Startup to Last

This week we're mixing the format up a bit. Instead of doing a deep dive on a specific topic, Tyler interviews Rick to learn about how he went from an entry level salesperson to the CEO of a startup that grew to over 50 employees, and what he's doing now to start his next venture.

Show Notes

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
    •, 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, I went to Poland to wrestle with the Olympic team. That was cool. One summer I worked in a factory where I had to wear a clean suit and basically got minimum wage first shift. So I did internships, but they were different.

Tyler: Yeah, not like the knowledge-worker stuff.

Zane Benefits

Rick: Yeah, not knowledge-worker. Exactly. So anyway, I joined the company. When I interviewed, the founder was running the company and there was a COO. And when I actually started, it was a month and a half in between that, the founder had been fired, replaced, and the COO had exited, as well. I don't know exactly what happened and no one told me. So I show up and there's a new CEO, there's a new management team. And I just started working. It ended up being the best decision of my life because I got to see this startup unfold under a venture capital scenario. As you mentioned in your interview …

Tyler: Yeah, I'm assuming we put mine out before yours.

Rick: Yeah.

Tyler: Yeah, since we both worked at Zane Benefits, there's a little overlap here. But why don't we rehash it again?

Rick: Yeah. So the company, in 2007, raised $3 million in July or so. And then fast forward 18 months, which is a typical horizon or runway for a raise like that, the company is out of money and it just so happens that the stock market crashes in October, 2008. And as a result of that, the founder shows back up. I think we had about 25, 30 employees. And basically, everyone but five of us got fired. I got my first lesson on how not to fire people.

Tyler: Ugh. Yikes, that was terrible.

Rick: Yeah. So the founder shows back up. And he's a great guy. He's a love him, hate him kind of guy. I'm a lover. He's my mentor. He taught me a lot. He gave us our opportunities. We would not be in the positions that we are without him creating Zane Benefits. His style has the potential to rub some people the wrong way, a lot of people the wrong way. He put 30 people in a room and he basically said, "If I didn't talk to you five minutes before, you are fired."

Tyler: Yeah.

Rick: "Sorry."

Tyler: So Rick and I are sitting in this room where everyone else gets fired.

Rick: Yep.

Tyler: That was not comfortable.

Rick: And we did not know what to do. Do you remember that? I just remember looking around and all of our bosses got fired and people started crying. 

From sales rep to CEO

Tyler: And I felt terrible because it's like, "Well, what did I survive this?" Right?

Rick: Yeah. And so finally, I think the founder was like, "Get up. Rick, leave. Tyler, leave. Please collect yourself. We'll talk to you later." So we dropped 90% of our people that day. Anyway, the founder had started another company at the time that was taking some of his time. And he also basically was like, "There's six months cashflow. You have six months to turn this thing around and make it work or we're going to run the company through bankruptcy." He basically said something like that. And you and I had worked a lot together and the business wasn't working the way it was set up.

Tyler: It had some customers, but it wasn't a flop, but it wasn't going to sustain itself.

Rick: No, no. And so we actually ... We came up with a plan to pivot the business. We actually got to cash flow positive in three months. You and I were doing most of the work to do that. You on the technical side and then me on the sales and marketing side. And that was great. You left about a year later, I think, to start Less Annoying CRM, and I became the effective leader... the CEO of Zane Benefits and bootstrapped it to about $4 million plus in annual revenue in about 2013, 2014 timeframe. And learned a ton about how to lead, how to deal with the board. Because I was not a founder and there was also a lot of money that had come in previously, the founder didn't control the company. There was a board of directors that had control and so I learned how to work with some really powerful personalities and get them aligned on some things.

Fighting incumbents and regulators

Tyler: Well, we're going to talk later about your philosophy and what makes you different but, in previous podcast episodes you've referenced, you're starting something now and you want to maintain total control. I mean, at some point, you may raise money but I assume that was somewhat informed by your experience of trying to run a business while having very little control over it.

Rick: Yeah. And I would say, when things are going well, it's fine. So from 2009, 2010 when you left to 2014, we grew 100%, 60% a year. We were at $4 million, growing 60% a year, which was making everyone happy. And we did that without raising any money after the blowup. So things were going well. What ended up happening was in 2013, September the 13th, Friday, I remember it like it was yesterday, the IRS put out a notice that was pretty aggressive and shady, but inconclusive and gave ammo... We were disrupting a big industry of health insurance. And when that notice came out, the whole industry just went after us big time and said what we were doing was illegal, even though it wasn't.

