Coming Of Age

I’m out here slingin bringin the drama,
tryin to come up in the game
and add a couple of dollar signs to my name
– Memphis Bleek Coming Of Age by Jay-Z

I'm not going all Ben Horowitz on you. But imitation is the finest form of flattery and I do like how Ben rolls on his blog and in the venture capital business.

I'd like to talk this morning about how hard it is the come up in the venture capital game. I work with a bunch of VCs who are in their early 30s and have less than five years in the business. They work hard, put in ridiculous hours, are on top of all the latest trends, companies, technologies, etc. They meet with tons of companies every week, work hard for their portfolio companies, and are on planes flying around to the important confereneces and demo days. I can assure you they are working harder than I am.

But when it comes to winning deals, they have a distinct disadvantage. They can be working on a deal for a year or more, and then when the entrepreneur decides to raise funds, a more experienced VC such as myself can swoop in, spend a week or two building a relationship with an entrepreneur, and take the deal away from them. I've seen it happen. I've done it myself.

They make rookie mistakes. They let a reporter hang out with them for a week thinking they can trust them. They talk when they should be listening. They overpay for deals thinking that will win the deal for them. They use their phones in board meetings. They fight with entrepreneurs over meaningless things.

When I see these things I cringe. Because I've been there and done that. I spent the first ten years (maybe 15) of my time in the venture business as a young VC trying to make it in the game and not really knowing how. I've made all of these rookie mistakes and more. I feel for them, I often mentor them, and I really enjoy working with young VCs.

When a young person asked me about getting in the venture capital business, I advise them not to. I think VC is an experienced person's game. Startups are not so much. Startups are a great place to be in your 20s and 30s. VC is a great place to be in your 40s and 50s.

I look at Ben and his partner Marc and think "they did it right." They got into the venture capital business when they had all the experience one could ever want working with startups. They don't lose deals to more experienced VCs. They win deals over more experienced VCs.

But of course many young VCs made the decision to get in the game at an early age and are committed to making it work. They are going to have to take their lumps. Make the mistakes. Learn from them. Continue to work harder for less results to show for it. And lose deals they should win.

One of the things I did not do very well that many of these young VCs are doing much better is building relationships with more experienced VCs. As I said, I work with a bunch of them. Teaming up with a more experienced VC can help you win a deal, you can learn from them in the board room, and you can ask them for advice when you screw up.

Going back to where we started this post to end it, I like how Jay-Z and Memphis Bleek partner up in Coming Of Age. That's the way to do it.

[JZ] Hahahh I like your style
[MB] Nah, I like YO’ style
[JZ] Let’s drive around awhile

#VC & Technology

Comments (Archived):

  1. Dave Pinsen

    Not a rap aficionado, but old enough to think a good title for this might have been Young VC. 

    1. fredwilson

      i was going to use that but got caught up in the song

  2. Thomas

    But maybe this is good for the entrepreneurs, they can contact a small VC for the first round, and as an early stage company, and when everything works fine, they can contact a bigger VC to really grow up. Is that correct?

    1. fredwilson

      Young VC might be working for a big VC firmBut your point is a good one. Seed and real early stage is a good place to be when you are young

  3. scottythebody

    Great post. 

  4. Yalim K. Gerger

    This is one of the best posts in this blog. Thank you.

  5. John Revay

    Sounds like the VC biz is a rite of passage, my sense is that  might be a outlier.They are raising some big funds – hopefully their returns can keep up.

  6. Tom Labus

    You were smokin’ this morning!!!!!But as a young guy you need to take a few poundings before you really start to listen and pay attention.

    1. fredwilson

      yup. i certainly took my share.

  7. Anne Libby

    “They use their phones in board meetings.”I don’t buy that people raised in the digital age have “evolved” to be able to pay attention to multiple things at once. There must be a reader out there who’s a neuroscientist: am I wrong?One of the most valuable things any of us can offer to those we mentor is some coaching on how to be fully present in a room — whether we’re meeting with one person, in a meeting, or at a conference with hundreds of people. And the number of reasons that this is important.(For one thing, I hear from/about plenty of people about how their kids have felt slighted when they’ve used mobile devices at the dinner table, on the sidelines at soccer, etc.)

    1. Tom Labus

      Great point about paying full attention to your kids.

      1. Anne Libby

        For many of us, the way we are at work is the way we are at home…

    2. fredwilson

      i had to learn this Anne. i thought i could multitask too.

      1. Anne Libby

        Me too. Now let’s teach it.

      2. Koslow

        My father teaches me to be fully present during conversation, especially conversations on the phone. Yet, I see him sending emails, and reading documents all the time while on the phone. I especially notice it when he does it to me.That kind of teaching doesn’t work. I get that urge to multitask too, but which is more important… be your word.

    3. obscurelyfamous

      Yeah. Whether or not people can effectively multitask, it sends a very strong message when you’re giving something/someone a fully undivided attention.It shows a level of care and commitment unlike any other.

      1. Anne Libby

        Daniel, I agree 1000%.

  8. William Mougayar

    RE: “young VCs … building relationships with more experienced VCs.”Adult supervision works well in all settings! 

  9. William Mougayar

    This is a very insightful blog post. As an “experienced” (read: Older) entrepreneur, every bit of it rang so true, and I have seen these things in front of my very eyes. The best thing a less experienced VC can do is to get into deals with more experienced VCs. The thing about Experience is there comes a point when you’ve seen every kind of situation out there, and you’ve done the right and wrong thing about it, so you can quickly do the right thing and the best thing.Experience takes a lifetime…in wine, food, VC and business, in general. Nothing can replace it. And you cannot wing it. And only more experienced people can detect less experienced ones.

    1. JLM

      What is required is a bit of wisdom which masquerades as “good judgment”.  Good judgment commands a fairly high tuition.Good judgment the product of experience.Experience the product of bad judgment.You have to get in the game to exercise judgment.  The tuition has to be paid.

      1. William Mougayar

        Spoken from a truly great person JLM,- 100% right on. The notches on your belt or the stars on your shoulders count for something, don’t they.

      2. fredwilson

        JLM – you have made this point many times here using some of the same language and i always find myself shaking my head in violent agreement. Well said

        1. William Mougayar

          I love the Tuition analogy. Life tuition,- you have to pay it. They don’t give scholarships for it.

      3. Roger Toennis

        …and the tuition paid always includes pain to the untested ego.My favorite passage from John Donne’s famous Meditations XVII speaks to this. XVII is the one with his well known, and Hemingway-honored “For whom the bell tolls…” observation. Elsewhere in that meditation are the words that speak to your’s and Fred’s observations on experience.”..Affliction is a treasure, and scarce any man hath enough of it. No man hath affliction enough that is not matured and ripened by it.”           – John Donne (Meditations XVII,1624)

        1. Tom Labus

          That was a great quote, thanks.

      4. another cultural landslide

        There is a lot to be said for falling on your ass a few hundred times: you build up the appropriate calluses on your butt – and sometimes, you learn how NOT to fall on your ass.Great post, and great replies, y’all.

        1. LE

          Check this out. I have a pullup bar at work. I actually fell on my (bony) ass from full pull up height with legs fully extended on the last pull up of a set. Fell straight down (5 – 6 feet) and hit the floor on my ass. No damage whatsoever.  At that point I replaced the pull up bar. I knew it needed replacement but ignored my mantra “don’t be lazy”. 

          1. JLM

            On the other hand, perhaps there is also something to be said for falling on your ass only once?Call to action?

          2. LE

            I was burned as a kid.When I was maybe 5 there was a hot water humidifier in my sisters room. I jumped over the electric cord which was stretched to the outlet. My sister told me to do it again to show my other sister. I did and my foot caught the wire and I was scalded and spent time in the hospital. It had a tremendous effect on me. I don’t succumb to peer pressure or crowd pressure or family pressure.



    2. fredwilson

      You cannot wing itSo true

    3. Robert Thuston

      Well said.  Knowing all the different iterations and outcomes of a situation because you’ve seen them all is invaluable.

    4. sigmaalgebra

      Experience is the best teacher, but a fool will learn from no other. – Benjamin Franklin.

      1. William Mougayar

        Good one. Thx

  10. William Mougayar

    From the movie Colors (1988):Bob Hodges: [to his new partner] There’s two bulls standing on top of a mountain. The younger one says to the older one: “Hey pop, let’s say we run down there and fuck one of them cows”. The older one says: “No son. Lets walk down and fuck ’em all”.…

    1. JLM

      Haha, I was thinking of the same anecdote.  Very funny.

      1. William Mougayar

        Lol. Great minds think alike.

    2. JLM

      Best movie Sean Penn ever did and anything w/ Rob’t Duvall is going to be great.

      1. William Mougayar

        Another great quote of Duvall when he says “I love the smell of nepalm in the morning” in Apocalypse Now.

