Here’s what you should know about Rick:

• Born in Raleigh, NC and grew up in Morganton and Charlotte, NC
• Went to college at Duke University
• Majored in Economics and Computer Science
• Wrestled at Duke
• Moved to Park City to Ski bum in after graduation
• Met Tyler at a startup called Zane Benefits (which is now part of PeopleKeep) in 2007
• Became the President of Zane Benefits after a mass layoff in 2008
• Bootstrapped Zane Benefits to $4+ million in annual revenue in 2013/2014
• After a regulatory threat in 2013, launched a new business called PeopleKeep
  • Raised ~$3M in venture capital to finance this
• Wrote a book in 2014 which was published by Wiley
• Merged Zane Benefits with PeopleKeep after confirming the legality of PeopleKeep’s approach and reaching product market fit in 2018. Milestones included:
  • $120K in monthly recurring revenue (MRR)
  • Profitable unit economics
  • 50+ user NPS
  • Low churn for very small business segment
  • Numerous customer growth and product expansion opportunities
• Was fired by the board in October 2018 when unable to align on long term compensation
• Founded LegUp Ventures in May 2019, which owns and operates companies that empower underdogs. Current ventures include:
  • GroupCurrent, which helps member-based groups reach sustainability
  • RickLindquist.com, where Rick writes and consults on various topics
  • Startup to Last, this podcast
• Likes:
  • Physical fitness
  • Continuous improvement
  • Sustainability (i.e. balance)
• Dislikes:
  • Bullies
  • Victim playing
  • Intellectual laziness

Entrepreneurial beginnings

Tyler: Can you just kind of give a little background on how you got into the startup space, entrepreneurship in general?

Rick: Well, I guess I do kind of have that story of always being a little entrepreneurial. I had lemonade stands.

Tyler: You did? At what age was your very first venture?

Rick: Four or five. Yeah, I did the lemonade stands. I took it very seriously. I mowed grass. I tried a lot of different things. I always thought about it. I read business books when I was in high school, entrepreneurial books. I always knew that was what I wanted to do, but I didn't know what my path was. I thought it was something that ... The story I like to tell is, my dad is a lawyer, which is kind of a sole proprietorship in a way. You're a partner in a law firm and you do actually have to produce for yourself. And then my grandfather owned an ACE Hardware store, True Value Hardware store. So I witnessed a lot of entrepreneurship growing up, but my dad always hated his job. He's a litigator and he always had to fight with people for a living. So I was really scared to go to start working because I thought I'd hate my life. I thought that's what everyone did. So I was born in North Carolina. My parents got a divorce at a young age. So I moved all around North Carolina. I think I lived in, like, 17 different houses. I never had that one house. In fact, living in Utah, the Park City area, that's the longest time I've ever lived anywhere. 

College and major

Rick: And so anyway, I ended up going to Duke for college. I graduated in 2007 and had no idea what I wanted to do.

Tyler: Well, let me stop you for a second. So what did you major in?

Rick: Economics and computer science.

Tyler: So you had an entrepreneurial spirit before college. Did that inform what you majored in or anything like that?

Rick: Yeah. One thing that I think you'll learn about me is, I'm generally open to anything but, once I form an opinion about it, I form a pretty strong opinion about it. So I actually did not declare a major until the end of sophomore year. I took just about every 101 course at Duke, including political science and I dropped that class midway through and had a really big blowup with the professor. I hate political science classes. They're too political.

Tyler: Who would've thought?

Rick: Yeah. Who would've thought? So I knew that I was interested in economics. I knew that I was interested in computer science. So those were my first two if I had declared freshman year, but I wanted to see what was out there. And then they were the most practical. One was learning about how money works and the other ... and people work and markets work, and the other was how to build things, I thought. And then I realized, computer science is actually a bunch of theory and bullshit. And I think I had two programming classes and they were my favorite classes at Duke.

Tyler: Yeah. I mean, all college professors are theorists, right? So in a sense, every major is theory.

Rick: Yeah.

Tyler: Anyway.

Rick: Yeah. So I did a lot in college. I wrestled. I was in a frat. It was an atypical frat, but still a frat. I did student government. I did a lot of different stuff. By the time I graduated, I was pretty burnt out and so I remember everyone just doing investment banking interviews and I went through a couple of those and I was like, "I cannot do this. I could not move to New York and work with these guys. I need a break." So I decided to move out to Park City to ski bum. Called my dad. He basically said, "That's cool, as long as you're off the payroll." I think he gave me until July to move out and I basically just came out here expecting to ski bum. Unlike you, who came for a job.

Ski bumming to startup

Tyler: A job. I never heard of Park City, nor had I ever skied before. But you knew what you wanted to do here.

Rick: Yeah. So my grandfather bought a condo out of bankruptcy in the '80s with an ownership group. So we always came out here for a week to ski. So I was very familiar with the area and I always heard my dad and my grandfather and people talking, like, "I wish I had taken a year off to go ski bumming." So I called them out on that and I took advantage of it. But I got out here, I'd carpet clean in the mornings for a carpet cleaning company locally and then I was a bellman at a hotel called Park City Hotel. And then sometime in November ... I got here in July, and sometime maybe in November that year, I met a headhunter who was recruiting for this startup called Zane Benefits. They had just raised a $3 million series A. And I was driving this person around or it was something like, "What are you doing? You have a Duke degree and you're carpet cleaning and driving people around?" I said, "Yeah. I'm serious about ski bumming." So anyway, I ended up taking a job there because I got really interested in the problem. And I came on as an entry level sales rep and that was my first professional, what I would call my first professional job.

Tyler: Because you didn't do internships or anything like that, right?

Rick: My internship ... So one summer,...