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. 4d ago

    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

  2. Jul 9

    Alex Jekowsky on Building Sense 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 Sense 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

  3. 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

  4. 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

  5. Jun 18

    John Hsu on Opioid Recovery Startups and Purpose Driven Leadership

    We sit down with John Hsu to trace the pressure, discipline, and responsibility that shaped his early life. He grew up in California in a Taiwanese immigrant family that pushed hard for grades, stability, and work. At the same time, sports helped him find belonging and build confidence. That mix of pressure and teamwork stayed with him. It also shaped how he thinks about success, duty, and risk. He reflects on what it meant to grow up between cultures. He learned to save early, work early, and think about survival before comfort. However, he also learned that ambition needs more than good grades. It needs people skills, courage, and the freedom to dream bigger. From Anesthesia to Addiction Care John walks through his path from college sports to medical school and then into anesthesia, chronic pain, and addiction medicine. He explains how he evaluated patients before surgery and why recovery often extends far beyond the operating room. He also shares a striking point about cardiac patients, who can face depression months after surgery. Later, he shifts from anesthesia toward chronic pain and opioid use disorder care. That change became personal after his own heart attack. As a result, he stopped seeing addiction as a side issue. He began treating it as urgent medicine. He argues that opioid use disorder needs medical treatment, long term support, and far less stigma. Why John Hsu Chose Hard Problems This part of the conversation turns toward the businesses he built around overdose prevention, safer prescribing, and remote monitoring. He explains why addiction affects both the mind and the body. So, he believes treatment must address both. He breaks down opioid use disorder in plain terms and explains why fast fixes often fail. He also talks through a connected pill dispensing system that helps doctors monitor whether patients follow a prescription. That idea comes from a simple problem. Doctors often lose visibility once a patient leaves the pharmacy. Therefore, John focuses on tools that improve accountability, support care, and reduce risk. He believes better systems can improve opioid use disorder treatment and help prevent relapse. What John Hsu Wants Founders to See By the end, this episode becomes a wider talk about work, purpose, faith, and leadership. John shares how stress shaped his habits, why he kept building after success, and what he learned from nearly dying. He doesn’t frame business as status. Instead, he frames it as service. That perspective gives this conversation its weight. He believes opioid use disorder carries stigma that blocks treatment and costs lives. He also believes founders should solve real problems, move with urgency, and stay honest about what people need. So, this episode offers more than a life story. It gives a clear look at responsibility, resilience, and mission. More from John Hsu https://www.linkedin.com/in/john-hsu-md-300a8b2a/ Chapters 00:00 Heart surgery recovery and depression 00:42 Founders Journey introduction 01:38 Growing up Taiwanese in California 06:11 Family pressure work and education 11:23 Dreaming big in America 22:21 College sports and the road to medicine 30:14 Residency stress and real estate projects 32:34 Anesthesia chronic pain and addiction care 47:28 Startups tackling overdose and adherence 57:40 Founder mindset purpose and leadership

  6. Jun 12

    Maddy Niebauer on Peace Corps Lessons and Building The Chiefs

    We sit down with Maddy Niebauer to trace the experiences that shaped her early mindset. She reflects on growing up in the Bay Area, moving often, and changing schools year after year. As a result, she learned to adapt fast, make friends quickly, and keep going through disruption. She also explains how high academic expectations at home pushed her to take school seriously, even when the pressure felt heavy. Maddy Niebauer and the search for direction From there, the conversation moves into college and the uncertainty that comes with choosing a path too early. She shares why she started college undecided, why psychology pulled her in, and how research first seemed exciting. However, one long project with inconclusive data changed her view of academic work. That moment forced her to question what kind of future she wanted. It also opened the door to a wider conversation about discovery, curiosity, and the limits of rigid career planning. In that sense, fractional leadership starts with learning how to step back and reassess your role. West Africa changed the frame After college, Maddy joined the Peace Corps and spent more than two years in Ivory Coast. That chapter gave her a direct view of service, shared responsibility, and daily life in a communal culture. She describes how family structures, work, and even simple tools carried a different meaning there. Because of that, she returned with a stronger sense of perspective and a deeper interest in mission driven work. Later, that same perspective shaped how she viewed management, nonprofit impact, and fractional leadership in practice. Building The Chiefs with Maddy When she returned to the United States, she worked in education, earned an MBA at Columbia, and later moved into nonprofit consulting. Eventually, a chief of staff role at Teach For America became the turning point. She didn’t chase that title at first, yet the work fit her strengths. Then layoffs pushed her to make a decision. Instead of starting over in another job, she turned a side engagement into a business. That move became The Chiefs, a company built around part time executive support. Here, fractional leadership became more than an idea. It became the service itself. What Maddy learned about letting go We also talk through the messy parts of building a company. She explains early pricing mistakes, unclear project scope, and the cost of being too accommodating. More importantly, she shares what changed when she stopped trying to do everything herself. Her decision to hire support, build systems, and later work with a co CEO gave the business room to grow. At the same time, it gave her more freedom. That lesson sits at the center of this episode. Fractional leadership helps leaders focus on what only they can do. In the end, fractional leadership works best when trust, structure, and self awareness all grow together. Chapters 00:00 Welcome to Founders Journey 01:07 Meet Maddy Niebauer 01:31 Growing up in the Bay Area 05:12 What changing schools taught her 09:11 College pressure and choosing a path 20:21 Peace Corps work in Ivory Coast 26:21 Tutoring centers and social enterprise 28:24 Columbia MBA and nonprofit consulting 36:19 Teach For America and chief of staff work 40:30 Starting The Chiefs and letting go as a founder

