Episodes

The fair ends, the camper finally gets quiet, and that’s when the real recap starts. We’re coming off the Windsor Fair run on fumes, talking through what it’s like to bounce from location to location just to keep the podcast going and keep the business moving. We share the honest behind-the-scenes of fair season life: long days, short sleep, parenting on the road, and the weird mix of pride and pressure that comes with chasing the biggest event of the year. We also break down why Windsor contin...

We’re back on the Loud Proud American Express, parked for once, recording a late-night campground session at the Windsor Fair. The vibes are calm, but the stories are not. If you’ve ever wondered what life looks like when a small business owner is living on the road, working fairs, chasing better stops, and trying to stay grounded, this one puts you right in the passenger seat. We start with Buffalo road stories that sound made up until you remember fairs bring out every kind of human behavior....

The Erie County Fair is over, and we’re back home with that strange mix of relief, gratitude, and frustration you only get after a long road run. We went in with big goals for Loud Proud American, fought through two straight weeks of travel, and still watched sales fall far short of what we expected. Add in wild storms, shelter-in-place alerts, and a crowd that showed up but didn’t spend, and you get a real-world lesson in how event vending, pop-up retail, and small business cash flow can flip o...

A 1.2 million-attendee fair is supposed to be the win you’ve been chasing. So what happens when you finally land the biggest event of your business life and the sales barely move? We’re recording from the Erie County Fairgrounds in Hamburg, New York, walking the campground before the day starts, giving you the unfiltered vendor reality of life on the road with Loud Proud American. We talk through the behind-the-scenes details most people never see: the long fair hours, the heat bouncing off the...

The highway is loud, the stakes are louder, and we still hit record. We’re rolling south on I-90 in the Proud American Express, headed for the Erie County Fair in Hamburg, New York, and we’re doing it on limited sleep, last-minute repairs, and sheer commitment to keep the podcast streak alive. If you’ve ever tried to build a small business while life keeps moving, you’ll recognize every ounce of this pressure. We talk through the behind-the-scenes reality of preparing for a major vendor event: ...

I’m running on almost no sleep while we race toward the biggest opportunity Loud Proud American has ever had, and I’m not going to sugarcoat how heavy it feels. Between inventory debt, vehicle repairs, and family grief, I’m trying to find the silver lining and keep putting one foot in front of the other. • juggling early mornings, parenting, and the reality of burnout • preparing for a massive fair with new vendor requirements and costs • breaking down why inventory is the hardest part of the ap...

A small business doesn’t pause just because the world gets loud. We start by pulling back the curtain on what life looks like right now for Loud Proud American: early mornings in Maine, daddy-daughter duties, piles of apparel to press, designs selling out at the worst possible time, and the stress of gambling on inventory before the biggest challenge in brand history, the Erie County Fair. On top of that, we’re rebuilding the bus again after brake and ABS problems, pouring more money into parts ...

The truck says “Seek Fuel,” the schedule says “Be set up by 8,” and my body says “Go to bed.” That’s the tension running through Episode 315, where I finally answer the cliffhanger questions: did we make it to the show, how did we pull it off, and what did it cost us in sleep, stress, and pride. We’re coming off eight straight weeks on the road as a small business owner, building Loud Proud American one event at a time while trying to keep family life steady. I break down the real logistics peo...

Everything is fine until the wheel falls off, the shipment misses the truck, and your calendar has zero open space to fix any of it. We are deep in the real-world grind of small business ownership, where event season does not care if your trailer is broken, your bus is down, or your best-selling sizes are wiped out. I walk you through what it looks like to run an apparel brand on tight timelines, why one vendor weekend can swing your whole month, and how a “make it work” decision can become the ...

The weekend starts with sweat, doubt, and that quiet question every small business owner knows too well: am I really building something here, or am I just burning myself out? I’m coming off America 250 and rolling into Episode 313 with a full recap of a blistering heat wave, a brand-new fair on the calendar, and a milestone I can’t believe I get to say out loud, six years of Share The Struggle and 313 consecutive weeks with you. I walk through the real vendor life math at fairs and festivals: s...

Only 53% of voters say they’re proud of the country, and that number lands different when you’re staring down America’s 250th birthday. I open by reading the Declaration of Independence, then I get blunt about what it means to be free, to be grateful, and to choose growth when life is heavy. This is a July 4th mindset reset with teeth, not a Hallmark speech. We talk through the pride gap and why it feels like the country is splitting into different realities. I break down capitalism vs communis...

Father’s Day didn’t just make us miss our dad. It exposed a fear we’d been carrying quietly for two years: what if he wouldn’t be proud of who we’ve become under pressure? We talk honestly about the weight of trying to do it all at once running a small business and building a brand, being a husband, learning fatherhood, and taking on the responsibilities our dad used to handle without complaint. Grief doesn’t always look like tears. Sometimes it looks like doubt, anxiety, and that looping quest...