Tyler: And so this started, even when I was there, various people tried to say that our product was illegal because of various nonsensical reasons. And at that point, the IRS had said ... what they said was probably not correct, but they gave people a little more reason to believe that fear.

Rick: They wrote in a way that a normal person would interpret it as that's illegal, but they never said it was illegal. Does that make sense? It was 13 pages of gobbledygook legalese that I could read and go, "Oh, they're saying this, but that doesn't mean it's illegal." But trying to explain that to people, it really put the business in a situation where it was a one-trick pony and we were either going to win this battle or not.

Tyler: Yeah. It's worth pointing out, when we say illegal, it's not like we're trafficking drugs or something. This is, can small businesses receive the tax benefits offering health insurances that big businesses do, basically?

Rick: This is basically, “is something deductible and excludable from taxable income, regardless of who pays it?”

Tyler: Yeah.

Rick: Whether the company pays it directly or whether the company reimburses it. I am 100% right that this was legal. It was legal.

Tyler: Because it's a thing now, right?

Moving the company and pivoting again

Rick: It's legal, yeah. And so what ended up happening, though, was we were growing like crazy in 2013. We ended up hitting a growth wall. We had to move the company from Park City to Murray. That was really freaking hard. We turned over half the company because people didn't want to move to Murray.

Tyler: And that's, what? A 30-minute drive between the two?

Rick: About 45-minute drive.

Tyler: 45. So it's not like you moved them across the country and still, you lost half the company?

Rick: Yeah, yeah. The mentality was that. And plus, the legal notice came out, scared everyone. Everyone thought the company was going to fail. So after that, we had to pivot again and I realized ... I went to the board and I basically said, "Listen. This business is a one-trick pony. It's going to succeed or fail on this legal issue. I have some ideas on how we can diversify the business," and ended up convincing the board and existing investors plus a new investor here in Salt Lake City to invest money into the company to build a new platform, a new brand, a new product that would have multiple points of failure. And specifically, we were in the health insurance business, specifically with Zane Benefits. This new business would tackle a similar problem in all types of benefits; health, retirement, cell phone, that sort of thing.

Tyler: So let me back up for a second. You were effectively operating as a CEO since the day after the layoffs. How did you official role and kind of power at the company evolve over time?

Rick: I wouldn't say the power really changed at all. I don't want to sound pompous here, but I was always the person who was instigating the direction. And I think you were number two in that. I would not have been able to do it without you implementing and improving a lot of the ideas I was coming up with.

Tyler: But neither of us had any official power, in terms of ownership or title or anything like that. So how did that change?

Rick: I would say we did. Paul, the founder, gave us responsibility and the power to make decisions. Where that came to its limits was dealing with the board of directors on things that needed to be approved like budget, compensation, those sorts of things. So I don't know if I'm answering your question.

Tyler: What I really mean is, when did you become the CEO?

Rick: Oh, when did I become the CEO? Technically, I was offered the job ... President is the official term for board of directors. So there's the CEO, it really doesn't mean anything in terms of corporate governance, but usually there's a president of the organization who is appointed by the board.

Tyler: Okay.

Rick: There's a secretary, that sort of thing. The president is who has the power. And so I was offered the position of president in 2009, actually, I think.

Tyler: Okay, so pretty quickly.

Rick: Yeah. And I declined it because I was fine to take the responsibility, but I didn't want my title to be president because I didn't want people to think I was the president of the company because I was dealing with some really big companies. I was dealing with United Healthcare, I was dealing with Paychex. I was dealing with people who were 10 years, 20 years, 30 years my senior and the last thing I wanted was them to think I was running this thing. I wanted to be able to point ... Actually, like I said ...

Tyler: Like, Paul's the ... yeah.

Rick: I used Paul big time. I was like, "Paul is the CEO. Let me run it by him." And I'd call him and be like, "Hey, Paul. How you doing? I've got to run this by you so that you give me a decision. I know what you're going to say. Yep. All right." But it was kind of a façade.

Tyler: Okay, so you got power pretty quickly and then ... Sorry, I kind of diverted us there, but you were making this pivot from Zane Benefits, which is this company that the IRS notice had come out, people were leaving and kind of moving into this new brand, right?

