Despite immense success with his wife Cass, founder Mike Lazaro calls his next venture—started without her—the 'biggest mistake of my life.' He admits ego and hubris led him to ignore her doubts and partner with someone else, resulting in failure. The lesson: past success doesn't invalidate a trusted partner's intuition.

When Ryan Smith complained about a better-funded competitor, his father slammed the table and asked, "Who's stopping you?" This single question instantly shifted Smith's mindset from blaming external factors to taking radical ownership of the company's destiny.

Taking a small amount of money off the table via a secondary sale de-risks a founder's personal finances. This financial security empowers them to reject large acquisition offers and pursue a long-term, independent vision without the pressure of life-changing personal wealth decisions.

Ryan Smith credits Qualtrics' success to his co-founder brother. Their sibling bond allowed for brutally honest debates that would break a typical executive team. This ability to "go 15 rounds" without lasting drama enabled better, harder-fought decisions.

When a founder faces a major acquisition offer, the pivotal question isn't just about valuation, but temperament. A board member should ask, "Are you built to be a public company CEO?" The intense stress and public scrutiny aren't for everyone. Pushing a founder who isn't an "IPO guy" to reject an offer can be a disastrous long-term decision.

The moment proceeds from Qualtrics' multi-billion dollar sale hit, the feeling wasn't euphoria but a sense of it being "underwhelming." This highlights the common entrepreneurial experience where the journey and stories created are far more fulfilling than the financial destination.

After a journalist wrote about Qualtrics turning down $500M, founder Ryan Smith began a practice of "working backwards from the headline." He would ask his team, "What's her next article?" This forced them to set audacious goals that would create a compelling public narrative of growth.

An exit that provides a significant financial win but isn't enough to retire on can be a powerful motivator. It acts as a 'proof point' that validates the founder's ability while leaving them hungry for a much larger outcome, making them more driven than founders who are either pre-success or have achieved a life-changing exit.

Ryan Smith's brother, a Google exec, would hang up on him if he discussed customers outside their target of 250 universities. This strict external accountability served as a powerful "forcing function," embedding a culture of extreme focus in the early team.