First Time vs Serial Entrepreneurs

I've been thinking a lot about the differences between first time and serial entrepreneurs. We invest in both and do not have a preference betweeen the two. But there are significant differences.

The best first time entrepreneurs have been stewing on their idea for quite a while. It is a personal passion of theirs and they bring to it a fresh take, a stubborn insistence on their approach, and they obsess about the idea 24/7. They often get the right product into the market at the right time and they capture the user's attention and usage with that product/market fit.

Where first time entrepreneurs often struggle is when the product works so well that they have to quickly build a company to support the product. Most of the time, the first time founder has not spent anytime thinking about what kind of company they want to build, what kind of people they want to surround themselves with, what kind of culture they want to create, etc. The first time founder often has no experience recruiting, managing teams, and building organizations.

Serial entrepreneurs, on the other hand, often struggle with the founding idea and getting to product/market fit. They start the second and third and fourth company because they love startups and they don't know any other way to work and be productive. But they often lack that passion around a singular idea that drives first time founders.

But when serial entrepreneurs do settle on the right idea and find product/market fit, they are usually terrific at building the company. They know when to step on the gas and where. They know how to recruit, manage, and structure organizations.

I was talking about this dichotomy with another venture capitalist the other day. I likened it to the first album/second album issue with rock bands. So many bands struggle with the second album and there are many reasons for it. The first album is something they have been working on for years. These are the songs they played night after night in the clubs working their way up. These are the songs that got them their fanbase and got them signed. The album hits, people love it, and then they spend the next year touring like crazy to build their fanbase. And then they have to go back into the studio and write and record a second record in a matter of months. It is no wonder that is is terribly hard to produce a second record as good as the first.

Likewise, it is often hard for the serial entrepreneur to produce a second startup that is good as their first. It takes a lot of patience and collaboration with others, two things they probably did not use much of in their first startup.

As I said at the start of this post, we work with both first time entrepreneurs and serial entrepreneurs with equal interest. We love the ability of great first time founders to nail the product and get significant user traction quickly. And we work closely with them to build the company once that happens. And we understand that is an area they are uncomfortable with and need our patience and support with. We also love the serial entrepreneur's gifts around building the company and taking control of a market once they have gotten product/market fit. We work closely with them in their efforts to find product market fit and we understand those challenges and are patient and supportive during that time.

These observations are generalizations and certainly do not speak to each and every situation we've been involved in. But they do reflect our experience broadly and we think it is important to understand what situation you are investing in, where the challenges will be, and how best to support the startup. Those things will most likely be very different when working with first time founders and serial entrepreneurs.

#VC & Technology

Comments (Archived):

  1. leigh

    Funny, I met with a couple guys who have a really great product to talk about start ups, marketing etc. He started out the meeting with “I really wanted to talk to you because all the success you’ve had in branding and marketing”. I laughed. I told him – that’s not why you want to talk to me. You want to talk to me so i can tell you everything i did wrong on my start up. That experience has helped me tremendously and couldn’t imagine it being anything but a huge asset if i was ever enthusiastic enough about something in start up land a second time around.

    1. fredwilson

      do you think you will do a second startup?

      1. leigh

        Depends what you call a start up. But starting a new company that’s launching in a few weeks that is in the category i know best – marketing – an industry that is dying for some innovation.That was a big lesson first time around for me. Your going to be doing this 24/7 – make sure then, you are in a category that you are passionate and know a lot about.

        1. fredwilson

          Yup. That’s critical

  2. Mordy Kaplinsky

    It’s kinda like the chiefs vs. indians metaphor. Its usually one or the other but rarely combined.

  3. kirklove

    Nice post. Analogy is spot on. Same thing happens with movies. There are exceptions for sure. For instance Pinkerton was better than Weezer (Blue) and Empire Strikes Back was better than Star Wars. But, it’s rare.

  4. ErikSchwartz

    I’m currently working on the fourth company I’ve founded (since 1987) in addition to working as an early employee for several more.My previous company I certainly struggled with product/market fit (and timing which is a part of market fit).My current company is different. It’s a space I’ve been thinking about (and working in) since 1990. One could make the argument that once everything came together we nailed the product pretty fast. In a year we’ve gone from an idea, to a prototype, to a first system with a few customers. On the other hand we’ve been waiting for all the pieces (technology, infrastructure,market) to fall into place for for all of this to happen for 20 years.

    1. fredwilson

      Anytime you are working on an idea you’ve been tinkering with for 20 years,that’s a good thing

      1. lemino

        you could take it to other places… but I sure like this approach!

  5. CliffElam

    Loved the rock band analogy. More Super Tramp, less Boston?I will tell you one thing I notice: serial guys (at least those of us w/o the big payday) are a lot more cautious about the *really* expensive big steps:1> Quitting your day job;2> Hiring overhead;3> Committing to PR, Tradeshow, Field Sales, etc4> Hiring mono-skilled tech resources-XC

  6. Matteo Pelati

    Loved the definition of a first time entrepreneur, and I’m one of them. I’m really passionate about our product, and want to reach perfection in every part of it. However I realized after some months that we were too focused on the product itself and not enough on the company. The other problem we had is willing to do too much (especially true for very techie guys like i’m) rather than just focusing on a couple of core features and getting a product (even if incomplete) out quickly.

    1. Ivan Vecchiato

      True Matteo, a beta release from founders with a tech background is way further than beta…

  7. Eli James

    The natural follow-up question to this post would be: what’s your experience with first time entrepreneurs making the jump to becoming serial entrepreneurs? Does it happen more often than not?

  8. Guest

    The whole purpose behind the R.O.C.K. Star Business Method micro book series I am writing is to (try to) use music as a backdrop and metaphor for various business issues and concepts. It has been fun exploring and using music as a metaphor and relational tool for some of my business writing.Given that, it is easy to see why I would enjoy this type of post. The Sophomore Slump is often discussed in the art world. Musicians are not the only ones who experience this; authors do to apparently. I also know an up & coming photographer who experienced something similar when trying to put together his second show.The result of some of the artists (e.g. founder/owner) efforts can manifest themselves in the [edit: commercial success of the] end product. This seems to be able to cut across genres (e.g. industries) as well: Iron Maiden vs Pearl Jam say – both of whom I like but clearly different music. Iron Maiden’s first album (Iron Maiden), while not even close to be their best, went platinum – while their second album Killers only went gold. Pearl Jam knocked it out of the park on both their first & second albums but the second album did not have nearly as many platinum accolades.What I find even more fascinating is how changing band members (e.g. founder/mgmt team) can influence. My favorite band is RUSH. On the surface their second album seems to be an anomaly … the second album, Fly by Night, was a bigger commercial success than the first album. However, the makeup had been changed. Neil Peart had joined RUSH for the second album – it was an entirely new band with a very different chemical makeup once Neil joined. So, in effect the second album was really more like a first. Now check the commercial success of RUSH’s third album (the second/sophomore effort with Neil); Caress of Steel was not as commercially successful as Fly by Night.For the readers who like to rebel and go against the grain and who might be working on their second album (e.g. company) at this very moment … do NOT fret! Rules are meant to be broken; there are a number of instances where the second albums were bigger commercial successes that the first … for example, see Motley Crue’s results with Shout at the Devil, which completely dwarfed Too Fast for Love.Here (Hear) is to those that make music!!!

  9. Berislav Lopac

    You’re talking about serial entreprebeurs who were successful in their first endeavors. But what about who failed their first time (or even more than once)? Where do they fit?

    1. fredwilson

      i’d say they are a hybrid and they can be very successful if they still have the fire, passion, and a good idea.

  10. DavidSandrowitz

    So, what does this foretell for first time entrepreneurs who are further along in their careers? Is it possible to do this for the first time if you are over 35 or 40? What of the mix of experience that may have been gained by working at other companies and on other projects, experience that has yet to be applied to one’s own venture?I ask because I think your comments are spot on, at least as far as what the investment community believes about entrepreneurs. Given the post from TC this morning on the relationship between age and success, it seems that there is little room for people trying to start out at a much later stage in their lives or careers. And, I’m not talking 50 or 60 here…it seems that 35 is a death sentence if you have not already proven that you can build a great product and have success. I think this is a shame – these folks just need time before coming to the point where they feel able to exercise their ideas and I would think that the mix of wisdom/experience AND a good idea would be very attractive. So, why does this not happen more often then? How often do you see first timers that are in their mid-30s or older? What is your impression of them?Do you know of any great successes where the founders were both first-timers AND at a later stage in their careers? I happen to think this subject is worth a lot more research (I am a bit biased here).

