Overcoming Challenges and Embracing Failure in Entrepreneurship with Kerry-Ann Powell

Michael Ritsema bought a tech business at the worst possible time—right before the industry collapsed. Three months in, he hadn’t taken a paycheck, had no leads, and had just remortgaged his house to survive. Most people would’ve walked away. Michael kept showing up. Then two deals landed. It changed everything. That persistence didn’t just save the business—it laid the foundation for a thriving IT company, multiple acquisitions, and eventually, full ownership after buying out every partner. Now, he’s passing on hard-earned lessons from the trenches of entrepreneurship: how to survive downturns, grow through uncertainty, and lead with both strategy and empathy. This episode is a blueprint for building a durable business. Michael shares: What it really feels like to face bankruptcy as an owner Why resilience beats perfect timing—every time The warning signs of a bad partnership and how to exit with integrity The real story behind recurring revenue and how it transformed his business Why sales discipline—not talent—is what separates winners The DISC framework that helped him build a balanced leadership team How peer groups and benchmarking took his growth to another level Key Lessons Resilience Over Perfection: Why showing up and staying in the game often wins over strategy alone. Own the Risk: How betting on himself—and later, buying out partners—gave him full control of his business destiny. Sell Like a Pro: Why disciplined follow-up and consistent outreach will always outperform the latest sales “hack.” Recurring Revenue = Freedom: How pivoting from hardware to services gave him stability through volatile markets. Know Thyself: Why self-awareness and emotional intelligence are must-haves for long-term leadership. Host: Tyler Martin, Think Business with Tyler Podcast Ready to stop riding the financial rollercoaster and build a business that lasts? 📅 Book a Strategy Callhttps://calendly.com/tylermartin/strategy 🎧 Subscribe: ThinkBusinessWithTyler.com Follow Tyler: 🔗 LinkedIn 📸 Instagram ▶️ YouTube 🎵 TikTok Learn more about your ad choices. Visit megaphone.fm/adchoices

Robert Bush Jr went from investment banker managing $30B deals to "coffee salesman with a cause," then built a business model that's reshaping how celebrities create global impact. But when his NBA legend partner Dikembe Mutombo was diagnosed with cancer, and a global pandemic shut down international supply chains, he discovered what truly matters in business... Not celebrity endorsements or fancy marketing—but systems that outlast any individual and purpose that weathers any storm. Now, he's creating the blueprint for how mission-driven companies can transform entire industries while maintaining financial resilience. This episode is a masterclass in building businesses with genuine impact. Robert reveals: * Why starting in a recession is the ultimate competitive advantage * How to scale impact-driven businesses without sacrificing profitability * The shocking way COVID created unexpected partnerships that became long-term assets * Why "sharpening your blade" during crisis reveals who's really built to succeed * The metaphor exercise that transforms how entrepreneurs approach challenges * How NBA stars are now studying his model to create their own legacy businesses * The triple bottom line approach that balances people, planet and profit Key Lessons Coffee as Catalyst: How a humble beverage became the vehicle for transformative social change across continents. Crisis-Proof Planning: Why "always expect a shock" became the foundation of their business model—and saved them when tragedy struck. Resilience Through Humor: The wagon spring philosophy that prevents entrepreneurs from being thrown off course. Beyond Celebrity: How to build brands that transcend individual personalities and create lasting impact. Purpose-Driven Profit: Why solving meaningful problems naturally generates sustainable returns. Host: Tyler Martin, Think Business Podcast Struggling to scale profitably? Let's talk: 📅 Book a Strategy Call https://calendly.com/tylermartin/strategy 🎧 Subscribe: ThinkBusinessWithTyler.com Follow Tyler: 🔗 [Linkedin: http://linkedin.com/in/thinktyler) 📸 Instagram: http://instagram.com/think_tyler ▶️ YouTube: https://www.youtube.com/@thinktylercfo TikTok: http://tiktok.com/@thinktyler Learn more about your ad choices. Visit megaphone.fm/adchoices

Chuck Blakeman Built 13 Businesses Across 4 Continents—Then Discovered Why 99% of Entrepreneurs Fail Chuck Blakeman was told he’d never be employable—so he built 13 businesses in 10 industries instead. But after decades of grinding, he realized the real reason businesses fail isn’t cash flow, competition, or even bad luck… It’s because the owner gets tired. Now, he teaches entrepreneurs how to break free from the "American Nightmare"—scaling businesses that give them freedom, not just income. This episode is a mindset reset for anyone stuck in the daily grind. Chuck reveals: Why "making money" is killing your business (and what to focus on instead) The #1 financial killer of healthy companies (hint: it’s not lack of profit) How to stop selling to strangers and 10X revenue by serving your existing network Why employees are a bad idea—and what to hire instead The Africa disaster that cost him everything (and the one risk rule he broke) How Richard Branson built a empire without reading a P&L "Patient ambition"—why slow, profitable growth beats hyper-scaling Key Lessons From "Income Producer" to Business Owner: Why most founders don’t actually own a business—they own a job. Cash Flow vs. Revenue: How a 2M→ 2M→9M business collapsed (and how to avoid it). Sell Less, Earn More: Why successful companies stop selling and start serving. The Partnership Trap: "The worst form of business… unless it works." The 3to5 Club: Where entrepreneurs finally say, "I don’t know" out loud. Host: Tyler Martin, Fractional CFO & Business Coach Struggling to scale profitably? Let’s talk: 📅 Book a Strategy Call Full Show Notes: ThinkTyler.com/chuck-blakeman 🎙 Subscribe: ThinkBusinessWithTyler.com Follow Tyler: 🔗 LinkedIn | 📸 Instagram | ▶️ YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

