Podcast Summary: School of Hard Knocks Podcast

Episode: Chris Watters | CEO of Watters International Realty – Going From $0 to $10M+/Yr & Doing 9 Figures in Revenue in Real Estate
Date: January 31, 2024

Episode Overview

In this episode, the hosts James and Josh sit down with Chris Watters, CEO and founder of Watters International Realty, one of the largest real estate brokerages in the U.S. Chris shares his personal journey from starting a lawn mowing business as a teenager, through hitting rock bottom after a failed bar and restaurant venture, to building a real estate company generating hundreds of millions in annual sales. The conversation centers on actionable entrepreneurial insights, the importance of humility and focus, hiring strategies, the skill set needed for real estate success, and creative tactics for building wealth in today’s real estate market.

Key Discussion Points & Insights

1. Chris’s Early Journey: From Lawn Mowing to Real Estate

• Chris’s entrepreneurial start: At 12, launched “CJ’s Lawn Service” after his mother encouraged him to earn money for extracurriculars (15:58–18:14).
• Learning from flipping: Bought discounted car audio from Circuit City, resold on eBay – got fired, but learned about arbitrage (18:14–19:38).
• Transition to real estate: Inspired by an exacting lawn care client who recruited him into real estate; initially lacked humility and coachability, leading to early struggles (00:35–02:30).

2. Hitting Rock Bottom and Bouncing Back

• Bar & restaurant failure: Invested all his savings in 2009 into a 6th Street Austin bar/restaurant after reading alcohol sales spike in recessions. It failed within nine months, leaving him broke (03:42–04:30).
• Turning point: With “less than $10” in his account, Chris recommitted to real estate, cold calling relentlessly but failing at first due to lack of skill and empathy (04:30–08:30).

Quote:
"About nine months later, I show up, and there's chains around the door... man, I was so broke. Like, I mean, I'm not even kidding. I don't even think I had $10 in my account."
— Chris Watters (04:00)

3. Skills-Based “Millionaire Blueprint” for Entrepreneurs

• Inside Sales: “You gotta learn how to have influence on the phone and book an appointment... That is a skill, and literally, people spend their entire career just focused on that one skill.” (09:30)
• Outside Sales: "The bridge to riches in real estate is learning how to convert complete strangers into clients.” (10:50)
• Subject Matter Expertise: Comes last, built through doing deals, not before (11:30–12:10).

Memorable Summary:
"There's three basic dominoes... inside sales, outside sales, and then subject matter expertise—it's all skills-based."
— Chris Watters (11:00)

4. The Importance of Humility and Failure

• Chris describes losing his “edge” after buying an Audi R8 post-first million, emphasizing the need to constantly set new challenges to avoid stagnation (13:03–15:22).
• Rock bottom and adversity catalyzed his growth, making him more coachable and focused (12:17–13:20).

Quote:
"It's this weird headspace... you feel like you've kind of made it... you get comfortable. Through forward progress, we find happiness."
— Chris Watters (14:05)

5. The Power of Focus & Expertise

• Entrepreneurs get distracted after reaching “proverbial ceilings” instead of creatively scaling core businesses.
• Staying focused on the main business leads to greater long-term growth (21:21–22:17).

Quote:
"If you actually stayed focused on your core business and kept thinking creatively about how to keep pushing it to the next level, you would continue to grow by leaps and bounds."
— Chris Watters (21:40)

6. The Role of Coaches and Accountability

• Chris shares that not having a coach led to getting spread too thin (“wheels started falling off”) (22:42–25:30).
• Now has a CEO advisor, financial coach (for decision modeling), and marketing advisor (25:44).

Quote:
"Today, 2024... I have more than one coach. I have a CEO advisor, a financial advisor, [and a] marketing advisor..."
— Chris Watters (25:44)

7. Humility, Modeling Success & “Pioneers vs Settlers”

• Emphasizes modeling proven business models before innovating, referencing Daymond John’s Shark Tank quote: “Pioneers get slaughtered, settlers prosper” (26:44).
• Highlights the success found in “unsexy” businesses (HVAC, plumbing) rather than reinventing the wheel (26:44–29:00).
• Test ideas on a small scale; don’t go “all in” too early (30:43–33:41).

