#72 – How Entrepreneurship Almost Broke Me - Jordan Schlipf

In this episode, I sit down with Jordan Schlipf, someone who’s lived several entrepreneurial lives; building tech startups, investing as a global VC partner, and eventually stepping in as CEO of the well-known beauty brand Cowshed.

Jordan talks honestly about the ups and downs of entrepreneurship: the long hours, the sacrifices, and the moments where you’re forced to question what you actually want from your career.

We get into how he rebuilt his routines, how he learned to lead bigger teams, and the reality of making tough decisions during a company restructure.

This episode is full of practical lessons; whether you’re running a startup, moving into leadership, or trying to figure out your next step. Jordan is refreshingly real about what it takes to grow, evolve, and keep your ambition intact.

00:00 Introduction

01:57 Soul Searching and Career Transition

14:45 The Realities of Entrepreneurship

20:57 The Importance of Health and Routine

26:18 Challenges of Company Restructuring

34:02 The CEO's Evolving Role

34:34 Defining a Good CEO

36:39 The Importance of Recruitment and Culture

38:11 Knowing When to Step Down

41:27 Avoiding Business Pitfalls

45:13 Diverse Business Ventures

49:57 Investment Strategies and Wealth Management

55:22 Reflections on the Finance Industry

01:02:11 Conclusion and Final Thoughts

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