Start to Scale: The Founder's Podcast by Gildre

Hosted by Gildre.com

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Oct 2026

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Most founder podcasts are fluff. Not this one. Real founders. Real strategies. Real results. Hosted by Taiga Gamell, he interviews founders who’ve scaled companies, raised capital, and know what actually works. Every episode: 30-50 minutes with one founder who’s been from start to scale. The pivots that saved them. The mistakes that cost six figures. The growth hacks that 10x’d revenue. No theory. No BS. Just tactical advice from entrepreneurs who’ve raised millions, built teams, and created real exits. Subscribe. Take notes. Build something that matters.

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54 recent

October 20, 202634 min

54. Nelson Brooks, Cabana Boys: a $50 Favor to 10 Markets

Nelson Brooks on Building Cabana Boys Into a Charisma-Driven Hospitality Brand Taiga Gamell talks with Nelson Brooks, founder and CEO of Cabana Boys, about turning a bachelorette-party observation into a multi-market hospitality business. Nelson shares how he started during the pandemic, why charisma is central to the brand, and what it takes to scale a people-first service company without losing quality.In this episode, Nelson explains how Cabana Boys grew from a side hustle, how the company hires for personality, and why customer experience matters as much as logistics. He also discusses how Shark Tank helped establish the business’s credibility and shares advice for founders on testing ideas, staying resilient, and managing cash flow. Key topics How a bachelorette-party moment sparked the idea for Cabana Boys Starting a hospitality company during the pandemic Building the business as a side hustle before going full-time Creating event experiences that give people a compelling reason to attend Hiring for charisma and communication skills Scaling operations while maintaining quality across multiple markets Expanding into corporate events through Cocktail Crew What appearing on Shark Tank meant for the company Nelson’s vision for growing a broader hospitality brand Founder advice: start, test your idea, stay resilient, and watch cash flow Timestamps 00:00 - Welcome and introduction to Nelson Brooks and Cabana Boys 01:07 - Starting a hospitality company during COVID 02:09 - The bachelorette party that sparked the idea 07:24 - Moving from a corporate career to entrepreneurship 09:33 - Why Nelson is drawn to events and bringing people together 11:29 - What gives people a reason to attend an event 13:28 - How charisma shapes the guest experience 15:29 - Hiring for personality and building charisma into the business 19:34 - Tools for team coordination and training 24:49 - Scaling without breaking the business 26:58 - Competitors, market timing, and Cabana Boys’ positioning 28:59 - Maintaining quality across events 30:46 - Expanding into corporate events through Cocktail Crew 32:42 - Applying to Shark Tank and the impact of the show 36:00 - Nelson’s long-term vision for the business 40:42 - Advice for founders: start, iterate, and protect cash flow Notable quotes “Take charisma and make it a business model.” “People are going to remember how they felt after they interact with you.” “Cash is king.”

August 28, 202651 min

53. Why This Founder Bet $140 Million on Laundry

Join the Gildre Community: https://www.gildre.com/membership Free Newsletter: https://gildre-for-founders.beehiiv.com/ The advice that wins in SaaS can fail spectacularly in the real world of small businesses. Alex Jekowski has raised nearly a quarter billion dollars, built two companies, and turned Sense into a category-defining platform for laundromats and other overlooked verticals by betting on what most investors dismissed: hardware, software, and the operators powering the business.If you’re a founder trying to find product-market fit, raise smarter, or build in an industry people keep calling "unsexy," this conversation will change how you think about scaling. Alex breaks down why he never owned stores, why the best advisors give brutal feedback, and why the biggest opportunity often lives with the people everyone else underestimates.You'll discover: How a college startup evolved from campus classifieds into a payments business serving student life commerce The exact lessons Alex carried from his first exit into Sense, including co-founder selection, fundraising timing, and capital discipline The culture framework behind Sense’s extremely high employee retention and near-perfect customer retention Why falling in love with the problem beats chasing the founder identityWhy laundromat operators resisted "Silicon Valley tech" at first, and how trust became the real moatAlex also shares what surprised him most about raising a quarter billion dollars, why hardware looked "dumb" to investors until it suddenly looked inevitable, and how Sense is expanding beyond laundromats into dry cleaning, shared laundry rooms, RV parks, multifamily, and campuses.This is essential listening if you want the unfiltered version of building a venture-scale company in a market most people ignore, and the mindset shifts that keep founders from chasing hype instead of real value.