    1. Guest

      David, I hope Fred and others reply to you as well. Here is my take, for whatever it is worth. There are many barriers one has to overcome; overcoming media bias is just one. :)The following is a YouTube link for Andres Segovia performance. I hope it demonstrates that age should not prevent one from going after it and making and playing great music.

      1. andyidsinga

        andres segovia is beyond awesome.Did you notice when he actually re-tuned his guitar during the performance!?

        1. Guest

          Yes, he is great. Honestly, I did not watch the video I posted (I did let it play in back ground while I composed the reply to David). The first thing I thought of when reading David’s post was Andres Segovia slouching on a stool and I just did a quick search and grabbed a link to share (and hopefully inspire David) as a way to illustrate ‘old’ folks got the chops still too. I would not be surprised if he did tune it while playing.Andy, if you enjoy guitar check out Stefano Barone who is on the CANdYRAT Guitar Tour at the moment. All of the guitarists I saw were good but Stefano blew me away … he integrated technology into his electrified acoustic guitar beautifully … like a mad scientist.

          1. fredwilson

            old folks most certainly still have the chopsbut they have to want to still have the chops

          2. Guest

            Agreed, the desire has to be there …. I think, regardless of age & regardless of whether it is the first, second, or fifth time.

          3. DavidSandrowitz

            And Newton worked on classical mechanics for years before finally publishing Principia Mathematica in his 40s. It can be done, but there does seem to be bias in the system as it currently stands, don’t you think?I think I kick far more ass now that I did in my 20s. I had much better hair back then and my Doc Martens were pretty killer, but I had no idea how to really do anything. But, I also had no responsibilities and could have made a big “sacrifice” because it would have risked little. Kicking ass now is not enough to mitigate risks when the risks are greater and have far more lasting impact than they would have at 22.I’m still trying to wrap my head around all of this and am not clear about the do-cannot do question as far as age goes. It can always be done, but the rate at which something happens and the chance of success seems to be an important thing to consider.

          4. Dave W Baldwin

            To take step further, it is wonderful to watch one of the Romeros boys do one of their dad’s pieces πŸ˜‰

      2. Ana Vidovic

        This post is just great. Segovia = classic but for second attemp this takes the cake:

    2. andyidsinga

      i havent read the tc thing yet – but I wonder if the pool of really good people in 30s and up that is available to startups is simply drastically reduced by them eventually landing in corporations or ‘less risky’ jobs?For instance, startups get acquired by big companies all the time – i wonder what percentage of the employees that end up working for the acquirer leave to do startups again? Sure some leave to do startups again, founders especially, but probably not a majority of non-founders. Anyone have thoughts on this?



        1. Guest

          I hope my written response can do justice to my thoughts. Here goes …First, this reply is actually a reply that incorporates some thoughts regarding a few posts you have made but I will put them all here. I am going to put just some general thoughts down at the moment.So many folks say money is not a good motivator to start a business. It is better to be pissed off at to something, hurt by something, etc. So, it does not make sense that the risk of losing what has already been acquired by someone be necessarily a hindrance to starting one either, obviously depending on what is more highly valued by the would-be entrepreneur and his/her family.A mortgage and kids can also be a big motivator to start something though too. Right? To show your kids they have options, to build something with your kids, maybe to even pay off your mortgage.You did not make a comment in this area Grimlock but something you said prompts me to reply with a long-held thought I have about start-up finance. It is interesting to me the formula seems to works like this:Scenario 1: Hey, I am 22 I don’t have anything to put into the business but I will work hard and need 1 million to get my business idea up and running.Scenario 2: Hello, I am 38 years old. I have a house worth about $300K and a mortgage of about $280K but I will work hard and I need about 1 million to get my business up and running.Obviously, this is super-simplified. But ALL ELSE EQUAL conventional wisdom says Scenario 1 gets funding. By why? It does not need to be that way – unless of course the nasty truth that no one wants to admit is that a 38 year old cannot work as hard (or 45 year old, etc.). Why does the sub-culture of start-ups & start-up finance say the 38 year old has to put her or house on the line to make the business work when we do not require a 22 year old to do so? Obviously, having zero financial skin in the game does not really matter because if it did the 22 year old would never get funded as they have no financial skin to give yet – unless they are a Trust Fund baby or something.So, it is curious to me why so many believe, and others perpetuate, an approach towards start-ups that seems just faulty to me. Again, this exercise assumes all else is equal, which in reality can be the case (i.e. both the 22 & 38 year old have a strong technical mastery, leadership, product idea, etc.).

          1. FAKE GRIMLOCK


          2. Guest

            Absolutely, the paths can be different. I am not sure I understand the TechCrunch comment as I do not really read TechCrunch.Oops, I think I posted my initial reply in the wrong place.

          3. Charlie Crystle

            age=success is bullshit.

          4. DavidSandrowitz

            EXACTLY! This is what I’m trying to get at. Why is there this expectation? When you are 22, there is little to no risk at all. But, when you are 38, you are expected to put everything on the line to show commitment…which is absurd. Risking your home, your income, potentially your marriage, and your children’s future…that seems like a heck of a lot to ask when it is not asked of everyone. That seems to be too much to put on the table, in my opinion. Yet, there it is. Unless the 38 year old can build up a cushion to rely on or find a way to generate revenue early on, it seems like the deck is completely stacked against them. 38 year olds would be better off selling their ideas to 22 years and keeping a minority stake in the resulting company. Or, at least it seems like it.

      2. DavidSandrowitz

        Available to startups, sure. But, founding companies and trying to bring ideas to fruition…that is the question. Do the 35 year olds have no idea or no chops? Is there a bias against them in the system? Is it that they’ve all become complacent or that they simply cannot build a company when they’ve got spouses and kids and mortgages and, frankly, might need a bit more sleep than your average 22 or 25 year old?What of those 35 year olds with ideas and a bit of a shot (some time and a bit of $$$ to use)? Is there a bias in the ecosystem against those folks who are trying to do it for the first time at that age? Do they have enough “rock star” about them to attract talent, investors, etc?Or, is it all about the idea? Honestly, if you can execute, none of this should matter…but it does, doesn’t it? When you look around, you just don’t see many first timers that have are 35 or 38 (or whatever) and trying to make it happen. I know a few, but there are not the average. And, if this is the case, the question is why and whether this is ultimately a bad thing when it comes to starting and growing successful businesses.

        1. andyidsinga

          a lot of good questions there. i think there is generally just a small pool of people who are willing to start companies. it also seems that more unemployed people try to start businesses than well-employed. So since there are more young unemployed people you see more young founders. None of this putting any value judgement on old,young,unemployed, well employed = having a very good quality, well paying job at a successful and stable company. it takes A LOT to get a good person out of one of those companies. Joel Spolsky talks a bit about this in his posts ( here http://www.joelonsoftware.c… about recruiting ..part of his solution is to recruit young and groom good employees ..other part is simply recruit rather than hire off street.



      1. Charlie Crystle

        bs, again. it doesn’t take 15 years of thinking about something to take action on it and create success.People–if you want to start something, start something! It doesn’t matter if you don’t have capital, it doesn’t matter if you’re 7 or 70. Yeah, that informs your path, but it doesn’t define your success.

        1. FAKE GRIMLOCK


          1. Charlie Crystle

            15 years.Ok, yeah. Subtext in my head working overtime

          2. FAKE GRIMLOCK


        2. Brian

          Name a 10 companies that started up with NO capital.

          1. Charlie Crystle

            I only know what I know.Chilisoft. Mission Research. Jawaya.

    4. fredwilson

      i think you can do it for the first time in your 50sit is harder for the reasons that andy points out belowbut erick (somewhere else in this thread) is just now working on an idea he’s been thinking about for over 15 years and he’s past his 20s



      2. Miljenko Hatlak

        Fred, yet another great post, as always.Last summer, my co-founder and I have started our “journey” into the start-up world. Technically speaking, we’re not start-up yet, since we didn’t officially registered our company. We are leaving it yet till we finish our minimal viable product /prototype/.Specifications of technology we are playing with has emerged somewhere in year 2000, (when I was entering into my 30s). Unfortunately its adoption has took another ten years, because development of relying technologies and internet infrastructure in general wasn’t capable to support her.Now, ten years later state of development of this infrastructure is slowly coming to satisfactory level.When we realized that our old ideas could finally be realized, and that actually none of major players in our future market didn’t come out with at least similar product (some of them actually tried but pivoted into other direction), our immediate conclusion was – let’s try to do it now.In case of failure, one day we won’t blame ourselves for not trying to start a start-up (and just to prove our idea) .We are doing this from Croatia, with zero outer investments. Meanwhile, we’ve stepped into our 30s and 40s …….. so what?Every other step is like another “mission impossible”, but challenge to pass it keep us focused in our “mission”.

