Digital Social Hour — DSH #1538

Guest: Jon Andersen
Host: Sean Kelly
Date: September 19, 2025

Episode Overview

This episode features a candid, wide-ranging conversation between host Sean Kelly and Jon Andersen, a multi-hyphenate entrepreneur, pro-strongman, wrestler, bodybuilder, addiction survivor, and performance coach. Jon shares how early struggles with learning disabilities, childhood obesity, and later addiction became the fuel for a relentless drive and diversified 7-figure entrepreneurial success. The discussion covers his unconventional path—building and selling businesses, overcoming personal demons, winning in sports and business, and empowering others through mindset coaching.

Key Discussion Points & Insights

1. Formative Struggles: Learning Disabilities and Obesity

• Jon’s early years: Struggled with a learning disability, was placed in special classes, and faced bullying for being overweight.
  • “Because of that, I was kind of easy kill for, you know, for made fun of. And so what I did was I ran to food for comfort.” — Jon Andersen (04:01)
• Isolation from his peers created a drive to work twice as hard just to feel 'normal,' later translating to a powerful work ethic and problem-solving ability.

2. Building First Businesses — Lessons Before the Internet

• Jon’s first successful business was a painting company he started in college, later built up and sold to a corporate buyer burnt out from the 9-to-5 grind.
  • “When I knew that I could do it, I didn't want to have that company. I wasn't. Didn't want to be a painter by any means, but I knew that I could start the company, build it and sell it, and that's what I did.” (01:11)
• He also launched a meal prep business “two decades too soon,” underscoring the risk of being “too early” for the market. (02:15–02:50)

3. From Physical Struggle to Physical Confidence

• Weight lifting became Jon’s outlet and identity after seeing Arnold Schwarzenegger in Conan the Barbarian.
  • “Something inside me changed. It was like I got bit by the iron bug and I never looked back.” (09:06)
• Weight room success led to a newfound self-assurance and clear sense of purpose.

4. From Athletics to Serial Entrepreneurship

• Used proceeds from his business exit to fund his strongman journey; quickly gained sponsorships and entry into pro-strongman circuits.
  • “I had a Super bowl commercial, I had an agent. So I mean I was living the dream, dude.” (12:23)
• Simultaneously built a real estate flipping business, capitalizing on connections from his painting days.

5. Shifting Career Paths—Learning from Setbacks

• Back injury pushed Jon out of strongman, pivoted to professional wrestling (with a faked résumé, then learning on the job).
  • “He completely fraudulated a resume, said that I knew what I was doing...next thing you know, I get a deal in Japan. My like 7th ever wrestling match was a pay per view in Sapporo, Japan.” (14:13)
• After seven years wrestling, transitioned to pro bodybuilding—in his forties, defying doubters yet again.
  • “You're 42, you can't do that. I say, you might be right, but I'm gonna try anyway. I've been told I couldn't my whole life.” (14:55)

6. Cross-Disciplinary Skills: Mindset as the Common Denominator

• Emphasizes that discipline, resilience, and skill-building translate across all domains—business, body, mind, and relationships.
  • “If a man trained his brain like he trained his chest, he could have whatever he wants.” (16:29)
• His coaching now centers on this philosophy: action, mindset, and habits are more important than shortcuts.

7. The Dark Side — Addiction and Recovery

• Openly recounts his battles with binge eating and sugar addiction, which later led to painkiller addiction post-injury.
  • “It was like once a fat kid, always a fat kid. A sugar addict. You're always an addict. Whatever you're addicted to...Recovery is management.” (22:31)
• Details how prescribed opioids spiraled into dependency.
  • “It starts off, you get hurt...pretty soon the pain's gone. Now you're using it so you don't feel sick, and now you're hooked.” (26:39)
• Offers support to listeners struggling with addiction: “If you have a problem with this, I am an open book. Come on my social media, I'm happy to talk to you about it.” (27:16)

8. Judgment, Fear, and the Mindset of Change

• Many clients approach him knowing what they want, but paralyzed by fear of judgment.
  • “The biggest thing is, is they know what they want, but they're deathly afraid of what people are going to say.” (17:26)
• Jon encourages embracing failure and tuning out negative societal programming.
  • “Successful people understand that...failure is a part of success. The people that are caught in the matrix...don't understand that; that's why they're stuck.” (17:05)
  • “Arnold Schwarzenegger has a saying that I love. He says, break the rules, don't break the laws...but the rules of society, you don't have to follow those.” (19:19)