  7. Jun 4

    Randy Johnston on Building Technology Leadership That Actually Helps People

    We talk with Randy Johnston about the kind of childhood that builds real problem solvers. He grew up in Hutchinson, Kansas, and learned by asking questions. He learned from mechanics, carpenters, electricians, and architects in his own neighborhood. As a result, he built a practical mindset early. That mindset shaped his approach to technology leadership long before he entered business. A curious start with Randy Johnston Randy also explains why listening matters more than status. He says you can learn from almost anyone, if you ask and stay quiet. That lesson runs through the whole conversation. It also explains why his work in technology leadership stayed focused on people, not prestige. Randy Johnston on choosing service over scale Later, we get into the choices that shaped his career. He turned down a job with IBM because he wanted to stay rooted in Kansas. That decision looked limiting at first. However, it opened a different path. He moved from programming to teaching, then into product design, consulting, and entrepreneurship. Along the way, technology leadership kept showing up through service, teaching, and thoughtful execution. He shares how he helped build products many people still use. That includes work tied to Microsoft Office, Excel pivot tables, ThinkPad TrackPoint, and more. Yet he doesn’t frame that work as fame. Instead, he frames it as useful work. That gives this episode a grounded view of technology leadership that many founders rarely hear. Lessons from Randy Johnston that still hold up The strongest part of this conversation may be Randy’s business philosophy. He doesn’t believe bigger always means better. In fact, he chose to shrink parts of his company when growth weakened relationships. He wanted to know people by name. He wanted to stay close to the work. Because of that, technology leadership becomes less about scale and more about responsibility. We also talk about money, ethics, and judgment. Randy argues that helping people creates stronger businesses than chasing revenue alone. He warns against secrecy, ego, and empty passion. Instead, he pushes founders to improve ideas, build sound processes, and keep an outward focus. That makes his view of technology leadership especially useful for entrepreneurs building for the long term. What founders can take from this episode By the end, this episode becomes a guide to better decision making. Randy talks about family, travel, balance, trust, and choosing work that aligns with your principles. He explains why he left companies that crossed legal lines. He also explains why ideas matter less than execution and improvement. So while the stories are remarkable, the real value sits in the lessons. If you care about building useful products, staying ethical, and leading with substance, this conversation delivers. It shows how curiosity compounds over time. It shows why relationships still matter. And it shows how a long career in technology can stay deeply human. Chapters 00:00 Growing up curious in Hutchinson Kansas 08:15 Why asking questions builds better entrepreneurs 17:15 Randy Johnston and the early days of computing 30:57 Vietnam era pressure and college decisions 41:02 From programmer to teacher and textbook author 42:49 Building products behind Apple IBM and Microsoft 51:00 Why bigger business is not always better 57:05 Ethics money and how founders should think 01:04:10 Family travel and balancing entrepreneurship 01:15:43 Advice for new entrepreneurs starting today

  8. May 28

    Kobi Simmat on Wealth Creation Delegation and Business Ownership

    Kobi grew up in Sydney around national parks, beaches, boats, and building sites. So, work never sat in a separate box from life. His father ran an architecture and construction business, and the family often joined site visits on weekends and holidays. That early exposure shaped how he saw business, responsibility, and momentum. He didn’t describe entrepreneurship as glamorous. Instead, he saw it as a path to a more active and intentional life. That view frames the whole conversation around wealth creation. Why Kobi Simmat values ownership He explains that many people wait to feel inspired before they move. However, he believes people can learn to become passionate through action. He also argues that earning years are limited, so building resources for your family can’t stay optional. That idea drives his view of wealth creation. He talks openly about family roles, duty, and the need to prepare the next generation. As a result, this episode becomes less about status and more about stewardship. Kobi also shares how school never fit the way he learned. He showed up, paid attention, and still struggled in a traditional classroom. Then everything changed in technical college, where discussion replaced rote repetition. From there, he became a top student and found a learning style that worked. So, one of the clearest lessons here is simple. You still need education, but you must learn how to learn. The lesson Kobi Simmat would pass on Later, he walks through the business he built in construction consulting. His company helped contractors meet government standards in safety, quality, environment, and risk. The model created recurring revenue, long client retention, and a clear service structure. Yet the deeper lesson isn’t only about systems. It’s about leaving the technician role before it traps you. That shift matters because wealth creation gets harder when the owner stays buried in delivery. He tells a great story about finding a book in an airport called How to Grow Your Business by Taking Three Months Off. That idea pushed him to document work, delegate tasks, and step away. Then he actually left for South America for three months. Even during the global financial crisis, the business kept moving because the team had ownership. So, the episode turns delegation into a practical tool for wealth creation, not a soft leadership idea. By the end, Kobi makes a strong distinction between being a technician, a coach, and a shareholder. He believes too many founders stay attached to being the best operator. However, real progress starts when they train others, let people make small mistakes, and think like owners. That transition is central to wealth creation because it creates space, leverage, and long term value. We also hear how he brought forward years of earnings by selling his company, and why that sale fit his larger plan for family wealth, learning, and responsibility. Chapters 00:00 The book that changed how he ran business 00:00:57 Meet Kobi Simmat from Australia 00:02:31 Growing up with an entrepreneur father 00:05:21 Why work shaped every family holiday 00:10:07 His 5 AM routine and drive to keep moving 00:12:14 Why founders must build family wealth early 00:24:18 How he teaches business books to his son 00:26:05 Why school failed and discussion helped him learn 00:33:02 Choosing construction and business ownership 00:46:01 How delegation helped him take three months off

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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
    36
  • Rating
    Explicit
  • Copyright
    © Jimmy Douloumbakas
  • Show Website
    Founders Journey Podcast