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Join me, Nik (https://x.com/CoFoundersNik), as I talk with Steve Wiesner (https://x.com/SteveWiesnerSMB), who spent 20 years in investment banking and private equity before diving headfirst into entrepreneurship. Now the owner of Watershed Associates, a top negotiations training company, Steve shares his journey from high-stakes finance to the challenges and rewards of running his own business. We cover smart acquisitions, why private equity roll-ups can be risky, and the mindset shifts required to succeed as an entrepreneur. Steve's experience in finance, coupled with his insights into buying and scaling businesses, offers a wealth of knowledge for anyone considering their first entrepreneurial leap.

Questions this Episode Answers:

• How do you transition from investment banking to starting your own business?
• What are the key risks involved in private equity roll-ups?
• How can acquisitions be used effectively to grow a business?
• What mindset shifts are needed for those leaving corporate finance for entrepreneurship?
• What lessons can be learned from working with Fortune 100 companies?

Enjoy the conversation!
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This week we covered:

00:00 Highlights & Introduction
02:48 From Investment Banking to Entrepreneurship
06:09 Understanding Private Equity and Its Structure
08:57 The Role of Leverage in Private Equity
11:51 Transitioning to Fundless Sponsorship
15:13 The Journey into Negotiation Training
18:04 Exploring the Roll-Up Strategy in Private Equity
20:58 Challenges and Risks of Roll-Ups
23:49 Integration Challenges in Acquisitions
27:05 The Importance of a Solid Playbook
29:57 Market Dynamics and Fragmentation
32:48 Recurring Revenue and Its Significance
36:07 Final Thoughts on Entrepreneurship and Growth