Trading Secrets Podcast – Episode 259

Guest: Harry Jowsey
Host: Jason Tartick
Date: October 20, 2025
Title: Harry Jowsey: From reality TV to scripted, how Netflix powerhouse has expanded his career on screen, continuing to redefine the rules, and the core values that keep him grounded

Overview

This episode explores the remarkable career trajectory of Harry Jowsey, from scrappy reality TV hopeful to a powerful force across Netflix’s unscripted and scripted projects. Host Jason Tartick welcomes Harry back for a candid conversation about personal growth, financial realities behind entertainment, entrepreneurial ventures, and the mindset Harry credits with his unique ability to navigate fame, criticism, and creative opportunities. The episode offers a masterclass for aspiring creatives and entrepreneurs, loaded with “trading secrets” on money, media, authenticity, and reinvention.

Main Theme

How Harry Jowsey has continued to rewrite the rules in reality and scripted TV, expanded his entrepreneurial footprint, and stayed authentic while navigating money, fame, and personal growth.

Key Discussion Points & Insights

1. Evolution and Reflecting on Early Ambitions

• Humble Beginnings & Hustle:

  • Harry reflects on sending hundreds of reality TV applications and even lying on resumes just to get a shot.

    "I would wake up and submit hundreds of applications. I would lie on resumes... I knew I was born for reality TV."
    (01:27)

• Early Financial Goals:

  • In 2021, Harry described having $3,000 in his bank account, aiming to be a millionaire by 23, and later striving for $10M a year.

    "You said, ‘I talked to Logan Paul and I need to find a way to make $10 million a year.’"
    (01:27)

• On Changing Mindsets:

  • Harry now sees those goals as short-sighted, shifting focus from immediate gains to cultivating opportunities for future growth.

    "The short-sightedness for me was being focused on the dollar amount... whereas now, it’s planting seeds for years ahead."
    (04:55)

2. Fame, Insecurity, and the Trap of Validation

• On Spending to Impress:

  • Discussed paying $15,000/month for an apartment as a validation of success, later realizing it was driven by insecurity and the fear of irrelevance.

    "There's always this constant like trying to validate my success... instead of just being so afraid to be irrelevant."
    (03:52)

• Changing Approach to Money:

  • Harry admits to lessons learned, now focusing more on personal growth and less on outward signs of success.

3. Redefining the Rules in Entertainment

• Crossing Reality to Scripted:

  • Traditionally considered “impossible,” Harry is moving between reality TV, acting roles (The Wrong Paris, Billy Knight with Al Pacino, Horrified), and hosting his own Netflix series (“Let’s Marry Harry”).
  • Sees inspiration in Kevin Hart’s strategy to “get so big no one could say no to him.”

    "People said, ‘Oh, you could never act. You can never do this.’ I’m like, ‘OK... They’ll never take you serious.’ I’m like, ‘Well, I don’t take myself seriously anyway, so we’re good.’"
    (07:03)

• Authenticity as Power:

  • Harry’s imperfection and candidness help him evade the “cancellation” typical in reality TV.

    "If I make a mistake and get a ton of hate... I won’t make that mistake again. It makes me a better off person because I care less."
    (09:32)

4. Strategies for Career Longevity & Personal Branding

• Staying Relevant (or Not on Purpose):

  • Contrasts earlier desperation for relevance with current willingness to "go quiet" to refresh his brand.

    "Now I understand... you have to go quiet for a little bit and be missed to come back and be really appreciated."
    (03:52)

• On Networking with Netflix:

  • Progression came not from waiting for opportunities but consistently pitching ideas, getting facetime with executives, and forming genuine relationships.

    "I would think of an idea, even if it’s stupid, just to force a meeting, just to be in front of them."
    (13:01)

• Planting Seeds:

  • Harry now measures his year by ‘how many seeds can I plant’ instead of quick hits.

5. Behind "Let's Marry Harry"

• Manifesting & Creation:

  • Harry admits to faking being “The Bachelor” online long before being cast and now gets to headline his own, Bachelor-esque dating show on Netflix.

    "I was manifesting being the Bachelor. I would lie about it. I’d make a fake [post]… and now I feel like I can recreate The Bachelor."
    (16:37)

• Family & Support System:

  • Close friends and family will help pick his match on the show for authenticity.

• Preparing for Marriage On TV:

  • Harry is actively working on himself – reading therapy/self-help books, therapy, and practicing meditation – to ensure he's ready for commitment, addressing issues like directness in relationships.

    "Every day I’m trying to finish a book... I’m seeing my therapist more now than ever to figure out what has happened in my childhood that makes me pull away or not."
    (22:00)

6. Money, Negotiations, and Opportunity Cost

• Finances of Reality TV vs Brand Deals:

  • Largest income is from independent brand deals, but being on Netflix amplifies his marketability.

    "I still make more money from brand deals... but I couldn’t get the brand deals without the show."
    (27:03)

• Highest Earning Brand Deal:

  • Tinder partnership, worth over $500K.

    “I think it was over half a ticket.” (55:00)

• Sacrifices and Opportunity Cost:

  • There are financial tradeoffs for doing certain shows (e.g., losing out on $200K in potential brand deals due to filming).