July 23, 202646 min

52. The Hidden Power of Challenging Yourself Every Day as an Entrepreneur

Join the Gildre Community: https://www.gildre.com/membership Free Newsletter: https://gildre-for-founders.beehiiv.com/ Unlock the secrets to transforming your entrepreneurial journey with insights from Cody Graham, COO of SoGo and a dedicated lifelong learner. Imagine building a product that genuinely changes lives—Cody shares how a simple idea and relentless curiosity can turn into a nationwide movement that connects people through food, community, and personal growth. Most founders kill their biggest opportunities by sticking to conventional paths. Cody's story of meeting his co-founders in a Scotland flat, and his pivot from corporate roles to launching SoGo, reveals how serendipity, boldness, and continuous learning can accelerate success. From his early career navigating Agile as a Scrum Master, to leveraging AI for smarter product development, Cody emphasizes the power of adaptability and pushing beyond comfort zones to solve real-world problems. In this episode, you'll discover: The crucial mindset shifts that enabled Cody to transition from corporate roles at DuPont and Fusion 92 to leading a revolutionary restaurant curation app. How a random flatmate in Scotland became a lifelong partner in building a venture driven by community, authenticity, and user-centric design. Practical strategies for integrating AI into your workflow without losing sight of the human element and quality. The importance of genuine relationships, boundaries, and clear communication—especially when working with friends and co-founders. Why doing one thing well, focusing on solving everyday problems, can create lasting impact and loyal customers. Why does it matter? Because in a world flooded with options, real innovation and authenticity stand out. Cody’s story demonstrates how embracing change, challenging assumptions, and relentlessly pursuing value-driven products can open doors to markets and opportunities you never imagined. Whether you're a budding entrepreneur, product creator, or someone seeking lifelong growth, this episode offers actionable insights to fuel your journey and inspire you to build something meaningful. Perfect for entrepreneurs, product builders, and anyone eager to turn ideas into impactful realities—tune in to learn how a mindset of curiosity, resilience, and purpose can reshape your path and create lasting success. Cody Graham is COO of SoGo, a community-focused restaurant app, and a Gildre member with a background in product development and AI integration. His journey from corporate roles to startup success is driven by a passion for building accessible, personalized solutions that improve lives.

May 7, 202654 min

51. How Asking Questions With the ASLA Principle Can Double Your Income

Join the Gildre Community: https://www.gildre.com/membership Free Newsletter: https://gildre-for-founders.beehiiv.com/ Unlock the secret to exponential growth through the power of genuine connection and servant leadership—lessons from a seasoned entrepreneur who built multiple successful ventures from scratch. When most people focus solely on transactions, they miss the transformative impact of relationships. Steve Ramona reveals how authentic networking at places like gyms, restaurants, and community events can turn casual encounters into lifelong opportunities—just like it did for his fitness and restaurant businesses, and even his recycling company. Dive into concrete frameworks like the ASLA principle—Ask, Listen, Learn, Act—that have fueled not only his business success but also his ability to connect deeply with others. You’ll discover: - How building a network in a health club led to launching a record-breaking restaurant and recycling business in Silicon Valley. - The surprising role gyms and community spaces play in cultivating powerful relationships and business opportunities. - The mindset shifts—such as practicing humility and asking questions—that turn everyday interactions into valuable connections. - Why asking questions and listening actively can double your income and elevate your leadership skills. - The importance of lifelong learning, humility, and serving others without expectation—principles that can transform your personal and professional life. Whether you’re a founder, sales professional, or aspiring entrepreneur, this episode is a masterclass in doing business with a servant’s heart. Missing out on these insights could mean passing up on the relationships and opportunities that could redefine your career and life. Perfect for anyone committed to growth, connection, and making a meaningful impact—because in business, the real asset is people. Will you step into the power of service and authentic connection? Steve Ramona is an accomplished podcaster, TV host, and business mentor known for his authentic approach to networking and leadership. His eclectic background—from fitness to food, electronics recycling, and media—demonstrates how genuine relationships and continuous learning can propel you to new heights. Get ready to change your perspective on networking, sales, and leadership—this isn’t just theory, it’s proven real-world success. Hit play and start transforming your relationships into your greatest business assets.

