For the latest episode of Mental Wealth, entrepreneur, DJ, and Summer House star Kyle Cooke joins Boardroom CEO Rich Kleiman and Jack Howard, Head of Money Wellness at Ally Bank, for a candid conversation about entrepreneurship, financial stress, relationships, resilience, and finding joy beyond money. Cooke opens up about the rise and struggles of Loverboy, revealing how the company went from having 30 employees and $10 million in cash to losing money for three straight years and forcing him to financially bail out his own business. He breaks down the costly lessons he learned about hiring, debt, cash flow, and knowing when to ask for help. Cooke also discusses how his upbringing in New Hampshire shaped his relationship with money, why his grandparents became early influences on his entrepreneurial mindset, and the biggest mistakes he made while scaling Loverboy. He shares how the brand's reality-TV exposure, his viral moments, and his DJ career have helped create new opportunities while he works to rebuild the business. The conversation also explores the intersection of money, marriage, mental health, and entrepreneurship, with Cooke reflecting on his divorce, the pressure of being transparent about financial struggles on television, and why pursuing DJing became an unexpected source of passion, income, and freedom.

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