John St. Pierre built a $55M business, raised $20M in private equity… and was fired from the company he co-founded just six months later. But instead of walking away, he turned that gut-wrenching moment into the foundation for a new $100M+ business — built patiently, profitably, and on his terms. This episode is a raw, no-fluff masterclass in scaling smart, protecting your equity, and bouncing back when everything crashes. Through real-life lessons and battle-tested strategy, John breaks down how to grow without losing control — and why most founders don’t realize they’re vulnerable until it’s too late. • Getting fired from his own company after raising $20M • How losing everything led to a $100M comeback • Building self-financeable growth instead of relying on outside capital • Creating a 30-year life plan and aligning business decisions to it • Moving from CEO to Chairperson to unlock true strategic scale • Why founders must protect their cap table early • The danger of shiny object syndrome and how he overcame it • The real cost of burnout and over-scaling • How to forecast, protect cash, and build margin visibility • Why “patient ambition” beats hyper-growth every time My Links Host: Tyler Martin , Fractional CFO and Business Coach Having challenges scaling and growing your business? Book a meeting with me: https://calendly.com/tylermartin/strategy Link to show notes: https://thinktyler.com/podcast_episode/power-to-powerless-john-st-pierre/ Podcast: ThinkBusinesswithTyler.com  Linkedin  Instagram  YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

Paul Shrater went from selling a million-dollar Hollywood script to building a multi-business empire that powers product brands for celebrities, creators, and even NASA. His journey is a masterclass in grit, innovation, and scaling smart systems that run without the founder. Through bootstrapping, operational focus, and saying “no” to bad deals — Paul proves you don’t need outside money or hype to win big. • Turning rejection from manufacturers into a thriving fulfillment and co-packing company • Bootstrapping his first eComm business from four shelves and a computer • Helping celebrities and influencers turn passion into scalable product brands • Partnering with creators to build legacy income streams beyond their 15 minutes of fame • Navigating the TikTok Shop explosion and how it’s threatening Amazon’s dominance • Embedding product into entertainment to create viral, high-converting content • Structuring equity partnerships based on value, not just fame • Designing cross-training systems so his businesses run without him • Using cultural awareness and empathy to lead teams more effectively • Shipping fruitcake to space — and turning it into a case study in creative problem solving My Links Host: Tyler Martin , Fractional CFO and Business Coach Having challenges scaling and growing your business? Book a meeting with me: https://calendly.com/tylermartin/strategy Link to show notes: https://thinktyler.com/podcast_episode/hollywood-to-hustle-paul-shrater/ Podcast: ThinkBusinesswithTyler.com  Linkedin  Instagram  YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

Dan Soviero shares his journey from depression and near-death to building a multi-business sports empire focused on impacting over a million kids through athletics. Through grit, purpose, and structured leadership, he transformed rock bottom into a mission that’s driving explosive growth and cultural excellence. • Surviving a suicide attempt at 16 and finding purpose through coaching youth sports • Starting a lacrosse training business at 16 and scaling to five sports-focused companies • Solving a broken uniform industry with 15-day shipping and 99.7% accuracy • Building high-performing teams with EOS and a custom Culture by Design system • Using personality assessments to ensure cultural fit in every hire • Investing in personal development to double productivity across payroll • Teaching leaders to remove ego and drive alignment through self-awareness • Empowering departments to collaborate like a unified sports team • Staying relentlessly curious and asking questions to unlock growth • Serving others as the foundation for lasting success and fulfillment My Links Host: Tyler Martin , Fractional CFO and Business Coach Having challenges scaling and growing your business? Book a meeting with me: https://calendly.com/tylermartin/strategy Link to show notes: https://thinktyler.com/podcast_episode/gun-didnt-fire-dan-soviero/ Podcast: ThinkBusinesswithTyler.com  Linkedin  Instagram  YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

