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. 3d ago

    You Have the Right Network. You Just Aren’t Using It.

    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 get into burnout (the real kind, not the LinkedIn version), why most hiring and sales processes are broken, and why your network is probably the most valuable thing you have, but you’re not getting paid for it. Beacon is Rob’s answer to that: turning warm intros into actual money. About Our Guest Rob Reznik is the founder of Beacon, a platform designed to help people monetize their network by getting paid for referrals. He spent years in finance and tech, rising to CFO roles and working through multiple company exits before deciding to build something of his own. His experience with hiring, recruiting, and internal referrals led him to see a bigger problem: people create value through their connections every day, but rarely benefit from it. Beacon is his attempt to change that by turning trust and relationships into something measurable and actionable. 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 #StartupLife #FounderJourney #BuildInPublic #Sales #Referrals #Networking #BusinessGrowth #Leadership #CareerPivot #Burnout #Startups #TechFounders #Innovation #Mindset #RealTalk #NoBS #LinkedInGrowth

    42 min

  2. Jun 2

    If Your Kid Called You Out… What Would You Do?

    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 conversation gets into what happens next. Leaving a job you actually like. Walking away from security. Figuring out your value when no one’s assigning it to you anymore. And dealing with the uncomfortable truth that “freedom” comes with pressure most people aren’t ready for. About Our Guest Briana Mascaro is the founder of SOPHOS, where she works with executives and business owners on leadership, HR challenges, and workplace issues. She spent nearly 15 years at Disney in HR and legal-focused roles before starting her own coaching and consulting practice. Today, she helps companies handle complex people problems while giving leaders the clarity to make better decisions. 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/. #entrepreneurship #leadership #founderstory #careerpivot #businessgrowth #mindsetshift #successstories #executivecoaching #startupjourney #personaldevelopment

    40 min

  3. May 26

    What Rob Berk Saw That Everyone Else Missed

    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, and building leverage while everyone else stayed comfortable. About Our Guest Rob Berk is the President of Berk Enterprises, a second-generation family business he helped scale through product innovation and aggressive expansion. He’s known for building unique product lines in the concession industry and being early to global sourcing. He’s also the founder of Pinball Expo and owner of Pastimes Arcade, home to one of the largest pinball collections in the world. 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 #FounderMindset #RealTalk #NoBS #ThinkDifferent #Opportunity #Innovation #Leadership #ScalingBusiness #FamilyBusiness #SecondGeneration #StartupLife #GrowthMindset #BusinessPodcast #SteveCross #Operators #BuildInPublic #RiskTaking #StayHungry #PlayToWin

    50 min

  4. May 19

    The Truth About “Stability” No One Admits

    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 he’s building Arena differently. Not just another wealth firm playing middleman, but actually getting in the game. Direct deals. Real access. Less talk, more participation. And the constant tension of growing something fast without turning into the exact thing you left. About Our Guest Mitch Stein is the co-founder and principal of Arena Private Wealth. He didn’t start as an entrepreneur. He became one after spending over a decade inside the system and realizing it wasn’t built the way it should be. So he left and built his own version. Arena combines traditional wealth management with capital markets and alternative investments, giving clients access to deals they usually don’t get a seat at. Mitch operates like a late-stage entrepreneur; less theory, more reps, and a clear bias toward doing things differently when the default way doesn’t make sense. 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 #BetOnYourself #FounderMindset #StartupJourney #BusinessGrowth #WealthBuilding #InvestingMindset #PrivateWealth #AlternativeInvestments #Leadership #RiskTaking #BuildInPublic #RealTalk #NoBS #OperatorMindset #ScaleSmart #BusinessStrategy #FinancialFreedom