  11. Phil O'Brien

    Hi Fred. Just discovered your excellent blog. After selling a UK media business successfully a few years ago – I’ve been working out whether my next step out of “funemployment” would be a start up. In my musings, I used a similar “band” analogy about Pink Floyd and Dark Side of the Moon – I’ve since decided that I’m not going to create a start up – but invest and give time to start ups (many are in need of grey hair!). Won’t just be a Non-Exec, interested in rolling my sleeves and helping out in Biz Dev. Hopefully first investment will be in NYC – just down the road from you. Enjoy your writing. Cheers. P

  12. andrewparker

    For both entrepreneurs and rock bands, the phenomenon you are describing is survivorship bias.For first time entrepreneurs, if they don’t already have a product that has achieved some level of product/market fit that impresses you, it’s very unlikely you’ll take a second meeting, and the deal won’t move forward. The first time entrepreneurs need to have demonstrated that they’ve already built something people care about… if they haven’t, it’s tough to find a compelling reason to back them.For serial entrepreneurs, having a launched product in market with traction is not a dealbreaker. More serial entreprenuers receive funding off of just a powerpoint deck and their past history of success.So, survivorship bias… there are countless first time entrepreneurs struggling with the same product/market fit issues that the serial entrepreneurs are struggling with, but they are far less likely to get funded, so you don’t think about them as much, especially when you’re evaluating your own portfolio CEOs.



      1. Robert Holtz

        POW! Once again Grimlock cuts right through to the core truth.Love how you do that, my robot dinosaur friend! πŸ™‚

  13. Vijay

    Excellent explanation about difference between first time Vs Serial entrepreneurs

  14. Satish Mummareddy

    There is another reason an entrepreneur struggles the second time around, especially if they took 5-7 years to build a real company (instead of build a product and flip it in a couple of years).Most entrepreneurs have blinders on while working on their first startup. They are focused day in day out on the one problem sitting in front of them: the market they are in and nothing else. They do not keep up with the rest of the world as it evolves.One day when they wake up to think about a second startup, they are a year or two behind at least. They need to first understand the state of the art in a bunch of areas, take the time to find a few areas that is ripe for disruption with huge market potential, find one that they are passionate about and then come up with a solution.

    1. fredwilson

      yes, i’ve seen that happen

  15. markjosephson

    I think (and hope) there is also something to said about pattern recognition. So much of what first-timers see is brand new. After a while one tends to see that the problems aren’t always new, it’s just how you respond to them that can change. Second timers hopefully will have “seen it before” and can make a more educated decision. As to the band analogy, I think it still holds. Second albums that stray from patterns and formats familiar to their fans often stray.

    1. fredwilson

      pattern recognition is a big part of what i dothis post is, in fact, about pattern recognitionhow was the vacation mark?

      1. markjosephson

        Vacation was great! Thanks for asking. Great time with family and time tobe off the grid, the importance of which probably warrants a blog post ofits own!_____________________Mark [email protected]

  16. Ericlklein

    What do you think of found teams made up of a mix of both (1 successful serial and 2 first timers)?In our case the first timers were part of start-ups in the past just not running them so I am curious as to how you see this mix working.

    1. fredwilson

      zynga was sort of like that though Mark was the controlling partner. but he had a bunch of very talented first timers around him. it can work amazingly well

      1. Ericlklein

        HI Fred, Thanks for the response.I was wondering if you have any examples that are not consumer internet related? We are targeting the service provider side of the equation with a service based on product (or experience shows most carriers do not have the staff to do the in-house management and support).Thanks againEric

        1. leigh

          HI Eric,Having worked with and at major cable and wireless carriers here in Canada and in the US – i would say having someone with significant experience on the business and cultural mechanics of those organizations are key which to me = experience client side. I mostly work in the innovation area and many of the hurdles these Companies usually face are probably the very things that are going to make it harder for you to be successful.

  17. Matt Cordova

    “my favorite type of entrepreneur to invest in is the guy who just lost for two reasons. 1) he’s pissed off and out to prove something and 2) he’s learned on someone else’s dollar.” -Don Valentine founder of Sequoia Capital



  18. Jason Moy

    Remind me again why Fred Wilson is an authority on this? Has he actually done anything, or just signed a bunch of checks while flying business class and going on fancy vacations?

    1. LE

      Jason – Why not turn that bitterness and anger into something big because that is at least ONE way many entrepreneurs get motivated to achieve. I turned simple disappointment about my father in law controlling when we could use his shore place and boat into motivation to make enough money to buy my own.Fred’s “authority” by the way is based on his observation of the entrepreneurs he has described.

    2. JLM

      The world is made up of quarterbacks, coaches and owners.A QB has to be able to do it. Now. But he needs a great coach to teach him and to bring out his talent.The best coaches were once upon a time QBs but cannot or don’t want to have the ball in their hands but they know, oh how they know, what it was like to pump fake and throw the deep ball.The owner can tell the difference among the best talent and knows that a good quarterback with a great coach can lead to victory but also has to be prepared to replace both of them.At every level of the game, it is necessary to have good judgment. It is the judgment that guys like Fred Wilson have developed — regardless of how they developed it — which is valuable.Good judgment, the product of experience.Experience, the product of bad judgment.You might want to consider a charm school refresher, friend.

    3. fredwilson

      the only real job i ever had was writing softwaresince my mid 20s, i’ve not done anything other than sign checks



  19. capken

    Interesting article. I’m a first timer. Seems like I should find a serial who is more interested in building the company and happy to follow my vision for the product and strategy. However, I haven’t met any serials who didn’t feel that their vision for my product and strategy wasn’t superior to mine.I’ll give you a concrete example of this, I was on a show in Canada called “The Pitch”. Kind of like Shark Tank without the drama. I gave my pitch and then the panelists gave their opinion. The first comment was that I had a great market but that I was failing to see the gold. Her advice was certainly well intentioned and came through lots of experience, but was definitely off base. She doesn’t understand the underlying competitiveness of my market, my unique vision, or even the problem I am seeking to solve. This is an everyday occurrence for me, and I’m sure millions of other first time entrepreneurs around the world. I do not know 100% that I am right, but I am far more confident in my vision than what anyone else has presented as an alternative, so I continue to drive ahead with my plan.In case you are interested in seeing the video clip from “The Pitch”

    1. Charlie Crystle

      lead it yourself. you’ll figure it out.

  20. Sushrut Bidwai

    What I wonder is – Is some one who has done a venture completely different than current will be considered as a serial entrepreneur or not? For example – I did a services (outsourcing only for startups) venture before and now doing a product startup ( I personally find my previous venture very very different than current and hence most of the things I learned before are kind of useless now.

    1. fredwilson

      some skills will transfer but others will noti’d say it is valuable but not as valuable

  21. William Mougayar

    Agreed with everything you said, except the 3rd paragraph about where first time entrepreneurs might struggle. What you described is true if the first time entrepreneur is young or inexperienced, but if you have a first time entrepreneur with years of experience with other companies, big or small, they’ll most probably know exactly what kind of company they want to build and how to build it.There probably could be another analysis made between first time entrepreneurs- say under 30, and those over 30, or ones with a handful of years of experience, and others with 10+. There are plenty of cases where someone was No. 2 or No.3, and then they come out on their own and do extremely well because of what they have seen and learned.

    1. fredwilson

      great point william

    2. Ldodson

      It depends what type of experience the 40 somethings have had. If they have been spending their time at a fortune 500 company, they sometimes underestimate the effort to build a successful company. They usually have a core compentancy in one area or two areas, but often underestimate something they had very little contact with. Marketing and promotion is a common soft spot for former program managers. They build great products but fail at the promotion side of things.

      1. William Mougayar

        I’m not disagreeing, but this all depends on the person. What you describedis true for a non-founder who wants to move from a large co. to a start-up,and there’s a risk there- agreed. But a founder would be foolish not to knowwhat the differences are, and the smart ones will adjust and use thatbackground to their advantage when it’s time to scale.