        1. JLM

          I have actually smelled napalm in the morning.

          1. William Mougayar

            That’s what I thought, which is why I mentioned it.

    3. LE

      From “Dallas” – “If Jock were here he’d know exactly what to do…”.Couldn’t find that clip but here is “power is something you take”:…(Bobby Ewing looks a little like Rick Santorum…)

      1. JLM

        I love that gravelly voice of Jock Ewing (Jim Davis).

  11. Carl J. Mistlebauer

    Old Japanese Proverb: “To teach is to learn.”So many times we want to believe that “mentoring” is a one way street and it is not.Having younger people, having interns, makes me question some of my “wisdom” and it should be seen as an opportunity to rethink…..

    1. fredwilson

      teaching is something i love to do because it makes me better



          1. FAKE GRIMLOCK


          2. LE

            Had 60 Minutes lined up. Now chance for exclusive blown. Told same thing to Trayvon’s parents.

          3. FAKE GRIMLOCK


          4. LE

            As a role model you shouldn’t kid like that. Right now some young person is reading what you are saying and might not return Don Hewitt’s phone call.  

          5. Rick Mason

            That would be a pretty amazing trick getting a phone call from Don Hewitt.

          6. LE

            Wow. I’m getting sloppy. And I had plenty of sleep last night also. Hmm.

          7. FAKE GRIMLOCK


          8. LE

            Always be a need for newspapers. People need to train puppies and wrap fish.

          9. ShanaC

            I read the newspaper -online.I’m well under 50.And I occassionally watch the 11 o’clock news in the form of the Daily Show/Colbert ReportIn one of the rare moments I watch tv that is….

          10. Tyler Hayes

            I’m 26 and still watch 60 Minutes. Some of us were just talking about it and FRONTLINE in the office last week actually too.

          11. ShanaC

            Frontline is the best – plus they have old episodes on the web from forever ago

          12. LE

            Also, would have suggested story go on April 1st not the day before. 

          13. FAKE GRIMLOCK


          14. LE

            “ALSO, GRIMLOCK NOT JOKE.”Adds to the mystery. 

          15. ShanaC

            Then what are you, really?

  12. Robert Thuston

    Right on.  What about the importance of defining boundaries around what a young VC invest in?  We have an architecture firm in birmingham run by an architect in his 20s that never followed the rules by working for a big firm first.  They’ve become the go-to architecture firm for creative spaces the historic district of the city.  If you are a small business, restaurant, or ad agency looking for a handcrafted space in that area, (they have a wood workshop and build out the spaces themselves) they are the firm.  It’s amazing to see how they’ve “branded” themselves in the last 2 years by having a laser-like focus on their style and the work they accept.

    1. fredwilson

      be really good at one thing when you start out. great advice.

  13. Robert Thuston

    If they are using their phones in board meetings, they get what they deserve : )

    1. fredwilson


    2. David Semeria

      Also talking when they should be listening, as Fred said.Recently I couldn’t get a word in edge ways with some chap I have known for quite some time and who became a VC exactly 3 months ago. He kept asking the same question and I kept giving the same (rather technical) answer, which he clearly didn’t understand.In the end I told him that if he didn’t stop asking the same question I would take my shoe off and throw it at him.I was only half-joking.

  14. JLM

    While Fred writes about the VC business, the message and wisdom is applicable to the game of life writ large.  How do you learn your craft?You go to school and you pay your dues.  You put in the time.  You take your risks.  You lick your wounds.  You learn and come back more knowledgeable and stronger the next time around.  But you learn.There is no more telling transformation than being a second lieutenant in the Army and getting your first platoon.  The first time you stand in front of them — 40 soldiers — you know that everyone there has more time in the Army than you, none of them are inclined to like you and all of them know that you know next to nothing.Sure you may have a Ranger tab and jump wings, but that really has nothing to do w/ the business of soldiering.  The soldiers like their officers to be Rangers and paratroopers.  Because the big secret is they ultimately want to work for someone who learns their craft and will not get them killed because of incompetence or vainglorious notions of heroism.In six months, you will either have learned how to lead or you will have an irreparable crack in your soul.  Most guys learn how to run a platoon but there are some who never get it.The secret: you have to ask for help and have the humility to accept the responsibility while not pretending you have earned it — yet.I remember standing on the banks of the Rhine in pretty high flow knowing that tom’w we would be building a floating bridge across that monster.  For one instant I felt the panic rising in my throat.  I could taste it.  I could feel the flop sweat, the projectile sweat unleashed.And then I took a deep breath and asked the non-coms who were standing with me how many had ever bridged the Rhine before.  All of them had.  I took a deep breath and exhaled and said:  “OK, teach me what I need to know.”  They all laughed.  Maybe even a bit too much laughter really.That night we made a big sand table and for about 6 hours I went to school on how to bridge th Rhine.The next morning I gave the orders to the same NCOs and they nodded their heads and asked questions in front of the troops like I had known how to do this.  A complete charade.We did it and truth be known, we did it pretty damn well.  Easily the best in that battalion.The Bn Sgt Major came down to see the exercise and collared my Plt Sgt and said — your Lt seems to know what he’s doing.  My Sgt laughed and said:  “My Lt is sharp as rat shit, Sgt Major, pointed at both ends.”  <<< This is the kind of nonsensical thing they really used to say in the Army.  It is their language.I had a great time in that unit.  I paid my dues, I learned a bit about soldiering.  More importantly, I humbly learned a lot about myself.At the sand table, I earned their trust.  They knew I was willing to admit what I did not know.  Later I earned their respect because I had given their superior knowledge my respect.I was very lucky to have had that experience.  It has given me the courage in life to never ever be afraid to learn while admitting I don’t know something.  To respect knowledge.After 3 months down on the Rhine, we had our test and that company set the record for crossing the Rhine the fastest in the history of such tests.  I bought beer for everyone and it tasted damn good.I salute all the NCOs who helped me learn my craft, such as it was.  They molded me as surely as if I were a wet lump of clay.  I ought to grant them options.

    1. CliffElam

      How can 50 people not have “liked” that reply?-XC

      1. fredwilson

        no liking on the new disqus. upvote baby!

        1. Brandon Burns

          i’m still seeing “like” as an option, and my disqus still looks the the new disqus only viewable to certain users? 

          1. fredwilson

            yes, they are in early beta and only showing it to a small cohort

          2. FAKE GRIMLOCK

            ONLY GET IF SIGN UP.

        2. ShanaC

          but now they have downvotes 🙁

    2. Tom Labus

      You should do a book!

    3. William Mougayar

      This is a golden truth: “The secret: you have to ask for help and have the humility to accept the responsibility while not pretending you have earned it — yet.” And you have to keep doing that over and over again. I love it when I come from behind as the underdog and pass those that were seemingly ahead of me. Being dogmatic pays off.

    4. William Mougayar

      JLM- You’ve got to open-up a Tumblr account (takes 3 mins), then Connect it to Engagio, and in 1 click you can selectively push these comments from Engagio, so you’ll have a permanent place for all your pearls of wisdom. You don’t have to enable comments on your Tumblr side, in case you don’t want to manage multiple conversations, but at least those following you on Tumblr can re-blog them, share them, etc… just saying 

      1. Matt A. Myers

        I think these might become bedtime stories for my future children..

    5. fredwilson

      admitting it when you don’t know what you are doing is key. great comment JLM

      1. Tereza

        Gotta tell you. I’m pretty open to admitting what I don’t know.I’m not sure it’s always a good thing.Things that are very hard for what seem to be the majority come very easy to me. And then other things which seem to come easily to “everyone” — I wonder why the hell I’m so far off.It’s tricky to discern how much is age, how much is gender, and how much is just specific to one’s own self and maybe even your mood on that day.

        1. fredwilson

          one of the tough things about making the switch from big companies to startups is that big companies come stock full of mentors. i recall that you had a slew of them. in startups you have to go out and find them because they aren’t in your company.

          1. obscurelyfamous

            One thing about startups or smaller teams is that you typically bring in people who are going to punch a bit above their weight class. They’re hungry and they’re getting impatient in a slower moving organization.But once they take on that lead role at a startup, it has to be communicated/known that there isn’t a ton of mentorship in the company already. I’ve seen otherwise ambitious people who don’t thrive because they get lost in priorities.Searching for outside mentorship is critical. Even better if the company is able to provide this easily.

          2. JLM

            When a CEO catches his breath and catalogs all that needs to be done, it is often disconcerting that you need about 13 days in each week and 19 hours of work in each day.That has never changed since the beginning of time.Nonetheless, you have to simply do the best you can.Mentoring is all about the right minute, not the total minutes.  The “aha” moment.Mentoring is not a street light, it is lightning.  Infrequent but explosive.

