Risking it All

Barry Jolly, Andy McDade, Brian McGill
  • 4.3 (3)
  • MARKETING
  • UPDATED WEEKLY

"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. Whether you're an aspiring entrepreneur, a seasoned business professional, or simply fascinated by the world of business, "Risking It All" offers insights and inspiration. Join us as we delve into the into the highs and lows of business, learning from real people stories.

  1. 22 JAN

    Jolly Media Marketing - Review of 2025 and Future Plans

    In this special episode of Risking It All, Jolly Media Marketing directors Barry Jolly, Brian McGill, and John Conway take the lead, as they unpack the pivotal experiences of the past year and the bold strategies driving them into 2026. From navigating personal and professional highs and lows, to pivoting their agency’s focus in the renewables and lead generation space, this conversation is rich with insight and inspiration for business owners, marketers, and ambitious founders alike. 🎙 In this episode, we talk about: 🔹 The challenges and realisations that reshaped their leadership and business strategy 📈 Lessons learned from evolving JMM’s services and market positioning 💡 How resilience and innovation are fueling their 2026 vision 🚀 Actionable insights for entrepreneurs navigating change and scaling with confidence Whether you’re building a company, leading a team, or simply passionate about growth and leadership, this episode offers raw reflections and strategic perspectives straight from agency directors who are risking it all to make an impact. 👉 Tune in now for an honest, forward-thinking conversation with Barry, Brian, and John.

    1h 38m

  2. 9 JAN

    Risking It All with Stuart Davie: Scotland’s Renewable Energy Trailblazer -

    Risking It All with Stuart Davie: Scotland’s Renewable Energy Trailblazer - In this episode of Risking It All, we sit down with Stuart Davie, the driving force behind Solar Dynamix UK, a Scottish-based renewable energy and efficiency solutions business, helping homeowners and communities save energy and reduce costs. Stuart takes us through: 🔋 His vision for sustainable energy and what inspired him to build a people-focused business ☀️ The challenges and risks of growing a renewable energy company in today’s market 📉 Key business lessons on team leadership, customer trust, and scaling responsibly 📈 Practical insights for entrepreneurs and leaders looking to turn mission into momentum Whether you’re passionate about purpose-driven business or navigating your own growth journey, Stuart offers honest lessons on risk, strategy, and making an impact. 👉 Tune in to discover how one Scottish entrepreneur is powering change: one roof at a time.

    1h 30m

  3. 19/12/2025

    Peter Barclay: Changing the perception of sales, one business at a time all across Scotland

    From Sales Struggles to Strategic Growth: Peter Barclay, Sales Geek Scotland, Helping change the perception of sales.. In this week’s episode of Risking It All, we sit down with seasoned business leader Peter Barclay, a sales strategist and fractional sales director with over 30+ years of experience helping businesses grow from the inside out Peter shares the real-world lessons that shape his journey from his early days in sales, to helping both family-run firms and global PLCs scale their operations and now, helping SME's all across Scotland to improve sales output using effective sales leadership & training, You’ll hear: 🔍 What it really takes to build a high-performing sales engine 📈 How to turn sales challenges into strategic business wins 💡 The mindset shifts that separate passive leaders from growth drivers 🎯 Actionable insights you can apply today to boost your revenue and team performance Whether you’re a founder, sales leader, or entrepreneur looking to scale smarter, this conversation unlocks the practical playbook for sales-led growth. 👉 Don’t miss Peter’s stories of risk, resilience, and results and how embracing strategic sales leadership can transform your business.

    1h 46m

  4. 27/11/2025

    “Revolutionising Boating: Mike Lally on Leadership, Innovation & Freedom Boat Club Loch Lomond"

    On this episode of Risking It All, we’re joined by Mike Lally, Founder and Managing Director of Freedom Boat Club - Loch Lomond, a company transforming how people experience boating. Mike has spent his career building and scaling service-based businesses, blending operational expertise with a passion for innovation. At Freedom Boat Club, he has pioneered a membership-based model that makes boating accessible, convenient, and community-driven, challenging the traditional boat ownership model. In this episode, we explore: ✅ Mike’s journey into entrepreneurship and leadership ✅ How Freedom Boat Club disrupts the boating ownership industry with a shared-fleet, membership model ✅ The challenges and opportunities of scaling a leisure and corporate lifestyle business in competitive markets ✅ Building community, sustainability, and customer experience into a thriving service brand ✅ Key lessons for entrepreneurs and leaders looking to innovate in traditional industries Whether you’re interested in entrepreneurship, scaling a membership business, or simply curious about the future of boating, this episode is full of insights and inspiration from someone who’s risking it all to redefine an industry. 🔔 Subscribe to Risking It All for more stories from entrepreneurs and business leaders who dare to take bold risks 💬 Comment below and share your thoughts or questions for Mike, we may feature them in a future episode!