March 25, 202646 min

50. How Traveling and Odd Jobs Shaped Entrepreneurial Success

Join the Gildre Community: https://www.gildre.com/membershipFree Newsletter: https://gildre-for-founders.beehiiv.com/Most entrepreneurs kill their biggest growth potential by sticking to rigid plans. Iliana Alvarado reveals how embracing unpredictability, building from experience, and leveraging structure can turn fearless travelers into thriving business owners.In this episode, Iliana shares her extraordinary journey from legal studies in Mexico to working across Chile, Germany, and the U.S., carving a path that defies traditional expectations. She discusses the importance of adaptability in Latin America's diverse work cultures, the power of odd jobs for relationship-building, and why risk-seeking drives her entrepreneurial success.You'll discover how her multicultural background and spontaneous decision-making style cultivated resilience, cultural agility, and a unique approach to business growth. Eliana also dives into her tech venture, N6 Systems, explaining how she recognized a critical gap in IT governance and harnessed the booming AI era to expand services—timing that many overlooked.We break down:- How her international experiences shaped her work ethic and vision- Strategies for thriving in complex Latin American markets with structures that demand adaptability- Why sleep, health, and passion trump long hours in high-stakes entrepreneurship- The role of culture in work style differences across Latin America, Europe, and Asia- Practical insights on positioning tech and AI in business transformation This episode is essential listening if you're contemplating a global career, transitioning to entrepreneurship, or seeking a fresh perspective on integrating culture, risk, and structure into your growth story. Eliana’s honesty, humor, and strategic mindset challenge conventional wisdom—showing that success often comes from embracing the unpredictable.Join us for actionable advice, inspiring stories, and a reminder that your unique background is your greatest asset in building a business that thrives in a connected world.

