Would you take money from a 28 year old?

I was reading this morning that Matrix Partners has brought on a new partner. Jared Fliesler is all of 28 years old, but has already held down senior roles at Square and Slide / Google. Impressive stuff. I’m sure the guy is brilliant, but I think 28 is just too young to be a partner in a venture fund.

Have you ever seen a sports coach that is younger than the players? Me neither. And that’s the right analogy here. The best VCs act as trusted advisors, mentors and connectors. To do that you need to have been around a lot, seen a lot (of successes and failures) and know a LOT of people.

Also, no matter how brilliant or overachieving you might be (lord knows I have met many people who accomplished way more than me before they hit 30), there’s a certain perspective that comes with age. Perhaps its the humility that comes from changing diapers, or maybe it’s purely a function of time. All I know is that in my 20s, I thought I knew everything. I was wrong.

Finally, the World doesn’t need another VC. We are in dire need of people who know how to operate and are still young and driven enough to do that. That’s a separate point I suppose.

Anyway, maybe I’m just getting old, but I would not take money from a 28 year old VC. Would you?

  • http://context.io Bruno Morency

    Late to the party but seeing how the comment thread tends to disagree with the post, I’ll comment anyway.

    If this guy is brilliant, amazing at product management and can bring a lot to my product, I’ll try to hire him not raise money from him. I don’t expect, nor do I want, my VC to manage my product. Leading product and user growth isn’t a part-time role. Thinking becoming a VC means you can do for 10 companies what you used to do for 1 is delusional at best.

    What I expect and want from my VC is help through the inevitable struggle I just signed up for. You can’t claim to bring more than capital if you haven’t faced that struggle many times yourself. I’m not talking about a couple failed A/B test experiments, a rough month or a bad quarter here, I’m talking about *years* where nothing was working as you wanted them to. You had to layoff people you hired yourself. You had to replace key players that jumped ship. You maybe even had to recapitalize the company or even worse, close it down, pick yourself up and start all over again. That kind of shit take years to happen and years to clean up.

    I don’t care if the nature of the product and technologies evolved in the last 10 years, there are things you need to go through to go from Founder to CEO that haven’t and won’t change. So, to answer the question, would I take money from a 28 year old? No.

    • http://startupcfo.ca/ Mark MacLeod

      Well said Bruno. I completely agree.

  • http://www.facebook.com/michael.carpentier.7 Michael Carpentier

    Extremely well said and true. We need 28 year olds out in the field…so one day they can, if they choose, to become great VCs. The coach analogy is dead on!

  • Enterprising Canuck

    I just met Jared last week before his becoming a VC was officially announced. Jared has a *ton* of relevant experience to bring to any early or growth-stage software entrepreneur. He is helpful, humble and – as you speculated – brilliant. He has a rare mix of operational, HR and product knowledge that, combined, I haven’t encountered in a lot of investors, and I’ve had the good fortune to meet and interact with many of our Industry’s most respected investors.

    His recent experience and successes are *fresh* and relevant to me. Especially in enterprise, where there is a tectonic shift occurring, I see age bias a different way: There are some VCs whose experiences and successes 5+ years ago now are really far less relevant to the way successful businesses are being built today. So any bias towards age should swing both ways.

    The thing that irks me about the way you’ve positioned this piece is to use Jared as the inflection point for a generalized question. And when deciding who to take money from, trying to answer a generalized question is a really bone-headed move. I’d take money from a 19 year-old or a 91 year-old, if after spending time with them, I was convinced they brought value-add to my business.

    I’m choosing to answer this anonymously as I’m just raising my next round but let me say that I certainly *hope* that I am lucky enough to have Jared as an investor. And I say this being a few years older than him and reflecting on how between 28 and 32, it was a period of hyper-maturation for me.

    • http://startupcfo.ca/ Mark MacLeod

      Hey Tom,

      One of the reasons why I was keen to get back to operating (from investing) was that I felt the longer I stayed out of operating the less relevant I would be as an investor. So, your points about the shifting landscape resonate.

      But here’s the thing: The best, most backable entrepreneurs already have the landscape figured out. And if they don’t a VC won’t figure it out for them given that he or she is very part time on any one company. Those great founders already know how to build a killer product. What they need help with is becoming great CEOs, building amazing management teams and other things where experience helps a lot.

      I have no doubt that he’s brilliant. And this post is not about him. Just a springboard to pose a question. If you think that’s “bone-headed”, you’re entitled to your opinion.

