What do you do when everything you built starts to crumble?
For four entrepreneurs featured on this special episode of The Midgame Mindset, that question wasn’t hypothetical. It was urgent, emotional—and the beginning of something far greater. From Shark Tank deals to $50M exits, from breakdowns on bathroom floors to rebuilding from scratch, these founders show us that the most pivotal growth moments often begin with a full stop.
If you’re a founder, CRO, or CMO navigating the messy middle, this episode is your roadmap for what’s possible when you let go, look inward, and come back stronger.
“I Thought I’d Failed the American Dream” — Courtney Turich, Co-Founder of Monkey Mat
Courtney Turich had the kind of founder story most dream about: national exposure on Shark Tank, a double-deal with Mark Cuban and Lori Greiner, and a product with traction. But behind the scenes, things weren’t adding up. Inventory cycles drained cash. Her marriage felt the strain. The business, once thrilling, began to feel like a burden.
The breaking point came in a doorway in her own home. “I finally said, ‘It’s time to walk away’—and tears just came pouring down my face,” she shared. That decision, though gut-wrenching, was the beginning of a full reset.
Courtney stepped back into a rep role in medical devices—not to “start over,” but to recover her confidence. That quiet return to her roots led to a leadership position at Cooler Heads, where she helped commercialize a new product and recently helped secure Series A funding.
Key Lesson: Sometimes growth means stepping down—so you can step back up, stronger and clearer.
“Everything I Built Was Gone Overnight” — Krista Anderson, Founder of Healthy On The Go
Krista Anderson wasn’t just building a brand—she was building a mission. After surviving cancer, she was shocked by the food offered in hospitals. So she launched Healthy On The Go, offering nutritious snacks in places like gas stations and medical centers.
But just as the company was gaining traction, her distributor cut her out. “I remember lying on my bathroom floor, in tears, thinking: ‘Everything I’ve built—I just lost overnight,’” she said.
What came next wasn’t hustle. It was healing. Krista moved to France, took a sabbatical, and let the business breathe. “It was the energy of letting go that brought it back,” she said. Today, Healthy On The Go is thriving again—present in major U.S. hospitals and airports—and she’s rolling out a new beverage program with top brands.
Key Lesson: Letting go isn’t giving up. Sometimes, it’s the only way to revive a vision.
“I Was Letting Everyone Else Dictate My Life” — Brian McNally, Co-Founder of Meleo
Brian McNally had his eyes set on a $20M year when the pandemic hit—and his healthcare staffing company lost 50% of its revenue in six weeks. “I thought I was strong,” he said, “but I hadn’t really been tested.”
The turnaround didn’t start with a funding round or a pivot. It started with Extreme Ownership. Literally. Brian devoured David Goggins and Jocko Willink, cut the noise, and reframed everything. “I was blaming the world. Then I realized: I’m the one in control of how I respond.”
That mindset shift led to a bold decision. When his company outperformed during a sale negotiation, Brian retraded the deal—asking for (and getting) a massive increase over the initial offer.
Today, he’s launched an executive coaching business, started a local men’s group, and is writing a book to help others reclaim purpose.
Key Lesson: When the game changes, so must your mindset. Ownership is the path to reinvention.
“I Had to Step Away Completely” — Morgan Gebhardt, CRO & Serial Entrepreneur
Morgan Gebhardt scaled companies to $300M+ in ARR—but at a certain point, success felt empty. The culture he’d helped build was eroding. The grind was unrelenting. He didn’t step into another role—he stepped away entirely.
“I took a full sabbatical,” he said. “Moved my family to the country. Started doing timber work and helping my wife with a flower farm.”
That time off wasn’t passive—it was transformational. Morgan recentered on empathy, culture, and the kind of leader he wanted to be. When he re-entered the workforce, it was with new clarity and a deeper understanding of how to build safe, high-performing teams.
Key Lesson: Growth doesn’t always mean go. Sometimes, you scale by stepping back and healing forward.
The Midgame Isn’t the End. It’s the Turning Point.
These aren’t stories about founders who crushed it from day one. They’re stories about hitting walls—emotionally, financially, existentially—and doing the hard inner work to come back wiser.
As host Rich Bishop put it: “With the right mindset, the best moves are still ahead.”
What You’ll Learn in This Episode:
- How to navigate the emotional toll of walking away from a dream
- Why some of the best strategic moves begin with a sabbatical
- The difference between owning a business and owning your mindset
- How culture, not just capital, defines your next chapter
- Real-life examples of turning breakdowns into breakout moves
Watch the full episode here → Watch on YouTube
If this story resonated, share it with someone in the messy middle of their own journey. The next move might be their best yet.
Full Episode Transcript:
The Emotional Toll of Entrepreneurship
0:00The journey of an entrepreneur is not for the faint of heart. They often experience failure.
0:05When I finally said, “It’s time to walk away.” And tears just came pouring down
0:10my face because in my mind at that moment, I was living the uh quote American dream. What I thought I also
0:18thought I had failed. I remember laying on my bathroom floor in tears, thinking,
0:24″Oh my god, everything I’ve built, I’ve just lost overnight. what am I going to
0:29do? But many of them will find themselves in the process. Talk about that midgame
0:34moment. It was a full reset, a reboot, uh a sbatical, uh time to work on myself, you know, time to challenge who
0:41I was, draw on and reflect on all of the past experiences I’d had and, you know,
0:47also, you know, look outwards uh into other sources of wisdom. It was actually the time that I joined the Outlaw
0:52Project, then Talent Champions Council. And in doing so, they’ll reach new heights of success that they only
0:58dreamed was possible. I was like, “This thing’s got a heartbeat. I don’t know how, but it does.” And so, I went for it.
1:06We outperformed. We felt like we earned it, but it was such a massive increase from the initial um LOI.
