EXECS WHO RUN

Today’s guest is Phoebe Pincus — COO of Startmate, co-founder of Cheeky Run Club, marathon runner.

In This Episode:

[00:03:00] Phoebe’s “Always Swim” mantra and what it means beyond Bronte.

[00:06:00] From Women Fellowship participant to COO at Startmate.

[00:09:00] The founding story of Cheeky Run Club and rebranding running.

[00:13:00] The cultural boom of running post-COVID.

[00:15:00] Is running really a cult?

[00:17:00] Phoebe’s running origin story — from casual loops to marathons.

[00:23:00] Discipline, systems, and the myth of willpower.

[00:32:00] How running builds self-confidence through daily practice.

[00:37:00] The overlap between resilience, stress management, and running.

[00:55:00] Lessons from burnout, overtraining, and learning to “earn the right” to do more.

[00:58:00] Phoebe’s top advice for life, leadership, and running.

Pull Quote:
“Discipline isn’t forcing yourself to do hard things — it’s building systems so the good things feel easy.” — Phoebe Pincus

Follow Phoebe Pincus:

Instagram: @cheekyrunclub

LinkedIn: Phoebe Pincus

Stay Connected with Jason & Execs Who Run:

Jason Hunt: LinkedIn | Instagram

Execs Who Run: LinkedIn | Instagram

Website: execswhorun.com

Join the community: Execs Who Run Strava Group

Xavier Shay joins Execs Who Run to explore how software engineering, executive leadership, and distance running all thrive on structure, systems, and sustained effort.

From his time scaling Square in the U.S. to leading innovation at Bendigo Bank, Xavier brings deep insight into building cultures that work—and staying grounded through running.

🔑 Key Moments in This Episode:

Accidentally signing up for a half marathon on a Wednesday (and running it solo)

The shift from software engineer to manager at Square during hypergrowth

How leadership became a natural extension of systems-thinking

CEO role at Up and how the fintech was integrated post-acquisition

The benefits of running clubs and community in San Francisco and Melbourne

His most meaningful race: a 3-day 200km ultramarathon with his father

The power of consistency, simplicity, and knowing your personal operating system

Why more companies should have gyms—and how wellness builds workplace culture

Follow Xavier Shay:

Xavier Shay’s Blog: https://xaviershay.com/

LinkedIn: https://www.linkedin.com/in/xaviershay/

Twitter/X: https://twitter.com/xshay

Stay Connected with Jason & Execs Who Run:

Jason Hunt (LinkedIn): https://www.linkedin.com/in/jasonzanehunt/

Execs Who Run (LinkedIn): https://www.linkedin.com/company/execs-who-run

Instagram: https://www.instagram.com/execswhorun/

Website: https://execswhorun.com

🎧 Support the Show:

Enjoyed this episode? Please follow, rate, and review Execs Who Run on your favourite podcast platform—and share it with someone who runs toward big goals.

In this inspiring conversation, Catriona McGregor—General Counsel and executive leader at Domain—shares her remarkable journey through law, leadership, motherhood, scuba diving, and ultramarathon running.

Key Moments in This Episode:

Growing up in Scotland and England, and her winding path into law

How scuba diving in Fiji and the Galápagos shaped her spirit of adventure

Moving to Sydney and building a leadership career at Domain

Motherhood, identity, and discovering running as personal sanctuary

From a first 10K to half-marathons, trail races, and the Ultra-Trail Australia 100km

Lessons on perfectionism, fear of failure, and resilience

The parallels between long-distance running and executive leadership

Preparing for her next big challenge: the UTMB OCC race in Chamonix

Follow Catriona McGregor:

LinkedIn: https://www.linkedin.com/in/catriona-mcgregor-b1520338/

Stay Connected with Jason & Execs Who Run:

Jason Hunt (Host): https://www.linkedin.com/in/jasonzanehunt/

Execs Who Run LinkedIn: https://www.linkedin.com/company/execswhorun

Instagram (Execs Who Run): https://www.instagram.com/execswhorun

Jason’s Instagram: https://www.instagram.com/jasonzane_/

Strava Group: https://www.strava.com/clubs/execswhorun

Website: https://execswhorun.com

👉 If Catriona’s story inspired you, please follow, rate, and review Execs Who Run on your favourite podcast platform—and share this episode with someone who could use some motivation.

The world record for fastest marathon in a suit is 2:39.

Soh Rui Yong owns it. Jason Hunt wants it.

In this unforgettable episode, record-holder meets record-chaser in a conversation full of tactics, heatstroke, fashion, and mindset. If you've ever chased something ambitious—and maybe a little absurd—this is for you.

