This Week In Startups

A few weeks ago Jason Calacanis stopped by our new offices and recorded an episode of This Week In Startups. It was a fun chat, almost an hour long. My audio is not as good as the audio on Jason so it's a bit hard to hear me unless you want to hear Jason shouting.

If you want to fast forward through the sponsorship message, go to 6:30 and start there.

If you want to fast forward through parts of the discussion, here is the breakdown:

0:00-1:00 Welcome to TWiST from NYC in the Union Square Ventures' offices.
1:00-2:00 Thank you to iStockphoto for sponsoring the show.
2:00-6:30 Demonstration of how easy it is to purchase high-quality photos within iStockphoto.
6:30-8:00 Welcome to Fred Wilson, principal at Union Square Ventures.
8:00-8:30 Jason: The biggest mistake of my career was not listening to [Fred’s] wife when she advised me to go national with Silicon Alley Reporter.
8:30-9:30 How much of being a VC is being a therapist to the entrepreneurs?
9:30-10:30 You’ve worked with Mark Pincus, what was that like?
10:30-11:45 You invested in all four of Mark’s companies, yes?
11:45-14:00 When Mark came to you for the fourth time with Zynga, what did you say?
14:00-15:15 The same sort of situation happened with Twitter, didn’t it?
15:15-16:30 If a VC flies out to see you–the entrepreneur–you know there’s serious intent.
17:45-19:15 So speed is the big difference between web 1.0 and now?
19:15-20:15 Have you ever spoken for your companies too much on your blog?
20:15-20:45 Your blog has really made you into one of the most well-known east coast VCs around today.
20:45-22:30 How much of your success this time around has been because of the blog?
22:30-23:30 Did you enable too much transparency and lose some of your power?
23:30-24:30 If money’s not an issue, why go to a VC?
24:30-25:00 Are there funds that are now following Union Square Ventures?
25:00-26:00 Thank you to MailChimp for sponsoring the show.
26:00-29:30 Demonstration of how you can segment your lists to target your emails using MailChimp.
29:30-30:00 Fred explains why he would like to see entrepreneurs work backwards and think about who they would like to invest in them.
30:00-32:15 How do you reconcile this, the new golden era of Internet companies, with the scars you have from past fund failures?
32:15-33:00 When do founders start thinking, “I should start a new company?”
33:00-35:15 Let’s talk about entrepreneurs. What are you looking to see in the eyes of an entrepreneur?
35:15-37:00 So you’re looking for a persuasiveness that is so strong, people can’t help but follow that person?
37:00-38:15 Do you find that this new generation of founders has an entitlement issue, thinking that they’re owed success?
38:15-39:15 Does that make that person impossible to manage?
39:15-42:15 Are you on the secondary markets? What’s your take on that?
42:15-43:45 Fred: Are Mahalo shares being traded?
43:45-45:30 Are limited partners stoked about the secondary market?
45:30-46:15 Why does a venture firm put money into a single established company and not into several startups?
46:15-48:30 What does an opportunity fund mean?
48:30-49:00 Fred: In the private equity business, you buy one and you’re done. In the venture business, you make multiple investments and the risks are mitigated.
49:00-50:40 What’s your advice for a young entrepreneur who wants your money?
50:40-51:15 Fred, it’s been great to watch you rise over the years. Thank you so much.
51:15-51:45 Thank you again to our sponsors. We appreciate all of your support!

#VC & Technology

Comments (Archived):

  1. leigh

    I think a bunch of your comments about entrepreneurs (evangelical leadership, piece about not investing bc someone just wants to make money, emotion connection to ideas) kinda boils down to passion.  When someone really believes in something, is passionate about it and has the experience/knowledge to back that up, it becomes addictive.  You get as addicted to the idea as they are.  When belief becomes a group activity, your half way there already.

    1. fredwilson


    2. awaldstein

      Well said.Passion is the great connector. It cuts through doubt, disbelief and impossible odds.I’ve been thinking that passion is the greatest filter we have.

      1. William Mougayar

        I like that evolution of what started as a “passion graph”. Passion filter is more descriptive.



      1. leigh

        or marketing 😉

  2. Marcelo Toledo

    Fred, I’ve missed you in a show like this for a long time. Simply terrific! Thank you.

