Digital Social Hour — Richmond Dinh: Lost $1,000,000…Then Spent His Last $50K on Tony Robbins | DSH #1661

Host: Sean Kelly
Guest: Richmond Dinh
Date: December 12, 2025

Episode Overview

In this candid and insightful episode, Sean Kelly sits down with Australian entrepreneur and coach Richmond Dinh. Richmond recounts his dramatic journey from losing over a million dollars in risky property investments to investing his last $50,000 in personal development—most notably with Tony Robbins—and ultimately making a massive comeback. The conversation weaves through lessons on purpose, risk, the power of mentorship, adapting to an AI-driven world, and actionable frameworks for entrepreneurship and personal growth.

1. Richmond’s Backstory: From Optometrist to Entrepreneur

• Richmond’s Background: Born and raised in Sydney, Australia, Richmond was raised in a Vietnamese family with high expectations. He originally pursued a career as an optometrist to meet cultural and family pressures.
  • “I grew up in Sydney. I was born there. I’m 42 now.” – Richmond, [01:15]
• On Asian Family Expectations: He discusses the cultural expectation to marry within one’s ethnicity and be a “golden child.”
• The Problem with University System: Richmond highlights the perils of chasing “safe” degrees, especially when supply outpaces demand, resulting in devalued professions.
  • “You pay a couple of hundred thousand for a five year degree only to realize there’s no jobs out there.” – Richmond, [02:07]
• Burning the Boats: Richmond walked away from a ten-year career in optometry, giving up his license to force himself to succeed elsewhere and not allow a fallback option.
  • “You gotta be smart, too…Most people burn their boats 1k from shore, and they can’t swim.” – Richmond, [03:44]

2. Losing It All: The $1 Million Downfall

• Property Boom and Bust: Richmond built a portfolio of 12 properties—not understanding the real purpose of wealth—before losing more than $1 million when the iron ore market collapsed.
  • “I bought three properties that totaled to about 1.4 million. And overnight…they went down to 200,000.” – Richmond, [20:46]
• Chasing Money Without Purpose:
  • “If money does not have a purpose, then there is no purpose for money. Most people chase money, and then when they get it, they don’t know what to do with it.” – Richmond, [19:24]; echoed later at [20:46]
• Identity Crisis: As the “successful kid” in a Vietnamese family, losing everything triggered personal turmoil.

3. The Bounce Back: Investing in Personal Development

• Turning Point: Facing bankruptcy with only $50K left, Richmond decided to spend it all on personal development:
  • Tony Robbins event ($20K)
  • One-on-one mentor ($25K)
  • Life coach ($5K)
  • “What do you do when you got 50k cash that you need to spend before you go bankrupt?...I spent it all on personal development.” – Richmond, [04:56]
• The Value of Mentorship and Community:
  • Through events and coaching, he met others who had bounced back from similar setbacks.
  • “That was the biggest blessing in disguise by spending my last 50k on personal development.” – Richmond, [05:38]
• On Failure: Both Sean and Richmond discuss embracing failure as a necessary precursor to future success.
  • “I think failing is necessary to succeed.” – Richmond, [06:01]

4. AI, Adaptation & The Future of Entrepreneurship

• Personal Branding & AI: Richmond talks about launching Richmond AI, a tool trained on years of his content to serve his coaching clients, and reflects on how AI is transforming industries—from law and dentistry to optometry.
  • “Richmond AI has been a game changer and it’s only going to get better.” – Richmond, [10:51]
• Sean’s Workflow: He uses multiple AI tools (ChatGPT, Perplexity, Claude, Grok, Gemini) to prepare for interviews—showing the importance of leveraging technology.
  • “Each one gives different answers, so I like to have a balanced approach.” – Sean, [12:01]
• The Need for Personal Brand:
  • “Personal branding is going to be really important...If you’re not in the top five or top three, that’s…kind of game.” – Sean and Richmond, [13:48–14:19]

5. The Tiny Challenge Framework: Making Your First Dollar Online

• What Is the Tiny Challenge?
  • One-on-one, five-day challenge model for coaches/creators to validate and sell their first offer.
  • Removes tech obstacles, audience size limitations, and fear of selling to a group.
  • “A tiny challenge is a challenge done one on one with you and another person. Five days, five calls, one on one…Best way to make your first dollar online.” – Richmond, [15:06]
• Why One-on-One First?
  • Higher conversion, deep feedback, clarity on messaging and avatar.
  • “The average conversion is one in three. If it’s a thousand dollar offer, that’s the first thousand dollars online.” – Richmond, [16:37]
• Free vs. Paid Challenges:
  • For beginners, run it free to build trust and offer; for established brands, charge upfront.
  • “All of our students who do a tiny challenge, they do it for free. And at the end, they present a 2, 3, 4, $5,000 offer. And then the person says yes, because reciprocity is so high.” – Richmond, [39:10]

Timestamped Example:

• [14:48]: Richmond describes Russell Brunson adopting the Tiny Challenge and immediately making $200K with it.

