Podcast Summary: The Code To Winning

Episode 070: "From Flipping Couches to $100 Million in Real Estate"

Guest: Ryan Pineda (Entrepreneur, Real Estate Investor, Content Creator)
Host: Kagiso Dikane
Date: December 16, 2025

Episode Overview

This episode features Ryan Pineda, a self-made entrepreneur who transitioned from professional baseball to building a $100 million real estate empire and multiple successful businesses. Ryan shares candid reflections on failure, the evolution of side hustles, the ever-shifting landscape of real estate, the power of social media, and the foundational importance of building effective teams. The conversation blends actionable business advice with Ryan’s personal philosophy and real-world stories, making it essential listening for entrepreneurs and business professionals.

Key Discussion Points & Insights

1. The Journey: Baseball to Business

• Early Dreams (00:00-00:30; 04:34-05:57)
  • Ryan recounts his path as a professional baseball player with the Oakland A’s.
  • After being released (“I just wasn’t good enough” [00:30]), he turned to side hustles to support his growing family.
• Transition to Entrepreneurship
  • Started flipping couches on Craigslist before venturing into real estate flipping in 2015.
    • “I start flipping couches…I randomly figured out…then I got into real estate investing and I started flipping houses in 2015, and that changed my life.” (00:30-05:57)
• Scaling Up
  • Diversified into multiple business ventures: coaching, tax firm, real estate brokerage, and more.
  • Gained a significant social media following during the pandemic, amplifying his entrepreneurial reach.

2. The Importance of Failure and Transparency

(07:04-09:47)

• Mindset on Failure:
  • “Failing is inevitable in life, especially in business. You know, I learned in baseball, if you fail seven out of ten times, you’re really good. That means you bat .300.” (07:30)
• Learning from Losses:
  • Ryan emphasizes he wouldn’t change his mistakes because each one helped shape his success.
  • “If you only win…eventually you will lose and you will fail no matter how good you are. And I learned far more from those than I did from just only winning.” (09:23)
• Transparency on Social Media:
  • “Before social media, I was used to failing...it only became public until social media happened that then my failures became public. And then you get people scrutinizing you.” (07:30)

3. Side Hustles & Wealth Building

(10:12-13:45)

• Evolving Side Hustles:
  • “Flipping literally anything is a great side hustle…that’s all I’ve ever done my whole life. I flip houses, I flipped couches, I flipped cell phones, trading cards...” (10:40)
• Real Estate as Long-Term Wealth:
  • Real estate offers both short-term cash flow and long-term wealth. (12:42)
• AI and Marketing as the ‘Middle Ground’:
  • “If I wanted to pick something in between [side hustle and long-term]: getting really good at AI and marketing.” (12:42)

4. The Evolution and Challenges of Airbnb & Real Estate

(13:45-20:39)

• Airbnb Early Adopter:
  • Accidentally entered vacation property rentals in 2017, making significant cashflow and later selling for large profit.
    • “I bought my first [Airbnb] in 2017...I could not believe how much money it made.” (16:31)
• Market Challenges:
  • Airbnb landscape shifted: guest expectations, competition, and regulations increased, especially after his viral social media content prompted local laws.
• Today’s Real Estate Market:
  • Transaction volume in past three years is at a 30-year low, making the current market “the hardest three years of my lifetime.” (18:36)
  • Advice: Focus less on the ‘hot markets’—just “get undervalued real estate, and you have instant equity from day one.” (20:39)

5. Building Teams for Growth

(21:01-28:38)

• Three Investment Priorities:
  1. Invest in Yourself (skills and knowledge)
  2. Invest in the Business (tools, resources)
  3. Invest in People (building and training the right team)
• On Passion and Expectations:
  • “If they were so passionate and so just hyper, you know, all these things, they’d probably have their own thing going on. Right?...Most people are nine to five employees. They crave security. They like being told what to do, and they like clocking in and clocking out.” (26:03)
• Hiring Lessons:
  • Be realistic about team members’ motivations; passion akin to an owner’s is rare and shouldn’t be expected.
  • “You want somebody like you, well, what do you make? That’s what you’re gonna pay them?” (28:38)

6. Fundamentals, Focus & Diversification

(28:38-33:52)

• Business is Business:
  • Success is rooted in universal principles: “The fundamentals are the same—marketing, sales, product, hiring, fulfillment, financials.” (29:23)
• Focus Before Diversifying:
  • “It’s really hard to become an expert in one thing, period. So you’re definitely never going to become an expert focusing on multiple things. It’s literally impossible.” (30:08)
  • Ryan shares how each new focus (baseball, couch flipping, real estate, content, paid ads) took years of dedication before pivoting.