Key Moments in This Episode:

How Jason’s Guinness goal was sparked by a chance conversation and LinkedIn tag

Rui’s hilarious and harrowing suit marathon in sweltering London heat

Why the “wall hits harder” when you’re in three soaked layers

Tactical breakdown: pacing, layering, gels, hydration, psychology

Jason’s Sydney Marathon prep and what Rui would do differently next time

The global community of runners competing for this niche record

What it means to chase purpose when conventional goals no longer excite

Rui’s transition from national athlete to coach, entrepreneur, and speaker

Sponsors & Links:

Institu: – Custom-tailored suits built for performance and elegance

2nu Vision: – High-performance sunglasses engineered for runners and adventurers

Movember Fundraising Page: Donate here – Support Jason’s mission to raise funds for men’s health

About Soh Rui Yong:

Soh Rui Yong is Singapore’s national record holder across every distance from 5K to marathon—and a Guinness World Record holder for fastest marathon in a suit.

Off the track, he runs the Run So Fast Academy, helping athletes reach their peak through elite-level coaching.

Coaching: runsohfast.com

Instagram: @sohruiyong

LinkedIn: linkedin.com/in/sohruiyong

Stay Connected with Jason & Execs Who Run:

Jason Hunt LinkedIn

Execs Who Run LinkedIn

Instagram: @execswhorun

Website: execswhorun.com

🎧 Enjoying the show? Follow, rate, and review Execs Who Run, and share this episode with someone chasing a crazy dream in formalwear.

Rick Baker, co-founder of Blackbird Ventures, joins Jason to share his remarkable journey from startup founder to visionary investor, including early investments in Canva. Rick also reveals how he's harnessing AI as his personal running coach, bringing discipline and joy into his daily routine.

Jason also shares an exciting update about his upcoming world record attempt—running the Sydney Marathon in a full three-piece suit to support Movember.

Key Moments in This Episode:

Rick’s career evolution: from uncertain graduate to successful entrepreneur and influential venture capitalist.

The story behind Blackbird Ventures and their journey raising the first fund.

Identifying visionary founders early: How Rick knew Canva would succeed.

Rick’s reflections on missed opportunities (Airwallex, Employment Hero) and the lessons learned.

Embracing running as a daily ritual and discovering ChatGPT as a running coach.

Jason announces his upcoming Guinness World Record attempt at the Sydney Marathon to support Movember.

Resources & Links:

Blackbird Ventures

Movember – Jason’s World Record Attempt Fundraising Page

Join the Execs Who Run Strava Group

Follow Rick Baker:

LinkedIn

Stay Connected with Jason & Execs Who Run:

Jason Hunt LinkedIn: linkedin.com/in/jasonzanehunt

Execs Who Run LinkedIn: linkedin.com/company/execswhorun

Instagram: @execswhorun

Website: execswhorun.com

Support the Show:

Enjoyed the episode? Please follow, rate, and review Execs Who Run, and share it with someone who might be inspired to run toward their own goals.

Marie “Lootie” Leautey ran around the world. Over 28,000 kilometers. Four continents. One stroller. Zero injuries.

In this episode of Execs Who Run, Lootie shares how she went from a pack-a-day smoker to the fastest woman to circumnavigate the globe on foot—solo and self-supported. Her story is one of radical reinvention, powered by spreadsheets, strategy, and a deep curiosity about what’s possible.

Key Moments in This Episode:

The run that changed everything: from a 1km struggle to marathon training

How Greece sparked her love of triathlon and event creation

Leaving corporate leadership to build grassroots sports communities

Planning a global run like a CFO: logistics, injury prevention, and mindset

Running through COVID, crossing the Andes, and pushing through the Nullarbor

How she stayed injury-free across 28,000+ kilometers

The moment she reached the Sydney Opera House and what came next

Resources & Links:

Lootie’s Website: lootie-run.com

Lootie’s Book: Lootie’s World Run on Amazon

World Runners Association: worldrunnersassociation.org

Follow Marie “Lootie” Leautey:

Instagram: @lootierun

Website: https://lootie-run.com

Stay Connected with Jason & Execs Who Run:

Jason Hunt Instagram: @jasonzane_

Execs Who Run Instagram: @execswhorun

Jason Hunt LinkedIn: linkedin.com/in/jasonzanehunt

Execs Who Run LinkedIn: linkedin.com/company/execswhorun

Website: execswhorun.com

Support the Show:

If Lootie’s story inspired you, please follow, rate, and review Execs Who Run on your favourite podcast platform—and share it with someone who needs a little motivation to start their own run.

Former Wallabies star Ben Alexander shares the unfiltered truth of life after elite sport—and how running helped him rediscover his energy, identity, and purpose.

