The SaaS Podcast - SaaS, Startups, Growth Hacking & Entrepreneurship 451: Pendo: From Two Failed Startups to $200M ARR SaaS Success - with Todd Olson
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Sep 4, 2025 Todd Olson, founder and CEO of Pendo, shares his remarkable journey from two failed startups to a $200M ARR success. He discusses crucial lessons on overcoming challenges and achieving product-market fit. Insights into the analytics behind improving user experiences highlight Pendo's innovative approach in the SaaS space. Todd emphasizes the importance of bold design choices, the evolution of sales strategies, and defining an ideal customer profile. This engaging conversation offers valuable advice for aspiring entrepreneurs in navigating the startup world.
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Early Professional Coding Sparked Entrepreneurship
- Todd Olson started programming professionally at 14 and worked in a bank while still in high school.
- Early hands-on work taught him practical software and customer skills that shaped his founder mindset.
Failed Exit Taught Hard Lessons
- Todd's first startup nearly got acquired but the deal collapsed after the board brought in outsiders to negotiate.
- That failure taught him not to count on signed acquisition offers until the deal actually closes.
Second Startup Led To Rally And A Problem Discovery
- In his second startup Todd made a leadership mistake by appointing a non-technical CEO and they failed to find product-market fit.
- That company was acquired by Rally, where Todd later discovered the problem Pendo would solve.
