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How helpful is venture capital experience to building startups?

My experience in venture capital

As I’ve blogged about before (though quite a while ago), I spent some time at Mohr Davidow Ventures as Entrepreneur-in-Residence – for more about what that job is, read here and here. A couple years before that, I had spent some time at MDV in their Seattle office, towards the end of the dot com bubble, as an analyst/intern. Both experiences were a ton of fun, and I justified the ~3 years in venture capital where I could have been starting companies as an education that would help me later on.

Now, a couple years later, I thought I would reflect a little bit on where the VC experience helped and hurt me relative to actually trying to build a startup. The net of it is that the time was mostly helpful, and a big chunk of knowledge transferred over, but it was mostly high-level stuff. A lot of running a startup involves mastering nitty gritty details, and the VC experience did nothing to help there :-)

For the lazy/impatient, here are some key things I’d say where it can help:

  • It helps with traditional investor/entrepreneur information asymmetries
  • Lots of tactical holes still exist
  • Investors can often oversimplify startup issues, or overmatch on patterns
  • Helps with understanding of investor motivations, which can otherwise appear mysterious

Let’s dive into each of these issues below.

It helps with traditional investor/entrepreneur information asymmetries
Some of the stickiest situation for entrepreneurs are cases where they infrequently encounter a situation, which generates information asymmetries where an investor often knows much more. These asymmetries often involve events like fundraising, selling a company, recruiting executives, etc. In the positive case, investors can be helpful and coach startups through these times, which is great. In the negative case, it provides an opportunity for investors to engage take advantage of naive entrepreneurs, which is not so great. This is why sites likes VentureHacks and TheFunded are useful, because they help even the playing field.

Part of the problem for me, however, is that only the General Partners at VC firms end up actually doing deals. All the associates, EIRs, etc often participate, and you see the final deal terms, but rarely get to see all the back-and-forths that end up with the deal getting done. This creates familiarity with the process, but not the battle-tested experience of having gone through lots of nitty gritty negotiations. But even then, you hear about, and know what the levers are, so everything is less mysterious.

(But like I said, VentureHacks and TheFunded are great, and I only wish there were sites with that level of candor about this obscure industry)

Lots of tactical holes still exist
One area where a venture capital background didn’t help at all was dealing with all the tactical details of getting a company off the ground. In particular, the biggest hole by far is hiring and managing people, which gets abstracted at the financial level. Someone in VC-land can talk abstractly about strong teams, but you don’t have to go through the process of interviewing dozens of people to find the right person.

I’ve written up some of my thoughts here on this topic, in a post called “Building the initial team for seed stage startups” where I talk about a couple points I’ve come to believe:

  • Hiring T-shaped people versus specialists
  • Try to get doers
  • More candidate flow solves a lot of problems
  • Interview for the actual work you’ll be doing, not skillset trivia
  • Raw intelligence is just one factor – don’t overestimate it

There are also some even deeper questions that are unanswered by VC experience, such as how you actually build out a suitable recruiting pipeline? Or how do you interview people where you don’t have the skillset to comment about their competence one way or the other?

I would say hiring is probably one of the most difficult areas to master, and although there are other block and tackle issues – accounting, leasing an office, operations, etc – getting the right people is just a very hard topic. It’s not a surprise that so many startups struggle with it.

Investors can often oversimplify startup issues, or overmatch on patterns
Venture investors often spread their time across a whole number of industries – you look at their websites, and they’ll say they invest in everything from consumer internet to clean tech to life sciences. MDV was no different, and we were responsive to companies across a large number of markets. One VC explained to me early on that you have to respond to what entrepreneurs are producing, and if you get too “top-down” about a particular industry, it gets easy to overinvest in a bunch of mediocre companies rather than trying intently to just focus on finding the best single team and opportunity you can.

Mike Moritz has talked about this before:

Moritz waxed philosophical by comparing venture capital investing to bird spotting. “I rarely think about big themes. The business is like bird spotting. I don’t try to pick out the flock. Each one is different and I try to find an interestingly complected bird in a flock rather than try to make an observation about an entire flock.” For that reason, while other firms may avoid companies because they perceive a certain investment sector as being overplayed or already mature, Moritz said Sequoia is “careful not to redline neighborhoods”.

Continuing with the ornithological analogy, Moritz pointed to Cisco and said, “There’s a lot to be said for investing in the ugly duckling.” When Don Valentine led Sequoia Capital’s investment in Cisco, many others had passed on the husband and wife founding team of Len Bosack and Sandy Lerner.

One of the difficulties for me personally in seeing a wide variety of companies all the time was that it was impossible to not start to pattern match and draw conclusions about the companies that were probably false. You end up in the proverbial “mile wide, inch deep” level of knowledge about that industry, which makes it all too easy to make generalizations. Similarly, there is a drive to simplify your understanding of a company, since you have to socialize it and talk to other venture partners about particular spaces and companies, which also causes oversimplfication.

Contrast this to startup life, where you end up devoting yourself to one company (which may encapsulate many ideas, as you iterate) for the period of years. You end up diving very deep into situations, and learning about all the different details tradeoffs that cause products to be successful versus not.

Helps with understanding of investor motivations, which can otherwise appear mysterious
Finally, one area where having a venture background helped a lot was understanding investor motivations in general. Entrepreneurs ask a lot of great questions, like, “Why don’t investors want to invest in my idea X which will be highly profitable?” or “Why does hot consumer internet startup X lose tons of money but is valued so much?” The answers to these questions drive a lot of investor behavior, which can be mysterious if you don’t know what’s going on.

The interesting part is understanding why VCs are structured the way they do, why they have a 1 in 10 portfolio strategy, and how they think about their Limited Partners. They have a boss too, of course :-)

The major point here is that building medium-sized, profitable companies that aren’t growing quickly is not really part of the venture capital model. Knowing that can help with all sorts of things, such as massaging your business plan into something “sexy” that investors will respond to. Similarly, it will help get everyone aligned on major decisions, such as financing events, exits, exec team building, etc.

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