The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 55 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Maples: Venture outliers usually start at low seed valuations
“I believe that the outliers usually start out at a low price, because they're outliers. Because they're non-consensus and right. People tend to believe that the world is divided between low price deals with low upside and high price deals with high upside. I d…”
Maples: Most VC Funds Have at Most One Great Investor
“The problem with most firms is that they have less than or equal to one really good investor, and then they force the, what's called the limited partners or the LPs to buy the bundle of everybody else who's not a good investor.”
Maples: Floodgate's best startup deals have historically been their cheapest, not most expensive
“No. Actually the reverse is true, but I don't know if that would still be the case.”
Maples: VCs must prioritize LP fiduciary duty over bank loyalty
“Yeah, and I mean, like that's not the decision I would have made, right? I'm not gonna judge who made what decision, but my view is that it's not my money. And you know, if I was the Stanford Endowment, if I was you know, Sloan Kettering, what would I want Flo…”
Maples: Floodgate initial check writers cannot allocate follow-on reserves
“We have a partner dedicated just to follow on investing, and so the person that writes the first check Doesn't get to decide who writes the follow on check.”
Maples: Startups should target at least three years of cash runway
“I like to assert it should be a minimum three years.”
Maples: Skipping startup steps leads to fake growth
“I believe that you can't really skip a step. You got to have an insight before you do customer development, and you got to do customer development before you do smart growth. And so to the extent that raising too much too soon Causes people to skip those steps…”
Maples: Floodgate Will Never Scale to a Multi-Hundred-Million-Dollar Fund
“No, we'd never be that big. I don't think we'll ever be as big of a fund as like the Series A guys.”
Maples: Number One Reason Floodgate Passes Is Ideas Unworthy of Founders
“The number one reason I pass on companies is I don't think the idea is worthy of the founder's talent.”
Maples: Floodgate Rejects Voting Systems, Requiring Table-Pounding Conviction
“We have a rule at floodgate where there's no voting system. And for a deal to happen, someone has to pound the table.”
Maples: Floodgate's biggest venture wins were not competitive deals when funded
“In our sector of the business, everything is so crazy, early, risky, and maybe even legally ambiguous. It's hard for me to say that, that our very best wins have been hotly contested and competed for, at least at the time we invested.”
Maples: Sitting on 22 boards distracted him from recognizing Pinterest's potential
“When you're on 22 boards, it's blowing up all the time. There's always something totally screwed up. You're not as awake to the possibility of what Pinterest could be when you get pitched by Pinterest, right?”
Maples: Seed funds should assign dedicated partners for follow-on investing
“We had a dedicated partner, Iris Choi, do follow-ons and that's all, and she's accountable for follow-on returns, which more, more seed funds should do.”
Maples: Common versus preferred stock made no financial difference in successful startup investments
“I've never made money or lost money based on common or preferred ever in the ones that worked”
Maples: He made only one investment in 2021, backing Hadrian
“Similarly, in 20, 21, I only made one investment the whole year this company Hadrian. And why is that? Well, I just didn't find any companies that met my criteria.”
Maples: Floodgate returned 300x on Twitter, 205x on Lyft, 94x on Twitch
“Twitter was a little over 300 X and gets all the credit for Lyft, that was like about two, 205 X what else? Applied. Applied is probably encroaching on a hundred X in the first check. Twitch got close, but not quite there. It got to 94 X.”
Maples: Floodgate reserves 30% of capital for follow-on checks
“We settled on 70% up front, 30% in reserves.”
Maples: Floodgate monetized Lyft and Okta holdings prior to 2020 peak
“As much as we loved Lyft and Okta, you know, in those years leading up into twenty-twenty, we're like, okay, we need to monetize these things, right, because there's a lot of excitement about tech stocks right now, and these prices are really high, and it does…”
Maples: VCs' 2021 fund failures stemmed from fast 18-month deployment
“And so, you know, I think that part of why people want mulligans on their twenty-twenty-one funds is they were investing their funds in an eighteen-month cycle. And, you know, what they should have been doing is investing in a five-year cycle because the, ever…”
Floodgate's Initial Zimride Investment Thesis Incorrectly Relied on Facebook Connect
“The thing that we were betting on was the Facebook Connect, to be honest. We thought that that was going to create more trust in this network, even within Zimride. Now, that was the thing that we thought was the real change element. It turns out that wasn't, r…”
Raney: Bridge rounds for struggling startups usually fail
“You know, I would say that I think the way the floodgate describes it is probably accurate most of the time. It's really difficult, I think, for companies to be able to transition through these periods, and if you've gone out and talked to a bunch of investors…”
Maples: Early-Stage Venture Requires Picking; Late-Stage Relies on Firm Branding
“The earlier you invest, the more important picking skills become, right? So if you're If you're investing later stage, branding obviously matters a lot because you're going to have a company that's becoming a more obvious breakout win, and you're going to be c…”
Miura-Ko: Brand is an existence proof, not early-stage thesis
“Brand can be proprietary, but I think it's very hard to assess whether or not you have brand at the very, very early stages where we invest, and so brand is more of an existence proof in my mind rather than something theoretical that you can build over time.”