        1. Ldodson

          William – I was over 40 when I started my first company, so I do agree with you, that it doesn’t apply in every case. :)Laura

  22. Raj

    The sophomore slump.The music business is replete with great startup metaphors.

    1. Guest

      It absolutely is!

  23. ShanaC

    Well, how do you get over the worst of these humps? What personal skills should someone develop that is the best of all worlds?

  24. Nick

    Love the blog. What changes in your method of evaluating companies when they are not in the USA?

    1. fredwilson

      same exact method but the hurdles are higher because the distance is a hindrance

  25. Barbara Pantuso

    I too just finished reading and commenting on the TC post this morning on the relationship between age and success. Stumbling across this post restored some faith for me – faith in sound reasoning and against snap judgments. I appreciate you stating that these are generalizations. Second and more importantly, you recognize the value that BOTH the first-time and the serial entrepreneur bring to the table. If there is one thing I have learned in my career, it’s that it takes a team of diverse skills, experiences, and perspectives to make something fly (and fly well). Someone with fresh eyes and someone knowing the ropes make for a powerful force! The entrepreneurs you work with are lucky to have you recognize this and to help fill the gap.

  26. LECHSAM group

    A definite takeaway from this post is the need to be proactive… aways be looking 2 steps ahead. It is worth explicitly stating that a good dose of optimism works wonders in preparing yourself (and your startup) for the future.A different spin on the rock band analogy is: Never forget the “fan base” (customer) that made you successful… The myopic short-sighted focus on maximizing dollar returns (at the expense of current audience) is a key reason for a lot of the sophomore album blues.

    1. fredwilson

      “never forget your fan base”great advice

  27. George Lucas Bowen

    There is a lot more depth to the musician analogy.1) Artists/Bands have iterated for years before their break out album. They have written, recorded, performed, gotten feedback, and repeated. All in a safe sandbox of local or regional fanbase. They have failed and learned without really publicly releasing the failures.2) Their entire life experience goes into that breakout album. They are living in the trenches everyday getting their face kicked in and fighting back putting that emotion into those songs. That emotion is transparent and fans can immediately connect to it.After a big breakout they lose touch with how they got there. Most can not put themselves into the creative mindset to re-create that emotion or energy. Some artists can channel that energy though. Eminem is a great example. He has nothing to fight against after his first success. Being poor, white and in Detroit, all changed after first album but he kept bringing the intensity and fight. Another good example is Madonna. She was able to Pivot with each album and re-invent herself. New inspiration to keep creating great music.

    1. Guest

      Yes, I think you are spot on and agree about iterations/recording/feedback/etc. However, you lost me at ‘Pivot’, which has become the ‘newest’ old word in use by the startup community. Please someone come up with a new word fast … please.

      1. George Lucas Bowen

        I’m sorry pivot is overused, it’s just faster to say than ” One foot planted with the other moving to a new space”. Artists have 3 choices in their career. 1) don’t change keep making the same music over and over, appealing to same demo 2) stick to your core fans and progress with them as you put an album out every 2-4 years your fans age and life changes 3) Pivot with one foot planted to keep their core fans, the other stepping out to a new space to grow creatively and fan base.Eminen has stuck to the same routine and it’s worked. Madonna chose to pivot I suspect due to a big international fanbase and does more dance music to appeal to them, and it’s worked.Serial entrepreneurs have the same choices. Say you have your big break in ecommerce. After that do you: Only make ecommerce products, or go from ecommerce to maybe mobile payment solutions, or go from eccommerce to iPad video apps because you are passionate about that now. Comparison of Steve Jobs and Jeff Bezos, although Jeff has kinda done all 3. Amazon, creating Kindle, and EC2.

        1. Guest

          George,No need to apologize. I am totally with you about 100% regarding the ‘artist’ choices. In my opinion, ‘pivot’ is just the startup equivalent of the Top 40 hit that has been played too much and is used to try and describe anything and everything.



    3. Harsh Patel

      Most of us at moodfish are musicians, and the music analogy makes complete sense! As a DJ, I thrive on ADD – put something out there, see how the crowd reacts and make the next step from there. I see people as living in the now and am hesitant to look too far forward. Our developers (actual instrument musicians who used to tour) on the other hand, definitely want to take a more iterative approach to the future of our company. Build > Test > Iterate > Release EP > Build > Test > Iterate > Release LP.

  28. Bill Ferretti

    Fred, you absolutely nailed it, and you did it with brilliant story-telling that employs a powerful metaphor. I like the metaphor you chose (the band) because it demonstrates the importance of the creativity, imagination, and artistry essential to start-ups. Whether it’s a killer app or a second novel after a bestselling first one, the successful serial entrepreneur is an artist. Congrats on a thoughtful, new (to me anyway), valuable insight.

  29. Jebb Dykstra

    Fred’s article and Michael Arrington’s articles both published today are in sync. From different ends of the telescope with Fred’s 1st timers vs. serial (Fred) and Michael’s young vs. old entrepreneurs. Very good take on the type of entrepreneur that will be “bankable” from an VC investor perspective. Like Fred concluded his article with — these presumptions are just generalizations. If an entrepreneur can’t overcome this, then he/she is doomed anyway.

  30. BradDorchinecz

    Curious of, in your experience, which type of entrepreneur tends to take more risk – first time or serial?I can think of arguments for either: first timers because they aren’t yet aware of the odds against them (ignorance is bliss); or serial because they already have been successful, have money in the bank and now are swinging for a home run.And this also begs the question – are entrepreneurs who built the biggest companies those who took the most risk?

    1. JLM

      Great question with maybe no real answer.First time entrepreneur is really not sure what the real risk is. He does not really know where the risk frontier lies.Serial entrepreneur has done it before and the risk frontier is a bit farther out. Walking on the high wire is not risky if you know what you are doing.Risk is also a function of whether it can kill you or not. When it can’t kill you, then sometimes it IS the opiate which makes you an entrepreneur.

    2. fredwilson

      first time takes more risk at the start but often the serial entrepreneur steps up the risk faster as the business gains tractionand i do believe the best outcomes are highly correlated with smart and agressive risk taking

      1. BradDorchinecz

        I’ve heard others say that’s why they don’t mind letting the entrepreneur take some chips off the table in later rounds – it encourages them to continue to take calculated risks instead of just protecting the value they’ve built to that point.

        1. fredwilson

          totally agree

      2. BradDorchinecz

        I’ve heard others say that’s why they don’t mind letting the entrepreneur take some chips off the table in later rounds – it encourages them to continue to take calculated risks instead of just protecting the value they’ve built to that point.

  31. Ivan Vecchiato

    You are referring to music more and more every day, I like this metaphor and I’ll stick to it. A band that has been playing the music with real committment is not going to plan a tour and the commercials for their records, a management staff will do it. Shouldn’t be the same for first time entrepreneurs, by means of incubators rather than VCs? They should let the newly born company to focus on projects and run legal issues, recruiting, and other mess for them.On the other hand the founders will not learn how to build up and grow a company. What do you think about incubators?

    1. fredwilson

      incubators is a word used to describe many things. i don’t like them as a general matter but there are specific instances of them that i do like

  32. Monroe Jones

    This is great, I can’t believe you went to the first album, second album scenario. As I started reading the blog, I went there in my head and was about to make the comparison. I experienced this first hand many times with the artists I worked with over the yearsβ€”the dreaded sophomore effort. As I jump in to my own thing here (, and learn from you guys, the similarities are amazing. And maybe I’m feeding off of the excitement I used to feel in the music industry, but it’s trueβ€” great VC’s are like great A&R men used to be, recognizing talent, cultivating, challenging and nurturing great new artists. And entrepreneurs, well, they’re the rock stars. Sorry to be so corny, but there it is.

    1. fredwilson

      and that is exactly what the VC who I was with when i thought this up said to me. almost verbatim.

  33. MartinEdic

    Having done both (original bands and serial start-ups) I think you’re spot on. I would add something to the band analogy though. I was in a band that made seven LPs in the eighties (never mind, you haven’t heard of it) and the way we developed a body of work was constant writing. We didn’t go out and only play the songs that people were familiar with, we tried out new stuff all the time. And we obsessively did this all the time between gigs.A successful serial entrepreneur should be viewed by their body of work. It may not all be good but if it reflects constant experimentation and growth in sophistication that is something unique. Think Radiohead, where each project expands their range exponentially.Entrepreneurship, IMHO, is a process of constant iteration: Develop/create, put it out there, get feedback, pivot and/or refine, etc. First timers live on adrenaline, serials live on the process. Which is what Fred said I guess!



