I Chose Fun Over Profit…. And I Regret It - Moneywise Recap

Podcast: Moneywise

Published: 2025-09-23

Duration: 38 min

Summary

In this episode, Jordan Schlipf reflects on his entrepreneurial journey, weighing the joys of pursuing passion against the financial sacrifices he made along the way. Despite achieving a comfortable life, he questions whether prioritizing fun over profit was the right choice.

What Happened

Jordan Schlipf, a serial founder and current CEO of a beauty brand, opens up about his path into entrepreneurship, emphasizing that his initial motivations were not financial, but rather a love for the game. His experience in investment banking proved unsatisfying, leading him to quit and explore his passion for startups. He co-founded a project called Rainmaking, where founder investors pooled resources to start various startups, sharing both risks and rewards. Jordan enjoyed the collaborative spirit and the opportunity to pursue diverse interests.

However, despite the fulfillment he gained from his ventures, Jordan grapples with the realization that he could have achieved greater financial success had he focused more on profit. He shares that while he is currently worth about $4 million, he often reflects on the financial sacrifices he made during his entrepreneurial journey. Jordan admits, "It was freaking fun, but I honestly can tell you hand on heart, we would have made way more money had we been focused." He candidly discusses the emotional toll of not matching his financial success with his perceived potential, leading to a sense of regret about his choices.

Key Insights

Key Questions Answered

What is Rainmaking and how does it work?

Jordan describes Rainmaking as a project that functions somewhere between a syndicate and a startup studio. Founder investors pull together their money and resources to support individual startups they find interesting, sharing in the profits. This model allows for collective risk reduction and the opportunity for individual founders to pursue diverse ideas while still benefiting from shared successes.

Why did Jordan Schlipf leave investment banking?

Jordan quit his investment banking job because he found it unfulfilling and exhausting. He recalls the intense demands of the role, stating, 'They fucking own you. You will work every hour of every day.' This realization led him to seek a career that aligned with his passions rather than just financial gain.

How has Jordan's financial success compared to his expectations?

Despite being worth approximately $4 million and earning a stable salary, Jordan feels that he has not achieved the financial success he expected based on his talents and potential. He reflects on the years spent in entrepreneurship, saying, 'There's this massive hole as I went down the entrepreneurial road where that just never returned,' highlighting his feelings of disappointment.

What emotional challenges does Jordan face as a founder?

Jordan expresses the emotional struggle of reconciling his entrepreneurial journey with societal expectations of success. He mentions feeling like he could have proven himself more in the business world, stating, 'I didn't feel like I'd proven predominantly to myself and then honestly to the world that I'd been successful or had a success.' This internal conflict illustrates the mental toll of the entrepreneurial path.

How did Jordan's perspective on entrepreneurship evolve?

Jordan acknowledges that he initially drank the 'Silicon Valley Kool-Aid,' believing that only VC-backed, billion-dollar businesses were worth pursuing. He later realized that his true fulfillment came from making an impact and enjoying the journey, rather than solely focusing on financial success.