1:13Welcome to the Midgame [music] Mindset. Join us as we dive into the pivotal moments that shape today’s top sales and
1:19marketing leaders, RevOps innovators, and [music] entrepreneurs. This is where grit meets growth, and the game changes
1:26for good. [music] If you find value in this conversation, be sure to share it with another growth leader who would
1:31enjoy it. And now, let’s get to the show. Welcome to the Midgame Mindset. I’m your host, Rich Bishop, and I’ve
1:38been interviewing growth leaders now for about eight months or so since we’ve started this podcast. And they come in
1:45all shapes and sizes, marketing leaders, sales leaders, entrepreneurs, and others
1:51that are all concerned with the growth of their companies and in the process
1:56also with their own personal and professional growth. And without a doubt, there are some key
2:02themes that have started to pop up as I’ve interviewed a number of these. and and one of them happens to be with
2:08entrepreneurs. Many entrepreneurs say that it’s a very lonely road to go down,
2:14but when you talk to many of them, you start to hear some similar themes. There’s great excitement and opportunity
2:21at the beginning, but without a doubt, they face failure in the process.
2:27Many of them will step back and take another look at themselves and repprioritize and redefine what success
2:34means. And after that, they then are able to reach new heights of success as they
2:40come back at it from a different perspective and a different mindset. That’s exactly why we’ve set out to do
2:46this podcast is to really get into a growth leader’s mind and understand how they approach those challenges. What we
2:54want to do today is bring to you four of our entrepreneur guests from the past so
2:59that we can hear about their journeys and their stories that you can learn what that successful mindset looks like.
3:06We’re going to hear today from four incredible entrepreneurs that we’ve interviewed in prior episodes. And we’re
3:12going to take some of the best pieces of those interviews and include them here for you today. And we’re going to start
3:18with Courtney Turk. Courtney is the co-founder of a company called Monkey Mat and she took Monkey Mat onto the
Introducing Our Entrepreneur Guests
3:25Shark Tank stage and was grilled in front of millions of people just like you see on all of the shows and she
3:33ended up striking a deal with Mark Cuban and Lorie Grineer. [snorts] It was an incredible experience for her. But as
3:40they got further into trying to build the company, she and her husband realized maybe it’s not right for us to
3:47do this long term. We’re also going to hear from Christa Anderson who survived
3:52cancer and in the process was absolutely appalled with the food choices that were
3:58available in the hospital while she was getting her treatment. She’s made it her mission to bring healthy food and snacks
4:05to places where maybe people can’t find them, like gas stations, like airport
4:11convenience stores, and unfortunately sometimes hospitals, too. We’re also
4:16going to hear from Brian McN. Brian is a gritty guy from the streets of Philly
4:22who started his company Melio as a healthc care placement company and he
4:28bootstrapped it from zero to $50 million and of course had some bumps and bruises
4:34to face along the way. And then last but not least, we’re also going to hear from Morgan Ghart, who is a serial
4:40entrepreneur in CRO, who’s taking companies from literally the ground stage to 300 million in revenue. He had
4:48to hit pause and really step back and decide what it was that he wanted to do with his life in order to make an impact
4:55after he saw some of that success and realized maybe this isn’t really who I am.
5:01Can’t wait to dive into these important lessons from entrepreneurs.
Lessons from Courtney Turek’s Journey
5:11Let’s [music] face it, nobody wants to fail. Failing is hard. It bruises the
5:16ego. And some people can actually take that as a reason to just stop doing what
5:22they’re doing altogether. Successful entrepreneurs will take failure as a way to learn, as a way to
5:29grow, and more importantly, as a way to pivot their life in the direction that
5:34they’re taking into something more productive. That’s exactly what we heard from Courtney Turk when we were talking
5:41to her about her company, Monkey Matt, and the experience that she had with
5:46Lori Grineer and Mark Cuban as her mentors. Take a listen. once it airs,
5:51right? Because they want to protect their asset, which is the show, and and making sure that um the surprise is
5:57there for everybody and it’s not ruined. So then then you’ve got Lori and Mark
6:02that you’re now working with. Take take us through the rest of then what happened with the company and with you.
6:09Yeah. So Mark and Lori were very involved. I will share with you. Mark Cuban is real always has the
6:16entrepreneurs best interests. I don’t know how this guy does it, but you would send him an email and I’m telling you,
6:22he would respond within minutes. It might not be a lengthy response, but it would be very direct and to the point.
6:29He had a full team to help us with website design, um, just financial like
6:35financial accounting and all of that. We had a business manager. They would set up different places where we could go do
6:43big promotions at. Um, we even went on Shop HQ. So, one of those shopping channels. So, I got to present on a
6:50shopping channel, which which was really cool. And not going to lie, for a moment I thought that was my next calling,
6:55Rich. I thought I was going to be I can see that. I can see that. It may still be. Yeah, I did. I did. Um, and then Lori
7:02Grineer, awesome. She got us on QVC. I wasn’t personally on QVC, but she she
7:08did represent the product there. We had a great run and reality was at the end
7:14of the day it just wasn’t going to bring in what we needed financially to
7:19survive. Everything that came in went back out for inventory and it was just this constant cycle.
7:27And then it came to with me, my business partner and myself. Is this what we
7:33really want to be doing? Right? Like are we really in this?
7:39And I was really struggling struggling financially and my husband looked at me and he said, you know, we can’t keep
7:45doing this. We got to move on. And that was a moment that I had to make a hard decision. Was I going to stay or was I
7:52going to go? And part of that was my marriage, right? Like I I really had to
7:57look reality in the face and say, “Is this something I can keep doing?” And I couldn’t. That is something so hard for
8:05anybody to go through because you’ve poured your heart and soul into building this company to get this to where it
8:11was. You’ve had some amazing success with it, right? And getting those deals, but then to be able to say, you know
8:18what, this isn’t quite going to cut it for what we need and what we want out of our lives and be able to to shift. First
8:25of all, there’s nothing at all wrong with doing that. But second of all, I think there are a lot of entrepreneurs
8:30that feel like there is or maybe there’s a sense of of shame at the moment that that that happens. Did you go through
8:37some of that as well? And what was that like? I sure did. I went through a lot of shame. And Rich, even thinking about it,
8:44I get a little emotional because I knew deep down inside the answer was that I
8:50needed to move on, but I was so afraid to say it out loud. M I will never forget the moment I was
8:56talking to another Shark Tank entrepreneur who had to walk away from her business.
9:02I know where I was standing in my house exactly like with like in the doorway
9:08when I finally said it’s time to walk away and tears just came pouring down my
9:14face because in my mind at that moment I was living the uh quote American dream. what
9:22I thought. I also thought I had failed.
