The Ledger
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Venture math should focus on probability distributions, not ownership percentages
“But the point that I was making with Michael is that ownership really isn't the math that we use to kind of think about how we invest. We really think more in terms of number of investments and the likely probability distribution of finding large outcomes. And…”
Sam Altman's advice to wait for YC is selfish and poor
“I think that's kind of laughable and actually probably really poor advice for entrepreneurs. Usually I think Sam and YC in general is an amazing program, and they offer lots of benefits and advice. In this particular case, I think they were being a little bit …”
Predictably hitting unicorns requires investing in 200 to 500 startups
“If we find, you know, unicorn only two percent of the time, or heaven forbid, one percent of the time, our portfolio size needs to be a minimum of 50 to a hundred to really have a shot at that, and I would argue, actually, we are aiming for more than one unico…”
Early rounds for Lyft, Credit Karma, and Twilio were uncompetitive
“When we invested in Lyft out of FB Fund, I guess it was called Zimride at the time, and when we invested in Credit Karma and Twilio they were not really that competitive rounds, even though, you know, the founders were compelling most of the time.”
Overemphasis on venture signaling indicates underlying company performance issues
“My perspective on this is typically that if the founder or other investors are more worried about my investment decision than the baseline performance of the company, there's already likely some kind of problem there.”
500 Startups has invested in over 100 Y Combinator companies
“We've been investors through our seed investment program in a bunch of YC companies, over a hundred. I think we're actually one of the top three or four investors in YC companies over the years.”
McClure passed on investing in Uber multiple times, starting at seed
“Clearly Uber was the deal that I totally fucked up. Travis gave me the opportunity to invest in June of... The reality is I didn't invest multiple times, not just in the seed realm, so it's probably my mistake multiple times over.”
McClure's angel portfolio returned 3x without any unicorn exits
“So in my angel investment portfolio, I made about 13 investments. I did some advisory work for a few other companies, but let's say it's maybe 15 companies. There were no unicorns in that group of companies, but I had three What we would call centaurs or a hun…”
500 Startups targets 1% to 5% ownership in seed rounds
“The typical ownership that we hold in most of our seed round investments is probably between one to five percent. Maybe a little bit higher in some of the international geographies where valuations are lower. For Accelerator, it might start at around five to s…”
McClure turned $300K across 13 angel deals into three $100M+ exits
“Started doing angel investing as I was leaving PayPal in 2004, kind of doing that part-time recreationally, I guess, but invested in about, I guess, about 13 companies over the next four years, put about 300,000, maybe total, and got a few wins out of that, I …”
SlideShare and Mashery seed rounds were not competitive
“SlideShare and Mashree certainly were not, like, super competitive rounds although, you know, strong team and capable founders.”
McClure invested $25,000 into Mint.com's Series A round
“Mint.com, I guess, was probably a little bit competitive Certainly by the time the A round happened, I put about 25 K into the A round, but I'd already been, you know, helping the company here and there a little bit.”