My First Million Podcast Summary

Episode: The Man Who Made a Billion Off Blueberries
Hosts: Sam Parr & Shaan Puri (Hubspot Media)
Date: September 12, 2025

Episode Overview

This episode centers on the extraordinary story of John Bragg, a little-known Canadian entrepreneur who quietly built a billion-dollar empire—first transforming the global blueberry industry and then becoming a telecommunications magnate. Sam and Shaan explore Bragg’s unconventional business philosophies, share colorful anecdotes from his career, and zoom out to consider patterns among old-school operators who crossed from blue-collar roots into multi-industry domination. The discussion branches out to broader reflections on business, mindset, legendary business figures, the psychology of elite performance, and the creative process behind iconic work.

Key Discussion Points & Insights

1. The John Bragg Story: From Blueberries to Billions

• Early Entrepreneurship:

  • Grew up on a family farm in Nova Scotia.
  • As a teenager, picked blueberries to pay for college: “His last year of high school, him and four or five other blueberry pickers end up making $4,000 each picking blueberries, which was a lot of money at the time because this guy's very old.” (Sam, 01:00)
  • Realized, “I can pay for college if I just pick blueberries every year.”

• Founding the Blueberry Empire:

  • Weighed several career choices: teacher, family sawmill, or go all-in on blueberries. Chose the path less traveled—building his own blueberry farm.
  • Faced a massive industry glut/crash, forcing him to pivot.
    • Built a packaging/freezing plant not just for himself but for other local farmers, organizing competitors: “He goes to the other blueberry farmers, says...let's put some money in together. And I'm going to build this plant. ...He borrows money from the bank, he gets money from the other farmers, he starts to build this thing. Never no experience, by the way, ...I can do this.” (Sam, 03:06)
  • Early calamities didn’t stop him: devastating frost led to massive underproduction in his factory’s first year. Rather than fold, he took on a contract to manufacture onion rings for another local entrepreneur, keeping the factory afloat.

• Building Oxford Frozen Foods:

  • Oxford Frozen Foods now controls 40–50% of the global blueberry market: “It's like 70 million pounds of blueberries they're making every year.” (Sam, 05:05)
  • Shared technology: freely distributed a cutting-edge blueberry picker to other farmers to raise the industry tide—believed in expanding the “pond.”

• Second Act in Cable & Telecom:

  • Serendipitously bought the cable TV rights for his rural region when no one else showed interest.
  • Despite early losses, grew his cable holdings into Canada’s largest private telecom company by acquiring infrastructure and avoiding the “sexy” parts of the business.
  • “Whereas most TV companies want to do the sexy, fun stuff, they get into original programming...he’s like, yeah, no, yeah, you know, what's king? Fiber." (Sam, 06:30)

2. Patterns Among Old-School Moguls (07:58–11:28)

• Drawing parallels between John Bragg and fellow North American “cowboy” entrepreneurs like Ted Turner, Jim Pattison, and John Catsimatidis: people who leap from one industry to “boring” infrastructure or media.
• The Golden Era of Cable: “...it was sort of like the first version of SaaS business, you know, it was recurring revenue. Huge TAM. Kind of weird and unknown. People weren’t sure what to do.” (Shaun, 10:26)
• Regulatory arbitrage and industry consolidation were recurring patterns.

3. Bragg’s Business "Isms" & Philosophies (13:23–20:17)

• No Reverse Gear:
  “I have no reverse gear.” (Sam, 13:38)
  Bragg didn’t consider quitting even after devastating setbacks.
• Intentionally Overpay:
  “Early on, I intentionally overpaid for acquisitions, and word spread fast. If you want to sell, sell to John Bragg.” (Sam, 14:56)
  Built a reputation for paying fairly—sometimes above market—to secure irreversible strategic assets.
• Collaborative Dominance:
  “We don’t want to have 100% of the industry. That wouldn’t be good politics.” (Sam, 17:04)
• Focus:
  “Focus is absolutely critical. ...The biggest single principle you can have in business.” (Sam, 17:13)
• Play the Long Game:
  “I was this young guy who said, I’m here to play this game for a long, long time.” (Sam, 17:37)
• Cultivating Investors:
  At age 70, distributed $10 million each to executive teams, instructing them to manage investments solely for education: “There was no penalty for losing the money and no bonus for the gains. It was pure education.” (Sam, 19:17)

4. Comparisons to United Fruit/Banana Empire (20:44–24:39)

• Sam and Shaan discuss the United Fruit Company and its founder, Samuel Zemurray: street hustler turned “banana king” who orchestrated coups in Central America to preserve his business advantages.
  • “The book is called The Fish that Ate the Whale, because he was the fish, and he eventually ate the whale.” (Shaun, 22:56)
• Illustrates the once-accepted, sometimes ruthless extremes of early 20th-century entrepreneurship.

