The Ledger, every show

“Yeah, the best investors benchmark and recent, they will invest less than their supposed minimums for the right company.”

“We had offers, actually, we had 22 offers at a billion dollars. We turned them down and took 350.”

“The one thing that really kills me is when I see a founder playing the victim here and say, well, my investors didn't help me enough. Like, That's not their job. Their job is to give you money and hopefully do no harm.”

“Adobe you know, has a product that, you know, has been evolved through acquisitions, which turns what they're offering into what our customers tend to describe as a Franken-sweet. It's a bunch of products that don't really integrate well with one another.”

“Things that work tend to work really fast. You know, it was kind of this anti-pattern. Most people would say, well, you got to stick it out and be perseverance and, you know, keep, you know, banging your head against an idea and you have to keep executing it. …”

“First time founders brag about how many employees they have, second time founders brag about how few employees they have.”

“I would say when you feel market pull, when you feel the market, like I gave the example of Starbucks, you know, they're going past all of the processes, they're going past all, like they're seeking forgiveness, not permission to use your product. You're seein…”

“One thing I'll say about titles that I unequivocally believe is that if this is a something that a candidate brings up early or even during the interview process at all, it is a pretty red flag. It shows you kind of what their values are. The best people I've …”

“We hired somebody, a great software engineer. We thought, wow, actually the market is showing that this person should be 30 K more than the other folks on the team. And so not only did we hire her at that price, but we also raised everyone else's salaries to m…”

“In our series A, we're way oversubscribed. We actually have, we raised our series A over a year ago and we haven't even started spending it. So we had far more investors who wanted to invest than we had you know, capital to sell them. And so I gave our employe…”

“With 20 people today, I feel like we're having a greater impact and ship faster than we ever could with a 120 people and software engineers at Optimizely.”

“So instead of answering the question how much you're raising, The best answer is, you know, we don't need to raise, so we don't have a budget we're driving. We want to sell no more than this percentage of the company, and we're letting the market decide the va…”

“I think the best investor you can have for your company is somebody who's on the rising arc of their career. You want a Peter Fenton when he's 35, not 45. You want, not, not going to be ageist, but you want somebody before they've had their first IPO, and you …”

“One of the benefits side, unintended side benefits of the round we raised I do think kind of made everyone else's job. Who's a founder trying to compete with us much, much harder because first of all, we had hundreds of investors.”

“If you're a founder listening to this and you're contemplating an up round with a liquidation preference more than one or a down round, do 100% of the time do the down round.”

“You know, like that's what you're looking for is this founder market fit around the problem, not somebody who's like a McKinsey consultant who said like, if their first slide is here's the market map and here's the market size and, you know, here's the niche w…”

“We raised it a three hundred fifty million dollar valuation with 700 K and ARR.”

“We're a team of 20 at Rewind, and we're more productive. We ship faster than we ever did when I had a team of 400 at my last company.”

“Today we have 20 people and rewind we had 450 and I feel like with 20 people we're able to do more and execute faster and be More tightly aligned than and ship than we ever did at Optimizely.”

“I see a lot of companies today that are ex Apple people who've built amazing things and they go off and they spend years and years toiling away and never really ship anything. And, you know, I think they have this sense of like, it needs to be As good as the l…”

“There's whole categories of companies that are going to be cat, you know, Category defining independent successful big public multi-billion dollar companies that are just applications of large language models in a specific domain for a specific user with a gre…”

“I think a lot of jobs will be gone in 10 years, but they'll likely be replaced with new ones. I think that's probably an obvious Conclusion. I think on the order of probably 50% of work will go away. It would be fundamentally changed.”

“Eventually, you know, I don't think it will necessarily replace engineers, but it'll certainly augment them. You'll have plenty of, you know, half the work that an engineering team does will be done by AGI, and half will be done by humans, and the human stuff …”

“That's why I announced and shared our investor deck unredacted. I didn't hide any numbers. You know, you can find it on Twitter, you know, seven minute pitch you know, millions of people have seen it.”

“Today, the best products are bought. They're not sold. People come to Optimizely, and they try our product, and they convince themselves of the product before they even talk to a salesperson on our team”

“Every meeting at Optimizely, the notes from that meeting, including the board meeting we had last week, get sent to the entire company.”

“Always saying the highest price is almost certainly going to be a mistake.”

“I have 10 years I put into my last company and I can recognize that really Only three or four things that we did made the difference in the success or failure of the company.”

“Many, many examples of this, you know, from moving to the enterprise too quickly, to sort of not recognizing the core of what we had, to sort of abandoning The core problem of solving churn”

“To be a founding engineer is so much more meaningful to somebody, both in terms of their, you know, if, for example, if 80% of your friends are founders of companies and you are just a software engineer, but you started in your first employee, like that just p…”

“You can still pay, you know, 75th percentile in, in terms of cash, and it shouldn't be a huge lifestyle change just because they're joining a startup. I think that's a, you know, 10 years ago, that was this idea that you're exchanging, you know, risk for rewar…”

“Like we don't hire people straight out of college. We hire people with experience.”

“I think it's fair to give on valuation.”

“I've been lucky not to have a board for Limitless.”

“I do think boards as a company gets bigger and bigger and closer to going public are really important for governance and accountability. But when the company is so early on, it's very, very hard for a board member to get up to speed. You know, they're showing …”

“The investor who's giving you that term sheet wants to preempt it. They want to get in early. They want to get a better price, and so they know that if they do it before you're getting information from everyone else, that's going to help them.”

“You as the founder of the company are actually As a fiduciary responsible to represent the interests of the common stock and that's your employees, you know, and so if you want to do best for your employees, you want to rationally control as much as you possib…”

“Google's notorious for building products that are technology in search of problems. Google Wave, Google Buzz, Google Glass, like, all of these products were basically some smart engineer or technologist starting the sentence with, Wouldn't it be cool if, dot, …”

“We're building a hardware, we're building a wearable, If I can solve the same problems I want to solve without them, all for it. I'd be happy to do that. Hardware is hard. It's expensive. It's painful. I would happily give up hardware if I could solve the prob…”

“In some ways, actually, you kind of want to choose founders who are excited about smaller problems, because it tells you that they're not just falling in love with what they saw on Twitter or social media, that there's actually something they care about.”

“I've cut out basically most of my, I don't spend much time with friends. I have basically no hobbies. You know, I, I'm reminded of this Rick Rubin quote. He's like, I have no technical skills. It's like that, but for my life, like all I do is spend time with m…”

“Doomers plus regulatory capture, I could see creating a world in which a lot of AI innovation is, is stalled.”

“We got well over you know, we got millions of views over a thousand offers to invest, many from really great investors, and I spent the next week in meetings with folks.”

“And I think that's really the value of being more public in your fundraise, It helps you cast a wider net, which then you ultimately find the perfect match, the perfect marriage, and you end up, I think really getting a sense for your market prices. That's the…”

“You know, it's true that since we did raise in public and we were successful, we've had some imitators and some copycats, but none of them really have affected us. You know, it was a little bit of like, oh, should I have Been so public about our success when I…”

“We had 20 offers at a billion dollars or more but 20 out of a thousand is pretty small.”

“They can convince themselves that they're actually meaningfully moving toward product market fit by just sitting in the room and coding all day. Most of the time, that time is wasted. You know, it's not getting you any closer to the insights you need to buildi…”

“Yeah, and that's why we have six years of runway, and I hope to increase that, not decrease that over time, is I've learned that mistake, and, you know, it's great to raise money when you can.”