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 | Spotify | Apple Podcast

More on Jude Charles:
💼 LinkedIn
🔗 judecharles.co

Thanks to This Episode’s Sponsors:
🌎 HustleFish - Premium website support for premium companies

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

Show Links:

• John Hewitt - LinkedIn
• Loyalty Brands

Doug Booth’s company started in a storage unit that was robbed before day one. There was no insurance, no justice, but a new mindset he calls cheerful expectancy, the belief that you show up, even when you don’t know how it’ll end.

A decade later, his company was thriving. Then a major client cut a key contract. Layoffs followed. Fear set in. Doug could’ve let the whole thing crash,but he didn’t.

He stayed in the pilot seat.

He told the truth. Led with compassion. Made hard decisions. And kept flying.

This episode reminded me: Leadership isn’t about avoiding the crash. It’s about not disappearing when it hits.

Show Links

• Doug Booth - LinkedIn
• Multiply Technology 

What do you do when the floor caves in right after you’re handed an award for being the best?

That’s what happened to Dr. Andy Neillie. 

One moment he was flying around the world as a top-tier keynote speaker. The next, he couldn’t afford a plane ticket to the ceremony where he was being honored. 

The speaking gigs dried up, the money disappeared, and the future turned to fog.

So what did he do? He and his wife got re-certified as lifeguards and started one of the first Aqua-Tots franchises.

This isn’t one of those “I just hustled harder” stories. It’s about resilient reinvention. It’s about what Andy calls confident uncertainty, showing up fully today, even when you have no clue what tomorrow holds.

Show Links:

• Andy Neillie - LinkedIn
• Neillie Leadership Group
• Aqua-Tots Swim School

Hi there, my business friends 👋

I sometimes reach a point where I think, “Can I even keep doing this?”

When it’s hard to get out of bed, hard to feel creative, hard to show up.
When the voice in your head whispers that maybe you’re just faking it.

I never had a name for that feeling. But Brian Town gave me one.

In our latest chat, he shares how The Resistance, a term he borrowed from Steven Pressfield, showed up in his business and life.

That quiet force in the background telling you you’re not enough.

The one that shows up every morning, like an uninvited guest.
And here’s the wild part: naming it helped him fight!

There is power in giving something a name.

It gives you the strength to fight it.

This week’s episode is about facing that voice and finding your way through.

Show Links:

• LinkedIn: Brian Town
• Book: “The Lonly CEO - by Brian Town”
• Book: “The War of Art - by Steven Pressfield“
• More about the resistance

In this episode, I talk with Salem Thine about his journey from high school dropout to nuclear Navy success to launching EVA, America's most advanced virtual reality gaming center. Salem shares how he faced a devastating financial crisis when expansion plans fell apart, losing nearly a million dollars in investment commitments, and how he navigated through these challenges with radical transparency.

Resources Mentioned

• EVA Virtual Reality in Flower Mound, TX: https://www.eva.gg/en-US/locations/flower-mound-tx
• "Nobody Cares Unless You Do": https://www.amazon.com/Nobody-Cares-Until-You-Do/dp/1642253200

Sponsored By
This episode is brought to you by Hustle Fish, a digital marketing agency that can get you unstuck and moving forward. If you have questions about where your next customer should come from or how to grow and scale, head over to throughthedip.com/marketing for a free marketing audit. through https://www.throughthedip.com/marketing

I talk with Daryl Starr about his journey from crop consultant to dairy farmer. Daryl shares how his quest to maximize farm profitability led him to create a seasonal dairy operation, only to face plummeting milk prices and mounting debt. His story reveals the emotional and financial toll of entrepreneurial risk, and how faith, grit, and humility helped him navigate through his darkest moments.

Resources 
Daryl Starr's Current Ventrue: https://lev.vc/

Sponsored By
HustleFish - a digital marketing agency that helps you get unstuck and moving forward. Get a free marketing audit at throughthedip.com/marketing

In this episode, I talk with Robert Hunt about his journey from corporate marketing to leading CEO peer groups. Robert shares how discovering his purpose at 50 led to financial crisis—$90,000 in debt—and the pivotal moment when selling his home and taking full ownership transformed his life. His story reveals how accountability can help anyone get unstuck from seemingly impossible situations.

Key Takeaways

00:09 The Debt Spiral: Robert explains how he accumulated $90,000 in debt while maintaining his previous lifestyle, showing how easily entrepreneurs can fall into financial trouble even while pursuing their purpose.

00:22 The Turning Point: After a health scare with vertigo, Robert made the difficult decision to sell his dream home and start over. This moment illustrates his key principle: "Nobody cares until you do."

00:29 Responsibility vs. Accountability: Robert breaks down this crucial distinction: "Responsibility is doing something. Accountability is owning the outcome." This perspective shift is essential for anyone looking to make meaningful change.

Resources 

• Book: Nobody Cares (Until You Do)
• Robert Hunt's CEO peer groups in Dallas, Texas

Sponsored By

HustleFish - a digital marketing agency that helps you get unstuck and moving forward. Get a free marketing audit at throughthedip.com/marketing

Starting a company in your kitchen and watching it grow into a multimillion-dollar enterprise is a dream for many entrepreneurs. But what happens when that dream starts to feel more like a weight on your shoulders? In this episode of Through The Dip, we hear from Brittany Whiteneck, founder of Antique Candle Co., about her journey of scaling a passion project, reaching new heights of success, and ultimately making the bold decision to step aside as CEO so that her company could continue to thrive.

Every business owner hits that inevitable moment. You know the one—progress stalls, goals start slipping, and you begin to question if it’s all worth it.

No matter how much effort you put in, the results just aren’t showing up.

The truth is, the dip isn’t avoidable, it’s an inevitability, and it’s actually there to help you get to where you are going.

The dip isn’t just a roadblock in your journey; it’s a rite of passage.

It’s the universe’s way of asking, “How much do you really want to grow?” And within that challenge, there’s always a lesson—a lesson you can’t bypass if you want to reach the next stage.

I won’t sugarcoat it— when you are in the dip, it’s hard and it’s lonely. I know because I’ve been there.

But when I’ve talked to business owners about going through the dip, they speak about it with a kind of strange reverence.

It’s as if the dip taught them something deeper, something more meaningful, something bigger than just how to run their business.

I want to dig into those experiences to understand what lessons people learned while in the thick of it. What did they find out about themselves, about their businesses, and about life when they were pushed to the brink?

You might expect a podcast called Through The Dip to be heavy, maybe even a little depressing.

After all, we’re talking about some of the toughest times a business owner can face.

But here’s the thing—these stories are anything but depressing.

There is a strong thread of optimum underlying each one. The knowledge that sometimes the lessons we need to learn can only be learned in the hardest of times.

So, that’s what this podcast is about—real stories of real people who’ve been through the dip, who’ve wrestled with doubt, leadership, and loneliness.

Who’ve come out the other side stronger, wiser, and more optimistic than ever.

There’s something deeply human about these stories that touch on things far deeper than just business. 

I am thrilled to have you a part of this adventure! Not just as a listener, but to see the beauty in even the hardest times, to learn from others, and maybe even find your path through the dip.