I learned the hard lesson that whoever pays you kind of owns you and determines how your product evolves, which led to a misalignment with my original mission of helping students find good jobs.

Don't customize legal documents unnecessarily; instead, get quotes and specifications before spending money on legal services.

Founders frequently waste money on hiring, especially when they pursue high-salary candidates from large companies, believing they will significantly boost productivity.

I initially hesitated to hire others for my company, fearing they would disrupt my vision, but once I did, I realized it was a mistake to wait so long.

I made mistakes in the fundraising process, including not meeting enough investors and assuming a deal was done before it actually was.

I made many mistakes at Watsi, but I was careful to hire people who are much smarter and better than I am.

Hiring the right people is incredibly challenging, and it's okay to make mistakes in the process. I had to let go of a salesperson early on because he wasn't a culture fit, which was a learning experience for us.

Initially, we hired too slowly, which contributed to our rapid growth from $0 to $100 million ARR in just a year and a half.

I believe that the best decisions in business often happen for the wrong reasons, as was the case with my decision to attend law school.