      • Enterprising Canuck

        The way I read (perhaps wrongly) is that you’ve made this post about him by asking a generalized question but using a single person as a reference point to that question. We’re completely agreed: Great entrepreneurs need help becoming great CEOs, building amazing management teams and helping orient a CEO and their team to the different challenges that come with scaling a business. Whether an investor can contribute to those challenges in a meaningful way is the question to ask. Anything else (such as a person’s age) is just a distraction in evaluating that person’s ability to make those contributions.

        • http://startupcfo.ca/ Mark MacLeod

          I think its hard to judge this until you’ve been a VC yourself. It’s a tough job. And the post is not about him specifically. I don’t know him.

        • Enterprising Canuck

          I’m confused as to what you’re trying to say with this post, then. It seems like your statement boils down to “he’s not old enough to be a VC.” And besides, I don’t think anyone coming *into* the game should do so wanting to “be a VC.”

          No anyone entering that role for the first-time should do so because they think they have something meaningful to contribute to early and growth-stage companies within the contexts and constraints of that role.

          As my Grandfather was fond of saying “Time will tell.”

  • http://www.onceabeekeeper.com/ Kevin Swan

    I have to disagree and, to state the obvious, am biased here as I am a younger guy in the VC world. These days entrepreneurs are very drawn to product-focused investors and, on the web, I don’t think that there is a strong correlation between age and great product knowledge. Most great product/designers I know are under 30.

    I struggle to see a correlation between age and succes in VC. Some VCs have had better track records when they were younger. Some get better with age. What is more important, and LPs understand this, is having a great mix of partners in a fund and that includes a mix in age. Benchmark is religious about this and bring on a 30 yr old partner, most recently Matt Cohler, every 5-7 years.

    It is also very important for a fresh, young VC to have tremendous support from his partners. I don’t think that Jared will be left on his own to figure things out, but receive tremendous mentorship, guidance and feedback from the other Matrix partners. I didn’t have intentions to be a VC until I was 40 and had apprehensions about getting in to it while still in my 20s, but in the end I saw the support, mentorship and opportunity the partners at iNovia were committed to giving me.

    Lastly, while VCs are looked to for answers, guidance and advice I have learned that a teacher-student relationship between an investor and entrepreneur is not a necessarily healthy thing. I have also learned that the best VCs are better at asking the right questions, not necessarily always trying to have the right answers. The best entrepreneurs I have had the privilege to work with don’t want to be told what to do – they want to be held accountable, get asked the hard questions and have their investors/board empower them at every opportunity.

    I still believe that it is a very steep learning curve being a VC – not only in making great investment decisions and adding value to companies, but even in all the behind-the-scenes work that never gets talked about (admin, LPs, fundraising, etc.). I think a young person can succeed, but they have to come in with humility and a massive appetite to learn.

    • http://startupcfo.ca/ Mark MacLeod

      Great comments Kevin.

      For sure, the best investors in young, web companies today are likely strong product people.

      It’s funny how quickly we context switch. A few months ago, with my Real seed VC hat on, I wouldn’t have thought twice about this guy being a partner in a tier 1 fund. But now with my FreshBooks hat on, I’m thinking about what it takes to build a billion $ company. It creates a different set of filters about who you surround yourself with.

      Finally, I totally agree that VCs should not be telling people what to do. That’s the path to mediocre investments. But even to ask the right questions you need to have been around the block a lot.

      • http://www.onceabeekeeper.com/ Kevin Swan

        You hit the nail on the head about building a billion dollar company. I find that my learning curve pretty much follows that of a growing company. More to learn and different challenges as companies grow. Also a good reason to value the particular VCs at each funding stage – seed, Series A, growth, etc.

  • http://twitter.com/iparamonau Ivan Paramonau

    Surely I would take money from 28 year-old, … if I was 20.
    If I was 20, I’d probably not even listen to anyone older than 30.

    Oh, those good times.

  • http://www.facebook.com/chijs Marc Van Der Chijs

    Generally I agree with you Mark, but considering that founders seem to be getting younger each year Jared may be the right person to work with these fresh graduates or founders who did not even go to college. If I would be an entrepreneur in my 30s I would probably not take money from him, but possibly a 20-year old may prefer to work with a 28-year old instead of someone in his 30s or 40s.

