

#132 The Exit: Selling Shipt for $550 Million
9 snips May 8, 2024
Bill Smith, a high school dropout from Alabama, shares his journey of starting and selling Shipt for $550 million. From overcoming challenges and shifting business focus to making the decision to sell, he discusses the complexities and emotions of reaching a successful exit. The narrative touches on entrepreneurship struggles, strategic expansion, grocery industry response, and the exhilarating acquisition announcement at Target headquarters.
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Early Entrepreneurial Spirit
- At 16, Bill Smith leased office space and sold cell phones, making $5,000/month.
- His school contacted his father after a two-week absence, but a counselor supported Bill's entrepreneurial path.
First Exit
- Bill Smith sold his first business, though not for a substantial amount.
- It provided enough capital to start his second venture, Insight, with his father's investment.
Second Exit
- Insight, Bill's prepaid card software company, attracted the attention of industry giant Green Dot.
- At a conference, Green Dot's CEO offered to acquire Insight on the spot, marking Bill's second exit.