Success Stories with Steve Cross

Steve Cross
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

Every entrepreneur has a story. The interesting ones come from people who actually did the work. Success Stories is where Steve Cross sits down with CEOs, founders, and operators who’ve actually done the work. These are honest conversations about building companies—what worked, what broke, and the real decisions behind growth. No hype. No guru energy. Just practical insight for leaders who want clarity and lessons they can apply. If you care about building better companies (& surviving the process) you’re in the right place. Want to be part of the conversation? Hit me up at stevecross.wtf.

  1. 1d ago

    Most Entrepreneurs Learn This Too Late

    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 they're selling, and how AI is completely rewriting the rules for software companies. About Our Guest Sam Hilsman is the Founder and CEO of CloudFruit, a software development and ERP consulting firm specializing in custom software, enterprise systems, and AI-powered solutions. Drawing on experience across healthcare IT, enterprise architecture, and technology leadership, he helps organizations solve complex operational challenges while building products designed to scale. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Entrepreneurship #BusinessGrowth #FounderJourney #Leadership #StartupLife #AI #ArtificialIntelligence #SoftwareDevelopment #EntrepreneurMindset #BusinessOwner

  2. Aug 11

    AI Can't Save a Bad Company.

    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 adapt from the ones that get left behind. About Our Guest Dustin Nimmo is the CEO and co-founder of Gumbo, an AI product studio that helps organizations build AI-powered software, launch digital products, and integrate AI into their businesses. With a background spanning ministry, leadership roles at Procter & Gamble and Kroger Health, and AI product development, Dustin combines technical expertise with a people-first approach to building teams, companies, and lasting impact. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Entrepreneurship #Leadership #ArtificialIntelligence #AI #BusinessGrowth #StartupFounder #BusinessLeadership #Innovation #FounderJourney #TechLeadership #ProductDevelopment

  3. Aug 4

    Success Isn't Freedom. It's More Responsibility.

    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't, how buying businesses became the real goal, and why reputation is still one of the most valuable assets an entrepreneur can build. It's an honest conversation about playing the long game, making better decisions, and defining success beyond revenue. About Our Guest James Miller is the CEO of Color Glo International, a global franchise specializing in the restoration of leather, vinyl, plastics, and fabric. After building a successful construction company and investing in real estate and retail, James acquired Color Glo with a vision of modernizing the nearly 50-year-old brand while expanding its global franchise network and supporting its franchise owners. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Entrepreneurship #BusinessOwner #Leadership #SmallBusiness #BusinessGrowth #CEO #Mentorship #Franchise #EntrepreneurLife #BusinessAcquisition #BuyingBusinesses #FounderMindset

  4. Jul 28

    Legacy Means Nothing If You Screw It Up

    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 teach about leadership, and how trust (not titles) is what actually builds great companies. If you lead people, own a business, or want to build something that lasts, this conversation is worth your time. About Our Guest Jeremy Kerola is the Vice President of UNISERV and a fourth-generation leader of PI&I Motor Express, a family-owned flatbed trucking company founded in 1951. He helps lead the company's operations and growth while focusing on customer service, leadership, and the integration of trucking and steel processing through UNISERV. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Leadership #Entrepreneurship #FamilyBusiness #BusinessLeadership #CompanyCulture #WorkEthic #LeadershipDevelopment #BusinessGrowth #Legacy #FounderMindset #Operations #TruckingIndustry #Manufacturing

  5. Jul 7

    What Nobody Tells You About Selling a Company

    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 being the most valuable. If you're looking for overnight success, this isn't that conversation. It's about what it actually takes to keep going when everything falls apart. About Our Guest Tim Tierney is the founder of TNT Pro Series and a serial entrepreneur who has built, scaled, and exited multiple ecommerce and manufacturing businesses. After selling Mommy Knows Best to private equity and founding Shea Labs, he now helps aspiring founders launch beauty and wellness brands through the Beauty Brand Accelerator, sharing the real-world lessons he's learned from both success and failure. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Entrepreneur #Entrepreneurship #Business #Founder #Leadership #BusinessGrowth #SmallBusiness #Startup #Failure #Resilience #Mindset #PrivateEquity #Ecommerce

  6. Jun 30

    Failure Isn’t Killing You. Quitting Is.