Jared Rosenthal shares his incredible journey from corporate CEO to launching Health Street—starting with a self-painted RV and scaling it into a nationwide drug and DNA testing business. He reveals how relentless grit, late-night emergencies, and hands-on hustle led to a tech-powered company serving over 50,000 clinics across the U.S. • Left a CEO role to start mobile drug testing out of a used RV • Branded his RV with “Who’s Your Daddy” for DNA testing and landed a VH1 show • Built a 24/7 business responding to accidents, testing captains and pilots • Taught himself tech from scratch and built custom APIs to automate operations • Scaled from a one-man show to a national network of clinics and corporate clients • Uses inbound marketing and SEO instead of outbound sales for high-margin growth • Self-funded the entire business, balancing reinvestment with sustainable income • Shares emotional stories that shaped his purpose, including stopping an intoxicated pilot • Stresses the value of doing every job—from mopping floors to writing code • Warns against overreliance on Google and stresses the need to diversify marketing Tune in to hear how Jared turned a secondhand RV into a multimillion-dollar platform, built with hustle, purpose, and an unshakable belief in doing the hard things. My Links Host: Tyler Martin , Fractional CFO and Business Coach Having challenges scaling and growing your business? Book a meeting with me: https://calendly.com/tylermartin/strategy Link to show notes: https://thinktyler.com/podcast_episode/drug-testing-dna-jared-rosenthal/ Podcast: ThinkBusinesswithTyler.com  Linkedin  Instagram  YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

Llance Kezner shares his journey from a career layoff to building Millie’s Sipping Broth, a multi-million-dollar brand disrupting the beverage industry. He reveals how he and his wife turned a simple homemade solution into a nationwide retail success, landing deals with Walmart and Sam’s Club while maintaining product quality and innovation. • Pivoted from a corporate career to launching a food business with no prior industry experience • Created a new product category—broth in tea bags—for convenient, healthy sipping • Successfully funded their idea through Kickstarter, gaining early market validation • Scaled from kitchen production to nearly 3,000 retail locations, including Walmart and Sam’s Club • Overcame competition by patenting a unique manufacturing process • Uses direct-to-consumer sales and strategic retail partnerships to drive growth • Focuses on expanding beyond retail into airlines, corporate offices, and hospitals • Emphasizes product quality and customer engagement, maintaining a personal brand connection • Balances entrepreneurship with strategic planning to ensure scalability and financial stability Tune in to hear how Llance turned a layoff into an opportunity, built a resilient brand, and created a blueprint for product innovation and business growth. My Links Host: Tyler Martin , Fractional CFO and Business Coach Having challenges scaling and growing your business? Book a meeting with me: https://calendly.com/tylermartin/strategy Link to show notes: https://thinktyler.com/podcast_episode/million-dollar-brand-llance-kezner/ Podcast: ThinkBusinesswithTyler.com  Linkedin  Instagram  YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

RT Custer shares his incredible journey from a simple idea on a golf course to building Vortic Watch Company and Colorado Watch Company, reviving American-made timepieces. He reveals how he scaled a niche business, fought and won a six-year legal battle against Swatch Group, and is now expanding U.S. watch manufacturing to new heights. • Transformed antique pocket watches into high-end wristwatches, creating a unique business model • Battled and defeated Swatch Group in a landmark trademark case, protecting the right to upcycle • Scaled Vortic Watch Company despite limited supply, maintaining exclusivity and high demand • Launched Colorado Watch Company to bring modern, American-made watches to a larger market • Balances passion for craftsmanship with strategic financial and operational growth • Emphasizes the importance of sales skills, resilience, and hiring the right team to scale a business • Uses direct-to-consumer sales, storytelling, and American manufacturing as key brand differentiators Tune in to hear how RT turned a passion for history and craftsmanship into a thriving business, fought against industry giants, and built a brand that champions the American Dream. My Links Host: Tyler Martin , Fractional CFO and Business Coach Having challenges scaling and growing your business? Book a meeting with me: https://calendly.com/tylermartin/strategy Link to show notes: https://thinktyler.com/podcast_episode/a-million-dollar-brand-rt-custer/ https://linktr.ee/thinktyler  Podcast: ThinkBusinesswithTyler.com  Linkedin  Instagram  YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices

Welcome to the show where entrepreneurs spill the real stories behind their success. I’m your host, Tyler Martin, and today we’ve got Connor Paddon -- a guy who dropped out of high school to chase poker dreams, only to build and sell businesses worth millions. But it wasn’t all smooth sailing. Picture this: a deal he thought would make him rich ended up a total bust -- all because he skipped the fine print. That screw-up taught him everything he needed to thrive. From gritty lessons to buying boring businesses, Connor’s sharing it all. Let’s dive in! My Links:  https://linktr.ee/thinktyler  https://thinktyler.com/podcast_episode/one-bad-deal-connor-paddon/ Podcast: ThinkBusinesswithTyler.com  Host: Tyler Martin , Fractional CFO and Business Coach Linkedin  Instagram  YouTube Learn more about your ad choices. Visit megaphone.fm/adchoices