5. Mindset, Performance, and the “Pain Cave” (34:50–50:12)

• Sporting Parallels in Business:
  • Tennis, running, and fighting analogies abound—namely about the necessity to sometimes “descend” the mountain, to embrace discomfort, to stay sharp.
  • Greats like marathoner Meb Keflezighi are referenced: “What separates these...the freaks among freaks...it is not physical. It is absolutely mental.” (Shaun, 43:31)
• The Pain Cave:
  • Ultra-athletes use the term for enduring prolonged suffering; Sam applies this to entrepreneurship: “...there’s some. There’s a lot of power in just having, like, a label to put on a thing so that when you’re feeling it, you don’t feel like this is a bad thing, that you don’t panic...” (Sam, 48:00)
• Roller Coaster Metaphor:
  • “...you got in line for the roller coaster, baby...there were going to be ups and downs. Don’t be surprised when they come.” (Sam, 48:54)
• Systems for Dealing with Highs and Lows:
  • Highs and Lows Slack channel; naming and revisiting emotional peaks and valleys to keep perspective.

6. Creative Process & Wisdom from Masters (61:45–68:10)

• Learning from the Craftsmen:
  • Seinfeld’s process: 2 hours of sacred, distraction-free writing daily for 45 years.
  • “There is no writer’s block. There’s lazy, there’s afraid, there’s having too high of expectations. But there’s no writer’s block.” (Seinfeld via Sam, 64:28)
  • Tim Urban’s (Wait But Why) corollary: The difference two hours makes.
• The Wisdom Trap:
  • Shaan’s “rebrand” of motivation as “wisdom”: “Oh, you don’t like motivation? You like wisdom.” (Sam, 54:11)
• Copywriters as Gurus:
  • Deep dives into copywriting legends (Dan Kennedy, Bill Bonner), and the “Darwinian” selection pressures of high-stakes creative fields.

7. Modern Craftsmen: Portnoy, Simmons, and the Joy of Mastery (69:25–77:34)

• Consistent Hand-on Creative Involvement:
  • Portnoy (Barstool), Simmons (Ringer): Both remain embedded in the “craft” even after massive financial success. Simmons, for example, carries his own chair into a colleague’s podcast to talk football—pure enthusiasm for the “game.”
  • “Career goals...a job that’s so fun and so you...you just want to do the thing to the point where you’re just going to carry your chair down the hallway...” (Sam, 74:00)

Notable Quotes & Memorable Moments

• “Early on, I intentionally overpaid for acquisitions, and word spread fast. If you want to sell, sell to John Bragg.”
  — Sam Parr, quoting John Bragg [14:56]

• “I have no reverse gear.” — Sam Parr [13:38]

• “We don’t want to have 100% of the industry. That wouldn’t be good politics.” — Sam Parr, quoting John Bragg [17:04]

• “The biggest single principle you can have in business...they make their first million and they think, now I can succeed in any business, even ones I know nothing about.” — Sam Parr [17:13]

• “If you’re efficient, you’re doing it the wrong way. The right way is the hard way. The show is successful because I micromanaged it.”
  — Jerry Seinfeld via Sam [67:22]

• “Oh, you don’t like motivation? You like wisdom.” — Sam Parr (playfully reframing personal development) [54:11]

• “You got in line for the roller coaster, baby...there were going to be ups and downs. Don’t be surprised when they come.” — Sam Parr [48:54]

• “He looks like an HR manager. Right? Like, he doesn’t look like he’s the most naturally talented guy. And that’s kind of why I love it...he’s just this craftsman. He squeezed everything out of his natural talent.” — Sam Parr, on Seinfeld [68:10]

Important Timestamps

• John Bragg’s Blueberry Beginnings: 00:26–05:15
• Oxford Frozen Foods and Industry Domination: 05:15–07:58
• Telecom & Cable Expansion: 05:40–07:58
• Comparisons to Ted Turner, Jim Pattison, et al.: 07:58–11:28
• Key Bragg Business Philosophies (“Isms”): 13:23–20:17
• United Fruit/Banana King Story: 20:44–24:39
• Performance Mindset & Pain Cave: 34:50–50:12
• Creativity, Copywriting, and Craftsmen: 61:45–68:10
• Simmons, Portnoy, & Creative Longevity: 69:25–77:34

Tone & Takeaways

The episode strikes a playful, curious tone—mixing awe at old-school moguls’ grit, irreverent banter about motivations and personalities, and deep appreciation for craftsmanship and the compounding power of relentless focus. If you’re hungry for tactical wisdom (“pay up for rare assets,” “never lose your focus”), mindset reframes (“the pain cave,” “roll with the roller coaster”), or inspiration on how the greats keep creating over decades, this episode delivers.

For the ambitious builder, creative, or investor: John Bragg’s story is proof you don’t need industry permission, inherited status, or even a well-laid plan—you just need relentless drive, intelligent risk, and the guts to stick with it after the frost hits your fields.