          3. William Mougayar

            Yes,- and in a startup everybody has to continue stepping-up. The growth part makes it such that each job changes every 3 months or so. Startup = Dog years for everything.

          4. obscurelyfamous

            I love that. Startup growth is measured in dog years.

          5. Mark Essel

            Unofficial Disqus feedback, I’m having trouble clicking the HackerNews arrows on my phone. They’re a bit too small. And I click a lot of up arrows.Might be a good spot to apply the Apple button/control interface guideline,

          6. Tereza

            That’s true at a high level Fred but practice is a bit different….especially if you want to “win” at that game. I’ve drawn the conclusion that what in the large company we’d call “political” is what we on the open startup market call “entrepreneurial” but in fact they’re the same thing. These days, given how easy it is to identify and get in touch with people via social networks, it strikes me as barely different from being inside a large company. Because in both there’s a sense of “community”. At least in New York. I mean, the company I was with was the largest employer in NYC — I’d be curious to know how the #s compare to the NY tech scene but I think the tech scene is actually smaller. I could be wrong. Feels similar. In a large company, you’ll likely be assigned mentors, but they are highly unlikely to be the right match for you. And one mentor will not a career make. Look — your best mentor does not come to you, you have to find him/her and make it happen. Any/all successes I had on that front was because I pounded it and put out 5x the requests. The majority of my colleagues felt under-mentored and thought I was the golden child and attracted all the attention. I don’t think they had a clue how hard I was working to make those relationships take root. Exactly zero were handed to me on a platter. For example, for the bigwig global head of blobbety blah, I’d sit in a cube with a view of the door to the men’s room. When I needed him to review something — if I needed a quick approval, I’d “bump” into him on the way IN. Needed a longer conversation? That’s a serendipitous “bump” on the way OUT of the bathroom. Got a lot of good business done that way. You have to be creative.When junior staff would complain to me about not having good mentors, which was often, I’d give em a lump on the head and say “You idiot, why did you think anyone was responsible for this other than you?” I mean, WTF?

          7. fredwilson

            WTF indeed

          8. JLM

            Every job description should start w/ the phrase — “I am responsible for everything that happens or fails to happen…”Peer to peer mentoring is a lost art but you have to have enough critical mass to have a peer to peer pool to be able to make it work.This is why organizations like YPO and TAB are so effective.  Peer to peer discourse.

          9. Tereza

            This is where some kind of early struggle is really useful. Be it immigrant, dirt poor, dysfunctional household, whatever. Point is if you don’t get handed anything — you need to choose you want X and dammit get out of the way people I’m gonna do it. Some step up to the plate, some people don’t.But, on balance, struggle sure builds strong muscles!It also creates Flow.

          10. JLM

            @Tereza:disqus Below.We are driven most firmly by our insecurities.Give me poverty, deprivation, hunger, prejudice, inequality, unfairness — and a yoke.Strap that yoke on and pull anything to the finish line fueled by those perceived inadequacies.No revolution was ever started on a full belly.Nothing to lose and everything to gain.  Dangerous people.

          11. Carl J. Mistlebauer

            Tereza,Having started my career with ARAMCO, which is massive and so much more than an oil company, I understand your comment about “political” and “entrepreneurial” and it is a valid point.I do believe there is a fundamental difference because in large organizations you are in effect competing with or against others and as entrepreneurs you are basically competing against your own limitations.If you really want to see vicious “corporate” politics then come work for a small company; its pathetic to watch people trip each other, hide data from each other, go around and behind others for no reason! I mean their were no promotions or firings, there was nothing to “win” other than the fact that you would be in good graces with the owner….The things people will do…..

          12. William Mougayar

            Not only that, but in a big company one can slack off and nobody will notice for a while. In a startup, if you slack off, you’re out.Having done Big–>Small–>Big–>Small, I found that employee productivity is much higher in smaller companies. For one, the frequency of internal meetings in large companies is a killer.

          13. Paul Sanwald

            fred this is a great point, I wish someone had told me this when I was 22. I am going to pass this advice along for sure.

      2. matthughes

        “Know what you don’t know” is some of the best advice I’ve ever been given.

    6. daryn

      Wow, this was a great post already, and your comment just made it 10x better JLM. Thank you!

    7. LE

      I have tremendous respect for what you’ve done.Kids today aren’t raised the same way. They get medals for everything. They get complemented on everything they do. You can’t snap them into shape with any “bad” words.  You have to talk to them as a therapist would.Occasionally, is it so bad to tell a kid “get your shit together or you’ll be a loser”.

      1. JLM

        Kids are not allowed to be kids.  They are whirlwinds of activities and parents are chauffeurs and social secretaries.We give them a T ball view of the world.Everybody gets to keep swinging until they get a hit.Nobody is ever out.Score is never kept and there are no losers.Everybody is a winner.Then, we go out for ice cream.Warped.My daughter played basketball w/ the boys and held her own.  There was never a ball that ever went on the floor that she did not recover.  She was like a wolverine.We have to train our kids to win v lose because they want to win.  

        1. LE

          I’m curious about what is going to happen to all the young people that are working in startups (the ones with ping pong tables, free food, and “fun”) when those startups fail and they have to then get jobs at some insurance company, bank or traditional company. Added: Or they try to start a company that is not the apple of a VC’s eye and learn what can’t be done without a few million in non-recourse money. Where you don’t get even a year to break even let alone several years.

          1. JLM

            They are going to get haircuts, tuck their shirts in, press their pants, learn to respect Father Time and go regroup.The entrepreneurs will lick their wounds and emerge more seasoned and will try again.  They cannot quit.The less courageous and energetic will become handcuffed to the wheel and push for 30 years in quiet desperation and think — I coulda been a contender.Life and a shitty economy are mean taskmasters, heartless bitches really. The strong will prevail as they always have.

          2. Carl J. Mistlebauer

            The human spirit….A spirit that enjoys success humbly because it acknowledges that success is not always due to effort or skill of one; it acknowledges the contribution of those in the past, today’s coworkers, and tomorrow’s dreamers.A spirit that recognizes the dignity of those whom have failed but have picked themselves up and moved forward, with humbled spirit but head held high.It recognizes that no man is an island….Give me the individual who has failed and paid the price of their defeat and yet still moves forward, still dreams, and is bitter of no one…..THAT is a winner, that is the human spirit, and that is dignity….and maybe I admire the wrong traits in people.Winning and success are actually easy, its failure and humility that are hard….its getting back on your feet that is life’s ultimate lesson.

          3. Gaynord73

            Couldn’t agree with you more JLM, a natural Malthusian check for entrepreneurs

          4. Donna Brewington White

            It boils down to whether we look at adverse situations as opportunities (even if for learning and growth), obstacles to overcome or impenetrable walls.  And sometimes, we just need to pull back and wait it out until we have the resources we need, internal or external, to go back in.I wonder how much control we have over how we view things, or whether this is assigned to our nature. I sometimes wish I knew how to quit or to be content with the status quo.  Okay, not really, but it seems so much easier.But it is not enough to just keep going.  Even the insane do this.  You have to move forward changed somehow.

          5. Donna Brewington White

            Corporate environments provide an excellent sifting mechanism.You find out what you are made of …or not made of.  In my case, I found out long before my bosses did (they begged me to stay) — even though I did not yet know the word entrepreneur.  But I knew that to stay would have been death.

          6. Donna Brewington White

            Is that such a bad thing, to have a failed startup?Seems that failure is a prerequisite for prolonged success.  May as well get it over with while you are young. And, then, with regard to working at a “traditional” company for a few years — personally, my first job at a large financial institution is where I learned the discipline and structure that my upbringing did not provide. Maybe the entrepreneurial culture is an antidote to some of these failings in upbringing that you and @JLM:disqus are pointing out. Perhaps working for a startup should be considered extended education.  In a startup you learn real fast. Or you’re gone.   

          7. LE

            “Is that such a bad thing, to have a failed startup?”Not at all (as long as money isn’t an issue). But I am referring to not the founders but employees who that don’t understand the difference between a startup culture and a traditional culture that are in for a shock in the real world. Typical traditional company employee is much different than at a startup (age, family, motivation and how they spend their spare time).

        2. Donna Brewington White

          “We give them a T ball view of the world.”Wow.

        3. Jim Ritchie

          This topic is hotly discussed amongst my friends and colleagues here in SF in the 40’s age bracket with kids. We grew up in a time where we, the kids, picked the game, made the rules, and selected the teams. There was always a clear winner, and loser, but in the end it was always a great learning experience. I’ll never forget when I was probably 10 years old complaining to my Dad about how “it was just not fair” that I could not go on a camping trip because I was sick. My Dad just said get over it, life is not fair, and best to learn it now. Those words have helped me many times when dealing with potential failures. Also, a buddy of mine, Po Bronson, wrote a good book on the subject called NutureShock, worth checking out.

