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Episode 260

Why Comfort Kills with Joe de Sena | Win the Day
October 28, 2025
Joe De Sena is a New York Times bestselling author, ultra-endurance athlete, and founder of Spartan endurance events and programs.
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In this episode of Win the Day:

“Even if you’re on the right track, you’ll get run over if you just sit there.” — Will Rogers

Joe De Sena is a New York Times bestselling author, fitness icon, and the founder of Spartan—a global movement that’s transformed more than 10 million lives through its world-renowned endurance events and lifestyle programs.

After building a multimillion-dollar pool and construction business in college, and launching a Wall Street trading firm, Joe left it all behind to pursue a more meaningful mission: to get 100 million people off the couch. What started as a few races in Vermont has exploded into a global fitness phenomenon, with over one million participants across 40+ countries every year.

Joe has personally completed more than 50 ultra-events and once competed in 14 Ironmans in a single year. Through his books, keynotes, and SpartanX Leadership Forums, he now trains others to build mental toughness, embrace discomfort, and live with purpose.

In this episode:
• How to strengthen your mindset through physical challenges.
• The daily discipline behind elite performance.
• Why modern life makes us soft — and what to do about it.
• How to build a healthy, loving, and resilient family.

Let’s WIN THE DAY with Joe de Sena!

Timestamps

00:00 Who is Joe De Sena

1:47 Interview starts

3:22 The decision to start Spartan (purpose vs corporate world)

5:22 Joe De Sena’s superpower

7:48 Develop the ability to inspire others

8:41 Why comfort kills (and the problem with laziness)

11:11 Almost going bankrupt

13:30 How Spartan saves lives

16:28 The #1 way to get out of depression

19:10 Your mental health depends on the people around you

20:45 The hardest habit for people to change

22:11 Why you’re failing with your health and fitness goals

23:22 How Joe De Sena sets (and achieves) goals

25:20 Are material possessions making you weak?

27:38 How to become more resilient

29:21 The toughest ultra events on the planet

31:22 How to get through your most challenging moments

32:46 How to know when enough is enough (i.e. you’re pushing too hard)

34:09 Earn your reward

34:46 Joe De Sena parenting approach (always take the hard way with your kids)

35:42 Are you putting too much pressure on your kids?

39:03 Celebrate hard work with your kids

39:50 What sports to put your kids in

40:49 Focus on hard work (not winning or losing)

41:58 Joe De Sena family values

43:30 How to make your kids more resilient

45:23 Why parents need to model healthy behavior

46:24 How to stop a bad day from coming into the home

46:55 Affirmation

47:40 Rocket Round

Resources / links mentioned:

🎯 Download your FREE Win the Day action plan

⚡ Joe de Sena website

📷 Joe de Sena Instagram

📝 Joe de Sena Facebook

🌎 Joe de Sena X

📱 Joe de Sena TikTok

♾️ Joe de Sena LinkedIn

📚 ‘The Spartan Way: Eat Better. Train Better. Think Better. Be Better.’ by Joe de Sena

🎤 TEDx Talk ‘Burpees and the Art of Pool Maintenance’ by Joe de Sena

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📝 Win the Day newsletter [weekly LinkedIn exclusive]

Inspiring quotes in this episode:
  • "I always had an ability to inspire people around me to do things they didn't want to do." — Joe de Sena
  • "I push myself and others to just go a little further. A couple extra steps, one more rep." — Joe de Sena
  • "If you’re feeling depressed, the number one thing you can do is move." — Joe de Sena
  • "There's nothing in life that you can't walk off." — Joe de Sena
  • "Working out is something you commit to doing every day—forever." — Joe de Sena
  • "The hardest thing for people to do is to be consistent." — Joe de Sena
  • "When you're not feeling it, which is going to be often, just lie to yourself so you can get started." — Joe de Sena
  • "As short as life is, it's a long road. And you just got to make it to the next telephone pole." — Joe de Sena
  • "You're going to have choices between the hard way or the easy way. Always take the hard way with the kids. The kids kicking and screaming in the airplane, you can hand them a phone, a device to just have them zone out. Don't do it. Deal with the kicking and screaming. Work through it. Play cards with them. Somehow get them tired, walk back and forth to the bathroom 500 times, do burpees in the back of the plane. Come up with something but don't take the easy way. And that's been our philosophy in the house. We just don't take the easy way." — Joe de Sena
  • "Hard work is the main thing we're focused on in our family." — Joe de Sena
  • "We're not trying to train kids to be up at noon. The whole world wakes up early to get work done." — Joe de Sena
  • "Whatever you want your kid to be, that's the way you should act." — Joe de Sena
  • “Earn your reward.” — Joe de Sena
  • "Sweat before breakfast." — Joe de Sena
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