Tropical MBA: Entrepreneurship & Founder Lifestyle

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#863 How One Side Project Built a Ten-Year Business

July 02, 2026

This one's a bit of a TMBA throwback — a story about how to leverage the skills you already have to build a business and life that fits your goals. Hannah Wilnau co-owns Wilnau Design, a web design and digital marketing agency serving independent financial advisors — fully remote, built over ten years alongside her husband and co-founder Greg. It started with a side project she almost didn't do. That one project became her first client, which became a referral, which became a ten-year busine...

#862 The Two-Week Startup

June 25, 2026

Brian O'Connor spent three years building a 40,000-person Twitter following, launched product after product into that audience, and made almost nothing. The turning point came when he stopped looking for clever ideas and started running a boring business where product market fit already exists. He wrote down everyone he knew, sent texts, and sold $20K of recruiting services off a single Google Doc in two weeks. Today he runs TalentHQ, a recruiting agency placing Latin American project manag...

#861 One Niche, One Funnel, Over $50K/Month Profit

June 18, 2026

At his lowest point, Jan Roos was $240,000 underwater. He had a full sales org, a director, reps, ad spend — and was barely breaking even. So he cut all of it. Today he runs CaseFuel, a high-margin agency serving 300+ estate planning law firms, with 25 people and $50K/month in profit. In this conversation he breaks down how he got there: the niche nobody else was serving, the funnel that cracked it open, and what building a genuinely high margin service business actually requires. Guest: Ja...