    49 min

  5. May 12

    Ed Kalaher on Why Most Entrepreneurs Are Lying to Themselves

    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+ locations, this conversation is about mindset shifts, hard lessons, and what it actually takes to grow something that lasts. If you think entrepreneurship is a straight line, this episode will fix that fast. About Our Guest Ed Kalaher is the CEO and President of Window Depot, a national dealer network he helped rebuild and scale after acquiring assets out of bankruptcy in 2010. With a background that spans engineering, sales, IT, and executive leadership in the window manufacturing industry, Ed brings over 30 years of experience to the table. Under his leadership, Window Depot has grown from a struggling brand into a nationwide network of more than 90 independently owned locations. Beyond business, Ed is also the author of The Servant and the Savage, a book focused on the mindset required to succeed in both entrepreneurship and life, blending empathy, discipline, and execution. 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/. #Entrepreneurship #BusinessGrowth #Leadership #SuccessStories #FounderMindset #SmallBusiness #ScaleYourBusiness #StartupJourney #BusinessOwner #MindsetShift #GrowthStrategy #CEO #BusinessLessons #Resilience #Sales #Marketing #WealthBuilding #PersonalDevelopment #Podcast

    40 min

  6. May 5

    From Zero to CEO Without a Safety Net

    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 knocking doors to scaling into reconstruction and commercial work, this is the reality behind growth.  About Our Guest Stephanie Sage is the CEO of Sage Restoration, a Kansas City-based company specializing in water, fire, mold, and reconstruction services. She entered the industry with zero experience, built the business through relentless sales and networking, and turned it into a multi-division operation that now includes large-scale reconstruction and commercial work. Along the way, she navigated industry skepticism, scaled through multiple growth stages, and eventually brought her son into the business, where he now leads expansion efforts. 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/. #entrepreneurship #smallbusiness #businessgrowth #founderstory #startupjourney #womeninbusiness #ceomindset #businessowner #leadership #scaling #growthmindset #hustle #sales #networking #restoration #construction #realbusiness #successstories

    37 min

  7. Apr 28

    Max Pennington Built CLEANR to Fix What Everyone Else Ignores

    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: prototypes, patents, manufacturing headaches, investor dynamics, and the kind of failures you don’t see on LinkedIn. This is a conversation about figuring it out as you go, and why “good enough” usually isn’t. About Our Guest Max Pennington is the co-founder and CEO of CLEANR, a company focused on removing microplastics from everyday water systems. With a background in chemical engineering from Case Western, he helped develop a patented vortex filtration system that captures over 90% of microplastics from laundry. CLEANR has already launched its first product and is pushing toward a bigger goal: getting this tech built directly into washing machines and expanding into whole-home water filtration. Max is in the middle of building it, figuring out product, market, and scale in real time. 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 #Startup #BuildInPublic #FounderJourney #HardTech #ProductDevelopment #Entrepreneurship #StartupLessons #CleanTech #Microplastics #WaterInnovation #Sustainability #FutureOfTech #Manufacturing #Startups #BusinessGrowth #Innovation #RealConversations #NoBS

    35 min

  8. Apr 21

    You Don’t Need Talent. You Need Discipline.

    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, money, leadership, and what actually builds trust in business. The conversation centers on responsiveness, accountability, and why most people lose opportunities simply by not doing the basics consistently. It’s a grounded, no-BS look at how success is really built over time. About Our Guest Sean Hackett is the job coordinator at R. Carrozza Plumbing in the Chicago market, where he manages bids, proposals, and project coordination across a wide range of construction work. Before that, he spent years at the Chicago Board of Trade, working his way up from runner to broker and eventually leading a team through some of the most high-pressure financial environments imaginable, including trading during 9/11. That experience shaped how he approaches business today: know your customers, respond fast, stay accountable, and don’t cut corners with other people’s money. His background blends blue-collar industry knowledge, financial market discipline, and a strong belief that relationships (and reputation) are everything. 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/. #Entrepreneurship #StartupStory #BusinessGrowth #FounderLife #WomenInBusiness #SuccessStories  #Leadership #BuildInPublic #Hustle #Mindset #StartupJourney #BusinessPodcast #ScaleUp #NoExcuses

    32 min
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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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