Triangle Tweener Talks

00:00:03 - Todd Olson
Do I miss coding a little bit? Of course I miss coding. I love it. And do I love kind of the fun time where I can just kind of like people weren't like paying attention to literally everything I'm doing and like, like micro analyzing it?

00:00:13 - Scot Wingo
Who's taught on the phone with right now? Oh my God, what's it mean?

00:00:17 - Todd Olson
Of course I missed some of those days. But you know what? I really appreciate what we built and I appreciate the fact we built a great company. And is it a perfect company? No. There's plenty of things we have to fix. But I appreciate that the grass is not always greener.

00:00:34 - Scot Wingo
Welcome to Triangle tweenertalks a weekly podcast by Builders for Builders where we explore the startup journey from the idea to the exit and all the lessons in between. With an exclusive focus on founders from the Triangle region of North Carolina. Tweener Talks is produced by Earfluence. Now here is your host, serial Founder and General Partner of the Triangle Tweener Fund, Scott Wingood. Welcome to this episode of Triangle Tweener Talks featuring Todd Olson, CEO and Founder of Pindo. According to public information, Pindo is a 250 million ARR business headquartered here in Raleigh, North Carolina with over 900 people. And you can imagine Todd is a very very busy person. So we really appreciate him carving out over an hour to sit down with us for an interview to optimize our time with Todd.

00:01:21 - Scot Wingo
We recorded in the Pindo Building at around Sunset, so the visuals for this one are pretty spectacular. I know a lot of you prefer to the audio version, but if you get a chance take out check out the video version over on our YouTube channel. This episode is brought to you by our sponsors, Robinson Bradshaw, a full service business law firm with a passion for supporting the Triangle entrepreneurial ecosystem.

00:01:43 - Scot Wingo
Learn more about Robinson Bradshaw's startup and venture capital practice at robinsonbradshaw.com bank of America bank of America's transformative technology group helps game changing tech businesses and founders realize their boldest ambitions across a wide range of technology sectors. They have hands on support, world class resources and an extensive network. BofA provides the stability and scalability that tech companies need to rapidly grow today. Eisner Amper they're one of the world's largest business consulting firms with a dedicated technology practice offering outsourcing, accounting, tax and advisory services. Their experienced professionals serve more than 2,000 technology companies from early stage startups to public enterprises. Discover how Eisner Ampner's stage specific solutions and industry expertise can help you eisneramper.com Tech smashing boxes, a Durham based lean design centric digital transformation company.

00:02:35 - Scot Wingo
And special thanks to our friends at Earfluence. They had a lot of work for this one. They had to carry all their equipment and it was kind of complicated. So Extra double super whammy. Awesome sauce. Amazeballs. Thanks to our friends at Earfluence. I went into this interview a little curious about how, how to approach it because interviewing someone like Todd is tricky. He's done so many interviews, I didn't want to just ask the same questions and you know, get, get kind of what I call pull string answers.

00:03:07 - Scot Wingo
So when you're, when you're, when you've built a company for 10 years and you do a lot of media interviews, you get the same questions. So you just kind of have a rote or kind of a pre planned answer. So I wanted for us to learn something new about Todd in this and so I spent the bulk of my time not on what he talked, not on Pindo.

00:03:26 - Scot Wingo
So if you came here for Pindo, apologize. There's a lot more information about that. But, but what I decided to dig in to based on our, our audience is founders and people that support founders here in the triangle. I wanted to really dig in and understand what makes Todd tick because I get this question all the time that's like, why do you keep doing this? It's like hard and crazy.

00:03:46 - Scot Wingo
So, so why does Todd keep doing this? He's been, you'll, you'll learn. He's started many, many companies. So, so, you know, and also as an, I know Todd relatively well, but just externally he has this ability to focus and drill in and build a great culture. So you know, of the folks in the triangle that's built a great culture, he's kind of, you know, on the Mount Rushmore of that. And even more importantly, what he's done is he's built a rabid customer base. So if you had the fortune to go buy Pandemonium, which is their trade show briefly, and you know, the customers there just love this product and they learn everything about it. They want to tell more people to use it. And that's in many ways your best sales team is happy customers.

00:04:32 - Scot Wingo
He's executing across many, many dimensions. Sometimes you'll see someone really good at recruiting or the customer side or culture or super focused. Todd's the full, full meal deal. Here is my interview with Todd Olson, CEO and founder of Pinda. Hey Todd, thanks for having us at Pindo here. And I was glad we've had to move It a couple times because you're so busy, but thanks for taking the time. Also, it's after a board meeting, so I appreciate. You must be exhausted. So appreciate you doing this on a busy day.

00:05:03 - Todd Olson
Well, thanks for coming in, and I'm glad it worked out. I'm sorry for my schedule. It isn't what I. Yeah, it is what it is, but, yeah, honestly, my energy's coming up, so I'm feeling good today.

00:05:12 - Scot Wingo
Yeah. You said you guys closed some deals, so that's always good. Like ring the gong, kind of. That's nothing more energizing than ringing the gong, so I love that. Do you guys actually have a gong?

00:05:21 - Todd Olson
We actually have a gong. And this one, because it was a special deal, we had a little bit of champagne, a little bubbly, and, you know, honestly, it's just. The deal's great and it feels great, but it's like just being proud of the team and knowing, like, this was one of these deals that was, you know, a precedent center for the team, for the people that worked on it. I think I heard 54 people touched the deal across Pendo, which also shows that we're just really good at teamwork when we need to be.

00:05:48 - Scot Wingo
And you must have a heck of a CRM system.

00:05:51 - Todd Olson
We do, we do, we do. We have a lot of systems, by the way, which is part of what we solve for people, but, yes, we do.

00:05:57 - Scot Wingo
Yeah. Very cool. Congrats on the deal.

00:05:59 - Todd Olson
Thank you.

00:06:00 - Scot Wingo
Yeah, so it was interesting. So I started this newsletter, Tweener Times, and the first thing that you guys had done, I guess when we did it, it was called a non deal roadshow, where you're a private company, you're kind of meeting some Wall street people, and there was a really good note out, and I was sitting down there to write that, and you and I have met a million times, but I've never gone into LinkedIn and looked at your background, and I thought it was really interesting. And I want to dig into it, but, yeah, happy to my, you know, spoiler alert. I kind of came to the conclusion you've. You've had this idea in your head. I kind of imagine Pindo as an idea 10 years ago, and then you started. But it looks like you've been kind of like, you know, working on it a lot longer, which I found. I never really realized that, but I thought that was interesting.

00:06:36 - Todd Olson
Yeah, look, I've always been sort of fascinating about building, and I've been in what you would describe as application development tools nearly my entire career, and I think the early problems in application development tools, as you probably know, was like, can we build this thing successfully within a certain date of a certain quality? And folks actually use it. So I think early pre Cloud, pre Agile, it was pretty darn hard to actually build, ship software, design it, build it, ship it for scale and quality, et cetera, et cetera. So I spent a large part of my early career focused on that problem. I think with the introduction of again, Agile and cloud and some of these other new technologies, it's gotten a whole heck of a lot easier to develop software, which has, to me led to the next problem, which is, okay, now we have all this software. Is it actually serving the users? Is it actually delivering value to me? I do think it's sort of a continuation of my career. I don't think it's like some radically new thing I just started doing. I've been in this world solving these sorts of problems since day one. So, yeah, I do think of it sort of as a continuation.

00:07:45 - Scot Wingo
Yeah, yeah. So let's go back. So where are you from?

00:07:48 - Todd Olson
I grew up in Newark, Delaware.

00:07:49 - Scot Wingo
Okay. Yeah. And then I saw you went to Carnegie Mellon, correct? Yeah. Did you know you wanted to do technical stuff back then or what's your journey?

00:07:58 - Todd Olson
Yeah. So in between those two things, me being born and going to Carnegie Mellon age 14, my mom was bragging to some local bank executive about her son being good with computers, you know, and you have to realize being good with computers with my mother is like, I can turn it on, I can use it. This for context, like late 80s.

00:08:21 - Scot Wingo
You could program the VCR.

00:08:22 - Todd Olson
I can program the VCR.

00:08:23 - Scot Wingo
Our son can program the VCR.

00:08:25 - Todd Olson
Yeah. So this exec kind of took interest. He's like, does he want to interview? So I interviewed. This is a bank, mbna, which was a large credit card bank, ultimately purchased by bank of America. And lo and behold, I got a job at age 14. I had to get special permission and all sorts of documents signed. And I started the first month doing data entry, and that was boring, admittedly. And after a month, someone came by, just literally walked by and plucked. Hey, you're supposed to be good with computers. Come with me. He brought me in, he put me in front of a spreadsheet. Pre Excel. This is 2020. This is a green screen.

00:09:05 - Scot Wingo
So VisiCalc, or one of the.

00:09:07 - Todd Olson
It was 2020, it was called. Yeah. And I think it was just post VisiCalc, just pre Excel in. And he showed me how to do his job. And then after a week of doing it, which Also was boring by the way. I started figuring out that they had this thing called a macro programming language. So I started looking through it and I said, I think this is going to automate this entire job. So I did that. So I basically built programs to automate basically this analyst job. And then I went to him, I was like, hey, I'm done with the work and I'm only like a minute in. What do I do next? And eventually I started automating more and more things and then they're like, okay, we need to put you somewhere else. So they put me in this IT closet with a bunch of people and.

00:09:50 - Scot Wingo
I just eliminated my job.

00:09:51 - Todd Olson
Yeah, like self taught Unix, C. I just learned how to code and I got sort of like just taken away by technology at a pretty early age. And I sometimes tell the story, but I had a nickname of Super Todd because I could just fix things with computers. But. And a lot of, you know, a lot of my, I guess older contemporaries could not do. And I was pretty good under pressure. Like I could be in the room with a senior vice president and something could be broken and they would put me there to fix it because I also didn't realize what a senior vice president was like. They told me to fix this thing. So I didn't. Yeah, I didn't feel the pressure that other people felt. I was also an hourly employee so it was a good arbitrage moment for them. But, but that's where I really got attached to technology. I think the cool thing about that story is that I wasn't hired in it, I was hired into the business. So I had this business acumen because I was sitting with the business. I understood what they're trying to solve. And my job I felt was to take this technology and sort of contort it to solve these business problems. So that was my early introduction technology. Carnegie Mellon to me was like, okay, I'm kind of like a self taught hacker working for a bank. I should probably like go deeper, go wider, like understand the fundamentals. So I went to school for electrical computer engineering. I want to understand like you know, how the computers are made, you know, how they design. So I kind of went deeper on microprocessor design and took a lot of software classes like operating, like classic CS courses. And I felt like that would like round out my skills. And sure enough, yeah, I think it was a good choice.

00:11:25 - Scot Wingo
Yeah, Cool. Did you ever take a compiler class? Those are my favorite.

