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 people who are doing those entrepreneur journeys, anew.
Jason Heflin:
I think prepare for the downtimes. The thing that you think, oh, if this happened, that would be bad. Well get ready for it. It’s going to happen eventually. Just get ready, build a plan around it. If this, then this, if this, then that. And sometimes it’s even helpful to kind of draw that out like a little tree. Just like, okay, if this happens, I’m going to do this and just be ready. And that way when it happens, you’re much more at ease. You can say, okay, I have a plan. I can follow it. I don’t know if it’s going to work, but I have alternate routes I can take.
Jamie Swaim:
Name it and claim it.
Jason Heflin:
Yep.
Molley Ricketts:
For me, it was business debt is completely different than personal debt, but personal debt for me was always, you don’t have that. That’s how you freedom and survive and live. But business debt, I went in with that same mentality, but learned that it’s not the same at all.
So when you think about looking at a business and you want to scale, you want to grow, where do you see businesses overcomplicating that growth?
Jason Heflin:
Well, on the topic of hiring, I think it’s quick fix hiring. And I’ve been guilty of that many times. Just like, oh, this person has the credentials. Let’s go hire them and let’s just move. And we talked about that in a previous episode recently. It’s just it does not work. It won’t ever work. You might get lucky and their resume is everything about them, but most often it’s not so quick.
Jamie Swaim:
Especially with AI, right? Yeah.
Jamie Swaim:
People are putting resumes together because they think that’s what you want to see sometimes.
Jason Heflin:
Yeah, yeah. Lean into the interview. Don’t be afraid to have a long interview. Don’t be afraid to talk about culture. Don’t be afraid to talk about the times in the past when they’ve had a conflict with fellow employees because those could bubble back up in your environment and come back to haunt you.
Jamie Swaim:
Absolutely.
Jason Heflin:
And it’s better for them too. They don’t need to be in a place that’s not good for them.
Molley Ricketts:
They human behind the paper. So what do you think real accountability looks like in your organization at CrowdSouth?
Jason Heflin:
Ownership of your area of expertise. That’s really what it is. And we did talk again in a recent episode about this, but letting them own it. Allowing them as an entrepreneur to own their area, getting in and being helpful by guiding the work and steering the work and kind and productive corrections are probably welcomed and should be welcomed, but not hovering over people. So I think them owning their area and then the entrepreneur allowing them to own their area.
Jamie Swaim:
As an entrepreneur, you have become no stranger to mitigating and navigating risks and learning how to make decisions that are right for you and your company. So I have a couple of questions as it relates to these things. What is a decision that you made that felt uncomfortable but was necessary?
Jason Heflin:
I’ll tie it back to a previous answer a couple of questions ago. Letting people go that are not a good cultural fit. It’s hard to do. Maybe they have all the talent, maybe have more than the talent, and you can see them fitting in a role somewhere else or even fitting in a role in your company, but just culturally they do not fit. And your team will let you know.
Molley Ricketts:
Pretty quick.
Jason Heflin:
Yep.
Molley Ricketts:
I agree with you on that.
Jason Heflin:
But it’s still really hard. They’re a good person. You’re like, gosh, they could do so much.
Jamie Swaim:
Especially if you’re doing any of the tips that we talk about around leadership and getting to know people and you learn their family, the impact of a job loss, those things start to hit really hard.
Jason Heflin:
Yeah. Oh yeah.
Jamie Swaim:
But your company’s better for it.
Jason Heflin:
A hundred percent.
Jamie Swaim:
All right. I’m curious of the risk reward methodology you have in your own head. How do you measure and evaluate risk versus opportunity?
Jason Heflin:
I struggle with it personally. I like to keep the gas pedal down all the time. So I’m very comfortable with risk and I will go a little too far with it.
Molley Ricketts:
Do you have an example?
Jason Heflin:
Oh gosh. Do I have examples? Yeah. I mean, it’s good for a business to be able to niche into things. These are the things we’re good at. But then sometimes an opportunity will come up to take on a new thing and start to think we can do that. We’d be great at that. But it’s a big risk to try something. You’re going to probably fail a few times. And especially if it’s a new client or someone you’re interacting with as an entrepreneur, you could really flub it up.
