Podcast Summary: Earn Your Leisure

Episode Title: He Sold at the Perfect Time — Business, Investing & Economic Lessons from Mikey Taylor
Air Date: February 8, 2026
Hosts: Rashad Bilal & Troy Millings (w/ Menelik Lumumba)
Guest: Mikey Taylor – Entrepreneur, Investor, Former Professional Skateboarder, Mayor

Overview

This episode features Mikey Taylor, who shares his unique journey from professional skateboarding to building, scaling, and selling a nationally recognized brewery, entering commercial real estate, entering private equity, and ultimately a foray into local politics as Mayor. The discussion dives into high-level business and investing lessons, economic outlooks, and practical advice for entrepreneurs. Notably, Mikey outlines how he successfully timed the sale of his company, thoughts on when to exit an investment, the shifting U.S. economy, and the future of work in a world increasingly shaped by AI.

Key Discussion Points & Insights

1. Selling a Business: Timing & Strategy

• Investor Expectations and Exit Routes: Mikey explains the necessity to build either a cash-dividend engine or a business built for acquisition when you take on investors [03:58].
• Industry & Market Timing: His team decided to sell the brewery when big beverage companies were actively acquiring and paying premium multiples. They feared if they waited, the window—and the lucrative valuations—would close.
  • “Sometimes it’s timing, sometimes it’s luck, and sometimes you’re able to see some of the data and then make a maybe educated decision.” (Mikey Taylor, 05:04)
• Reluctance to Repeat Success in the Same Field: He avoided starting another brewery due to fears of diminishing returns and decided to disrupt a new industry (real estate), thereby finding new "blue ocean" opportunities [05:16].

2. Transition from Athlete to Entrepreneur

• Leveraging Athletic Discipline: Mikey credits his focus and drive to habits learned from professional sports, specifically maintaining discipline, managing risk and reward, and embracing uncomfortable transitions:
  • “I had sponsors that paid me while I was relevant ... and I did not like that feeling. It’s probably similar to just having a job and your boss basically is the decision maker on your future.” (Mikey Taylor, 06:53)
• Taking Control of One's Future: The entrepreneurial journey began as a way to move away from dependency on sponsors—paralleling a desire for ownership and long-term security.

3. Becoming Mayor: Business Skills in Local Government

• Political Involvement Explained: Initially distrusting of typical politicians, Mikey found local politics different and tangible (“budgets and sidewalks and real estate ... things we actually feel and touch every single day” [08:22]).
• Civic Ceiling: He made clear he doesn't want to pursue politics beyond the local level, planning to return to entrepreneurship after his tenure.

4. Economic Outlook – The Federal Reserve’s Changing Role

• Potential Impact of a New Fed Chair: The episode discusses what a shift toward a more "referee" and less "stabilizer" Fed would mean—potentially more volatility but fewer artificial bubbles:
  • “What it really is, is stay out of it and be the referee. I’m not going to be the stabilizer, I’m going to be the referee. And what that means is more potential volatility.” (Mikey Taylor, 09:43)
• Concerns about Economic Sustainability for Younger Generations: Mikey links today’s economic issues—especially those hampering millennials and Gen Z—to decades of propping up markets, resulting in high living costs and asset bubbles [11:51].

5. National Debt and Political Gridlock

• Limiting Paths Forward: Reduction of spending or increased revenue are the only ways out, but political appetite is lacking for both, leading to stagnation:
  • “If you’re an elected official, ... if you ran on a platform of ‘we’re cutting,’ you’re not getting elected. ... The only real shot is control expenses where they’re at and grow our way out.” (Mikey Taylor, 14:44)
• Growth via Innovation (e.g., AI): Optimism about transformative AI driving the GDP and creating escape velocity for the U.S.
• Rise of Political Independents: Sign of possible shifts in the political landscape [15:51].

6. Entrepreneurial Insight: Idea vs. Operator

• Operator > Idea: Execution is what separates successful ventures from failures, echoing the need to pair visionaries with skilled operators:
  • “There are more good ideas out there that don’t get executed than bad ideas that people try to drive forward.” (Mikey Taylor, 19:03)
• Team-building is Key: Solopreneurs should be willing to share equity and revenue upfront to build a scalable team [19:03–20:29].