00:11:28 - Todd Olson
I did, you know, no, I did not take compiler, os, microprocessor design. I Think like, yeah, cool thing. I got to design silicon, which not a lot of people have done and it worked. So yeah, it was a great experience. Carnegie Mel is a very. I mean, you work a lot. I mean, I just, I spend most of my time in computer labs. That's what I remember is being in a computer lab at three in the morning. And I didn't dislike any of it. I actually loved it. So. Yeah, it was really fun.

00:11:56 - Scot Wingo
Yeah. Cool. So you graduate and you've worked at a bank. Were you craving, you know, were they, were they kind of wanting you back?

00:12:03 - Todd Olson
Oh my gosh. Yeah, they, they, they just assumed. Actually it wasn't. They wanted. I think they assumed because each summer I would come back and, you know, want to see my family and, and. But my senior year in college I met Eric Bodick and he had been formulating some ideas. The Internet was just being invented. This is like the early days of the web browser. And he knew that my background was working in a bank and working with large databases and I was good at that kind of stuff. So he started forming this idea, like, hey, you're good with databases. There's this Internet thing. What if we put these things together? What if we bring data from databases and put it on the Internet? And this is very early. There are no app servers. Java hadn't even been invented yet, by the way. So I was writing in some scribbly languages and so we started a consulting company helping businesses in Pittsburgh basically bring old school data to the Internet. And through that experience is when we sort of birthed the idea of the first company we started, which was first named Vision Systems, but became Cerebellum Software.

00:13:06 - Scot Wingo
Ah, Cerebellum. Okay. Yeah. Cool.

00:13:08 - Todd Olson
Yeah.

00:13:08 - Scot Wingo
I didn't realize Eric went back that far.

00:13:10 - Todd Olson
Yeah, we did.

00:13:11 - Scot Wingo
You guys go to high school together or something?

00:13:12 - Todd Olson
No, just. We met in college. We probably met his junior year, my sophomore year. He's a year older in school, but. But yeah, we spent a good amount of time starting probably my sophomore year. But then I dropped down to a part time student my senior year and I worked full time and was a part time student and that's when we started in earnest, raising some capital and building the business.

00:13:36 - Scot Wingo
Cool. So Sara Bellum was venture backed?

00:13:38 - Todd Olson
Yeah, it started as a consulting company. So we had revenue since day one, but then we raised first to friends and family and then, yeah, then we had. Yeah, we had venture funds involved.

00:13:47 - Scot Wingo
That's cool.

00:13:48 - Todd Olson
How old were you coming started? I was 20. I couldn't drink. I remember that part.

00:13:52 - Scot Wingo
You Know the champagne, ring the gong. You're like, yeah, Apple sprits.

00:13:58 - Todd Olson
That was pretty goody two shoes back then. So. Yeah, yeah, no, we still are.

00:14:02 - Scot Wingo
Still are. 100%.

00:14:05 - Todd Olson
Yeah.

00:14:07 - Scot Wingo
So you raised some friends and family. Did that company have an exit?

00:14:10 - Todd Olson
No, no. This is like incredible heartbreaks, you know, it's like we. Well, look, we raised friends and family to build a product, we built a product, we got a little bit of traction. But to be honest, this is before the term product market fit was actually coined. We did not have product market fit. Shocker. And I, you know, look, we didn't, we didn't have product market fit. We didn't obsess over it.

00:14:36 - Scot Wingo
You're probably too early. Like, you saw us so far ahead. People are like, wait, what's the Internet? And you're like, let's put a database on it. And they're like, whoa.

00:14:43 - Todd Olson
Yeah, we actually built a product to do database federation for the Internet, which. There are products that came way after us that were successful, but we were way too early. And yeah, I learned so much from that experience. But yeah, there was a day where the board called us while we were at lunch and they said, we're gonna have to get rid of. Oh, I skipped a little bit. I apologize. So what happened is we had an acquisition offer. I realized that with the cash in the bank, we started cold calling people. One of the folks we were targeting were application servers, the job application server market. So we ended up getting an inbound acquisition offer from silverstream, which was a Boston based VC backed company. Actually they're a public company at that point. We had agreement, so it was like signed an loi. This was done like we were like, I wouldn't say I was counting my money, but I was feeling pretty darn good. And then this was the height of the Internet bubble. So our board saw it sees like what a 21 year old and a 22 year old or 22 and 23 year old negotiate this deal and they're like, this has got to be too low. You need a banker. So they threw out the agreement, they hired a banker and said, we're renegotiating this because we think this is worth two to three times more. Now by the way, the multiple on that deal, the original deal was a crazy multiples, probably 20 to 30x. They somehow thought that we should get 40x or whatever and really pissed off. The CEO created the entire relationship. At that point, that company who had given us an LOI had bridged us to the transaction. So they Put in a little bit of money to get us to the transaction, but that's it. We had a bridge to the transaction. It didn't happen. So, yeah, that's when the board called and said, look, we have to obviously shrink our spend. They did keep me. Poor Eric. They kind of got rid of basically everyone who wasn't an engineer because they wanted take the assets and do something with it. I got super frustrated.

00:16:38 - Scot Wingo
You learned picking your board and investors is very important.

00:16:41 - Todd Olson
Oh, it was a heartbreak. It was just. It was the right outcome for the business.

00:16:46 - Scot Wingo
And yeah, after that, selling in V1 was the right outcome for the business. Yes.

00:16:51 - Todd Olson
Yeah.

00:16:52 - Scot Wingo
In hindsight, but yeah, yeah, I mean.

00:16:54 - Todd Olson
But look, I learned a lot. I did have to like lay off a whole bunch of people that day. That was, you know, it was like, you know, I was a really young person. That was a. I mean, I guess you could call it a good experience, but it was terrible, you know, and I joke with people. That's when I actually discovered alcohol for the first time. So not in a terrible way. I don't have a problem, don't worry. But there's no question that that was very humbling. But I guess a couple things happened from that, which is important for me is that I knew that if I could do it once, I could do it twice. I was like, if I can get that close at this age, oh, I could definitely do this. So it gave me a confidence as a person who grew up working at a bank. I just seem to work at a bank. I have a picket fence, whatever, family. And I was like, huh, I could be an entrepreneur. Like, this worked. And that's, I think, been sort of how I now think of myself. But it wasn't until those times early that I actually really thought of myself as, okay, this is like who I am probably.

00:17:51 - Scot Wingo
How big did it get?

00:17:53 - Todd Olson
Like number of people over 70? Close to 90.

00:17:57 - Scot Wingo
So you got a 23 and a 22 year old managing 70 people. People.

00:18:00 - Todd Olson
Yeah, yeah, yeah.

00:18:01 - Scot Wingo
And I think until you do it, you don't realize you can. And then you're like, yeah, there. It's not that hard.

00:18:07 - Todd Olson
Yeah, I mean, look, I. I think I learned a lot actually. We split up the world. I ran HR for some reason. Like at the time we didn't have an HR system. So I was like hand calculating taxes for people's paychecks on like giant tables. I mean, this is. Yeah, this is like pre a lot of things. So, yeah, you learn a lot.

00:18:23 - Scot Wingo
Didn't have gusto, just kind of do that for me?

00:18:25 - Todd Olson
Yeah, there's no gusto, no nothing back then, but yeah, you learn a lot. And it was obviously a formative experience, but then I find myself sort of not really doing. They were paying me, but then I was sort of really bored. And that's when TogetherSoft, which is a Raleigh based company who we were partnering with at the time, discovered I was sort of doing nothing. And the CEOs like, huh, well, this is interesting. And that's sort of what really brought me to Raleigh.

00:18:52 - Scot Wingo
Yeah, yeah. We owe togethersoft a lot for them.

00:18:54 - Todd Olson
Oh yeah, I, I owe a lot. Together a lot. So, yeah, what were the.

00:18:58 - Scot Wingo
I've met those guys. What were their names?

00:19:00 - Todd Olson
Oh, Peter Code was the CEO and.

00:19:02 - Scot Wingo
He'S the guy, he's famous, right? He's like, yeah, yeah, he, he's a famous tech guy because of entity relationship diagrams.

00:19:09 - Todd Olson
Yeah, yeah. Or mapping things like that. Yeah. Object relation.

00:19:12 - Scot Wingo
This is old school.

00:19:13 - Todd Olson
Yeah, he. Very old school.

00:19:14 - Scot Wingo
Peter.

00:19:15 - Todd Olson
Peter Code. Yeah. So we competed in disrupted rational. Actually our product was incredibly good. So. And they had this issue where they, they had a team of engineers in Russia and they needed someone who would fly to Russia and manage this team of like 250 people. Now, mind you, you just heard the largest company I had ever managed was like, I think it was, I think we got to maybe 90 and they're going to hand me a team in Russia of 250 people. And I never really left the country, so.

00:19:44 - Scot Wingo
Did you have a passport?

00:19:45 - Todd Olson
I know I had to get a passport and they helped me get a passport and they, they moved me to Raleigh because like all the executives were here and I had a small team here, like 30ish people here. And I had 250 people.

00:19:58 - Scot Wingo
There was this like in Moscow or.

00:20:02 - Todd Olson
Like St. Petersburg, I'll never forget. They put me on a plane, they sent me to St. Petersburg, and the first thing you do is you have to get rid of the head of the office. Go fire him. And I was like, okay, I can do that. And then I of course took over and then established new leadership and took over. But it was, I mean, incredible experience. I ended up spending 10 days a month or more every month of my life for like almost three years traveling back and forth between Raleigh, which, like I did fly, Raleigh, Dulles, Frankfurt, you know, St. Petersburg. And then I made a small team in Prague. So I flew through Prague and then back. And then that's like, you probably still.

00:20:38 - Scot Wingo
Have some miles from that.

00:20:39 - Todd Olson
Yeah, I still have some miles. I have a lot of experiences. I yeah, that's like trial by fire. But an incredible company. We were doubling. It was a real software company. I learned so much around at the first company was me just figuring it out myself with Eric. This one was. It was a real software company. I learned how things are done. And interestingly, one of the Peter eventually departed and they put in a new interim CEO. A couple. One was a guy, Bill Volek, he worked at Silicon Graphics. I mean brilliant technologists. I learned so much for him. And then Jeff Lunsford, who's now the CEO of Telium, are still very close friends. He took over and I worked for him very, very briefly. So great experience. And I learned managing Russian engineers isn't very different than managing US engineers. That's one thing I just assumed it's going to be really different. It really wasn't as different as I thought. But it also gave me experience because at Cerebellum I built all the code from scratch. I knew everything about the code base. Take over a massive code base. And not having written a line of code in it, I kind of had to exercise different management muscles and think differently about how I lead the business. I also see the funny thing is Takeoff didn't have product management, so I actually did product management. We just didn't call it that at the time. Product management as a discipline was pretty nascent back then. So that also you could argue that if I hadn't had that experience, like Pendo may not be what Pendo is because I essentially did that function earlier.

00:22:16 - Scot Wingo
In the seat for a long time and felt the pain.

