Founders Journey Podcast

Jimmy Douloumbakas
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  • Entrepreneurship
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Welcome to Founders Journey, a podcast that explores the lives that shape remarkable builders. Each episode features a personal conversation with an entrepreneur who shares early dreams, first jobs, key turning points, lessons from setbacks, and the steady wins that shaped their path. If you want real stories about what forms a founder and what fuels a relentless drive to build, this podcast offers it each week.

  1. 3d ago

    Reid Robinson on Medical Innovation, Recovery, and Starting Over

    Reid Robinson’s story connects recovery, invention, consulting, and entrepreneurial resilience through several major changes in his life. He grew up in Nova Scotia before moving west to Calgary for work. Although his parents taught at universities, Reid initially chose labor jobs instead of higher education. However, a serious head injury eventually changed his direction. He returned home, earned technical certifications, and started building a long career in IT. That career also shaped Reid’s approach to entrepreneurial resilience. As an independent consultant, he learned how different companies manage knowledge, teams, and internal politics. However, Reid rejected the idea of protecting information to make yourself indispensable. Instead, he found that sharing knowledge helped teams accomplish more. What Reid Learned From Consulting Reid also explains how he approached contract negotiations throughout his IT career. First, he focused on proving his value before discussing rates. Then, he used negotiation based on how strongly he wanted each opportunity. As a result, he learned when to push for more and when certainty mattered more. Meanwhile, another event completely changed his direction. In 2015, Reid crashed into a tree on an icy Calgary road. The crash shattered his lower leg and broke his wrist. Over several years, he underwent 13 surgeries while doctors worked to save his leg. Through that process, entrepreneurial resilience became something Reid practiced rather than discussed. Reid Robinson on Building Before Perfect Crutches created another challenge during Reid’s recovery. Because his wrist was injured, conventional options became especially difficult. Therefore, he started thinking about a different way to stay non weight bearing. Reid sketched an idea while recovering and searched existing products and patent databases. When he couldn’t find the concept, he started building it himself. He bought a welder, watched instructional videos, and created his first prototype inside his garage. That early version used modified crutches, aluminum, leather belts, and even an IKEA cutting board. Although the prototype looked rough, it worked. Reid could move without placing weight through his injured leg. More importantly, the experience reinforced his entrepreneurial resilience and gave him something practical to develop. Turning Pain Into Momentum From 2016 through 2021, Reid worked with engineers through repeated design, building, and testing cycles. Eventually, he started selling the device. However, his perfectionist instincts almost delayed that step. A friend encouraged Reid to launch before everything felt finished. Customers started buying the product, using it, and providing feedback. Therefore, Reid realized that waiting for perfection had kept useful information away from him. Ultimately, entrepreneurial resilience doesn’t mean avoiding setbacks in Reid’s story. Instead, it means finding useful action when circumstances become difficult. His experience shows why testing ideas, sharing knowledge, and creating momentum can matter more than waiting. That approach to entrepreneurial resilience connects his recovery, career, invention, and lessons for other entrepreneurs. More From Reid Robinson https://www.xleg.ca https://ca.linkedin.com/company/robinson-exotech-corp https://ca.linkedin.com/in/reid-robinson-441a7837 https://www.youtube.com/watch?v=PnvVTZm7uJQ Chapters 00:00 Why Sharing Knowledge Creates Better Teams 01:09 Reid Robinson and the X Leg Medical Device 08:25 Growing Up in Nova Scotia and Moving West 18:14 How Reid Started His IT Consulting Career 24:29 Building Trust Inside New Companies 29:25 How to Negotiate Consulting Contracts 32:22 The Car Crash That Changed Reid’s Life 49:22 Why Crutches Led to a New Invention 53:11 Building the First X Leg Prototype 59:12 Lessons About Failure Perfection and Progress