7. The State of Real Estate in 2026

• Commercial Real Estate Outlook:
  • Offices are heavily challenged but will rebound in a hybrid model.
  • Industrial and retail remain robust, with “community” and human connection keeping brick-and-mortar alive.
  • Multifamily rents are correcting, especially in low-regulation, fast-building markets.
  • Broad theme: Higher interest rates have created a current “buying opportunity.” (Mikey Taylor, 21:05)

8. Millennial and Gen Z “Career Crisis” & Housing Affordability

• Concerns about Upward Mobility:
  • “I think the big issue with the millennials and Gen Z is it’s housing. ... 50 to 70% of our income going towards housing. ... The American dream is taken off the board at that point.” (Mikey Taylor, 23:07)
• Policy Solutions Debate: Calls for a blend of increased supply and smarter regulation—“the private market and the policymakers need to come together and actually speak the same language” [23:07–25:35].

9. Missed Opportunities and Lessons Learned

• Regret Over Missing Early Bitcoin: Mikey’s take: When you hear about something new, ask questions and learn; don’t dismiss out of hand.
  • “If somebody is talking about something, treat it as if they have information that you don’t have and ask questions for you to learn.” (Mikey Taylor, 25:50)

10. Demystifying Private Equity

• Private Equity vs. Real Estate Syndication:
  • PE means raising capital outside public markets; can be as small as group deals ($5,000) to huge institutional funds.
  • Typical play is to consolidate, create efficiencies, drive up EBITDA, and exit for a multiple.
  • Real estate syndication: Instead, gather investors to develop or reposition properties for group wealth generation [26:54–28:43].

11. Defining Legacy

• Character & Impact over Assets:
  • “...I think the only thing I would want them to view what I was while I was here is that I was somebody that they trusted and ... could count on.” (Mikey Taylor, 29:01)
  • Teach children values and character first, wealth management second.

12. Five High-Return Priorities for Entrepreneurs

• Sales
• Financial management
• Metrics/tracking & operational structure (EOS/Traction framework)
• Culture
• Leadership development
  • “If you have somebody that you built up and they ... end up leaving your company ... don’t get pissed at that. That’s ... a great example that you did your job as a leader.” (Mikey Taylor, 30:19)

Memorable Quotes with Timestamps

• On Selling at the Right Time:
  “Sometimes it’s timing, sometimes it’s luck, and sometimes you’re able to see some of the data and then make a maybe educated decision.” (Mikey Taylor, 05:04)
• On Entrepreneurial Discipline:
  “At the end of the day, investing should be boring, right? We just want to make it exciting. But ... establish [disciplines] and then hold to it. If you just do that, you’re gonna look back, you’re gonna be in a pretty good spot.” (Mikey Taylor, 06:25)
• On Economic Risks:
  “If you viewed America as us, as individuals, we all bring in a certain amount of money ... we are spending way too much and we are borrowing like crazy. And the inevitable outcome of that is bankruptcy.” (Mikey Taylor, 12:52)
• On Real Estate & Housing Policy:
  “The True answer is it’s going to land somewhere in the middle, like the private market and the policymakers need to come together and actually speak the same language ... and you haven’t seen that happen yet in a lot of the markets.” (Mikey Taylor, 24:15)
• On Legacy:
  “It’s more important that we instill good character and good values and give them the tools for them to go on and do their thing as opposed to just passing down assets.” (Mikey Taylor, 29:01)

Key Timestamps for Major Segments

• 03:58 — Deciding when to sell a company
• 05:16 — Transition from brewery to real estate
• 06:53 — Athlete mindset applied to entrepreneurship
• 08:22 — Getting into politics (city level)
• 09:43 — Fed chair/policy and economic volatility
• 11:51 — The debt crisis and hope for AI-driven growth
• 19:03 — Idea versus operator in business scalability
• 21:05 — 2026 commercial real estate outlook
• 23:07 — Millennial/Gen Z career and housing issues
• 25:50 — Mikey’s biggest missed investment (“early Bitcoin”)
• 26:54 — Private equity demystified
• 29:01 — Reflections on legacy
• 30:19 — Five highest-ROI business focuses

Tone & Takeaways

Mikey Taylor delivers candid, practical wisdom—honest about risk, enthusiastic about innovation, and deeply focused on values-driven leadership. This episode is packed with actionable frameworks for selling a business, investing, surviving political and economic headwinds, and building a legacy far beyond financial wealth.

For aspiring entrepreneurs, investors, and civic leaders, this conversation is a masterclass in timing, discipline, and thoughtful, adaptive leadership.