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Reid Tileston on Grit, Business Acquisitions, and Entrepreneurial Relationships

2024-12-09

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Guest Bio

Reid Tileston is a distinguished serial entrepreneur with a robust portfolio of successfully acquired, grown, and sold businesses. His work with top brands like Harley Davidson, Microsoft, and John Deere has earned him recognition from The Wall Street Journal and Crain’s. An adjunct professor at the University of Chicago Booth School of Business, Reid co-created the Entrepreneurial through Acquisition course and conducts impactful doctoral research. Reid is an Eagle Scout, Ironman triathlete, and outdoor enthusiast who incorporates his passion for adventure into his holistic approach to business and life.

Key Lessons From Episode

  • Empathy is crucial when acquiring a business to build trust with the previous owner.
  • Relationships and connections are at the heart of entrepreneurial success.
  • Understanding the seller's motivations and being malleable in negotiations can ease acquisitions.
  • Maintaining a solid liquidity position is essential for navigating unknowns in business ownership.
  • Invest in select rejuvenating relationships for personal and professional fulfillment.
  • The journey of acquisition entrepreneurship requires time and supportive networks for success.
  • Childhood experiences often influence adult behavior; focusing on current intentional life choices is key.
  • Timestamps

    [00:02] Reid Tileston's Background – Overview of his achievements and contributions.

    [02:29] Entrepreneurial Motivation – Reid discusses his inspiration for entering entrepreneurship.

    [04:39] First Business Venture – Reid shares his start in business ownership inspired by his brother.

    [08:07] Transitioning Ventures – Reid talks about moving on to new business opportunities.

    [14:01] Grit in Entrepreneurship – Discussing the concept of grit in small business ownership.

    [18:23] Building Relationships – Emphasis on the importance of relationships in entrepreneurship.

    [23:55] Empathy in Business – Understanding the seller's perspective when acquiring businesses.

    [26:56] Investing in Yourself – Reid's strategies for personal investment and growth.

    [28:42] Future Goals – Reid’s vision for the next 10 years of his career and personal life.

    [31:34] Advice to Younger Self – Reid’s advice to his 10-year-old self focusing on positivity.

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