The Paul Morris Podcast
Episode: Plan for the End Before You Reach the Peak
Date: February 23, 2026
Guest: Mikey Taylor (Professional Skateboarder, Entrepreneur, Real Estate Private Equity Founder)
Host: Paul Morris
Episode Overview
In this episode, host Paul Morris is joined by Mikey Taylor, former professional skateboarder turned successful entrepreneur and real estate private equity leader. Together, they dive deep into the mindsets, disciplines, and strategies that enable individuals to engineer high performance and compound wealth for the long haul. Mikey shares candid stories from his journey, spanning pro skateboarding, building and selling the craft beer brand Saint Archer, and launching/leading a real estate private equity firm. The conversation is rich with actionable insights on grit, financial planning, leveraging assets, avoiding common pitfalls, and maximizing both business and personal fulfillment.
Key Discussion Points & Insights
1. Grit, Obsession, and the "Non-Natural" Path to Professionalism
(00:50–05:00)
- Early Days in Skateboarding: Mikey started skating at age 12—not considered "early" by pro standards, and not a natural at it.
“It didn’t come natural to me... I have a very obsessive personality and I hate failing and I want to master things.” (B, 00:50)
- Mikey stresses that his success came not from innate talent but obsessive effort and grit.
- Contrasts with naturally talented athletes who often don't develop drive or persistence.
Notable Quote:
“Without that [obsessiveness], I had no chance. And that’s what you see, actually—you see the reverse for a lot of very talented kids... Some of the best skateboarders actually never go anywhere with it. That’s the fascinating part.” (B, 02:21)
2. Transferring Skateboarding Lessons to Business and Investing
(05:08–11:21)
- Mindset Shift: Skaters are forced to look at spots and tricks in totally new ways—parallel to finding market "white space" in business.
- Marketing Genius: Skateboarders must differentiate nearly identical products (boards, shoes) via branding/storytelling—skills that later set Mikey apart in entrepreneurship.
- Innovation Analogy: Not full "Rip Off and Duplicate" (R&D); instead, take fundamentals from others but innovate/differentiate at the margins.
Memorable Moment:
“You have to get really good at making your consumer think that your product is better than the others, where in theory, it’s the same product. That has absolutely crossed over for me.” (B, 06:32)
3. The Fragility of "Sponsorship Money" & The Urgency for Financial Planning
(11:21–15:12)
- Athlete Income: Skateboarding sponsorship is like a regular job—great while it lasts, but fleeting.
- Mikey was paranoid about being “owned by his sponsors” and risk of losing income post-career.
- The importance of shifting earned income into compounding assets—not just relying on work-related cash flow.
Key Insight:
“The majority of us look at wealth through the amount of income we make. We don’t calculate wealth based off how long do I not have to work and I’m still okay.” (B, 12:41)
4. Profit First and Avoiding the “Cash Eating Machine” Trap
(15:12–19:15)
- Paul introduces Mike Michalowicz’s “Profit First” methodology—discipline of paying yourself first, using separate accounts, and not running your life based solely on your current checking account.
- Both agree that default human behavior is to spend/plow money back into business/life, often leaving little for asset building or taxes.
Notable Exchange:
“The ‘pay yourself first’ model is actually the only way I’ve ever been able to save.” (B, 16:42)
5. Avoiding the Typical Athlete “Sudden Stop”
(19:18–23:04)
- Mikey’s parents pushed him to get financial help/advisors early.
- Used Dave Ramsey concepts—live on as little as possible, invest the difference.
- Prohibitive for most athletes to contemplate the end; key is to plan offensively before hitting the peak.
Notable Quote:
“On your way up, you’re not planning for the defense to protect yourself. You’re ensuring a roadmap so that after your career ends, you keep moving forward and you keep moving up... Most athletes hear it as defense.” (B, 20:26)
6. Building, Branding & Selling Saint Archer Brewery
(23:04–30:24)
- Saint Archer was launched with partners from skate/surf world, and the insight that most craft breweries lacked community, brand, and lifestyle marketing.
- Mikey leveraged the “California lifestyle” narrative and connections with athlete ambassadors.
- Achieved rapid growth and a big exit to Miller Coors.
- The importance of “blue ocean” strategy—finding white space even in crowded markets.
Notable Story:
“At that time... craft beer was really starting to grow... We brought investors in, those investors became our ambassadors. All of our marketing material was their stories—had nothing to do with beer. The only mention of beer was, ‘This video is presented by Saint Archer.’” (B, 24:32)
7. Contrasting Business Exits, Real Estate Wealth, and The Value of Leverage
(30:24–43:53)
- Paul describes how business owners’ net worth is often ~10x annual income, but for real estate owners, the “cash flow” is much less relative to net worth.
- Discussion on fundamentals: risk, yield, stable wealth, patience.
- Flipping assets vs. long-term holds: “flipping is like being a real estate agent—every deal, you’re back to zero. Holding is where you build the machine.”
- A nuanced take on leverage/Dave Ramsey: leverage is critical for wealth-building—if used wisely and with risk in mind.
Notable Quotes:
“If I did not use leverage, I would have 25% of the wealth I currently have... Leverage is definitely an accelerant. So therefore, it will really accelerate your upside and it will really bury you.” (A, 36:41)
“Dave Ramsey is not the guy that then takes you from neutral to offense to freedom. That’s not his lane... An accelerator: if I bought an asset for $100,000, all cash... If I put 20% down... it’s much greater return.” (B, 37:24)
8. “Your House Isn’t an Asset”—Asset, Liability and Home Ownership
(41:06–43:53)
- Asset classes compared: primary residence vs. rental property—differences in who pays the debt/service.
