Harry's father passed away at 55 when Harry was just 27, leaving "a ton of potential untapped." This loss fundamentally altered Harry's perception of time: "Tomorrow is not promised, next year's not promised, the next 10 years is not promised." The average American lives to 78, making middle age actually 39, not 50. This realization drove Harry to stop working for others and build something meaningful. "If I had 20 years left like my father did, would I be spending it doing other people's work?" His impatience became both weapon and weakness, driving action but also creating heartbreak when expectations weren't met.

Drawing from his brother Russell Wilson's NFL career, Harry observed that even elite athletes resist mental coaching despite its proven competitive advantage. Founders face the same challenge: "They think they've already arrived." The ego exists whether you're a first-time founder or multi-exit veteran. Harry notes founders are essentially high-performance corporate athletes investing heavily in skills (product knowledge, sales techniques) while neglecting the mental conditioning that handles pressure. "The majority of athletes still are not yet tapping into this competitive advantage... and founders have that same blockage."

After losing 55 pounds in 2021, Harry realized mental fitness works like nutrition: you need a deficit. "I need to be at a negativity deficit daily, weekly." This doesn't mean avoiding all negativity, but tracking consumption consciously. Instead of CNN or Fox News playing in the background while working, consider the hours engaged with negative content. Track conversations with energy-draining people. Monitor text message rabbit holes with peers. "Negativity is stacking up," Harry explains. His solution: track negativity intake like calories and actively reduce it while increasing positive inputs through deliberate practices.

During summer 2023, Harry shocked his co-founders: "I've cried almost every day, particularly every workday since over the last three months." This wasn't just business stress. They'd cut team members due to cash flow challenges, not performance issues. "I felt like I failed those individuals." Personal family challenges compounded work pressure. Despite having a successful attorney wife, three beautiful daughters, and eventual profitability ahead, Harry found himself "in a dark closet" unable to see the good. The loneliness of leadership hit hard: "Sometimes you feel like you're living a different reality than other people on your team."

Limitless Minds implemented a Slack gratitude channel where team members share daily appreciations. This serves dual purposes: personal joy checkpoints and leadership intelligence. "The cheat code is that as a leader... I get a sense for what my team is grateful for." Over time, patterns emerge revealing what truly matters to each person (family, specific relationships, fitness journeys, financial goals). This deeper understanding helps balance empathy with results. When tough conversations arise, leaders can tap into genuine understanding of individual drivers. "Once you understand what's really important to them... you can tap into this level of empathy."

Harry's most valuable support doesn't come from advisors or investors but founder peers at similar stages. Through Endeavor and Google for Startups Black Founders Fund, he discovered the power of comparing notes with people "wearing the same shoes." His ideal cohort includes founders one stage behind (learning from his mistakes), founders at the exact same stage (real-time problem-solving), and founders one or two stages ahead (previewing upcoming challenges). "Not all the people that have given you capital... have actually built something from zero to one." These peer groups provided perspective: "We're not doing as freaking bad as we thought."

I more than loved this conversation with Harry cause this is once again the proof to me and all you watching/reading, that NO founder, NO successful person is ever “untouched” by fear. The more we watch social-media-polished stories, the more we start to think the people out there have figured it all out. (Please don’t think of me either! 😆). The reality is that when you want to keep growing, life will inevitably put you through bigger and bigger obstacles, and yes, sometimes you may not be fully ready for them. At the end of the day, it’s not a “perfection” game, it’s a “consistency” game, so keep it up! 💪