Most Expensive Mistakes I Made in My 30s

About this video

Dan Martell shares the five biggest mistakes of his 30s, a decade that began in San Francisco building Flowtown with co-founder Ethan and included building and exiting Clarity.fm, which he says raised $1.6 million in funding from Mark Cuban and others and handled hundreds of thousands of calls. First, ‘dirty vision’: he was half-in on Flowtown, travelling and investing elsewhere with no clear personal vision, which he estimates cost 30 to 40% more upside on the exit, and left the company exposed when it depended on a Facebook data source and Facebook changed its API, sending the product to zero. Second, the ‘Steve Jobs effect’: absorbing aggressive, dictatorial founder narratives, he led with fear and anger, created friction, was asked by Ethan to let him run the team, and once freaked out in a product meeting; he credits books including ‘Radical Candor,’ ‘Five Dysfunctions of a Team’ and ‘Start With Why’ with changing his leadership. Third, lost deals (the anti-portfolio): he was in the room with Flowtown investor Travis Kalanick while Uber was being created and passed, and passed on Teachable after a brief meeting with founder Ankur; he puts the total cost at about $60-70 million in lost opportunities and says Teachable later sold for $250 million, so he now invests based on people, disconnected from portfolio or market emotions. Fourth, partying too much for years, losing Sundays to hangovers and workdays to fog, until his wife Renee told him she was pregnant with their first son, Max, prompting him to quit alcohol for life — a decision he says had stood for almost eight years at the time of recording, against a background of his mother being an alcoholic and his own rehab at 17. Fifth, having no coach during Flowtown, after having had an EMyth coach before Spheric; hiring coach Marcy of StartupHappiness helped him through building Clarity solo while his wife was pregnant, with kids 11 months apart and multiple moves, and he now keeps three coaches. He closes by offering his Dream 100 training on recruiting peers, advisors and mentors.

Key takeaways

• Get a clear personal vision before committing to a venture: being half-in on Flowtown cost Martell an estimated 30-40% of exit upside and made decision-making and focus harder.
• Do not copy the aggressive ‘Steve Jobs’ founder style: leading with fear and anger makes top people leave — people quit bosses, not companies — so learn a more positive, candid communication style.
• Judge investments on the founders, not on your portfolio pain or market mood: passing on Uber and Teachable cost Martell an estimated $60-70 million in lost opportunities.
• Treat time, not just money, as the cost of partying: Martell quit drinking entirely when his wife became pregnant with their first son, and credits nearly eight years without alcohol with far more output for family, health and business.
• Always keep a coach: going without one during Flowtown let Martell think too small; he now uses coaches for business and for skills like triathlon and kiteboarding, arguing the ROI is in mindset, accountability and speed.

Episode details: published September 7, 2020 · 17:25 long. Summary written by Self Growth Videos from the episode itself. Business results and any income figures mentioned are Dan Martell’s own claims, shared for education — they are not typical or guaranteed.

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