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. 6d ago

    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

  2. Aug 6

    Greg Roe on Building Freestyle Trampoline Through Resilience

    Greg Roe explains how freestyle trampoline grew from his frustration with traditional sport systems. He saw young athletes seeking creativity, freedom, and personal style. Therefore, he chose to build an alternative instead of waiting for established leaders. Freestyle trampoline became his answer to rigid rules and limited expression. However, that decision brought immediate resistance. Roe faced criticism, threats, and removal from Team Canada. Still, he treated rejection as a reason to move forward. He believed the traditional model no longer matched how younger athletes wanted to participate. From Athlete to Founder Roe traces his story from a Russian orphanage to a new life in Canada. Soon after arriving, his energy led him into gymnastics. Later, he moved toward trampoline because it offered more flexibility. Sport also gave him structure, discipline, and a clear focus during school. Meanwhile, his interest in kinesiology changed how he viewed performance. He studied anatomy, psychology, and training because those subjects connected with his goals. As a result, his grades improved once learning felt relevant. He eventually left school before one final exam to pursue an emerging opportunity. That decision led him toward freestyle trampoline and a partnership with Tricia McGeer. Instead of rushing, they built trust through repeated conversations and small projects. Roe advises founders to watch behavior before signing agreements. In particular, pressure, urgency, and resistance to contracts can reveal serious concerns. What Greg Learned About Failure Roe doesn’t view setbacks as permanent failures. Instead, he treats them as problems that still need better solutions. His early events built relationships, although they didn’t produce enough profit. Therefore, the team changed its approach and created franchise partnerships. That change reduced travel costs and expanded the organization into more countries. However, growth created new problems involving contracts, communication, and local infrastructure. Roe kept adjusting the model instead of abandoning it. He argues that every solution creates another puzzle. The same approach now guides his work with esports. At first, physical athletes didn’t understand the value of digital competition. Consequently, Roe changed the message and focused on lower costs, more access, and added prizes. Freestyle trampoline could then connect physical events with digital participation. Roe on Trust and Partnerships Roe also explains how his approach to meetings changed. Earlier, he focused on selling his vision. Now, he starts by asking what the other person needs. Therefore, he spends more time listening and less time pitching. This shift also changed how he views sponsorships. He now treats sponsor funding like an investment that must create measurable value. Moreover, he encourages athletes to prove their value before requesting support. Views alone don’t guarantee sales, trust, or useful results. Greg Roe and a New Direction Ultimately, Roe believes founders must commit to work they genuinely care about. Success may take ten years or longer. Freestyle trampoline required patience, constant learning, and repeated adjustments. His story shows why curiosity, persistence, and service matter more than quick recognition. Freestyle trampoline also reflects a wider lesson about entrepreneurship. Build for real needs, study people carefully, and keep refining the solution. More From Greg Roe https://www.gregroetrampoline.com/ Chapters 00:00 Why Urgent Business Pitches Raise Red Flags 01:16 What Is Freestyle Trampoline 04:07 Why Greg Roe Challenged Traditional Sports 06:28 Turning Team Canada Rejection Into Opportunity 11:56 From a Russian Orphanage to Canada 20:14 How Education Changed After Finding Purpose 25:03 How Entrepreneurs Can Evaluate Partners 32:05 Why Business Failure Is a Learning Process 42:19 Advice for Young Entrepreneurs 46:51 How to Build Stronger Business Partnerships