9:28Yeah. And you know, it’s really wild to look back how far I’ve come from that moment
9:35and to realize it was still only the beginning for me. Courtney decided to step away for a
9:41little while and find herself and what it was that she truly wanted. And we’ll hear from her again in just a few
9:48moments about what that journey was like and where she is now. But sometimes you
9:53don’t have the choice to make that decision. Sometimes you’re forced into
9:58it. Sometimes by some of your biggest partners. That’s what we heard from Christa Anderson where one of her
10:05distributors for her company ended up essentially stealing the idea and
10:11cutting her out. As you can imagine, this was really tough for her to deal with, but again,
10:18she learned some really important things about herself and her business in the process. That’s awesome. So, you you
10:25went for it. You ended up pulling a couple of You found the manufacturers that you were looking for, right? Did
Krista Anderson’s Mission for Healthy Food
10:31you find them at that at that show or did it take some time to kind of settle in on who’s really providing the healthy
10:38food here that I can get behind and and put my brand behind? I did find some at the the trade show.
10:44Absolutely. And some were just connections I made by online searching.
10:50And from from the beginning of my research to start the business of this conversation with the convenience
10:57store guy to going into the first convenience store was six months. So it
11:03was quite fast surprisingly. Um we had a lot I had a lot of hiccups along the way with the merchandising displays and
11:09things like that. But I pulled the portfolio together fairly quickly and we gave it a test. So
11:15that’s great. So you pulled the portfolio together, got into the stores.
11:21Now, did you have distribution at that point or were you working all of that out of your your garage studio?
11:28Oh my lord. I have photos I still I sometimes I see I’m like, how did I ever
11:33survive this moment of my life? But I had pallets of product and UPS
11:39deliveries delivered to [clears throat] my door. I would carry them up the steps, stock them in my bedroom,
11:46bedroom, kitchen, living room. It was one room. uh and just had my inventory
11:52in this room and then um I would deliver all the deliveries to the stores twice a
12:00week, sometimes three times a week in my Honda Accord. Um and I did this for I
12:06think three years until it got too big where I couldn’t keep driving around and
12:13it expanded out of Tennessee and then we had to find a distributor to do it for us. So, [laughter]
12:19so you’re living in boxes. You’re doing laundry around boxes. That’s fantastic.
12:24Yeah. [laughter] Such a great story of the the grit that
12:30it takes to um really get something off the ground and moving. So, once you’ve
12:36expanded so far that you can’t do the distribution yourself, tell me about that first distribution agreement that
12:43you had. Well, the the retailer, they kind of forced it onto the distributor
12:49because the program was doing really well and we had enough volume for them to bring these items into their
12:54warehouse. And so we got it all set up. I did all the paperwork for that and then they
13:01started delivering to all the stores. It was pretty seamless. But um yeah, I mean
13:07it it allowed me to then take the business to anywhere in the United States with that new strategy that okay,
13:13now I know healthy foods can sell in convenience stores. Then we started to move into universities. Um you know, now
13:20we’re in a lot more other retail categories, but you know, it started to grow. It gave me the opportunity to to
13:27really expand nationwide. So, and we had a kind of a strategy that could be um
13:33was a good blueprint to duplicate into other parts of the country. So, um and
13:39then of course that’s when that that same distributor came in and pretty [clears throat] much
13:45stole everything. And unfortunately, you know, you’re a small business, you can’t afford to hire a lawyer to sue them.
13:53You know, for me, I’ve never taken an investor in this business and I’ve bootstrapped everything and so I didn’t
14:00have the will to fight back. I couldn’t do it and I lost, you know, everything at that point. So,
14:06God, that had to be so hard to deal with. What What was that process like of
14:14kind of getting to or going through the stages of grief, I’m sure, that that anyone would kind of expect in that
14:20situation? um what was that like for you and and what was the moment where you came out
14:26on the other side and decided what your next step was going to be? I will say I
14:31lost at that moment all trust in humanity in a way because the people I
14:38was working with they were almost they they were friends too. You know we you
14:43know I was working with a group of guys in this organization and they were kind of like a brother at times. I could ask
14:48advice and they were very supportive and knew the mission behind healthy on the
14:54go. You know this has never been a a money business for me. It’s been very obviously missionbased and how they
15:01could just rip off a small business. Like I remember laying on my bathroom floor in tears thinking, “Oh my god,
15:09everything I’ve built I’ve just lost overnight. What am I going to do?”
15:19To experience [music] that kind of failure is one thing. And there are a lot of people that don’t really look into what it means. They
15:27don’t look internally to see what needs to change. And a lot of people will play the blame game, blaming others, blaming,
15:35in Christ’s case, the distributor for what had happened. But that’s not what she did. We’ll hear the same thing now
15:42from Brian McN. It’s not that the economy in 2020 collapsed or struggled
15:47and really caused a dent in his business. He used this as an opportunity
Brian McNally’s Accountability Journey
15:52to turn inward and look inside himself and identify what it was that he needed
15:58to do differently if he was going to be effective. I had thought I was in a good mental place and was strong and and but really
16:04hadn’t been tested truly tested. So, we’re 5 years in, we it’s March, we are
16:10on a run rate to do 20 million. I mean, we got the whole company pushing for 20 and 20. We’re juiced.
16:16The bottom falls out. We lose 50% of our business in six weeks. I’m hemorrhaging cash, you know, like most people
16:22struggling on what to do with my employees. And uh we were built on on integrity and culture, right? So, how do
16:29you honor that in the toughest moments that you have? I was letting everyone else dictate to me how my life was going
16:34to go and how my business was going to go. And I was blaming everyone else around me. And I read two books during
16:40that time. One, I deleted social media off of my phone, which was to get me out of the funk, right? Because it was just
16:45a negative spiral. But then I listen I downloaded Audible and listened to David Gogggins Can’t Hurt Me and Jo Willix uh
16:51Willings Extreme Ownership and both just had a profound immediate impact on my life. And I think one of the things that
16:58I’ve been blessed to be able to do is take action on things that I learn. I don’t just consume information and then go on and consume more. I I actually
17:04implement. So when I read Gogggins Can’t Hurt Me, I’m like, well, this guy’s been through a lot worse situation than I
17:10have. And he pulled himself out of it. So basically, I was being a little I was whining and complaining about what the world did to me. And I’m
17:16like, that’s not how I’m raised. I just talked about where I came from, right? And how I was this tough, gritty neighborhood I came from. And so, um, I
17:23started to really take accountability for looking at life through the lens that I am in control of how I respond to
17:30anything that happens. And if people are failing around me or failing to meet my expectations, it’s because I didn’t set them properly or I didn’t train them
17:36properly. So, there’s always something I can do to improve my situation. There are a lot of entrepreneurs that
17:42are very type A personalities. They’re go-getters. They want to get done.
