Risking it All

Risking it All

By Barry Jolly, Andy McDade, Brian McGillBusinessMarketing
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Risking it All episodes

  • From Selling Courses With No Product to Buying 7 Businesses | Martin Lightbowne

    This week on The Risking It All Podcast, we sat down with Martin Lightbowne, Managing Director of On Point Finance Group — and a true M&A powerhouse.🚀 Martin has personally completed 7 business acquisitions and now helps a mastermind full of dealmakers to structure and finance their own deals — often with none of the buyers own money down.🎙 But his story didn’t start in finance. He began as a manufacturing improvement consultant at global giants like Shell and Colgate, before pivoting to the U.S. to sell digital marketing courses — making over 70 sales before he even had a product ready to ship!In this episode, Martin shares:✅ How to buy businesses using other people’s money✅ The #1 mistake first-time acquirers make✅ Why his time at Shell & Colgate taught him how to spot hidden profits in any company✅ The exact strategy he teaches M&A entrepreneurs todayWhether you’re a business owner, investor, or future dealmaker — this episode is PACKED with practical insights.🔔 Don’t forget to subscribe for weekly interviews with entrepreneurs who are risking it all to build something great.

    1 hr 53 min
  • Leaving Banking to Build a Business – Dinesh Hallan’s Journey | Risking It All Podcast

    Dinesh Hallan left a successful banking career to build DA Accountants from the ground up. In this episode of Risking It All Podcast, we talk about his journey as the son of immigrants in Glasgow, his career shift from engineering to accountancy, and how he took the leap into entrepreneurship.


    Dinesh shares how he secured his first clients, the financial mistakes he sees business owners make, and key strategies to keep your business finances in check. From working with fish farms to aerosol can manufacturers, his career in accountancy has been anything but ordinary!


    If you’re an entrepreneur or business owner looking to understand the financial side of running a business, this episode is for you.


    🎧 Follow & Subscribe for More Business Stories!

    1 hr 23 min
  • Year One Recap: The Highs, Lows & Lessons from our first year as podcast hosts!

    In this special year-end episode, Barry Jolly and Brian McGill, cohosts of the Risking It All Podcast and owners of Jolly Media Marketing, reflect on their journey as podcast hosts over the past year.

    They dive into the highs and lows of podcast hosting, sharing behind-the-scenes stories, challenges, and the incredible benefits podcasting has brought to their careers and lives.
    Thinking of starting your own podcast? Barry and Brian offer invaluable tips and insights for anyone considering launching a business podcast. This episode is a must-watch for entrepreneurs, podcast hosts, and fans of the show!
    🎉 Thank you for an amazing 2024! We appreciate all our guests, listeners, friends and family support so far!
    Stay tuned for more episodes in 2025. Don’t forget to like, comment, and subscribe to join us on this journey.

    1 hr 1 min
  • Ep:31: Breaking Barriers to Build an Agency Empire: John Loudon’s Path to Creative Success

    In this episode of the Risking it All Podcast, we dive into the incredible story of John Loudon, Managing Director and Founder of Hybrid Anchor.

    Starting his career in call centers, John overcame countless rejections before breaking into the creative industry as a graphic designer.
    With a passion for web development and an entrepreneurial spirit, he has since built a thriving digital agency empire, successfully scaling his business and acquiring others.
    John shares candid insights into his journey, including:
    * His family influences like his father, who was an engineer; his grandfather, who was a programmer and his uncle who was a web developer
    * How he started his career in a call centre and his early difficulties breaking into the creative industry
    * Progressing to a senior designer role.
    * His high-risk approach to his first business and how he wouldn’t recommend it to budding entrepreneurs.
    * The challenges of navigating failed partnerships
    * Strategies for breaking into competitive industries
    * Lessons from growing and acquiring businesses in the creative sector
    This episode is packed with inspiration for aspiring entrepreneurs, business owners, and anyone with big dreams.
    Follow more of John’s journey and discover more about what his current business offers by connecting with him on LinkedIn - https://www.linkedin.com/in/jloudon/
    👉 Don’t forget to like and subscribe for more episodes!

    1 hr 37 min
  • From Prison to £1.7M in revenue: Michael Tonner's Inspiring Journey | Risking It All Podcast

    In this week's episode of Risking It All, we sit down with Michael Tonner, the founder and managing director of Matchless Energy Group, a leading eco and renewables installer based in Scotland 🏴󠁧󠁢󠁳󠁣󠁴󠁿

    Michael shares his incredible story of transformation, from struggling in school and facing time in prison in his youth, to becoming a successful gas engineer and launching his own thriving business.
    He reveals how he built Matchless Energy from the ground up, growing it to an impressive £1.7 million in revenue last year. Tune in for an inspiring conversation about resilience, second chances, and the power of entrepreneurship in the renewable energy sector.
    Don't forget to like, subscribe, and hit the bell for more stories of people who risked it all and came out on top!
    #RiskingItAll #Entrepreneurship #RenewableEnergy #MatchlessEnergy #Inspiration #Scotland #Podcast #SuccessStory #GasEngineer #EcoBusiness

    1 hr 15 min
  • Ryan Smith on Building a Care Home Empire & Leading Through Crisis | Risking It All Podcast

    In this episode of Risking It All, we sit down with Ryan Smith, Managing Director of Keane Premier Group, to explore his incredible journey from studying engineering to working in telecoms sales, and eventually joining the family business his mother started in the care industry. Ryan shares how they built a thriving business with both elderly care homes and adult care services, focusing on providing care for the most vulnerable.

