A: For decisions that fit into the core of our strategy (first instutional investor, significant ownership -- usually what most would call Series A, or many "large seed" deals) we have a fairly unusual "sponsorship" model. Our team is highly collaborative in evaluating an investment opportunity, but the individual partner is given both the authority and responsibility to make the decision. This enables contrarian or minority ideas to flourish, and mitigates the natural tendency to "over-defer" to others on a hard decision.
For true small seed investments, the process is simpler (and rarely something we do). For later stage and larger checks -- not our core focus, but pursued at certain times -- we have a somewhat more involved decision-making process.
A: Most of the entreprneurs I've talked to who went through YC are positive on the experience. Primary benefits cited are: the network/camraderie, the cadence it drives you to operate at, and the boost to your fundraising. The negatives I have heard voiced are: the cost in terms of dilution for what you get from it (in some cases), and for some people in their 30's or older felt like they were at a different life stage than others in the class.
As an investor, I've felt there were quite a lot of very talented individuals coming out of the program, and so it's generally a positive if a deal comes from there. They push people to settle on an idea quickly, and I am less positive about that -- personally I believe that if you think strategically long and hard you can often come up with a real insight, and I'd rather build a business around that (and did in the two businesses I operated in before VC.) In my case it took me 1-2 years each time to find the idea, but it was well worth the wait. So I am cautious about a program where many people come in with no idea, or drop their existing idea, but are pursuing whatever they came up with in a few months -- I am cautious that it will be a well-packaged version of a mediocre opportunity. But it's on me as an investor to figure that out, because clearly there are some great ideas in there as well.
But I guess to frame back to your question: a reason not to do YC might be, if you don't already know what business you plan to build, you could through YC become "locked in" to the best idea you have in the next couple of months, and I would be concerned for you that if you instead took longer to spot an opportunity, you might find a much better one. But there is definitely a different school of thought that you begin by getting started and you can always pivot later -- not my view but it has worked for some folks.
A: Medium bad.
I remember this from mid-late 2000. Luckily, my business was fully funded. But in September 2000 I knew many folks who felt like the market was terrible, as it took longer to raise money and valutations were coming down. But by 2001, they sure wished they'd taken money when people still actually wrote checks.
The market has definitely come off of the peak. Who knows where it could go -- if the stock market ticks up, this could be a flash in the pan. But your most important job as a founder is to stay alive long enough for something good to happen to you. Minimizing dilution is way less valuable than staying alive, because if you live long enough, you will probably figure something out. So even though the market might improve in the future, I would not encourage you to take much risk waiting for it if you can raise now. VCs have slowed down but are still writing checks, and at certain points in cycles, they seem to stop writing checks altogether.
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