Caleb Stapp never planned to become a financial advisor. As a worship and youth pastor making $30,000 a year with three kids and a fourth on the way, he had no path to homeownership and no way forward. When someone suggested he'd be good at financial planning, he told them it sounded terrible.
But sometimes the paths we resist are exactly where we need to go.

In this conversation, Caleb walks through his journey from ministry to financial services, and eventually to building his own independent practice. He talks about the identity crisis of leaving pastoral work, the strange relief of doubling his income overnight, and the devastation of being let go from a big firm just as he'd gotten comfortable.

What makes Caleb's story compelling is his honesty about the hard parts. The first six months of going solo where he didn't pay himself at all. The year it took to work through the emotional weight of being fired. The constant tension between wanting to create new things and needing to operate a functional business.

He also talks about something many solopreneurs struggle with: how to introduce yourself when your work is more than just a title. Caleb identifies as a shepherd, someone designed to care for and lead groups, but that doesn't fit neatly into networking conversations. So he's learned to start small, state what he does clearly, and then exceed expectations rather than making big promises upfront.

This episode is for anyone navigating an unexpected career transition, anyone building something solo while raising a family, or anyone trying to figure out how to stay focused when the entrepreneurial urge pulls in every direction.

Key things you'll hear in this episode:
Why Caleb initially resisted becoming a financial advisor even though someone close to him saw it clearly
How his income doubled overnight when he left ministry and what that shift meant for his family
The identity crisis of wondering if God had rejected him when pastoral work didn't work out
What it was like to go through a four to five month application process for a job he didn't think he wanted
How being let go from a big firm in 2024 forced him into independence sooner than planned
The first six months of not paying himself and relying on government assistance and savings to survive
Why it took a full year to emotionally process being fired and what finally shifted
The tension between being an entrepreneur who loves creating new things and an operator who needs systems
How he's building a practice capped at 100 clients with a focus on the right people, not explosive growth
Why he introduces himself as a financial advisor upfront even though it sometimes creates hesitation
His belief that pivots, however devastating in the moment, can turn out for the best in the long run

If you're looking for clarity on your finances or want to save money on taxes, Caleb is offering listeners a free 30-minute call that includes a tax return review and a blueprint of your finances. Visit his LinkedIn profile to book.

Connect with Caleb Stapp:
LinkedIn: https://www.linkedin.com/in/calebstapp/

I hope you enjoy this episode!
Give it a like, share, and subscribe to not miss the content coming your way weekly.
– Moe and the Team of One podcast team

Connect with Moe on LinkedIn: https://www.linkedin.com/in/moechoice/
Learn the exact framework LIVE here: https://www.moechoice.net/masterclass/

Listen to Team of One on these podcast platforms:
Spotify: https://open.spotify.com/show/0G9lhUs4mgFAKCJPWVJnsD
Apple Podcasts: https://podcasts.apple.com/us/podcast/team-of-one/id1833209937
Amazon Podcasts: https://music.amazon.com/podca

#solopreneurship #teamofone #moechoice #businesscoaching #soloentrepreneur #thoughtleadership #businessframeworks #resilience #contentcreation #personaldevelopment
Team of One, hosted by serial solopreneur and executive coach Moe Choice, dives into the real-world challenges, strategies, and mindset shifts necessary to succeed as a one-person business. Each episode features in-depth conversations with solo entrepreneurs, content creators, solopreneur leaders, and thought professionals navigating marketing, resilience, frameworks for growth, and sustainable business design. Whether you're launching your own consultancy, building content platforms, balancing creativity with income, or aspiring to become a thought leader, this podcast delivers practical insights, frameworks, and inspiring stories to help you thrive as a solo founder.

Are you navigating the challenging transition from corporate life to successful self-employment?

Join host Moe Choice on Team of One as he speaks with Tom Schin, owner of Build Better Culture, about his honest and powerful journey as a solopreneur. Tom shares the raw reality of leaving a corporate career to become a "one-stop shop," handling every aspect of his own business.

This episode is packed with lessons on personal growth, the necessity of setting clear goals, and the unexpected intensity of business challenges during the tough first year. Learn how Tom overcame significant self-doubt, utilized his support system, and developed the persistence needed to chase his aspirations in the speaking engagements and book writing arenas.

🔑 Key Takeaways You'll Get:
The essential difference between having a side hustle and committing fully to solopreneurship.

How to handle the self-doubt that arises when you don't hit your initial goals.

Why strong support systems (family and friends) are non-negotiable for self-employment success.

