011 to pay my bills, and pay for some new capabilities I hope to roll out next quarter. And those new capabilities may convert some one-time payer mobile users to ongoing subscribers.One of those new capabilities will be to help investors hedge with optimal collars — I remember Fred mentioning a few months ago that he planned a post on collars (or, “collar trades”), so I keep hoping I’ll be able to roll out this feature before he blogs about collars.

    1. fredwilson

      building the thing you needthat’s the purest form of startup inspiration there is

      1. Dave Pinsen


  87. DonRyan

    I’m late to the party here but our firm started like so many others. My partner and I worked at the same firm and became increasingly disenchanted with its direction, management policy, etc. In short, we felt like we were being treated like chattel. While moaning about our situation, we agreed that, if we wanted to, we could create a firm better than this. Once that seed was planted, it was only a matter of time before we had to act on creating a better firm. We are now in year five and have created one other firm and have two more in the concept phase. For any entrepreneur, I think the magic spark is the idea that “I can do this better”. Or, as has been said so often here, we find a problem that annoys us so much we are willing to disrupt our lives to solve it. That’s my story. 

  88. Alan

    My wife Janice and I launched Custom College Visits website in late December of last year. So far we have received four requests for proposals from parents needing our services by way of the website. That might not seem to be a lot, but for this bootstrapped start-up we are thrilled. We started talking about starting this business after my daughter went on two east coast college visit trips with her high school class. They were pre-arranged bus tours and did not allow her any flexibility. What really kicked us into action was when a good friend said; “Janice I wish there were someone to do this planning for me”. She was in the midst of trying to coordinate the plans for an East Coast college trip — all the while trying to hold down a full-time job, figuring out what to make for dinner, wondering when she’d get to the store for groceries and who would pick up the kids from their various activities — never mind that she still needed to figure out arrangements for college test prep and visits to the local high school college fairs. Sound familiar? We thought wow, we know how that goes and there must be  parents and teens around the world who could use a bit less stress going throughout this experience. A few months later we chose the name. This is truly a bootstrapped business that we are figuring out as we go. But we are both working together to build a company that provides value to other families. Revenues and profits are certainly high on the list, but with the response we have received we believe they will come sooner than planned. My wife and I have tried to start business in the past but kids and life got in the way, this time its full steam ahead!

  89. panterosa,

    How I Got Kidnapped Into The Most Boring Job EverThe economy is in the toilet in the early 90’s, my family is in the real estate business, residential and commercial, headed straight into the toilet too. The commercial buildings are worse – we lost voting rights and having the two biggest assholes for partners spend all day fighting each other as we lose money on buildings. Complete disaster whose only remedy is beer mug sized martinis.I am dragged in kicking and screaming into help. They treat me like a complete idiot, because I have a newly minted BFA in Sculpture, the most useless degree on earth (which causes my widowed mother and her kabal endless handwringing) and who cares if I just had a solo show in Soho. Soho closed shop a few months after, and I had been stalked because of the racy content of my work which was very ballsy. So from roaring lioness to wet abandoned kitten in a few months. How I Turned Into A Stealth Apple Cart TipperEveryone underestimates me and I begin to love that fact. We buy back a building we had sold at auction, and resume managing it. I read all the documents and contracts and find things the others haven’t, and as a result we almost sue the law firm who repped us in the sale and we took out top two tiers of the buyer’s bank for illegal activity and non compis menti. I begin to figure out what needs to happen to escape, which involves unraveling two separate partnerships. I divorce my family, and the other partners on paper, forcing sale or division of all property and cash. I escape! and take a tax loophole encumbered chunk of cash out with heavy debt on it and do a 1031 exchange. I run the most boring NN lease with an AAA tenant a few hours drive from NYC. It’s supposed to be an NNN lease, but isn’t, which means I can’t ever do bigger design work, and be a full time mom because some disaster will hit and I’m MIA dealing with the interruption. 10 years into the most boring job ever, having done everything right, paid down the entire mortgage in record time, and finally sole owner, I decide I am Over it and Done!How I escaped The Boring JobI drove with my still handwringing mother to see stupid property needing new roof for big $$ that I don’t have and don’t want to borrow. We meet contractors and look at the beat up building which AAA tenant runs badly. Round speed trip 8 hour drive, ate in car. On way home, my mother looks at me and says “Your job is a beat up minivan. You have a brain like a porsche. You need work that’s a porsche.” My goal to tip over another apple cart is successful and I have someone on board to help me push!  Previous advisors all disagree though and wring their hands and object, and I ignore them. On market to closing is 15 weeks in 2010. Victory. #paywindowPS In the meantime of the above, I divorced, and moved with PantherKitty a few blocks away from the wasband. And importantly, began coaching to help sort which career to pursue once the real estate was sold. A few false starts and learning curves, but getting the hang of it, and balancing life as a single mother half the week and a single woman the other half the week.A New StartGo full time on new awesome idea and live on sale proceeds, happy to be Free and doing something which has Content. Even with the crazy ups and downs. I built a team of four and lost 2, but still keep looking for the right partners. MVP should be built in 2-3 months. Last year a real hot shot, who I admire greatly, told me if I could get my idea verified by scientists it would be a game changer in the field, and a big science prize winner. I reported back to him recently that I got everyone on board and I’m ready to show him. Looking forward to that. Apple carts need to go over, regularly. I absolutely adore my work, PantherKitty is thriving, engaged in startup living, and just had her first comment here at age 10. I have grown into the risk taker I have always been.Stay tuned for the next apple cart to go over. It’s a bigger one this time and should be more fun.