A new company, PeopleKeep

Rick: Yep, yep. And just to give you an idea of how hard Zane Benefits was, we were getting cease and desist letters from Departments of Insurance. We actually got investigated by the Department of Labor, while I was there. And we won that issue. We resolved it. That took three years. So that issue started around 2014, 2015 and ended in 2018. And then, so anyway, I raised the money from the group. The hypothesis was, one, Zane Benefits will succeed, potentially and this will be legalized. Or two, we'll have another business to pivot to with PeopleKeep if it doesn't. Everything took a shit ton longer than I thought. I did not understand how cap tables worked at the time. I did not understand how hard it was to recruit talent when you don't have an option pool. So I raised $3 million over six months and none of those raises actually expanded the option pool. So I went all about this and I realized I didn't own enough of the company. I realized a lot of people didn't own enough of the company, and it ended up causing a lot of distress at the board level in terms of getting alignment on the long term. Because I'd raised the money, I felt obligated to stick around and get it to a point where I could hand it off to someone or we could fix the issue by raising more capital. So I worked really hard from 2015 to 2019. I hired a new CTO, who built out a really great technical team, built a new product, got it to about $120K in MRR. It took way too long to build a product, about 18 months. 18 months after that, we go to $120K in MRR. And then, just recently in 2016, we got a bill passed and signed into law by Obama that legalized ... and then Trump just put out a notice, an executive order, further clarifying that what we were doing was legal.

Tyler: Legal, yeah.

Rick: And so I got the company to where it had survived through that legal challenge and then had a new platform and brand, now called PeopleKeep. And I got fired in October, 2018, so last year, as a result of ... The truth is, we couldn't get aligned on compensation.

Tyler: Yeah. So you weren't fired so much as what you needed to stay wasn't what they were willing ... It seemed somewhat mutual.

Rick: Yeah. We worked together for six months trying to figure something out. I went back and forth between whether I was going to be able to accept it or not. And ultimately, they made the right decision, which was, "We need to go hire someone else with a different set of compensation to fit what we want to do." I was prepared for that, so it wasn't actually a big deal for me. I think that the board, when they broke the news, they were scared of what I would do, because there was a lot of tense moments at the board meetings and the relationships were ... It was hard, right? And it wasn't the best situation, but I ended up getting fired. I drove home. I was fine. I was like, "Wow." I got married the next week. This is a week before my wedding. Yeah.

Tyler: I hadn't pieced that together.

Rick: Yeah, yeah. So got married, went on the honeymoon, came back. What I was not prepared for was how much of my life and my routines were built around PeopleKeep.

Tyler: Yeah.

Rick: Everything from when I woke up, to when I ate breakfast, to when I took a shit. Everything revolved around PeopleKeep. And I woke up one morning, I was like, "I don't know what to do. I don't know what to do."

Life after PeopleKeep

Tyler: So we were talking about this earlier today at lunch. You kind of were saying, going forward, you're going to be focused on something but you always want to have one or two other things going on. Is that a lesson you learned being too bought into PeopleKeep?

Rick: Yeah. So I was definitely ... I would say that, with Zane Benefits, I had other things going on on the side. I wrote a book that got published by Wiley. I did some consulting. I was playing around with things on the side that I was interested in. I wasn't all in but, once I raised venture capital and I felt the pressure of that, I was all in. And so I said no to everything. If it wasn't related to PeopleKeep, I did not talk to anyone.

Tyler: Do you think you have to be all in like that if you raise venture capital? Or do you think you could do it again, knowing what you know now? Raise the money, but have more balance.

Rick: Yeah. I think it's all about expectations that you're setting and boundaries. And I think I didn't realize how important it was to set boundaries at work.

Tyler: It's insanely windy outside right now.

Rick: Yeah. It is. It's kind of scary.

Tyler: Yeah.

Rick: So, yeah. I would say that, if I were to go do it again, I think it's important not to be so all in that, if it was taken away from you, you wouldn't know what to do.

Tyler: Yeah. No, and I can ... It's interesting hearing you say that because ... yeah. If I woke up and ... Even if I'm on vacation, checking Slack and email in the morning ... what, do you just wake up and look at the wall? What do you even do?

Rick: Yeah. I mean, I think what you don't realize what ... The only way I can describe it, for you, if you own a company or you run a company, just imagine waking up the next day and not being able to do anything related to it. I didn't want to talk to employees. It was inappropriate for me to talk to employees. I couldn't call the board. I couldn't talk to customers. Couldn't write a blog post. Nothing.

LegUp Ventures

Tyler: So, okay. That is a really, I think, interesting rollercoaster ride up to early 2019. Now, when you start these podcast episodes, you say, "Hi, I'm Rick. I'm the founder of LegUp Ventures and so on." Talk a little bit about what you're planning, going forward.