  3. Jul 30

    Derik Krauss on Failure Focus and Sustainable Entrepreneurship

    Derik Krauss explains how early experiences shaped his interest in business ownership. His father’s career changes showed him persistence during uncertainty. Later, a business framework helped him separate personal effort from scalable value. That idea sparked his commitment to entrepreneurship. However, his path still required patience, experimentation, and entrepreneurial resilience. How Krauss Found a Profitable Niche After college, Derik joined a startup accelerator and helped launch a software company. Although the venture gained customers, it ultimately failed. Instead of seeking traditional jobs, he and his partner offered web design and digital marketing services. Then, one successful credit union project revealed a stronger direction. Their focus created momentum and strengthened their entrepreneurial resilience. Derik’s Perspective on Failure Derik doesn’t present failure as easy or enjoyable. Instead, he sees opposition as a necessary part of growth. Challenges force people to reconsider their choices, improve their approach, and keep moving. Therefore, entrepreneurial resilience comes from responding thoughtfully after setbacks. It doesn’t come from avoiding every difficult result. Building Around Strengths and Focus The conversation also explores effort, self-awareness, and personal energy. Derik believes founders should identify work that energizes them. Meanwhile, they should delegate tasks that drain them or limit their impact. He also explains why choosing a niche creates clarity. Consequently, entrepreneurial resilience depends on focused decisions, not constant activity. Practical Lessons for Sustainable Growth Derik closes with several lessons from more than a decade in business. First, founders can’t scale while doing everything themselves. They must trust capable people with meaningful responsibilities. He also discusses envelope budgeting and the Profit First method. That approach helped his company protect profit before assigning operating expenses. Derik Krauss on Choosing Entrepreneurship Finally, Derik describes how artificial intelligence could change service businesses. His company now explores model context protocol tools for financial institutions. These systems could let AI agents complete tasks across connected platforms. Still, the larger lesson remains human. Sustainable progress requires purpose, flexibility, and entrepreneurial resilience. More From Derik Krauss https://www.linkedin.com/in/derikkrauss/ https://metrifi.com/ Chapters 00:00 Why Opposition Creates Personal Growth 01:14 Meet Entrepreneur Derik Krauss 01:34 How AI Agents Could Transform Business 05:16 Why Derik Chose Entrepreneurship 09:43 How a Failed Startup Led to Web Design 11:19 Finding a Profitable Credit Union Niche 21:17 Why Effort Creates a Competitive Advantage 42:08 How Entrepreneurs Can Recover From Failure 49:09 Building a Business Around Your Strengths 53:18 Niche Focus Delegation and Profit First

  4. Jul 24

    Domingo Guerra on Building Startups and Securing the AI Powered Future Now

    We explore how an entrepreneurial mindset began with ownership, preparation, and a clear view of future choices. In high school, he worked backward from ambitious goals and identified the building blocks he needed. Therefore, math, physics, and engineering became practical steps rather than abstract subjects. He didn’t know the final destination, but he understood how early decisions could stack. That approach shaped every major move that followed. He left Monterrey at eighteen and moved to Austin without friends or family nearby. However, the culture shock forced him to manage his schedule, studies, work, and daily life. That experience strengthened his entrepreneurial mindset because responsibility became a daily practice. Later, Stanford, Silicon Valley, and demanding engineering roles expanded his technical judgment. Meanwhile, business school helped him understand why strong products still fail in the market. He eventually stopped preparing and started building. First, he recognized a growing mobile security problem inside his own workplace. Then, he left a stable career and launched a startup with a trusted cofounder. The first product arrived too early, so the team kept testing ideas. Because they stayed close to customer needs, they found a valuable mobile security solution. Their entrepreneurial mindset helped them adapt without abandoning the underlying problem. The company raised venture funding, grew, and sold to Symantec in 2018. Still, the acquisition taught him that financial success doesn’t always create meaningful work. He missed the speed, ownership, and direct impact of startup life. Consequently, he began advising founders and investing in cybersecurity companies. Those experiences revealed where his entrepreneurial mindset created the greatest value. He now focuses on security for AI because he sees another major workplace transformation. AI can improve productivity, automate tasks, and create new digital workers. However, it can also expose confidential data and create privacy, security, and compliance risks. He explains why companies need safeguards before employees share sensitive information with public tools. Therefore, security must advance alongside adoption rather than follow it years later. The conversation also examines risk, luck, and the cost of waiting too long. He argues that preparation matters only when someone acts on opportunity. Likewise, he believes founders must love the problem more than the possible payout. That entrepreneurial mindset helps people endure uncertainty, setbacks, and slow progress. Ultimately, small wins can stack into meaningful results when curiosity and commitment remain strong. He also shares one regret. He would’ve started his first company earlier. 00:00 Building the Foundations for Future Success01:08 Domingo Guerra and His Cybersecurity Career04:19 Why Startup Impact Matters More Than Money08:11 How Technology Transformations Create Opportunity10:56 AI Agents and the Future of Workplace Automation13:10 How Businesses Can Protect Sensitive AI Data16:17 Growing Up With Entrepreneurial Role Models21:17 How to Evaluate Risk and Create Your Own Luck33:30 Engineering Lessons From Silicon Valley55:51 Advice for New Entrepreneurs Facing Uncertainty How Guerra Turned Curiosity Into ConvictionWhat Domingo Learned About Risk and AIChapters

