The Ledger
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Maples: Fund size dictates VC strategy during market crises
“The multi-stage firms, like any firm, your fund size is your strategy. So if there's a crisis, you're going to tend to worry about the companies that move the needle in your large fund. Less so than, oh, I wrote a million dollar check to this company 18 months…”
Maples: US money printing during the COVID crisis was scandalous
“The amount of money that we printed during the COVID crisis is just a scandal.”
Maples: Insight development requires getting out of the present
“If customer development is about getting out of the building, insight development is about getting out of the present, and it's about trying to put yourself into situations where you can live in the future and notice what's missing before other people notice”
Maples: Lyft and Uber could not exist before the iPhone 3GS
“So before the iPhone three GS, you could have had the idea for Lyft and Uber. It wouldn't have mattered because you wouldn't have been able to connect drivers and riders accurately on a map.”
Maples: Rejecting ideas because past attempts failed is terrible VC reasoning
“In fact, that's, I think, one of the least imaginative questions a VC can ask is, like, well, 10 people have tried this, and it hasn't happened, so I don't think it's going to happen.”
Maples: Great startups rely on exponential technology improvement curves
“I generally believe that most great startups are born of these exponential improvement curves that are beneath them. They're like gathering waves in an ocean that you surf back to the beach. And I think it's really hard without a gathering wave to really be gr…”
Maples: Founders without quantifiable technology inflections lack strong core insights
“And so I think if I'm a founder, if I cannot answer clearly what technology inflections are happening that can be calibrated that I'm taking advantage of, I should either evaluate whether my insights powerful enough in the first place, or if I've just thought …”
Maples: Non-consensus success comes from spotting unseen future probabilities
“Being non-consensus and right is not about living in the present and just saying, hey, the world is going right, so I'm going to go left. Being non-consensus and right is discovering something in the future that others don't see yet and making the bet that wha…”
Maples: Momentum-driven VC investors will struggle in shifting markets
“But I think that the people that have played the momentum game are going to struggle.”
Maples: The best long-term venture strategy requires focus
“If they want to be in every part of it, if they want to be in seed, if they want to be in series A in growth, and someday maybe be hedge funds, that's up to them, and I wish them well, but usually I tend to believe that the best long-term strategy is to be mor…”
Maples passed on a $250K seed investment in Airbnb
“Brian Chesky at Airbnb at the time is called Airbed and Breakfast pitched me And I passed, and I had an opportunity to invest 250,000 dollars that would now be worth close to a billion.”
Maples: Scaling acquisition before fixing retention creates more unhappy users
“If you have a customer engagement problem, acquiring more customers is counterproductive because then you just have more unhappy customers.”
Maples: Venture capital has become overly self-promotional with platform noise
“It's gotten a little bit Too self-promotional, I think. So I think that a lot of people now are overly focusing on their personal platforms, and I can understand why some do, but there's an awful lot of noise out there now.”
Maples: Backed Cruise Over Internal Pushback Because Kyle Vogt Made Him Money
“I came in and I said, I want to do this cruise deal. I think that Kyle's really smart. He made me money on Twitch and I, you know, I've decided I want to do it. And a lot of people read me the riot act and said, this is crazy.”
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…”
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: VarageSale failed despite aggressive follow-on funding from Sequoia
“Verage sale. Sequoia aggressively followed and it didn't do well.”
Maples: Roughly 30 great startups will be created every year
“There's so many startups, there will always be 30 or so every year that are great.”
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 funded Lyft at a $5.5M post-money valuation
“Ann funded Lyft at five and a half million post money.”
Maples: Floodgate invested in Applied Intuition at a $40M post valuation
“Applied was expensive. It was 40 post.”
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: Marc Andreessen's advantage came from experiencing the future, not business skill
“Mark's advantage was not born of his experience in business. It was born of his experience with the future.”
