Greg Healy spent more than 30 years inside the global surf and action sports industry with Quiksilver and Boardriders, running regions across Asia Pacific, North America, and Europe. Before that, he was the youngest ever captain of an AFL football club in Australia, leading a team onto the Melbourne Cricket Ground in front of 100,000 people.

We cover a lot of ground here. Greg talks about what team sport taught him about resilience, what it felt like to go from critic to accountable when the board handed him the keys to fix North America, and the honest truth about leading through Chapter 11. He speaks candidly about the Rossignol acquisition, what hubris costs, and what Oaktree Capital taught him about quality growth over growth for its own sake.

"Sometimes it's never as good as you think it is. Alternatively, it's never as bad as you think it is. You're only one bad decision away from life being in a very different position than it was yesterday."

We get into the Billabong integration, the cultural friction of merging two fierce competitors, and what it actually takes to build trust across a divided team. The COVID section is probably the most honest part of our conversation. Greg was projecting confidence he did not always feel, and he is straight about that gap.

"Your coach's talks every morning just got us through. We just needed to hear someone say: we're going to be right, keep on path, just keep doing what you're doing, and we'll get through."

We also dig into founder ego, when to bring in an operator, the challenge small brands face entering markets owned by the majors, and why Greg, at 60, still wants to be in the game.

"Financially, I don't need to work, but emotionally, I certainly do. I'm not ready to hang the boots up yet."

If you are building something or running something, there is a lot in this one.

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Greg spent nearly 30 years with Quiksilver and Boardriders, covering Asia Pacific while stepping into the Americas and Europe when needed. His tenure covered the Quiksilver restructuring, Chapter 11 and transition to Oaktree Capital, and the Billabong integration. Former Boardriders CEO Dave Tanner called him a natural leader, culture carrier, and talent builder. He stepped down as CEO of APAC at Liberated Brands in August 2024.

Chapters:

00:00 Introduction

00:51 Meet Greg Healy

02:03 AFL Captain Lessons

03:33 Resilience From Sport

04:40 Fixing North America

05:40 Culture Shock Moment

07:46 Chapter 11 Reset

10:03 Ego Debt And Humility

11:54 Quality Growth Playbook

13:21 Turnaround Team Values

14:32 Cabo Momentum Shift

16:08 Acquiring Billabong

17:28 Merging Cultures Trust

21:35 Founders Ego and Operators

22:01 Leading Through COVID

26:23 Leases and Survival Detail

27:50 Lockdown Family Perspective

33:03 Quiksilver Cultural Heyday

35:25 When Global Brands Fracture

38:19 Small Brands and Channels

43:10 Why Work After Success

45:51 Advice For Stuck Founders

47:39 Global Expansion Nuances

50:24 Proudest Moments Legacy

52:03 How He Wants to Lead

53:09 Next Team And Farewell

Sara Lawhead has spent her career building things. Teams, products, brands, strategies. She has worked inside large public companies, navigated private equity environments, and managed multiple brands at a pace that left little room to think. Now she is leading Thacker NYC, a founder-led brand going after a consumer the outdoor industry has largely ignored.

"We think of life as a sport. No one is really talking to the everyday person. The outdoor industry tends to go after the core, the hardcore, the top of the mountain. But it is the everyday people that still want to get outside, still want to look the part. That is a big, unmet opportunity."

That shift, from managing six brands and fifty-plus products a year to building one brand with intention, is the backdrop for this conversation.

We cover what the outdoor market actually looks like right now, from trade show floors to retailer meetings. We get into tariffs and supply chain, and how the brands that came out ahead were the ones that started diversifying manufacturing before the pressure hit.

One of the more interesting threads is pattern recognition across categories, and what happens when private equity acquires founder-led brands.

"Once that special sauce, once that DNA has really left the business, it gets harder and harder to continue that passion and excitement. The DNA isn't there anymore. It gets sucked out."

Sara has a clear point of view on where brands lose the thread, how innovation is misunderstood, and what real partnership with specialty retail actually requires. She also talks about the BIRDS communication framework, a tool she uses with every team she joins.

"As a leader, you have to have the awareness of who you are talking to and how they receive information. The more you understand who you are talking to and how they operate, the better the business will go. Once you know it, you actually have to do it. That is the second battle."

We close on what Sara would tell someone early in their career.

"Figure out what you are good at. Not what you think is cool, not what everybody else is telling you to do. Chase that."

A conversation about building something real, reading the market honestly, and knowing when to move and when to wait.

Chapters:

00:00 Introduction

02:07 Founder Led Pace Shift

04:04 Trade Shows And Market Signals

06:15 Life As a Sport

08:41 People-first Building Blocks

11:02 DIY Mindset No Roadmap

12:33 Athlete Pressure Lessons

15:32 Compassionate Leadership Birds

18:42 Top to Top Retail Strategy

20:47 Tariffs and Supply Diversification

23:36 Pattern Recognition In Categories

26:52 Winning Retailer Confidence

29:28 Partnership with Specialty Retail

30:25 Staying True to Brand

31:29 Compromise Without Dilution

33:10 Redefining Innovation

34:22 Colorways That Sell

35:21 Decide and Ship

37:16 Pleasant Persistence

39:58 Follow Up Early

40:48 Relationships Beat Automation

41:28 Hiring a Sales Agency

42:36 Conviction Without Playbook

47:13 Slow Build Strategy

49:45 Healthier Leadership Mindset

51:53 Entrepreneurship and Expansion

52:35 Fashion Meets Function

57:25 Books That Shape Focus

59:22 Advice for Year Two

01:02:19 Go Until Stopped

01:03:24 A Good Life Vision

I'm excited to share my conversation with Mike Cachat, a pioneer in our industry and someone I've known for many years.

Mike's journey from building a small bike repair business as a teenager to founding Jenson USA is a testament to seeing the future, perseverance, and innovation.

This episode is for you if you enjoy learning about the ups and downs of entrepreneurship and leadership or seek inspiration in growth and resilience.

Streaming on all podcast platforms, or watch on YouTube & Spotify.

Enjoy your day!

🏔 🚲 🌿 – Tony