The Entrepreneur’s Cut

Mac
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  • Entrepreneurship
  • Updated Weekly

The unfiltered side of entrepreneurship. Each episode dives into the real journey of founders — the wins, the losses, the pivots, and the lessons learned along the way. From billion-dollar builders to undiscovered hustlers, The Entrepreneur’s Cut gives entrepreneurial minds a front-row seat to the raw stories that don’t make the highlight reel.

  1. 4d ago

    Why Most Men Are Stuck at Zero: Giles Denning

    Giles Denning spent 10 years running nightclubs. Now he runs a free fitness trade show that pulls thousands of the industries biggest names together, and he's building something he believes the men's space is missing entirely. His take: men's mental health has plenty of reactive solutions but nothing proactive. So he's building it. In this episode we cover: The trade show model: why PerformX is free to enter and still turns a profitHow he rebuilt everything in lockdown after he quit a job his gut told him not to takeThe men's mental fitness idea, and why most men are sitting at zeroGoing from victim to creator, and the mindset shift behind itWhy a hard workout plus proper men's work beats a retreat most blokes would never bookGiles also gets honest about the stomach illness he carried for years, the one that turned out to be pushed-down stress rather than an allergy, and what fixed it. Giles Denning runs brand at PerformX, the business of fitness show, now into its sixth year and drawing 5,000+ people to the NEC. He's also building Habitual, a men's mental fitness club that blends training with men's work. Over a decade in the UK fitness industry, from gym marketing to nightclub branding to events. Follow The Entrepreneur's Cut wherever you listen. Connect with Giles: instagram.com/giles_denning

    1h 16m

  2. May 30

    What VCs Actually Want (And Why Most Founders Get It Wrong) with Sam Marchant

    Most founders think they're not getting investment because their pitch deck isn't good enough. Sam Marchant says that's almost never the reason. As a VC partner who's backed north of 100 companies, he's pretty clear on what actually kills a raise before it starts. In this episode we cover: Why VC is purely growth capital and why judging your business by whether you can raise it is a mistake most founders makeThe bar Sam's fund 21 Ventures actually sets before writing a cheque. all four of their last investments came in at over £1 million ARR with exited founding teamsWhy 90% of founders reaching out for investment have a skill gap problem, not a funding problem, and why giving them money doesn't fix itHow Sam decides whether to back a founder in the first 30 minutes of a call and why the rejection is almost always about the person, not the productThe one thing that can never be outsourced, no matter how early or how big the business isSam Marchant is a partner at 21 Ventures, a venture capital fund. He's also co-founder of Scaling MENA, a media company covering the startup ecosystem in the region. He previously co-founded and exited a CPG business and has been investing at angel and fund level ever since. Follow The Entrepreneur's Cut wherever you listen.

    49 min

  3. May 14

    How Will Pringle Went from Rejected Junior to Top Recruitment Firm Boss

    Will Pringle dropped out of university after 8 weeks, took a £1,000 pay cut to break into recruitment. Now he's a group MD with 20+ staff and the best reputation in his market. In this episode we cover: Why Will turned down the recruitment firm that rejected him years earlier when they called him asking for businessHow four of his top consultants walked out in one go, taking over £1 million in fees with them, and how the replacement team is now performing 25% higher than they ever didThe moment the imposter syndrome hits hardest. Spoiler: it's not when things are going badlyGoing from 84 kilos with abs to 116 kilos at his peak, and what that actually looked like in practiceHis advice on when to spend the money on the car, the holiday, the nice thing. and why buying the thing below what you really want costs you more in the long runWill Pringle is the group managing director of Big Blue Search, a specialist recruitment agency in the commercial interiors and fit-out space. He's also co-host of the Getting Shit Done podcast. He's been in recruitment for 10 years, eight of them at Big Blue. Follow The Entrepreneur's Cut wherever you listen. Connect with Will: linkedin.com/in/will-pringle-74ab76112

    51 min

  4. Feb 20

    Why Successful People Can't Find Love — with Matchmaker Siobhan Copland

    She's helped countless professionals find lasting love — but what professional matchmaker and dating coach Siobhan Copland reveals in this conversation might surprise you. The biggest barrier to meaningful relationships isn't your schedule, your standards, or your success. It's your willingness to be seen. In this raw and eye-opening episode, Siobhan breaks down why high-achieving women often lead with masculine energy and push love away, why men inherently want to feel useful (and what happens when they don't), and the real meaning behind intimacy that most people get completely wrong. If you've ever wondered why you keep attracting the wrong person — or no one at all — this one's going to hit different.