  3. Matt A. Myers

    You seem quite calm in this video – keeping up with your weekly yoga? 🙂

    1. fredwilson

      Yes. At least twice a week every week and sometimes three times. I can’t gowithout it

      1. Matt A. Myers

        Awesome. 🙂

      2. ShanaC

        What’s your preferred style?

  4. Carl J. Mistlebauer

    Awesome!  Just awesome!I have met with a few VC guys and angel investors, along with a bunch of small business development folks and start up folks and honestly, and I know I am to be in awe of them, but they don’t come close to you!  I have been told twice that I am “cursed with knowing my industry too well” or “…with knowing too much…” and I have walked out of those two meetings realizing that what I thought was a compliment really wasn’t!The hardest thing to do is to take what I know and convert it into what others are accustomed to dealing with.  I know, for example that for an investment of X we will achieve A.  Now, I also realize that this will create other opportunities that we can exploit for our benefit.  I know for a fact that we will collaborate with other product manufacturers to bring their product into our market.  But I had no idea what products or when but I knew that the opportunities will arise.  I also know that we will eventually create stores, I have no idea when or how or where but I do know that stores are in our future, now whether they be brick and mortar, pop up stores, or stores within stores I have no clue…but the opportunity will present its self and we will exploit it.  I know that we will eventually be able to turn our IT department into a profit center, we will be able to market our database, our marketing, our advertising, and our logistics to other product manufacturers who specialize in our niche, when and how that occurs I have no idea, but when the opportunity presents its self we will capitalize on it.I have a spreadsheet that shows the pivot points for expansion but can I date them or number them in sequential order…no I cannot.  For example, I stumbled on a start up that is marketing customized polo shirts….been in business a month!  We have traded a few emails and I have offered to assist in anyway I can, because down the road I want to introduce his capacity to our specifications and create a whole new opportunity for his company and my market.But he did not exist while I was making my last presentation.  Its real hard to get people to realize that I cannot dictate if and or when there will be additional funding rounds; after 8 months we will be profitable and we might be able to fund future expoiltation of opportunities that emerge internally, other wise we will seek another funding round, but since future opportunities are additional revenue they should be viewed logically on their own merits.Six months ago, was an unknown, but I have plans for it now….I realize that I could create the big picture and go seek a massive influx of cash but I also know that I work better starting from the other perspective….I just find it hard to believe that Picasso sat with a blank canvas and knew exactly every detail of what he was going to paint before he made the first brush stroke….I think passion and knowledge exploit opportunities as they arise or are created…..I think that sometimes we confuse passion with tunnel vision…..

  5. David Semeria

    I thought that was a great interview.Especially because Jason gave you enough time to flesh out your answers. In past interviews Jason interrupted too much, but he’s evidently getting much better at this.It came across like a conversation between two friends – which is great – and between you both you generated many insights.

    1. awaldstein

      Agree completely.Felt less like a Q & A and more like a conversation…like a joint musing.Authentic and inclusive.

    2. fredwilson

      I agree. It was fun doing it too

      1. David Semeria

        It’s way past your bedtime Fred. Jet lag?Get thee some melatonin – it’s what the pilots use, totally natural and works like a charm.

        1. ShanaC

          I live on melatonin recently.  It really keeps me asleep, when I need to sleep, rather than waking up in the middle of dreams.

        2. fredwilson

          i tend to stay up later and sleep later when i am in europe. i slept to 10am today which is 5 hours later than when i’d get up in NYC

          1. Matt A. Myers

            Eating meals at the local “morning time,” “lunch time,” and “dinner time” was found to be the way to shift your body’s internal clock … just something I keep in mind when traveling.

    3. RacerRick

      Jason is usually really annoying as an interviewer.  He seemed way more comfortable with Fred.That was very entertaining. 

  6. William Mougayar

    47:50 “Venture Capital is just like poker”. Priceless.

    1. Austin Clements

      Fred laid it all out back in 04 In a post titled “The Poker Analogy.” That’s actually the post that first introduced me to this blog.…Just reread it and it’s a great article but it seems like there is room for an updated post given the current ‘frothy’ VC environment. What happens when everyone is playing loose-aggressive?

      1. ShanaC

        I wonder where he came up with the analogy

      2. fredwilson

        Go to another table?

