sits behind that decision? Sarah Gerdes and Chris Grant explore rejection and the realities of raising

capital, drawing on firsthand experiences with investors, family offices, and the advisors who

surround private wealth.

The conversation opens up a world where having money to invest and finding the right business can

remain surprisingly disconnected. Through candid stories, Sarah and Chris examine the requirements

that shape investment decisions: company stage, industry, geography, minimum investment size,

and even whether a founder is willing to relocate. They also discuss misleading funding approaches,

offers that turn into paid fundraising services, and the questions worth asking before sharing your

business story.

The discussion goes deeper into family offices, where generational transitions, changing leadership,

and family demands on wealth can affect investment priorities and future funding. For founders

pursuing capital, it is a conversation about understanding who is across the table, qualifying the

opportunity early, and recognizing when passing may be the right decision on either side.

KEY MOMENTS

01: What “I’ll pass” can reveal about investor fit, business requirements, and the assumptions founders

bring into the room.

02: Inside family-office investing: how investment size, industry, geography, and participation by other

investors can determine whether a conversation goes anywhere.

03: The cost of access: fundraising pitches, pay-to-play introductions, and approaches that promise

investment but lead to a sales conversation.

04: The generational factor: how inheritance, leadership changes, and demands on family wealth can

influence investment timelines and follow-on support.

05: Qualifying the capital: the questions to ask before pitching, the terms worth examining, and an

introduction to the wealth managers and business advisors explored further in a future conversation.

• (00:00) - Welcome and Introductions
• (00:50) - Raising Capital to Fund Your Business
• (02:43) - Inside the World of Private Wealth
• (05:04) - Funding Pitches, Pay-to-Play Offers, and Scams
• (06:39) - The Uber Investment That Got Away
• (07:55) - Family Offices: Ask About the Rules First
• (09:29) - The $100 Million Minimum
• (10:30) - Why Family Offices Seek Direct Investments
• (12:07) - Relationships, Access, and Finding the Right Fit
• (13:43) - The $30 Million Offer That Required a Move
• (16:51) - Sponsor Break: ContractsIQ
• (17:43) - When the Investment Criteria Align
• (18:31) - Generational Wealth and Changing Priorities
• (21:39) - Investor Stability and Future Funding
• (23:05) - A Checklist for Approaching Family Offices
• (23:58) - Helping Investors Find You
• (25:10) - Coming Next: Wealth Managers and Business Advisors
• (25:42) - Closing Thanks

Show Notes / Description
What happens when the ambition that built your dream begins damaging the people you built it with?
Dawson Scholz's story begins with family, music, and the determination to create something entirely their own. His band did not
just write and record an album - they built instruments by hand to give it a sound that could not be replicated.

But as the stakes grew, Dawson's drive for perfection became a need for control, placing enormous pressure on his closest relationships.

Then the band broke apart.

In this candid conversation, Dawson reveals what that rupture forced him to confront: the cost of ambition, the difference
between leading and controlling, and the difficult work of repairing relationships after trust has been fractured.
The journey takes us from a family home transformed into a recording studio to record-label realities, life on tour, a new calling
in mental health, renewed faith, and Dawson's eventual return to music - not as a vehicle for fame, but as a source of joy.

This is a conversation about music, family, accountability, and the difference between proving yourself and providing something
meaningful.

In this episode:
- The band breakup that blindsided Dawson
- When ambition begins costing you your family
- Building instruments by hand for the album Handmade
- The financial reality behind record deals and touring
- Repairing relationships through a list of twelve names
- Moving from band leader to mental-health professional
- Rediscovering faith, creativity, and joy
- Why great leadership requires meeting people where they are
- Learning to release control through collaboration

• (00:00) - Welcome and Meet Dawson Scholz
• (03:37) - The Band Breakup That Blindsided Him
• (04:55) - When Ambition Costs Family
• (07:31) - Repeating the Control Problem
• (10:20) - From Canada to North Idaho
• (13:50) - A Family That Spoke Music
• (16:10) - The House That Became a Studio
• (18:59) - Saloon: The First Album
• (23:29) - Handmade: Building Their Own Instruments
• (31:17) - The Cost of the Handmade Vision
• (34:49) - Signing Young and the Reality of Label Life
• (41:59) - Album Ownership and an Ongoing Musical Story
• (46:58) - From Chasing Fame to Finding Joy Again
• (53:10) - Parker’s Fish and the Value of a Private Moment
• (55:25) - Repairing Relationships: The List of Twelve Names
• (58:00) - From Band Leader to “Tour Therapist”
• (01:00:30) - Discovering a Calling in Mental Health
• (01:04:00) - When Ego Follows You Into Helping Work
• (01:06:47) - Faith Lost and Found
• (01:13:15) - Leaving Social Media Behind
• (01:14:44) - The Future of the Music
• (01:17:38) - Surrendering Control Through Collaboration
• (01:20:13) - What Makes a Great Leader
• (01:22:01) - The Challenge of Working with Family
• (01:23:26) - Closing Reflections

Full description

What happens when the excitement fades, confirmation doesn’t arrive, and the life you left behind is no longer waiting for you? What do you do in the silence between the decision you made and the outcome you hoped would follow?