    • http://startupcfo.ca/ Mark MacLeod

      Yep. For sure he will resonate with young founders. But look at Howard Morgan. He’s at one of the hippest funds going – first round capital. And he’s up there in age

  • http://twitter.com/karam_n Karamdeep Nijjar
    • http://startupcfo.ca/ Mark MacLeod

      But an important one.

  • http://twitter.com/mike_ivey Michael Ivey

    Your point is valid, but allow me to offer a counterexample… Jon Daniels is currently one of the most successful GM’s in the MLB having taken the Rangers from mediocrity to back to back world series appearances in a very short period of time. He took over that position at (wait for it)… 28 years old! http://en.wikipedia.org/wiki/Jon_Daniels

    • http://startupcfo.ca/ Mark MacLeod

      Every rule is made to be broken. That is a great example.

      • http://twitter.com/danielharan Daniel Haran

        That’s a great thing to say when you don’t want evidence to change your biased point of view.

        What would it take to actually make you believe that your argument is wrong? What is it about perspective that requires you to be old and can’t be obtained any other way?

        Note that you would find your argument to be completely unacceptable if it was made about women or an ethnic group. Really not sure why you think age should be any different.

        Youth today are inheriting a broken economic and political system as well as catastrophic climate change. Playing the age card to further disenfranchise them isn’t the least bit progressive.

        • http://startupcfo.ca/ Mark MacLeod

          Of course it’s a bias. But one based on facts. Am I saying that you cannot be a VC unless you’re old? What I’m saying is

          - most VC backed startups fail
          - the best founders choose the best VCs to work with
          - experience matters in order to help startups succeed and in order to have a profile that is attractive to great founders. That experience should include failures and successes

          All of this just takes time.

          The reason I had great deal flow as a VC is the fact that I have done a lot. I started in this space in my 20s. But experience takes time. There’s no avoiding that.

          Don’t go lumping gender and politician stuff in. It has nothing to do with my point.

          Finally reflect on your own experience to date as a founder. And ask yourself what you could do better today with more experience. There’s no substitute for experience.

        • http://twitter.com/danielharan Daniel Haran

          Depends on how you qualify old. You originally wrote “I think 28 is just too young to be a partner in a venture fund”.

          When you accepted an entrepreneur’s request to meet over coffee, most did not know of your experience. Your visibility and accessibility had much more impact than any experience. Fliesler certainly has more visibility; let’s see how he handles accessibility.

          Where experience should help is in advising companies, it’s not clear that Fliesler’s two successes are much worse than a mixed record, especially if he focuses on only the early growth stages as he’s pledged.

          I’d submit that gender bias is a relevant comparison (not sure where you get the politician part), even if gender bias is now less OK than age discrimination. Confronting such biases helps us understand exactly what we think is necessary for success.

          Cause if what I need to do to increase my success is learn more humility and the best way to do that is to change diapers – sign me up. Why wait until we happen to have children (if ever) to get those useful attributes? Same for just about every other trait or knowledge that would fall under that nebulous “experience”.

        • http://startupcfo.ca/ Mark MacLeod

          “old” is relative. In fact my mother-in-law has a great saying: “old is 10 years older than you are”. I won’t restate all the reasons why I think age is an advantage as a VC.

          Gender bias is not relevant as it is just that – a bias. Women have demonstrated themselves to be as good or better than men at most things. There is nothing to prove that relative rookies (i.e. younger people) are better than older ones – especially when it comes to dispensing advice – one of the primary jobs of VC. Gladwell’s 10,000 hour benchmark (http://en.wikipedia.org/wiki/Outliers_(book)) can’t be faked.

          As for the diaper milestone, it’s just how life progresses. If you and I have this conversation again in 5 years, it will be completely different because our perspectives will be different.

      • http://twitter.com/mike_ivey Michael Ivey

        I’m a huge Rangers fan so I had to offer that up as an example. I’d wager that this is by far and away the exception though…

        To your point however, we are in the midst of a small angel raise, and I actually agree with your comment. In a world where time equals money, you generally hope that your investors can offer some degree of assistance in addition to the check. Having an investor who a) knows your space b) knows other investors in your space c) have been there and know what it takes, etc… really just kills two or three birds with one stone.

        Most <30 year olds can't offer this, so all you're getting is their money.

    • http://www.onceabeekeeper.com/ Kevin Swan

      Add Theo Epstein to the list with the Red Sox’s last decade.

      • Mike Potter

        Alex anthopolis is only 35 now and has been gm for a few years. I don’t think age matters that much. I think experience, intelligence and value would be the most important. And experience would be tougher for someone so young.