Podcast Summary: Unemployable with Jeff Dudan

Episode: He Got FIRED… Then Built 12+ Companies (And Sold Them) With Troy Hazard

Original Air Date: February 24, 2026
Host: Jeff Dudan (Homefront Brands)
Guest: Troy Hazard – Serial entrepreneur, author, speaker, global president (Entrepreneurs’ Organization), franchising expert

Main Theme & Purpose

This episode spotlights the extraordinary journey of Troy Hazard, who pivoted from getting fired as a young radio announcer in Australia to founding, scaling, fixing, and selling a dozen-plus companies across multiple industries—including media, franchising, property development, and technology. Jeff and Troy dive into the realities of entrepreneurship, the power of networks like EO and YPO, buying and exiting businesses, people-focused leadership, and the enduring importance of human connection in a world moving fast towards AI. This episode is packed with advice for aspiring business builders, seasoned operators, and anyone interested in creating value through entrepreneurship.

Key Discussion Points & Insights

1. Troy’s Origin Story: From Fired to Founder

• Early Days in Media
  • Troy’s entry into radio was serendipitous—helping his father’s fishing tackle business, he fell into weekend “bay reports.”
  • First proper radio shift came unexpectedly: “Mate, I talk for two seconds on the radio in a boat and you want me to talk for six hours?... it was just the most fun I’ve ever had.” (02:48)
• Transition to Entrepreneurship
  • Fired after a dispute with his program director—“He said, ‘how about a holiday?’ I said, ‘that’d be great.’ He said, ‘good, you’re fired.’” (04:13)
  • Early ventures: Apartment flipping with his mother, opening a recording studio, morphing into an ad agency, then investing in client franchises (pizza, real estate).

2. Iterative Learning: The Power of Failure and Partnership

• “I had an equal healthy amount of failures as we did successes along the way…” (07:28)
• Moved between launching companies and investing in distressed assets (e.g., tech company bought out of receivership in 2001).
• Concept of “we”: Business is often a team sport—Troy alternated between solo projects and strategic partnerships for shared expertise and support.

3. Entrepreneurial Peer Groups—EO, YPO, Others

• Troy’s entire trajectory was profoundly shaped by joining entrepreneur networks (Entrepreneurs’ Organization, YPO, Vistage, etc.).
• Memorable Quote:
  “After the first bottle of wine they had my attention. After the second bottle of wine they had my credit card. After the third bottle of wine I was chapter president.” (10:43)
• Troy highlights the career-altering impact of global exposure, vulnerability, and “learning from people who have no skin in your game.”
• Vital lessons in diversity of thought, cross-industry learning, and the concept of a confidential space for founder challenges.

4. Exiting, Not Just Building Businesses – The ‘Leave Meat on the Bone’ Philosophy

• Troy intentionally leaves strategic opportunities for buyers, “so they're buying into that journey, that dream... not about just selling the business, it's about selling the sexiness of the next person's dream.” (22:10)
• Exit Planning Starts on Day One:
  • “From the day we buy it or the day we move in, the exit starts on day one...” (27:13)
  • “If you don’t know what you want it [the business] to do for you, you end up working for it... it’s a job.” (27:45)
• The importance of aligning business outcomes to personal goals.

5. How Troy Evaluates Businesses

• Framework for Assessing Opportunities:
  • Look for “unsexy” businesses with untapped potential.
  • Initial diligence on distressed assets is conversations-driven—culture and people before P&Ls.
  • “You have to triangulate the reality in front of you and the piece of paper...” (25:12)

6. Leadership & People-First Management

• Troy espouses a gentle, encouraging leadership style—focusing on alignment between team members’ personal goals and business objectives.
• “I am, I suppose, a softer leader than most. I tend to encourage rather than instruct...” (33:52)
• The importance of unscripted, genuine “flybys” over strict KPI-driven reviews.