Key Moments in This Episode:

How Ben got selected for the Wallabies after just 6 Brumbies games

The mental and emotional collapse after the 2013 Lions series

The pain of identity loss—and why it haunted him for years

The unexpected power of Parkrun and a weekly rhythm

Founding Running for Resilience and its growing national impact

Why he now defines mental health as an energy problem, not a character flaw

The leadership lessons sport gave him—and the ones it didn’t

Resources & Links:

Running for Resilience: https://runningforresilience.org

The Dock, Canberra: https://thedockkingston.com.au

LinkedIn: https://www.linkedin.com/in/benalexander21

Stay Connected with Jason & Execs Who Run:

Jason Hunt LinkedIn: https://www.linkedin.com/in/jasonzanehunt

Execs Who Run LinkedIn: https://www.linkedin.com/company/execswhorun

Instagram: @execswhorun

Website: execswhorun.com

Support the Show:

If Ben’s story struck a chord, follow, rate, and review Execs Who Run. And share this episode with someone who needs to hear it.

Clive Ormerod has led some of the most exciting brands in Australasia—but at his core, he’s a man who finds his best thinking on the run.

In this episode, Clive joins Jason to talk about his unique journey from aspiring pilot to retail entrepreneur, Nike marketing leader, Les Mills CEO, and now global CEO of AS Colour. With stories from New Zealand, the UK, South Africa, and beyond, Clive shares the mindset shifts that have shaped his leadership and the role running plays in keeping him grounded, clear-headed, and driven.

Key Moments in This Episode:

Growing up in South Africa and discovering sport later in life

How retail and Nike shaped his leadership and love for movement

Leading Les Mills through global disruption and the COVID crisis

The link between endurance sport and leadership resilience

Returning to New Zealand and redefining success through simplicity

Why every leader should commit to doing something hard

Lessons on storytelling, team culture, and customer obsession

Follow Clive Ormerod:

LinkedIn: https://www.linkedin.com/in/cliveormerod/

Stay Connected with Jason & Execs Who Run:

Jason Hunt: LinkedIn | Instagram

Execs Who Run: LinkedIn | Instagram

Website: execswhorun.com

Strava: Join our Strava Group

Support the Show:
If Clive’s story inspired you, follow, rate, and review Execs Who Run on your favourite podcast platform. Share this episode with a friend or leader who’s ready to run toward growth.

Tim Dettmann is on a mission to make Australia healthier—one lift, one run, and one conversation at a time.

In this insightful and inspiring episode, Tim shares how he evolved from rural physio to health business builder, global marathon runner, and thoughtful advocate for equitable exercise access. Whether it’s leadership, fitness, or finding your limits, this episode is full of energy and wisdom.

Key Moments in This Episode:

Sunday trail runs, pacing ultras, and recovery gone wrong

The moment a drunken bet ignited a marathon obsession

Why Tim left elite sport for everyday health impact

Building Kieser from two employees to 26 clinics nationwide

How to lift twice a week and save lives—literally

Volunteering with TriMob and Ocean Heroes

Running 2:43 at Berlin and aiming sub-2:40 in Chicago

The powerful life lesson behind pacing a mate through a 100-mile race

Resilience, leadership, and tofu brains (!)

Resources & Links:

Kieser Australia

TriMob

Ocean Heroes

Follow Tim Dettmann:

LinkedIn

Instagram: @timdettmann (adventure and running updates)

Stay Connected with Jason & Execs Who Run:

Jason Hunt LinkedIn

Execs Who Run LinkedIn

Instagram: @execswhorun

Website: execswhorun.com

Support the Show:
If Tim’s journey inspired you, follow, rate, and review Execs Who Run on your favourite podcast platform—and share this episode with someone aiming to run toward their full potential.

Mia Farrow’s life is the ultimate endurance story—civil war survivor, immigrant, banker, mother, and mountain runner.

From sprinting in her brother’s shoes through war-torn Serbia to conquering Aconcagua’s icy heights, Mia shares how running shaped her resilience and how motherhood deepened her purpose.

Key Moments in This Episode:

Growing up during the Yugoslav Wars and training on rubble tracks

Running as both refuge and rebellion during adolescence

From immigrant to investment banker: breaking into Wall Street

Winning the Everest Marathon and finding home in high altitudes

Juggling motherhood and marathon dreams in a new country

Her solo speed ascent of Aconcagua after just 10 days at altitude

Reclaiming identity through running after an 8-year break

Follow Mia Farrow:

https://www.instagram.com/mia_highaltitude/

https://www.instagram.com/mia_farrow23/

Stay Connected with Jason & Execs Who Run:

Jason Hunt LinkedIn: https://www.linkedin.com/in/jasonzanehunt/

Execs Who Run LinkedIn: https://www.linkedin.com/company/execswhorun

Instagram: @execswhorun

Website: https://execswhorun.com

Support the Show:
If Mia’s journey inspired you, please follow, rate, and review Execs Who Run on your favorite podcast platform—and share this episode with someone chasing their next summit.