- Importance of viewing your home as a place to live, not necessarily as an investment vehicle.
- Different strategies depending on personal temperament and family needs.
9. Real Estate Private Equity Demystified & Current Strategy
(44:27–55:51)
- Mikey transitioned from skateboarding to passive real estate investing (self-storage), then to founding a private equity company for real estate.
- Private equity: pooling capital (from private investors/limited partners) to buy and operate real estate, providing investors returns and taking a percentage of profits.
- Syndications vs. Funds explained.
- Their current portfolio: ~$350m AUM, ~50% debt on storage, 40% equity on multifamily.
- Geographic focus: SoCal multifamily ground-up development below 100 units (not big enough for institutional buyers, not small enough for “mom and pop”).
- Unique Value: Entitle projects with their own risk capital, then bring investors in upon permit; Mayor of Thousand Oaks, understands planning/entitlement intimately.
Memorable Insight:
“What I like is buying assets where both sides are not trying to buy, building them to a point where the institutional investor then comes into play to be my buyer... most of our apartments range from 40 to 100 units, and the cost... from $14m to $45m.” (B, 52:00)
10. Defining Financial Freedom and How to Get Started
(57:42–64:20)
- Mikey’s definition: (1) Enough passive income to cover your lifestyle, (2) How long you can last without active work.
- Paul’s additions: cover savings, investments, contributions for true “escape velocity.”
- Mikey’s practical formula: “Start with the end in mind.” E.g., $180k/year passive → need $3 million at 5% yield.
- Early focus: growing the nest egg, not just income. Diversify (uncorrelated investments), then pivot to income.
- Biggest advice: Just get started—first deal is to open the door for the second.
Notable Quotes:
“The calculation is this: you need to grow your wealth... even though we’re talking about passive income coming in, if you pick passive income over growth, it’s gonna be a smaller return.” (B, 62:13)
“A lot of people go, it’s only $50,000. It’s only $20,000. My first investment, I think, was $5,000... The $5,000 then led to $10k... Just get started. It’s not about the first deal.” (B, 64:00)
11. Fire Round—Personal Insights
(65:14–67:49)
A quick Q&A with revealing, rapid responses from Mikey:
- Favorite childhood memory: Persevering to win a badge in Indian Guides while his dad watched proudly. (B, 65:25)
- Idea of perfect happiness: Living life aligned with your purpose. (B, 66:22)
- Greatest fear: Something happening to the kids. (B, 66:28)
- Talent wished for: Efficiency. (B, 66:36)
- Proudest insult: “You’re crazy.” (B, 66:42)
- Quality admired: Honesty. (B, 66:46)
- Trait disliked: Untethered emotion. (B, 66:54)
- Greatest extravagance: Probably equity. (B, 66:59)
- Legacy wish: Trustworthiness. (B, 67:13)
- Mountaintop shout to loved ones: “I’m going to meet my Creator.” (B, 67:46)
Memorable Quotes & Timestamps
-
On Not Being Naturally Gifted:
“It was more the way my brain was wired... not because it was just natural.” (B, 00:50) -
On Breakthrough Business Mindset:
“Skateboarding taught me to focus on the thing they’re missing. That’s a very good thing to have in business.” (B, 05:34) -
On Athlete Income vs. Assets:
“I felt like my sponsors owned my future... If I can shift all that income from sponsors into assets, I’m good.” (B, 11:47) -
On Leverage:
“Leverage is definitely an accelerant. So therefore, it will really accelerate your upside and it will really bury you.” (A, 36:41) -
On Financial Freedom:
“When income is coming in passively and you want to increase your lifestyle, the move is not ‘okay, how do I make more income?’ It’s ‘how do I get more assets on the board to then give me more passive income.’” (B, 61:16) -
On Just Starting:
“It’s not about the first deal. It’s that the first deal opens the second. That’s the framework.” (B, 64:00)
Timestamps for Important Segments
- 00:50 – Mikey’s start in skateboarding, grit > talent
- 05:08 – How skateboarding mental models transfer to business/marketing
- 11:21 – The insecurity of athlete income and the move to assets
- 16:41 – The “pay yourself first” approach, avoiding the lifestyle creep trap
- 19:45 – How fear and humility fueled solid planning early on
- 23:04 – Story of Saint Archer, blue ocean branding, monumental exit
- 30:24 – Business exits vs. real estate wealth building, leverage
- 37:24 – Nuanced discussion on the use (and risk) of leverage
- 44:27 – Real estate investment journey and education-driven business
- 50:08 – Multifamily development strategy, entitlement, and institutional “sweet spot”
- 57:55 – Defining financial freedom and future-proofing your lifestyle
- 62:13 – Getting started from zero: reverse engineering and just taking action
- 65:14 – Rapid-fire insights: personal values, fears, legacy
Final Takeaway
Mikey Taylor exemplifies the drive to intentionally engineer your trajectory—whether you’re an athlete, entrepreneur, or investor. From skateboarding to craft beer to private equity real estate, the keys remain: start with the end in mind, act with humility, transfer core learnings across fields, and build assets that compound far beyond the work you put in. Plan for the end before you reach your peak, and you’ll never have to scramble after the applause fades.
Listen for: inspirational stories, tactical frameworks for building enduring wealth, and deeply honest takes on career evolution, risk, brand-building, and real estate investing.