        1. Matt A. Myers

          Or wait until you have a hand noone can beat and ‘take them for all they have.’Scenario:Has been years since I’ve played poker … but a friend I was playing ended up having a full-house, and I happened to have a straight flush (or maybe 4 of a kind) after flop. Prior to that I pumped up (invested in) the pre-flop pot, so there’d at least be something to win if my cards ended up in my favour (sort of like angel investing).. Friend was close to his full-house. He kept slow-playing me. I tagged along. In the end, I raised him knowing he’d call it — and possibly even go all in, which he did. His excited reaction after I called was unforgettable — and the disappointment after I showed him my straight … well, priceless?I know that I exposed my main poker strategy to everyone on AVC — if I ever play any of you, I’ll just use my other winning strategy. 😉

  7. sigmaalgebra

    (1) There are descriptions of ‘creativity’ in research based on seeing ‘patterns’, ‘connections’, or, better yet, possible ’causes’ in what is being observed, and such creativity is seen as a good thing. (2) More generally, seen as a good thing is taking an ill-defined situation and obtaining clear understanding of it. (3) In any such work, it’s also important to avoid drawing false conclusions.From that video, it’s clear that in venture investing you’ve done a lot of (1) – (3). Good. Important. Not easy to do.E.g., for (1) you saw some of the potential of blogs but also some of the obstacles and then saw Twitter as a ‘blog’ anyone could do. Nice. Also (from elsewhere in your blogging if not from that video) you saw that ‘social connections’ and, thus, ‘communities of engaged users’, a concept it appears you formulated, such as via Twitter was important. Nice again.For (2) you gave a clear formulation of the differences in venture investing and private equity investing. Also nice.For another nice observation, you noted that an entrepreneur needs to be careful whom they ask to be on their Board, e.g., that the Board member needs actually to understand the business. Since I’ve been terrified of the possibility of having a Board that didn’t understand my business, your observation sounds to me like much needed progress. When I interact with VCs, it appears that nearly none of them understands your point that I am giving them a test: Do they understand what I’ve explained about why my business is promising?For an aviation analogy, in a sudden patch of rough weather, if the pilot knows that the airplane can take several Gs of positive or negative stress, has multiple instances of all instruments working well, is in good communications with air traffic control, has all the aircraft maintenance current with high quality, has plenty of fuel and reserve fuel for the destination and also several identified alternate destinations, etc., then the pilot can be quite confident even if they can’t see more than 100 yards out the front windows. However, a passenger who only feels the turbulence and sees only the rain outside the windows might become scared and want to land ASAP. Understanding the situation is very important. The pilot is not taking big risks; instead, he understands what’s going on. To set aside fear and have good judgment, it would help for the passenger also to understand what is going on. In a company, a Board member who just doesn’t understand is a threat.For (3) you noted, e.g., that the VC Board member is not really the “boss” of the entrepreneur, that the entrepreneur needs to really understand their business, say, from some years of concentrating on it, and that it is not good to think about an ‘exit’ in overly simple terms. Good.Net, and important for any promising entrepreneur, as you are demonstrating in public, you are thinking actively, creatively, and productively about the issues of getting these companies started and successful. In particular, that you saw the importance of blogging is an example of (1). Nice. I know some quite bright people who, even with your example in front of them, can’t identify, formulate, and articulate the ‘business relevance’ of your blogging; that you saw the relevance early on, from ‘whole cloth’, without any examples, and made it real is nice.I would add three remarks:(1) From the entrepreneur’s side of the table, most VCs would help themselves if they also blogged with so much ‘relevance’ and, thus, demonstrated to entrepreneurs that they, the VCs, understand well what is going on.(2) Just from ‘macro economics’, the coveted successes are necessarily rare. So, we have to expect that the means of such success will be rare and usually novel and, thus, not many people will understand the means before any clear examples. So, both entrepreneurs and their VCs, in early stage work, if they are to avoid just shots in the dark and depending on luck, will have to be willing and able to evaluate means that are both rare and novel. That is, generally the common and well understood are not promising.(3) I would suggest that stronger barriers to entry, stronger “moats” in Buffett’s word, than ‘communities of engaged users’ and stronger reasons for users to become ‘engaged’ than being in such ‘communities’ are available and should be emphasized.

    1. Guest

      you prob. have some really good stuff in here…but I stopped reading after (1)…do you supply crib sheets for the rest of us?