February 18, 202643 min

49. Unlock the Secret to Online Success: Why Sharing Your Failures is the Ultimate Trust Builder

Unlock the secrets to thriving in a world where work is being revolutionized by AI. Sharon Gai—former Alibaba executive turned international keynote speaker—shares how the future will reward those who embrace human creativity over mechanical tasks. If you're a founder, operator, or growth-driven professional feeling overwhelmed by rapid technological change, this episode reveals how to turn hazards into opportunities—and become indispensable in an automated future. Key topics:- Sharon’s career path from corporate roles to keynote speaking- The importance of personal branding and digital footprint- How COVID accelerated opportunities in online speaking and community building- Strategies for finding and leveraging live events and communities (Luma, Instagram)- Balancing in-person and online presence for personal branding- Engaging audiences online vs. in person and creative presentation tips- The role of authenticity and documenting failures in personal and company branding- Insights into AI’s influence on work, creativity, and innovation- Future of work: meritocracy, automation, and human judgment- Sharon’s upcoming book "How to Do More with Less" – transforming busy bees into strategic beekeepersTimestamps: 00:00 - Introducing Sharon Gai: Corporate leader turned keynote speaker02:29 - Why Sharon transitioned from stable corporate roles to speaking03:34 - The rise of the B2B creator and personal branding opportunities04:32 - How COVID opened new doors for online communities and speeches06:17 - Building trust and credibility in the speaking industry08:13 - The resurgence of live events and in-person networking post-COVID10:08 - The craving for analog experiences amidst digital saturation11:28 - How people discover keynote events: platforms and community building12:41 - Traditional B2B event spaces vs. niche communities on Instagram15:18 - Balancing offline appearance with online brand development16:13 - Leveraging strengths in online video vs. in-person speaking skills18:13 - Engaging large online groups and making virtual speaking more authentic20:24 - Using memes, humor, and relatability to connect with audiences22:07 - How founders can build personal brands by documenting failures24:47 - Insights from Sharon’s time at Alibaba and AI innovations in e-commerce26:44 - The impact of AI on China’s Double Eleven shopping festival28:39 - Moving from rote tasks to strategic, creative work in the age of AI31:23 - The future of work: uneven AI adoption and the importance of human judgment33:21 - The importance of democratizing AI knowledge and education35:14 - Meritocracy and the changing landscape of labor and performance-based roles38:29 - Sharon’s upcoming book "How to Do More with Less" and key takeaways40:02 - Words of wisdom for growth-stage founders in a rapidly evolving landscapeResources & Links:How to Do More with Less: Future Proofing Yourself in the Age of AI (search on Amazon)Luma – Platform for online communities and eventsBadassery Community – Online community linking speakers and creatorsSharon Gai - LinkedIn | Twitter

January 16, 202638 min

48. From Apartment Kitchen to 9-Figure Pet Food Brand: The Spot & Tango Story w/ founder Russell Breuer

Join host Taiga Gamell on the Start to Scale Founders Podcast as he sits down with Russell Breuer, founder of Spot and Tango. Discover how Russell transitioned from a traditional career in management consulting to launching a nine-figure pet food business out of his NYC apartment. Learn about the innovative approaches that set Spot and Tango apart in the pet food industry, including their direct-to-consumer model and personalized pet nutrition solutions. Russell shares insights on entrepreneurship, the importance of grit, and the journey of building a vertically integrated company. Tune in for an inspiring conversation about passion, persistence, and the future of pet wellness. Keywords:Pet Food, Entrepreneurship, Direct-to-Consumer, Innovation, Business GrowthTakeaways:- Russell's transition from consulting to entrepreneurship was driven by a passion for innovation.- Spot and Tango's success is rooted in its direct-to-consumer model and personalized pet nutrition.- The importance of grit and persistence in overcoming entrepreneurial challenges.- How customer feedback shaped the development of Spot and Tango's products.- The role of vertical integration in scaling the business.- Russell's international experience contributed to his management style and company culture.- The impact of the COVID-19 pandemic on pet ownership and business growth.- Spot and Tango's commitment to using human-grade ingredients in pet food.- The significance of building a strong team to support business expansion.- Russell's advice for aspiring entrepreneurs: embrace challenges and persist through difficulties.Sound Bites:"Grit can get you through anything.""We make unbelievable products for pets.""Our mission is using human-grade whole ingredients.""The pet food world has seen very little innovation.""We are a pet health and wellness brand."Chapters:0:00 Introduction and Russell's Background5:30 The Birth of Spot and Tango15:00 Overcoming Challenges and Scaling the Business25:00 The Role of Innovation and Customer Feedback35:00 Building a Team and Company Culture45:00 Advice for Aspiring Entrepreneurs#PetFood #Entrepreneurship #SpotAndTango #BusinessGrowth #Innovation

