$300M+ Founder: What Nobody Tells You Before Selling Your Business | Ankur Nagpal | 146

17 Sept 2026 · 63 min
The Nathan Barry Show

17 Sept 2026 · 63 min

0:00

In this episode of The Nathan Barry Show, host Nathan Barry interviews serial entrepreneur Ankur Nagpal, founder of Teachable and Carry (later rebranded as Kerry). They walk through the full lifecycle of building, scaling, and exiting two SaaS businesses, contrasting bootstrapped versus venture‑backed paths. Key moments include the $250 M Teachable exit at $25 M ARR, the $76 M Carry exit at $4 M ARR, and the strategic role of limited fundraising in preserving upside. Ankur explains the little‑known Qualified Small Business Stock (QSBS) tax break that can eliminate taxes on $10‑$15 M of founder gains, and how he leveraged it for both exits. The conversation dives deep into product‑market fit challenges, the myth that second‑time founders find it easier, and the importance of filtering hype. They discuss hiring tactics for a second company, the power of personal brand and audience in recruiting, and the trade‑offs of bootstrapping versus VC, including how large rounds can cripple future exits. Ankur’s move into AngelList’s public venture fund (USVC) is explored, highlighting regulatory considerations and the ambition to democratize private‑market access. The duo also share contrarian “hot takes” on content creation, AI‑generated posts, global salary parity, and angel investing, offering practical advice for founders, investors, and community builders. Throughout, the tone is candid, conversational, and often profanity‑laden, reflecting both speakers’ willingness to share unfiltered lessons from their 10‑year entrepreneurial journey.

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