  90. Ela Madej

    @fredwilson:disqus  I’m a bit late to read it / reply.. but I guess we have an interesting story ;)Me and my 3 co-founders started our first company Applicake 5.5 years ago when we were all around 21 years old. We were all high-school friends and we all took a lot of computer science in school. All of my co-founders went to study CS (I haven’t – my mom, dad and sister are computer engineers so back then I told myself it would be a cliche –  and here I am in the world of tech nevertheless ;). Back to the story: In the summer of 2006 one of my friends Pawel went to Stockholm and worked there as a programmer (in fact, he’s been doing programming gigs since he was 14). They taught him Ruby on Rails when no-one in Poland knew about it. He came back after that summer vacation and the Swedish company told him they would give him an app to develop IF he can find more people and teach them Rails. After a dinner and a generous amount of wine we all said “let’s do it”. We thought it would be fun and the money was not too bad.Not only did we know nothing about running a business, we also knew nothing about the technology we were going to sell. But we were honest about it and the initial payment surely reflected our skill level 😉 In fact, we only formally registered the company so that they could legally pay us. I was actually only going to help them with getting European Union grants /funding, I was planning to focus on my academic work and stay active in an association for civic society I helped set up with my uni friends. Funnily enough, my role at that association was to promote entrepreneurship…Now the real fun part started several months into that “company”. We:(1) We were extremely thrilled and exhausted at the same time (hmm, somehow those feelings stayed with me ever since). (2) The project took way longer than planned so we were alson broke ;)(3) All knew WE HAVE to work together and we want to make this “serious”(4) Knew that we CANNOT be dependent from just one big client because it sucks, we were also tired on working on a project that wasn’t fun(5) We told our then-current well-known German client we don’t want to work with them anymore. They would’t negotiate the rates and we did not want to be “just another disposable cheap software provider”.(6) We could not find any other good clients and interesting international projects and we run out of money (all money)(7) Then we panicked (we were really really broke) ;)(8) We decided to go to the US for the summer. We borrowed money from our parents to pay for the flight and for our “work and travel” student visas. Pawel’s parents actually sold their old car…(9) We rented a house at the beach and worked in bars in Hamptons (Montauk & Amagansett), spent great summer there, bought good laptops, saved sth around net USD 17k (which was shtiloads of money for us), invested it back in our tiny company and bought ourselves more time(10) Oh wait, we were working in restaurants & bars in the evenings but did some coding work during the day (we also had one “employee” in Kraków during those 3 months)Then we built our first product (social travel network) that failed (but was fun!). Then we started Future Simple with our current partner and CEO from Israel (which is doing very well). Then we started European Rails Conference Railsberry (which was going to be a small local event but grew out of proportions and will be a blast). In a slightly modified team (two of my co-founders are focusing on Future Simple full time since we closed our first round of financing which totally makes sense), we are starting a new company & launching a new product in a few weeks.Having a consulting company like Applicake around was very useful for all these years because we never took any real loans, any external funding except from non-refundable EU grants and the recent round A at FS. While I could see us getting out from the consulting model very soon, it was hell of a ride, it gave us amazing financial freedom and we have worked with amazing teams and startups from all around the world.Being in Poland, we’d have never gotten where we are now if not for that one dinner & all that wine (?) in 2006. As of today, we made a decision to split to focus on different companies, we work on different teams but we still see ourselves as that founding team. That’s how we got where we are now and in our minds it’s only the beginning.

  91. Scott Kolb

    I moved back to my native California, Carlsbad specifically, before my freshman year of high school.  I made my first friend during third-period PE, Kyle, a guy who seemed to relish in meeting the ‘new kids’ and helping us integrate (in the best way possible, not the ‘check out the pool on the roof’ type).  I also met the multimedia teacher and yearbook adviser, Kumu, that year. He wanted to start an online ‘portal’ (this was ‘99) for our high school. Everyone would have their own LCC email address, you’d be able to talk to friends and teachers in both academic and non-academic ways, and generally be this amazing place for students to connect online. We didn’t get far because none of us knew how to program and instead wasted time on things like domain names and co-lo’s. Nonetheless, Kyle and Kumu would be big parts of my life 10 years later.I was living in Hong Kong when the global financial crisis hit. Kumu had emailed me in years past about an idea for a new website.  I had always said no because of my then-jobs, but now the time seemed right.The idea was to build a site where all the answers to student’s homework was posted for free. We really believe that the education system needs a HUGE shake up. The model we’ve been using doesn’t work. We need to move away from a model where we reward effort (homework) and move to a model where students must prove mastery. There are a lot of other companies focusing on education, but ours has the most immediate impact on today’s students.I moved down to Sydney, where Kyle was living, from Hong Kong to hash out a business plan. We built a prototype, secured some family-and-friends money, and decided to move back to America.  Being from San Diego we were naturally disinclined on moving to ‘NorCal’, no matter how cool SF might be. New York seemed like the best fit, cost-of-living be damned.  We hired a few people in NYC, packed our bags and hopped on a plane.  Slader was off to the Big Apple!

    1. Helen Gregson

      Love it. A long-lasting connection/friendship like that can definitely be a strong indicator of a successful business partnership. Too many times ill-matched individuals come together for a common goal; and no matter how committed to the goal they are, their inability to work together impairs success.

  92. fredwilson