The Mello Millionaire with Tommy Mello

Episode: Why Most Deals Fail with Shark Tank's Kevin O'Leary
Release Date: November 14, 2025
Guest: Kevin O'Leary, investor, entrepreneur, and "Mr. Wonderful" of Shark Tank
Host: Harley (Mello Studios)

Episode Overview

This episode features a candid and wide-ranging conversation between hosts Tommy and Harley and world-renowned investor Kevin O’Leary. The discussion centers around the realities of entrepreneurial success, why most business deals fail, and how founders and investors need to adapt to win in today’s dynamic landscape. With stories from his own career, lessons from Shark Tank, and straight talk about leadership, execution, brand building, and personal development, O’Leary delivers actionable advice for founders, operators, and would-be millionaires.

Key Discussion Points and Insights

1. Entrepreneurship: The Journey, Not the Destination

• On supporting entrepreneurs:
  O'Leary shares, "Entrepreneurship is not a destination, it's a journey and we're all in it together... if you are going to do it, you want to talk to other entrepreneurs, you want to share ideas, you want to help entrepreneurs not make the same mistakes that I made." [02:06]
• Only about a third of the population is really suited for it, he notes—it's hard, and it isn’t for everyone.

2. The Resilience of Home Services and the Changing Business Landscape

• On the home service industry:
  "It's probably one of the best times ever to be in it... it's never going to be replaced by AI or any of this disruption stuff. It's the core of most people's net worth is where they live and they care about it," O’Leary says. [02:55]
• Host Harley notes that multiples on businesses in the sector have rocketed up, backed by recurring revenue and a market shift toward valuing stability.

3. Investment Priorities: Recurring Revenue & Risk Management

• O’Leary’s main investment filters:
  • "How do I get my money back, first of all? Secondly, how stable is the recurring revenue?" [03:53]
  • The safety of subscriptions, reoccurring revenue, and executional skill matter more than hype or shiny forecasts.
  • “That’s why [the market] went from a 7 to a 20 [multiple]... the market decided that because that’s what the market wants.” [04:43]

4. Adapting to Technological Change and Not Betting Against America

• O’Leary is optimistic about technology, debunking doom scenarios:
  • "I don't believe in predicting doom in the American economy. That's never worked... We're good at doing stuff that makes it easier to live and more productive." [05:24]
  • Technological change always brings disruption, but the economy expands and roles evolve, as with the car replacing horse-drawn buggies.

5. Private Equity: What Most Get Wrong and the Importance of Founders

• PE firms that “treat [companies] like a cog, a wheel” and cut founders out almost always fail.
• "The analysts that do that work have never actually run a business... Until you've made payroll on a Wednesday night, you don't know what it's like." [08:06]
• Modern PE is shifting: "They're starting to realize they got to partner with the founder... You give them incentives to actually work as hard as they did when they controlled it." [08:50]

6. Tech-Enabled Productivity for Entrepreneurs

• O’Leary describes how he uses advanced tech (like a $6,000 Bluetooth IFB from Starkey) to handle communications in real-time and improve productivity. [09:34]
• Host Harley emphasizes using tools like ChatGPT5 and AI-driven platforms for both efficiency and marketing ROI.
• O’Leary: "We all have subscription services... We'll do three versions [of content], put it through ChatGPT... Then we test it... Boom, it worked better. But testing works." [10:50]

7. Key KPIs and Talent Acquisition

• Harley’s universal business dashboard: Booking rate, conversion rate, average ticket, and cost per lead—metrics that transcend industries. [12:08]
• On finding and retaining great talent, O’Leary prefers a portfolio strategy, keeping companies under a holding company umbrella, and describes the balancing act between disaster and euphoria that comes with managing many businesses at once. [13:14]

8. Storytelling & Humanizing Your Brand

• "Quit making ads transactional. Tell stories... let people get to know you." [14:36]
• O’Leary agrees, referencing his investment in Wicked Good Cupcakes: “Cupcakes are a total commodity... but they turned it into a massive business and no one saw it coming.” [15:10]
• Authentic stories and founder transparency drive connection and loyalty: “If people want to be part of that community and that culture and that vision, they’re going to become your customer. Those are very valuable.” [15:09]

9. Mentors, Moms, and Millionaire Mindsets

• Both men attribute key values and lessons to their mothers:
  • O’Leary’s mother told him, “Always tell the truth. And you’ll never have to remember what you said.” [16:21]
• On advice: “If I could treat people like mom, they keep coming back.” [16:15]
• On hiring: O’Leary now favors bringing in new team members as higher-paid contractors for six months before fully hiring, to ensure fit for both parties. [18:38]

10. Execution Over Ideas

• "Great ideas are diamond dust, and executional skills are impossible to find... I like to see people come up through sales because they understand how hard it is at the beginning of the month to be zero." [19:51]
• You can share the playbook, but “less than 1 out of 10 people could do the same thing.” [20:09]

