Founders Journey Podcast

About Founders Journey Podcast

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.

Publisher

Jimmy Douloumbakas

Category

business

Language

en

Explicit

No

First episode

21 Nov 2025

Latest episode

15 Oct 2026

Latest episodes

49 episodes in the feed.

1. 

   15 Oct 2026

   How Stuart Faught Builds and Sells Profitable Software Businesses

   Why Stuart Faught Believes Small Businesses Create Big Opportunities What if building a successful business didn't require hundreds of employees or years of complicated operations? In this episode, we sit down with Stuart Faught to explore the opportunities behind small, profitable software businesses. Stuart shares how he transitioned from selling dental software to building and selling his own companies. Along the way, he discovered that simple products could generate recurring revenue without demanding massive teams. Moreover, he explains why serving a specific market often creates more opportunities than chasing enormous valuations. The Simple Strategy Behind Building and Selling Companies After selling his first company, Stuart challenged himself to build and sell another business within 90 days. He succeeded, completing a sale for $500,000. Since then, he's repeated the process around 20 times, developing a practical approach to software businesses. Instead of pursuing complicated products, Stuart focuses on one customer, one solution, and one sales channel. Furthermore, he explains how partnerships help him reach potential customers without relying entirely on individual sales conversations. We also discuss how entrepreneurs can evaluate recurring revenue, understand business valuations, and recognize the advantages of niche markets. Ultimately, Stuart demonstrates why simplicity and consistent execution matter more than constantly pursuing new ideas. What Stuart Learned About Focus and Failure Success didn't come without setbacks. Stuart reflects on his childhood experiences in karate and competitive skateboarding, where repeated failures taught him patience and persistence. Those lessons eventually shaped his approach to entrepreneurship. However, he explains that discipline alone isn't enough without a clear direction. He shares how setting specific goals, working backward, and maintaining daily routines help him stay focused. Additionally, he discusses why mentorship could've saved him years of unnecessary trial and error. Stuart Faught on Creating Freedom Through Ownership For Stuart, entrepreneurship isn't about building the next billion-dollar company. Instead, it's about creating financial opportunities while maintaining control over his time. We explore how software businesses can support a lifestyle that prioritizes family, personal interests, and meaningful work. Stuart also explains why ownership requires a different mindset than traditional employment. Finally, we discuss how aspiring founders can approach their first business without overcomplicating the process. Rather than obsessing over every possibility, Stuart encourages entrepreneurs to identify customers, solve problems, and develop consistent sales habits. If you're considering entrepreneurship or already building something, this conversation offers practical lessons on software businesses, focus, and personal freedom. You'll hear why deliberate choices, patient execution, and a willingness to keep learning can shape your entrepreneurial journey. Chapters 00:00 Why Consistent Focus Matters in Entrepreneurship 01:02 Stuart Faught on Building Small Software Companies 04:01 How Software Business Valuations Work 07:46 From Dental Software Sales to Business Ownership 09:42 How Stuart Built and Sold a Business in 90 Days 13:21 The One Product One Customer Sales Strategy 19:58 Why Small Profitable Businesses Beat Bigger Goals 24:30 How Skateboarding Developed Entrepreneurial Resilience 37:34 Why Finding Business Mentors Matters 43:36 Distribution Strategies and Leaving the 9 to 5

2. 

   9 Oct 2026

   Andre Alexander on Business Growth Without Sacrificing Your Personal Life

   What if your business gave you more time instead of demanding more of it? In this episode, we sit down with Andre Alexander to explore a different approach to entrepreneurship. We discuss why financial success doesn't always create personal freedom and how business owners can rethink their priorities. For Andre, business freedom starts with understanding what you actually want from your life. Growing up in Trinidad, Andre experienced a culture that valued ambition alongside family, sports, and community. Although hard work mattered, people still made time to enjoy themselves and maintain relationships. Later, his experiences in Canada showed him how easily constant work could become the expectation. Consequently, he developed a perspective that challenges the idea that success requires endless sacrifice. As businesses grow, founders often struggle to release control over everyday decisions. However, Andre explains how this habit creates bottlenecks, frustrates employees, and limits growth. Instead, entrepreneurs need to communicate expectations, trust capable people, and give their teams room to act. We explore why effective delegation matters and how business freedom requires changing your relationship with control. Andre's professional journey didn't follow a carefully planned route. After struggling academically, he found opportunities through family connections, encouragement, and his natural understanding of accounting. Eventually, his career led him into corporate planning, leadership, and consulting. Yet his progress included failed exams, difficult business ventures, and projects that never reached completion. Rather than defining himself through those experiences, Andre learned to recognize their lessons. His story also shows why guidance and support can change someone's direction. Many entrepreneurs chase financial milestones without defining what those milestones should accomplish. As a result, their expenses and responsibilities increase alongside their income. Andre encourages founders to identify their desired lifestyle before designing their businesses around it. Furthermore, he explains why experiences, relationships, and personal satisfaction deserve attention alongside financial goals. Business freedom becomes more achievable when your daily decisions reflect those priorities. Throughout our conversation, we discuss the importance of recognizing when something needs to change. Sometimes that means trusting employees, while other situations require leaving an unsuccessful project behind. Ultimately, Andre reminds us that entrepreneurship isn't simply about earning more or working harder. It's about learning from experience, making deliberate choices, and protecting time for what matters. If you're reconsidering your definition of success, this conversation offers a practical starting point for pursuing business freedom. More From Andre Alexander Learn more about Andre's perspective on entrepreneurship, business leadership, and creating more personal freedom. Website https://missionfreedomhq.com LinkedIn https://www.linkedin.com/in/andrealexander Additional Resources https://www.missionfreedomhq.com/founding-cohort/ Chapters 00:00 Introduction to Andre Alexander's Journey 01:09 How to Build a Business Around Your Lifestyle 03:29 Caribbean Culture and Work Life Balance 07:55 Corporate Lessons in Business Leadership 11:00 Why Entrepreneurs Become Business Bottlenecks 15:22 Growing Up in Trinidad and Learning Through Sports 20:44 How Career Setbacks Can Change Your Direction 29:34 Leadership Lessons and Entrepreneurial Mindset 37:32 Overcoming Failure and Learning From Setbacks 43:50 Advice for Young and Aspiring Entrepreneurs

3. 

   1 Oct 2026

   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

Who has been a guest on Founders Journey Podcast

Names identified in recent episode analyses. Showing up to five guests.

• David Wagstaff
• Allen Kopelman
• Alex Jekowsky
• Kevin Siskar
• Kobi Simmat

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

1 ratings

Spotify

5.0 / 5

2 ratings

Contact Founders Journey Podcast

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.