00:22:17 - Todd Olson
Yeah. And I did all the analyst relations and I talked to Gartner and I got us in multiple magic quadrants in the upper right. So like I lived that experience firsthand and that was a great one.

00:22:29 - Scot Wingo
So yeah, folks in that part of Europe are tricky to manage because they're wicked smart. But they also culturally, they don't want to tell you things are bad or going wrong. So everything's always like very good. And then you're like, you're starting to get your spidey senses tingle and you're like, no, I don't think you're building what we think we're building. And like all's good.

00:22:51 - Todd Olson
Yeah.

00:22:51 - Scot Wingo
And look, did you kind of learn some interesting things managing it?

00:22:54 - Todd Olson
Yeah, look, I'm a very hands on leader. I think even today at our scale, I'm still, I'd say a hands on leader. I'm in it, you know. And I think one of the ways I stay in it with respect to products. I'm using products constantly, every drop of every product. And those days I was an on premise software. So I'm like every drop I'm touching, playing with, providing feedback. I'm with the teams, I'm going to meetings if I need to. So I'd say that's sort of the way I lead. Like we reviewed, I wrote every single defect for years. You know, I ended up knowing the product really, really well despite not having written the code because I was just like I was probably the biggest user of the product and I think that really helped me. Spirit. Yeah, I think so.

00:23:37 - Scot Wingo
Cool. And then somehow Borland intersected in there like. Yeah, so Borland, they bought Borland, right?

00:23:42 - Todd Olson
Well, this is, you know, we decided as a company we wanted, we, we thought we had to cut out the IDE. So we ended up building an IDE, TogetherSoft that obviously started attacking Borland a bit. They wanted to figure it out. So they basically bought the company. And interestingly I thought it was a bad deal. I and a few other execs that were at togethersoft called the board and like, please don't do this. Like at the time the founders had both left and I think the founders were like, let's get a payday, which I totally respect. I mean they had the ownership, right. But I was bummed. Like we were winning, we were building great product. We were winning, we were really winning. And to sell. I was so sad at the time. But by an interesting turn of events, the person who bought the company was Frank Slootman, which of course no one knew who he was at the time. I got to work directly with Frank for Frank for basically a job before data domain for him, which was honestly an amazing experience. He's an amazing executive.

00:24:47 - Scot Wingo
And for folks listening that don't know Frank Slootman, he was then CEO of.

00:24:51 - Todd Olson
Snowflake and Service now. So like, yeah, he's a legend.

00:24:57 - Scot Wingo
He's like the king of large SaaS. And he right up there with Benioff.

00:25:00 - Todd Olson
He's an amazing leader. I mean he's. I learned so much just watching, watching him operate. So like that was a really cool experience.

00:25:08 - Scot Wingo
CEO thing. He does a lot of speaking now about like the cadence and setting the pace. Did you, did you even see that back in those days?

00:25:14 - Todd Olson
Oh yeah. There was no slowdown with Frank. It was always go, go, go, go, go. And I think that's why he liked me. I remember at this time I was probably still 26. Yeah, I could keep up. I had no Issues Keeping up. I loved it. I was like a sponge back then. So like. And interestingly, part of the acquisition is for me to move to the Bay Area and I almost did. I mean, I committed to doing it. I was like going back and forth. But then Frank left and that's part of why I never moved to the Bay Area, because his replacement just wasn't Frank. I think if Frank had stayed, who knows if we would be talking about even be here in Raleigh because, like I had committed to going there, but just through a turn of events and like, you know, all my family's on the East Coast. It's just like, it was pretty fascinating how it all turned out.

00:26:02 - Scot Wingo
So didn't the Borland CEO famously, like they went public and he spent a ton of money on a building and then it ended up distracting and they just totally missed their numbers for like a year because he got distracted by this book.

00:26:13 - Todd Olson
His name is Philippe Kahn. There's a thing in the back, a sculpture garden that is affectionately referred to as Conhenge. Yes, I've walked around Conhenge, which I had an office in that building, which was quite nice. But yeah, so he wasn't there when I was there. Dale Fuller was there. Dale was famous for basically extracting cash from Microsoft for anti competitive practices. So Microsoft, for those who don't know, the entire C programming language was built by former Borland engineers, Anders Helzberg. They basically recruited and they had cars. Microsoft was set up at a hotel near Borland. They'd send cars wrapped around and just pluck people from the building all day long. And that is against the law. So. So I will say Dale, I think he got $250 million, which honestly is what was the catalyst for growing, regrowing the business and being able to do acquisitions and ended up being like it all served as funding, which was so kudos to him. And Borland had pivoted to an enterprise business, hence why they bought TogetherSoft. So like it was an interesting time, but departures, other things. I mean, it was not my. Yeah, it was a learning experience for me. But I think after my one year was in, I think I was ready to move on and I knew I wanted to start.

00:27:36 - Scot Wingo
Yeah, Another interesting celebrity from that era. There was this company at my first job called Pure Software and we were a big user of it and I loved it because it would like go debug the code for it in a way nothing had ever done before. Like the IDE would get you a little bit, but this thing would just like say there's a memory leak right here. And I'm like, ah. So then the CEO calls me one day and he's like, will you do. And I was like raving to their folks about how it had helped me save all this time. He's like, will you do a testimonial? So I did this video for them and that was Reed Hastings. And then they got acquired by Rational, who competed with you and then he became CEO of Rational. Right?

00:28:06 - Todd Olson
Yeah.

00:28:07 - Scot Wingo
And they started this company called Netflix.

00:28:09 - Todd Olson
Correct. And I knew all these people really well because I was the one who was assigned to. There's this open source project called Eclipse. IBM realized that the existential threat wasn't all these companies, it was actually Microsoft. So they created a development environment because they realized whoever owned the developers hearts and minds.

00:28:28 - Scot Wingo
Developers, Developers. Developers. Developers.

00:28:31 - Todd Olson
Exactly. So Microsoft was doing and doing a good job. So IBM's like, the only way that we can win is do an open source version and get the Borlands, get everyone else on our side. The Rationals.

00:28:40 - Scot Wingo
It's the Battlestar Galactica strategy.

00:28:42 - Todd Olson
I was on the board of Clips, the founding board. I was on the board for several years actually. And I represented both TogetherSoft and I represented Borland both on the board. And I got really close to the Rational people because we're on the same board. And we realized like, the ultimate threat is not each other. It is this behemoth in Seattle or Redmond. So I think, good. Yeah, it takes me back. But fun time, good learnings.

00:29:05 - Scot Wingo
Cool. So then at some point you start Sixth Sense software in 2004 is what LinkedIn says. I don't know if.

00:29:12 - Todd Olson
Yeah, it feels right. Yeah, look, I left and look, what was my experience? I was like running around the world managing a bunch of developers and I was like, huh? It's really hard to manage all these developers from around the world without actually physically going there. So I came up with ideas like, we need analytics on what's going on with developers and are my projects going to be on time? How can I automate this task report? Rather than going around asking people manually, are you doing this? Is this done? So I came up with this idea. Development teams need essentially business intelligence to run their shops. And interestingly, this is another idea that's way too early because now there's a bunch of companies doing very, very well in the space. And they basically did what we did, but we built. Yeah, that was the premise of the business. That was also the first time I've ever built a cloud company. So we were multi tenant SaaS from day one. And wow. There's like. I mean we built a cloud based multi tenant BI solution. I basically took all this open source stuff and I hacked it to be multi tenant and it was really sophisticated at the time. I mean like, very interesting work.

00:30:22 - Scot Wingo
But 04, there was no AWS, so you had to, you had servers, server, you name it.

00:30:29 - Todd Olson
I mean I.

00:30:29 - Scot Wingo
Were you over at Hosted Solutions or.

00:30:31 - Todd Olson
Yeah, I was at Hosted Solutions.

00:30:33 - Scot Wingo
Did we run into each other at that point?

00:30:35 - Todd Olson
I don't know.

00:30:36 - Scot Wingo
Channelvisor was 01, so I was three years in. And we were building SAS too. Yeah, like we had to run into.

00:30:41 - Todd Olson
Yeah, I think we're right next to each other too.

00:30:43 - Scot Wingo
I remember being in meetings when you were at rally for sure.

00:30:45 - Todd Olson
I was at that terrible building right across from the. Right behind the outlet mall there. So yeah, I remember that vividly. So we see that Greek kitchen thing almost every day. But. But yeah, those are interesting days. But this is another challenge where, you know, we raised money from inner South.

00:31:03 - Scot Wingo
Whoa.

00:31:04 - Todd Olson
And old school. We had. We're like, yeah, we can get this thing out and we can get some revenue in, I don't know, eight months. Like, I don't know. Or six, I don't know. Whatever the number was, it was like wildly optimistic. And then what? So what you do is you rush product, you, you and you start prematurely scaling sales. And the other thing about this is I came up with the idea. I wanted to launch a company, but I was like, I really need a business guy to lead this thing. I'm not a business guy, I'm a technologist. So I recruited the head of sales from TogetherSoft to be the CEO of the company. Greg. Great guy, Greg.

00:31:37 - Scot Wingo
What's Greg's last name?

00:31:38 - Todd Olson
Brunel. B U R N E L. Great guy. I don't think I understood what the decision meant when I made that decision because I was like, oh, I still get to set core values and do other things. But I realized VCs, when they see the CEO, does treat the CEO very, very differently than essentially everyone else.

00:31:59 - Scot Wingo
And how do I like particularly that generation of VCs? There was not a lot of respect for the tech founder.

00:32:04 - Todd Olson
It had a lot of unintended consequences. That, yeah, not only do I think it was great for the business, it certainly wasn't good for me. And yeah, I think that that company, it was a challenging time to be in as well. So we ended up having an exit in 2008, which is, everyone knows 2008 is one of the, like the, you know. So I think that was a tough time. But we never got to product market fit and we burned. We burned through cash.

00:32:32 - Scot Wingo
And was the idea like an at lazy and suite or like this was before really agile or agile kind of.

00:32:40 - Todd Olson
Almost like Jira was just not even really in. Not a thing. This was like pre Agile tools even. We ended up selling to rally software, which was an agile tool. So I would say that it was certainly that genre. My idea was like, look, if you're in the complaint, of course I was like Big Brother because we were capturing crazy amount of metrics about what engineers were doing. But it's like, how do we get more efficiency out of engineers? What engineering teams, what do we learn from people are out doing? Outsourcing was huge back then to India and Eastern Europe. How do we get visibility in what our outsourcing providers are doing? So that was the vision of the product and we got some traction and we got some customers, but it wasn't people's first problem. So when we got to 2008, a couple things happened. One, the board, I think there's just issues going on. Greg maybe wasn't the right fit at the time or what have you. And so I had to work through a CEO change of the board. So I did become CEO probably in the last nine months of the business, roughly. And then I was like, hey, you have no cash to the bank. Figure it out. And so we went on a tour to either raise capital or sell the business. I was comfortable with either. I was fully prepared to run the business. And honestly, it was a great experience for me because I took over this team and I said, look folks, we have six months of cash left. I think I remember this town hall. Like, I am going to be transparent with you in every single week on what I'm doing about it, what our plans are, and you're going to know what I'm going to know. And I'd appreciate if you stay because if you all leave, I'll have nothing really to sell because I need some assets and some technical people. And you know what? I didn't lose a single person during it. Actually, some people work here that stayed during that.