11. Lessons from Steve Jobs and Elon Musk

• O’Leary describes Jobs as brilliant and brutally focused:
  “He was an asshole, 100%... He also taught me about the concept of signal to noise ratio—get three things done every day, and block the rest out.” [20:40, 20:56]
• Musk is “100% signal” as well, hyper-focused and “wildly successful in so many sectors... The rest is all bs." [29:20]
• Ownership of mistakes is a must. If someone blames the market or others for failure, O’Leary won’t invest. [30:24]

12. Equity Incentives and Building Teams

• O’Leary: “Everybody that's important to the business should have some sweat equity in it.” [23:37]
• In his model, both he and the founding operator get diluted equally as new key hires join—ensuring selectivity and shared outcomes.

13. Branding: Customer Service as Brand Building

• "Brand building is now storytelling... What happens is if you are a great provider, the customers start talking about your brand, your company, your service. They're the best ambassadors..." [24:03]
• “You should spend a lot of time taking care of unhappy customers and they become a huge asset to you.” [24:53]
• Order of importance: “Customer, customer, customer, then employees, and then shareholders, in that order.” [25:38]

Notable Quotes & Memorable Moments

• On Listening:
  “When you listen, you get more power. I'm happy to just listen. And it's very powerful. It works immensely. That's one thing I wish I'd learned in my 20s because I talked too much back then, but now I don't. I'm very careful. I just listen.” — Kevin O’Leary [00:00, 26:06]

• On Truth in Business:
  “The great thing about telling the truth is you never have to remember what you said.” — Kevin O’Leary [00:23]

• On PE Mistakes:
  “Until you've actually made payroll on a Wednesday night, you don't know what it's like and how hard it is to run a business... rarely works out.” — Kevin O’Leary [08:06]

• On Execution vs. Ideas:
  “Great ideas are diamond dust, and executional skills are impossible to find. Great people have them.” — Kevin O’Leary [19:51]

• On the Role of Technology:
  “You should use every tool that you can afford to advance productivity, both personally and in your business, because your competitor definitely is.” — Kevin O’Leary [09:36]

• On Founder-Led Success:
  “Never get rid of the founder. Never get rid of the founder.” — Host Harley [07:46]

• On Brand-building:
  “Unhappy customers are very valuable because they give you an opportunity to make them happy again.” — Kevin O’Leary [24:46]

Timestamps for Major Segments

• [00:00] — Kevin O’Leary on the power of listening
• [02:06] — Why O'Leary loves working with entrepreneurs
• [02:55] — The enduring value of home services
• [03:53] — What O'Leary looks for before investing
• [05:24] — Not betting against American innovation
• [08:06] — Why deals fail in Private Equity (PE) and the necessity of founder retention
• [09:36] — Leveraging advanced tech for productivity
• [10:50] — AI and data-driven marketing
• [12:08] — Key business metrics (KPIs)
• [13:14] — The “portfolio strategy” for entrepreneurs
• [14:36] — Ads that tell stories, not just make transactions
• [16:21] — Lessons from mothers; always tell the truth
• [18:38] — O’Leary’s new hiring strategy: contractors first
• [19:51] — Why sharing the playbook isn’t enough
• [20:56] — Steve Jobs, signal to noise, and productivity
• [23:37] — Equity incentive models
• [24:03] — Building a brand through honesty, community, and customer obsession
• [25:54] — Three questions: best advice, millionaire habit, and what O’Leary would do with $10M
• [29:20] — Role models: Steve Jobs, Elon Musk, and the importance of accountability
• [31:14] — Book recommendation: Keith Richards’ autobiography
• [32:08] — Final message: Entrepreneurship as a noble journey

Final Takeaways

• Listen more than you talk: Power and opportunity flow to those who observe and absorb before acting.
• Execution beats ideas: “Diamond dust” ideas are everywhere; few can reliably execute.
• Founders matter: Removing the founder often kills deals. Founders are the heart and memory of an organization.
• Storytelling builds brands: Authenticity trumps transactionality for lasting customer relationships.
• Own your failures: Investors want leaders who claim responsibility and learn fast.
• Be tech-enabled and adaptable: Successful entrepreneurs constantly upgrade their tools and processes.
• Diversify wisely: O’Leary’s rule—limit exposure to one sector or company, except in real estate which he knows intimately.

Book Recommendation

• Keith Richards’ Autobiography (Life)
  “[It’s] all about longevity and focus, sticking on mandate... there’s so many lessons to be learned.” — Kevin O’Leary [31:14]

Closing Quote

"If you ever get a chance to come to one of these sessions, you should. It's just a group of entrepreneurs just talking about building businesses. And I think there's nothing more noble than that."
— Kevin O’Leary [32:08]