Digital Social Hour: Michael Macdonald – Why Most Entrepreneurs Fail Before They Even Start | DSH #1679

Host: Sean Kelly
Guest: Michael Macdonald (Co-Founder of Earn Your Leisure)
Date: December 12, 2025

Episode Overview

This episode features an in-depth, high-energy conversation between Sean Kelly and Michael Macdonald, co-founder of the acclaimed platform and event Earn Your Leisure. The central theme is why most entrepreneurs fail before they even start, drawing from Michael’s personal journey, business methodology, and his philosophy of legacy, leadership, and community. The dialogue dives deep into the realities behind successful entrepreneurship, the importance of mindset and foundation, the strategic use of platforms, the evolving event and podcast space, and the personal sacrifices behind notable success stories.

Key Discussion Points & Insights

1. Vision, Manifestation, and Tangibility of Goals

• Manifesting Success: Both Michael and Sean agree on the power of writing down and verbalizing goals as a method of manifestation.
  • Michael: “It’s not real unless you write it down. All my goals, I write down...now I have something tangible that I can look at every single day until I complete that mission.” (00:13, 04:13)
• Practical Manifestation: Acting on goals means translating vision into actionable, visible steps.

2. The Power of Community and Staying Grounded

• Family & Loyalty: Michael emphasizes bringing his family and childhood friends into his journey and business.
  • “The only way, the people that you grew up with, your family, your friends. Gotta stay true to who you are.” (00:47)
• Leadership Philosophy: True leadership is inspiring others to believe in themselves, not just in the leader.
  • “A true leader will get people to believe that they could be a part of the vision...I have to get them to believe in themselves.” (16:15)
• Friendship & Business: Business can expose real friendships, and putting friends in the right roles is pivotal.
  • “Your friendship—the business is going to expose that friendship.” (18:13)

3. Building Earn Your Leisure – The Event & Content Game

• Evolution of Invest Fest: Earn Your Leisure’s event grew to 25,000 attendees with minimal ad spend, focusing on organic growth and serving the community.
  • “We probably spent $9,000 on ads. That’s it...the way we do business is different and that’s why we’ve been able to be so successful.” (07:08)
• Being Hands-On: Unlike large brands, Michael and his partners are intimately involved in all operations, optimizing costs and steering impact.
• Financial Literacy as a Core: EYL and Invest Fest challenge the status quo, making financial education mainstream within their community.

4. Longevity over Trends & Sustainability in Content

• Against ‘Momentary’ Models: Michael critiques the trendy “challenge” model in business, preferring the grind of regular, value-driven engagement.
  • “...we have a live show every single week, right. We’re building moments, right. We’re building momentum...it’s an everlasting moment.” (07:23)
• Consistency is King: Sean and Michael both stress that most people quit when results don’t materialize quickly, leading to high failure rates in podcasts and business.

5. Metrics, Ownership, and Data

• Understanding the Game: They break down what makes a podcast #1 (active subscriber growth, not just listens).
  • “People just think it’s the listeners…no, it’s the podcast that get the most subscribers from Wednesday to Tuesday. Simple as that.” (10:35)
• Owning the Platform & Data: Real power lies in owning your own brand/platform and direct data access, reducing risk of getting ‘canceled’ or de-platformed.

6. Risk, Sacrifice, and the Dark Side of Entrepreneurship

• Personal Sacrifice: Both admit to losing sleep, friends, relationships, and even health to grow their businesses.
  • “Success comes with sacrifice. And it might be sacrifice friendships because I don’t spend enough time with you...I’m 80% of my vision and 20% of anything else.” (20:24)
• Foundations Matter: Many entrepreneurs fail from the outset by building on a flawed foundation or business model.

7. Money, Motivation, and Generational Wealth

• More Than Money: Michael distinguishes chasing fulfillment and legacy over pure financial motivation.
  • “Money is their motive. I already have money. It’s fulfillment for me now. It’s my legacy.” (41:57)
• Generational Responsibility: The conversation challenges the notion of what’s truly “life-changing” wealth, emphasizing long-term impact and preparing the next generation.

