HIRE ADES

“You should be very, very wary of ever swapping out a founder. It's like, I tell people, it's like open heart surgery and 50% of people die. It's a shitty business. Occasionally I've done it for a bunch of reasons, and it's hell on earth. Forget morality. Forget am I a good guy or a bad guy. It's just the most exhausting thing you do. It is easier to just lose money, right? So I hate doing it.”

“What it highlights though is that this purchase is mediated by something else. It's not simply about convenience or ease of use. It's much more about certainty and peace of mind. A, because the dollars are much higher here. Two, it's the opposite of a commodity. Right? You're getting the floors done in your house. Like, you walk on them every day. You care about that.”

“Anduril Lans' $20 billion army contract. First of all, yes, it's obviously a vast contract. But as a reminder, they only have four or five customers. So you better get $20 billion from each of them if you want to be a big company. What it really told me is they succeeded. This isn't as much a new program. This is basically the army saying, look, we got 120 separate contracts with you. We get it. You're now effectively a prime supplier.”

“We actually, by being broad, could invest in liquidity building mechanisms that no narrow vertical ever could. And so because of that, that sort of aggregate sort of leverage, we could bring in more pros, engage more pros, support those pros, retain those pros more effectively than any of the verticalized players. Even though the experience on the front end may have been less customized, the fulfillment capabilities and the marketplace experience was vastly better.”

“Sometimes you'll hear me say a trillion. I just wanna use the t. You know? And from what I understand, like, still less than 10% of it is booked online. It's the same homeowner, it's the same set of thumbs that uses Uber and DoorDash and Airbnb and Amazon. So the laziness and the desire to do things easily and quickly is there, but the purchase is mediated by certainty.”

“I think the challenge for Adobe is, what kills you as a software business, if the work that you're automating gets done in a totally different way. Adobe is the classic creator tool. There is a whole new way to create. By definition, they're playing catch up. So more than most companies, they are under the gun to figure out how to meet their creators in a totally different way. So I think the disruption risk on those guys versus Intuit is a lot higher.”

“What it highlights though is that this purchase is mediated by something else. It's not simply about convenience or ease of use. It's much more about certainty and peace of mind. A, because the dollars are much higher here. Two, it's the opposite of a commodity. Right? You're you're getting the floors done in your house. Like, you walk on them every day. You care about that. Also, it's your house. So if it goes wrong, you gotta live with it, and it may be super expensive.”

“One of the things that this technology is kind of pushing is, like, the rise of generalists at the expense of specialists. And what we see is that the really narrow roles at Thumbtack are under pressure because, like, instead of having that, you know, designer who specializes in that one part of design, it's actually you can just lever Figma make or cloud code to help you do that when you need it every every so often. You know, the hyper specialized engineer, you know, I think that is the the thing that it may change the most where we might have fewer roles that are broader and more general and have fewer kind of specialists.”

“I continue to think that Silicon Valley underrates leadership, and I really care about it. I think leaders have tremendous leverage. ... Leadership to me aspire? Yeah. Well, to, set a set a vision, galvanize people towards that vision, motivate them towards that, provide the courage and moral authority to take risks and sort of venture something. That's all lead. That's the hard part. Like, how do people yeah. Organizing a meeting, like, staffing. Like, you can do that poorly or well, but that's not the hard part.”

“I think the other big thing that we're all gonna be living through is forever in building a technology business, we've been limited by the amount of software that we could create. The rate limiter was writing code, and all the apparatus was to feed that machine as a effectively and efficiently as possible. I think that's going away. Right? Not instantly, but over time, I think It's in the last, like, three months, it seems seems like there's been a huge shift. And, you know, when you kinda play that forward, you get to a world where you become sort of idea, vision, prototype, hypothesis limited.”

“You do not need to be technical to win with AI agents in Q2 of 26. You do not need to be even 1% technical. If in the last three to five years, you have successfully deployed a piece of enterprise software of any sort, you yourself, not some agency you hired, but if you have deployed it, you can deploy any agentic tool, and you can become the hero in your company.”