17:48And this works for them in many ways. That’s how they get started and that’s how they can be successful. But
17:54unfortunately, that can create an illusion of control. We heard just
17:59recently from Brian that sometimes there are things outside of our control. And it’s important to understand and step
18:05back when do we control the situation and when do we not. If you fast forward
18:11through two pivots of that business uh again from services to automation to
18:16conversational AI um to over 300 million in in annual recurring revenue great
18:22journey u but after a while something was off. It wasn’t right. Um and I had
18:30that realization that um I had to take take stock step back um and recognize
18:38that there were dynamics that were beyond my control, right? We have an illusion of control most human beings,
Morgan Gebhardt’s Sabbatical and Self-Discovery
18:44right? We think that we can directly influence all of the events around us. Um but in the end, um it that only goes
18:51so far. Um and I had that realization that the business was kind of eroding from within first. Um and it was
18:58increasingly difficult for me to have an impact, drive effective change, continue
19:03that growth trajectory. Um but after 15 years, it’s really tough um to step away. Uh and the decision I made wasn’t
19:10to step away into another opportunity, right? The decision I made was to um
19:16step completely away from the working world, right? And talk about that Midgame moment. It was a full reset, a
19:22reboot, a sbatical, uh time to work on myself, you know, time to challenge who
19:27I was, draw on and reflect on all of the past experiences I’d had, and you know,
19:33also, you know, look outwards uh into other sources of wisdom. It was actually the time that I joined the Outlaw
19:39Project, then Talent Champions Council. Um, and you know, focusing on community,
19:45uh, and looking for that sense of purpose outside of the working world,
19:51which so many of us have at the center of our of our, you know, sort of selves.
19:57For sure. That that sense of community is important. And it’s hard when you’re
20:03in that grind of especially the startup world where it’s so fast-paced startup
20:08world so venture capital private equitybacked companies there’s always an urgency uh to delivering results and to
20:16making change happen that must have I mean 15 years is a long time to be grinding and going and to go
20:23from 2 million to 300 is a a massive change you had to have I’m sure rewrite
20:29the organization mult multiple times in order to to get there. How do you go
20:34from from that grind in the the gas pedal being down all the time to
20:39sbatical? That had to have been a challenge. Yeah. Um you know, it it it was um it
20:45was on one hand very difficult. Um there was the constant uh sort of a
20:51combination of of pull to keep me in that that action. Um and and frankly
20:59also that a little bit of a a sense of guilt um counterbalancing that that pull
21:05that gravity um that I wasn’t taking effective care of myself and if I
21:11couldn’t take care of myself I couldn’t care for those around me right um
21:16the transition itself was after I made the decision and after I I exited I mean
21:22I won’t say that I didn’t have recurring dreams of being back in the workplace on the regular for weeks if not months
21:28right? It’s sort of that becomes really part of your life. Um uh but I was able
21:33to reenter in other things. I was fortunate to have a piece of property uh that uh shortly after I took the
21:39sabbatical moved the family to our our house in the country um full-time out of the city. Um and that gave me um literal
21:48and figurative grounding in a way. I started working in the forest doing timber stand improvement. I helped my
21:53wife start a flower farm. um I just centered on being in nature uh more than
21:59anything else. Uh and that made that transition so much easier. Yeah, for sure. And how long did that
22:05soatical last? Um so, you know, I took that sobbatical open-ended intentionally. Um I had some
22:11sort of rough um imaginary [clears throat] timelines in my head like, hey, maybe I’ll take it for 3 months or 6 months. We’ll see how it
22:17goes. um 3 months after I exited the business
22:23um this little thing called COVID happened. Um uh and I you know of course you know blessing in disguise in a way
22:29where you know the decision we’d made to leave the city. Uh and so I looked at that and I said hey right maybe this is
22:35just another sign from the universe if that’s how you want to look at it saying no you really need a break to
22:41disconnect. Uh whether you like it or not [laughter] you’re going to be you’re going to be uh you know isolating out
22:47here. Um and so I would say that sbatical lasted just short of three
22:53years. Um, and I was lucky enough to have had enough success in the previous business to have the the uh the safety
23:00net sure uh to allow that to be open-ended. And you know, through that doing a little bit of consulting or advisy work as it came up completely on
23:06my own terms. Um, and I I would look I would highly advise anybody taking that
23:12can take an extended break. Um, I don’t know if I would advise three years. U but for me it was um it was right.
23:19Yeah. the world was working in your favor in that sense just in in all of the change and upheaval that that took
23:25place in 2020 and and beyond from there. For sure. It’s important to recognize what we don’t have control over. But
23:32there are some things that we do have control over and sometimes we have to discover that ourselves. Courtney Turk
23:39told us about how she stepped away from Monkey Mat and took a job as a sales rep
23:44again to get that passion and that fire back for being a salesperson before she then had the opportunity to go on to her
23:52medical device company called Cooler Heads. She tells us a little bit more about that transition and how she found
23:58herself in the process. There was a previous company before Cooler Heads where I’m at today. It was
24:04I went to go work for a mentor of mine, Ryan Denny, and I I can’t say enough about him because it was when I stepped
24:11back into the med device space, I I told myself that I wanted to go back into leadership. But what I didn’t realize is
24:18I needed to take a step back and just go in and take care of myself, and that was being a rep.
