How They Win

In this episode, Jonathan Brun, founder and CEO of Nimonik, shares how he bootstrapped his B2B SaaS company from a niche legal database into a global platform used by 900+ clients. He talks about starting with no money, why he buys small companies with bad software, and the long game mindset that kept him going for 17 years without giving up or raising funding. 🔗 Find Jonathan Brun here: LinkedIn...

In this episode, Ben Faw, co-founder and CEO of Advon Commerce and Parter at Dynamism Capital talks about building and selling Best Reviews, the future of AI-powered commerce, and what makes a founder truly investable. He also shares what he looks for in startups, how he balances running two companies, and lessons learned from both wins and mistakes. 🔗 Find Ben Faw here: LinkedIn: https://www.lin...

In this episode, Carlos Raul Garcia, co-founder and CEO of EduCup, shares how he turned a passion for math and education into a fast-growing edtech platform with over 2.5 million students. He talks about bootstrapping during the pandemic, partnering with top online educators, breaking into the B2B market for insurance and real estate training, and the biggest lessons he learned from building EduCu...

In this episode, Aaron Smith, co-founder of Savi, shares how his personal student loan experience and policy background led him to build a platform that simplifies student loan management. He talks about why they chose a B2B model, how they landed their first major client, and why trust is everything when helping people manage debt. 🔗 Find Aaron Smith here: LinkedIn: http://www.linkedin.com/in/aa...

In this episode, Zach Beegal, founder of CoPact, shares how he's changing the way B2B businesses buy and sell by guaranteeing measurable results. He explains why most companies overpromise and underdeliver, what he learned from value engineering at Deloitte, and how Copact helps businesses find partners who are actually accountable. If you're tired of the fluff in B2B sales and want a new...

In this episode, Laurel Djoukeng, founder of Sparc and KeyPath, Laurel Djoukeng, shares his journey from Wall Street to building two purpose-driven ventures. He talks about launching a tech-enabled talent platform while in grad school, the reality of bootstrapping, and how he’s now building a fintech startup to tackle home ownership through real estate tokenization. Laurel also opens up about what...

In this episode, Will Fuentes founder of Maestro Group shares how he built a sales consulting firm. He opens up about what shortens B2B sales cycles, how introverts can become top performers, and why mindset always comes first. Will also explains how he got his first clients, what he'd do differently if he started again. 🔗 Find Will Fuentes here: LinkedIn: http://www.linkedin.com/in/will-fuen...

In this episode, Mike Tyler, founder of War Room, shares the story behind his 16-year journey building a programmatic ad agency that thrives on innovation, strong client relationships, and smart use of AI. He opens up about bootstrapping, early doubts, lessons in hiring, and how his team is preparing to 3x revenue while keeping culture intact. 🔗 Find Mike Tyler here: LinkedIn: https://www.linkedi...

In this episode, Jamie Read, founder and CEO of BriteBirch Collective, shares how he went from leading award-winning agency teams to building a decentralized collective of 300+ experts. He talks about the flaws in the traditional agency model, how BriteBirch works without full-time employees, and how he's building a future-of-work community to support the next generation of solopreneurs. 🔗 Fi...

In this episode, I chat with Babar Arshad, founder of iTitans and co-founder of K-Hub, about his journey from failed startups to building two successful tech companies. We talk about bootstrapping, investing in early-stage founders and the role of patience. 🔗 Find Babar Arshad here: LinkedIn: https://www.linkedin.com/in/babar-arshad-274329115/ Instagram: https://www.instagram.com/buildwithbabarr/...

In this episode, Enrique Huesca, founder and CEO of Sendola, shares how he went from launching a microloan startup for Hispanic communities to building a global B2B payments platform. We talk fundraising, building API rails between US and LATAM banks, his biggest lessons as a serial entrepreneur, and how he picks investors and hires with character over credentials. 🔗 Find Enrique Huesca here: Lin...

In this episode, Alexander Schlager, CEO of AIceberg, breaks down what AI safety and security really mean, prompt injection attacks, and why enterprises need to take control of their LLM interactions now. 🔗 Find Alexander Schlager here: LinkedIn: https://www.linkedin.com/in/alexschlager/ Website: https://www.aiceberg.ai/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosm...

In this episode, James Pyle, founder of Awareness Elevation, talks about his journey through trauma, addiction, entrepreneurship, and how fasting became his gateway to clarity, identity, and purpose. If you’re a founder questioning your path or looking for deeper self-awareness, this episode is for you. 🔗 Find James Pyle here: LinkedIn: https://www.linkedin.com/in/jamesfpyle/ Instagram: https://w...

In this episode, Will Haire, co-founder and CEO of Bellavix, a leading Amazon and Walmart marketplace agency, shares his journey from being a licensed electrician to launching a successful e-commerce marketing agency. We talk about growing through SEO, building a business with his wife as co-founder, hiring challenges, and how niching down into marketplace marketing helped Bellavix scale. 🔗 Find...

In this episode, I’m joined by Keala Kanae, founder of Inspirean. Keala went from living in his mom’s spare room with a 500 credit score to building a $140M revenue company and eventually exiting it. We dive into the psychology of success, why so many high performers self-sabotage even when they’re doing “everything right,” and how to rewire your brain to move past fear, procrastination, and limit...

In this episode, Michael Counts, founder of A-plan Coaching and Mpath AI talk about what really helps people change. We explore why most people don’t need therapy, they need a coach. Michael shares the key difference between therapy and coaching, why people stay stuck (even after watching self-help content), and how AI can make world-class coaching affordable and accessible. 🔗 Find Michael Counts...

In this conversation, Michael Ward, CEO and founder of Paminga, share how he bootstrapped a full-scale enterprise marketing automation platform to compete with giants like Marketo and HubSpot. He walks us through his 20-year entrepreneurial journey, how customer needs drove the product evolution, and why Paminga stands out for its usability, scalability, and modern features. We also discuss how co...

In this conversation, Chris Hunter (aka Dumb Money Hunter) shares how he went from being a solo trader and YouTuber to building a large-scale trading platform that pays traders for performance. They discuss the mechanics of modern prop firms, trader psychology, and why ego is your biggest enemy in trading 🔗 Find Chris Hunter here: YouTube: https://www.youtube.com/@DumbMoneyHunter/videos Website:...

In this conversation, Wayland, CEO of Copperbox, discusses the importance of leadership development in private equity portfolio companies. He emphasizes the need for transformational change in leadership roles, the challenges of adapting to the fast-paced private equity environment, and the integration of AI in leadership development. He highlights the balance between human connection and AI in le...

In this conversation, Anand Chaturvedi, founder and CEO of Carify AI, discusses his journey in creating a business automation platform for long-term care. He shares insights on customer acquisition, the importance of purpose in entrepreneurship, and the lessons learned from his experiences. Anand emphasizes the need for flexibility in work culture and the significance of focusing on outcomes rathe...

Jeroen Reuven Bours is the founder and CEO of Darling, a creative agency built on one thing big agencies forgot: real service. In this episode, he shares why he started Darling when everyone told him not to, how he ended up working with Steve Jobs and the rules that guide his team.

In this conversation, Donny Mashiach, founder and CEO of Warrior Group, discusses his journey from starting a food business to creating a strategic finance firm that helps founders scale their businesses. He emphasizes the importance of financial leadership, the unique structure of his team, and the significance of referrals in client acquisition. Donny shares insights on refining products before...