    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't the thing that kills most people: quitting is. They also dive into founding BoardSeye, executive leadership, and what it actually takes to stand out when everyone claims to be an expert. About Our Guest Martin Rowinski is the CEO and co-founder of BoardSeye, a platform that connects companies with board members, advisors, and executive talent. He is also the author of The Corporate Matchmaker and Beyond the Title, focusing on executive leadership, board service, and personal branding. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Entrepreneurship #Leadership #Resilience #NeverQuit #AmericanDream #ImmigrantSuccess #BusinessGrowth #FounderLife #GrowthMindset #PersonalBranding #ExecutiveLeadership #CEO #BusinessPodcast #OvercomingAdversity #StartupFounder #BusinessLessons #SuccessMindset #BoardLeadership #EntrepreneurJourney

  7. Jun 23

    The Real Cost of Keeping the Wrong People

    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, hiring, burnout, scaling people-driven organizations, and why putting the right people in the right seats changes everything. About Our Guest Jenner Feroah is the CEO of Lunatic Fringe, a salon company with corporate and franchise locations across Utah, Idaho, and Ohio. She joined the company in 2002 as an assistant and has spent more than two decades helping grow the brand through a culture-first approach focused on teamwork, accountability, and professional development. Even as CEO, Jenner still works behind the chair one day each week to stay connected to the client and team experience. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Leadership #Entrepreneurship #BusinessGrowth #Franchising #CompanyCulture #SalonIndustry #CEO #SmallBusiness #PersonalDevelopment #TeamBuilding #BusinessPodcast

  8. Jun 16

    Most Entrepreneurs Suck at Hiring.

    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 creating a burnout culture in the process. They also get into cybersecurity, AI, scaling service businesses, hiring failures, company culture, and why entrepreneurship eventually turns into a sales job whether you like it or not. About Our Guest Keith Tessler is the CEO of CMIT Solutions, an outsourced IT and cybersecurity company serving small and mid-sized businesses. Before launching CMIT Solutions, he spent 24 years helping grow a nationwide wedding and media company before moving into executive coaching and eventually returning to entrepreneurship to build his own MSP practice. About Success Stories Welcome to Success Stories, the podcast where Steve Cross sits down with the sharpest minds in business to unpack what it really takes to grow. From scrappy upstarts to category leaders, each conversation reveals the mindset, strategies, and personal stories behind bold decisions and breakthrough moments. No fluff. No gurus. Just real founders, real operators, and real results. If you're a growth-obsessed entrepreneur, marketing leader, or future founder, this playlist is your shortcut to hard-earned wisdom from those who've built it, scaled it, and lived to tell the tale. 👉 Subscribe to the channel and hit the bell so you never miss an episode. 👉If you think you can hang, this link is for you. https://stevecross.wtf  👉 For more about iSynergy and how we help brands grow through strategic digital marketing, visit https://isynergy.io/connect/. #SuccessStories #Entrepreneurship #Leadership #Cybersecurity #BusinessGrowth #MSP #AI #FounderStory #SmallBusiness #BusinessPodcast #CompanyCulture #Sales #Hiring #EntrepreneurMindset #TechLeadership

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About

Every entrepreneur has a story. The interesting ones come from people who actually did the work. Success Stories is where Steve Cross sits down with CEOs, founders, and operators who’ve actually done the work. These are honest conversations about building companies—what worked, what broke, and the real decisions behind growth. No hype. No guru energy. Just practical insight for leaders who want clarity and lessons they can apply. If you care about building better companies (& surviving the process) you’re in the right place. Want to be part of the conversation? Hit me up at stevecross.wtf.

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