The Ledger, every show

“Spending time with associates. I think that's Tends to be a waste of time. And I think meeting with investors to give them updates, I think that is also a waste of time.”

“Our base case, if none of our bets work out, we think we'll be around six hundred million in ARR, growing 50 to 70% year over year as a software business. If some of our more financial products that we're working on hit, We have a broad spectrum. These are hig…”

“I actually challenge the notion that VCs have to have such a high failure rate. I think Part of the reason there is such a high failure rate is because everyone's swinging for home runs. No one's, no one, there are very few VCs that feel like they can assemble…”

“I think there's like two types of startups. There's innovation startups and execution startups. So an execution startup is like a rippling or a MongoDB, where it's just like, if you build a better database or a better HRIS system, you have line of sight to bil…”

“One of the biggest mistakes that startups and CEOs when they launch new products make is they have such a great sales motion. They can push a product out to market that doesn't have a strong product market fit, but it feels like it does initially. And then it'…”

“What I tell the team about how to build AI products is you got to follow two rules. One is differentiated customer experience that we couldn't do before AI existed. Like you do something for the customer that literally we could not have done a year ago. Just, …”

“I think the biggest feature of AI is not that it's smart it's that it's debuggable.”

“Companies scale non-linearly, but people scale linearly. And that's why executive half-life is so short.”

“But in these mission oriented and vision oriented companies, The founder is the keeper of the mission, and so you can build all these functional pieces around the founder, but the one thing that's very hard to replace is the keeper of the vision, and so it's s…”

“People looked at it as a, this is a small market, so it must be uninteresting. And what we looked at it is because of the network effect of this market, this is an end of one market. There will be one and only one platform for this.”

“When we look at markets to go after, we really have three requirements. One is this has to be an end of one market. We won't enter a market that we think can be fractured where we would face competition to, we have to have some innovation on the business model…”

“If you believe in the network effects of our business, it's a much more powerful paradigm to execute on multiple fronts of this network because the network converges faster.”

“Product and technology advantage is short lived. Your product decays, new entrants want to come in with a better, smarter version, all of those things. And so what keeps the best companies growing bigger and bigger is not product development, but owning the li…”

“We'll buy as many services firms as we can that we can turn into software businesses.”

“Payroll is a debt product. With bi-monthly coupons, equity is a capital product, and in any economy, whether it's GDP for the nation or the Silicon Valley economy, any economy that's growing, by definition, equity accumulates exponentially, but debt accumulate…”

“Fundraising in private markets and venture is an auction process. And so aggregating the auction into a short period of time is part of the strategy because you want to create an auction. You want to create competition. You don't want to drag this out and do t…”

“Founders are afraid to ask investors to do work. I think that because they'll turn them off, I would use that actually as a great litmus test to turn them off, because if they don't want to do any work to earn the right to invest, they're not a good investor.”

“Sometimes you just have to let things burn, and it was super powerful for me, because it left me off the hook of, I have to fix everything today, that I can let things burn, and understand that there's always going to be forest fires, and being patient, and ha…”

“At the seed round, investors aren't necessarily looking for what's a great idea. What they're looking for is what a Series A investor will think is a great idea.”

“We're very much a, let's win in small markets, and then concentrically grow out of that, rather than try to take on a huge market all at once.”

“I think a lot of venture is momentum investing.”

“I think one of the big problems structurally in the capital markets world today is we have an environment of hyper liquidity in the public universe, and then zero liquidity in the private. And there's literally nothing in between right now.”

“I think when we look 20 years ahead our vision for the world is that the great enduring companies will actually be privately held and they will find liquidity in private markets rather than public markets.”

“If you can build a software company selling to startups you can build a software company selling to anybody.”

“My expectation, my hope is in three to five years, how Carta is sort of synonymous with infrastructure for venture in three to five years, it'll be synonymous with infrastructure for PE.”

“What makes venture unique as an asset class for us is that it has what I'll call a global topology. You know, you bring a company on to Carta because all the investors are minority holders. They bring a bunch of investors. They bring 20 investors. And then tho…”

“So we finance crypto companies today no differently than we finance the railroads.”

“And that's been true of me is that I've been wrong more than I've been right. My superpower is I'm very quick to realize it and fix the mistake. So the damage is, I do a good job of damage control on my mistake, but when I am right, I may not have a high batti…”

“We're now tying board members to companies, so this is a strong link between venture funds into the companies, and it's the type of product that, because it focuses on that link, it becomes a non-linear growth pattern, as opposed to, for example, four nine A, …”

“So that today our four nine a business runs at over 70% margins.”

“At Carta, the way we think about R and D and businesses, we decouple those two discussions. Many businesses will say, Hey, we want to launch a new product to market. You know, what can we charge for it? What's the profitability of this product, et cetera. And …”

“There was sort of this kind of, I think pessimism or even a little bit of distrust where this idea seems so obvious to people that because it didn't exist, there must be something wrong with this idea that they didn't know. And so, it actually, you would think…”

“Almost all VCs will tell you they will take on execution risk. They'll even take on team risk. But they'll never take market risk, because that's the one thing they can't do anything about, which is why VCs tend to look for really big markets.”

“The time it takes to build a company these days at the scale that venture and our investors would like us to build companies at just takes longer and longer. It's harder the journey's longer, and it's much more expensive. So I think, and I think that trend's g…”

“I think one of the reasons that private companies work well and are working better and better is that the alignment of management and investors is more highly aligned in the private world than they are in the public world.”

“One of the reasons that I think cost of capital for startups is so high is because there's lack of regulation.”

“You can tie almost any regular regulation in the public market model to somebody got defrauded. And so we put in this rule to make that happen. And it's a patchwork of rules that holistically don't make a ton of sense.”

“I think the talent war at Silicon Valley would be one with Better equity comp than salary comp.”

“We're on the second half of an S-curve in venture, but the beginning of an S-curve in private equity and private credit. And that's driving a lot of the, I think the next two to five years of growth.”

“If we get to a billion bucks, I think it's cause we caught fire in private equity. If we get to two to three billion bucks, it means we've gotten into other asset classes.”

“I think when we get into trouble or most companies get in trouble is when they focus on the outputs, they're looking, they're trying to strive the numbers that, Are really outputs of something else. and what happens is they lose sight of what that something e…”

“Alpha is what we consider things that we have control over, and beta is things that we don't. So beta is like market. You know, if we lose a customer because they're going out of business or, you know, the market's down, that's beta. You know, it affects our o…”

“I think product portfolio management in companies is much like Venture Live.”

“And that's always been our thesis is start in small markets, win something that nobody else cares about, and then concentrically grow.”

“Venture is very volatile as an asset class because it's the tail end of the whip. It's the last asset class allocators allocate to. So they start with bonds, then they go to public equities, then they'll go to real estate, you know, then they'll go to credit, …”

“We'll probably do two or three deals this year, another two or three next year.”

“When you get to this stage, what you realize is your job is still to build products and sell them. That, that is the most important thing you do. But your job is also to build a company that can do it for you. And that's actually really hard. It's hard enough …”

“So now we have agents all night going through testing all the different possible things that a customer might do the next morning when they wake up, and then we catch the errors before they do.”