24:25So, I went back in, ended up having just this amazing ride with a startup called Veron Medical for lung cancer. And then
24:32when that was over, I found I came I stumbled upon Cooler Heads and that’s
24:38where I’ve been the past almost four years, which has been another crazy wild
24:43ride. I joined Cooler Heads before we commercialized. So, I was part of the
24:48commercial setting up that commercialization strategy and I’ll never forget running around trying to
24:54sell that first unit myself. That’s great. So you you get to you you
25:00help with commercialization. You then of course want to prove, hey, yes, there is a viable market for this. We can do
25:07this. Um after being a rep to kind of I
25:12guess in many ways get your feet under you again, right? Is that kind of what that was about being a rep and just kind
25:17of getting back into the rhythm of things and then that kind of opened up the door for Cooler Heads and what you
25:23were doing there. Yeah, great point, Rich. So, it did it allowed me to just get my feet under
25:28myself again and really to get my head straight, to get my mindset back aligned and what I really needed to do to embody
25:37who I was again at the core because I lost myself there towards the end um when I left my Shark Tank company. But
25:44when I was at that last startup, I had opportunities where I grew into some leadership roles within the company. And
25:51that allowed again that that fire inside to come to the surface to help grow some
25:57younger reps below me. And it was one of the most rewarding experiences I’ve had
26:04professionally to date, except for now cooler heads
26:09that you got a taste of that leadership again almost, right? It was like, “All right, yeah, that’s that’s what I want.”
26:15You started, sounds like you started to kind of feel alive again in that moment as a as a result.
26:21Not kind of. I did. I really came alive and really started to understand who I
26:26was. Rich, I think that’s an important part of all of this. You know, while I felt so lost when I left my Shark Tank
26:33company, stepping in and just taking care of me allowed me to really focus on
26:38who is Courtney. Mhm. And that’s where I rebuilt my confidence. I learned where my voice was
26:47again and also just realized to go out and be myself was one of the most powerful things I could do. Was there
26:54something about that role in that experience that you did you find something new or did you rediscover
27:01something that you knew was there but maybe you had repressed it or set it aside because of what it was because you
27:08were chasing that American dream. I believe it was always there.
27:13I think it was lost and I didn’t really understand my strengths to their full
27:20capacity. back to I’m a huge believer in the
Discovering Strengths and Empowering Others
27:26Gallup StrengthFinder. I knew what my strengths were, but it
27:31wasn’t until I started to see some successes happening within my my
27:37territory and that I started to reflect back and say, why am I doing so well?
27:45Why am I feeling like I’m really in this great groove? what am I doing differently now that I wasn’t doing
27:51before? And it was I was embodying who I was at my core. Like I understood myself
27:58finally. And then I took that and I passed it on to my team and helped them do the same thing, which you know to
28:06watch them have those aha moments when they saw their strengths surface and that they were thriving and we were all
28:13working like we were on this like we were just all in sync. so dialed in. It
28:19was one of the coolest experiences ever, Rich. And that’s when I realized I had this gift of helping other people
28:26realize what makes them shine. And if I can do that for them, it makes me shine even more.
28:31Courtney stepped back into the role of a sales rep and found her passion again
28:37for what it was that she was doing. That really solidified her next steps in
28:42Cooler Heads. Now, when we look at Christa Anderson, she didn’t step back into another role.
28:50She stepped into an entirely new country. I booked a one-way ticket and went to France. And I was like, I have got to
A Journey to France: Finding Perspective
28:57save myself because I I mean, I couldn’t breathe. I I was really stressed. And so, I spent a couple months in um France
29:05and just processing everything. And I decided
29:11I I wanted to move. So, I pack went home, applied for a visa, packed three
29:16suitcases, and I moved to the south of France, and I’ve been here ever since. [laughter] Wow.
29:22So, it it’s not the right answer for everybody, but I will say it’s shocking
29:29to me where the business is today after I decided to pick up the pieces and and
29:35that journey that I went on to get there. Yeah, I definitely want to unpack that because I think that’s that’s important.
29:41There are a lot of people who deal with I if they deal with um the situation
29:48that you described. If they deal with that kind of situation in their lives, sometimes it’s a divorce, sometimes it’s
29:53a business failing, sometimes it’s a loved one close to them passing away, right?
29:59Maybe it’s just even failed relationships uh in general that a lot of times people will try to either
30:07medicate it chemically, right? Or they’ll try to just move past it and
30:12stay busy. And that’s where a lot of, you know, workaholic um tendencies tend to come from is let
30:19me just keep going and just keep busy so that I don’t have to pause, sit back and reflect on what’s just happened. And I I
30:27think there’s a lot of value in sitting in that moment, in that part that just
30:33really sucks and understanding and learning, okay, what what is it that I’m
30:38supposed to learn here? What is it that I’m supposed to see? And I I applaud
The Importance of Letting Go
30:44you. A change of scenery to France sounds like it helped give you the right kind of perspective to to be able to see
30:51it and sit in that for a little bit but learn the lessons that you were probably intended to learn as a part of that
30:57process. Absolutely. I I could talk for days on
31:02what the lessons I’ve learned from leaving a a one a society that we grow
31:09up in and you know one way of thinking, one way of being and one way of doing to
31:14another culture and you learn so much from other cultures. I think that’s the
31:19power of travel. But you know, for me it was I rode the business out financially
31:26uh while I took a break. And as it the unraveling was happening, I was slowly running out of money. And you know,
31:34there was a moment where I was like, “Oh my god, what am I going to do? I think I have to get a job.” You know, because I couldn’t decide
31:41if I wanted to go back to building this business again. I thought, “Why would I build something up that someone can just
31:46wipe out in an instant?” and I didn’t trust anybody anymore. But it came back
31:52to, you know, after taking a year or so off um and running this through my head over
31:58and over and over, I tried to start another company. It just didn’t flow. Didn’t feel right. But there was
32:04something sitting in me and I think, you know, it’s this calling or our what
32:10we’re supposed to do with our life in a way and I couldn’t get rid of it. And so
32:15I thought, “All right, I’m going to go back to this, but with very positive
32:20avenge, you know, so I I’m I’m on fire and we’re going to fight harder than we
32:27fought before.” And it took me a long time to revive and stand back up and do that again. But the thing that I will
32:33say is what I learned from the French culture is that it was not about me anymore. and what I was building the
Reconnecting with Purpose and Passion
32:40business on before I I was never interested like I said in money but or
32:46fame or any of that but I felt like I was too much the front of the business with my story.