7. Human Connection Beats AI

• Advice for Young Entrepreneurs: Focus on what can’t be automated. Insert yourself at the “human handoff” in processes—where relationship and trust matter most.
• “Remind yourself that you're human. ...there needs to be that human contact... that will never go away.” (38:42)
• “If you’re not part of that human handoff...technology will take over and you'll make yourself redundant.” (39:25)

8. Insider’s View: Franchising Trends and Philosophy

• Troy’s long arc in franchising: Franchisee, consultant, franchisor, investor.
• Sees the sector as having lost focus on relationship in favor of hyping product or trend—reminds listeners that franchisees buy support and community, not just a widget.
  • “We’ve kind of forgotten the importance of that...franchising is about the relationship.” (47:54)
• “Go and find the leader you want to work with that has the vision... forget the widget.” (55:17)

9. Family, Freedom, and the “Unemployable” Life

• Troy now travels globally with his young family—homeschooling, working wherever, and reaffirming the value of flexibility that entrepreneurship brings.
• “We’ve been homeless for the last two years. So we do homeless quite well, Jeff.” (64:52)
• His global business partners simply don’t care where he is as long as value and results are delivered.

10. Quick Hits: Media, Humor, and Accessibility

• Regular commentator on the Big Biz Show (US), self-deprecating and accessible to anyone wishing to connect.
• “Business with barroom flair—we don’t take ourselves too seriously.” (68:22)

Notable Quotes & Moments

• On the value of peer groups:
  “That hour a day you spend talking to different people or even 30 minutes... those things were certainly pivotal for me and my journey. And it gave me the education I didn’t get from going to college.” — Troy (11:40)

• On business exits:
  “If I’m the smartest person in the room, I’m in the wrong room.” — Troy (22:10)
  “Know what you look like when you grow up...” — Troy (00:00, 73:54)

• On “leaving meat on the bone”:
  “You don’t have to make it sexy yourself. You just have to make it look good in their eyes so they fall in love with it... that’s where we’ve found the most powerful exits.” — Troy (22:10)

• On futureproofing against AI:
  “There will always be trades and things that technology can never take over... Keep an eye on where you want to insert yourself into that human handoff.” — Troy (38:42)

• On leadership:
  “I try to find what people really want out of life, and if I'm helping them achieve their goals, then it makes my job easier to achieve mine.” — Troy (33:52)

Timestamps for Important Segments

• 00:00 — Opening practical philosophy: “Start with the end in mind. Know what you look like when you grow up.”
• 02:20–03:54 — Falling into media, first break, transition to entrepreneurship.
• 04:13–05:12 — Getting fired; first move into property investing with his mom.
• 10:43 — The irresistible pull (and liquored push) into EO.
• 13:12–16:00 — Peer groups, confidentiality, the power of forum.
• 22:10–27:45 — Troy’s approach to buying, improving, and exiting businesses.
• 33:52–36:31 — Leadership and people: soft skills, aligning personal goals.
• 38:42–41:00 — Advice for younger entrepreneurs: Human element in the era of AI.
• 47:54–52:36 — Franchising: The lost art of relationship-first recruitment and support.
• 64:52 — On going “homeless”: Travel, family, a new model of business and life.
• 73:54 — Troy’s single best piece of advice: “Start with the end in mind. Know what you look like when you grow up.”

Highlights & Memorable Moments

• The “three bottles of wine” anecdote that led Troy to his first EO presidency. (10:43)
• Troy admitting to being a “terrible franchisee,” but turning that into a consulting superpower. (42:19)
• Jeff’s heartfelt story about his own father’s entrepreneurial struggles, and how those experiences set the foundation for his own entrepreneurial career. (56:46)
• The "flybys"—an organic approach to team check-ins, aided by a disciplined assistant. (37:06)
• Troy’s openness on post-exit life and embracing family, travel, and new forms of impact. (62:43)

Closing Advice for Aspiring Entrepreneurs

Troy’s Fastball (73:54):

“Start with the end in mind. Know what you look like when you grow up. … If you want to build, create, or own your own future, you need to know what it looks like when it’s done. … If you can answer those two questions, then at least we’ve got something to aim for.”

Contact & Resources:

• Website: troyhazard.com
• Vimeo Channel (speaking/media clips): vimeo.com/troyhazard
• Regular on the “Big Biz Show” (US cable networks)

This episode provides a blueprint for entrepreneurial resilience, the lifetime value of networks, human leadership in a technological world, and the deep satisfaction (and freedom) that comes from building your own path.