You’ll sit on that email for months. Maybe years. Because asking for help with your money means someone is finally going to see everything you’ve been hiding.

Kristina Hall sat on ours for almost two years before she sent a single document. In this one we get into why asking for financial help feels like dying, the advisors who made it worse, and the moment she realized she either opened her books or shut her business down.

This is for every business owner white-knuckling it alone, telling yourself you can handle it while the hole gets deeper. You can’t. And you’re not supposed to.

Chapters:
0:00 The Two Hardest Things About Getting Financial Help
2:00 “I Wanna Puke”: Why Asking For Help Wrecks You
4:00 When “I Can Handle It” Stops Being True
6:00 The Hole You Don’t Know You’re Digging
8:00 Bad Referrals and Advisors Who Don’t See You
11:00 I Asked For Tax Help. You Sold Me Products.
14:00 The Email That Asks For Every Damn Document
17:00 Two Years to Hit Send and the Breaking Point
24:00 The Tightrope, the Safety Net, and the Spiral
29:00 3 Moves to Start the Work and Just Send the Docs

This conversation pointed out an important distinction. Stress can come from uncertainty, cash flow variability, economic conditions, or the pressure of supporting a business and household at the same time.

That is different from reckless spending or poor money management.

Business owners especially experience stress tied to unpredictability. Revenue fluctuates. Markets change. Expenses increase.

The emotion attached to that pressure is not always a sign of failure. Sometimes it’s a reflection of responsibility.

Progress starts with accurate self assessment.

This conversation focused on something a lot of people avoid, honestly identifying where they are emotionally, financially, and mentally.

Especially as a business owner, pressure compounds quietly. Responsibility increases, uncertainty increases, and many people continue operating without processing any of it.

Acknowledging the situation and the emotions attached to it creates clarity.
Clarity increases capacity for better decisions.

Financial wellness is mental wellness. Dr. Preston Cherry and Stoy Hall on business owner burnout, decision fatigue, the honest self-audit, and why more money won’t fix what’s broken in your head.

Tax season’s over. Tariffs, war, graduations, business cycles, household pressure, all hitting at once. And you’re sitting there wondering why more money isn’t quieting the noise.

Dr. Preston Cherry is back in the booth with @stoyhall, and we went where most people won’t go. You can’t out-earn the inner work. You can’t out-hustle the self-audit you’ve been ducking. The gap between knowing what to do and actually doing it? That gap is you.

CHAPTERS
00:00 The Weight You’re Carrying Right Now
02:00 First-Gen Wealth Builders and the Stage You’re Actually In
04:30 Financial Wellness Is a Continuum: Mind, Heart, Money, Meaning
09:30 The Honest Self-Audit: Admit, Acknowledge, Act
12:30 Noise Check: “Stressed About Money Means You Suck At It”
15:00 32% of Americans Think 2026 Gets Worse (And That’s Truth)
19:00 Wealth Funds Wellbeing: Why Money Alone Won’t Fix You
23:00 35,000 Decisions a Day Is Wrecking Your Judgment
27:30 Drill Deep, Not Wide: Dr. Cherry’s Burnout Reckoning
30:30 The Gap Between Knowing and Doing Is You

Father’s Day is over. The weight isn’t.

Every father in your life is carrying something he won’t say out loud. The pressure to provide. The fear of not being enough. The shame of not knowing. And the financial industry has spent decades pretending that silence isn’t doing real damage.

Men experiencing economic insecurity are 16.3 times more likely to report suicidal ideation than women. That is not a typo. That is shame, silence, and the lie we all got handed about what a “real man” looks like when the money gets tight.

In this episode, I sit down with financial therapist Ashley Quamme to break down the intersection of masculinity, money, and mental health. We talk about why men won’t ask for help with money, why your financial decisions are 80% emotional, what financial therapy actually is (and isn’t), and how to have this conversation with the dad, husband, brother, or son in your life without making him shut down harder.

If you’re a father, raise a father, or love one, watch the whole thing.

Chapters:
00:00 Father’s Day Is Over. The Weight Isn’t.
02:30 Masculinity, Money, And Mental Health Are The Same Story
03:30 The Hardest Time In History To Be A Father
05:30 The Sprints Story And Lessons Moms Won’t Sign Off On
10:00 The Shame Of Not Knowing And Refusing To Ask
15:00 Noise vs Truth: The Lies About Men And Feelings
17:00 The 16.3x Stat Every Father Needs To Hear
19:00 First Gen Wealth And The Weird Family Reunion
23:00 Ashley’s Framework For Fathers And Those Who Love Them
30:00 Cut The Shit, Dads. The Closing Truth.