32:57So we’ve covered in the entrepreneurial journey that you will experience failure sometimes it can be really hard and
33:04shake you to your core. The successful entrepreneurs will look internally and
33:09sometimes even step back from the business as we’ve heard in order to find themselves again and to find that
33:15passion. The next step in that journey for these successful entrepreneurs is to
33:21repprioritize and sometimes to let go. All while sitting in the south of
33:26France. And I’ll say this one last thing is one of the greatest life lessons I’ve
33:32learned is that the energy of letting go and not trying to make something happen,
33:38trying to be successful, trying to be number one, trying trying, but you just
33:44let go. There’s a great book I read called The Surrender Experiment by Michael Singer.
33:51Fantastic book. how he built a multi-million dollar company on letting
33:57go and saying yes to the things that come and let life guide him instead of
34:02him guiding life. That’s that’s how this business has grown. And I don’t know how someone
34:09living in another country with a 6 to 8 hour time difference can build the business to where it is today. And I’m
34:16incredibly grateful. But it was a letting go. That’s awesome. And and I’m going to
34:21butcher the quote because I I don’t remember exactly where it comes from, but there was always a a quote with a
34:27visual of of holding a baby bird in your hand, right? You you don’t want to hold too tight because you’ll you’ll crush
34:33it, but you don’t want to hold it too loose either because then it’ll fly away and it’ll get away. You’ve got to you’ve
34:39got to hold it with the right amount uh in order to keep it there, in order for it to to thrive and to do well uh in
34:45that position. And I I agree with you. I think there’s there’s a lot to be said for the frenetic pace of just go go go
34:54and wanting to control everything because you have to mentally, right, just to kind of keep it all straight.
35:00And then the the difference of you know what, let me play it more instinctively and read the room, read what’s
35:08happening, and uh take advantage of the opportunities when they’re there, but
35:13not press when there isn’t an opportunity there. Yeah, absolutely. And
35:18I think the part of the letting go too is that we have to have balance as entrepreneurs
Balancing Life and Work as an Entrepreneur
35:25even as employees any any like it our jobs cannot be our life. When we’re out
35:31of balance the our work is out of balance and nothing can succeed when when it’s like that. And I think you
35:37know that’s another thing I learned from the French is that they don’t to they don’t
35:43you know live to work. They work to live. You know, they’re it’s not their number one priority in life. And that’s
35:49not where their identity comes from. And it’s about making sure you’re
35:54exercising, you know, you’re eating well, you’re you’re living and enjoying life. And then it’s, oh yeah, I’ve got
36:00to make money, you know, which sounds completely different in the United States. And so it’s a different way of
36:06thinking, but it works. It really works. Entrepreneurs can get caught up in the day-to-day, in the hustle and the bustle
36:14of everything that’s going on, especially when a company is small. But
36:19as the company grows, the needs become very different. Leadership and culture become a driving dynamic. And sometimes
36:26you can lose sight of that as you’re going through from company to company or from stage to stage in its growth. when
36:34you step back sometimes that leadership and culture refocuses you and becomes a
36:40central priority again. If I kind of try to find the intersection of self and and career and
36:48purpose um I would say it helped me um I
36:53I reconnected with something I think I’d always had. I think I I got it from my
37:00mother, which is an innate sense of of empathy and compassion. And I realized
37:06one of the things that was burning me out in the workplace um at least that specific workplace was that the the
37:13grind also came with um a lack of appreciation for others, who they were,
37:21um you know, how they showed up, um the challenges that they may go be going through inside and outside the
37:27workplace. Um, and it helped me sort of get back to and reenter on leadership style.
37:32Um, and that’s kind of really where I was I found myself doing a lot of reflection and focus was, you know, how
37:38can I bring that to the four in a very um, intentional and conscious way and
37:45lead with empathy and compassion. Um and while still of course being able to be
37:52um in in the role where you’re making decisions and sometimes those decisions are difficult and they impact people and
37:57not everybody’s going to be happy. Sure. Um and and you know I think the other thing um that was really at the
38:03center of that journey was um that it’s not about you or in my case me right um
38:09that as much as we center ourselves in our own narrative we are not uh the center of anyone else’s narrative and it
38:16really helps you move through space um with others and again in a very intentional way
38:23that actually the the whole concept of it not being about you I think any
38:28parent out there will know real quickly that that is the number one learning that you
38:34pick up the moment that you bring that child home is guess what your life is not about you anymore. And that can take
38:40a number of of different shapes and and sizes. But when you when you look at it that way and apply
38:46it to work and apply it to building businesses and growing businesses, it
38:51really can make a difference in the culture and the business that you’re building. Right. Yes. Well, absolutely. Um, and
38:58interesting you mentioned culture. I also spent a lot of time thinking about culture because I was coming from a pretty toxic workplace culture. And that
39:04intentionality that I wanted to come out with extended to um the kind of culture
39:09not that I just wanted to be in, but that that I could foster. Um, and I
Building a Culture of Empathy and Safety
39:15certainly brought that to my next role, which was a a CRO role um at a business that was in the um u AI space, AI
39:23enablement, um, you know, data labeling and annotation for building AI models, both visual and and language. Um, and
39:30and the company I joined itself had a very intentional culture in place, which
39:36was so important for me. Um, and the the
39:42thing a lot of people miss about culture, um, is they think you set culture from the top with mission and
39:48vision and values. Um, you can write as many values on the board as you want.
39:54Um, culture springs from the collective people in that business or community,
40:02not from the top down. In fact, you create more friction when you try to force culture on [snorts] folks. But but
40:08you have to live the culture you want to create and foster yourself, right? Um
40:13maybe you people call that lead by example. Uh for me it’s a little bit more lead with intentionality. Is that
40:20word again? Um and and allow the dynamic to find its
40:25footing. Um and then lean into the good aspects, the positive aspects, right? And and have by the way difficult
40:32conversations. It’s also part of it, right? A healthy culture is a culture where people can be vulnerable um and
40:39still feel safe. That’s the other aspect. It was really important to me. Building a culture of safety because
40:45people perform their best when they feel safe. There are a lot of people that we
40:50hear family is first. Family is most important. At least that’s what they say. And then when you look at their
40:57actions and more importantly their calendars, it doesn’t necessarily line up with that.