Four hours from home, a brand-new fair, and a plan that looked simple on paper. Then reality hit: 90-degree heat, a solo tent setup, black flies so thick they sounded like rain, and four nights trying to sleep in the back of a Yukon because the camper wasn’t an option. We’re telling the whole road story from Springfield, Maine, from the small-town moments that restore your faith in people to the kind of setbacks that make you question why you even signed up. Along the way, we break down how we ...

Rejection emails are one thing. Rejection that makes you question your identity, your message, and your future is something else. We’re coming off a week that started with baptism and ended with two moments of real relief, and we’re telling the full story, messy parts included. We talk through the “season of new” around Loud Proud American: taking bigger swings for America 250, applying to major concerts and country festivals, and pulling back from familiar local events even when they used to b...

We waited a long time for baptism day, and when it finally arrived, it didn’t feel like a single moment. It felt like a whole season coming to a head: grief, healing, late-night doubts, and the decision to stop “faking fine” and start living our faith out loud. This recap is personal, funny in the way real life is funny, and honest about how heavy a joyful day can still feel. We talk through the people who showed up for us and the kind of church community that’s built on effort, not convenience...

We almost talked ourselves out of a new Memorial Weekend event because it wasn’t the “guaranteed” move. The warnings, the what-ifs, the fear of the unfamiliar, all of it started steering the wheel. Then we showed up, set up shop, and realized how wrong we were. What we found was a family environment, promoters who actually value vendors, and the kind of customer energy that reminds you why you started in the first place. We break down the real entrepreneurship lesson hiding inside a weekend rec...

Comfort can start as a blessing and end up as a cage. After a packed weekend of vendor events for Loud Proud American, we take an honest look at what growth really costs when you’re building a small business, raising a family, and trying to keep your faith strong while the next step still feels unclear. I break down why those “good weekends” matter so much, not just for sales, but for momentum, community, and the motivation to keep showing up. Then things get real: I share the first time in six...

One unexpected message can hit harder than a year of planning. After grinding through the messy middle of building Loud Proud American, I got a note from a mentor in the apparel world: “I’d like you to speak to my class.” That single ask turned into a full circle moment that gave me a boost of confidence I didn’t even know I needed, and it forced me to look at my struggle in a totally different way. We dig into why sharing your story is not oversharing, it is survival. When you keep the hard st...

She signs up for a women’s conference with barely any details, walks in alone, and ends up walking out with something most of us spend years chasing: relief. Allie joins me for a real, funny, and vulnerable talk about what it looks like when faith stops being an idea and starts becoming a decision, especially when you’re carrying grief, old stories, and the labels you never asked for. We break down what she heard and felt at the conference, including teaching from the Book of Ruth and the chall...

An attempted assassination on a president should stop a nation in its tracks, not blend into the weekend like background noise. We sit with that chilling “new norm,” then ask the harder question: what are we doing to each other with the way we talk, post, mock, and accuse? We trace how political violence, conspiracy theories, and media rhetoric collide in real time. When leaders and influencers pour gasoline on polarization, someone out there eventually treats it like permission. We also confro...

A year can pass in a blur, and then one date cracks everything open. We sit down again, husband and wife, to revisit the phone call she dreaded for years: the one that told her the police needed her to identify her mother. What follows is an unfiltered conversation about addiction, homelessness, the overdose crisis, and the brutal reality of being the child left behind, still loving someone who couldn’t stop hurting themselves. We talk about what happens when a death gets treated like routine p...

We juggle a sick kid, zero sleep, and a late-night recording, then land on the one story we promised: how Good Friday and Easter Sunday reshaped our faith. We talk about grief after suicide loss, the power of being prayed over, and why hope only works when it’s placed somewhere solid. • recording on fumes after a rough sick-day spiral • why we commit to Good Friday and Easter services • feeling drawn to church and finally feeling at home • parenting pressure when there’s no childcare • choosing ...

Episode 300 hits on a day that feels bigger than a calendar date. I’m looking back at six years of the Share the Struggle Podcast, 300 consecutive weeks with no hiatus, no missed shows, and no hiding from the messy parts of building a life. If you’ve ever felt stuck, tired, or unsure, the core idea is the one that keeps me moving: everybody struggles, but you decide whether you go through it or grow through it. That choice shows up in your habits, your relationships, and the future you’re quietl...

I didn’t expect a 24-hour lesson to smack me in the face, but it did: wake up in Maine and go to bed in Texarkana, Arkansas, and you realize how much life can fit inside one day. I’m running hot lately, riding deadlines, feeling the walls close in, and trying to claw my way back to solid ground. Then my wife says the simplest thing that changes everything: go. Take the break. Get out of the foxhole for a minute. So we do something ridiculous. Brian Palmolo and I fly out, hit Houston, Uber down ...