Think in terms of the big picture, go back to the plan for the year or the three-year plan or whatever it is, and say, does this really fit into what we’re trying to do and be okay not taking this work or this big chunk of money because it’s this shiny object or this brand that you wanted to work with. Or, Ooh, that would be great in our portfolio to say, I worked with this Fortune 100 company. Just be careful, evaluate it. Really sit back before you just take it.
Jamie Swaim:
And I don’t know that our listeners know this about you, and so hopefully I’m not going too far, but blink twice if I say something you don’t want me to say, okay, that’s my safe word. But prior to CrowdSouth and building this marketing conglomerate that you guys have gone and built.
Jason Heflin:
Conglomerate, I like that.
Jamie Swaim:
That sounds big.
Jason Heflin:
Sure.
Jamie Swaim:
But prior to that, you were not new to the entrepreneur journey. I mean, you started companies and if you were to go through them, they don’t all have something in common.
Jason Heflin:
Yeah.
Jamie Swaim:
You were in various industries and approaching it from different ways, but using key things that led to CrowdSouth. Do you want to talk about that at all? Because I think when people call you, they might be thinking about you through your marketing lens, but I used to refer to you as the person with the Midas touch. Everything you touch seemed to turn to gold.
Jason Heflin:
Maybe Copper.
Jamie Swaim:
Copper. The copper touch.
Jason Heflin:
Yeah, the copper touch. All
Jamie Swaim:
Right.
Jason Heflin:
Yeah. So a good example is I started a business once and it was fully because it was a good idea, but I wasn’t super, super interested in it. So that kind of bit me. Later I started an online, an e-commerce business. And of all things, we were selling diaper bags.
Jamie Swaim:
Before you even had a child.
Jason Heflin:
Oh yeah, I had no interest.
Jamie Swaim:
You even know any kids?
Jason Heflin:
Yeah. What’s a kid? I don’t know. What’s a diaper?
Jamie Swaim:
Why do you need a whole bag?
Jason Heflin:
Yeah, why do you a whole bag for these things? But it was a vacuum in the market, and my partner at the time and I went into it and it did really well. It just took off. And suddenly we were selling diaper bags and I turned a whole bedroom in my house into a warehouse. We had boxes stacked to the ceiling, and my wife and I were working on weekends shipping these things out and taking them to UPS, and it was exciting until it wasn’t. And so we ended up selling that business to a company called Hayneedle, which owned like 50 different e-commerce businesses. It was just better. They had all the things they needed to really take it and run with it. And I could go do a different idea. So I think my unique ability as an entrepreneur is knowing when to leave, knowing when to get out of the way.
Jamie Swaim:
But you’ve also been a travel blogger. You owned a microbrewery slash restaurant, and now are in the marketing business. None of those things have automatic ties to each other. Definitely using your marketing expertise to do that.
Jason Heflin:
And real estate business and bourbon and all kinds of stuff.
Jamie Swaim:
I don’t remember the bourbon.
Jason Heflin:
Most of them are opportunities. They’re like, I see an opportunity and so I can’t stop myself sometimes. So I do think it’s important because entrepreneurs have that same gene where they see an opportunity whether it’s a good fit or not, and they just chase it. And so be cautious of that. Make sure you don’t have to be something you’re just in love with, but at least have some sort of passion for it and know where it’s going to go. Don’t just start it because it’s a good idea and then not know what you’re going to do with it later.
Jamie Swaim:
Yeah.
Jason Heflin:
Have an exit plan or have a plan where you’re going to step to the side and let somebody else take this thing over somebody that’s more better suited, like, Hayneedle was.
Molley Ricketts:
Yeah. So Jason, when you think about your life as an entrepreneur and knowing that you’ve been with CrowdSouth for, what is it now 12, 13 years?
Jason Heflin:
Yep. Wow.
Molley Ricketts:
What does entrepreneurship cost you?