Miura-Ko: Only 25 IT startups reach $500M+ exits annually
“What we found is that at five hundred million dollars and greater, there is roughly somewhere around 25 companies Plus or minus five to 10 that exit every single year, and those are the companies that really actually move the needle for venture capital.”
Maples: Floodgate passed on early-stage investments in Airbnb and Datadog
“Our biggest failures have been failures of imagination. You know, it's like when I passed on Airbnb, or you know, what, what's another one we passed on, we would have done really well. Data dog.”
Maples: Floodgate performed better with $150M fund than $75M fund
“We were better, we're better at a hundred fifty million than we were at 75.”
Maples: Floodgate will not write seed checks under $500,000
“Probably about as low as I would go as half a million bucks.”
Maples: Floodgate invested in Applied Intuition at a $40M post valuation
“Applied was expensive. It was 40 post.”
Maples: Floodgate funded Lyft at a $5.5M post-money valuation
“Ann funded Lyft at five and a half million post money.”
Maples: Seed venture capital is about micro 'bird spotting' for novel startups
“Yeah, for me, the job is sort of like, you know, when you're in the Galapagos Islands and you spot some, Finch with a weird looking beak that nobody's ever seen before. Like, I think that's kind of what Eric and I try to do, right? We're trying to, but like, i…”
Maples: Floodgate maintains a 70/30 split between upfront checks and reserves
“What we do at Floodgate is seventy-thirty”
Maples: Overboarding limits an investor's ability to learn and stay present
“When you're on too many boards, sometimes you don't learn fast enough. You're not present and mentally awake enough, and you're not incorporating lessons quick enough.”
Miura-Ko: Floodgate's best founders come from existing portfolio referrals
“Our best founders come through recommendations from our existing founders.”
Ann Miura-Ko: Seed investing is about developing insights, not static companies
“At the seed stage, we often say we're not investing in a company because a startup isn't a company. It's a set of insights. It's a development of a set of secrets that you have.”
Miura-Ko ran month-long processes for her recent seed investments
“The last two investments that I've done, I had a month-long process through which we got to know each other, and it was a commitment to one another”
Ann Miura-Ko limits her seed investments to three to six per year
“I only make Somewhere between three and six investments every year.”
Maples: Startups begin dead and require three sequential breakthroughs to succeed
“A startup isn't a company because it starts out dead and has to prove it's alive. And so I like to say there's a sequence of breakthroughs. There's the insight breakthrough, and then there's the value proposition breakthrough, and then the growth breakthrough.”
Maples: VC firms must choose between scale or doing less but better
“And so I think fundamentally in venture, you can do more with scale or you can do less, but better. And you just have to decide.”
Maples: VCs must accept missing deals to focus on essential partnerships
“And I think that the other extreme would be what I call the joy of finding greatness. And in the joy of finding greatness, you say, look, I'm going to be comfortable with the fact that I'm not going to see every great deal. I'm going to be comfortable with the…”
Maples: Most startup insights turn out to be wrong
“Yeah, and I think probably more often than not, an insight will be wrong.”
Gordon: Mike Maples provides game-changing insights in every board meeting
“So I love Mike Maples from Floodgate. He's been, I've been on a couple boards with him. What he does is so well, he has high empathy for CEOs. It seems in every board meeting, he says at least one thing that's game changing.”
Maples: Founders Fail by Rushing Opportunity Selection to Build Product
“A lot of times that the founders, when they're picking their opportunity to go start a company around, they rush the pick and get straight to doing the product, and a lot of founders would be better off if they didn't rush the picking part of it, just like a l…”
Maples: Top Seed Investments Look Irrationally Crazy at the Start
“We've observed that the best companies that we've invested in have been pretty crazy at the time you had to decide, right?”
Maples: 2007 Silicon Valley Founders Couldn't Raise $1M Seed Rounds
“When I would talk to entrepreneurs, they literally couldn't raise a million dollars in Silicon Valley. They could either raise a tiny amount of money from angels and friends and family, or They had to go straight to a five million dollar series a round with a …”
Maples: Floodgate Assigns Individual Checkbooks to Partners at Fund Start
“We start out saying, okay with the beginning of a fund, everybody's going to roughly have a certain size checkbook. And the reason that we do that is we want everyone to understand that when they make an investment, that we all have to be accountable for our d…”
Miura-Ko: Product-market fit requires market demand pulling product from founders
“Product market fit is not just about whether or not it sticks with any kind of market. That market has to be incredibly sizable, and that market also has to have such a powerful need that it literally pulls the product out of the hands and Of the company.”
Miura-Ko: Zimride was extraordinarily capital efficient before competing with Uber
“And in fact, if you look at Zimride, it was an extraordinarily capital efficient business. And in fact, they were extraordinarily capital efficient until they were in competition with a company that had a huge budget to play with, and so it was a matter of sur…”