  2. Sep 25

    Steve Mack on AI Entrepreneurship Resilience and Building a Life That Fits

    Steve Mack on AI and Better Decisions We start with Steve’s path from enterprise technology into AI-focused entrepreneurship. He outlines Blue Sky AI’s work across products, placements, projects, and AI-enabled systems. He also explains PHIT, which combines wearable data with coaching for health and human performance. However, the conversation quickly moves beyond tools and into how people should use AI. He favors human-centered systems, clear domains, and practical guardrails. As a result, entrepreneurial resilience appears alongside responsible decision-making, not reckless speed. Steve on Sports and Failure Then, we trace his early years in upstate New York, where sports and technology both mattered. Steve played baseball, basketball, soccer, and later college baseball at Drew University. Meanwhile, his parents’ teaching careers reinforced academics and discipline. He connects those experiences to entrepreneurial resilience because sports normalize mistakes, adjustment, and repeated effort. Therefore, failure becomes useful when you learn quickly and move forward. Building Work Around Family Later, the conversation turns to the tradeoffs behind career choices. Corporate consulting brought opportunity, travel, and broad experience, but it also pulled time away from family. So, Steve chose entrepreneurship partly to control his schedule and protect time with his children. He describes Blue Sky AI as a lifestyle business, not a race toward an exit. Still, entrepreneurial resilience matters because freedom requires judgment about clients, projects, and personal limits. Mack on Lifestyle Business Choices Next, we explore how sports, coaching, and parenting shaped his leadership style. He values trying different activities, finishing commitments, and learning without dwelling on mistakes. Because setbacks are inevitable, entrepreneurial resilience depends on staying level through both wins and losses. He also shares why time with family carries more value as children grow older. Ultimately, that perspective changes how he measures a good career and a good life. Systems That Keep Progress Moving Finally, Steve shares the systems he uses to stay focused. He combines current AI tools with simple habits like journaling, notes, whiteboards, and task lists. In addition, he uses EOS to clarify quarterly priorities and longer-term goals. He also delegates finance, reporting, and administrative work when that protects higher-value time. For us, entrepreneurial resilience becomes practical through better systems, clearer priorities, and faster course corrections. The episode closes with a simple idea: keep learning, enjoy the ride, and spend your time where it matters most. More From Steve Mack https://www.phitai.com/ Chapters 00:00 Sports Failure and Entrepreneurial Resilience 01:10 Blue Sky AI and the PHIT Sports Tech Startup 05:35 How Data Can Improve Decisions and Performance 09:20 AI Guardrails and Human Centered Technology 16:15 Sports Childhood and an Early Interest in Tech 24:05 How Sports Prepare You for Entrepreneurship 31:20 Building a Career at Accenture Avanade and IBM 39:10 Why Steve Mack Left Corporate Life 47:15 Building a Lifestyle Business Around Family 56:30 Failure Life Lessons AI Tools and EOS