7. Marketing: Paid Ads vs. Organic Content

(33:52-40:06)

• Organic Content’s Power:
  • “Organic will beat paid every time because it doesn’t cost anything…when I make videos and people just buy a $10,000 product from me and it cost me nothing to acquire the customer, that’s like a very profitable thing.” (35:44)
• The Role of Paid Ads:
  • Paid ads are essential for reaching cold audiences but perform best when paired with established organic content and brand trust.
  • “Paid is very difficult if you don’t have a brand...they both go hand in hand. They’re both necessary.” (35:44-38:42)
• Shifts in Social Media:
  • The playing field is crowded: “all of them have money, they all have years of being known…makes it hard for somebody new to break through.” (38:46)

8. The Future: Streaming and Business Content

(40:06-46:34)

• Rise of Streaming:
  • Live selling (e.g., TikTok shop) is making millionaires; celebrities and personalities now build global followings via streaming.
  • “They have streamers who they pay, who literally their job is to go sell…on these live shows.” (41:20)
• Streaming in Business:
  • Not as big in the entrepreneurial space—hard for business audiences to commit to long-form streams.
  • “Business is like a never ending game. You just win if you don’t give up.” (49:29)

9. Choosing the Right Opportunities

(46:37-48:56)

• Ryan’s framework for assessing new ventures:
  1. Time Commitment:
     • “How much time is it going to take and is that a good use of that time?” (47:00)
  2. Shared Values in Partnerships:
     • “I will not partner with anyone who’s not a Christian anymore and a real equally yoked Christian.” (47:00)
  3. Alignment With Existing Business:
     • “I already know will instantly pop off because I already have the customers for it. They already know, like and trust me…” (47:00)

Notable Quotes & Memorable Moments

• On Self-Awareness in Failure:

  • “No, you’re just not good enough. Get better. It’s that simple.”
    —Ryan Pineda (00:30, 04:34)

• On Taking Risks:

  • “I maxed out all my credit cards and went for it.”
    —Ryan Pineda (05:59)

• On the Learning Value of Defeat:

  • “I feel like I’m so much smarter and a better business person because of [failures].”
    —Ryan Pineda (07:30)

• On Real Estate:

  • “Just get undervalued real estate, and you have instant equity from day one.”
    —Ryan Pineda (20:39)

• On Team Building:

  • “It’s time and money when it comes to team. You got to spend time setting the culture, hiring them, developing them…Also, you get what you pay for. If you don’t have talented people, I always say, something went wrong.”
    —Ryan Pineda (24:44)

• On Focus:

  • “All the skills I possess today were focused on for years at a time before I finally was like, okay, this skill is…at a level that I deem sufficient. And now I’m going to go focus and learn another skill.”
    —Ryan Pineda (33:52)

• On Winning:

  • “To me, winning is just not giving up…I really just believe that you win if you don’t quit…winning is just outlasting the competition.”
    —Ryan Pineda (49:29)

Timestamps for Key Segments

| Segment | Timestamp | |-----------------------------------------------|----------------| | Ryan’s baseball beginnings | 00:00–00:30 | | Early entrepreneurial hustle (couch flipping) | 04:34–05:59 | | The power of embracing failure | 07:04–09:47 | | Best side hustles for 2026 | 10:12–13:45 | | Airbnb journey and market insights | 13:45–18:12 | | State of today’s real estate market | 18:12–20:39 | | Building teams and expectations | 21:01–28:38 | | Focus vs. diversification | 28:38–33:52 | | Organic vs. paid marketing | 33:52–40:06 | | The streaming revolution | 40:06–46:34 | | Evaluating new opportunities | 46:37–48:56 | | Ryan’s definition of winning | 49:29–50:35 |

Final Thoughts / Takeaways

• Persistent adaptation and honest self-assessment are key drivers in Ryan Pineda’s journey.
• Flipping—whether couches or houses—can be a life-changing side hustle, but bigger wealth comes with scalability and long-term thinking.
• Building a strong, aligned team is essential, but leaders must be realistic about passion and drive.
• The fundamentals of business (marketing, team, focus) never change, even as platforms and tactics evolve.
• Winning in business is a matter of perseverance and outlasting the competition.

For more from Ryan Pineda or to learn about his coaching programs, check the episode description.