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The Long Burn – "Burning the Ships"

Guest: Tim Jester, CFP and Founder of ITA Wealth Partners

In this debut guest episode, hosts Joel Malin and Dr. Jonathan Wade (aka "Dirty Dr. Wade") sit down with Nashville-based financial advisor Tim Jester. The conversation moves quickly from playful banter to a deep dive into the "grind culture" of financial services, the psychological toll of entrepreneurship, and the importance of choosing people over products.

Key Takeaways

• The "Burn the Ships" Mentality: Tim shares the story of Cortez burning his fleet to ensure his men had no choice but to succeed. He applies this to business: Plan A can only succeed when you eliminate the safety net of Plan B.
• Culture vs. Commission: Tim left the "insurance-centric" world to escape the pressure of selling products that weren't always in the client’s best interest. He argues that a truly independent practice allows an advisor to prioritize the client's goals over a sales quota.
• Rejecting "Grind Culture": The industry often rewards the "first in, last out" mentality, which Tim identifies as a recipe for broken marriages and estranged children. He built ITA Wealth Partners to prove you can have a high-performing business while still being present for school recitals and date nights.
• The 10-3-1 Equation: Tim critiques the traditional sales funnel (10 referrals lead to 3 meetings, which lead to 1 client). While mathematically sound, he finds it "icky" and disingenuous, opting instead for organic community involvement and a "long game" approach to relationships.
• Individual over Modality: Joel draws a parallel to therapy, noting that the best professionals fit the solution to the human being, rather than trying to force the human into a pre-packaged "product" or treatment model.

Memorable Quotes

The Firing Line: Question #1

The Question: What’s a failure that cost you more than money, and what did it change about how you operate today?

Tim’s Answer: Tim reflects on his 20s, where unresolved childhood pain and anger led him to "run through" personal and professional relationships. He lost clients and burned bridges with people he loved. This failure taught him the value of therapy and self-awareness, ultimately shifting his focus toward empathy and making people feel "heard and valued" rather than just being a number in a spreadsheet.

The Verdict

Who should listen? Entrepreneurs feeling the "head in hands" weight of starting out, or any professional feeling trapped in a toxic "grind" environment who needs a reminder that success doesn't have to come at the cost of your family.

Tim Jester’s journey from a high-pressure insurance firm to a values-based independent practice is a roadmap for anyone looking to "burn their ships" and build something authentic.

To get in touch with Tim Jester for financial advising, please visit https://itawealthpartners.com/ or you can reach Tim via email at tim@itawealthpartners.com

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Episode Overview: "You Don't Have a Time Problem, You Have a Priority Problem"

The core message of this episode is that everyone has the same 24 hours in a day; the difference in outcomes lies in how those hours are prioritized. The hosts argue that "finding time" is a myth—you must make or take time for what matters.

Key Takeaways

• The Difference Between "Making" and "Taking" Time:
  • Making Time: Deferring low-risk tasks (like laundry) to a later date to create space now.
  • Taking Time: Consciously choosing not to finish a task today because health or family is more important, even if it feels like "lowering standards."
• The Ceiling of a "Do-It-Yourself" Mentality: Dr. Wade shares a story about scrubbing toilets at his clinic. While it shows humility, the hosts discuss how this isn't a productive use of a CEO’s time. To grow a business, you must delegate tasks that others can do 80% as well as you.
• Busy vs. Productive: Being "busy" (doing tasks) is not the same as being "productive" (moving the needle on goals).
• The "One Thing" Strategy: Referencing Gary Keller’s book, they suggest picking the single most important task each week that creates a "domino effect" for everything else.

Personal Wins & Losses

The hosts start with a "Vulnerability Minute" regarding their personal lives:

Host | Wins | Losses/ChallengesDr. Jonathan Wade | Orchard Health is "knocking it out of the park" with a new nurse practitioner and improved marketing. | Short-term rental bookings are down; dealing with critical four-star reviews.
Joel Malin | His newborn son, Gideon, smiled for the first time, providing much-needed feedback during the "sleep-deprived" phase. | Financial stress of trying to afford a nanny, as he and his wife aren't ready for daycare yet.

Notable Quotes

Actionable Advice from the Hosts

1. Modify, Don't Lower, Standards: Reshape your expectations of a "pristine home" or "perfect schedule" to adapt to new life phases (like having kids).
2. Focus Blocks: Use dedicated chunks of time to work on specific topics rather than trying to multi-task throughout the day.
3. The "Lived-In" Perspective: Accept that a busy home or a slightly disorganized office is a sign of life and growth, not failure.

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In this episode of The Long Burn, counselor Joel Malin and Dr. Jonathan Wade explore the concept of "the family as the first team," emphasizing that personal and professional success depends on domestic alignment. The hosts open with personal "wins and losses," ranging from Joel’s successful fishing trip and frustrations with insurance hiking to Jonathan’s family visit to his son’s college, which included a humorous mishap involving a black eye during a game of wiffle golf. Transitioning to the core topic, Jonathan reflects on the eight-year journey of his medical practice, Orchard Health, detailing how he secured his wife Candace’s "buy-in" by framing the business as a way to prioritize family time over grueling hospital shifts. They discuss the necessity of "counting the cost" and establishing a family operating agreement—setting firm boundaries, such as "no-business" zones after 6:30 PM and monthly retreat nights, to ensure that the drive for professional sustainability doesn't come at the expense of household harmony.

Key Takeaways from "The Family as the First Team"

• The Power of Buy-In: Success in a new endeavor requires more than just permission; it requires a shared vision. Jonathan noted that involving his wife directly in the business allowed their complementary skills—his "big ideas" and her "boots-on-the-ground" integration—to flourish.
• Defining the "Operating Agreement": To prevent burnout and resentment, families should set explicit boundaries. This includes "work-free" hours and identifying which roles each member will play to support the collective goal.
• Managing the "Nasty Nelson" of Risk: Just like the surprise point in pickleball (the "Nasty Nelson"), business risks are inevitable. The hosts suggest viewing these not as deterrents, but as opportunities for growth and learning.
• Intentional Disconnection: Joel and Jonathan highlight that work is never truly "done." Building the skill of living in that tension—choosing to stop working to be present with family—is vital for long-term health.