  3. Sep 19

    Angus Nelson on Founder Resilience Fear and Leading Through Growth at Scale

    When Angus Nelson Says Growth Changes the Founder As companies grow, founders often face more decisions, people, uncertainty, and responsibility. However, the real strain can come from how they respond internally. Angus explains why founder resilience becomes essential when the company changes faster than the person leading it. He argues that strategy alone won't solve a leadership problem rooted in identity, beliefs, and emotional patterns. The Hidden Cost of Carrying Everything Founders can become the bridge between one stage of growth and the next. Therefore, that bridge can become a bottleneck when every decision still returns to them. We discuss how overwork, control, and constant involvement can quietly reduce clarity and presence. Founder resilience requires more than endurance because carrying everything can eventually damage performance and relationships. Why Fear Feels Like Protection Angus describes the Guardian as the internal voice that tries to keep us safe. Yet that protection can keep leaders inside habits that once worked but no longer fit. He connects this tension to the nervous system, subconscious patterns, and the fear of failure. As a result, founder resilience starts with regulating pressure instead of only pushing through it. Nelson on Failure as the Path Forward Failure, in this conversation, isn't the opposite of success. Instead, it exposes what we know, reveals what we don't, and builds empathy through experience. Nelson also explains resilience through the image of shock absorbers adjusting to changing road conditions. That model gives founder resilience a practical meaning grounded in regulation, capacity, and composure. Build the Life Before Chasing the Symbols Later, we explore why people often chase outcomes for the feelings they expect those outcomes to create. Angus shares how his family chose Portugal around the quality of life they wanted. Therefore, the focus shifts from collecting symbols of success to creating joy, peace, and fulfillment directly. This idea also reframes visualization as a way to bring a desired future into present action. What Angus Believes Leaders Must Become The conversation closes with identity, action, and the person required for the next stage. Angus says leaders should focus less on the thing and more on who they must become. Ultimately, founder resilience grows when leaders redefine old stories, expand capacity, and stop waiting for permission. The lesson is simple. Growth asks the company to change, but it also asks the founder to change. More From Angus Nelson BOOK LINKS Amazon https://amzn.to/4baeI1d Barnes & Noble https://www.barnesandnoble.com/w/neuro-resilient-leader-angus-nelson/1149514309?ean=9781636988795 Also available at: Target Walmart Books-A-Million SOCIAL YouTube https://www.youtube.com/@coachangusnelson Instagram https://www.instagram.com/angusnelson Facebook https://www.facebook.com/angusnelson LinkedIn https://www.linkedin.com/in/angusnelson Twitter https://www.twitter.com/angusnelson TikTok https://www.tiktok.com/@angusnelson WEBSITES https://angusnelson.com https://neuroresilientleader.com https://freebook.vip Chapters 00:00 Founder Pressure and Nervous System Regulation 01:16 Why Founders Struggle as Companies Grow 05:07 From Innovation Advisor to Executive Coach 08:11 Why Companies Resist Business Innovation 17:22 How Life Experience Shapes Leadership 26:55 Confidence Fear and Using Your Past 31:48 How Founders Become Business Bottlenecks 35:56 Nervous System Regulation and the Guardian 41:37 Personal Agency Permission and Entrepreneurship 01:01:02 Failure Resilience Capacity and Composure

  4. Sep 11

    How Zech Thomas Built a Business With Hockey, Discipline, and Speed

    Zech Thomas Finds Direction Through HockeyHis path started with hockey, not business. He began at ten, which he describes as extremely late for the sport. Still, he climbed through competitive levels and eventually played junior, professional, and national team hockey. Along the way, hockey taught him repetition, competition, and daily accountability. That foundation shaped the entrepreneurial resilience he later carried into business.When Covid Changed the PlanAfter high school, he expected hockey to remain his main path. However, Covid repeatedly disrupted the opportunities he hoped to pursue. Meanwhile, extra time away from hockey pushed him toward online business experiments. He tried day trading, car washing, window washing, dropshipping, and other e-commerce ideas. As a result, entrepreneurial resilience became practical through constant testing, setbacks, and quick adjustments.Thomas Builds Around a Real ProblemEventually, he focused on a problem he already understood from years in hockey. Players needed sticks, yet high-end options could cost hundreds and break often. So, he built around affordability, durability, and direct relationships with customers. He also leaned heavily on organic social media instead of paid advertising. Therefore, entrepreneurial resilience supported a model built on product knowledge, audience attention, and controlled costs.Learning Through Rejection and PressureDespite early sales, banks wouldn't provide the financing he wanted. Later, he appeared on Dragon's Den and received three offers. He accepted one offer, yet he heard nothing from the investor for a year. Then, he declined the partnership when contact finally resumed. That experience deepened his entrepreneurial resilience and forced him to learn legal, accounting, and operating decisions himself.Zech Moves Fast and Keeps LearningHe also talks openly about struggling in school and learning differently after graduation. During Covid, he read more than 50 books and studied business topics online. Meanwhile, he developed a strong preference for speed over endless preparation. He argues that markets change quickly, so founders need to act before ideas lose relevance. However, he also credits faith, his team, and a clear mission for helping him continue. Ultimately, entrepreneurial resilience connects every stage of his story, from sports competition to business pressure.More From Zech ThomasInstagram: https://www.instagram.com/zechthomass/?hl=enLinkedIn: https://www.linkedin.com/in/zechariah-thomas/Chapters00:00 How Hockey Players Plan Life After High School01:07 How Zech Thomas Built an Affordable Hockey Stick Brand05:06 How Dropshipping Led to Ecommerce Entrepreneurship11:13 Growing Up in Canada With Jamaican Family Roots16:31 Starting Hockey Late and Reaching Higher Levels20:34 Choosing Business After a Competitive Hockey Career22:22 How Covid Created a New Ecommerce Opportunity24:23 What Dragon's Den Taught a Young Entrepreneur29:16 How to Self Fund and Scale a Growing Business33:05 Why Resilience and Speed Matter in Entrepreneurship

