Podcast Summary: The Code To Winning

Episode: 062 – Building Wealth Through Reinvention: Inspiring Journey of Resilience
Guest: Matt Chick
Host: Kagiso Dikane
Date: October 16, 2025

Episode Overview

In this episode, Kagiso Dikane interviews Matt Chick—a real estate investor, entrepreneur, coach, and team leader—about his transformative journey from poverty to entrepreneurial success. The discussion delves into mindset shifts, resilience, the mechanics of real estate investing, building genuine relationships, and the disciplined habits required to "win" in business and life.

Key Discussion Points and Insights

1. Rags to Riches: Origins of Resilience

• Background of Hardship:
  • Matt details growing up in poverty, absent father, and a household with minimal income ([00:00], [01:47], [02:13]).
  • Learned work ethic by observing what not to do: "I learned how to be a good human by watching other people be bad." — Matt Chick ([00:00], [02:13]).
• Mindset Shift:
  • Decision to break out of generational poverty and refusal to repeat negative patterns.
  • "You either become the thing that you hate the most or don’t become the thing that you hate the most." — Matt Chick ([00:00], [02:13]).

2. Dealing with Anxiety and Leveraging It

• Anxiety as a Motivator:
  • Matt discusses ongoing anxiety and turning it into a "superpower" by using it to catalyze action ([05:22]).
  • "Now anxiety puts me into action. The thing that’s creating the anxiety—if I can take action towards it, then it doesn’t [stop me]." — Matt Chick ([05:22]).

3. Pivot to Real Estate: From Cars to Creating Opportunities

• Career Crossroads:
  • Left a high-stress car dealership job for real estate, motivated by family needs and the desire for autonomy ([06:19]).
  • "Car business, I was capped. I was never going to make any more money." — Matt Chick ([07:55]).
• Passion for Investing:
  • Embraces real estate investing for the ability to create his own income and design his lifestyle.
  • "At the end of the day, you get to decide what you make on that deal." — Matt Chick ([08:02], [08:24]).

4. The Truth About Real Estate Flipping

• Finding the Deals:
  • The foundation is "deal flow"—find great deals, and the rest follows ([10:39]).
  • Early success came from cold calling, bulk texting, networking, and creating a focused "hit list" of potential investors ([10:39]).
  • Raised capital through genuine relationships—$1M at first, eventually $7.5M, all on handshakes ([13:02], [13:52]).
  • "I raised seven and a half million on a handshake. Didn’t have any... no contracts." — Matt Chick ([13:52]).
• Scaling Lessons:
  • Discovered the risks of scaling too fast, the need to mix private and hard money, and adapted when setbacks hit.
  • Repaid investors after losing nearly half a million in the 2022 market dip: "I lived on my savings while I paid him back because that was the right thing to do." — Matt Chick ([14:16]).

5. Strategies for Entering Real Estate

• Active vs. Passive Income:
  • Prefers "active income" strategies (wholesale, fix and flip, novations) over conventional rentals:
    "I absolutely hate [residential rentals]." ([15:25])
• Explaining Novations:
  • Novation is "replacing one contract with another" and allows for creative exit strategies. Used primarily out-of-state ([16:25], [16:29]).

6. Integrity & Avoiding the “Fake Guru” Trap

• On “Gurus”:
  • Critiques post-COVID wave of so-called experts selling courses without real experience. Emphasizes genuine track record and honest networking ([09:09]-[10:09]).
  • "Social media has changed the game. You don’t need... If you have popularity, you have everything." — Matt Chick ([09:18]).

7. Investment Risks, Discernment, and Relationships

• Deal Discipline:
  • Only pursues deals he can physically inspect and thoroughly underwrite; risk discipline learned through costly mistakes ([41:23]-[42:20]).
  • "If I can’t walk it, cool—send it to someone else." — Matt Chick ([41:51])
  • Focuses on "disqualifying" deals first: "I literally look at every deal on why it's not a deal." ([42:04])
• Investor Relationships:
  • Built on trust, integrity, transparency, and a few “tough” times:
    "When he goes, 'I’m gonna take 100% of the hit,'... I’d go to war for him. I’d protect his family like he was mine." — Matt Chick ([45:10]-[45:47])

8. Business Structure, Delegation, and Team Building

• Clarity in Roles:
  • Embraces delegation: "I’m really good at step one... step two through 99, I need someone else to do." ([33:19]-[33:52])
• Recruiting and Culture:
  • "The number one thing to focus on... when you’re building a real estate team is recruiting. Always be recruiting." ([30:29])
  • Key standards: daily connects, task completion, high participation, spirit of contribution:
    "Don’t be an asshole. What that really means is have a spirit of contribution." ([34:36])
• Attrition and Retention:
  • Retention remains challenging (30% attrition), but focus is on building culture and providing opportunities ([37:02]-[37:27]).

