File 35: Jason Heflin sits in the "hot seat" to share insights from his entrepreneurial journey, which began after he realized he was not wired for the repetitive nature of a corporate cubicle. The interview explores his core business philosophy of avoiding commoditization by prioritizing deep, long-term strategic partnerships over one-off product services. When asked about scaling a business, Jason highlights the importance of "stick-to-itiveness" and the risk-taking necessary to overcome the fear of failure. He admits that his greatest operational challenge was learning to embrace standardized processes, a discipline that often feels restrictive to his "free spirit" nature. Regarding team management, Jason emphasizes accountability through ownership and the difficult but necessary decision to let go of talented individuals who are not a cultural fit. Reflecting on his diverse past ventures—ranging from a diaper bag company to a brewery—he cautions against chasing every "shiny object" without a clear plan or genuine passion. Having once prioritized "winning" at the cost of his personal life, he has since redefined success to focus on family and empowering others to lead. Finally, he identifies his company's differentiator as a results-driven culture where team members genuinely care about outcomes and are not afraid to pivot when strategies fail. Key Themes: Breaking Free from the Gray Cubicle The Partnership Obsession The "Stick-to-itiveness" of Scaling The Copper Touch: Lessons from Diaper Bags to Breweries Ownership and the Hard Truths of Leadership Redefining the Win: From Toxic Growth to Time Well Spent Episode Transcript: Jamie Swaim: Today on the Workforce Therapy files. We'd like to welcome you back and also tell you that we have a special guest that is in the hot seat. Molley Ricketts: Who? Jamie Swaim: It's none other than your favorite. Jason Heflin. Yes. Molley Ricketts: And the crowd goes wild! Jamie Swaim: So, Mr. Heflin, we have a number of questions that we'd like to just pick your brain on in this episode, in this file. Jason Heflin: I'm turning my hat around backwards for this. Molley Ricketts: Uh-oh. Jamie Swaim: Is that straight up? Out of over the top. Are you Lincoln Hawk? Jason Heflin: Whoa. Jamie Swaim: Yes. Might've been one of my favorite movies. I'm not going to lie. Molley Ricketts: He trembled a little bit. Jamie Swaim: I know. And I'm ready to arm wrestle him just to see what happens. So Jason, I want to start off with, if you were a professional athlete and you had walk-in music, what would be the theme song you would choose? Jason Heflin: The Final Countdown. Jamie Swaim: Oh, there was a little harmony there. I like it. Final Countdown. Gosh, I do feel like that's a song I haven't heard recent enough. Jason Heflin: Yeah. There was a show 20 years ago called Arrested Development. Jamie Swaim: Yes, Jason Heflin: It was great, and one of the characters would always come out to that song. He was a magician, and that's how he would come out. He would do a little dance. Molley Ricketts: It's a great show. Jason Heflin: It's a great show. Jamie Swaim: Jason Bateman, right? Molley Ricketts: Yeah, Jason Bateman. Molley Ricketts: In the early years. Jamie Swaim: He's one of my favorites. Molley Ricketts: Yeah. Jamie Swaim: Okay. Now we're going to get more serious, but it's helpful to know because I feel like when I see people and I know that about them, immediately this song pops in my head. Jason Heflin: Maybe it should be the intro, Jim, to this episode. Jamie Swaim: He said you can't afford that. Yeah. Jason Heflin: We'll just have to sing it! Jamie Swaim: That public domain? Is that how it works? Molley Ricketts: Copyright laws. Jamie Swaim: I dunno. Alright. So, Jason, what was the first moment that you realized you were wired for entrepreneurship? Jason Heflin: About six or seven years into sitting in a gray cubicle in a corporate office. Jamie Swaim: You're like, this is not for me. Jason Heflin: Doing TPS reports. Jamie Swaim: You've been missing a lot of work, Jason. Jason Heflin: I said 'm going to do something else and it's not going to be for someone else. I need to exercise that muscle. Jamie Swaim: How long did that take you? Jason Heflin: Oh, like I said, six or seven years. Jamie Swaim: Six or seven years. Jason Heflin: 6-7. Jamie Swaim: Okay. What problem are you most obsessed with solving right now? Jason Heflin: Not being a commodity. Jamie Swaim: Tell me more. Jason Heflin: So I don't want our services to be commoditized. And I think often that's the way we're approached initially is, Hey, we need a website, or we need ads for hiring, or we want to attract talent through digital advertising, blah, blah. Whatever the thing is. And they're just looking at it