Jason Heflin:
Yeah, so I think it’s cost me time. Time and money you exchange. So for many years, the brewery you mentioned, I owned the brewery at the same time, I own CrowdSouth. And I would go in the morning and I would work all day at CrowdSouth and I would drive immediately over to the brewery and I would work till one in the morning. And I did that for two and a half years.
Jamie Swaim:
Which means the MVP is also Jason’s wife.
Jason Heflin:
Shout out. And during that time, had a baby.
Molley Ricketts:
Oh my gosh.
Jason Heflin:
And so it was just rough. And I realized I was exchanging too much the money for the time or the growth for the time, because it wasn’t a lot of money then. It was just, okay, we’re just growing this thing.
So yeah, time. So that’s really more what I’m trying to get back to focusing on. I’m going to start exchanging it the other way and I’ll make less and I’ll do less and I’ll be less successful in terms of the typical definition of success, but I’m going to have more time. And it’s probably an age thing too. I hit 50 this year.
Jamie Swaim:
Happy birthday.
Jason Heflin:
So it’s like, okay, well I’m kind of waking up to, okay, it’s time to slow down.
Jamie Swaim:
Success redefined?
Jason Heflin:
Yep. Yep. And just my son’s getting older and it’s a ticking, as they say.
Molley Ricketts:
So what would you tell your younger entrepreneurial self?
Jason Heflin:
Slow down. Think about these decisions. Don’t jump into every thing that looks good. That’s not always, like I said earlier, I just chased everything that was an opportunity. And I think that’s fine when you’re young and single or you don’t have a lot of obligations, but as those obligations increase and compound, you got to take a step back and say, again, back to where I said, let other people do it, empower them. Start empowering people and start getting yourself out of the way. Because especially as you age, you can’t keep up with everything. You can’t keep up with all the technology and the trends. So let somebody else help you there.
Molley Ricketts:
So last question before we close our file. What is it about CrowdSouth that’s different than all of your competitors?
Jason Heflin:
I can say, I mean, there are a thousand agencies across the country, marketing agencies, so I’m sure there are plenty that are like us. But I can say that we have developed a culture. One thing we’ve done right is we have a culture where people care. People care about the clients that care about the results.
Sometimes a client will come in and they just want a brand project. We want to be seen more, or we want our employee brand just to be out there. And we’re very results driven. So I think it’s, it’s a superpower, but it also gets in the way because we’ll drive the client, we’ll be like, Hey, no, we need to be doing better and these are the things we need and this is what we’re going to do next.
And sometimes they’re slow down. We just got our heads around doing something basic and we’re like, yeah, but we see so much back to the entrepreneurial kind of spirit and go, let’s do this.
I think we’re really good at results driven work and we like to set smart goals early and have numbers behind everything. And that’s what we’re going to target every time we’re going to drive toward that. So I’m very proud of the people that have gathered around us to do that. They all care too, and it hurts them when we don’t do well. And I think a lot of companies don’t admit when they don’t do well, but we like to say, Hey, look, that didn’t work, but we’ve got four new ideas to try.
Molley Ricketts:
Sure.
Jason Heflin:
So, come back to the table with that. That’s what I’m proud of.
Molley Ricketts:
Awesome. Well, thanks for coming on the show and letting us bend your ear and twist your arm on all the questions.
Jamie Swaim:
It’s good to have you.
Jason Heflin:
Yeah. Thank you. I’d love to come back sometime.
Molley Ricketts:
We’d love to have maybe next file.
Jason Heflin:
Okay.
Molley Ricketts:
Alright, Jim, close that file.
That’s where we’ll leave the conversation for today. Before we close the file, we invite you to reach out to us with questions, suggestions or other comments. We’d love to hear from you.
That’s where we’ll leave the conversation for today. Before we close the file, we invite you to reach out to us with questions, suggestions or other comments. We’d love to hear from you.
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Need Help Supporting Your Company’s Recruiting and Staffing Goals?
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- Jamie Swaim, SPHR – www.ParcelKnows.com
- Molley Ricketts – www.IncipioWorks.com
- Jason Heflin – www.CrowdSouth.com
We hope you found this file insightful and helpful. Thank you for listening!