    Ryan opens up about the challenges of acquiring other businesses in order to grow, the emotional toll of managing a care home, and the intense struggles faced during the COVID-19 pandemic. If you're a business owner, entrepreneur, or simply interested in the care home industry, you’ll learn invaluable lessons about risk-taking, resilience, and leadership.
    Don’t forget to subscribe for more inspiring business stories!

    1 hr 25 min
  • How Nick Sherman Built California’s Largest Solar Service Business | Risking It All Podcast

    In this episode of the Risking It All Podcast, we sit down with Nick Sherman, CEO of EnergyAid, California's largest solar and battery service provider. Nick shares his journey from a collegiate golfer and failed business owner to building a thriving solar service company. Learn the ins and outs of the solar market in California, the incentives that make solar affordable, and the business models that helped him scale his company. If you're interested in how to grow a successful business, especially in the solar industry, this episode is a must-watch!

    🔑 Topics Covered:
    How California leads the way in solar adoption both in the US and worldwide
    Incentives and financing models for solar installations
    Nick’s personal business growth journey
    Tips for maintaining and servicing solar systems
    🎯 Watch the full episode now to get expert advice on scaling a business and mastering a service!
    📌 Subscribe for more episodes of the Risking It All Podcast!

    1 hr 22 min
  • The Art of Buying and Selling Businesses with Jamie Simpson of Monopoli Capital

    In this episode, we sit down with Jamie Simpson, a leading business investor and Partner at Monopoli Capital. Jamie takes us through his remarkable transition from a call center employee to founding and selling a successful wheelchair taxi service.


    He shares expert insights on buying and selling businesses, emphasizing the significance of planning your exit strategy from the start and setting up effective systems to boost growth and value. Jamie also reflects on his mentorship experience with the legendary Dan Peña and how continuous self-development has fuelled his entrepreneurial achievements.


    Tune in for a casual and insightful conversation filled with practical tips and stories that will inspire and guide current and aspiring entrepreneurs, business owners, and anyone interested in the art of business acquisition and sales.

    1 hr 23 min
  • Ep26: From Family Business to 20+ Investments: Steven Pettigrew's Road to Success | 💼

    🌟 Get inspired by Steven Pettigrew's incredible journey from family business roots to becoming a top business investor and turnaround specialist! 🌟

    In this week’s episode, we sit down with Steven Pettigrew, co-owner of Monopoli Capital, to explore his entrepreneurial path . Steven started out in his parents' business, which peaked at a staggering £35 million in revenue, and now, he has invested with his business partners in over 20 businesses, including some who need rapid turnaround. 🏢💡
    Steven shares the ups and downs of his journey, including:
    💼 Learning the ropes in a thriving family business
    🚚 Building and exiting his own transport and logistics venture
    🤝 The art of turning around distressed companies through Monopoli Capital
    ✨ Steven's story is filled with real-world insights and inspiration for anyone looking to grow in the business world. Whether you're an aspiring entrepreneur or a seasoned business owner, this episode is packed with valuable lessons you won’t want to miss!
    This episode is sponsored by Workwear & P.P.E Supplies :
    Check out their website and be sure to message them to take advantage of their incredible 9 item bundle, with free embroidery and setup with your company logo for just £99:
    https://www.wwppe.co.uk/
    👍 Like, comment, and subscribe for more down-to-earth, inspirational stories every week! 👍
    #StevenPettigrew #MonopoliCapital #BusinessTurnaround #Entrepreneurship #Inspiration #BusinessGrowth #Podcast

    1 hr 27 min
  • 🚀 From Finance to Football Agent: Michael Savage's Inspiring Journey 🌟

    Join us in this engaging episode as we sit down with Michael Savage, the founder and director of Channel Finance Group and a FIFA-registered football agent. Michael shares his incredible journey from a passion for numbers and finance to becoming a key player in the football industry. We delve into his story, discussing his career, how he transitioned into being a football agent, and the challenges he faced, including overcoming a brain tumour.


    Discover how Michael's fascination with time management has been a crucial driver of his success and how he's building his business into a multifaceted finance group. Don't miss out on this inspiring conversation!


    👉 Like and subscribe for more amazing stories!

    🔔 Listen to the full episode now and share your thoughts in the comments!

    1 hr 45 min

About Risking it All

From the publisher's feed

"Risking It All" is a weekly podcast that explores the real stories of those who have dared to venture into the world of entrepreneurship. Our guests come from diverse backgrounds and industries, sharing their unique experiences, challenges, and triumphs in building their careers and businesses.