          1. obscurelyfamous

            Exactly. I prefer “Life is only as fair as you make it.” It encourages every generation to understand that social standards are dependent on their actions, and their actions only.

          2. LE

            “My Dad just said get over it, life is not fair, and best to learn it now.”Yeah I had that “get over it” many times said in the harshest tone. I also remember making a comment in college to a Jewish advisor something about school on a Jewish holiday. He said something like “It’s a Christian world you might as well get used to it”. 



      1. FlavioGomes

        Now that is good!

    9. ShanaC

      Anything you wish you would change from that period of time?

      1. JLM

        Sure, you always do but not really. I have been incredibly lucky and have been so blessed by luck and happenstance.

    10. JLM

      The young Lt himself.  Just parachuted into a rice paddy and landed standing up to avoid the “night soil”. Just learning the business of soldiering.

      1. Matt A. Myers

        Thanks for sharing that

      2. Brian

        Thank you for your service to our country.

    11. kidmercury

      63 likes at hte time of this writing… this the most liked comment in fredland history? 

      1. fredwilson

        not sure. disqus analytics is acting weird for me right now. but it is certainly the most liked in the past 30 days

    12. Mark Essel

      I’ve read a variant of this experience of yours before. Each time you share it we get a slightly richer view, with a different focus on lessons learned. 70 up votes (and rising). That’s a solid gauge of this community’s appreciation.

    13. EntrepreneursAnonymous

      Wish they’d taught us that at (leading business school name omitted.) Thank you for sharing.

  15. Brad

    Tell some of those young VC’s to give me a call…..Experience will always win out. My seven year old loves the show shark tank. The smart entrepreneurs don’t just chase the money, they chase the strategic partnerships on the show. Mark Cuban gets the most deals because he rarely just pitches money he pitches connections and how he is going to help the company grow.I assume this is how you pitch yourself and the connections that you may have to help the company explode.

    1. fredwilson

      i don’t pitch value add. i pitch empathy understanding and a human connection to the entrepreneur.

      1. Brandon Burns

        i’m assuming that your success comes from your empathy being legitimate. generally when you have a specific area of interest that you’ve deep-dived into, as USV seems to do, its easy to empathize with others who are also deeply involved in the same thing. when you’re all over the place, or are blinded by superficials, it’s hard to dig deeper with people. it’s like the guy who talked to every girl in the bar; he either goes home empty handed, or with someone less-than-desirable.  but then again, some of those guys who make the rounds are really skilled at the “but i’m really into YOU” pitch, despite being a scum bag. let’s hope thats not you, fred. :o)

        1. fredwilson

          i’ve never been good at the bar scene

      2. JLM

        We cannot help but to like the most those who like us the most.This is both the source of true love and treachery.The opposite of love is not hate, it is indifference.

        1. Brandon Burns

          true. and then other times we often don’t like the ones who like us the most. its the wanting what we can’t have syndrome. or the dating in nyc disorder, which ever you’d like to call it. 

      3. Guest

        Fantastic post Fred.  Empathy always wins over arrogance in the long term.  

        1. kidmercury

          really hope you add men’s clothing to your web site at some point… need clothes too! 🙂

          1. Guest

            It will come Kid.  Hold tight.  🙂  I worked as a buyer in menswear for Ralph Lauren so I understand your frustration of not being a first priority.    

      4. matthughes


  16. CliffElam

    It’s not just in the VC game. I can assure you that many of the people on my team are smarter than me and work harder than me. I’ve been working full time since I was 17 – over 30 years – and I make a lot of mistakes, but they’re generally at the margins.I view my job as a coaching job more than anything now.-XCPS – I do notice that the ability of new hires to accept coaching and guidance is very age dependent. New college grads seem much less coachable than they did 15+ years ago.

  17. JLM

    This is how I want to master my craft and life.  Don’t dare watch this video unless you have the capacity to be impressed by life.…Think of this like Fred pouncing on a good deal.

    1. Tom Labus

      Talk about take out.Their eyesight 8x a human’s. 

    2. Brandon Burns

      breathtaking video. nature tv is one of my indulgences. you’d probably like human planet:…i want to fish like the guy in that link. big risk, big reward. no safety net, other than confidence, patience and focus. exciting! 

      1. JLM

        I want a pair of those magic flip flops!I suspect there are no leftovers at that fisherman’s table.

      2. sigmaalgebra

        He’s got no obesity problem!  Likely no dental problems.  Darned clever guy — ‘single founder’, good planner, thoughtful, deliberate, careful, skilled, effective, successful.  Likely a better view of who we were and still really are than what we see in our daily lives.Those little pieces of vertical rope — NICE geometry!

    3. sigmaalgebra

      Yup, amazing.For a full screen version, just slightly trim the right end of the URL and get and go to:…Super good work with a very long focal length zoom lens and a long range microphone. Where did they get such amazing toys! Yes, the difference between men and boys is the price of their toys!GREAT place to build a rustic house and enjoy four seasons a year! Good place to own a four wheel drive light truck with aggressive mud/snow tires!There needed to be on the shore a pot of fish stock with shallots, thyme, bay leaf, white wine from Macon, blond roux, cream, egg yolks, S&P, lemon juice, and soft butter (sauce Parisienne), a loaf of French bread, an iced bottle of Montrachet, some Orrefors glasses, some semi-soft cheese, a bottle of Chambertin, a girl I remember from Memphis, and, say, a chilled Sacher Torte with either some coffee or just an iced 2 liter bottle of Coke! For background music, just listen to the birds!It’s fun to look at the sky and see big things, and more fun to see what we know about the history from the big bang to the creation of the earth. But all that amazing history led to that video clip, is relatively simple compared with that clip, and now looks like just simple infrastructure for that clip.Simple? Yes: We can do the physics in good detail of a quasar or supernova 10 billion light years away but can’t do the physics or the computing of protein folding in one cell here on earth.So, have to guess that the ‘purpose’ was more the video clip than the big things we see in the sky.Net, by far the most amazing and complicated things and the best indication of a ‘purpose’ we know about are right here on earth as in that video clip.If we assume that the universe is ‘uniform’ in various respects, then we can’t be alone, but that is one heck of an assumption that might in some important respects be false. We may yet be not just the most amazing things we know about in the universe but really the unique center and purpose of it.That all the life we know about, the millions of species including ourselves, is just from four amino acids in combinations in DNA looks suspiciously deliberate and amazing beyond belief. Such things appear not only more subtle than we know but more subtle than we can know. Then that’s a question: How much of this can we know?

    4. William Mougayar

      Eagles are smart, strong and have great eyesight! What a video!

  18. Dustin

    I’d imagine younger VC’s beget fewer higher returns in exchange for taking on increased risk while veterans volatility is largely marginalized and based on proven businesses and business models.

    1. fredwilson

      not sure about that. as i get more experience i want to take on more risk, not less

      1. Dustin

        The bands you listen are a leading indicator of why you’re likely an exception to the rule.

      2. William Mougayar

        Because you’re better at calculating that risk?

      3. LE

        Can the risk be quantified? Also if you have more experience is it really more risk relatively? A black slope is risky for a blue or green skier but not an experienced black skier.I hope you do it for business reasons and not to get the same buzz (which doesn’t come from doing the same old deals).…

        1. JLM

          Risk is sometimes a matter to be measured and minimized by experience, talent and judgment; and, having dealt with it before a knowledge as to what the real quantifiable downside is going to be.If you have jumped out of an airplane, then the second time is simply not as risky as the first time.  If you have done it 100 times, less risker still.The ability to be calm under fire is not just a skill, it is a way to manage risk.If you have it, then things can be pretty dicey and you have a higher probability of prevailing.

      4. Donna Brewington White

        That’s pleasantly surprising, as well as refreshing, to hear you say this as a “more experienced” VC.  But maybe not as surprising considering the source.

      5. Brad Lindenberg

        Buffett always says the difference between investing and baseball is that investing isn’t a 3 strike game. With investing you can hold the bat for as long as you like and let opportunities through before you take a swing. I think the more experience you have as an investor, the easier it becomes to see the patterns that make for a sound deal, and therefore you become more confident which leads to having the conviction to task bigger risks and swing hard when the right opportunity present themselves…

        1. fredwilson


  19. Morgan Warstler

    One of your best articles. Right up there with going to market on backs of brands or directly to users.

