Success Stories with Steve Cross

Pedro Vasconcelos started selling video games online as a kid, lost $30,000 in the stock market, left electrical engineering, and built PitchYes—an AI voice-calling company in Brazil. He joins Steve Cross to talk about customer support, voice AI, expansion across Latin America, fundraising, leading by example, and learning to like the hard parts of entrepreneurship.

Most companies want AI to fix their problems before they’ve done the harder work of cleaning up the mess underneath them. Shane Chalupa says that’s backwards. In this episode of Success Stories , Steve Cross sits down with Shane, co-founder of Obnovit, to talk about leaving a Fortune 500 engineering career, building a business with his wife, and helping companies simplify AI instead of getting dis...

Matt Guse didn’t have a business degree. He barely knew how to machine. What he did have was a chip on his shoulder and a refusal to take no for an answer. That helped turn a machine shop in his dad’s garage into MRS Machining, a nationally recognized manufacturer celebrating 40 years in business. Matt sits down with Steve Cross to talk about the failures nobody brags about, a $150,000 business le...

Most people see a broken system and bitch about it. Andrew Hess decided to build something better. In this episode of Success Stories , Steve Cross sits down with Andrew, owner of Hess Solutions, to talk about leaving the employee mindset behind and building a machine shop around quality, integrity, and actually giving a damn about the customer. They get into CNC machining, prototyping, 3D modelin...

Most parents have no clue what their kids are actually being exposed to online. The scary part? A lot of the people who built this stuff are worried, too. In this episode of Success Stories , Steve Cross sits down with Sarah Gallagher Trombley, founder of Digital Mom Media and former Snapchat employee, to talk about raising kids in a world dominated by screens. They get into social media, post-COV...

Dave Hataj grew up in a gear shop because that’s what his family did. No grand career plan. No polished path to success. Just work. In this episode of Success Stories , Steve Cross talks with the owner of Edgerton Gear about taking over a dysfunctional family business, getting his ass kicked trying to change its culture, and realizing that being good at your job means nothing if you’re miserable t...

Jozsef Bogdan came to Canada with $200, one suitcase, and no English. Now he’s trying to turn wasted industrial heat into usable electricity. In this episode of Success Stories, Steve Cross talks with the NISO Energy founder about starting over at 35, chasing a technology that didn’t work, spending years in R&D without revenue, and refusing to quit. They dig into what NISO is building, the ugl...

Georgia Rittenberg answered a Craigslist ad for a part-time customer service job. Less than five years later, she was running the company. In this episode, Steve Cross talks with Georgia about going from customer service to CEO, learning leadership the hard way, hiring people you might have to fire, and knowing when to stop taking everyone else’s advice and trust your gut. They also get into scali...

Brandon Bornancin grew up broke, made millions, bankrupt a startup, walked away from a million-dollar sales career, and spent three years struggling while trying to build Seamless. AI. In this episode, Steve Cross and Brandon get into what building a $250M company actually costs: the failed businesses, brutal hours, lost friendships, bad hires, scaling problems, and the decision to keep going when...

Most people build a career by following a plan. Sam Hilsman built his by chasing problems nobody else wanted to solve. In this episode of Success Stories, Steve Cross sits down with the CloudFruit founder and CEO to talk about what actually happens when you stop playing it safe. They dive into corporate complacency, the messy reality of entrepreneurship, why most founders build before anyone wants...

What do ministry, entrepreneurship, and AI have in common? More than you'd think. In this episode of Success Stories , Steve Cross sits down with Gumbo CEO Dustin Nimmo to talk about building companies that actually put people first while embracing AI without buying into the hype. They dig into leadership, culture, entrepreneurship, and why curiosity (not fear) is what separates companies that...

Entrepreneurs don't fail because they lack ambition. They fail because they chase the wrong thing. In this episode of Success Stories, Steve Cross sits down with James Miller to unpack the decisions that took him from swinging a hammer to leading a global franchise company. They talk about why James walked away from a thriving construction business, what mentors taught him that books couldn&#3...