    2h 4m

  5. 22/07/2025

    📍From Rural Pakistan to HealthTech Pioneer 🚀 Mubbasher Khanzada’s Journey of Grit, Growth & Purpose

    Mubbasher Khanzada is the Founder & CEO of Welltime Ltd. and a proud Saltire Fellow. Growing up in a small village in Pakistan , Mubbasher was deeply shaped by family values and a drive to succeed that led him to travel halfway across the world to Scotland for education. That decision would lay the foundation for a career dedicated to transforming digital healthcare experiences Today, Welltime helps clinics streamline bookings, automate patient journeys, and improve engagement — with innovation at its core 🌍🔍 What you’ll learn in this episode:• 💪 How Mubbasher’s upbringing instilled resilience, discipline, and long-term vision• 🚪 His bold decision to transition from traditional work into tech entrepreneurship• 🧠 The founding story of Welltime and its impact on UK healthcare providers• 🌐 What the Saltire Fellowship taught him about leadership and scale• 🎯 Practical insights on growth, mindset, and navigating uncertainty• 🤖 Progressing exciting projects in AI, helping businesses adopt new exciting technology to push them forward and be more efficient👉 Don’t forget to subscribe to Risking It All for more real founder journeys full of risk, resilience, and reinvention 🎧

    2h 12m

  6. 11/07/2025

    🎙 From Bedroom Startup to Creative Agency CEO: Jamie Steel on Risking It All for Squinty Pixels

    Our guest in this episode is Jamie Steel, founder and managing director of Squinty Pixels, a dynamic creative agency based in Glasgow. Jamie grew up in Paisley in the 80s and 90s and began his career in the structured world of corporate marketing. Over the years, he held leadership roles across construction, manufacturing, and engineering sectors — managing multimillion-pound marketing strategies and large cross-functional teams. But in 2022, Jamie made a bold move. With nothing more than a bedroom setup, a drone, and a vision, he walked away from the corporate ladder to launch Squinty Pixels — a full-service creative agency delivering web design, branding, video production, and aerial content across the UK. In this episode, we unpack: 📈 Jamie’s early career journey from corporate marketing to creative entrepreneurship 🎯 Why he gave up a stable executive role to start Squinty Pixels from scratch 🚁 How becoming “the drone guy” opened unexpected doors in content production 🤝 The principles that drive his business today: transparency, collaboration, and adaptability 🎬 His creative process, real client stories, and how he’s grown a thriving team from the ground up Whether you're a creative professional, a corporate employee dreaming of something more, or just curious about what it really takes to start your own agency — Jamie’s story is packed with insights, honesty, and inspiration.

    1h 55m

  7. 27/06/2025

    From the Mining Town to Clean Energy CEO: John Conway’s Leap of Faith

    This week on Risking It All, we sit down with John Conway—a man who grew up in a mining family on the outskirts of Edinburgh and charted an unlikely path from telecom production lines to becoming a clean energy entrepreneur.John shares how he made the leap from managing teams in telecommunications to breaking into solar with eco2solar, rising to Sales Director, and later working with Sunamp and Powergreen Renewables. Today, he’s the co-founder and Managing Director of the Commercial Solar Exchange, where he’s helping businesses navigate the energy transition.In this conversation, John opens up about:✅ The realities of leaving a stable corporate career✅ Lessons learned in business development and sales leadership✅ Challenges and opportunities in the renewable energy sector✅ What it really takes to build a company in clean energyWhether you’re considering your own career pivot, want to understand the renewable energy industry better, or just love hearing the raw truth about entrepreneurship, this episode is for you.🎧 Listen now and subscribe for more conversations with people who risk it all to build something new

    2h 1m
  8. From Selling Courses With No Product to Buying 7 Businesses | Martin Lightbowne

    27/05/2025

    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.

    1h 53m
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Ratings & Reviews

4.3
out of 5
3 Ratings

About

"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. Whether you're an aspiring entrepreneur, a seasoned business professional, or simply fascinated by the world of business, "Risking It All" offers insights and inspiration. Join us as we delve into the into the highs and lows of business, learning from real people stories.

Information

  • Creator
    Barry Jolly, Andy McDade, Brian McGill
  • Years Active
    2024 - 2026
  • Episodes
    41
  • Rating
    Explicit
  • Copyright
    © Barry Jolly, Andy McDade, Brian McGill
  • Show Website
    Risking it All