  5. Sep 3

    Founder Mindset Lessons on Focus Failure Sales Customers and Better Growth

    Confidence Starts With Action We open with David Wagstaff, who explains how a childhood lemonade stand changed his confidence. First, the lesson isn't that entrepreneurship starts with perfect skill. Instead, action creates experience, and experience can reshape how you see yourself. That founder mindset begins with doing the work before you feel fully ready. He also shows how luck can create momentum. However, he never treats luck as a substitute for effort or creativity. Ownership Requires Sales Allen Kopelman shifts the founder mindset toward ownership, work ethic, transparency, and sales. Next, he explains why employees should treat a business with care, even when they don't own it. He also argues that founders can't avoid selling. Because customers don't appear automatically, entrepreneurs must learn how to communicate value. His point stays practical. Therefore, sales becomes a core operating skill, not a separate department's problem. Failure Needs Reflection and Purpose Alex Jekowsky frames failure as a process for learning, accountability, and better execution. Meanwhile, Kevin Siskar connects founder mindset with purpose, passion, and founder market fit. Alex argues that failure matters only when you study what happened and change what you do. Kevin adds that founders need enough personal commitment to keep going when the work gets difficult. Together, they push past simple motivation. Instead, they emphasize reflection, mission, self-awareness, and deep knowledge of the problem. Customers and Focus Decide What Survives Kobi Simmat brings the founder mindset back to customers, cash flow, and validation. He argues that customers should fund growth whenever possible. Then, David Kidder explains why focus compounds into value over time. He warns that too many options can produce mediocre work and unnecessary complexity. Likewise, both conversations favor solving meaningful problems for customers who value the result. Ultimately, progress comes from demand, discipline, and consistent execution. Scale Needs Structure and Story Paula Skaper expands the founder mindset into leadership systems, customer obsession, and foresight. She explains why leaders need structures that support growth without losing sight of changing conditions. Finally, Park Howell shows how storytelling helps people understand a business journey. He connects the hero's journey to customer journeys, founder journeys, and clearer communication. As a result, the episode closes on a wider lesson. Strong businesses grow when founders learn, focus, serve customers, adapt, and explain why their work matters. Chapters 00:00 Confidence grows through action 02:22 Childhood business lessons and early selling 06:52 Owner mindset transparency and sales skills 13:52 How to learn from failure and execute better 20:43 Purpose passion and founder market fit 27:30 Customer validation cash flow and bootstrapping 34:20 Focus creates value over the long term 41:08 Customer obsession and scalable growth systems 48:03 Storytelling through the hero's journey 52:00 Why the founder is central to the business story