  20. Austin Clements

    Fred, as a young person aspiring to work in VC I recognize the challenges that I’ll face regardless of the work I’ve done, knowledge I have. Experience and reputation are paramount. There are several different avenues to get that experience and quite honestly, you’ve probably taken the most difficult one. I can see why you advise against getting directly into the business.Excellent music selection this morning. That’s one of my favoriate Jay-Z songs as it does describe the mentor/mentee relationship quite well. Several years ago mentor of mine had me sit listen to that song on repeat until I knew all the words. Couple hours later I finally got it. Couple years later I really GOT it.After the “Let’s drive around awhile” part Jay-Z offers Bleek a little money to get him started. Bleek refuses and says he’ll ride for free because he’s in it for the long term. That’s how I’ve come to look at it as a long term career path. Today, more than anything, I simply enjoy working with entrepreneurs to develop new business ideas. This can come in many forms. So no telling what the future holds but I tend to believe if you’re patient and driven by a vision things will fall into place at the right time.

    1. fredwilson

      patience is key in the venture business

  21. andrewparker

    Surprised there’s no Young VCs in this thread, so I’ll be foolish enough to jump in first.Fred’s spot on.  I’ve made all these mistakes, and I have not made them enough times to learn otherwise, so they’ll keep on coming I’m sure. I’m young, and i’m self-aware that I’m young, but that doesn’t make the mistakes any better. I particularly liked the point in Fred’s post about access to the best deal flow. It’s painful to work on a deal for a long time (likely too long… by definition), build a relationship with an entrepreneur and then watch a more experienced VC swoop in and scoop it up from in front of you in a week’s span.  As a young VC the only recourse is to fish in other ponds or team up with the competing VC.  It’s very difficult to convince the next Mark Zuckerberg that you (the young VC) are a better fit to finance his company than Mike Moritz.  Since you can’t win head-on, you have to play different.Youth is nothing other than a (reasonably good) proxy for experience. That’s why JLM’s comment on this post is so good. When in a position of leadership at a young age, he supplemented his experience gap with a willingness to ask for help.  There are many mistakes young VCs make that you can avoid by asking for help.  Some mistakes are unavoidable because “you don’t know what you don’t know.” And, youth is a proxy that you can judge from first appearances, because young people look young, so it’s a very convenient proxy that will often allow your first impression of someone to be an accurate one. Because youth is just a proxy for experience, I’ve seen a few 40-50 year old first-year VCs make similar mistakes to what Fred describes.  They often recover better because they have more experience recovering from mistakes in general, but many of the same pot holes exist.Youth in VC has one advantage when it comes to experience. Most of the young VCs I know grew up along side the internet and thus had a front-row seat to what’s a compelling internet product (and what isn’t). So if you’re a young VC investing in internet startups, it’s possible to be more experienced in web user experience than your 50 year-old plus VC counterpart. But, yet again, this is just a proxy. There are plenty of older VCs that are far more net-native than your average 28 year old banker-turned-VC-fresh-MBA (hell, some of the older ones INVENTED this stuff we take for granted… thanks Marc). 

    1. fredwilson

      i think you are on your second five year stint by now Andrewand while you say you’ve made all of those mistakes, i am not sure i’ve seen you do any of themyour self awareness is your greatest asset

      1. andrewparker

        Hah! I know you’re lying cause I’ve made plenty you cleaned up! :)Thanks for all your help over the years.

    2. JLM

      We are all a product of our age.  The young VC who has never known a world without the Internet may very well have experience in life that is not shared by the older guy.Don’t take social media advice from anyone over the age of 27?Well played!

      1. William Mougayar

        I have a 21-year old advising me on social media while he’s still in college. He’s great.When I was 35, I would get paid to advise 50-year old CIOs & CEOs about the Internet.

      2. ShanaC

        Meh – I’ve heard great advice from people of many ages.

      3. Stuart Campbell

        IMHO ageism is a problem. Discounting someone based on age is like discounting someone based on the color of their eyes. It makes no sense! Excellent and terrible advice can be garnered from people of any age.

        1. obscurelyfamous

          Agree, though I think ageism is a (sometimes naive) shortcut for determining who can relate to what generation of thought.

          1. JLM

            There is chronological age.There is age determined by level of energy, fitness and intellectual vigor.There is age determined by curiosity and willingness to experiment.There is self perceived age.There is age defined by cultural awareness.Of them all, chronological age is the least important.

          2. obscurelyfamous

            Definitely agree.

          3. William Mougayar

            Indeed. What counts in not the years of experience, but it’s the Experience in those years.Abraham Lincoln said it best: “And in the end, it’s not the years in your life that count. It’s the life in your years.”

    3. obscurelyfamous

      I love that point: play it differently. Dealing with a younger (or less experienced) VC can also mean that this VC has less baggage that could influence over/under-reacting. The caveat of course is potentially a bigger chip on the shoulder.

      1. Ric Fulop

        Fred, this is my first time commenting on your blog. I’m really loving this post and the thread! As you’ve personally witnessed, I have quite a bit to learn :)I see the pattern all around me of my more experienced colleagues doing just as much in a lot fewer hours but I wonder if that that pattern is the reason why some VCs suddenly loose touch with the next generation of entrepreneurs a decade later. I agree that 40s and 50s are the prime investing decades. I think after a big string of hits it suddenly becomes very hard for folks in their 60s to keep up that track record. I guess what I’m trying to say is that VCs who work very hard at one point in their life enables a series of relationships and deal flow and at some point when folks are at a different pace and their networks have aged they suddenly find themselves disconnected from the new interesting stuff. I don’t want to name names but many of the VCs that I dealt with in the mid 90s when I was an entrepreneur and they were in their 50s have now found themselves out of orbit. What do you think? Clearly there are amazing people like @ronconway who this rule doesn’t apply to!Andrew, you are spot on about 40 yr old freshman VCs making similar mistakes as young VCs. I’m a prime example 🙂

        1. ShanaC

          @andrew parker (hmm ats are not working) and You too Ric – what do you think has been the biggest shaping momement has been among the mistakes you’ve made?

    4. Donna Brewington White

      I appreciate hearing this from your vantage point, Andrew.  Hope things are going well for you — I feel like I am one of those watching your emergence as a VC from a distance.I know that younger VCs can’t afford any more risk (and possibly less) than more experienced VCs but I have often wondered if a younger VC might be more open-minded and therefore recognize opportunities that an older VC might miss.  It didn’t take me long to realize that VC is pretty well entrenched with fixed thinking…and obviously not all that entrenched thinking is bad.  It just makes me wonder if this could be an opportunity.

  22. Irving Fain

    Great post which applies to entrepreneurs as well as VC’s. Like anything in life, failure and mistakes are the quickest path to experience and wisdom.On another note, wish it was only the young VC’s that used phones in meetings….

  23. Andy Rosenberg

    Another song you could source for this post – Kanye’s “Big Brother” off of his Graduation LP:”Only thing I wanna know is why I get looked over.I guess I’ll understand when I get more older.Big Brother saw me at the bottom of the totem.Now I’m on the top and everybody on the scrotum.”Perhaps a little graphic, but meaningful!…Love the post though and agree – 20’s and 30’s = startup life for me.

  24. LE

    One advantage of growing up when I did (which is the same period Fred did) is that there weren’t many examples of young people really doing well early on. You knew that if you wanted to be a Doctor, Lawyer or University professor that was going to take time. One of the reasons I started a business  (as you’ve pointed out in suggesting young people do startups not VC) was because I thought I would not be subject to any predetermined internship period before I could be made “partner” etc. (Not that I wanted to do that though truth be told. I always wanted to run my own business and had done so).So I did and it worked out and I made money much quicker than in any “profession”. Because there was nobody holding me back or predetermined time line. What I’m seeing today is different though. It may be because of the ubiquity of successful young people as a result of information available on the Internet, or, it may be for some other reason. But there is no question that young people today, at least from my perspective, don’t want to put their time in. They want to be overnight successes. They have entitlement and expectations. While some of them will be overnight successes I feel bad (mental health wise) for the 95% that won’t pull it off. They will be miserable because of their expectations of success.



    1. Joe

      I think Michael Lewis in Liar’s Poker observed that in the banking business you were nothing (and new nothing) until you had blown a couple of customer up with bad trades.  Sad but true.  I think in the startup world unless you are extremely lucky you really are nothing until you’ve blown up a couple VC’s investments.  In the startup world, it’s probably actually expected by all parties.  That’s one way to get maximum value from the VC funded/startup world.PS – I can no longer post under my Disqus login using Chrome and I think it has something to do with my cookie settings, but note to Disqus I am not willing to make the changes you suggest on your help page.  You should figure out something soon that’s easier on the user or you are going to use a lot of users like me.  

      1. obscurelyfamous

        Might be because of Chrome blocking 3rd party cookies? That can be a problem.Unfortunately this is a setting that prevents us from recognizing you on these pages.

      2. ShanaC

        So basically the takeaway of this post should be “you’re going to blow up stuff – fail miserably because it will make you smarter?”

