The Ledger, every show

“Second, they are way better at negotiating than you. So, any time dealing with a superior negotiator, the only thing you can do to try and even the scales is move the negotiation async. So founders repeat after me. I'm talking to you directly now. You will say…”

“In those cases, I only would want to bring on an architect if they'd been an architect before. If they'd only been an optimizer, they are going to fail because they've never written playbook from scratch.”

“The more success a founder has with a given startup, the more that business ascends and grows in revenue and valuation, that actually the less control that founder ends up having or the founders end up having of their own business, because most startups that t…”

“Too often, most of those investors seem to only have one lever to pull when they're confused by the gap between the investor memo they once wrote and the actual performance on the ground. And that lever is Oh, let, let's replace the CEO. And I'm being callous …”

“Venture board members are normally distributed. The large group of them are in the middle. And they're fine. They have little to no operating experience. And they provide value in four ways. They make introductions. They write checks. They provide some strateg…”

“The reason founders were getting fired is because no one was investing in the latter. And venture investors don't bother investing in it. They just don't bother because they make their money off the next wager, not the career development of a CEO. It's not tha…”

“At any given time, we think that a startup is working backwards from one of three things, very simply. I'm either working backwards from M&A. I'm working backwards from profitability. I'm working backwards from the next fundraise. You got to choose one.”

“It's not manager mode is bad. It's the greatest CEOs know when to calibrate which one is needed.”

“Most CEOs are really bad at planning, and that's because there's this little known secret in the Bay Area. Most CEOs never run a business before.”

“You don't sell to a company. Magic box is about finding the person. You're finding the champion on the other side. The person who has motivated for their own reasons, career, money, reputation, what have you, they see the fantasy, they fall in love.”

“And in magic box, founders are eager to do the same thing, thinking that competition will improve their deal size. When in fact, I think more often than not, that is a negative signal until the very end of the dance.”

“Start with the job description. It's a fucking mistake. Start with, it's 12 months later. You've hired the person they started today, 12 months have gone by, you're clinking champagne because of how great it's been. What's changed about the business? What does…”

“Intuition comes from, in my point of view, A deep understanding of self and the capacity to get quiet and be well resourced. Meaning you've slept well and you've eaten well and you have enough love in your world. And I think what founder mode can confuse is my…”

“Founding a company is about courage and character. Like, I'm gonna just go take a shot at this. Running a company is about a set of skills. The job just changes the moment the thing you've birthed into the world starts to have some success. Your job goes from …”

“Our incentives aren't fully aligned. Yours are to common shareholders. Mine are to preferred. Mine are to my LPs and my partners. You, yours are to yourself and to your customers”

“That was the first time an entire generation of founders heard, you might not raise more capital. You better go learn this crazy idea of how to have more cash coming to your business each month than go out. I imagine you were on the receiving end of a few of t…”

“I think that is largely gone from startup life, and that there are therapists everywhere amongst the My Founder community. There are coaches everywhere And I think, by the way, they are normally distributed like the same group I described earlier, and there ar…”

“I am an enormous believer in founder driven sales at the beginning, especially for anything that's B to B. I'm an enormous believer in making sure that you have this point of view of a problem in the world, that you validate that the problem's real, that the p…”

“And what it led me to realize is that every well-run company has a rhythm. It's unmistakable. You can't miss it. You can't not see it. You just spend a couple of days, like through a spy cam watching a business, you'll see the pattern.”

“First question was, well, describe to me your ideal founder. What's a great founder? And the answers universally were the same. Investors would use words that meant grit and tenacity and courage and insight. And I'd say, great. Question number two. Describe to…”

“We like to joke that more companies die from suicide than homicide. And it's grim, but also if the two or three people in charge of the business can't get along, nothing else matters. It's all gonna break apart.”

“I think ready, fire, aim is the most common that we've seen.”

“At any given time, Lenny, companies are working backwards from one of four things, whether they like it or not. I am working backwards from an exit. I'm working backwards from my next fundraise, working backwards from profitability, or I'm working backwards fr…”

“In enterprise sales where I'm pushing, in magic box, I'm always trying to entice. I'm never, ever trying to push.”

“If you do live brainstorming you have diminished all the folks that prefer to sit and chew on something first.”

“Where the founders often get hung up on for us is that they've moved towards selling without contemplating ideal customer profile, without contemplating qualifications, without contemplating discovery questions to get to that, and most importantly, kill criter…”

“Founders often make the mistake when planning for the year ahead of, I need to be at this revenue to justify this multiple. And then all of the funnel math is a plug. And that's just, that's death. As opposed to here's what's been true for the last three month…”

“He did the unthinkable and left tenure, while at the same time was playing in bigger and bigger neighborhood poker games, such that he earned enough money just from poker to play for my, pay for my undergraduate degree.”