How They Win

Romain Osman
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  • Entrepreneurship
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The untold strategies behind successful businesses.

  1. 07/27/2025

    17 Years, 900 Clients, Still Bootstrapped – Jonathan Brun

    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: https://www.linkedin.com/in/jonathanbrun/ Website: https://nimonik.com/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    29 min

  2. 07/27/2025

    From Startup to $100M Exit in 4 Years – Ben Faw

    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.linkedin.com/in/benfaw/ X: https://x.com/btfaw AdVon Commerce: https://www.advoncommerce.com/ Dynamism Capital: https://dynamism.capital/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    31 min

  3. 07/20/2025

    How EduCup Scaled to 2.5M Students – Carlos Raul

    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 EduCup. 🔗 Find Carlos Raul here: LinkedIn: http://www.linkedin.com/in/carlos-raul Instagram: https://www.instagram.com/educupofficial/ Website: https://educup.io/en/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    33 min

  4. 07/20/2025

    How Savi is Saving Thousands for Employees – Aaron Smith

    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/aaron-smith-🎓-77bbb89 Website: https://www.bysavi.com/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    22 min

  5. 07/19/2025

    From Deloitte to Copact: A New Way to Create Client Value – Zach Beegal

    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 approach built on trust, outcomes, and shared success, this one's for you. 🔗 Find Zach Beegal here: LinkedIn: http://www.linkedin.com/in/zach-beegal Website: https://www.copact.ai/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    40 min

  6. 07/18/2025

    Tokenizing Real Estate and Rethinking Talent – Laurel Djoukeng

    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 didn’t work, lessons in customer acquisition, and why staying lean is a superpower. 🔗 Find Laurel Djoukeng here: LinkedIn: http://www.linkedin.com/in/djoukeng Sparc: https://sparc.world/ KeyPath: https://keypath.ai/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    42 min

  7. 07/17/2025

    Process Beats Personality: Sales Lessons from 700+ Clients – Will Fuentes

    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-fuentes-drivefastersales Website: https://maestrogroup.co/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    28 min

  8. 07/17/2025

    From $0 to $10M: Building a Programmatic Ad Agency – Mike Tyler

    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.linkedin.com/in/miketylerg Website: https://www.warroominc.com/ 🎙 Connect with Romain Osman: LinkedIn: https://www.linkedin.com/in/romainosman/ Website: https://fiveelement.co/

    25 min
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The untold strategies behind successful businesses.

Information

  • Creator
    Romain Osman
  • Years Active
    2K
  • Episodes
    22
  • Rating
    Clean
  • Copyright
    © Romain Osman
  • Show Website
    How They Win