Rick: Yeah. Some context there, I had no idea what I wanted to do for about ... When you go through a big change like this, there are really two options you can take. You can jump right into something else or you can take time to let your body and mind heal itself and truly reflect. It took me about six months, from October to March, to really get to a place where I was, "I'm ready to go do something." And then even since March to now, it's September, I'm just now getting to the point where I'm excited about what I'm doing. So there's a big journey of me figuring out what I want to do next. And I ultimately decided that I should start a company of my own. I miss PeopleKeep very much now. I miss having what you have, something to care about, but I don't miss not having full control and being able to run it the way I think it should be run. And so my goal is really to ... I've started LegUp Ventures, which is a holding company for ... I kind of think of it as an incubator for my ideas. I might buy a company, but I won't buy it unless I ... I get reached out to every week with people saying, "I want to raise seed capital. Do you provide seed] capital?" No, that's not what we do. What we do is we own and operate companies. So I've started a couple of things. My hypothesis is that, if I can start three things, keep three things going at the same time and then when something fails, which I think will happen 66% of the time ... so every three things I start, two will fail ... I can just recycle and start something else. I'm going to find something that gets to a point of, "Hey, this is real and maybe I can double down, triple down on that."

Tyler: Okay. So the idea isn't to split time evenly between three things. It's to place as many bets as you can and then, when one of them is working out, go back to kind of PeopleKeep mode to some extent, but you're in control this time.

Rick: Yeah. And I would say never to PeopleKeep mode, to primary focus mode. I think that they way I'm structuring my time with the ventures I have right now, one is this podcast, one is a company called GroupCurrent, and another is personal writing and consulting. The way I'm structuring my time right now is, GroupCurrent is about 50% of my time, consulting and writing is about 40% of my time, and Startup to Last is about 10% of my time. I guess, some of that time is going towards, what's my next idea if one of these things ... I ultimately want to drop consulting and writing. I always want to write, but I would like to write for my companies, not for ...

Tyler: Yeah. You want to sell a product, not a service.

Rick: Yeah, yeah. Yep. But, yeah. That's what I've got going on. Startup to Last, we've talked about that. That's this podcast. GroupCurrent is a company that's based in Park City that is focused on member-based organizations or communities. And we are working on building community management software and we also have a professional service that we provide. Our primary client that you'll hear a lot about on this podcast is PandoLabs, which is Park City's entrepreneurial community. So we manage that and we also have proprietary software that, we manage it as the directors of the organization, but we also have proprietary software that PandoLabs uses to manage its members. And then, on the writing and consulting side, I do a lot at where I write ... I don't say I write a lot of content but, when I do write content, I try to make it really, really short and powerful. And I'm working on a book right now that is focused on some of the learnings that I had while I was at PeopleKeep around leadership and emotions.

Tyler: Cool. So book, blogging, podcast, GroupCurrent with PandoLabs, and learning to code.


Rick: Oh, yeah. That's another ... So one of the things that I really want to do is, I want to get ... I'm not anti-venture capital like you. I would say that I'm anti-capital pre-product/market fit and I would describe product/market fit is something that says, "Hey, this is a real product with real customers that has an opportunity to grow 10X what it is now."

Tyler: And you're against that just because you want leverage when you raise, right?

Rick: I think that when you raise before product/market fit, you are raising on a hypothesis. Okay? And that means that you're going to give a lot of your company up and you're also going to give up a lot of the control of getting it to a place where it needs to be before you can truly scale it. And a lot of these venture capitalists will come in and they'll say ... Once you miss that product/market fit mode, you're either not interesting to them anymore and they want the business to turn into an exit or fail, honestly.

Tyler: Yeah. Get it off the books.

Rick: Get it off the books. I went through that and I didn't really like that experience. I think that it's really interesting to get a company to a point where you're at product/market fit and you have a growth engine, and you see an opportunity to invest capital into growth so you could do more things. I think that's really interesting and you can actually attract that capital at that point in time and not give up control of the business.

Tyler: Cool. So, awesome. We've kind of gone through the lemonade stand days. to college, to Zane Benefits, to PeopleKeep, to all these ventures you're on right now. What you did when you interviewed me is you asked me, what are some kind of opinions you have or some things people should understand about you so that they can contextualize everything you say on the podcast? What summary would you give about your own philosophy?

Rick: I think it really comes down to what I like and what I don't like. I'll start with what I like. I really like doing things that are fit ... I like the outdoors and physical fitness, so I like balance. I think it's important to have a mental work and life balance. I don't know what the right term for that is, but I don't like just being all in, not taking care of yourself. So a healthy, self …

Tyler: Self care.

