Wake Up to Wealth — “From Rock Bottom to Building an Empire: The Journey of Jon Cheplak”

Podcast: Wake Up to Wealth
Host: Brandon Brittingham
Guest: Jon Cheplak
Date: September 19, 2025

Main Theme Overview

In this inspiring episode, Brandon Brittingham welcomes his longtime coach and mentor Jon Cheplak to explore Jon’s extraordinary journey from hitting rock bottom—struggling with addiction and financial ruin—to building a multifaceted business empire in the real estate and coaching industries. Their candid conversation covers themes of personal development, entrepreneurial discipline, the power of simplicity, resilience, leading with contribution, and the importance of staying true to one’s core competency.

Key Discussion Points & Insights

1. Jon’s Journey: From Rock Bottom to Empire

• Addiction and Hitting Bottom:

  • Jon candidly discusses his 20-year battle with addiction and repeated stints in rehab, finally getting clean at 41 ([03:23]).
  • At rock bottom, he was $4.3 million in debt to the IRS and struggled under the weight of a public reputation crisis.
  • His brother motivated him to “do the right thing in every aspect of your life,” leading Jon to focus purely on “winning one day at a time.”

    "All I focused on was winning one day at a time. It's cliche, but cliches are around because they're true if you really live by it.” — Jon Cheplak ([04:31])

  • Credits his sustained personal development as the foundation for his business comeback.

• Business Rebirth and Growth:

  • Built a new life with a focus on discipline, consistency, and daily small wins, not grand, distant goals.

2. Building Multiple Businesses Ground-Up

• Cheplak’s Ventures:

  • Started one-on-one coaching, scaling from $199 calls to $2,000 for a 20-min session ([06:14]).
  • Grew his practice to include 14 coaches, multiple online courses, and involvement in team-building platforms.
  • Launched Digital Maverick (ISA teams for real estate), Easy Home Search (exclusive, county-by-county real estate leads), a mortgage company ($200M+ funded in 2024), and a recruiting appointment business.
  • Emphasizes all business arms are thriving, especially due to resilience and a focus on simplicity, consistency, and contribution.

• Key Growth Lessons:

  • Master one area before expanding.
  • Grow deep, not wide: “We went 12ft deep, one inch wide for years and years… before we expanded.” — Jon Cheplak ([07:44])

3. The Power of Consistency and Simplicity

• Consistency in Marketing and Message:

  • Jon and Brandon highlight the dangers of “changing your message because you get bored or impatient,” emphasizing the magic of relentless persistence ([12:24]).
  • “Pick the problem you solve, know your avatar, and do not abandon it.” — Jon Cheplak ([13:25])

• Simplicity Over Complexity:

  • The most effective growth comes from simplifying: “Simple solves the complex… Our future is in our past.” — Jon Cheplak ([15:41])

• Common Entrepreneurial Pitfall:

  • Avoid getting “bored” with what works or chasing shiny objects.
  • “People think the results make you disciplined, committed, and consistent. Results over a sustained period with growth — that's where it's measured.” — Jon Cheplak ([18:23])

4. Shared Traits of Top Performers

• Universal Factors:

  • Hunger: “Conscious hunger” is always present among top clients ([20:25]).
  • Service: An “unconscious” drive to serve, help, and support others is what sustains high achievers through pain and challenge.

• On Facilitating Growth:

  • True leaders pride themselves on facilitating others through discomfort and helping their people walk through doors of fear ([22:17]).

5. The Principle of Contribution

• Give First, Sell Later:

  • Jon is known for years of giving out value and resources with “zero call to action.”
  • “To keep what I have, I must give it away… to 100x what I have, give it away.” — Jon Cheplak ([23:14])

• ROI Comes From Contribution:

  • “If you come from a contribution standpoint, and if you give away to the market, the KPIs and the ROI are going to fucking smoke everything.” — Brandon Brittingham ([24:40])

• Modern Challenge:

  • In a “trust recession,” leadership and marketing must prioritize lowering client guard with authentic contribution, not tactics or scripts.

6. Staying in Your Core Competency

• Common Entrepreneur Error:

  • Many entrepreneurs, as soon as they hit some success, get distracted and leave their core strengths ([30:44]).
  • “You’re too academic in your business… Just because you can pay someone to do it doesn’t mean it’s right for you.” — Jon Cheplak ([31:09])
  • Cites Dean Graziosi: “60% of your day should be in your core competency.” ([32:56])

• Customer Connection:

  • Remaining close to the client reveals business opportunities—Jon’s expansion into new ventures always came from listening to customer problems ([36:29]).

Notable Quotes & Standout Moments

• “It was the best… time of my life. It shaped me.” — Jon Cheplak reflecting on his lowest point ([03:54])
• “Clichés are around because they're true if you really live by it.” — Jon Cheplak ([04:31])
• “We went 12ft deep, one inch wide for years and years until we established... you just master your craft.” — Jon Cheplak ([07:44])
• “You got to decide who is your audience and what is the number one thing that keeps them up at night.” — Jon Cheplak ([12:46])
• “Be willing to inspect. People get bored and their identity comes in... the results don’t make you disciplined, committed and consistent—results over a sustained period of time with growth, that's where it's measured.” — Jon Cheplak ([18:18])
• “If you come from a contribution standpoint... the KPIs and ROI will fucking smoke everything.” — Brandon Brittingham ([24:40])
• “In a trust recession… you can't sell until you have lowered someone's guard, period.” — Jon Cheplak ([25:43])
• “What's a business? It's a problem that people have and you solve.” — Jon Cheplak ([36:41])
• “Waking up to wealth means living every day true to my heart… with my friends and family, in my passion.” — Jon Cheplak ([38:37])
• “All your dreams, hopes, and desires are on the other side of how you contribute to others.” — Jon Cheplak ([41:21])

Important Timestamps

• 03:23 — Jon’s personal rock bottom and recovery
• 06:14 — How Jon built and scaled his businesses
• 12:24 — The magic of an unchanging message
• 15:41 — Simplicity as a growth accelerator
• 20:25 — Universal traits among top performers
• 23:14 — Principle of contribution and giving away value
• 30:44 — The importance of core competency
• 36:29 — Listening to customer pain reveals new business
• 38:37 — Jon's definition of 'waking up to wealth'

Where to Follow Jon Cheplak

• Instagram: @cheplaklive
• Facebook: Jon Cheplak (personal page)
• Website: cheplaklive.com

Episode Takeaways

• Small, consistent wins and relentless discipline trump chasing big, distant goals.
• Simplicity and clear messaging are far more effective than complex strategies or reactivity to trends.
• Contribution, authentic value, and service build trust and lasting success in today’s skeptical market.
• Staying close to your customer and core strengths unlocks new opportunities and sustains your business through challenges.
• True wealth is investing your days in what you love, with those you love — freedom, passion, and generosity.

This episode is essential listening for anyone seeking not just business success but personal transformation and authentic leadership in challenging times.