Success Stories with Steve Cross

Steve Cross
  • 5.0 (1)
  • Entrepreneurship
  • 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. 3d ago

    A Boxing Loss Changed How He Defines Success | Kelvin Harrylall

    In 2014, Kelvin Harrylall lost an amateur boxing match and started asking what success actually means. He joins Steve Cross to explain Success Theory, the eight pillars he uses to think about a fulfilling life, and his 10-year rule for goals that take time. Kelvin also shares what he learned after pursuing ownership of Byford Machine-Tool, including the people side of leadership, radical transparency, and why building new customer relationships in manufacturing takes patience. His advice: find your own path and stick with it.

  2. Oct 30

    Can Blockchain Help Prove What’s Real in the Age of AI? | Bayo Okusanya

    Bayo Okusanya went from intern to analyst to the first hire at a venture capital fund, then left to build a company of his own. He joins Steve Cross to talk about founding MPC Labs, blockchain-based data attestation, a venture investment tied to fine-art provenance, and tracking goods through supply chains. They also get into AI-generated content and authenticity, plus the realities of bootstrapping, fundraising, building a team, and learning through the long middle of a company’s growth.

  3. Oct 20

    He Lost $30K, Quit College, and Built an AI Voice Company | Pedro Vasconcelos

    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.

  4. Oct 13

    Before You Add AI, Fix This First

    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 distracted by the hype. They get into engineering, entrepreneurship, family, operations, digital transformation, and why real change starts with understanding how the business actually works.   About Our Guest Shane Chalupa is the co-founder of Obnovit. After earning a mechanical engineering degree and spending 13 years in engineering and engineering management, he and his wife launched Obnovit in early 2023. Today, they help businesses simplify AI, clean up workflows, and integrate new technology into operations in a practical way.   About Success Stories Welcome to Success Stories with Steve Cross — long-form conversations with founders, CEOs, owners, and operators about what it actually takes to build and grow a business. No guru energy. No manufactured inspiration. Just real people, real decisions, real tradeoffs, and lessons earned the hard way. If you want more conversations like this, subscribe and follow along. 👉 Learn more about Steve Cross WTF: https://stevecross.wtf   #SuccessStories #Entrepreneurship #ArtificialIntelligence #DigitalTransformation #BusinessOperations #FounderJourney #MechanicalEngineering #AIReadiness #ProcessImprovement #Leadership

  5. Oct 6

    Every Good Success Story Is Full of Failure

    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 lesson, losing his father and business partner, hiring smarter people, building a culture people actually want to be part of, and why AI isn’t killing manufacturing jobs, it’s changing them. Success looks clean after the fact. Building it sure as hell isn’t. About Our Guest Matt Guse is president of MRS Machining, a precision machining company serving customers across the country. He’s spent decades growing the family business, developing manufacturing talent, mentoring other leaders, and learning plenty of lessons the hard way. He’s also the author of MRS Machining: The Manufacturing Story, which tells the real story behind 40 years of wins, failures, risks, and figuring it out as you go. 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 #BusinessLeadership #FamilyBusiness #AmericanManufacturing #BusinessGrowth #Leadership #ManufacturingIndustry #BusinessLessons #AIinManufacturing #SkilledTrades #EntrepreneurMindset

  6. Sep 29

    Stop Making Cheap Shit That’s Built to Fail

    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 modeling, product development, working 16-hour days, and Andrew’s vision of helping people turn an idea into something they can actually manufacture and sell. About Our Guest Andrew Hess is the owner of Hess Solutions, a Northeast Ohio machine shop specializing in CNC and manual machining, prototyping, product development, and 3D modeling. After more than a decade in the trades, Andrew took Hess Solutions full time with a simple philosophy: make things that lasts and treat the customer like a partner, not a transaction. Now he’s building toward a one-stop shop where entrepreneurs can take products from idea to production. 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 #Manufacturing #CNCMachining #Machining #SmallBusiness #BusinessOwner #ProductDevelopment #Prototyping #AmericanManufacturing #EntrepreneurMindset #MadeInOhio

  7. Sep 22

    Why Sarah Gallagher Trombley Walked Away From Big Tech

    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-COVID screen habits, tech regulation, parental peer pressure, and why protecting your kids sometimes means letting them be pissed at you. About Our Guest Sarah Gallagher Trombley is the founder and CEO of Digital Mom Media, an education platform helping parents navigate technology without losing their minds. After a career spanning media and tech, including Flipboard and Snapchat, she turned her insider knowledge into newsletters, courses, speaking, consulting, and coaching for parents trying to make smarter calls about their kids and screens. 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 #DigitalParenting #ParentingInTheDigitalAge #ScreenTime #SocialMediaSafety #KidsAndTechnology #OnlineSafety #BigTech #DigitalWellness #Entrepreneurship

  8. Sep 15

    Stop Hiring for Skill. Start Hiring for Character.

    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 to work with. They also get into the skilled trades crisis, why businesses keep complaining about finding workers instead of developing them, and how Dave turned those lessons into Craftsman with Character, a program now helping companies invest in young people instead of just saying that “nobody wants to work anymore.” About Our Guest Dave Hataj is the owner of Edgerton Gear and founder of Craftsman with Character. After decades of rebuilding his family business and its culture, he’s now handing Edgerton Gear to the next generation and helping other companies rethink how they hire, mentor, and develop people. He’s also the author of Good Work and The Craftsman Code, exploring why character, purpose, and giving a damn about people matter more than another corporate leadership buzzword. 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 #SkilledTrades #BlueCollar #Manufacturing #Leadership #Entrepreneurship #WorkforceDevelopment #CompanyCulture #Mentorship #FamilyBusiness #SkilledLabor #BusinessLeadership

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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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