“I think Travis Uber would be a trillion dollar company today because it would be five years ahead of where it is today. When Travis was CEO, all he wanted to do was get into autonomy. He said from the beginning, our business is dead at its terminal state. No one was going to be driving cars around in Uber. And now they're years and years and years behind where they could have been. He was just too early, and there was toxicity to him, but putting that aside, he was just early for his time.”

“After hiring people who are super talented, who fit with your organization, the last failure mode is that these execs don't appreciate their imperfections and are sort of stubborn or hard headed or defensive about it. And I'll tell you, like, I have hired extremely talented people exclusively, and yet they're all imperfect. And they all have, like, major blind spot. Particularly if you hire very spiky people, they often have deficiencies elsewhere. And that's fine so long as there's self awareness about it. And I care a lot about finding execs who are comfortable in their own skin and get it.”

“Super interesting kind of counterpoint on something. On the one hand, you are extraordinarily aggressive number, a trillion dollars in revenue. On the other hand, stock moved less than 1%. Why? Already priced in. And if you start parsing it out, I think what happened is it's as simple as this. If you look at the forecast, coming in at $215 million in revenue last fiscal year, up from $130 million, I think, the prior year, the forecast is mid $300 million next year.”

“I have given up on an investment thesis I had for 10 years because I was a B2B founder, which is that a smallish TAM is okay with a great founder. I can't do any of those investments anymore. I can't invest in anything that is mid-size or smaller. I just can't. This is the Anduril problem. And this is also why I think a lot of funds are going to have terrible returns. Because a lot of early stage funds are going to swing so hard for the fences that they're going to invest in the number three or the number four and get just zeros after zeros.”

“The answer six months old is I look for folks on my team, I look for what tools they play with. Okay, that was a great answer in like summer of 2025. I tried Lovable last week. Okay, the answer in 2026 is what commercial AI tool have you brought into your organization this month? That's the test. Anyone that is on the bleeding edge that you would want to hire. Now, there are so many great products in the market. Okay, there is no excuse in any role to have not brought one tool a month into your organization.”

“The trillion dollars in spend or 800,000,000,000, however you wanna cut it, is bigger than any other consumer vertical. So you take groceries, it's way bigger than that. You take gas, you take apparel, you take any of these. ... The thing you have to appreciate is our pros have typically not that much of a cost of goods sold. It's really just their time.”

“The trades and things that interface with the real world, in particular, in ways that are hard to automate, are very durable. OpenAI put out a paper, I think, with ChatGPT-4 that came out about sort of the jobs most at risk and least at risk. And the least at risk was, like, filled with home service jobs. It was, like, oil and gas jobs and, thumbtack jobs, like, things that you gotta be there.”

“Wall Street is simple. If you give them growth, they'll leave you alone. If you don't give them growth, you better give them profitability. If you don't give them either, they're going to bust your chops. That's reallocating dollars from humans to compute. That's not what's going on at Block because they're not investing massively in CapEx, but that is 100% what's going on at Meta because the free cash flow, when you honestly account for the CapEx, is almost zero. And that depreciation is going to start hitting and they're going to be firing people because they need to give it to Jensen. And today, compute eats jobs.”

“Well, I think the magic is that the AI can do the digital interface for these folks in a in a much better way than they've ever done for themselves. Have your website and your social media presences up to date, respond to people quickly, answer questions, submit follow ups, submit estimates. Basically, the, like, admin work that's involved, which is rarely why these people got into the business.”

“The trades and things that interface with the real world, in particular, in ways that are hard to automate, are very durable. OpenAI put out a paper, I think, with Chet g b t four that came out about sort of the jobs most at risk and least at risk. And the least at risk was, like, filled with home service jobs. It was, like, oil and gas jobs and, thumbtack jobs, like, things that you gotta be there.”

“And I think one of the the just superpowers of this technology is how fast it lets you move, particularly when you lower the group size that's required to get anything done. You know? To the extreme of just one person, that's the fastest. But even taking a product team, like, at Thumbtack, historically, our pods were, like, 10 to 14 people. Now they can be, like, three to six, three to eight. I think that alone makes us faster.”