    2. fredwilson

      totally agree martin

  34. LE

    “And then they have to go back into the studio and write and record a second record in a matter of months. It is no wonder that is is terribly hard to produce a second record as good as the first.”In addition to the time frame you’ve mentioned, the lack of hunger and need also contribute to this greatly.Creativity and motivation can come from psychological pain. If things are to rosy it makes it harder for many people to be creative.An example of this would be the Dixie Chicks album which won a grammy after the whole George Bush Texas remark fiasco which caused their sales and fan base to drop initially.By this theory of course it might mean that it is easier to create a success after failure than success after success.



      1. Eunice Apia

        What About Start ups who are hungry for success and want to solve a problem?I think you need both attributes. You need to think big as well as want to solve a problem.

  35. Statspotting

    “We invest in both and do not have a preference betweeen the two. “I remember a post from you Fred, where you mentioned you prefer people who will go for the home run or something like that (serial entrepreneurs)

    1. fredwilson

      yes, but first timers also go for the home run.look at zuckerberg, for example

  36. Jon Kelly

    I felt like this fit me well. First time for me was huge passion for the product, huge number of mistakes building and managing the business. Second time it took about 4 years to find product/market fit before nailing it with a fantastic team and then a great exit. Third time is ongoing, hoping to get there a bit quicker this time!

    1. fredwilson

      i’m sure it will go quicker.

  37. Pete Griffiths

    shrewd piece.

  38. David Semeria

    But I remember reading that you will only invest without traction if a serial ent. you know is behind it.So, USV is really all about traction (and there’s nothing wrong with that).Is this correct?

    1. fredwilson


  39. samfjacobs

    The problem with aerial entrepreneurs is that they get to raise money at unreasonable valuations, in my experience. Have you done any analysis on which produce better outcomes? I like the idea of a first time entrepreneur with a serial operator. Best of both worlds.

    1. fredwilson

      we do pay more for investments run by serial entrepreneurs and the success rate is not materially different. but when serial entrepreneurs get it right, they can really step on the gas and take over a market. mark pincus/zynga is a great example of that. i think the increase in valuation is worth it

  40. paramendra

    The first time entrepreneur should hire a serial killer, I mean entrepreneur, for COO. πŸ™‚ One tech entrepreneur I know – same ethnicity, same district in Nepal – sold his company to Sun over a decade ago for 100 mil, and has struggled to launch a second hit. Last I heard he was working on a candy factory!? Talk about going offline.

    1. Guest

      Yes, but candy tastes good and is demanded by a great many. So, I am not sure I see your point.

  41. navarrowwright

    FredGreat post!How do you view a second time entrepreneur who did not take his company to exit? Some people say the second time will be harder for them as a “failed” entrepreneur while others would say that experience was extremely valuable. What’s your take?Thx

    1. fredwilson

      failure is good. i’d back a failed entrepreneur in their second outing as long as they have a great idea and exhibit intense passion and comittment to it

  42. Nikkki

    The concur with the differences that you have observed. I can’t agree more.

  43. lazerow

    I imagine the same can be said of first timers and second+ timers in many areas. Take marriage, for instance. First marriage is all passion. You’ve been stewing on the idea of getting married for a while. You jump in. It feels right. But you really don’t know how to get it right and the skills that got you married are not the same as the skills to stay married and grow the marriage. The next marriage is less about passion but more about finding the right fit and working at it.I post this as a 4-time entrepreneur and a first-time husband married to my 3-time cofounder. So please disregard the comment above.

    1. Guest

      Hah! Great post.

    2. fredwilson

      imagine if you could build your first company for 70 yearsthat’s what i’m trying to do with my first marriage

      1. Guest

        hah, another good reply to a good reply

    3. leigh

      lol except of course that start-ups (if they are successful) are closer to “honey i want to spend the next 8 to 10 years with you”

  44. Sufiy

    Guys we need your help in electric cars space! Social media is great, but what are we going to eat and how will we drive with gas above 10 dollars?It is time to bring rock-n-roll of VC culture into the electric space.Watch the best video on peak oil and Shai Agassi interview after it.

  45. J Nicholas Gross

    Very insightful analysis, thanks for the perspective

  46. mcenedella

    I think the real advantage is being the serial Venture Capitalist and knowing what questions to ask either flavor entrepreneur in order to understand if they can shore up for their deficiencies!This is my 2nd time as CEO, but first time at scale, and I’ve pondered quite a bit about the differences between what I would do if starting again and what I actually did when energy, pith & vinegar were all that I had. Pluses and minuses to both, and only with wisdom do you know which is which.

    1. Rod

      Marc – I love the newsletters you send out – they are very positive and the certainly help to keep your company in my mind. Great job!

      1. mcenedella

        Thank you very much Rod! I just wrote my 400th weekly newsletter for delivery tomorrow πŸ™‚ As long as people keep loving reading them, I plan to keep on loving writing them!

    2. fredwilson

      touche πŸ˜‰

  47. Chris Dessi

    You invest in both first time and serial entrepreneurs, and mention you don’t have a preference, but I’m curious – has their been an equal distribution of funding or have you invested more heavily in your proven, more seasoned serial entrepreneurs? Can you discuss why, or why not?

    1. fredwilson

      i don’t have the answer to that and some of the investments will be hard to classifyis twitter a first time entrepreneur (jack dorsey) or a serial entrepreneur (ev and biz)?but my guess is that the dollars map pretty closely to number of deals

  48. Andy

    Loved the second album analogy. As always an interesting post.

  49. Weathervane Music

    Your analogy is right on the money, I can tell you, as a musician and record producer, first, and now a social entrepreneur. For years, Fred, I’ve been interested in the thoughts of the VC community (Betaworks, is particularly inspiring to me) because I love the clarity, focus and direction, … not to mention the obvious premium for including “meaning” and “greater purpose” as valuable factors in projects worth supporting. I founded a non-profit called Weathervane Music (, and now I’m about 2 years into getting it off the ground. I’ll probably be a First Timer, and a “One Timer”, especially if we can make our idea stick.Anyway, I sometimes think that artists making a first record have different ideas for success than those making a second. My experience recording somewhere in the realm of 100 artists over the past 15 years is that far too few think of music as a business at all. The goal is to “be an artist” not “business-person” as though the two must be mutually exclusive. That, and the fact that there is hardly any industry left to “invest” in new artists, is some of why we started Weathervane.

    1. fredwilson

      interesting notions about art and businessi’d like to hear more

      1. Weathervane Music

        Well, I don’t want to get off topic too much. And the record business as a metaphor is probably more difficult for someone in my shoes since my whole career has been a lesson in just how non-sustainable a business it actually is. It doesn’t help that artists rarely want to think in business terms, and that the public doesn’t want to think of it’s role the process either.I really like that you mentioned “what kind of culture [entrepreneurs starting a business] want to create”. I’ve observed that the best and most successful artists I’ve worked with don’t have to consider their talent for writing and recording music. That is the given, and frankly, talent is not that uncommon. The uncommon ones always have an ongoing process or processes that naturally draw support in. Their success is community based at first, popularity-based next, and then hopefully financial at some point.I’d certainly love to tell you about what we do at Weathervane.

      2. Robert Holtz

        Anything done with mastery is art.

    2. Brian

      Mick Jagger was great as a rolling stone, had a head for business, but, when he went solo, and used his business savvy, his solo career was a flop. Richards was an artist with no biz savvy, his solo career flopped. You do have to have both business savvy and artistic vision in the entity but, never in the same person. It’s a team effort all the way in really successful music, that’s how labels evolved, they had he team to support the art and the vision to play just enough into the pop realm to fund and develop both. Artists that are business people are rarely the best of either and often end up failing at both when all the cards are tallied.