9. Shortcuts vs. Sustainable Change

• Discussed the perils of shortcut culture, notably weight loss drugs like Ozempic.
  • “If you don't change how you live, if you don't change how you think, you'll be right back there.” (31:51)
  • “What are you filling those time slots with?...Are you filling your time slots with trying to find shortcuts? Because we all know a shortcut…They backfire doesn't work long term.” (32:25–33:05)

10. The Power of Identity and Neuroplasticity

• Highlights habit-building, repetition (“24-hour loop”), and leveraging personal strengths—even traits once called disabilities (OCD, ADHD, dyslexia).
  • “You only really are going to call it a disability if you allowed to call it become a disability. My disability is an ocd. This is strength.” (34:15)
• “If most men trained their brain like it did their chest, they'd have whatever they want, you know?” (41:23)

11. Routine, Discipline, and Self-Optimization

• Jon maintains extreme discipline: 8:00 p.m. bedtime, up at 2:30–3:00 a.m., starts each day with gratitude and focused improvement.
  • “I go to bed at 8:00 clock period.” (36:04)
  • “If I'm not getting better, my business is not getting better.” (37:10)
• Men especially, he argues, need to invest in themselves first before expecting business or external success.

12. Comfort is the Enemy of Progress

• Our brains are programmed to seek comfort, but in today’s world that often leads to stagnation.
  • “Comfort in today's world keeps you in a job you don't want to be in...If I'm comfortable, I get...I start getting weird.” (46:00, 46:43)
• Encourages seeking discomfort as the path to growth: “Me being uncomfortable is what made me comfortable.” (46:26)

13. Defining Success and Creating a Life You Love

• After setbacks (losing everything in 2008), Jon redefined success not by money alone, but by freedom, impact, and growth:
  • “At that point, I made a decision in my life. I will never do something to earn a dollar. I love it. Probably one of the best changes my life ever.” (48:36)
• Money flows as a byproduct of energetic alignment and loving what you do; everyone must define success in their own terms.
  • “My definition of success is to be financially free, constantly creating changing lives, you know, and constantly creating the big part.” (49:53)

Notable Quotes & Memorable Moments

• “If a man trained his brain like he trained his chest, he could have whatever he wants.” — Jon Andersen (16:29)
• “Failure is a part of success. And successful people understand that. The people that are caught in the matrix...don't understand that, that's why they're stuck.” — Jon (17:05)
• “You're always an addict. Whatever you're addicted to, you're either someone's in the addict or not. You never really recover. You manage, so to speak. Recovery is management.” — Jon (22:31)
• “I was good at making money that I really didn't love, but...just a half a step above the guy that was going to a job he didn't really like. But now...I get goosebumps and...warmth of my chest when I do my job.” — Jon (48:36)
• “You can't make someone change. Someone has to want to change. And all I need is for someone to have the character enough to take that first step. Because I know they take that first step, that little bit of momentum, I can get them to see the light. And once they see the light, they never look back.” — Jon (45:17-45:35)

Important Timestamps

• [01:11] — First business success: Painting company origins and exit
• [04:00] — Childhood struggles with obesity and learning disabilities
• [09:06] — Discovering weightlifting, growth in confidence
• [11:43] — Transition to pro strongman and entrepreneurship
• [13:03] — Pivoting from strongman to pro wrestling to bodybuilding (42 years old)
• [16:29] — Mindset parallel: Training your brain like your chest
• [17:26] — Central obstacle for young men: Fear of judgment
• [22:31] — Struggles with sugar addiction and substance abuse
• [26:39] — Inside painkiller addiction, warnings for listeners
• [31:51] — On weight loss drugs and the trap of shortcuts
• [36:04] — Discipline: 8 pm bedtime, early mornings
• [41:23] — Neuroplasticity, thought training, and identity
• [46:26] — On comfort being a danger to ambition
• [48:36] — Redefining success after failure
• [51:26] — Where to find Jon (Instagram: @thejonanderson)

Closing Resources

Find Jon Andersen:
On Instagram: @thejonanderson
Jon is open to DMs, offers support on addiction, coaching, and mentorship.

Concise Takeaway

Jon Andersen’s story is a testament to transformation—turning hardship into resilience, addiction into mastery, and doubt into relentless action. The episode is packed with raw advice on overcoming internal and external barriers, building mental and physical resilience, and living life on your terms. No matter your struggles, Jon insists, with mindset, discipline, and purposeful discomfort, a remarkable life is possible.