How to Pick a Business You ACTUALLY Enjoy (In 64 Mins) | 065

20 Feb 2025 · 64 min
Episode

20 Feb 2025 · 64 min

0:00

This content was created by Nathan Barry. This content was uploaded by Nathan Barry. This is a podcast episode titled "How to Pick a Business You ACTUALLY Enjoy (In 64 Mins) | 065" (content_type: PODCAST), created 2025-02-20 and last edited 2026-04-06. It’s a recorded conversation between host Nathan Barry and guest Isaac French about business strategy and choosing what to pursue next. Isaac recounts building Live Oak Lake (≈$2.3M invested, ~$7M exit) and a digital business (masterclass ~$600K, community ≈$200K ARR, ~ $800K total digital revenue), explains the funnel (7-day email course, webinar, sales sequence, Facebook ads, threads on X), and describes content flywheels and monetization mechanics. The discussion maps four strategic options — run a content agency, build a SaaS/direct-booking product, develop another hospitality property, or double-down on scaled content/YouTube — and weighs trade-offs (short-term cash flow vs long-term enterprise value, team size, partnership/operator fit, tax/advisory considerations, and quality-of-life priorities). Nathan offers frameworks and tactical advice for evaluating and pursuing those paths.

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