      1. sigmaalgebra

        “Crib sheet”?  Okay:I’m pouring thick, sweetest possible Vermont maple syrup topped with powdered sugar and pastel colored sugar candies on Fred’s post and associated work.So, my post is about Fred’s post and work:  Well, my first paragraph makes some broad comments about what is ‘good’, that is, worth sugar, in work.The second paragraph claims that his video is evidence that he has done such sugar-worthy work.The next few paragraphs explain in detail how his work meets the criteria of sugar-worthy in the first paragraph.Then at the end, as an entrepreneur, I add three remarks back to VCs in general.The first remark says that more VCs should blog as Fred has done.The second remark attempts to drive a stake through the heart of the hideous monster pushing VCs to doing too many simplistic pattern matching, me-too, and herd following projects instead of looking deeper in sugar-worthy ways as Fred has done.  Of course, this remark is really more aimed, although indirectly, at any LPs, if there are any, who are less than fully sugar-worthy and trying to “manage” and “boss” their GP VCs.The third remark is to ‘qualify’ Fred’s ‘communities of engaged users’ as a barrier to entry or Buffett “moat” and to urge stronger barriers.  Without saying so, the hint is that Google+, Microsoft+, Yahoo+, Liberty Media+, Conde Nast+, NewsCorp+, Disney+, Two Guys in a Garage+, etc. could also threaten to cross the moats of Facebook, Twitter, Zynga, etc. so that wider moats could be useful.In summary, one of the biggest challenges we all face on this blue marble 13.7 billion years after the starting gun went off is knowing what the heck to do and to do that by looking at the chaos in front of us and seeing how things actually work.  Such seeing is important and fully sugar-worthy but not easy.  Of course, the grand example we have is shepherds watching their flocks by night, without urban light pollution, seeing the fixed stars, and then watching the ‘wandering’ stars.  How did the wandering stars work?  Via Newton, something over 2000 years later, we had a good answer.  Good?  Yes.  Easy?  No.  Then a few hundred years later from Uncle Al we had a better answer.  Now we are looking for a still better answer that combines gravity and quantum mechanics.  Easy?  Heck no.I listed some ways in which Fred has looked at the chaos, found meaningful answers to how the things worked, and saw what to do.  E.g., suppose you had some tens of millions of dollars from some hard nosed LPs who wanted RETURNS of several times those tens of millions and a guy came in with a project for 140 character messages instead of e-mail or blogs.  Would you see why that would, could, and should work?  Could you see it and explain it, enough to write a check and not have LPs bring a dunce cap?  To have seen that one, I would have had to have had a very clear explanation and then put my feet up for a long, quiet afternoon to see just why it would work.  Net, almost surely I would have missed it.  Here Fred was working with just the chaos and ‘whole cloth’ and not following any very well “set patterns”; neither was Newton with his second law of motion and law of gravity to explain the “wanderers”.Fred’s analysis was that tweats were ‘blogs’ anyone could do.  Nice.Of course, much of the ‘reason’ Twitter worked is in some sense ‘social’.  Okay, there is the old, dense, obscure:Erving Goffman, ‘The Presentation of Self in Everyday Life’, Doubleday Anchor Books, New York, 1959.Hmm.  So, in part, Twitter, and blogs, are about ‘presentation of self’.  So is much of ‘social media’.I couldn’t make sense out of Goffman.  My (late) wife, however, read Goffman faster than I would have read a comic book — it was all fully obvious to her, mostly before she opened the book.  How’d she do that?  Two ways:  First she was brilliant — Valedictorian, PBK, Woodrow Wilson, Summa Cum Laude, Ph.D.  Second she learned from her mother who was at least bright and spent nearly all her waking life analyzing social situations, even at church socials likely burning more glucose per second than Newton did analyzing the planets or I ever did learning the Hahn-Banach theorem or, last week when I was off the grid for a few days, reviewing the proof of the completeness of the Hilbert space L^2 (mind blowing that it could be true, but it is, and the proof is nice and the result is nice for my project).So, right, we should consider Goffman as a ‘theoretician’ of ‘social media’?  Maybe.  Maybe if I really understood Goffman I could say!If so, would that mean that my wife could have been a leading VC of social media?  Maybe, but few stranger things have ever happened.  Better would have been for me to ask her to explain what the next big thing had to be in social media and to start typing in the code.If not Goffman, then what?  Well, there is:Deborah Tannen, ‘You Just Don’t Understand:  Women and Men in Conversation’, William Morrow and Company, New York, ISBN 0-688-07822-2.who learned from Goffman.  Tannen is much easier to read than Goffman!  So, does ‘social media’ have to do with ‘women and men in conversation’?  Yup.  So, maybe Conde Nast+ could be a threat to Twitter?  Out of my depth, and I can’t ask my wife!Note:  Of course Fred has already said he likes Google+.  Why?  Don’t ask me! 



