venture capital

“I think people who are in tech, especially are certain bubbles of tech. That's the default. It's like the first thing I do, I have an idea now let's go raise money.”

“You can always raise venture later. Like it's a one way door. So I kind of want to delay that door, you know, for whatever I build next if I can.”

“This is why I actually think this is a better path than what used to happen, which is all the great operators turned into VCs, but to capitalists, right? And there you're like pretty disconnected from the ops. I think this advisory type path, I'll leave the cr…”

“It's definitely not a comp thing. I'll say that I think It could be a stability of life thing. Search is incredibly volatile and have to hustle so hard.”

“100% of VC is a salesperson. Cause they're selling LPs to give them money and they're selling CEOs to take their money in exchange for equity. Like that's the job of a VC. All the analytics, all the data and the, this and the, that, those are just like updatin…”

“The basic idea is bootstrapping is for lifestyle businesses that want to cash flow. Funding is for companies trying to create a billion dollars in annual revenue.”

“50% of portfolios don't return, investments don't return anything.”

“They have a horrible track record when it comes to funding people of color, women, people who are non cisgender, white male, just kind of the track record.”

“I think that structure, it looks a lot like the structure we use in a VC pitch or an investor pitch, because we're talking about much longer timelines and we can say, look, the world is really changing and 10 years from now, there's going to be chaos and destr…”

“The majority of companies on this planet run like ours. They're bootstrapped. They don't have any money. No one's willing to give them a penny. And they open up a shop somewhere, they do something, they put their shingle out, and they, you know, launch a websi…”

“Basically almost nobody makes it that way. Like really almost nobody really makes it that way. And there's a lot more room to make it and to build a successful business if you throw out that outlier and look at all the other places you can land as a business.”

“You know, this idea that if you just have the right benchmarks, like DCs won't judge you for spending too much in engineering, but it doesn't actually help you get to the right place. It just helps you get your board to be less angry at you.”

“And you know you've crossed the chasm when you say, I don't have to raise any more venture capital.”

“The only reason you need venture capital is if the, well, two things. Either, A, the technology is too expensive and you cannot self-fund it. GPUs, a bunch of that, training large language modules, those kind of things. Or This thing is going to get catch fire…”

“A venture capitalist gives you money and what they're buying from you with this money is I want you to use this money to change the state of your company. Such that when we raise the next round, the next investor will value your company two to three times high…”

“Another related terrible piece of advice VCs give you is switch to annual contracts. This is terrible advice. Terrible advice, Lenny. Terrible advice from people who have never built products and aren't in the field. Going to annual contracts on a spreadsheet …”

“I think Carta said that 13 something percent of founders last year were women. It's declining year over year. FEMA-led founded teams were at least two percent of venture capital. Women hold 30% of senior leadership roles. Women are 30% of software engineering …”

“I had VCs tell me don't get pregnant when I was like, these things happened and yet like here I am and it's fine.”

“There is no such thing as a long feedback loop. You can make a decision about how long the feedback loop is. That is your choice to live in a long feedback loop. And you can choose to shorten the feedback loop. And the way you choose to shorten the feedback lo…”

“There is a conventional wisdom in the venture capital industry which he defies almost completely. You know, he makes a lot of little bets, not a few big bets. He is he runs a very lean operation. He doesn't have a lot of partners. He doesn't have actually any …”

“In France, I think like the business model, like has to be like front and center, perhaps for each, like Be able to raise venture capital for each, be able to like even exist. Right. So it means like it attracts a lot of like business you know, minded you know…”

“If you're wanting to just tinker and solve a problem that you think is not going to be hyper competitive. So for example, that form filling thing or software that just does a narrow thing that doesn't require 20, 30, forty million dollars to be lit on fire bef…”

“I feel like if you're building something that has the potential to be viral or to target the masses, and so it doesn't really matter if you're like funded or not, you just like build a great product that people will share. If you're able to do that and you're …”

“And one of the things we emphasize inside the firm is to look like we're investing in strength. Not lack of weakness. Like, I want to know, like, how good, like, are they world-class? Do they have a world-class strength? And, you know, can that beat anybody? A…”

“There's this running statement where a lot of VCs will say, don't go after tier one logos, go learn down market or go learn from like logos that don't necessarily carry a lot of weight. The ones that carry all the weight are the ones that are willing to take a…”

“Within reason, always offer to pay. Now, you should be turned down, right? If you go out with a VC, right, and you're like, you know, you put a card down, 99% of the time, they'll be like, I got this, like, please, like, this is, don't worry about it, right?”

“Like I use this prism as an investor, which is when I make a seed investment or shares a investment, let's say I want half of my friends who are VCs to laugh at me, like literally laugh. Cause I know most of the people I compete with pretty well. And so I'm ru…”

“Enterprise software sales cycle is like, 18 months if you're lucky. You know, this is always a problem. The enterprise sales cycle is shorter than the venture backed startup funding cycle. Longer, longer, rather longer. Like it takes you longer to get an enter…”

“Well that doesn't work from a venture perspective. Like with those kinds of, you'd never get the venture returns. You can't invest in things. When the valuations are already nine digits or 10 digits, and you think you're gonna, a small portfolio that's got lik…”