41:04I was really impressed with Brian McN’s take on this when he came out and said
41:09his family was third for a while because there in his mind there were some important foundational pieces that he
41:15had to take care of first. Take a listen. In some ways there hasn’t been a whole lot of change because one of our values
41:20that Jason and I were was really important to us is that we’re not going to do this and create this business and
41:26and sell at the risk of like losing our relationships with our family and our children. you know, my wife’s, you know,
41:32because so many guys go through this and they get divorced and they’re on their third, it’s just a mess, right? Their personal lives are in total disarray and
Prioritizing Family and Health in Business
41:39I came close to that at one point, but we we kind of corrected that. And so really leaning into that, right? How am
41:45I a better father, a husband, so every year uh I I set my own priorities for my top three. And at the time of the
41:52business, it was the business was number one, then my health, and then my family. And I know that sounds harsh like, oh, you put your family third. Yeah, I kind
41:59of did in order to serve them. And that doesn’t mean I don’t see them or not actively involved. But it means if
42:04there’s a decision point most of the time the business has to win and my health had to win so that I could serve
42:10people. Um you know a good example of that is like on a weekend morning my son wants to hang out and like watch a TV
42:16show like no I had to go do some emails. I had to exercise and then I would hang out with him. And that’s not easy right?
42:24But now that’s flipped. They are the priority number one. then my health and then do business or actually friends and
42:30family. Business is fourth. I’m not even It’s not even on my radar at the moment. It’s there. I do it when these other things are served. So, it’s just a
42:35matter of ranking priorities. It takes the decision fatigue out of it. Like I already know what I need to do, what’s
42:41most important to me. You know, we do jiu-jitsu, right? So, that wins. That’s part of my health. Like, I do that
42:46before I do business now where in the past I I would skip jiu-jitsu to if
42:51something came up and I had to do it, right? So, just having those priorities. So that’s uh important to me is just
42:57really investing in that. And I started a executive coaching business. I started
43:03a men’s group which is another huge thing. I just think men are don’t have a place where they can be vulnerable and
43:08have a place to share each challenges and men are struggling out there. I was in that position, right? I was very
43:13unhappy and unhealthy and unfulfilled without purpose in life and uh I don’t want other men to go through their life
43:19that way. So, started a men’s group here locally uh and in the process of writing a book to kind of map out my strategy
43:27and real tactical things that people can implement to start living a life of freedom and fulfillment for themselves.
Creating a Legacy Through Leadership
43:34I love it. I love it. That’s great, man. You’re you’re repurposing your life for the things that are right here at the
43:40center for you. Um and kind of really paying attention now to to some of those
43:46really the legacy type things. Right. When I hear that, it’s it sounds like it’s about leaving a legacy for your
43:52son, for the the men around you, for the people around you, the people that you’re impacting and and having an
43:58impact. Yeah, man. It I think uh my inial goal was freedom. Like I I knew money was a vehicle for freedom. I’m not a very
44:04materialistic person. Even my business partner, we were the same way, which was great because we were very much aligned, right? Because there was a lot of
44:10opportunity to keep that thing running. I mean, everyone was like, “You’re crazy. Why are you even selling us?” But we’ve achieved the goal. The goal is
44:15have flexibility and freedom to spend time and live our lives.
44:23[music] We like hearing about success stories, but it’s not often that we spend time on
44:28the hard things, the failure, the introspection, and what it’s like to have to refocus in order to go back at
44:35it. But now, let’s get to the good part, the success. because each of these
44:40entrepreneurs that we’ve highlighted today have gone on to new levels of success. And we’re going to start here
44:46with Courtney, who is leading growth at Cooler Heads, recently raised their series A funding and is off to a
Success Stories: Overcoming Challenges
44:53fantastic start in the growth of that company. Let’s hear a little bit more about what she has to say and how
44:58excited she is about this opportunity at Cooler Hats. You start off in the [snorts] commercialization phase. You
45:06just recently, congratulations by the way, announced series A funding, right?
45:11So, getting from not even commercialized to series A is a big leap and one that
45:17many entrepreneurs don’t ever really get to. How has that journey been? And now
45:23you’re starting to build your team up again. What is that like? That journey is like any entrepreneurial
45:29journey, Rich. I mean, back to we were talking earlier about those highs and lows. You know, it’s an emotional roller
45:35coaster. It is the same way at a startup. Nothing is a guarantee. Tomorrow is not a guarantee. And again,
45:42I’m very fortunate to my mentor Ryan Denny who introduced me to Coolerheads and he was with me at the very beginning
45:49when I started at Cooler Heads. We created this commercialization strategy together and really we wanted to see can
45:56we make this work? Is the market really going to embrace this technology?
46:04And the fun part of it was they did. And it hasn’t always been perfect. By
46:11far has it been perfect. I mean, through the days of trying to raise the series A and I’m going to give a shout out to
46:18take Kate Dilligan, our CEO. She’s a female founder CEO. We’re here because
46:24of her cancer journey. and she went took it upon herself to create a product that
46:30was easier to use, more user friendly for both the staff and patients and to
46:36give patients that empowerment that they lose so much during chemotherapy or during their cancer diagnosis.
46:44So to be part of this mission, to be part of selling that first unit, to be
46:49part of treating that first patient and holding our breath to make sure the system actually worked like we said it
46:56would to the FDA. Like those are moments you can’t make up or you can’t relive. Rich,
47:01Brian Mcnal knew what he wanted when he started the company and they built the company with the end in mind. So when he
47:08had the opportunity to sell the company, what did he do? He went back to the table for more. I
47:15love his take on this because he knew where they were as a company and he knew what the opportunity was and he sure
47:22took advantage of it. Yeah. And you guys were obviously very systematic in the way that you built your business selling to a private
47:29equity strategic partner. What was the the most bold move that you made along
47:35the way? Yeah, probably the the biggest move and and the most risk was when we retraded our deal with like two weeks
47:41left or so. Um that was it was scary for sure, but it was we talk about being
47:47having values and kind of um knowing your worth a little bit and and and we really did feel like we were on such a
47:54trajectory that we would have that we earned it, right? But it was incredibly scary because we’re in an environment
48:00where we’re first time selling a business. We’ve got brokers and lawyers and adviserss and um they’re all
48:06advising us not to push for what we pushed for and um
48:12the reality was we were on a massive uh increase like our our trajectory was huge and we were selling midy year and
48:20so everything was based off our trailing 12. Well, the deal was dragging a little bit and we had another just monster
48:25month. So, our trailing 12 shot up exponentially. And everyone kept warning us that you
48:30can’t let your foot off the gas. If if you start to come down, they’re going to retrade and lower what they offered you.