December 18, 202543 min

47. From Bahamas to Yale: Gadareth Higgs' Journey

In this episode of Start to Scale, host Taiga Gamell sits down with Gadareth Higgs, a seasoned investor with a rich background in biomedical sciences and a Yale education. Gadareth shares his journey from the Bahamas to becoming a senior investment analyst at Grander, where he focuses on life sciences and healthcare investments. Tune in to discover insights on continuous improvement, the role of AI in life sciences, and Gadareth's advice for founders navigating the investment landscape. Whether you're a startup founder or interested in the future of biotech, this episode offers valuable perspectives and actionable advice.Takeaways:- Gadareth Higgs transitioned from a scientific background to investment analysis.- Continuous improvement is essential for personal and professional growth.- AI is transforming the consulting and investment landscape.- Building relationships with investors is crucial for founders.- Efficiency and organization are key to success in any field.- The Pomodoro technique can enhance productivity and focus.- Investors are looking for innovative solutions in life sciences.- Cultural perspectives influence approaches to work and efficiency.- Lifelong learning is vital for staying relevant in a changing world.- The future of life sciences will be heavily influenced by AI advancements.Sound Bites"You cannot control what you do not record.""AI is going to play a massive role.""Think of it as building relationships."#investmentinsights #lifesciences #healthcareinnovation #continuousimprovement

November 7, 202546 min

46. From Track to Tech: Robie Webster Jr.'s Entrepreneurial Leap

Join us as we dive into the inspiring journey of Robie Webster Jr., a former Division I athlete turned entrepreneur. In this episode, Robie shares his insights on the power of grit, the importance of lifelong learning, and his transition from consulting to founding Mtrc, a groundbreaking fitness technology company. Discover how Robie's experiences have shaped his approach to business and why he believes in the strength of having a co-founder. Whether you're an aspiring entrepreneur or simply looking for motivation, this episode is packed with valuable lessons and advice. Don't miss it! Keywords: Robie Webster Jr., Metric, entrepreneurship, grit, lifelong learning, consulting, fitness technology, co-founder, business challenges, Division I athlete Takeaways: Grit is essential for success in both athletics and business. Lifelong learning involves asking the right questions. Transitioning from consulting to entrepreneurship requires leveraging insights. Having a co-founder is crucial for startup success. Metric aims to make fitness accessible and personalized. Robie emphasizes the importance of internships for athletes. Balancing athletics and academics taught Robie valuable life skills. Robie values wisdom and seeks it daily through prayer. Metric's vision includes integrating personalized fitness data. Robie advises against starting a business alone. Learn more at Gildre.com

October 9, 202548 min

45. From StubHub to AI: Chris Tsakalakis on Innovation

In this episode of the Start to Scale: The Founders Podcast by Gildre, Taiga Gamell interviews Chris Tsakalakis, former CEO of StubHub and current venture partner at Starhawk Ventures. They discuss Chris's journey from working at Bain to leading StubHub, the evolution of the internet and AI, and insights into building successful B2C businesses. Chris Tsakalakis, StubHub, AI, B2C, entrepreneurship, internet evolution, business growth, venture capital, leadership, innovation KeywordsTakeaways Chris Tsakalakis shares his journey from Bain to StubHub. The importance of aggressive marketing and customer satisfaction in business growth. Chris's insights on the evolution of the internet and AI. The role of networking in career advancement. Chris's advice for aspiring entrepreneurs and tech CEOs. The significance of electronic ticket delivery in StubHub's success. Chris's perspective on the future of work with AI. The value of bootstrapping in entrepreneurship. Chris's thoughts on the next wave of growth in tech. The importance of being proactive and valuable in one's career. "Aggressive marketing was key to our growth." "Electronic delivery transformed our customer experience." "AI is the next wave of tech growth." "Be proactive and valuable in your career." "Bootstrapping is crucial for strategic growth." "Networking is easier today than ever before." "The internet's evolution has been fascinating." "Customer revenue is the best validation." "AI can democratize content creation." "Leadership requires strategic thinking and expertise." Chapters 00:00:00 Introduction to Chris Tsakalakis 00:03:00 Journey from Bain to StubHub 00:09:00 The Evolution of the Internet and AI 00:15:00 Building Successful B2C Businesses 00:21:00 Advice for Entrepreneurs and Leaders 00:27:00 The Future of Work with AI

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