9. Habits, Coaching, and Personal Development

• Consistency is Key:
  • "Entrepreneurship is actually really boring... the boring things are what works." — Matt Chick ([31:43])
• Investing in Coaching:
  • Spends $6k/month on various coaches across business, marketing, and health ([27:09]-[28:20]).
  • Sees coaching as a "cheat code" to accelerate success and accountability ([28:32], [29:09]).
  • "I’ve never, ever interviewed a single person... that has not invested in themselves." — Host ([28:20])

10. Philosophy on Winning and Success

• Definition of “Winning”:
  • "First thing that comes to my mind is relationship with God." ([49:18])
  • Relentless pursuit of a purpose:
    "It’s about living with purpose and never losing sight of that purpose. Having something to live for that’s greater than yourself." — Matt Chick ([49:18]-[50:07])

Notable Quotes & Moments

• On Poverty:
  "You learn work ethic by watching my stepdad call out of work or my mom not work... I learned how to be a good human by watching other people be bad." (Matt Chick, [00:00])
• On Anxiety:
  "Anytime I’m anxious it’s because I’m not taking action... Now anxiety puts me into action." (Matt Chick, [05:22])
• On Real Estate Investing:
  "If you can find the deal, you can find everything else." (Matt Chick, [10:39]) "Raising capital is no different. This is what we could do if you come along on the ride with us." (Matt Chick, [13:02])
• On Integrity with Investors:
  "I lived on my savings while I paid him back because that was the right thing to do." (Matt Chick, [14:16]) "It was on a handshake. There’s no flipping way I would walk away from that." (Matt Chick, [14:48])
• On Coaching:
  "If you don’t know the answer, you can either go figure it out, or you could pay someone that’s already been there." (Matt Chick, [27:53]) "It’s a cheat code. I can pay someone... people that have done it." (Matt Chick, [28:32])
• On Focus and Discipline:
  "Made a decision to just stay laser beam focused on what I’m good at... and say no to everything else." (Matt Chick, [26:25]-[26:36])
• On Relationships:
  "If one dude was in a fight, you all were in a fight... It only comes by being authentic and vulnerable." (Matt Chick, [46:34])
• On Simplicity:
  "I drive a 98 Silverado, right? And people make fun of me all the time... I live a simple life, man." (Matt Chick, [48:10])

Key Timestamps

• 00:00-02:13 – Matt’s background, poverty, work ethic, foundational mindset
• 05:22 – Turning anxiety into action
• 06:19-08:24 – Real estate as the “way out”; career transition, immediate challenges
• 10:39-13:52 – Building flipping business, raising capital, importance of relationships over paperwork
• 14:16-14:48 – Taking losses, repaying investors, integrity
• 15:25-17:21 – Real estate strategies: active income, flipping, novation explained
• 27:09-29:09 – Mentorship, coaching, habits, accountability
• 30:29-32:18 – Team building, recruitment and the discipline of consistency
• 33:19-34:24 – Delegation, self-awareness in business structure
• 41:10-42:20 – Biggest painful investment, lessons learned, new deal discipline
• 46:34-47:58 – Building genuine relationships, the value of vulnerability
• 49:18-50:07 – What “winning” means; purpose, faith, and sustained pursuit

Final Thoughts

Matt Chick’s journey is a testament to resilience, focus, and authentic relationship-building. For those navigating real estate, entrepreneurship, or personal transformation, Matt’s philosophies—turning adversity into a superpower, being radically honest, investing in mentorship, and upholding integrity with stakeholders—offer a robust blueprint for sustainable "winning."

Connect with Matt Chick:

• Instagram: @IAmMattChick
• Facebook: Matt Chick

“The code to winning: Insights you need today to seize the world tomorrow.”