        1. Joe

          More like if you haven’t founded or worked at a startup that’s blown up your investors you haven’t tried hard enough or had a big enough idea – or you’ve been extremely lucky.  Once you have then you are better equipped the next time to succeed.Contrast this to a “lifestyle” business where you are spending your own money and you by definition have nobody else to blow up except yourself.  So you are more likely to take less risk and have a lower level of success (because it’s your own money and you will find something more achievable and/or immediate, but probably not as world changing).

  26. LE

    They can be working on a deal for a year or more, and then when the entrepreneur decides to raise funds, a more experienced VC such as myself can swoop in, spend a week or two building a relationship with an entrepreneur, and take the deal away from them. I’ve seen it happen. I’ve done it myself.If the less experienced VC is smart and motivated, once that happened to them, they would take the time to analyze what happened and prophylactically inoculate their potential target against the possibility of you or anyone else swooping in and doing that again to them. While the lure of being represented by the “big agent” can appear insurmountable, no question there are sharp upstart agents everyday who manage to get their first deal with new talent that leads to further success. Part of selling is anticipating the spiel that the other salesman will be giving and putting doubt about them into the targets head. 

  27. LE

    They make rookie mistakes. They let a reporter hang out with them for a week thinking they can trust them. They talk when they should be listening. They overpay for deals thinking that will win the deal for them. They use their phones in board meetings. They fight with entrepreneurs over meaningless things.I love the honesty in this paragraph.It’s important for people to know what they don’t know. I was in a call with a young entrepreneur (trying to buy an expensive domain). I made up some bullshit spiel (I rep the seller in this case) and the entrepreneur (being all of maybe 20?) didn’t know enough to even understand that what I was saying made no sense at all and to question it. One rookie mistake he made was in trying to tell me that my client wouldn’t be able to sell the name to anyone else. That screams and says “I’ve backed you into a corner”. People know what their position is. Telling them you do has never been a strategy that I’ve used. That said everyone has their particular style and develops it over time knowing the nuance and “seat of the pants” of what works and doesn’t. It’s hard to transfer this to someone else in words because it can change on a dime depending on the subtlest amounts of information (vocal inflection or facial or hand movements). So you can’t read about it. You have to experience it.

  28. Ss

    Is there any empirical evidence with respect to returns and deal valuations for more experienced versus those with less?

    1. fredwilson

      I havent seen it. I would like to see it.

  29. sigmaalgebra

    Since the Navy had my father go to Memphis, I grew up there.I can like the BBQ (may have eaten literally 2000 pounds of it and can do an okay job cooking it myself just indoors), can admire FedEx, definitely remember some of the girls (more accurately can’t forget them), continue to respect the excellent math department that was at Rhodes College when I was there, but otherwise have a tough time liking the place.Yes, for the Memphis music, I was awash in it. But one night on the radio I heard Beethoven’s Seventh Symphony, became instantly hooked on classical music, totally dropped all popular music for life, liked classical enough actually to make some progress with violin, still like classical, and want to turn a computer into a tool for both composition and performance.There’s no kidding the BBQ (chopped picnic pork shoulder) is good. It should be because of some world-class fundamentals — sweet, sour, pepper, smoke, browning, pork fat, and gelatin. And pork cooks to super, moist tenderness while beef, veal, poultry, venison, and fish would tend to go hard and dry.So from Memphis I took away some math, music, memories of pretty girls, and BBQ but not the promised FedEx stock!Yup, if I’d been older, I would have cut a better “deal” for the stock! Maybe yet I’ll beat Fred Smith at the bank! He needed airplanes at $2 million a pop, increasing to $50+ million, and I need mostly just some computers I can plug together for about $1000 a pop! One of the things I did for him was write software that scheduled his fleet, that is, simulated part of his business. The software to simulate my business is my business and what I’m writing. Otherwise the main difference is the math I started with at Rhodes.Some of the French food I mentioned yesterday is actually better than the BBQ, and some of the French wine I mentioned is much better than the beer I used to wash down the BBQ. The math remains rock solid. The classical music hasn’t changed at all. But for the girls, naw, nothing as good!

  30. Richard

    According to the UNH center for research, in Q1 2011 three were roughly 2600 seed stage investments in software/internet businesses. Assuming all early stage investments come from this pool, can you give us a feel for how many USV might look at? meet the investment theme of  USV ? and of those how many might make the short list for an investment?  Are you saying that the competitive advantage of USV is that it is not necessary to vet the 2600 because others greener VCs will do so? 

  31. Mark MacLeod

    Great post Fred. I’m sure a number of young VCs read this and knew it to be the plain truth. I’m in my 2nd year as a VC now. But I spent the previous 11 years as CFO for one VC backed startup after another. Had success and failure multiple times. And still every day is a school day now that I’m on the other side. And I’m pretty sure I’m in elementary VC school. I.e, I have got a long way to go.I am fortunate enough to be playing in a smaller pond. Most of our deals are in Canada. But VC is truly an apprenticeship business. Nothing can make up for time and experience. You just need to go through it.

  32. willsoncuaca

    Hi Fred, I’m in my early 30s and have less than five years in the VC business.Coming from the other part of the world (Indonesia) there so much I would love to share and learn from you.Can we get in touch?

  33. starstudent

    Great, great post. Thanks Fred.  The rookie mistakes and disadvantages you mentioned are all true. I live those disadvantages on a daily basis as a person in that category (mid 30’s with less than 5 yrs in tenure). It’s important to recognize them early on when working on any potential deal. Equally important, I believe, is to maximize the distinct advantages that young VCs possess. As someone put it, you want to work toward your strength to be extraordinary instead of trying to fix shortcomings. With increasingly younger crowd start a company, I find young VCs relate better with those 20 something entrepreneurs. They are also more keen on experiencing the latest gadgets, apps, and services than the oldest GP in the firm. (with many exceptions, of course). There are obviously more examples. The key is to go out and take a risk and let those advantage work for you, while constantly learning from senior VCs for a reality check.

  34. Chris DeVore

    Great post, Fred — every day I learn how much I still don’t know about the investing business. Humbling, to be sure — but I’ve never had more fun in my life, mistakes and all.

  35. Adam Feldman

    Great post, and great comments. Here’s my take on the whole matter:We gain experience in anything when we complete a feedback loop of decision –> action –> success/failure. Many tasks have a quick feedback loop where you can quickly learn from your mistakes and start improving. If you’re a chef and you overcook a piece of meat, you’ll know immediately and you’ll have an opportunity to try again 30 seconds later. In some industries there are even intermediate feedback loops you can use along the way, for example: the code doesn’t compile, so go back and get it right. When you make mistakes, learn from them, and then try again you are (hopefully) getting closer to doing things correctly.VC is an interesting industry because the feedback loops are so stretched out. There are two critical loops and areas for skill development that are worth examining: closing deals and finding opportunities.VCs tend to look at countless companies before they even attempt to pursue a deal with one. As a newly minted VC you might sift through hundreds of companies before you finally find the one. If a more experienced VC swoops in and edges you out, it’ll likely be a while before you have another opportunity where you can apply the learnings from that experience and improve your ability to close a deal.However, the bigger challenge is probably picking the right companies to begin with. The issue here is further exacerbated by an even longer feedback loop: invest –> wait –> struggle –> wait –> successful exit/failure.Union Square Ventures invested in Zynga in 2008. I would say that was a good decision, and one certainly worth learning from. However, that’s a 4 year feedback loop. And what if they had gotten edged out of the deal, then they wouldn’t have had that feedback point at all… four years later.The opportunities for learning and improving as a VC are so few and far between that it makes it difficult to get better. So, as FAKEGRIMLOCK say: GO WHERE FISTS ARE.

    1. fredwilson

      such a great observation. the average hold period is something like seven years in early stage VC. i’m still involved in companies in invested in back in ’98/’99/’00. that’s 14 years if anyone is counting!

      1. Adam Feldman

        So we learn from our actions as best we can, but what about holding onto all of the mistakes and chances in the hopes of learning from them too? I’m thinking of Bessemer’s infamous anti-portfolio. Do you keep anything like that around?