  6. Aug 27

    Cory Blumenfeld on Delegation Resilience and Building Stronger Businesses

    Delegation Beyond the Task List We start with a practical question many founders face. What should you keep, and what should you hand off? He argues that nearly every role can become delegable without making the founder irrelevant. Instead, leaders should build systems that keep moving when they step away. That idea frames his view of entrepreneurial resilience and sustainable leadership. Cory Blumenfeld on Building Roles Around Outcomes He explains why task-by-task outsourcing often creates weak ownership. Therefore, he prefers clearly defined roles with measurable outcomes. Repetitive work can move to AI, while people manage the systems and judgment around it. Meanwhile, those people can adapt when the work changes. For him, entrepreneurial resilience also means designing roles around responsibility, not endless checklists. So, an operations manager owns an outcome instead of waiting for isolated instructions. Where Financial Pressure Shaped the Journey Later, entrepreneurial resilience shows up in his personal story. He grew up in Toronto with loving parents and recurring financial pressure. He also describes being bullied, then learning persistence and empathy from those years. However, he originally planned to become a doctor because medicine represented stability and service. An entrepreneurship course changed that direction. Soon, he saw business as another way to help people at scale. What Cory Learned From Two Healthcare Startups His first technology company digitized hospital discharge information and taught him how businesses actually work. Then, his next healthcare venture began with medical tourism and hair transplants. COVID stopped travel, so the team reconsidered the underlying problem. Instead of protecting the original idea, they followed patient conversations toward healthcare costs and financial planning. That pivot became another test of entrepreneurial resilience, guided by data rather than attachment. Content Confidence and Being Seen After his second exit, he started creating content because he wanted to become more visible and confident. At first, he posted slowly. Then, consistent LinkedIn writing helped him build confidence and uncover a new business direction. Still, he stresses that content should start with what you can discuss consistently. However, he believes founders increasingly need to create content and communicate publicly. Blumenfeld on Fulfillment and Finding Your Easy He closes with two ideas he has literally tattooed on his body. First, have the most fun means choosing work that brings fulfillment. Second, find your easy means finding hard work you can keep doing because it fits you. Ultimately, entrepreneurial resilience connects every lesson in this episode. Put yourself out there, delegate with intention, and keep doing work that feels fulfilling. More From Cory Blumenfeld https://www.linkedin.com/in/coryblumenfeld/ https://bluemoso.com/ Chapters 00:00 From Stability to Entrepreneurship 01:08 Outcome Based Delegation for Business Owners 04:47 How a Virtual Assistant Sparked a Business Idea 10:47 Humans Versus AI in Business Workflows 14:19 How to Build a Business That Runs Without You 18:12 Childhood Struggles and Entrepreneurial Drive 31:58 Lessons From a First Healthcare Startup 35:47 How COVID Forced a Healthcare Business Pivot 42:17 LinkedIn Content and Founder Confidence 47:32 Fulfillment and Finding Your Easy

  7. Aug 20

    Haren Bhakta Explains Founder Ownership Investing and Skin in the Game

    Why Haren Looks at Who Owns the Company We open with a simple investing question. Who actually owns the companies that investors trust with their money? Haren explains why founder ownership shapes how he evaluates public companies. Specifically, he looks for leaders with meaningful personal stakes in the businesses they run. As a result, those leaders feel both the upside and downside of their decisions. He also explains how Warren Buffett inspired his thinking about ownership, leadership, and long-term investing. Bhakta on Skin in the Game Next, we explore why personal risk can change how leaders behave. Haren argues that founder ownership creates stronger alignment between company leaders and outside shareholders. Therefore, leaders with significant stakes may think differently about risk, culture, and long-term decisions. He connects this idea to skin in the game, a concept that strongly influenced his career. Moreover, he explains why obsession can matter when someone builds something difficult. Lessons From Growing Up in a Motel Then, the conversation shifts to Haren's childhood in Orange County, California. His parents owned and operated a motel, so business surrounded him from an early age. Consequently, he watched them handle customers, employees, expenses, and constant interruptions. He also helped clean rooms and saw how demanding ownership could become. However, those experiences taught him about work, family, responsibility, and entrepreneurship. Later, he discovered the stock market in college and developed another intense interest. Haren Bhakta on Activist Investing After working in insurance, Merrill Lynch, and Morgan Stanley, Haren wanted greater control over his investment decisions. So, he began investing in smaller public companies where he could influence operations. He explains how founder ownership also relates to accountability when management controls company resources. Eventually, he joined the board of a Las Vegas ticket business and helped acquire it after bankruptcy. Along the way, he learned how difficult shareholder activism can become. What Compounding and Failure Teach Finally, we discuss patience, failure, and how people build wealth over time. Haren favors regular index investing because constant decisions can damage long-term results. Likewise, he believes founder ownership can reveal how strongly leaders share the consequences of their choices. He also explains why entrepreneurs shouldn't fear failure when they're trying to create something useful. Ultimately, founder ownership connects many parts of this conversation, including accountability, risk, purpose, and long-term thinking. More From Haren Bhakta https://www.linkedin.com/in/harenbhakta/ Chapters 00:00 Why Founder Ownership Can Create Value 01:03 How Haren Bhakta Evaluates Company Ownership 06:13 Why Founder Led Companies Can Perform Differently 09:20 How Skin in the Game Changes Leadership 15:19 How Long Term Index Investing Builds Wealth 21:11 Owner Operators Versus Hired CEOs 22:30 Growing Up in a Family Motel Business 34:31 From Insurance Sales to Wealth Management 36:53 How Shareholder Activism Creates Business Value 53:19 Advice for Entrepreneurs on Failure and Purpose