00:34:27 - Scot Wingo
Transparency has a way of building some loyalty.

00:34:29 - Todd Olson
I learned a lot about transparency. I think that was my formative experience there. And then we did, we did get a transaction. We got a transaction done December 31, 2008, just before we ran out of cash.

00:34:41 - Scot Wingo
We never, you know that that's so rip. Good times was September. So you Were. I mean, it's kind of like Covid, you know, But. But it was. In some ways, it was worse than Covid because there wasn't a bounce. There wasn't a bounce. Things were going down. There was. We had a problem at Channel Advisor where we had a money market fund where it broke the dollar. And we're like, all our money in the bank is at risk. And we were like, we just raised like a 20 million. And we're like, oh, my God. It was, like, scared. Like, the whole financial system felt like it was crumbling. In hindsight, it's hard to create the amount of. So, yeah, that was an incredible deal to get done with that back.

00:35:22 - Todd Olson
And we had two. This is the crazy thing with the. We had two offers. I turned down rally first, and then the other one fell through. I had to go back with my tail between my legs. I was like, look, I know I turned you down, but we're open now. And you know what? They didn't take advantage of the situation. Good, honest people. And here's the cool thing. Every single person that stayed with me got a job offer from the new company. We had no disruption of benefits, simply nothing. And I think that was.

00:35:51 - Scot Wingo
At that time, having a safe harbor was extremely valuable.

00:35:55 - Todd Olson
Look at the stage landing.

00:35:56 - Scot Wingo
Having benefits from.08 to 09 was hugely.

00:35:59 - Todd Olson
And then fun fact for investors that actually stayed. Investors in Rally. Rally did go public in 2013. They actually got returns. Now, the ones that gave up or maybe, like, didn't hold on to stock or did whatever, they would have not made money. But if you held onto the money, you actually made money. And that is formative for Pendo because the first seed check came from one of those investors. First he took. So the fact that I think took over this company with six months of cash, and I turned what they had considered nothing into something. Showed that, look, if you can create nothing into something, maybe if he has more than nothing more can happen.

00:36:39 - Scot Wingo
Was Sixth Sense a stock transaction into Rally, basically. And then that then had a. Yeah.

00:36:46 - Todd Olson
So ultimately, was it the outcome we expected? Of course not. What I say, I'm not buying moves. I'm trying to brag about this at all. No, we did not do. My job is to return money back to our investors. Did I do it to the level? No, I didn't do the level.

00:37:03 - Scot Wingo
I wish something. I'm not a math genius, but something is greater than zero.

00:37:07 - Todd Olson
I think so.

00:37:07 - Scot Wingo
And if they got their money back.

00:37:08 - Todd Olson
Yeah, I got humbled a lot when I was raising money for Pendo. At first, like, don't brag about that. That's not something I was like, okay, fair enough. Now granted, if they invested in Pinto, they would have been fine back in those days. But yeah, a lot of lessons from that rally and then being there was a really great experience. As I said, the company went public in 2013. I had the opportunity to. They were awesome. They're like, hey, do you want to work on the S1? I'm like, sure, I'd love to work on the S1. So I helped write, co authored the business section of the S1. And I was in every drafting session. I built a lot of relationships with bankers. I know a lot of financial analysts. By the way, some of the same financial analysts then who covered Rally are now covering Pendo. So they remember me from back then, which was actually pretty powerful. I think the CEO was really good at just sort of. He didn't want to be in some of these things. And he really gave me this opportunity that I don't think every company would have done.

00:38:04 - Scot Wingo
So did you write the mdna?

00:38:05 - Todd Olson
Kind of part of it from the first paragraph on. And we were looking at other S ones. We were copying and. But it was incredible also just being in the room and hearing like, okay, there's this new constituent called public investors and this is what they care about. And so you start thinking differently about your business and you realize this is a whole different exercise, it's a different muscle you're building. But I think it was that to me and filing. I'll never forget when we filed my son, who's now 28, he was 16 at the time, he was with me just hanging around Denver and I'm like, we filed this thing and I was exhausted. You know, we have this thing called drafting, basically these drafting rooms and there's like pool tables in it. Cause you're waiting for this physical book to be printed. It's a crazy thing. But then we're done. Like, I was like, let's go hike a 14er. So the next day got a cracking on it. I hiked a 14,000 foot mountain, which I think they did wipe me actually physically after that. But yeah, just really memorable experience.

00:39:05 - Scot Wingo
Yeah. So Rally, for folks that don't know, Rally was Agile Software.

00:39:09 - Todd Olson
Agile Software development tool. So yeah, very similar Borland, you could argue, like basically the same space. Very similar rational. So my background in all those other companies, like was very, very relevant.

00:39:21 - Scot Wingo
Devtech, you're on like your third or fourth DevTech.

00:39:24 - Todd Olson
Yeah, yeah. And yeah, it became sort of like a Thing definitely a specialty. And I leveraged that. So, yeah.

00:39:31 - Scot Wingo
Cool. Did you get to. Did they do NASDAQ or New York Stock Exchange?

00:39:35 - Todd Olson
New York Stock Exchange. Got to ring the bell. Very cool.

00:39:38 - Scot Wingo
And was that when the CNBC set was on? Were they on there by then?

00:39:43 - Todd Olson
Yeah, Kramer was there. Yeah. Yeah. I mean, look, there's a Faberge egg in the New York Stock Exchange, which is an amazing thing. Like, we had breakfast there. Like, look, great experience. But I can tell you when I was on that stand and I was looking out and I just kept thinking, this is not my company. Meaning, yeah, I sold a company to it. But it fueled something inside of me. Like, okay, I got here now, but this isn't my company. I got here with another person's company. I gotta figure out a way to do this myself. So I left shortly thereafter. In part because honestly, the exciting part is actually writing the document, waiting actually to go public. And there's some other things.

00:40:22 - Scot Wingo
Did you get to go on the roadshow and kind of watch that?

00:40:24 - Todd Olson
I did not go on the roadshow.

00:40:26 - Scot Wingo
Who was lead left on that?

00:40:28 - Todd Olson
Lead left with Deutsche Bank.

00:40:31 - Scot Wingo
Wow, it's a deep cut.

00:40:32 - Todd Olson
There's an interesting.

00:40:33 - Scot Wingo
I did not. Todd didn't know that question was. Cause that's like, That's a good memory.

00:40:37 - Todd Olson
Yeah. Well, I remember this. Originally it was Barclays, but then there's an issue with the Barclays banker. Then it was like Deutsche. But yeah, look, good people. The CEO was awesome. He said, here's the roadshow deck. You record your version of it. So I remember sitting in a hotel room and doing my pitch. And yeah, I think he borrowed some of that and he really good job. I mean, honestly, successful transaction team was awesome. I learned a lot. Yeah, good people.

00:41:04 - Scot Wingo
But it's hollow because wasn't your company.

00:41:07 - Todd Olson
It just looks like it was motivating. I was like, yes, I saw enough now where I was like, okay, I think I can do this.

00:41:16 - Scot Wingo
Seen the brass ring, but it's just like not. It's over there.

00:41:20 - Todd Olson
And for context, people, you can look it up. Rally for context. The 50 ish million dollar company when it went public, I think 54 roughly in ARR for contest. Interestingly, way bigger now. But we're not public. But it's interesting how I thought that was the thing and now I'm still trying to get back to it. And we're a good bit bigger, which is crazy to think about it.

00:41:47 - Scot Wingo
It's not fair. The further you get, they keep raising the bar. It's like kind of ridiculous. In a way. But we're not gonna solve that.

00:41:54 - Todd Olson
Yeah, we're not gonna solve that here.

00:41:55 - Scot Wingo
So what year was this at that IPO?

00:41:57 - Todd Olson
2013.

00:41:58 - Scot Wingo
Oh, that's when we went public too.

00:41:59 - Todd Olson
But look, I departed there shortly thereafter. I think the back and forth. Well, one is a Boulder based company, and I did not live in Boulder. I lived in Raleigh, and I led the Raleigh office here. But to have influence and power and, like, you had to be there a lot and honestly took a toll on my family and me. It was just like every week I was getting on a plane and probably wasn't the best thing for me long term. And part of what I thought is, hey, if I start a company in Raleigh, I'm more likely to be in Raleigh, which is probably better for my family and for me. So the right path is for me to find a way to start a company here and stay here and kind of go more local. So that became my focus.

00:42:37 - Scot Wingo
Cool. So tell us the Pindo founding story. So Eric had come into the story before. Where has he been during the rest of the year?

00:42:45 - Todd Olson
So our paths just didn't cross. He did his own thing, started a few things, joined a few things. He was in Pittsburgh, then in the Bay Area, back to Pittsburgh. But we were staying in touch. I think we were just kind of looking for the right timing of various things. So when I left and I took the whole summer off, a real good debrief, I started reconnecting people that I just lost touch with. I was running so hard and I was traveling so much. I actually lost touch with Eric for a period of years. That was honestly terrible that I lost touch with someone who's such a close friend. And then Rahul Jain, which is one of the other color founders, he was actually at a VC who helped me sell Sixth Sense to Rally. But once I sold Rally, I didn't talk to him for four years, which is terrible. So I called him. What's he doing? He's at Cisco. We're chatting about a few things. And then. And then there's this person here locally, Eric turned. And everyone for years said, you got to meet this guy Eric. And I'm like, oh, I'm really busy. I'm never here, blah, blah, blah. And really, I didn't have an excuse of being busy. I wasn't busy. And it was the perfect opportunity. So I ended up having coffee with him at the Morning Times just a few blocks away.

00:43:58 - Scot Wingo
Did you just leave Rally and just like. Or were you at Rally kind of post ipo? Just Kind of J Chilling. And then.

00:44:04 - Todd Olson
No, no, I left.

00:44:06 - Scot Wingo
Oh, you just like left.

00:44:06 - Todd Olson
You're like, I don't multitask.

00:44:08 - Scot Wingo
Yeah. Were you purposely. I'm going to leave and start my own company. I don't know what it is yet. Or did you actually have an inkling? I left a spark that became Pendo.

00:44:15 - Todd Olson
I left and I knew the next thing would be starting a company. I didn't know Pendo was going to be it yet. I remember sitting there just thinking to myself, okay, what am I going to start now? Now the good news is I came up with the idea of Pendo like almost instantly because at Rally, I had built a homegrown version of or managed a homegrown version of product analytics there. We had tried in that messaging there. I built some of these things from scratch and it was painful. It was like completely manual. I was like, huh, this data is really valuable, but it is super painful and expensive to capture.

