The deal that almost killed Jackson Hewitt

Find Your Music and Play It Loud with Jimmy Funkhouser

This conversation with Jimmy stuck with me because it wasn’t really about retail, or gear, or even business strategy. It was about finding the thing you’re meant to play, and having the discipline to keep playing it when it feels like no one is listening. Feral didn’t work right away. There were moments where the numbers didn’t make sense, the market tightened up, and the timing felt brutal. Moving into a bigger space during uncertainty looked reckless from the outside. Inside, it felt like a constant question of whether this thing would ever find its rhythm. What I kept coming back to was how much of Jimmy’s journey came down to listening. Listening to customers. Listening to the community. Listening to what wasn’t working, even when it hurt. Early on, the shop reflected his personal taste and passion. Over time, it turned into something bigger. Something useful. Something that mattered to more people than just him. That’s when the music started to sound right. This episode is a reminder that hard work isn’t just about effort. It’s about alignment. About staying in the game long enough to let feedback shape you without losing the heart of why you started. About putting your head down, doing the work, and trusting that clarity comes after commitment, not before. Most of us don’t need a new idea. We need to play the one we have more honestly, more humbly, and for a lot longer. Keep playing. The song gets better as you go.

Letting Go Without Giving Up with Courtney Clark

“I don’t know that I believe everything happens for a reason.” Courtney Clark didn’t say that lightly. She said it as someone who survived cancer. Then survived it again. And then survived a brain aneurysm that doctors say would have killed her if they hadn’t found it in time. Courtney isn’t interested in shiny optimism or motivational slogans. She’s interested in what actually helps when life breaks the plan you were counting on. At 26, everything made sense. Marriage. A house. A future mapped out. Then came cancer. Then a divorce that didn’t survive it. Then more cancer. Then three brain surgeries in eight days. The goals she had built her life around didn’t just feel hard. They were no longer possible. And that’s where she learned something most of us are never taught. Success doesn’t come from grinding harder on a plan that no longer fits. It comes from adaptability. This conversation is about the difference between grit and wisdom. Between quitting and choosing differently. Between giving up on a plan and believing in yourself enough to aim again. The Lessons: * Adaptability beats blind perseverance * Positivity is an outcome, not a strategy * Letting go of a plan is not giving up on yourself * The most resilient goals are big enough to survive disruption * You don’t have to believe everything happens for a reason. * But you do get to decide what it means from here.

Manifesting Success in the Hardest Seasons with Mark Kuster

What happens when your passion collides with reality? In this episode of Through the Dip, I sit down with Mark Kuster, founder of Work Lab in Grand Rapids, to talk about the highs and lows of building a coworking business from the ground up. Mark shares openly about the massive risks of launching Work Lab, the financial and personal strain it created, and the unexpected challenges of opening a space designed for people to gather—right before a global pandemic. More than that, he dives into the lessons he’s learned about mindset, positivity, and manifesting, and how those practices helped him not only survive the dip but also find fulfillment in the process. If you’ve ever wrestled with self-doubt, financial pressure, or the tension of chasing a dream while balancing family and business, Mark’s story will resonate. This episode is about more than coworking—it’s about what it really takes to keep going when everything around you is telling you to quit.

Hiding My Truth Was Holding Me Back

For a long time, I thought being professional meant holding it all together. Smile. Deliver. Keep your personal stuff out of it. But in talking with Jude Charles, I realized something different: Sometimes, the most powerful thing you can do… is stop hiding. Jude shared a moment I can’t stop thinking about. He was sitting on the edge of his bed, head in his hands, watching his car get repossessed for the second time. Five years into business, he was barely making $20K a year, and then his phone rang. It was a client calling to say the documentary he made for her had just helped her cross $1,000,000 in revenue. He could’ve taken that as proof he didn’t belong. Instead, it became the turning point. Because the difference wasn’t in his talent, it was in what he’d been holding back. This episode is about what happens when you finally let people see all of you. The Lessons: * Show Up Unapologetically and Wholeheartedly  * Your Purpose is Found Through the Process, Not Outside of It * Vulnerability is the Gateway to Human Connection and Leadership Being transparent isn’t a weakness; it’s a strength. It’s the reason people trust you in the first place. Be true to yourself, Steven Listen On: YouTube [https://youtu.be/fU01y-mhtWc?si=dIVf7ADI3Hhk9vUP&utm_source=www.throughthedip.com&utm_medium=newsletter&utm_campaign=hiding-my-truth-from-my-clients-was-holding-me-back] | Spotify [https://open.spotify.com/show/41K9DqhhpUplLoVtDbWAQ9?si=0c87292505c5479f&utm_source=www.throughthedip.com&utm_medium=newsletter&utm_campaign=hiding-my-truth-from-my-clients-was-holding-me-back] | Apple Podcast [https://podcasts.apple.com/us/podcast/through-the-dip/id1766354790?utm_source=www.throughthedip.com&utm_medium=newsletter&utm_campaign=hiding-my-truth-from-my-clients-was-holding-me-back] More on Jude Charles: 💼 LinkedIn [https://www.linkedin.com/in/judecharles?utm_source=www.throughthedip.com&utm_medium=newsletter&utm_campaign=hiding-my-truth-from-my-clients-was-holding-me-back] 🔗 judecharles.co [https://judecharles.co/?utm_source=www.throughthedip.com&utm_medium=newsletter&utm_campaign=hiding-my-truth-from-my-clients-was-holding-me-back] Thanks to This Episode’s Sponsors: 🌎 HustleFish [https://hustlefish.com/services/web-design/?utm_source=www.throughthedip.com&utm_medium=newsletter&utm_campaign=hiding-my-truth-from-my-clients-was-holding-me-back] - Premium website support for premium companies

The deal that almost killed Jackson Hewitt

What if the thing that looks like a once-in-a-lifetime opportunity… is actually a trap? When starting Jackson Hewitt, John thought he struck gold: a deal that would double his company’s footprint overnight. Instead, he inherited unpaid employees, sabotage from the inside, and a cashflow disaster so brutal it nearly took the company down. But here’s the thing, he didn’t quit. He didn’t even flinch. He had to shrink to survive, learn the hard lesson, and come back stronger. This conversation is about:  * Learning when to pivot without abandoning the mission * Why you should never scale without testing small * How to lead through chaos without losing your soul * And why being too early can be just as dangerous as being wrong If you’re building something right now, especially if it feels fragile, uncertain, or like it might break, you need to hear this. Hold the vision. Loosen your grip. Follow The Show: https://throughthedip.com [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbFVQa3FXMWlfY1JIa3RNb0hEWWR0YUpiNTZpUXxBQ3Jtc0treDJEN1QxSk1JME50MEJiNko4bENJcEVqeXVjYTVZdkpuWldtVVZTRmdHVDdzOHdrdWdXRjNycGx4TnU3eE5BR3E1T2htN01mekNhNHJaRThBNHBHXzJCVkthWUg1bE50RDIycDhqMW8zUEh1cmdfcw&q=https%3A%2F%2Fthroughthedip.com%2F&v=p02Jz9Arinw] Show Links: * John Hewitt - LinkedIn [https://www.linkedin.com/in/john-t-hewitt-9917b7149/] * Loyalty Brands [https://loyaltybrands.com/]