  5. Jul 16

    Brian McLean on Building a Jewelry Business Through Change and Trust

    Brian McLean didn’t enter the jewelry industry through a detailed career plan. Instead, an early job introduced him to sales and customer relationships. He soon discovered that he could understand what people wanted and connect them with meaningful pieces. However, his personal life remained unsettled during those early years. Eventually, he changed direction and committed himself to a healthier path. That decision created the foundation for decades of business resilience. Turning a Small Store Into a Lasting Business Brian purchased a 235-square-foot jewelry store in 1990 with limited resources. His father-in-law lent him money, while Brian used savings from an earlier accident settlement. He and his wife protected every dollar and reinvested their first profits. Therefore, the store grew through patience rather than sudden expansion. Brian handled sales, paperwork, buying, and daily operations himself. Although this approach gave him control, it also made the business dependent on his presence. Over time, Brian realized that customers needed to trust the whole team. His sister, daughter, and employees gradually assumed larger responsibilities. Consequently, he began moving from working inside the store toward leading it. This shift required business resilience, because delegation challenged his perfectionism and fear of losing control. Brian McLean on Technology and Custom Jewelry Custom jewelry became one of Brian’s most rewarding areas of work. He enjoys helping customers transform personal ideas into finished pieces. Moreover, modern computer-aided design allows his team to test details before production begins. Customers can review shapes, stones, and proportions before approving a final design. Brian learned the software, yet he recognized that another specialist could use it more effectively. As a result, he focused on directing the process instead of performing every task. That choice reflects business resilience through practical leadership. It also shows why owners must understand their tools without controlling every technical step. Moving Beyond Fear and Constant Chaos Fear drove Brian during the early years because failure didn’t feel like an option. He had a family to support and no clear alternative career. However, fear eventually gave way to faith, consistency, and greater internal peace. He learned that daily sales don’t define the health of a long-term business. Instead, honest service and steady execution create trust across changing conditions. When a major supplier limited his access after the store moved, Brian looked for another path. He joined an independent jewelers organization and gained new systems, suppliers, and operational knowledge. Therefore, the setback produced stronger business resilience and a more capable store. What Brian’s Journey Teaches Founders Brian’s story shows that progress often begins with simply showing up. Yet consistency doesn’t mean repeating every old habit. Founders must release control, develop their teams, and adjust their systems. They must also protect the human connection behind every sale. For Brian, jewelry often carries memories of parents, grandparents, and other loved ones. His team helps customers reshape those pieces into wearable family heirlooms. Ultimately, that responsibility keeps service personal and meaningful. His experience proves that business resilience grows through honesty, adaptability, faith, and care for others. Chapters 00:00 Why Founders Must Stop Doing Everything 01:07 Brian McLean’s Jewelry Business Journey 03:21 How an Accidental Career Became a Calling 06:14 Why Custom Jewelry Creates Emotional Value 07:13 How CAD Changed Custom Jewelry Design 10:01 Becoming a Business Owner Instead of a Technician 11:24 How Founders Can Delegate Without Losing Control 23:14 Recovery Faith and Rebuilding a Life 33:51 Why Consistency Matters More Than Daily Sales 44:31 Building Systems That Replace Business Chaos