00:44:48 - Scot Wingo
So this was no longer just the developer. This was like it gets deployed and you see how the customer's using the product.

00:44:53 - Todd Olson
See how the customer's using the product. We would pipe into Salesforce.

00:44:55 - Scot Wingo
Was this in reaction to Google Analytics, just wasn't getting it done or.

00:44:58 - Todd Olson
Yeah, Google Analytics was not getting it done. You ended up needing to know, like, what people features are people using, which customers are using them, which user, which customer. Yeah. To one of the seminal releases I had at Rally, I released this huge product. I did a four city roadshow with Geoffrey Moore. I mean, we spent real money on it. I was like, this is going to be amazing. Every customer is going to love it. And then three months after the launch, I get the usage metrics manually and no one was using it and the features weren't being. Whoa. It was mind blowing. It was like, how did we not know this? We spent so much money on this.

00:45:32 - Scot Wingo
We did this big PR thing.

00:45:33 - Todd Olson
Yeah, they've got to use the product.

00:45:34 - Scot Wingo
What's wrong with these people?

00:45:36 - Todd Olson
When I realized, yeah, adoption is what really matters because we're not going to get the revenue if no one touches this thing. And why aren't they touching it? So I started obsessing over this problem. So I think when I left, I had basically free time to think about what I work on. This became the thing I wanted to work on. So I wrote it down. But then I was pretty careful, like, oh, it's the first idea. I can't fall in love with the first idea. You got to go through a bunch of ideas. So I did. I had a bunch of consumer ideas.

00:46:00 - Scot Wingo
Like I, I, what was a bad consumer idea you came up with?

00:46:03 - Todd Olson
You know, it's basically, I think the price.

00:46:05 - Scot Wingo
Car washing?

00:46:06 - Todd Olson
No, it's called neat. You know, it's like one of these, like I was just tired of all the paper I got as a parent. I was like, can we just like, like send it in Some scanner shouldn't like ocr. So I stream a lot of OCR technologies, blah, blah, blah. I mean, I think that problem is probably waiting for AI. I'm sure it's like way easier now, but, but then as I started exploring, I realized I don't know anything about consumer technology. I met with a VC who, he gave me incredibly good advice. He's like, Todd, you may not look at it this way, but if you look at the dollars invested in you or in companies that you worked at as an executive, there's probably at least 100, maybe more million dollars invested in companies you worked at or like you. And maybe not you personally, but some cases maybe. And that's an expensive education. Don't waste it. And he was right. He was right in that, you know, I am good at a certain thing and I've been educated in doing and it's like enterprise B2B tech. And I think knowing what you're good at and sort of like doubling down on that I think was a powerful reminder. And so that's when I kind of cut out all the consumer examples and really went hard. In Pando and I, they added another B2B idea which is around financial planning software, like budgeting software, which I actually don't know very little about. And actually although I am an independent board of a financial planning company, Dow, but at the time I was like, I don't know this space very well, but I mean, I don't think I would have created Anaplan then. But yeah, that was sort of the idea.

00:47:37 - Scot Wingo
Cool. Where did you start to get enough momentum where you got the co founders in and started selling them on it? And then, and at some point I want to understand where the name Pindo came from. I'd love to hear that story.

00:47:51 - Todd Olson
Yeah, well, look, the co founders I had, Eric Bodick pretty much lined up. He knew we wanted to work together again. He had to wrap up a few things. So that was early. Rahul decided pretty early to come in. So we started pitching investors then. This is before I really spent time with Eric Trone. And like the vision then was so be in my experience, I was pretty passionate on being the CEO. I just like, look I may be terrible at this job. That's fine. But I think I will have regrets if I don't try it. And I don't want to have regrets in this. I want to really love it. So I was kind of upfront with both Eric and Rahul. I was like, I really want to try this. I feel like I owe it to myself to try it. But I was also, amongst those three, the most technical. So for a while, I was going to be CEO and cto, which would have been very weird. And I think we sort of struggled to get, like, we had one investor, Core Capital, Will Dunbar, who was just here at our board meeting. So he's still coming to board meetings. You know, he said, I'll write a check for whatever you're doing. So I had one check.

00:48:51 - Scot Wingo
Boom.

00:48:51 - Todd Olson
Which was good.

00:48:52 - Scot Wingo
Nice.

00:48:52 - Todd Olson
But I had to fill out the round.

00:48:54 - Scot Wingo
Was he successful through the rally?

00:48:57 - Todd Olson
Yes.

00:48:57 - Scot Wingo
Okay. So he knew you. This wasn't just a random dude.

00:49:02 - Todd Olson
He's like, look, I like what you did there. Anything you do, I will write a check in for the seed round, which is helpful. I'm very helpful. And so I was like, great, thank you. And then I had to fill out the round. So I was talking to people to fill out the round, and we just weren't filling out the round. And it was like, anyway, meet Eric. Great coffee. Rahul and I and Eric. But we all kind of convinced him, okay, join this. Then the team looked like me as CEO, him as cto. And then we had Eric ran marketing for the bit, and Rahul has been our sort of chief operating, sort of like the ops person. Then it became pretty easy to raise, not easy to raise money, but we filled around pretty fast because Eric is very, very. I mean, look, he's an accomplished cto, but now you also have two people who are highly technical leading this company, which I think people liked that story.

00:49:50 - Scot Wingo
VCs don't often leave to just start a company. That's a signal that this must be pretty interesting.

00:49:56 - Todd Olson
Yeah. So I think that's how that happened. And then we did close out the seed round.

00:50:02 - Scot Wingo
This was 2014ish.

00:50:04 - Todd Olson
Yeah. We closed on December 23rd of 2013. But yes, we would say just January 1st is when we started the first HQ rally, actually, which is in the. What was the Brooks Bell space on Hillsborough Street.

00:50:17 - Scot Wingo
The Christmas round. Wow.

00:50:18 - Todd Olson
Yeah. So I won't forget that. But that's just like a million dollars, which now, like, everyone's like. Everyone's like, Whoa, you know, 4 million is a small Seed round. Well, we get a million. We do a lot with a million dollars. Pendo, the name coming to that is I'd always thought, again, going back to this continuation of my story, that the goal of Pendo was making sure people got value out of software. So I was like, what's the Latin word for value? It's pendo. So that's really where it came from. It was really as simple as that. Now we have come to learn since then that Pendo's also Swahili for love.

00:50:54 - Scot Wingo
Thank goodness that went your way.

00:50:55 - Todd Olson
Yeah, it went more.

00:50:56 - Scot Wingo
Sometimes you find out these things are not what you want them to be.

00:50:59 - Todd Olson
Sometimes you do.

00:50:59 - Scot Wingo
We've got a problem in this country. Okay.

00:51:02 - Todd Olson
Yeah. So you'll see us use Love a lot now in our marketing and branding. I think you're gonna see it more. We have a new cmo. He wants to bring it back more, but I think it's been kind of. Kind of fun.

00:51:12 - Scot Wingo
So one way of keeping track of this is you had cerebellum, which was kind of a. Not a win. I'll just use that language. Yep. A. I'm a relentless optimist, but like a pessimist would say, you failed there. Then you started Sixth Sense and that was kind of a failure in a way.

00:51:26 - Todd Olson
You can say that.

00:51:27 - Scot Wingo
Why do you keep going? Did that put a chip on your shoulder where you were like, yes, of course.

00:51:33 - Todd Olson
Because I believed that we should have wanted cerebellum and I don't think it was. Look, maybe I could have done a better job convincing the board that a 22 year old can negotiate a successful transaction, but definitely felt like it was sort of a little bit out of my control. Because look, we picked the investors, maybe that is in my control. We picked investors that weren't good partners and that's on me. And I was on Eric. So I think, yeah, massive chip on my shoulder. I still have a chip on my shoulder. I don't think it's going to leave anytime soon. So I.

00:52:03 - Scot Wingo
After 10 years and building this. We'll talk about this in a minute. But building something relatively large. You still there?

00:52:09 - Todd Olson
Oh, yeah. I feel like we have a lot to prove still. And I. No, I'm just as hungry as I've ever been. So I don't know why. Maybe I'm just wired this way as well. But no, I don't feel any level of success. So, like, not yet. Maybe I will one day, but I don't feel it today. And I just want to win and I. And you know yeah.

00:52:33 - Scot Wingo
Hearing your story, I feel like you've been painstakingly close a couple times and then just like, you know, yeah, something, something happened. Getting the bad board, CEO disagreement kind of thing, little misalignment. You didn't have the confidence to say I want to be CEO. Could have gone another, like. Yeah, yeah.

00:52:49 - Todd Olson
I just, I'm going to work as hard as I can and until I can and, and, and because if I don't do that, I'm always going to have this regret. What if I just tried a little harder? Or what if I did this? Or like, I don't want to have that feeling. I don't want to, I don't want to second guess myself later. What if I actually, why didn't I try to do this? Or like I, I just, you know, I think I like to say maybe I believe I'm sort of destined to do this or whatever you want to say. It sounds weird, but I love this, like, this job, this work, like high growth tech. I love it and I can't imagine doing anything else. So, yeah, I don't know.

00:53:26 - Scot Wingo
Cool. Our audience is mostly founders, so I'm asking Foundry questions because it's hard. Let's say there's a 22 year old watching this and they're where you were. It's kind of like heart. And let's say they have a failure. It's hard to keep going. Sometimes I find it motivating that you've been able to dust yourself off and get to where you are.

00:53:45 - Todd Olson
Yeah, I mean, look, chip in the shoulder is the term that we would use often because I'm like a little angry that we didn't have the success earlier in our life. And here's the other awesome byproduct of that today, which I didn't really appreciate until a few years ago, is to get so close and not get it. And so that gave me two things. One, to realize I can get close. If I can get close, I probably can get it. So the first thing it gave me is hopefully. But now as an older person, it gives me appreciation. Like plenty of people get in my job and like, oh my God, you run a 900 person company. Is it as fun as when it was? When you're running a five person company, Aren't you slow moving? Don't you hate all the meetings? I get that question all the time. And do I miss some of the easier times? Do I miss coding a little bit? Of course I miss coding. I love it. And do I love kind of the fun time Where I can just kind of like people weren't paying attention to literally everything I'm doing and micro analyzing it.

00:54:43 - Scot Wingo
Who's Todd on the phone with right now? Oh my God. What's it mean?

00:54:46 - Todd Olson
Of course I missed some of those days. But you know what? I really appreciate what we've built and I appreciate the fact we built a great company. And is it a perfect company? No, there's plenty of things we have to fix. But I appreciate the grass is not always greener. And I think so being old enough to have appreciation for knowing what you've got, I don't want to run out and start some new company. I think because I think we built a really great company and I like working here and I think it takes a lot of work to get to this point and I think we have a lot of building to go. I said this to our investors last night and I had two meetings this year with customers, potential customers, that were two of the best meetings that I've had in my life in terms of business meetings. I'm meeting with incredibly high ranking people at huge companies and we're talking about how we're partnering to like transform their business. And to say that 10 years in dependo, 11 years in and had like two of the best meetings of my life feels great. And when I did do it, one, I did a day trip to Hong Kong. A day trip. I literally flew to Hong Kong, had a one hour meeting and I flew home.