Maples: Floodgate 'detaches with love' when losing faith in founders
“I have this saying detach with love. So I'm like, Hey, you know, it seems like I'm not able to help much here. If that changes, let me know, but I'm not gonna, I'm not just gonna sit here and tell you that you're not doing a good job and that we disagree about…”
Maples: Smartest Crypto VCs Focused on Ethereum and Solana Over Bitcoin
“So when I think about the way venture capital has thought about crypto, most of the really smartest people I know have been focused on Ethereum and Solana.”
Maples: Floodgate Invested $750K in Lyft at $5.5M Post-Money
“And invested 750,000 dollars at 5.5 post in Lyft.”
Maples: Tech companies will be valued on fundamentals for 10-15 years
“It may not happen again for another 10, 15 years. The next 1015 years, it's, companies I think are going to be much more valued on fundamentals and what they're really worth, but there are these windows, usually they last about 18 months, where the difference …”
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: Selling Twitter Stock at $1B Valuation Was a Mistake
“And so I sold some of my Twitter stock at a billion dollar valuation. I regret that. I, that was a failure of imagination on my part.”
Maples: Founders in crisis cannot afford to assign blame or hope
“You want to be very sober, very matter of fact, very clear about what the options are. None of this, oh, woe is me. How did this happen? This isn't fair because you don't have the luxury to think those thoughts. You don't have the luxury to worry about who's t…”
Maples: Startups start dead and must focus solely on product-market fit
“Startups start out dead and have to prove they're alive. And they have one job to do, which is get product market fit, And that means answering one very specific question, which is, what can we uniquely do that people are desperate for? And anything that you d…”
Maples: Founder time spent managing corporate treasury subtracts from product-market fit
“Your time is the only thing that's zero sum. And so a decision to become a part-time hedge fund bond expert, it subtracts from your efforts to get product market fit.”
Maples: Startups should split cash across three non-correlated accounts with transfer rails
“Have money in an account that's not correlated to Brex and Mercury in two other places, and have the rails set up between those pools of capital, those deposit accounts, so that you can immediately move from one to the other very quickly. It's the discipline o…”
Maples: Deciding twice as fast lets leaders correct mistakes before competitors act
“Even if my first move is wrong, if I'm moving at twice the rate that you're moving, I can adjust and make my next move before you make your first move. And so, even though I was wrong, I end up being right because I'm getting feedback from your decisions, and …”
Maples: Hiding during a crisis is the worst mistake a leader can make
“The worst thing a leader can do in a crisis is hide. And not having information is not an excuse to hide. So you got to lead from the front and be visible.”
Maples: Effective crisis communications require zero spin and explicitly stating unknowns
“I think you gotta tell people what you know, you tell people what you don't know, and you tell people what you're doing to figure out what you don't know, specifically, and you wanna focus on facts and not happy talk, Zero spin, right?”
Maples: Hard technical startup problems require unambiguous market demand
“It's dumb to solve a hard technical problem that nobody wants if you solve it, right? That's just dumb. You want to solve a technical problem where people will unambiguously, desperately want it if you solve it, but it's hard to solve.”
Maples: AI reduces startup creation effort below Lean Startup levels
“I think if anything, it takes even less to develop an idea using AI than it did with lean startup techniques.”
Maples: Early-stage venture funds benefit from longer capital deployment horizons
“The riskier you are in terms of the stage that you invest, the better it is for you to have a longer time horizon.”
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.”
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: Startups begin when founders bring future insights to the present
“A startup starts when someone living in the future comes back to the present with a new idea, a breakthrough insight, and the market becomes a movement.”
Maples: iPhone 3GS improved smartphone GPS accuracy tenfold
“The technology inflection was the GPS locators in smartphones were 10 times more accurate with the iPhone three GS and beyond.”
Maples: Most startup insights turn out to be wrong
“Yeah, and I think probably more often than not, an insight will be wrong.”
Maples: Startups wildly underestimate how much cash runway they need
“But I think that most startups right now wildly underestimate how much runway they need and have for quite some time.”
Maples: Operator funds are a net positive, not competitors
“I don't look at people like that as a competitor. I look at people like that as a fact, and I just like to embrace the change wherever it's going. And so all things being equal, I'd like to help them and hope they'll make the ecosystem better, and it'll be mor…”