  6. Jul 9

    Alex Jekowsky on Building Cents and Leading Through Startup Pain

    Starting where the friction lives Alex Jekowsky joins us to talk about the kind of founder mindset that starts with real friction. He didn’t chase startup status. Instead, he paid attention to broken systems and asked better questions. First, that showed up on college campuses. Later, it led him into laundry, where he saw how hard operators worked without strong software. He explains why he dropped out of college, built a campus marketplace, and sold that first business at 23. Then, while exploring laundromat ownership, he noticed something bigger. The opportunity wasn’t only in buying stores. It was in helping owners run them better. That shift says a lot about founder mindset, because it puts the problem ahead of the ego. What Alex Jekowsky learned from music and sports He also shares how his family shaped the way he leads. His parents were musicians, and his father’s discipline left a deep mark. Practice, repetition, and standards mattered. So did staying steady under pressure. Those lessons later carried into company building, team leadership, and the hard parts of fundraising. Sports added another layer. Coaches taught him how adversity builds judgment, not just toughness. Because of that, he doesn’t treat pain as a detour. He treats it as part of the work. That view runs through his founder mindset and shows up in the way he talks about culture, failure, and long-term execution. Jekowsky on failure and durable teams A big part of this conversation focuses on failure. Alex doesn’t frame failure as damage. Instead, he treats it like feedback that should lead to action. He talks about reflecting on losses, owning mistakes, and learning fast enough to improve the next decision. That approach gives teams more honesty and more resilience. He also explains why founders need partners, advisors, and people who will challenge them. You’ll hear how he thinks about co-founders, operator empathy, and building a company that people want to stay with. That matters, because founder mindset isn’t only about ambition. It’s about judgment, trust, and the ability to keep going when conditions turn against you. Building with Alex instead of performing startup life Near the end, we get practical. Alex lays out what young founders should actually do first. Talk about the idea. Test whether the energy is contagious. Find people who complement your strengths. Build a network before things get hard, not after. Most of all, commit to the work required to win. He also shares a grounded view of the laundromat business. It can be attractive, yet it isn’t passive. Technology matters early, and discipline matters even more. That advice lands because it comes from experience, not theory. If you care about execution, leadership, and founder mindset, this episode will stay with you. It’s also a strong reminder that founder mindset grows through action, not image. More From Alex Jekowsky https://www.linkedin.com/in/ajekowsky/ https://alexjekowsky.com/ Chapters 00:00 Cold open on talent and hard work 01:12 Meet Alex Jekowsky and Cents 05:29 Dropping out to build a startup 09:00 Fall in love with the problem 13:59 Why he chose laundry tech 17:24 Raising capital through market swings 21:29 Family influence music and discipline 39:31 School happiness and self awareness 42:29 Why failure should be studied 53:02 Advice for young founders