  8. Aug 13

    Boris Wexler on Entrepreneurship Career Reinvention and Building a Team

    Boris Wexler grew up in Paris with a strong academic focus and a clear path toward science. However, his interests stretched far beyond engineering. He loved movies, art, and creative work, but he didn’t initially see them as realistic careers. That tension shaped his view of entrepreneurship and personal choice. Eventually, Boris left France’s rigid preparatory school system after challenging how he was expected to learn. Soon after, he moved to the United States and completed his education at Washington University in St. Louis. Boris on Experimentation Failure and Reinvention After college, Boris entered technology consulting before returning to France and launching his first company. Although the venture raised meaningful funding, it struggled when the dot-com collapse erased much of its customer base. Meanwhile, losing his mother forced Boris to reconsider what success actually meant to him. He returned to Chicago and explored trading, furniture retail, filmmaking, and other ventures. Therefore, his path through entrepreneurship became less about following one plan and more about learning through experience. Eventually, he returned to technology and rebuilt a more stable professional foundation. The Unexpected Road Back to Entrepreneurship Later, Boris joined Move Web and helped build its professional services operation. The company changed ownership before its parent organization entered bankruptcy in 2024. As a result, Boris suddenly faced another major career decision. Instead of waiting for someone else to determine the outcome, he and three coworkers created a new company. Their customers chose to follow them, which gave the team a foundation for Space Dinosaurs. That experience reinforced Boris’s belief that entrepreneurship requires persistence, timing, relationships, and decisive action. What Wexler Learned About Leadership Today, Boris sees leadership differently than he did during his first business. Earlier in his career, he often believed his own approach should lead every decision. However, experience taught him that strong companies depend on motivated people who feel heard. Consequently, he now values collaboration, careful hiring, and shared ownership of results. His perspective on entrepreneurship also includes accepting responsibility for both mistakes and successes. Still, he doesn’t describe business ownership as an easier lifestyle. He works constantly and carries greater responsibility. Yet the ability to control his direction matters deeply to him. Ultimately, Boris believes young people should consider entrepreneurship while they have room to experiment. The larger lesson is simple. Learn quickly, surround yourself with good people, and make deliberate choices about the life you want. More from Boris Wexler https://www.linkedin.com/in/boriswexler/ Chapters 00:00 Choosing Engineering Before Discovering Other Paths 05:55 How Space Dinosaurs Got Its Name 14:35 Growing Up in Paris and Family Influences 20:28 Why Boris Questioned His Career Path 28:00 Moving From France to an American University 32:03 Starting a Technology Consulting Career 34:07 Building a Startup Before the Dot Com Crash 37:28 Grief Reinvention and Redefining Success 50:18 What Boris Would Tell His Younger Self 57:08 Leadership Lessons for Entrepreneurs and Teams

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About

Welcome to Founders Journey, a podcast that explores the lives that shape remarkable builders. Each episode features a personal conversation with an entrepreneur who shares early dreams, first jobs, key turning points, lessons from setbacks, and the steady wins that shaped their path. If you want real stories about what forms a founder and what fuels a relentless drive to build, this podcast offers it each week.

Information

  • Creator
    Jimmy Douloumbakas
  • Years Active
    2025 - 2026
  • Episodes
    47
  • Rating
    Explicit
  • Copyright
    © Jimmy Douloumbakas
  • Show Website
    Founders Journey Podcast