Entrepreneurs Need New Heroes
Christian Rawles on the inner game of running a business, the gap between who you are and who you want to be, and coaching the people building the next big outdoor brands.
Before we dive in today, I wanted to thank all the new subscribers. A lot of you have joined lately and I’m glad you’re here. This Substack talks about the intersection of marketing and endurance: real campaign data, founder conversations, and honest takes on what’s working in outdoor media.
This week’s episode is a little different. It’s less a business-of-endurance conversation and more a serendipitous coaching session that I happened to record. About fifteen minutes in I stopped interviewing Christian and started being coached by him, and I decided to leave that in. If you’ve ever felt the gap between where you are and the person you’d need to become to get where you want to go, this one will land.
Listen to the full conversation: Apple Podcasts · Spotify
This Week’s Episode
Guest: Christian Rawles, executive coach for entrepreneurs and former owner of Ambler Mountain Works (18 years in the outdoor industry).
Why it matters: Christian spent 15 years owning an outdoor brand, sold it, and now coaches founders through the moments that don’t show up in the operating playbook. The fear of success. The gap between this version of you and the next one. The abundance vs. scarcity question that quietly shapes every decision you make.
The takeaway: The conversations entrepreneurs most need to have are the ones they’re least equipped to have alone.
The Path In: Working for Free Until It Pays
Christian’s career started the way a lot of careers in the outdoor industry start. He moved to Canmore, Alberta, knew a couple people who ran small businesses, applied for a job at a hat company called Ambler Mountain Works, and got rejected. Twice. They eventually threw him a bone with seasonal warehouse work, and three years later he and his wife bought the company.
His framing of that period is honest in a way most career stories aren’t:
“I believe that you need to work for cheap or free to do the things that you want to do. All the career inflection points that led up to me doing this, I offered to work for free or cheap to get my foot in that door. And I recognize that to be able to do that, there’s a lot of luck and privilege that entails. So it’s not necessarily a repeatable strategy.”
That’s the rare version of this advice that doesn’t come wrapped in survivorship bias. It’s true and it’s not universally available, both at once.
The Two Reasons People Hire a Coach
Christian categorizes the founders he works with into two buckets. Either they’re bumping their head against the same wall over and over and don’t know why, or they know exactly who they want to be and feel a chasm between that person and the one they currently are.
The work in the second case is mostly about getting clear on what you actually want, and whether the thing you’re chasing is yours or something projected onto you by someone else.
The Fear Most Founders Don’t Name
The piece of his recent conversation with Aaron Lutze on Second Nature that hit me hardest was the question of whether the thing you’re really afraid of is failure or success. I asked him to unpack it.
“We can be afraid of the fear of failure while at the same time afraid of the fear of success. Around the fear of success comes the fear of allowing ourselves to become the person we need to be to do that. To be able to reach this, I have to give myself permission to show up in a certain way, or change the way I’m showing up. And that has consequences for our relationship with ourselves, but also with the relationships we have with people in our lives.”
Becoming the next version of yourself isn’t free. The relationships you have were calibrated to the current version. That’s the part nobody tells you.
This is where I stopped interviewing Christian and started talking about the Long Run Labs Network. If I hit my revenue goal this year, I’ll have paid 30+ podcasters at least $30K each. That’s not a number I can take back. Once you’ve put that money in someone’s pocket, you can’t be a one-year wonder. The fear of success there is real and it’s specific: the fear that the version of me who has built something that 30 people depend on is a version of me I don’t yet know how to be.
I told Christian, half joking, “this evolved into a coaching call.” He said, “Let’s do it.” I left the rest in.
The Gap and the Gain
The frame Christian uses for this is from a Dan Sullivan book called The Gap and the Gain. The version I’ll give you is the one he gave me on the show.
We spend most of our time looking forward at the horizon: the ideal life, the ideal business, the ideal version of ourselves. The horizon is useful because it gives us a direction to point the boat. But the gap between where we are and that horizon is where most of us live emotionally, and living in the gap is exhausting because by definition we will never reach it.
The gain is what’s behind us. It’s the distance from where we started to where we are right now.
Christian asked me what 2023-Jonathan would say to current-day Jonathan. The honest answer was: holy shit, look what you’re doing. I’m proud of you. You finally took the leap. Keep going.