  7. Jul 2

    Sugira Rubasha on Identity Football and Building a Creative Career

    Sugira Rubasha traces his story from Nairobi to Sydney, and he explains how that move shaped his early world. He grew up around many cultures, yet he kept searching for a clearer sense of self. Because of that, identity and legacy becomes one of the strongest threads in this episode. He talks about names, family roots, and why pride in where you come from can shape how you move through life. Growing Through Football and Failure He also shares how football gave him structure, belief, and a reason to dream big. From private school in Sydney to trials in the United States, he kept chasing the highest level. However, the path didn’t move in a straight line. He missed chances, earned new ones, and learned how to recover after setbacks. That’s where identity and legacy starts to connect with discipline. He didn’t just want a contract. He wanted a life that reflected who he was and what he could become. Sugira walks through trials with Philadelphia Union, San Jose Earthquakes, and Portland Timbers. He also reflects on his call up to Rwanda’s under 23 national team. Those moments gave him proof that persistence matters, even when progress feels uneven. Still, he doesn’t romanticize the process. He speaks clearly about pressure, competition, injury, and the cost of chasing a dream across countries. Why Sugira Rubasha Chose a New Arena As the conversation moves forward, he explains why business became the next chapter. Injuries forced tougher decisions, but they also revealed another strength. He found the same creative energy in content, editing, and media work that he once found on the pitch. So instead of treating entrepreneurship like a backup plan, he treated it like a new field to master. Here again, identity and legacy stays central. He wants his work to create income, freedom, and something lasting. He shares how speed, quality, and consistency helped him win early clients. He also explains why personal brand matters when trust drives business. Rather than talk in vague terms, he connects these lessons to real experiences with clients, editing work, and building a name people remember. That makes identity and legacy feel practical, not abstract. Lessons Sugira Rubasha Leaves With Us Near the end, the episode turns personal in a deeper way. Sugira talks about the meaning of his name, why names matter, and why people should understand their background instead of hiding it. That idea gives the episode its clearest takeaway. Identity and legacy isn’t just a theme here. It’s a guide for how to build, recover, and move with purpose. We also get his thoughts on consistency, self belief, and the long road of becoming successful. He doesn’t present growth as easy. Instead, he frames it as a test of patience, clarity, and repetition. Because of that, this conversation offers more than a life story. It gives viewers a grounded look at how sport, culture, creativity, and business can shape one another over time. By the end, identity and legacy feels like the lesson tying every part of his journey together. More From Sugira Rubasha https://sugirarubasha.com/ Chapters 00:00 Welcome to Sugira Rubasha's story 05:12 Growing up between Nairobi and Sydney 11:08 Identity names and cultural pride 17:41 School life sports and early ambition 24:36 Why football became the dream 31:22 Trials in America and hard setbacks 39:48 Portland Timbers and Rwanda call up 47:55 Lessons from failure pressure and patience 55:40 Injuries content work and career shift 01:03:18 Entrepreneurship consistency and legacy

  8. Jun 26

    Peter Shankman on ADHD entrepreneurship and building a life that fits

    Peter Shankman on building around a different brain We sat down with Peter Shankman to explore how he built his life around an ADHD brain, not against it. Early on, he shares what it felt like to grow up in New York City without language for neurodiversity. Because of that, school often felt hard, confusing, and limiting. Still, he found creative outlets, leaned into writing, and kept moving toward work that matched how he thinks. The ADHD advantage in work and life This episode shows how ADHD entrepreneurship can look practical, disciplined, and deeply intentional. Peter explains how he fills his calendar on purpose, because too much open time can lead him in the wrong direction. He also breaks down the systems that keep him focused, from early workouts to simple wardrobe choices. As a result, ADHD entrepreneurship becomes less about chaos and more about structure that actually works. How Peter Shankman turned connection into opportunity Peter walks us through the path from AOL to launching a PR firm, then creating HARO from a simple habit of helping reporters. Rather than waiting for perfect conditions, he kept testing ideas and learning through action. That mindset shaped his view of risk, failure, and momentum. So when he talks about ADHD entrepreneurship, he ties it to calculated risk, repeated effort, and staying humble enough to keep learning. Lessons from failure family and focus We also get into the habits that helped Peter protect his health, his attention, and his role as a father. He speaks openly about dopamine, addiction, exercise, therapy, and why social media can become a serious problem. Then he explains why he never breaks promises to his daughter, even when work pulls him across the world. That part gives ADHD entrepreneurship a human center, because success means very little without trust and presence. What Peter Shankman wants founders to remember Near the end, Peter shares direct advice for younger founders. Try things early, accept failure, and stop wasting energy on other people’s opinions. He argues that failure teaches faster than easy wins ever could. In that sense, ADHD entrepreneurship becomes a lesson in self-awareness, consistency, and building an environment that fits your brain. We think this conversation offers a clear look at what happens when someone stops forcing a traditional path and starts designing one that works. More From Peter Shankman https://www.shankman.com/ Chapters 00:00 Intro and Peter Shankman background 01:26 Growing up in New York with ADHD 03:10 First media jobs and the AOL newsroom 04:07 Starting a PR firm during the internet boom 05:50 How HARO started and why it took off 06:48 ADHD dopamine habits and daily structure 17:08 Managing focus with routines and movement 21:38 Selling HARO to PR Newswire 23:35 Faster Than Normal and neurodiversity 32:59 Parenting promises and entrepreneurial life

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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
    40
  • Rating
    Explicit
  • Copyright
    © Jimmy Douloumbakas
  • Show Website
    Founders Journey Podcast