48:36And so, this is where a little bit of that gritty kind of Philly guy comes in. I’m like, “Oh, if you’re going to retrade me down, I get to retrade you up
48:42when I outperform.” This is, you know, this is either a two-way street or we’re not party or we’re not partners, right? That’s how I looked at it, right? So, so
48:49you get the advantage of lowering my price if I don’t perform. And I don’t get the advantage of increasing my price
48:54if I do perform. It’s not gonna I didn’t feel good about that. So, um, we outperformed. We felt like we earned it,
49:01but it was such a massive increase from the initial, um, LOI that, uh, it took
49:07some conversation. And really, this goes back to to sell is as human, right? Like
49:12I had just read, uh, never split the difference, which, by the way, because was good time to read it when you’re selling your company. Um, and one of the
49:20key elements I pulled out of that book was like, don’t get caught up in the numbers. And that’s what our broker was
49:26saying. Well, this is a such a high percentage. No one retrades over that kind of percentage. I’m like, forget the numbers. We’ve that’s the value of our
49:33business, right? I don’t care what the historical norms are. And on the other side of this table is a strategic buyer who I know wants to work with us, who I
49:39have an excellent relationship with the CEO. Like, we we we were on the same page the whole time. This whole thing was going so smooth. And even the
49:45private equity group, we’re good guys. and and they this was we were their first add-on to the platform and like
49:51they want to get this deal done. They want to work with us. So, how do we work with them to make it comfortable for
49:57everybody to with the number and just kind of get on the same page? So, really just end up being a phone call with them. We just got out of the lawyers and
50:03got out of the bankers and just said, “Hey man, this is how I’m feeling. This is what I’ve got going on. This is why
50:08we’re asking and we found common ground and we made it happen.” But, you know,
50:13it took a call with an investment banker who basically said, you know, he yelled at me. He’s like, “This is big boy stuff. I don’t think you know what you’re doing. You’re about to blow this
50:19whole deal and all that kind of stuff.” And like always, me and my partner just had to have each other’s back and look
50:24at each other and say, “Hey, if we got to take this thing to market, then that’s what we have to do, but we’re going to get what we’ve earned.” And I
50:30don’t think that’s what’s going to happen, but that’s what, you know, we need to be willing to do. And from a company that was almost dead,
50:36Christa Anderson’s Healthy on the Go has come a long way. She’s in many of the US
50:41airports today in each of the convenience stands that you’ll see and
50:46she’s also in a number of the hospitals which is right back at the center of where this whole thing started to begin
50:52with. It was great hearing her journey and some of the expansion that she has
50:57coming up. All right, let’s go to you’ve got the the call to get into the the
51:03health care systems. The the business has a has a heartbeat. Tell us what that experience was like of of taking that
51:10step and then where did you go from there? How did the business get from there having a little bit of a heartbeat
51:17to the thriving business that it is now? I believed in it again. And I think
51:22because someone else believed in it first to remind me that it was a need,
51:27that retailers wanted it, needed it. And so that kind of put the wind back in my
51:34sales to start sailing again. And with this healthc care contract, it allowed
51:39us to have access to 250,000 healthc care facilities in the United States
51:44because you have to have approval in most situations to sell something in
51:50there. So we had the basically the contract to do so and so just started
51:57going after that and luckily we’ve you know last year we got a um contract with
52:04the second largest healthcare group in the US and we’ve been rolling out with them nationwide which has been really
52:11exciting. We’re selling, you know, upwards of 650 units a month in just a
52:18hospital of this section of healthy snacks, you know, and it’s like people
52:23want this. Medical staff are looking for this. Um and then you know it was just
52:29seeing the success grow that it you know I continued to reach out to other
52:35opportunities and you know we got a we have a contract since last year as well with um a large airport uh retailer
52:45which is actually a French company. Um and so working with them, we’re
52:51rolling out um nationwide with them, which has been really exciting and helping travelers have healthier
52:58options. It’s funny, we are in it’s June 9th right now. So March, about three
53:06months ago, exactly three months ago actually, I had the idea to do this. And
53:12in 3 months, we’ve developed a a whole new beverage program. [clears throat] And we have the the coolers in the
53:19warehouse ready to go. And we’re we basically vetted, you know, America’s
53:25top healthy beverages. And that was hard because there’s so much crap in
53:32beverages. It’s unbelievable. Now, snacks, of course, you see that, but
53:38there’s a lot more healthier snacks than there are beverages in my opinion. And so, we’ve had to vet through a lot of
53:44stuff, and we’ve got some of the top um healthy beverage brands part of this program, which is super exciting. As
53:51we’ve seen, the journey of an entrepreneur can be a wild ride. With the failure they experience, the
53:57introspection that they have to go through, refocusing themselves, and then reaching new levels of success is a
54:05tough journey to go through, but the ones that can do it end up reaping the benefits on the other side and are so
54:12much happier as a result of it. Of course, don’t leave out the pain in the
54:17middle that they have to go through as a result. I hope you’ve enjoyed this episode and
54:22the best of and if you have, make sure you go back and listen to the full episodes and interviews with our guests
54:28today. There will be more of these coming. So stay tuned. [music] Make sure you subscribe so you don’t miss another
54:34episode of the Midgame Mindset. Thanks for joining us on the Midgame Mindset. If today’s episode sparked a new idea or
54:40[music] helped shift your perspective, share it with someone who’s ready to grow. Subscribe, leave a review, and
54:45keep playing the [music] game. With the right mindset, the best moves are still ahead. Until next time, keep changing
54:50the game.