Tom's strategy for adapting and maintaining persistence when facing rejection and struggles.

Insights into making the strategic career transition from a stable job to owning your path.

How writing a book can serve as a powerful tool to expand your professional opportunities in the speaking circuit.

Press play if you're ready to embrace the ups, downs, and ultimate rewards of being a team of one!

Connect with Tom here:
On LinkedIn: https://www.linkedin.com/in/schinnn/
Company website: Www.buildbetterculture.com
Tom's podcast: Https://wrkdefined.com/podcast/this-meeting-should-have-been-a-podcast

I hope you enjoy this episode!
Give it a like, share, and subscribe to not miss the content coming your way weekly.
– Moe and the Team of One podcast team

Connect with Moe on LinkedIn: https://www.linkedin.com/in/moechoice/
Learn the exact framework LIVE here: https://www.moechoice.net/masterclass/

Listen to Team of One on these podcast platforms:
Spotify: https://open.spotify.com/show/0G9lhUs4mgFAKCJPWVJnsD
Apple Podcasts: https://podcasts.apple.com/us/podcast/team-of-one/id1833209937
Amazon Podcasts: https://music.amazon.com/podca

#solopreneurship #teamofone #moechoice #businesscoaching #soloentrepreneur #thoughtleadership #businessframeworks #resilience #contentcreation #personaldevelopment
Team of One, hosted by serial solopreneur and executive coach Moe Choice, dives into the real-world challenges, strategies, and mindset shifts necessary to succeed as a one-person business. Each episode features in-depth conversations with solo entrepreneurs, content creators, solopreneur leaders, and thought professionals navigating marketing, resilience, frameworks for growth, and sustainable business design. Whether you're launching your own consultancy, building content platforms, balancing creativity with income, or aspiring to become a thought leader, this podcast delivers practical insights, frameworks, and inspiring stories to help you thrive as a solo founder.

Are you navigating the challenging transition from corporate life to successful self-employment?

Join host Moe Choice on Team of One as he speaks with Tom Schin, owner of Build Better Culture, about his honest and powerful journey as a solopreneur. Tom shares the raw reality of leaving a corporate career to become a "one-stop shop," handling every aspect of his own business.

This episode is packed with lessons on personal growth, the necessity of setting clear goals, and the unexpected intensity of business challenges during the tough first year. Learn how Tom overcame significant self-doubt, utilized his support system, and developed the persistence needed to chase his aspirations in the speaking engagements and book writing arenas.

🔑 Key Takeaways You'll Get:
The essential difference between having a side hustle and committing fully to solopreneurship.

How to handle the self-doubt that arises when you don't hit your initial goals.

Why strong support systems (family and friends) are non-negotiable for self-employment success.

Tom's strategy for adapting and maintaining persistence when facing rejection and struggles.

Insights into making the strategic career transition from a stable job to owning your path.

How writing a book can serve as a powerful tool to expand your professional opportunities in the speaking circuit.

Press play if you're ready to embrace the ups, downs, and ultimate rewards of being a team of one!

Connect with Tom here:
On LinkedIn: https://www.linkedin.com/in/schinnn/
Company website: Www.buildbetterculture.com
Tom's podcast: Https://wrkdefined.com/podcast/this-meeting-should-have-been-a-podcast

I hope you enjoy this episode!
Give it a like, share, and subscribe to not miss the content coming your way weekly.
– Moe and the Team of One podcast team

Connect with Moe on LinkedIn: https://www.linkedin.com/in/moechoice/
Learn the exact framework LIVE here: https://www.moechoice.net/masterclass/

Listen to Team of One on these podcast platforms:
Spotify: https://open.spotify.com/show/0G9lhUs4mgFAKCJPWVJnsD
Apple Podcasts: https://podcasts.apple.com/us/podcast/team-of-one/id1833209937
Amazon Podcasts: https://music.amazon.com/podca

#solopreneurship #teamofone #moechoice #businesscoaching #soloentrepreneur #thoughtleadership #businessframeworks #resilience #contentcreation #personaldevelopment
Team of One, hosted by serial solopreneur and executive coach Moe Choice, dives into the real-world challenges, strategies, and mindset shifts necessary to succeed as a one-person business. Each episode features in-depth conversations with solo entrepreneurs, content creators, solopreneur leaders, and thought professionals navigating marketing, resilience, frameworks for growth, and sustainable business design. Whether you're launching your own consultancy, building content platforms, balancing creativity with income, or aspiring to become a thought leader, this podcast delivers practical insights, frameworks, and inspiring stories to help you thrive as a solo founder.