00:55:48 - Scot Wingo
Did you get back before you left?

00:55:51 - Todd Olson
Not quite, but close. I had the same crew. This is crazy. The same crew who took me to Hong Kong, took me home and they thought it was crazy. They had me there and back. They said, did you just come for one meeting? I was like, absolutely, I came for one meeting. But you know what? That meeting was the largest transaction we've had in history. Which closed actually pretty recently. That was not today's transaction. It was a little while ago, but this month.

00:56:15 - Scot Wingo
Congrats. That was a good meeting. Good meeting. That was worth it.

00:56:18 - Todd Olson
Good meeting. And then the next one, we'll see what it is. That's a few weeks ago. And it was in Japan, But a massive company, one that we've all heard of. Yeah, that jazzes me up, man. I love that. Do I love all the travel? No, but I love the experience, the meetings. And I know that, oh my gosh, if I'm having these meetings now 11 years in, what am I gonna have the next 11 years? We're just getting started. I had two. Are we gonna have 10 next year. I don't know, maybe that's the way these things work. We're just telling a story downstairs of the four minute mile. Before someone had broken a four minute mile, no one had done it. Then the next year, what, 13 people did it. Like Pendo. That's what it's like all the time. Once you do something, you realize we can do it again and then you're going to have it amplified the next time. And that's what I look forward to.

00:57:04 - Scot Wingo
Yeah.

00:57:04 - Todd Olson
Hitting a new goal.

00:57:05 - Scot Wingo
And at those meetings you learn how they're thinking about it and then you can reflect all that back into the marketing, the sales team.

00:57:11 - Todd Olson
Yeah, yeah.

00:57:12 - Scot Wingo
And I want to talk about that. This is going to be a weird interview because you probably spend 95% of your time talking about Pindo. But I actually want to. I think that's like really well covered ground. So I kind of like want to just flash forward, like. So then we'll skip 10 years. So you start Pindo.

00:57:25 - Todd Olson
Yep.

00:57:27 - Scot Wingo
10 years later, 11 years later, you know, to the extent you can talk about it. And I covered some of it in that article. But like, you know, so you've mentioned 900 people. We're sitting in your building here. You know, you got like what, four, six floors here? Some, some. Yeah, five, five, five, five floors. You know, you, you've obviously, you know, just making it this long is impressive, but you've got a very large revenue scale, obviously, to have that many people. You know what else, you know, what are some other highlights? And then give us a very quick Pindo update.

00:57:59 - Todd Olson
Look, I mean, I'm not gonna lie, these were tough years. I mean, like a lot of people, like 2021 was a gold rush of IPOs. Tech IPOs, specifically, one of the largest years in history. And then we went to like nothing like a tech IPO oasis.

00:58:18 - Scot Wingo
But then to get to 21, you had to survive Covid, which is hard.

00:58:22 - Todd Olson
Correct. But we would been a company that you would have thought would have gone public in 2022. And then obviously with the macroeconomic changes, the end of zero interest rate period, then it got hard for companies to raise capital, which we actually had enough capital. So it didn't necessarily affect us, but it affected our customers, the companies we're selling to. So then that affects some of your growth rates then because we're worried a little bit about the capital market environment and raising capital. We need to get efficient fast. I think we, our team. Kudos to my team. They did an excellent job very early. So like I would say January, Maybe February of 2022, we put a hiring freeze on this actually really helped the business. Doesn't feel good to do that. But for a company that had been, like, growing their headcount, like, the previous year, we doubled our headcount. Go from doubling your headcount to a headcount freeze is crazy. Shift in, like, momentum. But you gotta credit our teams. Like, there was no, like, hey, Todd, why are we doing this? Or they got on board fast. We started doing things like introducing AR per employee, which is an efficiency metric. We had to educate the company what efficiency was because it was all about high growth. But we did that that year. So 2022 was a year of, like, shifting the culture. And then in 2023, we drove that efficiency. So we ended and we announced this already, like, and in 2023, generating cash for the first time in a quarter, which to go from burning, like, a lot of money to generating cash is a crazy transformation. Essentially, under two years, a lot of companies haven't been unable to do that. And we did it. So I'm very proud of that. But that came at a cost. We ran a lot of experiments. Obviously, our growth rate was hindered by this. And as you know, to take a company public, you need to be growing at a certain pace. So this year's a year of acceleration. And, you know, I'm. And we said this at the end of this day, and I've said before, we are accelerating. And guess what, folks? Accelerating a company of our size and scale is hard. It's just hard. It's hard doing it when you're small, but it's really hard doing it our size. So we're feeling that now. It's work. I'm working as hard this year. I'm traveling more than probably any year in the company history. We're 11 years in. So, look, if you think of your entrepreneur, things get easier. They may not. Like, did I forecast, like, zero interest rates going away? No, I don't think I did. I don't think many people did, to be quite honest. But look, I think we're doing a really good job.

01:00:43 - Scot Wingo
Did you forecast M and A being totally locked up?

01:00:45 - Todd Olson
Did not do that. I did not forecast the Federal Trade Commission blocking every deal. So there's a lot of things I didn't forecast. But you do the best you can. And I think our team's doing a really, really good job. And part of it's because I still believe and the market's massive. You have to believe is your tam Is your total addressable market huge? Ours is huge. It's unlimited. We tell basically everyone who uses software. That's everyone. And we're seeing that we're closing. Really interesting company logos, some of which I can talk about, some of which I can't, but across everything, like, United Airlines came to pandemonium and talked about how we helped their pilots navigate the crowdstrike outage. When I started Pendo, I don't think I thought that United Airlines were buying us to do really anything, but it feels good. And then you realize, oh, my gosh, if one airline can buy us, all of them can buy you. So now we have four or five airlines that we're talking to right now.

01:01:37 - Scot Wingo
And if a fortune. If you can get a little chunk of the Fortune 500, why can't you get all of it?

01:01:42 - Todd Olson
Yeah. So I think, wow, I feel like.

01:01:45 - Scot Wingo
Your TAM has really expanded. Like, you started and there was like, you know, there's these little pools of developers at companies building stuff. And then, you know, now everything's so digital. Your timing was perfect this time where you got in right at the right time. It wasn't too early. You kind of Goldilocks that. But then it's, you know, your TAM has expanded very dramatically lately. So, you know, go to any organization like, you know, Verizon or American Airlines, or, you know, pick any kind of operating business. They've got software everywhere, they've got PMs, it's all over the place. They need to standardize on this stuff. So I can imagine you probably have got these little balkanized deals and you get like a little department over here and then suddenly you're starting to talk about these like, like, let's go do a company wide standardize on this thing.

01:02:29 - Todd Olson
That's exactly what it is. And, and also it's actually challenging. It's not. It's not as cookie cutter and easy. Like, all these use cases are a little bit unique, so it's not all over. So, like, it. It is. Working at Pendo, it's hard. I mean, it's not an easy job.

01:02:43 - Scot Wingo
I mean, well, then suddenly like, you know, I'm just going to pick like a random telecom signs up for a big deal and they expect it to work a certain way. And like, you know, the software was designed for smaller teams and you've got to like, you know, the CEOs gonna wanna see a view and this. So there's. With all these deals comes a whole nother turn of the crank. Yeah.

01:02:59 - Todd Olson
And you look at other things like you'll see this in the analyst day is what we talked about. We also went from basically one product company to a multi product company. And now you gotta teach sales reps how to sell multiple products and you have to do land and expand deals for multiple products. That new product motion is a whole new motion. Then we have to build the operational controls because Wall street wants to know how many customers have two or more products, three or more products, four or more products. So like these are all things we had never built. So we built all that and now we're doing international markets, which is a good amount of work. And then of course, last but not least, now we have AI, which AI is set to be on par with cloud, mobile, you name in terms of large technology shifts. So now we're having conversations around innovators dilemma and how we navigate it ourselves. We have a large revenue stream, we have to take care of customers and we have to innovate in what the world's going to look like. We're having meetings where like, hey, if I was building Pendo today, I'm a startup trying to disrupt us. What would that look like and how do we build that thing? Because that thing could be the thing that disrupts us in a few years. But we don't want to let that happen. We want to be the ones disrupting ourselves. So how do we do that?

01:04:05 - Scot Wingo
I had the other argument, so someone came. So I actually had a discussion about this and everyone's like, oh my God, what's Pindo going to do about AI? Everyone's just going to roll their own Pindo. It's like, I don't, I don't think so. I actually think it's awesome for you guys because now everyone's coding. So like you went from, you know, these little people that learned how to code, then it went into all the company, everything had to be digital. Now everyone's generating scads of code. It's going to be really bad code, it's going to be all over the place, it's going to be off target and they're going to need more Pindo. So I kind of view it almost like I see your argument and you should definitely be paranoid, but I actually net out that it's pretty positive for you guys because the amount of products that are going to be kind of coming out faster and faster, the stuff you guys nail and make sure works is going to be that much more important.

01:04:49 - Todd Olson
Yeah, actually that was.

01:04:51 - Scot Wingo
It's going to be a signal noise problem that you're going to be the solution to. Yeah, I don't think it's ever existed.

01:04:56 - Todd Olson
That's. To me, I do think one of our big bets is that is what we're seeing today. If you believe one of the big constraints in the economy has been the number of software developers and AI attacks, that constraints, then we're going to see just a heck of a lot more software. And if you see a lot more software, yeah, there's going to be a bell curve of software. Something's going to be great, something's going to be terrible. And Pendo's hopefully the decision point for what's good and what's bad and how do we make it better.

01:05:22 - Scot Wingo
So, yeah, it'll go through a gardener adoption. There's going to be this moonshot of software code being generated and then it's going to go into the trough of disillusionment and then people are going to be like, whoa, we wrote all this code. That was terrible. What are we doing?

01:05:33 - Todd Olson
Yeah. And people are already using us to help their users understand how to use the new AI and how to provide qualitative feedback. So I think there are a lot of. I think, yeah, I'm also a tech optimist, but I believe that it's only going to help our business. But I have to as well put on my disruptor hat and make sure that we handle that use case as well. But I think ultimately it's going to be good for Pendo, but it's big and it's transformational and, yeah, it's very interesting times.

01:06:02 - Scot Wingo
Another way of looking at AI is the golden dust. Slash gold nuggets is the data. You guys have to have the most user data. What if, like, why can't you have a Pendo AI that is the best at generating code because it knows the user data. And that's.

01:06:18 - Todd Olson
So that's where I think that, to me, is what the potential unlock that we're looking at is like, how do we take our data and put it in a form usable for AI? Because, like, we know, like, if you're trying to build an agent, we know everything someone does inside of an app application. So, yeah, you know where to put.