        1. fredwilson

          mentally but not physically

          1. Adam Feldman

            If you’re comfortable sharing some of it, I’d love to see it

  36. Tereza

    At my first venture — this was back in 1992-3 — our main VC was named Andy Gaspar. I think he’d be Fred what you call old school and is my anchor definition of VC.He’d been a seasoned VC already for years, having started as an engineer at Raytheon, then HBS, cut his teeth in the VC business and eventually joined Ronald Lauder to run that fund redeveloping Eastern Europe.Andy was (is!) in the top .0001% smartest people I’ve ever met. And the most gracious as well.He had a system of staying in touch with people, working the network, developing relationships for the long run. Serious golden rolodex and had a serious system to make it work.We lost touch in the late 90’s — frankly I did not stay in touch when I moved into consulting, figuring I was too much of a peon and he’d be bothered.When my wedding announcement hit the NY Times in 2000, I get a congratulations card from him at my office from Andy, saying what a delight it was to see my name, and he wants to stay in touch with what I’m doing. THIS is the old-school VC — class act, and all about long-term relationships and what-goes-around-comes-around. At that time, I was like, damn, that’s the kind of professional and person I want to be. Big impression.Anyway, I’ve met lots of VCs in the last bunch of years. A very varied lot. Some amazing, some seriously unimpressive and wielding inordinate power. Big difference between those who have operated and those who have not (though a few decades of experience is a great equalizer). One day after a many weeks of VC meetings I looked at my funnel chart and realized — I had a zero % hit rate on the young, inexperienced VCs. And almost a 100% callback rate on the older (and frankly bigger name) VCs. Kinda surprising. But made be wonder — this whole pattern recognition thing — are the younger ones more prone to it? Do years of experience and flameouts sensitize you to the ways patterns can deceive.And I’d be remiss in this rant if I didn’t just make this call-out: we need more women VCs. And I don’t mean analysts and associates, I mean partners, and I mean across lots of funds. Decision makers who are not in the minority, not tokens. Women entrepreneurs need liquidity and competition. It will grow the total innovation pie and be good for everyone.

    1. fredwilson

      I learned the VC business from a couple guys like Andy. I’m not like that (to my detriment at times)I appreciate that style.And you are right about needing more women VCs

      1. Tereza

        Well I think the world has evolved and there’s a velocity of deals and movement that is not what Andy dealt with when he asked his secretary to physically cut and mail me that note on paper. The world evolves and so do we.But some of the good stuff we retain from the past can actually turn out to be secret weapons — and I think there’s def some of the good kind of ‘old school’ at play at the Wilson household. At the end of the day, this business is all about people, and finding the ones who’ll do extraordinary things, giving them what they need and then getting out of their way.

        1. fredwilson

          Joanne does stuff like Andy. She is really good at it

          1. Tereza

            Totally. All comes down to a serious passion for people and what they can create.

          2. LE

            Harvey Mackay in “Swim with the Sharks” (80’s book) talked about that. Mackay (if I remember correctly) would always send people notes to remain in contact with them.  He would also keep details on their family, birthdays, what their interests were etc. It was one of the cornerstones of his success I believe he said.

    2. LE

      “Do years of experience and flameouts sensitize you to the ways patterns can deceive.”Speaking strictly non-vc patterns I think you always need to revisit your patterns to make sure they are still relevant and to refine the nuance. In general they are correct and seem as real at the time as “that pain you have that might be something terrible”. The pattern seems almost absolute in your mind when you experience it. I get that “I’m wasting my time” feeling.  Patterns are about efficiency.  You don’t have time to fully vet every situation. When my father did trade shows he could tell pretty accurately who the important buyers were and who would waste his time.  If he got tied up with a “noodnik” he wouldn’t be there for the department store purchasing agent.I don’t like to question the patterns that frequently (for what I do) because then you start to question everything and that causes overload. The thought process slows you down.That said I’ve definitely found cases over the years where the pattern is wrong. One incorrect interpretation came in my first business where a man came in with a plastic trash bag who looked homeless. He turned into one of my best customers – he ran a local art theater and that’s the way he rolled.

      1. Tereza

        I think there are patterns we develop for ourselves to navigate our work and then there are some which, writ-large, take on more power than they’re worth. Probably every VC prides himself in operating of his own specific favor of what may be a broader pattern. If everyone’s operating off the same pattern then you’re just amplifying competition which is a detriment to you. I suppose the best thing is, if you’re going to adjust or even shake up your pattern, be the first to do it, and then stick to that thesis. That’s competitive advantage.

        1. FAKE GRIMLOCK


    3. ShanaC

      Actually, that’s interesting when it comes to callbacks – why do you think that is?

      1. Tereza

        I think the segments were employing different patterns. The older people were seeing something in me the younger ones were not.I also think there’s also awkwardness in a potential investor who’s a generation younger than you. How could they possibly understand my experience? We live in different worlds.

        1. Ricardo Diz

          I guess the same could be said for young entrepreneurs then. Some of them might feel a younger VC partner, one from their generation, can understand them better than an older/more experienced VC, since they live in the “same worlds”… Somehow, I think this is not the norm.



      1. LE

        “RELY ON WHAT WORK BEFORE “Nothing wrong with following a formula that works. As long as you invest some time, energy and money into experimenting with the future.  Many times the thing that prevents people from moving forward is simply being to busy keeping up with business day to day (could be Fred with to many meetings or could be the local wholesaler who has plenty of orders) to invest time in the future.I remember in college interviewing entrepreneurs. One had a fairly large successful wholesale restaurant supply business and had no computer system. That wasn’t that unusual back then (it was the start) but I remember specifically the fact that they were so busy “management” didn’t have time to stop using the manual system and computerize. This was a common theme.  While some companies didn’t have the money to computerize (was very expensive back then) others had the money but didn’t have the time to get their hands around the project and get it implemented. 

        1. FAKE GRIMLOCK


        2. kidmercury

          gonna side with LE over fake grimlock in this beef. the best way to know the future is to study the past. 

    5. Donna Brewington White

      I wonder if those patterns might also lead to your point about needing more women VCs.  Seems that others have asked a similar question.  Funny, a few years ago, just conceptually, the idea of becoming a VC was very appealing.  It still is, but when I began to explore and observe what it takes for entry, I discovered that I am so far off the pattern — even if I was a 35 y.o. white male which obviously I am not — that it wasn’t really conceivable.  And you can’t imagine how hard it is for me to concede this…to concede anything, really.  (Unless, perhaps, conceding a mistake.) Doesn’t mean I won’t find another way to participate.  Just probably not as an investor (unless an angel).So even though it may not benefit my own career, I do hope to see more women enter VC — and not for the sake of “the cause” or “the ratio” — but because I sincerely believe that this would be beneficial to society, the economy, the marketplace of products and ideas, innovation — especially innovation.  It’s good capitalism.  And, besides, I have a daughter (as well as sons).  Anything more I could say on this, I’ve already heard you, Fred and others say much more eloquently.  You already know this, but just as a reminder, count me in if ever there is a way I can be of support to this idea.

      1. Tereza

        I looked into VC a while ago and although I thought I might be very good at it, I concluded that given my age, financial status, market timing and gender there wasn’t a chance in hell it would ever happen. So I moved onto other things. :-)But — yes — if there is some radical shift in the ecosystem I will definitely keep you in mind!



        1. Donna Brewington White

          I’m borrowing the concept of “pattern” from other comments in the thread. But I can give you my interpretation. But I don’t know whether you are referring to a definition, description or example?

          1. FAKE GRIMLOCK


  37. Joshua Sortino

    People in general should always try to learn from more experienced professionals in their field or craft. Relevant wisdom is more beneficial than any other type of advice. Sometimes those connections are what end up changing your life.

    1. obscurelyfamous

      There is nothing quite like impassioned mentors who want to improve themselves by teaching someone else.



  39. adamludwin

    I think founders win when they have both younger and more experienced VCs as investors. 

    1. obscurelyfamous

      It’s the dichotomy that makes this arrangement successful. Perspectives from different ends.

    2. fredwilson

      there certainly are a bunch of benefits from that

  40. CJM

    I come to this post from a slightly different perspective. I run a fund-of-funds focused on venture/growth, so we are constantly evaluating the ever-changing landscape of VCs. One issue that always presents itself is determing not just the experience of certain VCs, but analyzing this experience in the context of the cycles in which they’ve been investing. For example, back in the late 90’s the question we were asking was whether a newer VC was able to identify the losers in their portfolio. For those who hadn’t gone through a full cycle, many had only seen winners/up-rounds/high exits from their portfolios.Fast forward a decade, and the question was turned on its head. Now the question asked is, after a decade of poor returns and writeoffs/down rounds, did the newer VC have any experience in picking and riding winners.Layer on top of this the very real issue of succession in many of the “brand name” funds, and the challenge to pick the right VC has never been more difficult than it is today

    1. fredwilson

      the GP/manager that I like best is the experienced VC(s) setting off on their own and doing a brand new firm/fund

  41. Donna Brewington White

    I first came to AVC to learn more about VC and for a closer connection to the entrepreneurial world (my true home), but it didn’t take long to discover that many/most of your posts have relevance and offer wisdom that is applicable well beyond the subject matter. This post is the perfect example.  Regarding the subject matter, I think I have some sense of how invaluable this advice is for actual VCs which makes it even more meaningful (and beneficial) for the rest of us. The more that VCs can learn from you, the better the startup ecosystem.

    1. fredwilson


      1. Robert Holtz

        Donna is right.  Can’t thank you enough, Fred.  Grateful for you.

