Tweener Talks: Todd Olson, CEO and Co-Founder of Pendo
We go deep on Todd's backstory pre-Pendo, the detailed Pendo founding story and get to the bottom of what motivates someone like Todd to keep grinding.
When I started this podcast, one of the ‘top targets’ was Todd Olson. Then when he agreed to do it, I felt a bit like the dog that caught the car - ok, I have an hour-ish with Todd, what should we talk about. I watched a LOT of Todd interviews and listened to the pods and they all had a pretty common thread: What’s next for Pendo, are you going public, when, etc.
Tweener Times is sponsored by:
Smashing Boxes - A Durham based lean design-centric digital transformation company.
Robinson Bradshaw - A full-service business law firm with a passion for supporting the Triangle entrepreneurial ecosystem. Learn more about Robinson Bradshaw’s startups and venture capital practice here.
ExtensisHR - As a Professional Employer Organization (PEO), ExtensisHR empowers tech founders and growing businesses to scale smarter. We take HR administration off your plate—managing payroll, recruiting, employee benefits and retirement plans, compliance, risk, and more—so you can focus on innovation. For over 25 years we’ve leveraged a people-first approach, customer-centric mindset, and deep industry expertise to ensure employers have the tools needed to stay competitive in today’s market.
Bank of America – BofA’s Transformative Technology Group helps game-changing tech businesses and founders realize their boldest ambitions across a wide range of technology sectors. With hands-on support, world-class resources, and an extensive network – BofA provides the stability and scalability that tech companies need to rapidly grow today and into the future.
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At the same time when you talk to Pendozers and Pendo customers, a couple of common themes come out:
Pendozers: Todd is the most driven, intense and passionate CEO they have ever worked for
Pendo customers: I love this product so much, I want to tell all my friends about it and their friends and their friends friends and Todd is a great CEO.
That’s the hook I went for. What makes Todd tick? How did he come up with this idea (turns out he’s been iterating his way to Pendo since he was basically 14!). He’s been at this startup thing a long time and could stop at anytime and be fine, he doesn’t have a crazy lifestyle. It’s not money that drives him. What is it.
The other trick interviewing Todd is he’s been interviewed like 1000 times and he’s really really good at PR and interviews. Sometimes folks like that never step out of the PR bubble.
In this interview, there’s a moment that he came out of the bubble and we got to the meat of why he keeps going and I think for founders out there, people that work at startups or support them, it’s a really clear human moment of what makes someone so driven?
I really enjoyed this interview and am proud to have captured that moment. When Todd’s up there ringing the bell at NYSE or NASDAQ for the Pendo IPO, I’ll be reposting that segment as a form of celebration for Todd and the team achieving that milestone.
One tip - I think this one lands harder if you watch the YouTube video vs. audio, but either way check it out.
Where to watch or listen 👀👇
You can watch it on YouTube or right here→ (this is a great time to subscribe to our channel)
The Audio version is available below or if you want to listen on your favorite podcast player head here. Reviews are always welcome and hit that +follow or subscribe!
Thanks to Todd, Laura and Jamie for making this happen and your continued support of the Triangle startup ecosystem!