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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Are you a serial entrepreneur juggling multiple ventures and hungry for breakthrough growth? In this candid conversation, Silas Deane reveals his battle-tested blueprint—from bootstrapping a game-changing fintech solution in an unlikely industry to executing a $90M exit without investors. If you’re ready to unlock the secrets of scaling, pivoting, and innovating across diverse markets, this episode is your must-watch playbook.
Highlights include:
- How Silas bootstrapped VendEngine from idea to digital disruption
- An innovative approach to transforming inmate financial transactions
- Scaling strategies that grew the business from county jails to 425 facilities
- Merging startup agility with corporate synergy at Tyler Technologies
- Critical lessons on embracing failure, pivoting, and mastering time management
- Leadership insights on integrity, mentorship, and building winning teams
- The mindset behind taking calculated risks and seizing future opportunities, including AI trends
Don't miss out! If you find value in these insights, hit the Like button, share your thoughts in the comments, and subscribe for more game-changing strategies from today’s top parallel entrepreneurs.
Show Notes:
- VendEngine Inc. - https://www.businesswire.com/news/home/20210901005799/en/
- Tyler Technologies (NYSE:TYL) - https://www.tylertech.com/
- KPMG - https://kpmg.com/us/en.html
- Deane/Smith & Partners, a Nashville-based, award-winning public relations, marketing and advertising agency - https://deanesmith.agency/
- NIC transaction management solution - https://www.florida.egov.com/services.html
- University of Kentucky, Gatton College of Business and Economics, Von Allmen Center for Entrepreneurship - https://vace.uky.edu/node and https://vace.uky.edu/bootcamp/mentors/silas-deane
- Junior Achievement of Middle Tennessee, a nonprofit that inspires and prepares young people for success - https://jausa.ja.org/index
- The Power of Broke: How Empty Pockets, a Tight Budget, and a Hunger for Success Can Become Your Greatest Competitive Advantage by Daymond John - https://daymondjohn.com/pages/power-of-broke
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