#453: Building Companies Like an Artist with Berlin-Based Coach Olga Skipper

In this inspiring international episode of That Entrepreneur Show, we welcome executive coach and advisor Olga Skipper, joining us all the way from Berlin, Germany. With over 15 years of experience guiding startup founders, CEOs, and business leaders from inception to IPO, Olga brings unmatched insight into the art of entrepreneurship.

Having coached over 200 leaders globally—and fluent in English, German, and Russian—Olga helps early-stage entrepreneurs navigate complexity while staying true to themselves. From the importance of authenticity in leadership to hiring intentionally and asking for help, this episode is packed with advice that will resonate deeply with founders at every stage.

💡 In This Episode, You’ll Learn:

• Why entrepreneurship is more art than algorithm
• The importance of authenticity while leading a team
• Olga’s early entrepreneurial spark at 16—and how ADHD shaped her career path
• Real talk about hiring the right people for your startup
• Why most CEOs never regret firing too early—but often regret waiting too long
• Olga’s #1 tip for early-stage founders: Ask for help. Often.

Whether you're just launching or scaling your business, Olga’s perspective will help you build smarter, lead better, and stay grounded in your bigger life vision.