He didn’t let me intellectualize past it. He made me sit with the feeling. Pride. Betting on myself. The fact that both of my parents are entrepreneurs and I always pictured myself as one. The disbelief that the consistency actually compounded into something.
“We have a tendency to be looking out upon the horizon as if we’re on a boat. But if we turn around and look backwards from where we are in this moment to where this journey started, that’s the gain. We spend too much of our time living in the gap, looking at the shortcomings, looking at where we’re falling short, as opposed to looking at the gains.”
If you’re a founder reading this, that exercise costs nothing. Set a timer for five minutes. Write down what the version of you from three years ago would say to the version reading this right now. Don’t skip the feeling part. That’s where the work is.
Abundance, in a Handful of Sand
Later in the conversation I asked Christian about scarcity vs. abundance, because I think it’s a topic the endurance industry doesn’t talk about enough. When more people win, more people win. The belief that another founder’s success comes out of your own pile is the most expensive belief you can carry.
His metaphor for it was a handful of sand at the beach.
“If I try to squeeze it and hold it as mine, I just lose it all. But if I hold it really openly, I get to hold more. Easy come, easy go. If I can hold it with an open hand and be grateful for what it is in this moment, it’s going to last me a lot longer than if I try to squeeze everything out of it and keep it for myself.”
The hard part in entrepreneurship, he pointed out, is that we still need the number to go up. Growth matters. Profitable businesses require it. The trick is holding both: the open hand and the rising line.
What Joyful Operators Have in Common
I asked Christian what he sees in the DNA of the founders and people in his life who actually seem joyful, not just successful. His first instinct was confidence, but he caught himself, because confidence has been hijacked to mean swagger. What he actually meant was self-belief. And underneath that, presence.
“The people who seem to have that real understanding of joy can be in this present moment. They’re not fretted about the past. They’re not worried about the future. This moment is good enough.”
When I asked who he’s most impressed by, he didn’t say founders. He said single moms working jobs to keep their kids fed. That answer stuck with me.
What Are You Running From?
I closed by asking him about the three ultrarunner clients he currently has. The thread he sees in them is that they’re achievers. The question he asks them, and that I’d encourage every endurance athlete reading this to ask themselves, is:
“What are you running from?”
Worth sitting with.
Five Takeaways
The fear of success is the fear of becoming someone new. Failure isn’t the only thing that costs you relationships. Success does too, because the next version of you isn’t calibrated to the current ones.
Stop living in the gap. The horizon gives you direction. The gain gives you fuel. Most founders run on the wrong one.
Get specific about what you actually want. Most of what we chase is projected onto us. The work is figuring out which goals are yours and which were inherited.
Abundance is an open hand, not a clenched fist. You can hold more sand by holding it loosely. Same with money, opportunities, and the people in your network.
Entrepreneurs need new heroes. There’s no universal playbook. If you don’t want to exit, don’t exit. If you don’t want staff, don’t have staff. The shape of your business should match the shape of the life you want.
Listen to the full conversation: Apple Podcasts · Spotify
Links & Credits
Guest: Christian Rawles. Book a coaching conversation at christianrawles.com/call.
Referenced: The Gap and the Gain by Dan Sullivan and Dr. Benjamin Hardy. Christian’s recent appearance on Second Nature with Aaron Lutze.
Episode credits: Hosted by Jonathan Levitt. Produced by Emma Benner of Sandy Boy Productions.
This Episode Is Brought To You By
The Huddle. Building a business is isolating. You’re making decisions daily that most people in your life don’t fully understand, and surface-level networking rarely helps. What my co-founders Jason Fitzgerald, Ross Yellin, and I built at The Huddle is different: a peer advisory community for early-stage founders who want real accountability and real conversation. Small cohorts, cross-industry, monthly sessions. Someone in the room will tell you the thing you actually need to hear. In-person in Boulder, virtual cohorts open anywhere. Go to findmyhuddle.com and fill out the application.
Popfly. The creator program platform built for outdoor, travel, and adventure brands. It connects you with the largest community of adventure creators on the planet: people who actually use the gear, live the lifestyle, and have built real trust with their audiences. Affiliate links, discount codes, creator and ambassador collabs, all in one place. If you’re a brand, learn more here. If you’re a creator, sign up here.
If this episode sparked something, share your takeaway on LinkedIn and tag Long Run Labs. And if you’re building something in the endurance space; a brand, a community, a coaching program, I’d love to hear about it.
This will forever change how I hold sand 🙌