    “I spend more on wardrobe or... there could be a month where there’s 200k in brand deals. Can’t do it because I’m filming... Opportunity cost.”
    (26:14)

7. Scripted vs. Reality: Pathways & Pay

• On Breaking In:
  • Started with acting coaches, dozens if not hundreds of auditions, and acknowledges the challenges of transitioning from playing himself to playing characters.

    "You just have to put in the work and be consistent... There's less traffic in your own lane. So stay in it."
    (59:50)

• Scripted Pay Lower Initially:
  • “Scripted, it’s not good. ... I think a lot of people freak out about not making a ton of money off the jump."

    “First show, $250 a week... Just doing it for the love of the game."
    (38:01)

8. Dealing with Hate & Social Media Strategy

• Handling Criticism:
  • Has built resilience, believing hate ‘never comes from above.’

    “No one who’s doing better than you is going to hate and punch down.”
    (10:11)

• Monetizing Social Media:
  • Instagram and Snapchat are his top-earning platforms. Utilizes scheduling and high-frequency posts, including posting 500 times in one day for a $30K+ payout.

    "I think, obviously Instagram I make the most. Obviously Snapchat makes a ton of money... when I was doing Dance with the Stars, I was posting so much... 500 times in a day."
    (53:00)

9. Entrepreneurial Projects & Future Vision

• Philanthropy and Mission:
  • Harry’s venture, PASH, has a philanthropic mission inspired by personal losses. He opens up about losing friends to suicide and wanting his career to bring laughter and hope.

    "My goal has always been: let’s give people their 40 minutes a week so they can laugh... I do what I love by making my friends laugh."
    (58:01)

• Dreams of Producing & Giving Back:
  • Wants to pivot to producing feel-good reality shows and building a charity focused on mental health, especially in Australia and New Zealand.

Notable Quotes & Memorable Moments

• On the Trap of Fame:

  "I thought I was the man, the king of the world. Like, buying all these watches, doing all this stuff. It was ridiculous. It was a crazy time."
  (02:31, Harry)

• On Authenticity & Resilience:

  "When you are true to your authentic self, the expectation is that you are your authentic self."
  (08:28, Host)

• On Networking and Opportunity:

  "I’d think of an idea—just to force a meeting [with Netflix], just to be in front of them... at least you’re always front of mind."
  (13:01, Harry)

• On Financial Mindset Shift:

  "I think at that time I was obsessed with the number. Now, I'm obsessed with the energy or the feeling. That's massive growth."
  (47:24, Harry)

• Harry's ‘Trading Secret’:

  "When it comes to life and social media...just have fun and don't care as much as you feel like you should. There's less traffic in your own lane. So stay in it. One video. One thing will change everything."
  (59:50, Harry)

• On Using Fame for Good/Mission Statement:

  "The goal has always been, let’s give people their 40 minutes a week so they can laugh at something stupid I’m doing... I get to do what I love by making my friends laugh."
  (58:01, Harry)

Timestamps for Key Segments

• 00:00 – 02:31: Recap of Harry’s 2021 goals, early career hustle
• 02:31 – 05:54: Lessons in money, validation, and evolving perspective
• 07:03 – 11:13: Authenticity, redefining industry “rules”, handling hate
• 12:52 – 14:57: Building brand with Netflix, strategies for career longevity
• 16:27 – 18:20: How “Let’s Marry Harry” came together, family involvement
• 22:00 – 23:44: Preparation for love, therapy, personal growth
• 25:18 – 27:16: Financial realities, brand deals vs. show pay
• 28:18 – 32:36: State of reality TV industry, transition to scripted acting
• 35:22 – 36:55: Acting: Table reads, intimacy scenes, behind the scenes of “Horrified”
• 38:15 – 42:26: Working with Al Pacino, producing, ambitions for future
• 51:57 – 53:10: Social media: strategy, highest earning platforms
• 54:52 – 56:12: Overspending, biggest brand deal (Tinder: $500k+)
• 58:01 – 59:50: Philanthropy, giving back, mental health mission
• 59:50 – 60:45: Harry’s “Trading Secret” – have fun, stay in your lane, anything can change with one opportunity

Final Takeaways & Tone

Rich in motivation and candor, this episode is both entertaining and highly instructive. Harry Jowsey’s journey is a testament to the power of authenticity, relentless self-improvement, and joyfully breaking the mold. The conversation weaves advice on money, career, and fame with big-hearted insights about personal growth, friendship, and impact.

Harry’s tone remains self-deprecating, light, and honest, while Jason provides strategic, sometimes hard-hitting questions, always circling back to actionable insights for listeners.

Where to Find Harry & What’s Next

• Let’s Marry Harry – Premiering 2026, Netflix
• The Wrong Paris – Scripted Netflix release, Fall 2025
• Billy Knight (opposite Al Pacino) – Coming soon
• Podcast: Boyfriend Material – under Alex Cooper’s Unwell Network

Follow him at: @HarryJowsey everywhere

Harry’s Trading Secret (59:50)

"When it comes to life and social media... just have fun and don't care as much as you feel like you should. There's less traffic in your own lane. So stay in it. One thing will change everything."

Summary for New Listeners:
Whether you’re a creative, entrepreneur, or simply love great behind-the-scenes stories, Harry Jowsey’s journey offers permission to dream bigger, reinvent often, and always build a life that’s true to yourself. He proves the value of showing up—hustling, owning mistakes, and embracing the wild ride with laughter and heart.

End of summary.