      1. Matt A. Myers

        I just filled out your adoption papers — yes, I’m forging them, and you’ll soon be my child robot dinosaur.

        1. FAKE GRIMLOCK


          1. Matt A. Myers

            I think I still prefer me adopting you and not vice-versa…

          2. FAKE GRIMLOCK


  8. Peter Sullivan

    Awesome interview. I love the way Jason asks questions and really follows up with them. Could listen to you guys all day. You really should of checked those mics though. 

    1. fredwilson

      Sorry about the audio. Its a bummer

      1. Peter Sullivan

        It still works. More of a bummer for Jason really.

  9. Eric Ni

    Wow. I will admit I haven’t been reading your blog regularly nor do I ever comment on posts.  But I just have to say this talk is very revealing.  I’ve been running my startup for the last 5 years starting right out of college, same space, same team.  Went 3 years without salary, without any other jobs.  We still use code we wrote in 2006.  Raised some angel funds, never raised VC money.  But now I’m beginning my 3rd round of pitching VCs, with a 3rd iteration on our product.I hope my next investor believes in the same things you do.

    1. fredwilson

      I hope so too

      1. Eric Ni

        Thanks Fred!  I really didn’t expect you to respond.  I would love to tell you our story some day.How we didn’t graduate from an Ivy League college as predestined prodigies.  How we started with nothing special, no money, no experience, and no network.  How the only thing we had going for us, was the belief in our ability to build and evolve our product.How we took a consumer idea that failed, evolved the technology into a B2B service to survive the recession, and positioned it as a leader in our market. How it took me 5 years to finally get a meeting with Sequoia and hopefully with you.  How the next 5 years with our new consumer concept is going to be 1000x bigger and leverage everything we built in the last 5.I’d like to share that story with you.

        1. fredwilson

          send me an email to [email protected] and put “per the disqus comment” in thesubject line

  10. Agustin Gonzalez

    A few observations from my perch:1. There is no question that Fred is greatness. He knows his domain, entrepreneurship/VC, as well as anyone in this modern era. I was telling a friend recently “this Fred Wilson guy is the Kobe Bryant of internet entrepreneurship and venture capital — the alpha dog.” This interview clearly cements my sentiment.2. Folks like Fred Wilson and Peter Thiel are the types that will lead our country into doing great things. While it becomes disheartening to see our country mounted with public debt and run by a bunch of self-serving politicos, this gives me hope.3. I like Jason Calacanis but his intro infomercial is one of the quickest ways to create discourse with his viewers. It was forced and look bad. I think there might be some upside to the “This WeekIn” brand but he needs to take caution. Having 100 producers and the 7 minute infomercial is not a an attractive component to his media brand. But whom am I? Just a nobody…Having said all of that I still love Jason — seeing these two guys mix it up is a thing of greatness. Cheers!

    1. Carl J. Mistlebauer

      Fan,Don’t be so hard on politicians…they only represent the interests of those who pay to put them in office.  Sadly, innovation and growth sometimes has to battle against some pretty big vested interests.  If you find yourself in an industry that is not innovating then you have to find other ways to protect you business interests and your margins.In the world of “old tech” you realize that the concept “smaller government” applies to everyone else but you and your business…I cannot think of one major project, in Rand Paul’s hometown, in the last 10 years that was not funded one way or another by local, state, or federal funds….I doubt anyone could point to anything over the course of the last 10 years that did not owe its existence to government funding…I call it socialism for capitalists….the bigger you are the more you benefit!  If you really want to be an outcast try being a small old tech business owner…..its like being a leper!

    2. Prokofy

      I agree that Fred is the alpha dog. And he’s in our very own New York, and in our very own neighbourhood of Union Square! Woot!