      1. Weathervane Music

        Brian, I agree on many accounts, even though I do stand by my assertion that artists do need to be solid business people these days.First though, I have a hard time when people like Mick Jagger and Kieth Richards are sited as representing any kind of norm. The vast majority of music being made is not by household names. True, efforts of the past have generally been teams within labels, certainly to varying degrees depending on what artists we’re talking about. But that has changed dramatically. Label support, at least truly effective label support in any financial sense, is reserved for artists who’ve achieved a much much higher degree of success nowadays, either previously or on their own.But what you’re saying does tie in very nicely with what we’re trying to do with Weathervane Music. We do believe that music community is the only thing that will make quality, enduring, culturally significant music possible. But “music community” has to be redefined as not just the artist and industry, as has previously been the case. It now has to be understood as artist and audience; people who make music + plus people love music enough to support it (and therefore “make music” as well).

  50. morefromalan

    Rock trivia: Some say the second album pressure is what put Darby Crash over the edge.

  51. David Cornelson

    I am a first timer still passionately focused on getting my idea of Interfactive Fiction out to the reading and puzzler masses. But at the same time I’m also focused on learning everything I can about building a business from the ground up.As for the next idea…I already have it designed and in my hip pocket, waiting in the wings. I come up with new product ideas regularly and often see them developed years later by other people. It’s why I became an entrepreneur. I know I see things in market’s week before their time.There are many first timers like me out there. The biggest problem is that the angel and VC world need to invest more at the first line high risk level to develop more talent. Stop handing gobs of cash to single companies and spread that cash around to hundreds of startups.We don’t need $50 million. We need hundreds of thousands or one million over a year or two. We need help funding our ideas and burning through the initial stage as quickly as possible. The more you spread the cash around, the faster you’ll find the best ideas and the best entrepreneurs.David Cornelson – Textfyre

    1. fredwilson

      i agree about too much money going to some companies and too little going to othersit is a structural issue in VCit’s easier to invest $40mm in one company than $400k in 100 companies



  52. andrewwatson

    I’m hoping my second works out better than my first because… well the first one didn’t work out so well πŸ™‚

    1. fredwilson

      i hope so tooand i bet it will

    2. Charlie Crystle

      choose to kick ass and you’ll be fine.

  53. JLM

    What is missing in this discussion is not just the ability of an entrepreneur to simply create a great product or to build a great company around that product or the ease with which a seasoned entrepreneur is able to do things the second or third time he has undertaken such a challenge — it is the ability to create a “winning culture” around both the product and the company. And around the entrepreneur himself when he is wearing the mantle of the CEO.Culture eats strategy for breakfast every time. Give me Special Forces before the best straight leg infantry unit in the world.In many ways, it is company culture — at the tribal level — that drives success. This is what I observe about Apple. They have good products. They have great culture. They have an extraordinary tribal leader. It is personal.Culture is not just what you do, it is fundamentally HOW we do things and how we bind ourselves to the tribe that possesses that culture.Serial entrepreneurs bring more than just a whiff of a culture of experience, knowledge, worldliness and competence.People will follow someone who has been to the rodeo before they will follow a neophyte.Culture eats strategy for breakfast.

    1. Guest

      I understand your viewpoint about the power of culture. And, having been in both large & small organizations, the power of culture is no less relevant to one size or the other. However, why can’t a first-timer be a creator of great cultures? Your example of Apple fits this actually, I believe. Granted I understand the point that it might be harder for folks to follow a First-timer into battle but that is an issue apart from the fact that a first-timer can actually build a great culture. Also, it is also possible for someone with experience (the serial entrepreneur) to be a lousy culture builder. If you have the time please provide some more thoughts because I am not sure I am getting what you are saying.

      1. JLM

        I do not suggest that a first time entrepreneur cannot be a powerful culture creator. It requires some thinking. Most first time entrepreneurs are focused almost exclusively on the product. They have almost no time for thinking. It is not age — it is life experience.Some men and women are thoughtful at 28 and some are not thoughtful at 50. It is what you have lived through which informs your intellect.In many ways the entrepreneur IS an entrepreneur because he IS willing to confront what he does not know. He nevertheless is willing to forge forward. It is what we do not know we do not know that kills us.I think this is particularly true today wherein I think nobody has 20 years of experience — we all have one year of experience 20 times. The world is moving very fast.You must be a very good communicator to be a culture sponsor or culturista.In many ways the culture is the glue by which the entrepreneur holds together the organization thereby injecting leadership into what is otherwise the almost exclusive province of management.It is all connected.

        1. Brian

          Maybe it’s not life experience but something much simpler, something young people already possess in buckets: the ability to communicate a vision and a goal, an overarching perspective and goal that all can sign on to completely, and do that by speaking into the way their employees listen. Someone said something of value earlier, they didn’t know what they didn’t know, that’s what you want all employees to understand at the outset of employment, that there are the three spheres of consciousness they normally operate in:1. you know what you already know,2. you know what you don’t know, and then 3. what you don’t even now that you don’t know, the last of which is the most valuable. Then you have to flesh that out with examples, that their past experiences inform their future actions, like fleas in a jar with a lid, they only jump so high, even when you take the lid off they don’t jump out even if they could, or that bacteria didn’t exist until they were discovered and that gave those with that knowledge an immense amount of power.Then you deprogram “right and wrong” and put in “works and doesn’t work” as new replacement vocabulary, because effective communication requires specific vocabulary.

      2. Brian

        Steve Jobs was a first timer.

        1. JLM

          Agreed but remember he also got kicked out and returned to save everybody’s ass. He had grown.

          1. Robert Holtz

            Agreed. He was the first timer that had the vision. But he returned as the seasoned entrepreneur who also had the outside perspective of where Apple had gone wrong.



    3. fredwilson

      wow, that’s more controversial than much of what i write JLM!i am sure many will disagree with youi think both are so critical and both come from the topthis is a topic i’d love to hear more from you on

      1. JLM

        The culture of a company informs every decision that a business makes. Once that culture takes root — its values, folklore, principles, savoir-faire, style, manners, consideration, work ethic — every decision thereafter is colored by that culture. Some decisively and some tangentially.Strategy is fairly obvious. It is very easy to get the big picture right. The application of a refined culture makes it easy to make big decisions good decisions. It becomes reactive rather than quizzical.Witness the recent Berkshire Hathaway dust up. It was the misapplication of the culture of fair dealing, transparency and the avoidance of even a whiff of conflict of interest that Buffett and his lieutenants failed to apply. Once they caught their breath, the culture had the answer even before the question was fully framed. You don’t crap where you eat.Immature enterprises have not codified their culture and perhaps not surprisingly. It may take a bit of time to develop a bit of culture and to recognize it for what it is.Visionary leadership, refined/defined culture, competent management and painstaking planning are the four legged stool which allow a great product to become a great company and a great company to become a great success.

        1. ShanaC

          would you say culture is generational then, and can be transmitted across ceos/time

          1. JLM

            The principles of cultures are timeless — honesty, integrity, customer focus.What changes is the application and the frame of reference as applied by each generation.Some time ago I read that some enormous number of college students admitted to cheating. I was floored by the number.I had gone to a military school and its honor code did not allow cheating or tolerating cheaters. It was an honor code violation to observe cheating and not report it.This was further compounded by the fact that I studied engineering which is fundamentally an “open book” course of study.When we took our final exams — which were simply distributed and no times was prescribed at which they had to be taken — we were allowed to use our textbooks, our own notes and any reference materials we had developed during the course of that semester. We could not use any library reference materials or somebody else’s notes or to converse with any person.If you are designing a runway for an airport, it is not very easy to “cheat”.So I think that culture is constant in principle and has a changing frame of reference as practically applied as the times change.

        2. leigh

          hey JLM – i’m going to use a quote about culture from you in a presentation i’m writing. I can’t find any link from your disqus profile to a bio. How would you like me to refer to you?

          1. JLM

            Anonymous blowhard from a big deal to me. Good luck.

          2. leigh

            lol ok you will soon to be immortalized as JLM avc commenter (i left out the blowhard part)

          3. leigh

            here you are in all your glory – (your quote is near the end) Β…Β 

      2. William Mougayar

        I agree with JLM in trying to say that culture can stand in the way of getting things done.Codifying the culture could be as simple as writing 5 to 8 principles that are lived and breathed. Culture can be molded by the CEO, but it must survive him/her if it’s real.

        1. JLM

          What you are referring to — in my mind — is the transformation of a group of people into a tribe.A tribe believes the same campfire stories, the same folklore, the same values and will focus that “knowing” on whatever it does.When tasked to do something, they will be able to spring into action quickly as they do not have to be persuaded as to the intellectual basis for what they are doing.There is a reason why it was US Navy Seals who got Bin Laden. In the whole world of special operations, there is a reason why they were the right tribe.

