Moneywise I Chose Fun Over Profit…. And I Regret It
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Sep 23, 2025 In this engaging discussion, Jordan Schlipf, a serial founder and CEO of a beauty business, shares his entrepreneurial journey and the lessons learned from choosing fun over profit. He reveals the allure that brought him back from investment banking to startups and the challenges of the Rainmaking model, which prioritizes passion but can lead to costly mistakes. Jordan reflects on his current role, the realities of life in London as a founder, and his evolving definition of wealth, emphasizing support and time over purely financial gains.
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Shared Equity De-Risks Founding
- Rainmaking pooled founders' equity so everyone shared wins and losses, trading upside for reduced personal risk.
- That passion-led, non-thesis model produced diversity and fun but limited outsized financial returns.
Plan For Tension In Shared Ownership
- Expect personality conflicts and tension when pooling equity across founders; enforce governance and clear decision rules.
- Anticipate resentment when workloads and outcomes diverge and build structures to manage perceived fairness.
Chasing Vanity Growth Cost Millions
- Jordan says Rainmaking collectively wasted millions chasing vanity growth like opening many agency offices and pursuing the Middle East deal that never arrived.
- They burned cash running a loss-making regional push and kept funding startups without disciplined investment oversight.