    2. Robert Holtz

      VERY well said, @donnawhite:disqus.And for me, the added dimensions of meaning and life relevance on AVC and about Fred were also unexpected but wonderful surprises that keep me coming back to be a part of it all.I feel lucky to have stumbled upon it and to be welcomed in.

  42. Brian Sirkia

    Fred (or anyone else is this awesome commenting crew) – As an entrepreneur, do you think I should be looking for an old wise Jedi-VC, or some younger upstart? I understand you probably have you’re own bias, but by the sound of it I might be able to get a better deal (for me) from a younger VC.I’m sure it all depends on a case-by-case basis, so what do you think should be the motivators (ie. amount of mentorship wanted/needed, VC involvement wanted/needed, $ vs. experience tradeoff) should be?Thanks again for all the great posts.

    1. Ric Fulop

      Brian, my advice is cast a wide net and pick the people you really like who truly love what you are working on. Many ventures can take a decade and you get stuck with your investors after a short courtship.

    2. fredwilson

      first and foremost, find someone that shares your passion for your project. that must come before all else. but all things being equal, i’d go with the experienced VC

  43. David Petersen

    Reasonable Doubt album.  Great all the way through.

    1. fredwilson


  44. Mike Duda

    Fred,You are, likely hand-down, the most prestigious VC in NYC. You’ve earned that right, having done this before it was en vogue and having successes and lessons learned before many even combined the letters V and C for professional consideration.With that very respectfully said, let’s look around at a diverse set of business evolutions.* The NBA Draft used to be filled with four-year college stars (or three for those who couldn’t play varsity). Now the draft consists of one-and-done 19-year olds and European players we’ve never seen.* “Go to college” was the rallying cry for those who wanted to have a successful career (and still is). And maybe Bill Gates was the first to break the mold to drop out of college to start Microsoft, but hell, one of your investments is lead by David Karp who had no desire to sniff college. Perhaps he will become the poster boy of Peter Thiel’s desire for those to see more 18-year olds fill out SEC than SAT docs in the future as he has argued for.* Look at NYC. Accelerators are now more popular than MBA programs for business street cred. The Mayor is showing up at Demo Days as often as he is Diploma Days. Two economic meltdowns in a decade have just changed the fundamental way that, well, everything is done.So when I read this post, I sense there may have been a specific incident that a young, talented VC may have done something wrong, learned a lesson or whatever. But guess what. That’s a business reality in no matter what business one’s in. And quite frankly, my gut – yes, pure gut – says the “ecosystem” is better with the Ben Lerers, Jared Kushners and David Tischs doing the things they are doing (NOT that you called them out).You invest is businesses that build communities and disrupt. And the same could be happening to the VC marketplace. As a VC, if you have the most money and/or respect – and UVC deservedly commands a lot – great! But in an era where things are changing across all businesses, and venture is not immune, some, new and younger VCs will emerge that might be a bit different and need some fine tuning…but don’t you think it’s better to boost and champion than to dial into certain faults? Why take such a negative tone rather than a build-up call-to-action?

    1. fredwilson

      because it’s what i see in the market and entrepreneurs and VCs should hear it from me

  45. infoarbitrage

    Fred, this is a very important post, and something which you know I think about all the time. There is no formula for being successful in the venture business. But I do think there are some common characteristics that are shared among those who have demonstrated success through cash-on-cash returns and reputation among key constituencies – entrepreneurs, strategic partners and acquirers, peers in the venture business and Limited Partners.The best investors I know are amazing listeners. They are less interested in demonstrating their intelligence and more concerned with deeply understanding an entrepreneur’s idea and engaging in a meaningful dialogue which, regardless of investment decision, generates real value for both parties. They also generally cultivate great mentor relationships. While they are invariably mentors themselves, they continue to work on upping their game, even when it appears to outsiders that there is little that they can learn given their success. Great VCs also tend to have a genuine humility that respects the complexities of the business and the fact that while experience and historical success are great, there is no assurance that they will continue to adapt and remain current, relevant and value-added as paradigms shift and markets rapidly evolve. Finally, truly successful investors have a fundamental respect for founders, regardless of whether or not they like their idea. It is a basic appreciation for the passion expressed by those pursuing an idea that drives them to start a company. It is a holy mission. The mere effort deserves respect if done with thought, honesty and if it emerges from deep within.These characteristics, I believe, are more frequently found in somewhat older investors simply because they have more data and more failures. Failures force introspection and perspective that is hard to acquire in any other manner, and EVERY experience venture investor has taken their lumps. It is a price every investor pays at one time or another. It is also the case that more experience generally breeds awareness that the investor doesn’t know everything, and that cultivating a web of mentors is an essential element to taking one’s skill and practice to the next level. However, I am not willing to say that a young, driven, forward-looking venture professional is unable to accelerate their maturation (and ultimate success) by doing these things. I think they can. But there is little doubt in my mind that experience and the data it generates is a helpful asset in becoming a successful venture investor. But what the hell do I know – I’ve only been doing this for eight years. The comments above merely represent my experience to date and observations of those whom I perceive to be successful and whom I respect a great deal.

    1. fredwilson

      i completely agree Roger. both about needing to have the failures. and also about the next generation being able to accelerate the learning process.

    2. William Mougayar

      Great add-on to Fred’s, but that young VC must be able to articulate their value-add to the entrepreneur. I’ve been surprised by the lack of good value proposition from younger VC’s when I asked them “why should I let you invest in my company”? The most lame answer I received was “I have 1,000 followers on Twitter”. As an entrepreneur, I think the #1 value I look for in VC’s whether young or older, less experienced or more,- is their Network and the doors they can open for me. Close second is their opinions and knowledge of the market we’re in, so they can see things ahead that I may not be seeing yet. The rest I think is a wash. Fred said it several times before: The entrepreneur is the VC’s client, and therefore the VC is there to help them, and that kind of help starts before the investment transaction.

  46. Ricardo Diz

    I think the bottom line message is: one should keep learning. So, on one end, you can grow/learn as a young person within the industry (if you have the chance to enter the VC world young) – e.g., learn with experience VCs in board meetings, get exposed to different business models and startup/team dynamics, …On the other hand, one can always learn by having a different experience elsewhere, entering the business at a later stage. I’m sure there are a lot of skills to learn to become an awesome VC, and most of them can surely be learned with a diverse professional experience. And yes, and I do mean beyond being an entrepreneur. One can learn (and gain experience) about business, entrepreneurship and investments in a lot of ways. I’ve always made my professional decisions having into account how much I would learn. I believe that’s probably how you get to become a 40 – 50 years old wise man such as Fred… I’m not sure there’s a “best path” to get there (i.e., wise man status doing what you love), but I sure think learning has something to do with it. Case in point, both Fred and Ben Horowitz got there… So, I hope that, as long as one keeps learning and working on interesting projects, the likelihood of things go well professionally is high.

  47. george

    Funny thing, in business school they really don’t teach you the art of soft skills or the language of business in the c-suite. Mentorship makes a measurable difference; it can save you from yourself!I believe people rise higher when they make the commitment to share their wisdom and resource others. Thankfully, the contributions on this site have been a wonderful resource…



  49. kidmercury

    i really enjoyed hearing about you school youngsters and take their deals from them after they do the leg work……lol that sounds like funjay z is into some weird creepy stuff…..either he is toying with satanic imagery just for marketing and to get people like me talking about it or there is something much more sinister at work. it’s a real shame andreessen horowitz brought on a criminal like larry summers as a special advisor…..a guy who advocates big economies moving their polluting industries to poor economies, a guy who served as chief economist for the world bank where he helped implement “economic hit men” policies (get poor countries trapped in debt so the majority of their government spending goes to debt repayments….and then we wonder why those countries are still “developing”……they been “developing” for decades now……) now you have losers like him sitting on the board of square, joining andresseen horowitz….. can’t shake the devil’s hand and say you’re only kidding.    

  50. Max Yoder

    This is a great post in and of itself, but the VoiceBunny guy rapping was the highlight for me.

    1. fredwilson

      voice bunny is building a following here at AVC

  51. jimmystone

    Epic post.

  52. VictorPascucci3

    Excellent post.  Nice counter point to Gurley’s latest blog.

    1. fredwilson

      i missed that. going to find it and read it now

      1. Victorpascucci3

        here you go…

  53. CJ

    I can’t believe I missed the day when you quoted one of my favorite songs on AVC. Nicely done at that!

  54. ericthet

    Could you elaborate on what are some of the meaningless things that young VC’s fight with entrepreneurs about?

  55. ceonyc

    So… thanks!  http://www.thisisgoingtobeb…

    1. fredwilson

      great post Charlie. your blogging has improved a lot over the years. you are ruminating more. that’s a really good thing.

      1. ceonyc

        Less posts, more quality.Learn well, I have.