01:06:33 - Scot Wingo
The button, you know, the color, you know, don't do this flow, do this flow. If you do a scrolly thing, people won't know, you know, all that.

01:06:43 - Todd Olson
Yeah. So I think it's, honestly, it's super exciting time. But so where we are today, like, you know, I'm building, I want to build. Like, I was just with our product team before this. I'm getting more involved. I'm getting involved in AI initiatives. I think if anything, you know, if you look at the last few years where I've been spending most of my time building out, go to market. I've been shifting my focus recently to focus much more on product. And, you know, I have a thing and I think it's maybe been reported on before, but I move my desk based on, you know, whatever, wherever I feel like my attention is needed. And I was on sales floor 18 here for a long time, years. And I just moved to product. I moved from 16 probably about three or four months ago. I just felt like I needed to be closer to what was going on down there. And I think it's been a good move and I think I'll be there for a while. I think it's the place to be. I think I'm a natural builder and I think we've got new sales leadership. I think they're executing well. I think. Yeah, I feel good about where that department's moving and it's time for me to get back to building.

01:07:47 - Scot Wingo
So there's a lot of talk. There's a couple things. So there's Founder Mode. I kind of find that a little bit boring. I don't know if you want to. So this all blew up. I don't know if you.

01:07:55 - Todd Olson
I'm well aware of Founder Mode.

01:07:57 - Scot Wingo
I don't know what you see.

01:07:59 - Todd Olson
Happy.

01:08:00 - Scot Wingo
The chesky thing kind of blew up.

01:08:01 - Todd Olson
Look, I. There are parts of Founder mode which I think are really important lessons from this. And it did hit me a little bit because a lot. Because of what was happening here at Pendo and how I was feeling internally. I think, look, I think you come out of COVID you have this whole hybrid work thing. One of the things that's been most stressful about the COVID thing is in office culture piece. And if you knew Pendo pre Covid, if you walked in our office in Raleigh, you just felt the culture. And during COVID everything was great. But then eventually we sort of lost that.

01:08:40 - Scot Wingo
It kind of culminates around the office, and it's been hard to get that back post Covid for everyone.

01:08:44 - Todd Olson
Honestly, it was kind of making me sad and despondent. If I'm thinking about what keeps Todd engaged at Pendo for the long term, why do I want to come to work every day? I want to engage with amazing people. At the end of the day, if this culture changes into something that I don't want to work at, that's probably bad. For the company. What I realized it was moving in a direction that I didn't like. Now when I was asking people for advice, they're like, oh no, but be careful. People are sensitive. This is a very hot topic. It's loaded. When we do surveys, this is what it says. And I was like, you know what? I actually don't care. But it took courage for me to say, you know what? Screw it. No, we're going back and we're mandating it. And this is just the way it's going to be. Because at this culture, ultimately, because in place I don't want to work out, that is probably worse than the handful of people that want to come back to the office. And I think I started not listening to people, which is a. And I listen to plenty of people, folks. So, like, don't. But I think getting the courage as a founder to say this has to change has been something that's been near and dear to me. We just changed our core values. We're a big values driven organization. We just changed them. Last time we changed our core values with this whole committee, we took six months. This time, three founders got in a room and said, these are our values.

01:10:08 - Scot Wingo
Founder mode, hashtag foundermode.

01:10:10 - Todd Olson
Yeah. So the question is, why do we do that? It's just a feeling like things had gotten off course.

01:10:17 - Scot Wingo
Well, if you ask a committee to design a horse, you come out with a camel. It's very hard for a committee to decide the direction of a guy.

01:10:24 - Todd Olson
We just had gone a direction that I felt like it didn't look and feel like the pendo that I knew. And there's this classic Andy Grove quote from the intel days. And intel of course, making the news because for their bungling for the past few years. But Andy Grove says this. What would our success when our successors walk in this room and take over this company? What would they do differently? And I was looking at our values. I was complaining about a few things at the company, complaining about a few things. I started thinking, I can fix this. I can fix this. I don't have to wait for my replacement to come in. I can just be that person and just make this change. I can be unafraid to change our values and if I want to change them, I can change them. But I think I and I actually came to this, like, by the way, this awareness on my own before I read founder mode. But the founder mode came out right around the same time. So somehow it all got attached to it in people's minds that somehow I read Some podcasts. And, like, I decided this. Truth is, I did come to this realization on my own, and I do most of my thinking on long runs. So I was on a run, and I was like, hold on. Actually, I could change this. And very, very, very invigorating for me. And. But having the courage to change your values when, like, I mean, if you look at our engagement surveys, I mean, they're high. Like, we're growing. Like. Like, this is not. Like, the company's not broken. I just know it can be better. I know in my heart it can be better.

01:11:49 - Scot Wingo
And you as a founder, it's like.

01:11:50 - Todd Olson
I feel like I had to change it. I feel like my replacement would change it. So, like, why am I not doing that? So. So these are the things I think about in my head. And so we rolled that out, and I think I was a little controversial, some pieces of it. But I think, by and large, it's been really positive. And the company's like, I got really positive responses from a bunch of people. They kind of feel fired up that we're getting more involved. So. Yeah, I think the concept of founder mode isn't a horrible one. Some people have abused it, I'm sure, but people abuse everything. Yeah.

01:12:20 - Scot Wingo
I think Chesky does a good job of explaining. It's not micromanaging. It's staying involved. Like you moving to the 16th floor to be involved in product. That's, you know, that's not you micromanaging. That's you realizing there's a point in time here with the world changing. That that's the most important thing.

01:12:35 - Todd Olson
Exactly.

01:12:35 - Scot Wingo
You're not going to micromanage, but you need to have your finger on that, or else this AI thing, you know, may pass you by. It may disrupt you. So, yeah, I don't. I don't think of it as that micromanagement kind of thing.

01:12:46 - Todd Olson
Yeah, I struggle with word micromanage. I struggle with the word. Like, if you see someone at your company doing, like, the wrong thing, like, do you stop it or you let them do it? Is that micromanaging? I don't know. I feel like it's good coaching, you know, like, hey, that's the wrong thing. You know, some people make bad decisions, you know, that's okay.

01:13:04 - Scot Wingo
Well, it's presented as this binary or, like, either nice or an A hole, and there's actually a middle one where you're like, you know, hey, I. I know you were on this sales call and you said this, but, you know, I want to. That's, like, not how we, we don't promise stuff to the customer we can't deliver or you've got to inject yourself there. You don't have to be, you know, you're not like, you're fired. Now some, you know, like a jobs or an Elon kind of do that, but that's just right. But they do.

01:13:26 - Todd Olson
Yeah. I joked with people all the time. Have I ever just walked in and fired someone? Because like, no, like my time's a teach and coach is like, like, yeah.

01:13:34 - Scot Wingo
Now if you've coached them twice and you're on your third one, you're like, nah, I'm not really sure getting this.

01:13:38 - Todd Olson
It's still not usually me doing the fire someone else. But I mean like suggest to that person, hey, you should look at this. But yeah, what's going on over here?

01:13:44 - Scot Wingo
Yeah, so you know, a couple founder lessons. So you've talked about transparency. You guys have an amazing culture. There's a lot online that you do. So we have that. The other thing I've noticed, I didn't get to go to Pandominium, but I knew several folks that went, your customers are like crazy passionate about you guys. Like, what do you, what's the secret sauce of that? Like, how do you get such engaged? Like, so how many people did you have? This is your trade show you have every year. Yeah.

01:14:13 - Todd Olson
Pandemonium at 1200, 12, 1400 customers somewhere in that range. I mean with pen Dozers, it like adds like another 400 people. So it's like practically 2000 people. And yeah, it's like we call it a product festival. It's tree like a festival. It's indoor, outdoor, like it's one of my, I mean, if not my favorite week, there's two great weeks of the year, company kickoff. So we do get the entire company together in Raleigh in February. I mean, it's an amazing time. That feels great. And then Pandemonium, those two weeks, amazing weeks. They're always here. Yeah. Look, question is, you know, it really starts back at MB&A. One of MB&A's, like mottos, think of yourself as a customer. To back that up, they had this concept of two ring pickup where you have to pick up the call within two rings, which is back when they sell phones and like rings. But I used to watch people, like grown people, and I was again 14, 15 years old, dive across the desk because their bonus is like they measured every phone in the entire company and they did a 98, 99% rating. And if you hit this, you got a quarterly bonus that was pretty sizable. So people would dive across desks to get this thing. Yep.

01:15:21 - Scot Wingo
Incentives and measure what you care about.

01:15:23 - Todd Olson
And so then you realize, wow, this company cares about customers. That really, really hit me now. I didn't really get a chance to scratch that itch. You know, I wasn't. I didn't set the values at cerebellum. We didn't do it, although we had really good values there. But then at 6 cents, we didn't really have values the way I would have wanted to. So when we started Pendo, I was like, I want values and I want customer to be a top value. And we talked about what that meant and what I expected. I said, we're going to do crazy things for customers. We're going to make it so they love us. And that means getting an engineer on the phone. We're going to hire engineers and get on the phone. Plenty of people don't, like. There are people that I've worked with, engineers, great engineers, who like, no, I don't want to talk to anyone. I'm not going to be my cube. We don't hire those people here. We hire people that if we have to, we will put them on the phone. So that's been part of our, like, what's different about us since sort of day one. But we will do extreme things for customers to make them successful because we really, really care. And I think that when you read our Series A, like when we did our Series A, you're like, where does this company come from? But it's because references. They kept hearing about us from other people because we took care of customers.

01:16:32 - Scot Wingo
And their portfolio, their portfolio companies. Like, yeah, we love this Pindo product. Like, what is this Pindo product?

01:16:37 - Todd Olson
Ever since that was the magic in, like, Series A, Series B, Series C. You can read all these decks. Like, I mean, they said wonderful things, not just about our product, but about our team. And you go to Pendo here, great product, great team, great event. Those are like the three things you hear. So it feels really, really good. I think we hire people that really, genuinely care about customers that want to make them successful, and we will almost always do the right thing by them. I think it's a core value, so I think it's something that we really care about. We have an NPS channel that some people don't like. Nps, whatever. But I like it.

01:17:14 - Scot Wingo
But it's really deterministic.

01:17:15 - Todd Olson
And when you get this is where it's valuable. The number is valuable, but the values I got, we take action on it someone gives us like a 6 or 7, anything less than a 9 or 10, we're probably going to get on the phone with that customer and talk to them. We take that feedback incredibly seriously. I get on the phone with these people and by the way, they're a little shocked that I'm reading them and getting on the phone. That's when they know, like, okay, this company must care. If the CEO of a company this size is getting on the phone with a 20k deal or whatever. And I will. I have answered support tickets. I've answered support tickets on weekends, even recently in the last few years.