    4. Charlie Crystle

      So your next post: how to create culture.I’ll say you should create a framework of principles that informs vision, planning, decision-making, and execution and stick with it. And be kind.

    5. leigh

      Culture is strategy when done well πŸ™‚

      1. JLM

        Culture is everything when done well. That is the secret.

        1. leigh

          maybe we are talking apples to oranges. how are you defining culture? the reason i ask is that at my failed startup, culture wasn’t an issue. we had an amazing team. great organizational culture that was fed from the dna of our brand in everything we did. But i can give you at least 5 key strategic mistakes that contributed to our eventual downfall.

    6. PhilipSugar

      I agree completely.I think that’s the one thing that people didn’t think about when HP got rid of Hurd. I think it was more for the destruction of culture than anything else.Culture is very powerful and set at the top. If the CEO flies first class, stays at the Four Seasons, and spends money to attend self aggrandizing conferences. The culture is set.Same if she doesn’t respect development, or looks down at sales.I’m with you JLM give me a team with great culture every time.





    1. fredwilson

      yup. i posted this and then went out and enjoyed a lovely spring day and am just now getting to the discussion. suboptimal but it’s been a long winter!



        1. nzben

          Aha! Fake Grimlock must be in Auckland, New Zealand. It is raining here.Occam’s razor biatch.

          1. andyidsinga

            that is the sweetest use of occams razor and biatch eva! rock on ben πŸ˜‰

  56. Gregory Magarshak

    Hey, Fred. You are basically writing about me! I’ve been building and refining the technology for over two years, with a rather obsessive vision I guess. Now I have a team and a company and we are executing our plan and have two products that people love already. But we’re holding off on the viral until the scaling architecture has been completed.I would like to meet up with you at some point and show you what we have done. We don’t really NEED venture capital to survive, since our company is already bringing in rather good revenue per user, but once we start the viral features we’ll probably need guidance and connections. In any case, would love to finally show what we’ve been building! :)Oh and I got an android phone finally, to test it with.

    1. fredwilson

      where are you located?

      1. Gregory Magarshak

        NYC. Hunting around for a sunny office right now. Most of us are working from home. Could just meet up for coffee and show the platform we’re making — it’ll be another month until launch.

        1. ShanaC

          Actually, I have a name for a good broker if you need a sunny space…

          1. Gregory Magarshak

            Does he deal specifically in sunny spaces? πŸ™‚

          2. ShanaC

            he deals in spaces that startups love, actually he helped one of Fred’scompany’s find a space, though I actually know him socially and not throughtech land. Email me at shana.carp at gmail and I would be happy to make anintroduction.

      2. TG

        I’ll answer for him,”anywhere you are open to meeting me with a small heads up”—Best of success to you Greg…

        1. Gregory Magarshak

          LOL well I believe that if both people want to do something then it happens. It’s no good when only one person wants it. If you are chasing VC money then you are not creating enough value in your company yet as an entrepreneur. Of course, I might be on a high horse, but that’s the way I see it. I want to be proud of my company as an investment vehicle, so I am basically working full-time on making it even without VC. (See for example Calendar here: – that was taken today) That said, VC can accelerate the progress, so if it makes sense, I might do it. πŸ™‚

    2. Charlie Crystle

      VC isn’t about survival. It should be about acceleration.

  57. Peter Sullivan

    This post correlates to that other post on hacker news about 25 being the peak age for consumer web founders. I think your statement about funding both categories might be honest but is skewed. I can guarantee it’s a shit ton easier to get in a room with you guys if you have been on the road before. From my little experience I can tell that someone doing it a second time will be smoother. I always loved the idea of after failing the direct action does not need to succeed but to just fail less.This also always reminded me of a philosoraptor meme I saw on reddit that described first time job searching “if all jobs require previous experience, how am I to get that experience.” something to that effect.

  58. Sean Weinstock

    Question I’ve always had: Why don’t artists record tracks to put on their second album along with those they want to put on their first? Granted, albums usually have a different feel and/or musical direction from one another relating to the point in life the artist/band finds itself in, but it seems rational to record hits that front both the first and second album even if they don’t necessarily fit with the overall feel of the subsequent album. More thoughts/questions on this if anyone’s interested in talking.

  59. Greg Shelton

    Wow, what a great post. If you would divide entrepreneurs by their personality types the post title could be – Introvert Entrepreneurs vs Extrovert Entrepreneurs.Introverts are tend to be reserved and quiet and they are obsess about the idea 24/7.Extroverts are more outgoing and talkative and they are usually terrific at building the company.Introverts could be a serial entrepreneurs though.The best case scenario is when start up team consists of Introvert and Extrovert

  60. Gordon Bowman

    Another point about first time entrepreneurs is that since they have not yet had success (and the luxuries that success brings), they will likely be much more hungry. And they’re determined to put their heart and soul into the company in order to make it succeed.

  61. Eric Brooke

    So to take your generalizations a little bit further.I think that the your ‘First Time’ seems to be someone in their 20s.I heard a stat, time and time that the average entrepreneur was 40 years old. For someone in there 30s to 40s they are very likely to have thought a lot about what company they want to set up along with what they do not want replicate. They have had bad bosses and hopeful good bosses. They are also very likely to have recruited and managed. Now the organization leadership is the one they may have not done yet.That said I acknowledge that because I am building a startup that crosses psychology, talent management and recruitment.. Matching a job seeker to boss. That said I think a lot about the kind of company I would like to buildFor me I have had to learn product management, a large amount of software development and online consumer behaviour along the way.A trend that I am seeing is gunslinger entrepreneur vs collaborative entrepreneur.. modern bootstrapping entrepreneurs are working in partnership with other startups to build a better and bigger product, where the old style gunslinger will do it all on their own.

  62. Guest

    Absolutely, the paths can be different. I am not sure I understand the TechCrunch comment as I do not really read TechCrunch.



      1. Dave W Baldwin

        Just a matter of those that are transfixed on what is ‘big’ now and think it will be that way 18 months from now. Somewhere, the real disruptive will raise its head…

  63. Nick Rowney

    Interesting post and points.Comments, well I liked @Charlie Crystle but the rest would seem to be bullet points garnered from other peoples experience.What no one seems to be addressing is the requirements needed in order to succeed, these are psychological and have nothing to do with a product.So what you look for in an entrepreneur is their ability to work collectively, to embrace change, to pick themselves up after the big crash (resilience) work smart, network and understand what strategic opportunity looks like and how to make it.And so many more traits that make up successful people, I don’t care if it is your first or 7th time what I care about is you.

  64. Cameron Brain

    Fred – Great post. Was just reading a post over on TechCrunch today regarding a conversation Steve Gilmore had w/ a VC in which the VC stated that entrepreneurs are basically past their prime at the age of 25. I’m 28 and working on my 3rd web startup, 2nd to be funded. As you state, I’ve kept doing this mainly b/c I couldn’t imagine any other way to work.All that said, I have spent a fair amount of time thinking about the future and the role of age. I’ve never worked in the Valley, however it seems there is an unhealthy bias towards very young entrepreneurs. Perhaps it’s just a product of funding the cutting edge. As a follow up post, I would love to hear your perspective on age; the differences between yonger and older entrepreneurs.

  65. Siminoff

    Fred you post really had me thinking today, I could not get it out of my head. There was one thing that I disagree with. When you say that serial entrepreneurs “start the second and third and fourth company because they love startups and they don’t know any other way” I think that you are missing a key ingredient, passion.What should drive a serial entrepreneur to be serial is that they have a passion to do something great, and that passion is typically best met by starting successive companies. The guys that I know that have made the most money and are truly successful (happy) in successive companies understand what their passion is and how to work on something that feeds it.I used to think that I kept doing this shit because of what you said above, because I love startups, but I have since figured out what really makes me tick. And I think by figuring that out I will not only be able to do more successful startups in the future but also enjoy them more.

  66. csertoglu

    Good topic Fred. In the Turkish market, the story is a bit different. We find it easier to work with serial entrepreneurs since they know how to work with investors. They have seen the lifecycle. The first time entrepreneur is more of an unknown quantity. We, of course, work with both but the lessened risk with serial entrepreneurs is hard to ignore.

