“The best thing I did at EchoSign was spend 20% of my time recruiting once we had product-market fit, because one truly great VP or leader is worth fifty pretty good hires.”

“I hire people who can do the job today and grow into three more jobs tomorrow, because at Dell we doubled every couple of years and the people who looked right on paper were often out of their league inside eighteen months. The best teams I have built share one thing: everyone acts like an owner, not because we give them equity, but because we connect their work to the customer and the numbers everyone can see.”

“I used to think I had to close every deal and write every piece of content myself. Now I run three businesses without being the CEO of any, and the team grew while I took 13 weeks off to write a book.”

“I spent my first 15 years as CEO driving results out of people, and the best ones kept leaving or checking out. The shift came when I stopped asking what I could get from the team and started asking what I could grow in each person. Now I hire for values first, skills second, and build the team around a mission they can see themselves in.”

“I spend about two-thirds of my time reviewing the actual work and jamming with the teams doing it, because the bar for what we ship is what defines the team. At Brex 3.0, the people who stayed were the ones who believed intensity, in-person craft, and ownership of the work mattered more than title or process; everyone else self-selected out, and that was the point.”

“I built my first company at 19 and sold it at 36 for $17M, and the only reason that happened was because I stopped trying to build a crew and started building leaders. Most owners hire hands. I hire people I can turn into the next version of me, then I care about their home life more than they do, because a broken man brings broken energy into the shop.”

“I hire people who are better than me at their thing, then get out of their way. At Mercury, our first recruiter became our VP of People, and that single hire changed how we scaled culture and talent together. The CEO’s job is not to be the smartest person in the room; it’s to keep raising the average.”

“I used to think a great team meant hiring the smartest people in the room, but after building AngelList and watching Naval build AirChat, I realized I was half right. What actually scales is agency: people who spot problems you haven't seen yet and solve them without needing a meeting.”

“I scaled Endurance from four people to fifty-plus and from 12,000 customers to 1.5 million, and the only thing that made that kind of growth repeatable was trust: hiring people I could disagree with loudly and still leave the room aligned.”