01:17:52 - Scot Wingo
It's not only the customer, it sends a message to everyone in this building. If we get a low nps, Todd's going to call them. If I'm the account manager on that, we care. I don't want that to be the first time they've heard from someone at Pindo in a while. But it also shows that you're very passionate about this. And part of leading is leading by example. You can set up all these things, but the best way to illustrate them is to do it exactly and live the value set up for exactly.

01:18:21 - Todd Olson
No one is too big in this company to do the hard work, like getting on the phone and apologizing to a customer. Getting on a phone or fixing it, working day and night. I think we think we put ourselves in our customer's shoes a lot. I think we've done a really good job of that throughout the years. And I think that's what engenders this sort of, like, love for the business. And I think we gotta keep that magic. And that's one of the things, as a founder, you always think, how do I keep the magic? Part of my job is holding on to what's great about our culture, but knowing we have to change some things because we're getting much bigger. And you gotta balance both those things out. But I love that part. The board joked, because there's a thing, it's on LinkedIn. And there was a customer who really liked my jacket that I was wearing at Pandemonium, and she asked, I really like your jacket. I just gave her the jacket off my back, which she was excited about, and it was awesome. It was honestly, a great.

01:19:17 - Scot Wingo
Wasn't a sports coat, it was a Pinto jacket.

01:19:20 - Todd Olson
It was like a vintage one or OG jacket. You can't get several years back, something like that. But it was a cool jacket. But look, awesome. She's probably going to be a Pendo fan for a long time because that is a cool experience, and that's a great customer for us. So that was.

01:19:35 - Scot Wingo
You can figure out how to make a retro line of pindo swag?

01:19:38 - Todd Olson
We probably can. Yeah.

01:19:39 - Scot Wingo
I have faith in you.

01:19:41 - Todd Olson
Yeah. But, like, this is the kind of stuff where I think we. We like to go above and beyond and. Yeah, it's part of who we are. It's not just a tagline.

01:19:53 - Scot Wingo
So do you still interview everyone that gets her?

01:19:56 - Todd Olson
I do not interview everyone. When jr who now runs the people team for us, when she came in originally as head of recruiting, that was like the. We came up with an agreement on when I interview, when I don't. So I do not interview everyone. I do approve every offer, though, and I have rejected offers, like, at the approval stage, which I think gets people's attention when it gets rejected. But we'll have conversations around certain things. I do read every scorecard. If I don't like the way the scorecards are written, I'll have them rewritten without specifics.

01:20:28 - Scot Wingo
Like, what would cause you to reject something? Like, you just don't feel like the bar is high. Like, Amazon has this concept of bar raises.

01:20:33 - Todd Olson
I know.

01:20:34 - Scot Wingo
Is it like a. You don't feel like the bar is high enough on that one?

01:20:38 - Todd Olson
I don't think the bar is high enough. Sometimes you'll see in the actual notes, hey, this person didn't do great on this technical assignment. You'll see another persons about their technical thing, and then somehow it still skates by and comes to me for approval. And I'm like, I'm telling people, between the hiring manager and me, because there's several execs. Did you miss this?

01:20:59 - Scot Wingo
I see six yellow flags here and a little pink one.

01:21:01 - Todd Olson
What is going on? Like, whoops, this one. You know, some people just get into the habit of clicking the approve button and they're not reading it to the.

01:21:07 - Scot Wingo
Level that we really want to feel this wreck and it's been open for.

01:21:11 - Todd Olson
So they know I read every single thing. So now they pay attention to every single thing. And that's how you build habits. Like, I think. Yeah. I mean, you can probably tell that's how I do. Like, I do the MPS thing this way. I do the. The scorecards this way. If you get these fundamentals right in your company. So many other things work when you have happy customers. Yeah, it's easier to sell to them when you have great employees. Yeah, it's easier to hit your goals. I'm a first principles thinker. If I get the basics right, the rest is a Lot easier. I don't sit around in my office and come up with strategy. I could. That's not really going to help the company. Yes, there are signs. I have to think strategically.

01:21:55 - Scot Wingo
But I think if you're gonna shoot a rocket to the moon, physics is your first principle. But for businesses like ours, it's customer is the first principle. I always like, whenever I'm lost, I'm like, I've got to talk to customers. That's always my North Star. And I feel like you obviously do that too.

01:22:09 - Todd Olson
And look, as I tell the company every time, and as I learned this from the togethersoft days, we are a software company. We have two jobs. We manufacture software and we sell it. If you are not manufacturing it or selling it, you're helping someone who is, period. That is your job, to help someone who is doing one of those two things. So we remind people. For a while when we were a tiny startup, I focused mostly on those two levers. How many engineers do you have? How many salespeople do you have? And everything in the middle is sort of squishing and as few as possible. It's generally the rule. But now we have a bunch more people. But yeah, interesting last question.

01:22:45 - Scot Wingo
If what, let's say a founder comes up to you, what kind of words of wisdom do you have for founders these days? You've been at this for quite a while now, this founder gig. Yeah, I mean, geez, we've hit on some of them. The transparency, how you do, the culture, anything else that you can think that you haven't heard.

01:23:02 - Todd Olson
I think we didn't talk about it because maybe I talked about already, but product market fit is a good thing. You probably heard my first two startups did not get the product market fit. The one difference. The one difference, really you could say probably more than one, but is we obsessed over product market fit early. We didn't rush things, we didn't rush it. We got to product market fit. So don't rush it. Get to product market fit. We picked really good investors as well. It's probably a second thing.

01:23:27 - Scot Wingo
How'd you know you were at product market Fit? Like what was the signal that you said, I think we're there.

01:23:32 - Todd Olson
Do you remember there was an exact moment at first, there was an exact moment, there was one actually later, which was pretty funny. But look, I think we were like, we went from like almost nothing to a million dollars in ARR in like a very short amount of time. Like it was pretty clear by like mid year that year that something was good. Was happening.

01:23:54 - Scot Wingo
We're onto something.

01:23:55 - Todd Olson
Yeah, but I wouldn't. I probably still, because I have a chip on my shoulder, probably still wouldn't have declared me having product market fit at that point. It was really funny. Years later, I would say, I think it was just coming out of COVID Yeah, we were just getting together, the board. I was in New York City at a board dinner, and I was talking about how. Because remember after Covid, like, we had a nice acceleration in the market and we had this, like, startup team and they were doing like same day closes, and we were a premium product. Like, they like, talk to a. Like they cold call someone, they get them on the phone, they sell them that day. And I was mentioning this to. We had a number of them then and I mentioned it to our board. And like Todd, that's called exceptional product market fit. It's what it's called, like when you do a same day close and I product that's like 12,000, $20,000. You just have exceptional product market.

01:24:42 - Scot Wingo
You're over the target. Yes. Yeah.

01:24:43 - Todd Olson
So I was like, okay, I guess you're right. We probably do have really good credit. You know, at that point then it really hit me how good it was because I hadn't thought about it then. So this is. That. That feels good. So that's a piece. And then. Yeah, I think. And I give this advice sometimes, but when it comes to, like, raising capital or not raising capital, one of the things I see young entrepreneurs, to me, worry far more about is like, the size of the slice of the pie versus the size of the over pie. Hopefully, if anything you're getting from the Pendo story is that I want to grow a massive pie, and that's winning for me. And my slice will be fine. Don't worry about me. But I am going to literally not stop until I can build the biggest pie possible. And if I do that, a lot of people win. And that actually motivates me more than like, oh, well, I gave up this much in this round for this. Oh, my gosh, that's like scarcity thinking. I don't have scarcity thinking. I want to have more expansive thinking. So that permeates how I basically approach nearly every problem. Like, I want to create a massive pie. And so I'm always trying to think bigger and push boundaries. So that's probably a big piece that I'd encourage as an entrepreneur. And then the other thing I'm seeing now in 2024, that I didn't see my cohort of startups that Started around the time Pendo like a lot of the CEOs are becoming exec chairpersons or leaving or retired or being asked to leave. So that's kind of a weird thing I'm going through and like a lot of peers, like good friends, good peers, great companies and I'm talking to a bunch of them like what happened? Or how are you feeling? And people are tired. I mean like these last two years have been hard. We went from like go go days to non go go days.

01:26:28 - Scot Wingo
And I think pretty spright on me.

01:26:30 - Todd Olson
I feel great. I feel great.

01:26:32 - Scot Wingo
How long is your board meeting? Like three hours, five hours.

01:26:34 - Todd Olson
Yeah, I actually feel great. You know, I don't know how I feel great but I do feel great and I'm fortunate. And maybe there's maybe it's the chip, maybe it's something else, maybe something's like giving me this energy. But it is an interesting time in my career when I'm seeing a lot of my peers and there's going to be a next generation. And so it's interesting navigating all that personally and reflecting on it. You know, I'm being, I'm meeting new people that because my generation's. Some of them retiring which is kind of an odd thing.

01:27:04 - Scot Wingo
So I'll solve it. Don't do it as boring. You just like every quarter you get to see the business and you're just like wow, I wish I was doing it. Just keep building. Yeah, keep building, Todd.

01:27:13 - Todd Olson
I love what I do.

01:27:15 - Scot Wingo
That's what's energizing. You're building. Your building is amazingly fun.

01:27:19 - Todd Olson
Yeah. And I work with great people, you know and I was just about the board stuff and the invent. We just have a really good group of people. I genuinely like them. Like last time we took them to Hurricanes game by the way everyone had the most fun. They won by the way. Kudos. Kanes fun game. It's fun. It was interactive. It was really, really nice. I still like Neeraj from Battery invested in 2015. It's just great to some of the management teams like he and Rob Border he invested in 17. They've seen everything. They know this company very well and just like really supportive good people. And I'm very fortunate because I don't have drama for my board. I mean, gee, it's hard enough doing this stuff without that you have that. I do feel bad for founders that have that. So pick wisely. Get good people. Focus less on the prestige of prestige of the firm and your post money valuation and focus a lot more on are these really good human beings you're gonna want to hang out on meetings with when things go tough for 10 years, you'll have something tough happen in those 10 years. And like going for the premium valuation or going for like the top tier firm name because you want to say you raised money from abc, cool for you. But I am totally comfortable just making sure that good people are investing in us and I like working with them and they're good partners on me on this journey. And that to me is more important. And I think that's how I've run it. I think that feels like the right answer. But yeah, yeah.

01:28:51 - Scot Wingo
Thanks for time. Thanks for letting us go over. We appreciate it. You know, I know I'll be personally cheering for you to get up on the podium there, so thank you. I'm going to be 100% behind that, so hopefully you get there soon.

01:29:04 - Todd Olson
Appreciate it. Thanks.

01:29:04 - Scot Wingo
Thanks, Todd.

01:29:10 - Todd Olson
For more Tweener content, check out the Triangle Tweener time substack@tweener.substack.com for more tweener.

01:29:19 - Scot Wingo
Content, check out tweenertimes.com thanks for listening and we'll see you again soon on Triangle tweenertalks.