The Ledger
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Raising larger rounds never allows startups to skip future fundraising rounds
“No one ever skips around. You spend the money and you're back out in market on the exact same schedule you were if you raised Half as much money.”
Preemptive round markups rarely reflect actual commercial progress
“When you think about these like preemptive rounds where it's like, oh, some company raises at five hundred million in January, and then in March, they raise at a billion. It's like, it's unlikely in most of those cases that you actually engage in any commercia…”
Capital cannot overcome limits on engineering hiring velocity
“More capital isn't necessarily going to make you move faster. There's a physical limit to how many talented engineers you can hire. In a six to eight month window.”
Raising at nosebleed valuations eliminates startup exit optionality
“And if you raise a nosebleed valuations and you ingest boatloads of capital, all of your optionality goes out the window in terms of successful exit.”
Scaling a startup gets easier as direct reports become senior executives
“Liz, it actually does get easier. Trust me. Like it does get easier because as you A bunch of things happen that make it easier. One, you understand your customer better. You understand your own business better. You understand the economic model better. In thi…”
Denehy: Evaluating product-market fit based solely on revenue is lazy
“Revenue as a marker for product market fit on its own is probably a lazy way to look at it.”
Denehy: Pre-product market fit is about solution design, not custom engineering
“So when you're pre-product market fit, you generally don't get bonus points for building things from scratch. So really that Pre-product market fit stage has more to do with solution design than it does with engineering, or at least it should.”
Denehy: Zero technical debt means an engineering team lacks leverage
“I think most good engineering teams sort of look at technical debt like a credit card, right? You know, a balance of zero means you're probably not leveraging it enough. And if you owe Amex a 150,000 dollars, that's probably not good either.”
Denehy: Startups must prioritize commercial activity over perpetual research
“At the end of the day, you have to build a business, not a university research project. So there's a point at which you need to get the show on the road and engage in meaningful commercial activity.”
Denehy: The size of a VC's support team reveals their true value
“At the seed stage, VCs always say they add value beyond cash, but If you actually do the best way, and at the seed stage, you need all the help you can get. So you really want a VC that's going to be able to step up and support you. Well, the best way to kind …”
Denehy: Growth-stage startups need VCs with prior founder experience
“I think as you get to later, later stages, you know, your A or B and beyond, it's really important that some of the big money earlier on is coming from investors who were at one point entrepreneurs in their own right that had real companies”
Bad executives can be fired, but bad 10% investors cannot
“Because if I hire an executive and they don't work out, I can fire them. But if I bring on an investor and they suck, you can't really like fire someone who owns 10% of your company.”
Growth startups can fail on experiments if core targets are met
“As long as the stuff in that experimental bucket doesn't drag down or otherwise negatively impact the OKRs of the business that we're aiming for next year, do what you want. Like, obviously, we want those things to work, but, like, it's okay to fail in that re…”
Denehy: Enduring SaaS startups require need-to-have products, not sales tactics
“The solution you're delivering has to be a need to have, not a nice to have, full stop. You know, if your business is just clever marketing, or it's just jamming something down a customer's throat with an inside sales You're going to struggle to build a really…”
Denehy: A startup is not over until the last dollar is spent
“Until the last dollar is spent, it's not over.”
Denehy: Leadership strength and vulnerability are self-reinforcing
“The two actually really, I think, are self-reinforcing. Like, you as a leader have to exhibit a lot of strength in order to sort of have the courage to just own up to things, whether you're stressed or just being honest about things not going well. So a lot of…”
Denehy: Early-stage CEOs face severe context switching as player-coaches
“The early days, like the sort of one to 30 or 40 years Employees and the, you know, zero to one to two million as a CEO, you're a player coach. So you're doing a lot of jobs as an IC, but you're also managing maybe some frontline folks and you have CEO stuff t…”
Denehy: Scaling past $10M revenue requires processes and experienced leadership
“Your first five to ten million in revenue can come from a lot of individual heroics, but beyond that, you need really scalable processes and teams with bench depth and predictability with respect to the outcomes they're driving, and so you'll never get there i…”
Denehy: VP hiring takes up to six months, requiring early recruiting
“And this is something even, even with electric, I completely underestimated in our early days and didn't get right, but it's going to take three to six months to hire a VP level or above person. Sometimes you'll get lucky, you'll hire him faster, but for the m…”
Denehy: Founders must start executive hiring before fundraising rounds
“You've got to start ahead of the fundraise and ahead of that next inflection point, because you're going to find yourself having been caught flat footed and needing to execute on a plan that you just simply don't have the People and leadership to do.”