  11. six pence

    j cal is gettin a bit floatatious around the jowls!

    1. essay

      Thats preatty true!

  12. falicon

    I love that you point out ‘overnight success’ generally means years and years of obsessing about and over an idea…I think that’s probably the best kept secret in the internet start-up world that there is.Just because the majority of us don’t hear about something until it’s ‘something’ doesn’t mean the founders weren’t working on variations of the idea for a long long long time.For me personally, I’ve been building one-off social data tools for a couple of years now under my brand just playing with concepts and learning what’s needed, what works and doesn’t, and what people really need/want…and it’s only now coming together as a true vision with …but most people who find/use will prob. never even realize all the time and energy that went into the various things and the many many others that I either already killed off or just never got fully to market.It’s easy to think success is just one or two Rocky training montages away…just kick on the music, run a few miles, swim a few laps, and you too can take down Apollo Creed…but the reality is that it takes a lot of sweat, a lot of training, and a lot of hard work to make winners…



      1. Matt A. Myers

        Can I adopt you? Pretty please?

  13. Robert Thuston

    I just skipped around in this video on my TV (Boxee) while using my Ipad (viewing this post) to identify where I wanted to be in the video.  Good stuff.  Term sheets:  What if I, as an entrepreneur, never wanted to understand the exact language or look at a term sheet when getting financing? Let’s say I just wanted an investor I trusted to be able to explain it at a high level as to what’s fair and what’s incentivizing me and my team to work as hard as we can. Maybe the investor shows me a powerpoint, and then maybe attaches the powerpoint and notes as an addendum to the term sheet (for me to sign).  What’s the risk?Evangelists: Some of us are passionate, but not necessarily evangelists.  I stumble over my passion often because I’m too excited when I should be listening, or I speak too much when I should be building rapport, or I talk of my own values when I should be asking someone about theirs. Evangelists empathize and meet people where they are when communicating their ideas.  I’m getting there one conversation at a time, and glad I’ve got some many great people to learn from.

  14. jerrycolonna

    Thanks, Fred, for all the kind words. God, watching the two of you brought back memories. It was great; felt like some of our old “lunches” in the office on Mondays.

  15. David Adewumi

    This is a great post. Thanks for sharing it Fred. It’d be great for students at less entrepreneurially-minded universities such as Penn State to receive talks such as this. I’ll be sure to show students there this video who are interested in starting their own venture.

  16. Prokofy

    @Jason, as ever was! I wondered what happened to him after Mahalo died. You know, I was so enthusiastic at first about Mahalo. I joined and I enthusiastically made a page or two and worked away at maintaining them and earned some of those spacebux he had on there, but then all of a sudden, he insisted that we take “page promoters” or “hall monitors” or I forget what he called them who would “boost our productivity and value”. But of course, they merely leeched off what ever the company *was* willing to pay for our content, which was only a pittance. My page didn’t update right because of some glitch, I couldn’t get help on the shout box which was never about help for the thing itself, and as a result, I was told my hall monitor was going to take over my page. I rebelled, and told Jason to get rid of those leeches and let me collect all the revenue and work my page! But he kept writing me smarmy little memos to “get with the program”. In the end, I said that my page was going to “get it in the neck” if he didn’t get rid of the page monitor! And he banned me! Then he came crawling back a year later asking me if I wanted to make my page again. And I said, no, Jason, go fish! Has he learned anything about how to encourage content in all this time?! That’s what I’d like to know.

  17. thirtythirtynyc

    just something I keep in mind when traveling. Hotel Thirty-Thirty

  18. Philip Baddeley

    Great interview.  Frustrating about the sound as great teaching resource.  Also why shadow boxers against the bright light from the windows.  And all the sponsors!  Not something we have to put up with Robert Scoble……..  But great, great content and great interviewing skills.  Just need to get the production skills to match…

  19. Ben Milstead

    Really enjoyed the interview. Loved the point about working backwards and looking for the right investors. Thanks so much for the work you do on your blog — it continues to be a great resource.

  20. Mike O'Mary

    This is my first visit here. Great interview. Thanks for sharing the insights — and for encouraging entrepeneurs.

    1. fredwilson

      thanks. i saw the critique from the british guy. did not see the collegehumor thing. very funny