“I used to think hiring a leader meant I could finally stop being in the details, but at Sundial my team told me we were too hands-off, and that was a hard pill to swallow. Now I hire leaders not to replace my judgment, but to extend it: when a function's success depends on context I don't have time to absorb, or when my staying involved is blocking faster decisions.”
“You hire a leader the day a function becomes a bottleneck you cannot personally unblock anymore, not when you are simply tired of it. At EchoSign I stayed the primary closer until the pipeline was growing faster than my calendar, then I brought in someone who could run the playbook better than me.”
“I hired a full-time office manager at employee 7 because it felt like what a real company should do, and it cost us $85K and three months of product velocity for work that did not need a full-time hire.”
“I hire leaders when the work is steady, predictable, and genuinely 30+ hours a week. Before that, I outsource it. I learned this the hard way at my first company when I hired an office manager/HR person at employee 7 and ended up inventing work for them while product velocity slipped.”
“I hire leaders when the function starts eating the one thing I cannot replace: my own clarity of belief. When I was at Quokka Sports writing the S-1, I learned fast that no founder can carry product, story, and every operating function at once without the category going fuzzy.”
“The moment you can afford a specialist who is better than you at a function, hire them and design your own role around your actual superpower. I coach founders to stop being the permanent generalist and instead become the athlete who builds a team around one exceptional thing.”
“I stayed solo too long at MarketBeat, and it capped us around $2 million with one part-time employee. Once I finally hired leaders for marketing, sales, fulfillment, and finance, revenue per email doubled and I could actually think again.”
“I learned this the hard way building Method: I held onto functions I was only average at because letting go felt like losing control, and it cost us speed. The signal for me now is when I'm the bottleneck on decisions or doing work that someone else could do excellently. The founders I back most are the ones who hire people smarter than them in a function early, even when it stings.”
“I hired leaders when the function was becoming a bottleneck and I could no longer be the best person doing the work. At Gladly and Vontu, the moment I was spending more time managing a growing team than improving the product, I knew I needed someone who could run that function better than I could.”