Most people think family businesses survive because of the family name. They don't. They survive because every generation earns the right to carry it forward. In this episode of Success Stories, Steve Cross sits down with Jeremy Kerola, Vice President of UNISERV and fourth-generation leader of PI&I Motor Express. They talk about the weight of legacy, why comfort kills growth, what sports t...

Most people love talking about their wins. Tim Tierney would rather talk about the failures that made them possible. In this episode of Success Stories, Tim sits down with Steve Cross to unpack the real story behind building and selling multiple businesses. They get into entrepreneurship, bipolar disorder, bad partnerships, private equity, Bitcoin, and why some of the most expensive lessons end up...

Martin Rowinski's story starts with escaping communist Poland at nine years old, living in Italy while his family fought to get into America, and showing up to school without speaking a word of English. In this episode, Martin joins Steve Cross to talk about resilience, entrepreneurship, surviving the 2008 mortgage crash, building and exiting businesses, personal branding, and why failure isn&...

Most people don't expect a hairstylist to end up running a multi-location franchise company. Jenner Feroah did. In this episode of Success Stories, Steve Cross sits down with the CEO of Lunatic Fringe Salons to talk about turning a passion into a career, growing from salon assistant to CEO, and building a business that refuses to compromise its culture. They get into leadership, franchising, h...

Keith Tessler learned a lesson most founders eventually figure out the hard way: Technology isn’t the hard part. People are. In this episode, Steve Cross sits down with Keith Tessler, CEO of CMIT Solutions, to talk about getting thrown into leadership in his 20s, helping modernize a family business during the PC revolution, learning leadership through mistakes, and building an IT company without c...

Most people know their career doesn’t fit. They just don’t do anything about it. This episode is what it looks like when someone finally does. Steve sits down with Rob Reznik, founder of Beacon, to break down how a CFO with multiple exits walked away from a “successful” path to go fix something everyone complains about but nobody actually solves: referrals, trust, and how deals really happen. They...

This one’s about realizing you built a life that looks right but feels off. Briana Mascaro followed the script perfectly, going to law school, climbing the corporate ladder, and working for 15 years at Disney. Then three things hit at once: a brutal self-check, a colleague gone overnight, and her 8-year-old telling her she wasn’t where she was supposed to be. That’s what cracked it. This conversat...

This one’s a reminder that most people aren’t stuck. They’re just not looking hard enough. Steve sits down with Rob Berk, President of Berk Enterprises, and the story isn’t some clean, step-by-step playbook. It’s a guy walking county fairs, noticing nobody gives a shit about better cups… and turning that into a business edge. It’s flying to China before it was normal, figuring it out in real time,...

This one’s about what happens when you realize the “safe” path isn’t actually safe, it’s just comfortable. Mitch Stein spent 15 years doing everything right (stable career, solid income, clear path),and still walked away from it. Not because it failed… but because it felt limited. This conversation gets into what that actually looks like when you make the jump later in life. We also get into how h...

Most people think success is about hitting some milestone. Ed Kalaher doesn’t. In this episode, he breaks down how his real turning point came decades into his career when he stopped chasing what success should look like and started owning what he’d already built. From grinding through 9/11, the Great Recession, and COVID, to rebuilding a company out of bankruptcy and scaling Window Depot to 90+ l...

Stephanie Sage doesn’t sugarcoat entrepreneurship. After the 2008 crash wiped out her mortgage career, she started a restoration business with zero experience, no paycheck for years, and nothing but hustle to survive. This episode breaks down what it actually takes to build something from nothing: early mistakes, brutal learning curves, and the moments that finally moved the business forward. From...

Most people don’t think twice about doing laundry. Turns out, it’s one of the biggest sources of microplastic pollution on the planet. In this episode, Steve Cross sits down with Max Pennington, co-founder and CEO of CLEANR, to break down how a random discovery turned into a real company solving a real problem. They get into what it actually looks like to build a physical product from scratch: pro...

This episode flips the typical “success story” on its head. Sean Hackett didn’t follow a clean, linear path. He went from competitive academics to acting, got knocked off course, learned business the hard way in the Chicago Board of Trade, and eventually found his way into the plumbing and construction world. What you get here isn’t theory; it’s decades of real-world experience around pressure, mo...