In this deeply personal episode of The Prompt & The Leap, we explore four stages that can follow a life-changing decision: the morning after, the silence, the question “Was I wrong?”, and the second decision.

Through stories of love, relocation, isolation, illness, lost work, unexpected community, and even a few chickens, we examine the emotional space where doubt grows and identity begins to shift.  The first decision may take courage. The second often requires something deeper: the willingness to remain present when the path no longer feels certain.

In this episode
•      What the “morning after” a leap really feels like

•      Following a prompt that led to a life-changing relationship

•      Leaving a familiar life for Coeur d’Alene

•      When following the prompt doesn’t immediately produce bliss

•      The difference between giving up and surrendering

•      Losing a professional identity during forced silence

•      Feeling invisible, and learning to notice invisible people

•      Transactional relationships and the loneliness they leave behind

•      Why delayed confirmation is not proof that you were wrong

•      Practical ways to move through a quiet season

•      Choosing meaningful experiences over arbitrary objectives

•      Why making a second decision does not mean the first one failed

The space between the leap and the landing can feel empty. But silence is not always absence. Sometimes it is where a new life, identity, or understanding is quietly taking shape. The question isn’t only whether you were brave enough to leap. It’s whether you can trust yourself in the space that follows.

• (00:00) - Welcome and the Four Stages After a Leap
• (02:55) - What the “Morning After” Really Means
• (04:20) - The Prompt to Follow Roger into the Elevator
• (07:09) - Regret, Doubt, and the Second Decision
• (12:10) - The Leap to Coeur d’Alene
• (14:11) - When Following the Prompt Isn’t Bliss
• (20:36) - Isolation, Community, and the Cat Farmer
• (27:06) - Giving Up Versus Surrendering
• (30:24) - Why Twelve Years Can Feel Like Yesterday
• (32:27) - When the Noise and Busyness Disappear
• (35:29) - Forced Silence and the Loss of a Work Identity
• (38:18) - Feeling Invisible—and Learning to Notice Others
• (40:17) - Transactional Relationships and Loneliness
• (43:21) - Conviction, Delayed Reward, and Silence
• (44:54) - Practical Ways Through a Quiet Season
• (47:16) - Moments Over Time and Experiences Over Objectives
• (48:05) - Creating a Legacy Instead of Spectating
• (50:34) - Second Decisions Are Not Failure
• (52:33) - No Regrets—and Learning from Mistakes
• (55:21) - Closing Reflections

She had a resignation letter written. Then a Facebook post changed everything.

Dr. Jenna Silakoski was good at medicine. She just couldn’t stand what it had become.

She grew up in Appalachian poverty, earned her medical degree through the Army, and was running two clinics before most doctors finish their first year of practice. Then she hit a wall, and she was ready to walk away from it all.

What happened next involved a stranger online, a cross-country move with no safety net, and a decision her own husband said couldn’t be done. Within weeks, she was on a plane with her kids, her pets, and no plan B.

The leap was only the beginning. Somewhere along the way came a meeting with a bankruptcy attorney, some of the hardest decisions of her career, and a lesson with a seven-figure price tag. She’ll tell you what it was. She’ll also tell you what she wishes she had listened to sooner.

And somewhere in the middle of all of it is a laser, a group of teenagers, and a reason she keeps building.

Questions this episode answers

• What would make a successful doctor quit at 29?
• How does a first-time business owner get a bank to say yes?
• What does she refuse to become, no matter how big this gets?
• What finally carried her through when every door slammed shut?

Press play to find out what she chose.

• (00:00) - Meet Dr. Jenna Silakoski
• (03:38) - Leaving Assembly-Line Medicine
• (07:38) - Appalachia, Education, and the Army
• (16:14) - Leading Clinics and Choosing a New Path
• (27:45) - Near-Bankruptcy and Becoming a Business Owner
• (36:21) - Hard Decisions and the Peace That Followed
• (42:39) - Growing with Purpose and Defining Enough
• (46:49) - How Direct Primary Care Works
• (52:39) - Giving Back Through Day of Transformation
• (56:21) - Scaling Humanity Without Losing Your Why