Rick: Self care, healthy environment. I very much value continuous improvement. I think it gets into intellectual ... Let's just call it not ... I'll talk to you about what I don't like. I really hate lazy people. I hate people who are intellectually lazy. Hate people is the wrong word. I really dislike that. I have a hard time working with people who, when asked a question, they go, "I don't know," and they don't go, "Well, let's talk about it and let's try to figure it out," or, "Let me go look it up." I like people who are intellectually curious. I really don't like bullies. So when people are acting like bullies or companies are acting like bullies, or the government is acting like a bully, I react strongly to that.

Tyler: Your instinct is to rebel, right?

Rick: Oh, it's not just rebel, but to make the bully realize that they're a really bad person. At the same time, I really dislike victim playing. For example, people are victims and I agree that, especially when a bully is picking on them, that they need help. And I love helping victims of bullies. But the victim mentality of where it's, "I'm a victim, I'm a victim and I'm not going to do anything about it," I really struggle with. So I have a little less empathy for people who are victims without caring to do anything about it. Let's see. I also ... Generally, I'm a very direct person and I speak about the truth. So often times, I can come across as a dick when, in reality, I just am trying to talk about something and get to its core. So sometimes that directness can rub people the wrong way and that's not my intent.

Tyler: Yes. If I can editorialize here, because I've known you long enough that I've kind of seen a bit of a transition from you. Tell me if you disagree with this, but you've talked about work life balance. You talked about being direct with people. It seems like your instinct was to be a pretty strong-willed, direct person. We had, I think, our second episode or whatever about fear-based decision making that got you into some trouble, that you feel an emotional connection with people but you are expressing yourself in a way that they thought you were scary, almost. Right? You've said that to me, that people have been scared of you.

Rick: Well, I mean, you told me you were scared of me one night.

Tyler: Yeah.

Rick: I think we had a little bit too much to drink and we were hanging out in Salt Lake City. This is a few years ago. And you were like ... I was talking to you about this. I was still at PeopleKeep. You were like, "You are scary."

Tyler: Yeah.

Rick: I think you called me a psychopath that night.

Tyler: No.

Rick: Yeah.

Tyler: I said you used to be. The reason I bring this up is not to talk shit about you but to say ... For someone listening to the podcast, one really interesting thing that I am listening for when we talk is, you're in the middle, I think, of a transition. When you left PeopleKeep, you did a lot of self reflection. I think you softened a lot in a good way and opened yourself up. There are a lot of topics, even that you just said, that you wouldn't, I think, have admitted on a podcast three years ago, probably.

Rick: Mm-hmm (affirmative).

Tyler: I don't know. That's something people might listen for, is this transition of going from kind of hard-ass, closed-up CEO to a more open, do what's right for you, not as much of a type A type of leader.

Rick: Yeah. And I would say that I ... Well, the biggest takeaway from my time at PeopleKeep is that emotion of fear and how powerfully negative it is. So I hate being scared and I think that the perspective I bring is that, when you're scared as a leader ... and I try very hard to never let myself be scared as a husband, as a person, as a leader now because I think it makes people do really crazy shit.

Tyler: Yeah.

Rick: And I did really crazy shit because I was scared in the past. It's really hard to intentionally, well, catch yourself when you're in a scary situation and not let that affect your behavior. The best way to do that is actually to, I think, control, be thoughtful about what you decide to do with your life.

Tyler: Yeah. I think so many people find themselves in the situation where they wake up one day and they're like, "I am in a situation that I did not decide to be in and I don't know how to get out." And that's one of the great things about entrepreneurship and especially bootstrapping or, at least, bootstrapping your way to product/market fit is, yeah, you can be deliberate about every step of the way, what do you want for yourself?

Rick: Totally. Totally. So, yeah. I would say that's my unique perspective. My goals for long term are really just to ... I want to continue to build things. I really want to stretch my muscles on coding. So we'll probably have some topics as it relates to my journey with coding. And my main goal there is, I want to avoid bringing on a co-founder until I get to that product/market fit spot.

Tyler: Yeah. Awesome. If anyone's listening to this, one thing I'd love to know is, do you prefer the business topics? Do you prefer the technical topics? Because we could kind of go all over the place here, so I'd love to hear from people on that.

Rick: Yeah. That'd be interesting. So with that, we're good for the sign off?

Tyler: Yeah. I think so.

Rick: Well, everyone, thank you for listening. I don't really like talking about myself, so thank you for bearing with me on that. You can join the conversation on this topic and review past topics by visiting If you have questions, contact us via the website or on Twitter. We'd love to hear from you regarding your thoughts, ideas, or if you just want to opine on the conversation. That's See you next week.

What is Startup to Last?

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.