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Tim Stojka (@TimStojka) is a serial entrepreneur, angel investor, and board leader who has spent three decades building technology companies from the ground up. From programming an Apple II in his parents’ basement to founding three major SaaS firms — including one that raised $40 million during the dot-com boom — Tim has lived the full arc of innovation, hype cycles, and hard-earned product-market fit. His latest chapter: applying AI and language models to reshape enterprise software through his new venture, Nexus Three Capital.

In this conversation with Gary Rabine, Tim breaks down the real mechanics behind creating, scaling, and surviving as a founder — from vitamins vs. painkillers, to why most tech is overhyped early and under-hyped later, to how AI will transform the next decade of entrepreneurship.

In this episode, Gary and Tim discuss:

• Product-Market Fit: why vitamins lose money and painkillers scale

• How a failed stuffed-animal startup taught him everything about inventory and demand

• The dot-com rollercoaster: raising $40M, preparing for a $1B IPO, then crashing to zero

• Why founders should go slow now to go fast later

LinkedIn: https://www.linkedin.com/in/timjstojka/

Website: https://nexus3capital.com/

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