  67. Youssef Rahoui

    One of the big differences is energy. When you found your company at 24, you are full of energy, you have nothing to lose, you are optimistic, you are fearless. Shit happens but you get over it.When you found your company at, say 34, you have less energy, you may have a GF or a BF, you have a flat, a car, etc. Shit may less happen to you because you are more experienced but the drive is usually not the same. If you have been successful at your first company, you may even be a bit cocky or complacent.So, from an investor or an early employee stand point, you may not look at the same things before joining the startup.

  68. Ankit Agarwal

    So would you say it might make sense for a first time entrepreneur to work along with one who has done it many time befores? Since they would then have complimentary skills.

  69. primefurniture

    There’s the steady, bright, business-oriented one; each of her companies will do well because she’s committed to building great companies and is methodical in doing it.Office Furniture

  70. Dave Pinsen

    So why not pair first time and serial entrepreneurs together?

    1. Dave W Baldwin

      Congratulations per the tweet Tereza sent out Dave!

      1. Dave Pinsen

        Thanks a lot, Dave.(For those who didn’t see the tweet, it was of one of the two screen caps posted here: Portfolio Armor iOS Update).

  71. olivierrosset

    i’d say that the third album is harder than the second album. if first album did well, second album is then often an re-affirmation of the first one with less DIY and more money. but the third one is when you have to reinvent yourself while not turning down the original fan base. tricky.

  72. olivierrosset

    i’d say that the third album is harder than the second album. if first album did well, second album is then often an re-affirmation of the first one with less DIY and more money. but the third one is when you have to reinvent yourself while not turning down the original fan base. tricky.

  73. Phil Simon

    Great analogy with bands. When writing The New Small, I noticed that distinction myself: first time vs. serial entrepreneurs. Either way, props to those who start their own shops. It ain’t easy, but it’s sure fun.

  74. Matthew Gough

    The beauty is when you are a first time entrepreneur you don’t know or particularly care about the risk, it is easier to do when you are 22. As a serial entrepreneur, I understand the risks and what is required to take an idea and make it a successful company- for that I believe that my passion is that much greater in my mid thirties. It is not about if it will be a success but the road map to get it to be a success. That creates a lot of excitement and passion around execution.

  75. innoblue

    What’s truly hard is for a first time entrepreneur to get meaningful meetings and interactions with those who can back them. It’s a tautological argument that VCs/investors use: e.g. show us traction, great product/market fit; entrepreneur: we’d show you more traction and a better product/market fit if we had a bit of seed capital to get to the next step. VCs consistently want entrepreneurs to show them huge numbers but not all great consumer internet products started bootstrapping for months and months until they had high usage numbers.The more interesting conversation is; even with the existence of tools like AngelList, etc. it actually makes investors MORE conservative on taking meetings, etc. not less — as now they have more tools to view more startups sporting fancy pitch decks and good numbers. What would be interesting would be how do you separate the signal from the noise for first-time entrepreneurs and find the best teams without a pre determined bias that you wouldn’t have for a serial/repeat entrepreneur?

  76. herve

    One short comment: I am currently studying the performance of 1st time vs. serial. You may find initial data in the pdf document on…. Out of 2’700 entrepreneurs (linked to Stanford), it appears 1st time do better and serial do well… in their 1st company and then worse and worse… something I had an intuition of as a VC and I am building now some statistical support!

    1. Dave W Baldwin

      Just as a philosophical note on that, the Serial was a 1st Timer and that probably means his 2nd and 3rd are connected to the first. That is why it grows stale.So when we reverse engineer on the human side, where a 1st Timer is looking at things truly forward to bring about the improved world and knows how much it will take in blood/sweat/tears… he looks patiently for those who have what it takes.Then you just put up with the crap from those w/o what it takes who want to keep doing a lot of the same. But patience wins in the end when you take the challenge of changing the world.This is what makes the difference between the 20 and 40-60 yr. old. The older person can place ego/vanity on the table and measure what drives the person being considered to join. The older person then has the armor necessary to put up with reaction from those who think it is all supposed to be simple.Otherwise, the comments about matching up different age groups is correct. This works as long as the younger is prepared to do logical arguments backing up an idea/ingredient the older may not realize is important.If both sides respect and believe in earning respect, then a lot can happen.

    2. herve

      sorry, I met one-time vs serial which explains why serial have 1st time too but one-time never another one. Indeed serial do even better than one-time in the first but not the following ones. On the contrary, they do much better with fundraising! (Slides 25 and 26) of the pdf

  77. Dave W Baldwin

    Good post…1) age doesn’t matter, it is the idea matched with the will.2) re music, the real song writer has already written past the first album, it more or less comes down to which ones work best. You are then able to look at the second as you finish out what you have started up. The real song writer gains inspiration from give and take with audience regarding what melody shapes and lyric genres go over best. Do that and you can put in the ‘safe’ and add a few that are more on the edge…on the edge breaking down into ‘for the hell of it’ and ‘what would really be good to have in the set list for the next tour’.3) word of advice for readers that still do the band thing… don’t tell the audience in the smaller venues the tune is original. Play it and measure reaction. Be low key in measuring and you’ll gain useful knowledge.

  78. Eunice Apia

    I’m trying to figure out which is harder; Getting Funds or Running the company. I say Funds.Im a first time Entrepreneur and I’m stuck on finding the funds that work for my company. There so many options that the answer gets lost in which one to choose or try for. It doesnt help when you lack “experience” or don’t have a prototype. :-)) So many strikes against first time Founders.

  79. bernardlunn

    Wonderful post, captures the differences very well. The great entrepreneur who fails at venture # 2 is common, I think of Steve Jobs with NeXt. But venture # 3 is then awesome. Methinks hubris is the real showstopper problem.

  80. Brandon Giam

    This is something every first time entrepreneur should read. I am a first time tech entrepreneur and this post is very true, especially the beginning about us putting in tonnes of time and effort in our first start up. I guess we want to get it right. Thanks Fred.

  81. EnglishKool

    It seems you are in the minority, especially true of the UK.As a first timer in London, with nearly 2 years working on my own venture, I am about to go back to (paying) work again to fund the next development phase that’ll take me to beta launch. I know I must take my product to the market before others work out just how valuable that market is and I can’t stop until I get there. My passionate belief is what keeps me going.But some angel funding would help…

  82. 8 Bit

    I apoligize if this has already been covered, but I think your reader’s would be interested in the infographic below.”Startups Exposed”…

  83. AndrewKnot

    Regardless of the type of entrepreneur you are, you’ll always be needing a professional business plan. This is why I have thought about sharing this great information I have stumbled upon here: http://www.businessplanjour…. Hope all type of entrepreneurs will benefit on behalf of it!



  85. paramendra

    8th album? Whoa, Charlie.

  86. JLM

    Damn there is a whole lot of blood, sweat, toil and tears in that post. I can feel your life force and it is strong. Well played.

  87. Donna Brewington White

    Wow, Charlie, another one of those comments of yours where I have to pause for a few moments after reading it to let it all soak in…the comment that keeps on giving.Seems like your bringing in the recent grads and adding them to the mix after stabilizing your team with the experienced developers is a lot like a VC portfolio anchored by the serial entrepreneurs, creating room for those fresh first-time entrepreneurs — who then serve as part of the feeder pool for a fresh crop of serial entrepreneurs. It’s a great ecosystem.Glad to hear from your comment below that you seem to have had a great week in the Valley.

  88. fredwilson

    their loss, our gain



  90. wfjackson3

    He was busy moving too.

  91. paramendra

    One thing. Can you please turn off the caps lock? Thanks.



  93. fredwilson

    blood, sweat, toil and tears is a good way to describe charliethat is a compliment

  94. Charlie Crystle

    It’s an amazing mix of blessings.

  95. Charlie Crystle

    don’t forget joy–lots of that too. I probably focus too much on the challenges, but there are so many amazing moments in startup life…maybe I need to do a post on that. Last week in the Valley was filled with them.

  96. Charlie Crystle

    the failures are part of the wins–let’s be honest here. The outcomes do not reflect the entire path.



  98. andyidsinga

    oh matt matt matt matt matt matt – i dont think thats gonna happen πŸ™‚ fake grimlock is a fixture! πŸ™‚ πŸ™‚ πŸ™‚

  99. fredwilson

    i disagreei find it adds some character to the comment threadsi personally enjoy it

  100. Charlie Crystle

    I’m looking forward to NYC this week–will be great to see the other great tech ecosystem. This is a lot of fun…

  101. Robert Holtz


  102. Natalie Sisson

    My favourite quote I use all the time.