# Ep 10 - From Paperboy to Payroll Prince: Meet Rob Basso, the Consummate Entrepreneur

Page: https://stenobird.com/podcast/crazy-wealthy-podcast-7065850/ep-10-from-paperboy-to-payroll-prince-meet-rob-basso-the-consummate-entrepreneur
Text version: https://stenobird.com/podcast/crazy-wealthy-podcast-7065850/ep-10-from-paperboy-to-payroll-prince-meet-rob-basso-the-consummate-entrepreneur.md
Podcast: [Crazy Wealthy Podcast](https://stenobird.com/podcast/crazy-wealthy-podcast-7065850)
Published: 2025-07-15T04:00:00+00:00
Episode link: https://crazy-wealthy-podcast.captivate.fm/episode/ep-10-from-paperboy-to-payroll-prince-meet-rob-basso-the-consummate-entrepreneur
Audio file: https://episodes.captivate.fm/episode/fc8b43ee-8a79-4470-bf34-eff047e2d45d.mp3
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JSON: https://stenobird.com/v1/public/podcasts/crazy-wealthy-podcast-7065850/episodes/ep-10-from-paperboy-to-payroll-prince-meet-rob-basso-the-consummate-entrepreneur
Duration seconds: 2877

## Resource

Welcome to the Crazy Wealthy Podcast! Jonathan interviews Rob Basso, a seasoned entrepreneur and business coach who shares his journey from humble beginnings to building and selling multiple successful businesses. Rob's journey is truly inspiring. We dive deep into his experiences founding Long Island Advantage Payroll and his subsequent business ventures. Rob opens up about the challenges he faced, including a difficult split with a business partner, and how he overcame them. For all you entrepreneurs out there, Rob shares invaluable insights from his book "The Everyday Entrepreneur" and discusses his current work as a business coach. Whether you're just starting out or looking to take your business to the next level, this episode is packed with wisdom you won't want to miss. Tune in!  IN THIS EPISODE: (00:00) Introduction (01:50) Rob Basso recounts his early life and the entrepreneurial lessons learned (05:21) The creative job-seeking strategy that launched Rob's career in the payroll industry (08:19) Rob discusses his book "The Everyday Entrepreneur"  (09:30) The "Triple Threat" of Entrepreneurship (13:07) Post-exit challenges: Navigating the emotional impact of sudden wealth (26:40) Overcoming partnership disputes and preparing for a successful business exit (35:50) Rob's current role as a business coach and consultant (40:37) Recap of the episode with Jon and Amy KEY TAKEAWAYS: Early experiences, such as having a paper route, can instill valuable entrepreneurial skills like responsibility and customer service. Entrepreneurial success often requires a combination of ambition, confidence, and conviction, coupled with years of persistent effort. The emotional challenges of post-exit wealth can be significant. Having a solid financial plan and advisor is cru…

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