like a commodity. Jamie Swaim: Dollar. Product. Jason Heflin: Yeah. Do you do it? We're going to ask 12 other people the same thing. And then whoever has the cheapest prices who we're going to pick. I want to build long-term partnerships. I mean, that's what I've always wanted. That's what we strive to do. And so it's really hard for me when someone enters our funnel as looking at us as a commodity. And then you have to kind of flip that and say, no, I want to go to lunch and get to know you and your team and what we're trying to do here, and let's build a strategy around it. I don't want to just do the thing. And then you're disappointed in six months. I want to really dig into what the true issues are. Jamie Swaim: I would imagine what the kind of work that you do, the longer-term relationships create better outputs any way. Jason Heflin: Oh yeah. Jamie Swaim: It's not like, oh, let me put together your whole employment brand because I've known you for two seconds. Jason Heflin: We've had clients for 12 plus years and they're the best. I love 'em. They're friends, they're partners. Partners is overused, but it's true. They're real partners. We're in their business. We go in their office and the admins know us and just shoo us on back to the conference room and no security and just, yeah. Jamie Swaim: Yeah. Molley Ricketts: It makes a difference. Jamie Swaim: I'm assuming, because you've been in business now for 72 years? Jason Heflin: 73. Jamie Swaim: 73, okay. I don't want to undersell your knowledge, but I'm curious, how has your definition of success evolved across that 73-year spectrum? Jason Heflin: Well, in the year 1 through 50, I was really more focused on winning. So it was more toxic culture, toxic growth for the sake of growth. But yeah, so I'm more focused on time with my family, treating people really well, building partnerships, long-term partnerships I want to be in for years with somebody. I don't want to waste anybody's time. So yeah, less winning, more hanging. Jamie Swaim: Well, as someone who's known you for at least 30 of those 73 years, I think it's a solid choice. People should do it. Jason Heflin: Thanks. Jamie Swaim: Yeah, for sure. Molley Ricketts: All right, Jason, so what do you think separates entrepreneurs who scale from the ones who stall? Jason Heflin: Sticktoitiveness. Is that a word? Jamie Swaim: It is now. Jason Heflin: Okay. Webster's definition of sticktoitiveness is staying the course. Go. I mean, I think the ones that don't scale are maybe fearful. Being an entrepreneur is about risk, and you have to be willing to take those risks. And if you're not, it's going to be a very slow process. So don't expect it to be a quick run. If you're not willing to lose and lose multiple times. Molley Ricketts: You definitely have to be okay with the word no, a lot. Jason Heflin: I've started and sold at least four businesses in my life, and I made that mistake many times over in the past. Molley Ricketts: So what operational discipline do you think takes founders way too long to execute, to learn? What do they avoid for too long? Jason Heflin: In my experience, this is self-reflection, but it was process, building processes around commonly common tasks. Jamie Swaim: Standard work. Jason Heflin: Yep. Things that we do over and over again. We know how to do. Somebody's already figured out step one through six, just put it down, this is it. These are the rules. We can change the rules anytime if things in the environment change. But yeah, and I resist process because I'm a free spirit. I just want to operate. I'm a cowboy. I don't want to be pinned down. So that's tough for me. And my business partner's really good at it. So we have complimented each other in that way over the years. Molley Ricketts: I agree. It's definitely as a fellow free spirit, seeing things on paper with process and 1, 2, 3, A, B, C, and it's like, really? You couldn't just do it? Jason Heflin: I get itchy. I feel pinned in. Jamie Swaim: I know this isn't something that you said, but I'm curious around the same question because I know we're interviewing Jason, but we like to have a little chitchat. I feel like the founder relationship with cash also is something that might get in the way of people scaling. And I don't know how you guys have done that or whether or not that's a challenge that you had, but for the bootstrappers or the individuals who are getting started with some sort of investment cash, figuring out how to leverage debt, figuring out how to budget for the down months, figuring out how to do that and not be, I don't know, discouraged from continuing. I know you guys have had nothing but green, gold star months in your careers as entrepreneurs, but I'm curious what you might advise for the