    52 min

  5. Feb 12

    The Care Crisis No One's Talking About with Kevin Humphrys, CEO of Oakland Care Group

    Kevin Humphrys has spent years fighting for an industry that keeps millions of people alive — yet most of society still looks the other way. In this episode, Kevin pulls back the curtain on what's really happening inside the UK's social care sector: chronic underfunding, a massive PR problem, and a workforce that deserves far more recognition than it gets. Kevin shares how he fell into social care almost by accident, why he stayed and what needs to change before the system reaches breaking point. We talk about the misconception that care work is low-skilled, why the media only covers the horror stories, and what a proper career path in social care could actually look like. If you've got parents, grandparents, or anyone you love who might need care one day — this one matters. Kevin also leaves you with one simple thing you can do right now to help push for change.

    54 min

  6. Jan 23

    From Doctor to Serial Entrepreneur

    Dr. Emil is a former medical doctor turned serial entrepreneur who's failed more businesses than most people start. Now he runs a longevity and biohacking company helping men optimise their lives. This was a high-energy conversation about doing what brings you joy, learning to dance along the lines of your limits, and why playing it safe is the riskiest thing you can do. Strap in for this one. You can follow Dr. Emil here: https://www.instagram.com/dremilofficial/ You can follow your host Mac here: https://www.instagram.com/themacademic/

    34 min

  7. Jan 16

    From Corporate Pressure to Inner Freedom - The Conversation Every High-Performing Man Needs

    What if the very drive that made you successful is the same thing slowly destroying your peace, your health, and your relationships? In this raw and deeply confronting conversation, Gary Allman opens up about his collapse under corporate pressure, the anxiety that followed, and the moment he realised hustle culture was not the answer, it was the trap. After years of chasing productivity, validation, and external success, Gary discovered a dangerous cycle he now calls “The Proving Loop.” A loop where men tie their worth to results. Where rest feels like weakness. Where success is never enough and fulfillment is always just out of reach. Together, Mac and Gary unpack: Why entrepreneurs feel an invisible pressure to constantly “prove” themselves How stress, poor sleep, and over-optimisation quietly erode mental health Why chasing metrics, money, and online validation leads to emptiness—not freedom And the uncomfortable truth: you were never actually in control—and that’s the key to peace Gary also reveals the thinking behind his upcoming book and shares practical steps men can take right now to step off the loop, reclaim balance, and build a life that feels meaningful—not just impressive. If you’ve ever thought: “Once I achieve X, I’ll finally feel okay” “I can’t slow down—people are watching” “Why am I successful but still exhausted?” This episode will hit uncomfortably close to home. Listen now. before the Proving Loop costs you more than your productivity.

    47 min

  8. Jan 13

    From the Stage to the Boardroom: Owen Ashby on Productisation, AI, and Not Losing Your Identity

    Founders often lose themselves in the grind of building a business, forgetting that entrepreneurship is as much about self-actualisation as it is about revenue. In this episode, Owen Ashby shares his unconventional journey from acting to accidental entrepreneurship, offering a masterclass on how to scale without burning out. The conversation explores the "productisation" of services—the essential shift required to move from a manual hustle to a scalable asset. Owen also breaks down the evolving landscape of AI, explaining why it represents both a significant challenge and a major opportunity for new businesses. Whether you are navigating product-market fit or maintaining the human element in an automated world, this episode provides a roadmap for sequential problem-solving and sustainable growth. In this episode, you’ll learn: Why narrowing your focus is the fastest way to achieve business success.How to leverage AI as a tool for opportunity rather than a threat.The "From-To" shift: Lessons learned from transitioning between vastly different industries.Why the human element in sales and customer understanding is more critical now than ever.The importance of finding a partner who complements your specific skill set.You can connect with Owen here: https://www.linkedin.com/in/owen-ashby-a12722/ You can connect with Mac here: https://www.instagram.com/themacademic/

    54 min
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The unfiltered side of entrepreneurship. Each episode dives into the real journey of founders — the wins, the losses, the pivots, and the lessons learned along the way. From billion-dollar builders to undiscovered hustlers, The Entrepreneur’s Cut gives entrepreneurial minds a front-row seat to the raw stories that don’t make the highlight reel.

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