8. Using Adversity and Mindset for Advantage

• Adaptation and Perspective: Stories of losing and regaining wealth, leveraging adversity for growth, and the power of perspective.
  • “You said that like that was a bad thing. Most people…never had $30,000 in their life. It’s all perspective, right?” (38:58)

Memorable Quotes & Moments (with Timestamps)

• On Manifestation:
  • Michael: “It’s not real unless you write it down...when I say it and then I write it down, I could see it. It’s something real.” (00:13, 04:13)
• On Leadership:
  • Michael: “A leader, they think that you got to get people to believe in your vision. Right? But a true leader will get people to believe that you could be a part of the vision, and that’s a real leader.” (16:15)
  • “My job is to get him to believe in himself.” (15:05)
• On Entrepreneurship Sacrifice:
  • Michael: “Success comes with sacrifice...I sacrificed a lot. That’s what comes with success.” (20:24)
  • Sean: “That’s the dark side of entrepreneurship that…I guess isn’t sexy to talk about.” (22:20)
• On Motivation Shifting:
  • Michael: “Money is their motive. I already have money. It’s fulfillment for me now. It’s my legacy…I’m doing this because it’s a passion of mine now.” (41:57)
• On Consistency:
  • Sean: “The show makes about 150 grand a month and I don’t run any ads. It’s all the platform I built.” (08:21)
• On Failure Rates in Podcasting:
  • Michael: “A lot of people do. That’s why when people say the podcast space is oversaturated, it’s not. Because…It’s gonna be a lot of podcasts that come and go…” (09:15)
• On Perspective:
  • Michael: “You said that like that was a bad thing. Most people…never had 30,000 in their life.” (38:58)
• On “Word Vomit” & AI:
  • Michael: “We came up with something called word vomit…record all your thoughts…take the transcript and tell ChatGPT to organize these thoughts and put them in a way that is understandable and digestible.” (43:40)
• On Content Creation:
  • “How can you make the right content if you’re not the content? You have to become the content to make the right content.” (30:27)
• On Dreaming Big:
  • Michael: “Don’t dream too small. I love that my dreams were too small there.” (51:14)
• On Building Your Own Stage:
  • “How do I get on a stage? Build your own. Simple. Build your own.” (53:29)

Notable and Practical Takeaways

• Write Goals, Say Them Out Loud, Make Them Tangible:
  Manifestation is action, not just wishful thinking.
• True leaders empower others:
  The real legacy is getting others to believe in and realize their potential.
• Organic Growth > Trend Chasing:
  Consistency and authenticity attract stronger, loyal communities.
• Foundation First:
  Build solid business models and systems; most failures happen due to weak foundations.
• Own Your Platform:
  Control your data and brand to reduce risk and increase value — “You can’t cancel someone who owns themselves.”
• Sacrifice is Unavoidable:
  There is personal and financial sacrifice behind every meaningful entrepreneurial journey.
• Perspective Makes the Difference:
  Success and setbacks are both relative — leverage adversity for lessons.
• Content Success Requires Authenticity and Strategy:
  “Become the content” and use data/AI (like ChatGPT) to amplify and organize creative output (“word vomit”).
• It’s a Marathon, Not a Sprint:
  Real wealth and impactful businesses are built for longevity, not momentary trends.

Important Segments & Timestamps

• [00:00–04:39] — Manifesting success; writing down goals; introduction to Michael and EYL
• [05:01–08:44] — The rise of Earn Your Leisure, building businesses with community, and the event model
• [10:14–12:57] — Understanding podcast success metrics; why so many fail; true ownership
• [14:03–17:44] — Staying grounded, family/friendship in business, authentic leadership
• [18:13–22:31] — Friendship vs. business, losing relationships, and the honest cost of pursuing vision
• [23:39–26:40] — Event space struggles, why popular businesses fail, emotion vs. logic in business choices
• [27:29–36:17] — Platform ownership, canceled culture, building from humble beginnings, generational wealth
• [41:57–46:09] — Fulfillment vs. financial motivation, leveraging ‘word vomit’ and AI for organizing ideas
• [48:27–53:00] — Memorable branding/hooking, dreaming bigger, and mastering the stage

Episode Finale: Special Offer

Giveaway: Michael offers his "Business Engine" course (normally $1,000) for free to DS Hour listeners.

• How to get it:
  • Follow Michael on Instagram (@michaeljmacdonald)
  • DM him the word “Sean”
• Offer includes: Four pillars of building a successful business (systems, business model, marketing, sales)

Closing Thought

This episode is a masterclass in real entrepreneurship: mindset, community, resilience, and authenticity are the foundation for not just starting—but surviving and thriving. Both Michael and Sean bring hard-earned wisdom, honest takes, and actionable strategies for anyone looking to launch or level up their own journey.

To Connect:
Michael Macdonald: @michaeljmacdonald

“Don’t dream too small.” — Michael Macdonald (51:14)