How a $150 Estate-Sale Painting Sparked a Multi-Company Empire | Eric Stenson on Pivots, PPP & AI

In this episode of What Keeps You Awake.TV, host David Hooser sits down with serial entrepreneur Eric Stenson of Pivot Equity to unpack how a weekend side hustle—flipping a $150 estate-sale painting—snowballed into a portfolio spanning commercial real estate, tax advisory, government tax credits, and AI voice agents.

Eric shares the wild origin story — that $150 painting later sold for $155,000 — how he rapidly built PPP loan-forgiveness software during the CARES Act rush, and why the willingness to pivot fast is the most underrated founder superpower. You’ll also hear how his family office structure backs ventures like 360 Advisors, Stenson Tamadon ERTC, and RevmMo AI phone agents for restaurants, auto shops, home services, and more.

🔑 In this conversation:
• The “silver tsunami” insight that launched a profitable side hustle
• From art flip to fintech: shipping product fast when timing matters
• Building a multi-business portfolio under Pivot Equity
• Why metrics > vibes, and how to know when to pivot
• Sneak peek: next episode on IT services with our “Protected By” sponsor, MBPS

👉 Don’t forget to like, comment, and subscribe to What Keeps You Awake.TV for more conversations with founders and business leaders.

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