6. Pricing, Offers, and Scaling

• Richmond’s Offer Structure:
  • Front-end $1,200 offer (reinvested into ads)
  • Back-end $30K group coaching (with one-on-one/“shadow seat” upsells)
  • $100K+ selective in-person experiences
  • “I’ve got my 100k clients sitting here...there’s no one on one.” – Richmond, [24:49]
• Selling Outcomes, Not Time: Inspired by Myron Golden’s philosophy.
  • “Once you realize you’re not selling your time, you’re selling outcomes, that’s when you can no longer trade time for money.” – Richmond, [25:16]

7. Shadow Seats & Leveraging Access

• The Shadow Seat Model: Richmond pays to shadow high performers (like Andy Elliott at $45K/day) and then sells “shadow seats” to his clients for $1K each, making the investment profitable and scalable.
  • “I sold 51 shadow seats for a grand each…so I got paid to get one-on-one coaching.” – Richmond, [42:43]
• Advice for Entrepreneurs: Turn every learning opportunity into a group offering if you have an audience.

8. The Power of Community & Proximity

• Choosing Who You Spend Time With:
  • “You are the average of who you spend time with. If you’re the most popular in your group, you are in the wrong group. You need to be number five.” – Richmond, [45:17]
  • Youth should seek out groups where they’re not the top achiever; value comes from being the one who is most hungry and willing.
  • “Never sell yourself short on your own energy. Even if you haven’t got the physical, tangible track record.” – Richmond, [45:59]

9. Miscellaneous Notable Topics

• Focus, Pain, and Mindset: Richmond’s experience with Tony Robbins “fire walk”—pain is often dictated by where you place your focus.
  • “Pain is only painful when you’re focusing on the pain…if you’ve got something else you’re obsessing about…the pain becomes irrelevant.” – Richmond, [08:53]
• Global Markets & Currency: Discuss currency arbitrage, international business, cost of living differences, and the impact of the US dollar versus AUD.
  • “When we charge a 30k program. 30k US, we’re actually getting 45.” – Richmond, [36:34]
• Diet & Fitness: Brief tangent on fitness routines and diet, leading up to Richmond training for a gym session with Andy Elliott.
  • “In eight weeks, you got a four pack…I was just on ketosis.” – Richmond, [44:13]
• Political/Economic Commentary: Brief insights into American and Australian economics/politics, parodying home ownership myths, and how US politics ripple globally.

10. Actionable Steps for Listeners

• Starting a Tiny Challenge: DM your five followers, offer a free 5-day challenge to solve a specific problem, and present an offer at the end.
  • “Easiest way to get started. Even if you’ve got five followers…” – Richmond, [37:36]
• Leveraging Your Network & Curiosity: Pay for proximity to greatness, then share/monetize access with your community.

Memorable Quotes & Moments

• “If money does not have a purpose, then there is no purpose for money.” – Richmond, [19:24], [20:46]
• “Failing is necessary to succeed… obviously I don’t want to go through that again.” – Richmond, [06:01]
• “You need to model beliefs, not model behavior.” – Richmond, [29:10]
• “Never sell yourself short on your own energy. Even if you haven’t got the physical, tangible track record.” – Richmond, [45:59]
• “If you’re the most popular in your group, you’re in the wrong group. You need to be the poorest kid in your top five.” – Richmond, [45:17]

Key Timestamps

• 00:00 – 03:01: Richmond’s upbringing, optometry career, and early life lessons
• 04:06 – 05:38: Bankruptcy, spending last $50K on personal development, Tony Robbins impact
• 10:51 – 14:20: AI, personal branding, and the future of work
• 15:06 – 17:16: Tiny Challenge Framework: how beginners can make their first dollar online
• 24:05 – 26:14: Pricing models, outcomes vs. time, group vs. 1:1 coaching, Myron Golden’s influence
• 37:36 – 39:40: Step-by-step on launching the Tiny Challenge yourself
• 42:12 – 43:44: Shadow seat model & creative ways to monetize personal development investments
• 45:17 – 46:14: Advice on proximity and group selection for growth

Closing Takeaways

Richmond Dinh’s story is a masterclass in resilience, leveraging adversity, and finding purpose beyond simply “chasing money.” His frameworks for starting and scaling coaching businesses, along with insights on branding, AI, and the evolving landscape of entrepreneurship, are deeply actionable. The greatest advice: always invest in yourself, foster proximity to greatness, and remember—the shortest way is often the right way, done with purpose.

Connect with Richmond and learn about the Tiny Challenge via the links below this episode.