8. Mastering Sales and the Art of “Selling Yourself”

• Confidence and enthusiasm are crucial—clients hired him not for expertise, but excitement and drive (35:12).
• "If you're a hungry, driven, excited person, people pick up on that... that’s easy to sell.” (35:12)
• Passion is at the root of personal selling (36:41).

9. Scaling and Hiring: From Utility Players to Unicorns

• Scaling means shifting from personally “leading your customer to success” to building a team of leaders (38:29).
• Most of the team will be “utility players,” not unicorns—find and nurture enough leaders (38:29–39:45).

Quote:
"Your organization is going to be made up of utility players. You just need enough unicorns to lead the army."
— Chris Watters (39:29)

• Recurring hiring insight: Most agents hate prospecting/cold calling; business model must adapt to workforce preferences (41:04–44:11).

Quote:
"98% of realtors that walk in the door are not a market expert... the one daunting task [agents] hate is prospecting on the phone."
— Chris Watters (41:04)

10. Building Teams & the Art of Selection

• Specialization is key to high-growth companies.
• Referenced the book “The Rare Find”: The best organizations have high barriers to entry and test practical skills, not just interviews (48:22–57:53).
• Shared a detailed example of simulating tough sales calls during interviews to evaluate real-world responses (54:28–57:53).

Quote:
"The interview process is bullshit... everybody can fake it for an hour. The more you can inject practical application into the job interview... the higher the likelihood is you're going to find the right person."
— Chris Watters (54:29, 58:00)

11. Real Estate Investment Strategies—Current Landscape

• Recommends “subject to” deals: Take over mortgage payments for sellers with little equity and low rates, renting the property for positive cash flow (59:34–61:09).
• Points out public records can provide leads for wholesaling—find distressed owners, get home under contract, and sell to investors (61:09–63:36).
• Reinforces: “You don’t need a lot of money; you just need to find a deal.” (63:36–63:44)

Notable Quotes & Memorable Moments

• Chris on failure:
  "You almost got to be, like, sadistic about it, where you're like, I want to struggle. Like, I want to find a way to make myself struggle." (15:22)
• Chris on coaching:
  "If you're an entrepreneur, you're probably very optimistic. And so you kind of need somebody to be your devil's advocate all the time, like challenging what you think is going to work out." (25:30)
• Chris on selling:
  "Man, I don't know, I think selling yourself is fairly easy... if you're excited about something, like, other successful people pick up on that." (35:12)
• Chris on team roles:
  "If you look at every Inc 500 company, the whole company is made up of an army of specialists." (48:30)
• Chris’s selection mantra:
  "RSTLM—Recruit, Select, Train, Lead and Motivate. But if you had to boil it down, selection is most important." (52:32)

Timestamps for Key Segments

• Chris’s Background – 00:35–03:42
• Bar/restaurant failure & pivot to real estate – 03:42–08:30
• Millionaire blueprint: inside/outside sales, expertise – 09:30–12:17
• On hitting rock bottom & adversity – 12:17–15:22
• Entrepreneurial DNA, humility, and mindset – 18:14–21:21
• Coaches, accountability, & the dangers of comfort – 22:42–25:44
• Pioneers get slaughtered, settlers prosper – 26:44–30:43
• Adversity and the market downturns – 30:43–33:41
• Sales—selling yourself, confidence and enthusiasm – 34:23–36:46
• Team-building—unicorns vs utility players – 38:29–40:38
• Recruiting & hiring, practical applications in interviews – 48:22–58:00
• Creative real estate investment in 2024 – 59:34–63:44

Final Takeaways

• Persistence and relentless improvement are non-negotiable in entrepreneurship and real estate.
• Mastering sales—especially phone and outside sales—is foundational to real estate success.
• Humility, adaptability, and focus are more valuable than bravado or trying to reinvent the wheel.
• Hiring and scaling: Building a great company hinges on recruiting talent, specialized roles, and raising internal standards.
• Creative real estate investment remains accessible—even for those with little cash—if one is resourceful.

Where to Find Chris Watters

• Website: ChristopherWaters.com (Real estate scholarship info)
• Instagram: @ChrisWatters

This episode is a goldmine for anyone building a business or aspiring to succeed in real estate—equal parts no-nonsense, tactical advice, and hard-earned wisdom.