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Personal Bets

Chance Sweat
Entrepreneurship
H&H Products
Stock Market
Real Estate
Lakeridge Winery
Mental Health
Hartley Family
EOS
Leadership
Central Florida
Shackleton
Ocala
Immigration Law
Google
Mortgage
Private Equity
Home Services
E2 Visa
EXP Realty
Bible Study

Small and Medium Businesses are the backbone of America. I interview those that chose to bet on themselves, and America is better because of them.

PublishesWeeklyEpisodes10Founded2 months ago
Number of ListenersCategories
EntrepreneurshipBusiness

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Latest Episodes

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We pull a thread through three standout stories and lay out the hidden work that happens before a big risk pays off. We argue that smart bets come from pre-framing reality, auditing your own fear, and validating with real-world test... more

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We sit down at Lakeridge Winery over a bold Napa Valley Cabernet and trace how a backyard vineyard experiment turns into one of Florida’s biggest wine operations. We talk candidly about leadership pressure, long-tenured teams, and t... more

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We talk about why “fewer better deals” beats chasing every opportunity, especially as AI makes it easier to move fast without real alignment. We trace Brody's path from early entrepreneurship at home through a startup exit and into ... more

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Today we talk with a new friend, Bobby Davidowitz. Who started his career as a Publix Bag Boy, but pivoted to Real Estate in the early 2000's. Navigated the great financial crisis and is currently building the first of its kind, Cul... more

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We sit down with Justin to trace the long road from sweaty manual labor to building a life where he does not depend on anyone else to sign his paycheck. Along the way we talk about big bets, bad bets, and the mindset shifts that tur... more

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One medical test can erase a “sure thing” career plan. Jorge thought he was on track for federal law enforcement until a color vision deficiency ended the process overnight, forcing a hard reset and a new question: now what?

Jorge ... more

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Today we talk to a mentor of mine, amazing business broker, and Shackleton enthusiast, Shaun Thornton - Business Broker with FitzGibbon Alexander Inc.

Shackleton’s ship gets crushed by Antarctic ice, his crew ends up stranded, and... more

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A lot of people think therapy is just great conversations in a calm room. 

The truth is, being a counselor is also running a business, carrying other people’s pain with care, and then walking back into family life like you didn’t j... more

Key Facts

Accepts Guests
Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

Recent Guests

Justin Maxwell
Mr. Money Maxwell, investor discussing Covid Spy bet
Personal connections
Episode: Chance Sweat: The Bet Before The Bet
Bobby Davidowitz
Commercial broker and business owner discussing early career pivots
Alliance at EXP
Episode: Chance Sweat: The Bet Before The Bet
Christian Slupe
CEO/Executive overseeing Lakeridge Winery operations and San Sebastian collaboration
Lakeridge Winery
Episode: Christian Slupe: From The Ledgers To The Cellar, Lakeridge Winery
Brody Vinson
Entrepreneur focused on micro private equity and Scale for Sale
Scale for Sale (co-founder)
Episode: Brody Vinson: Business Is "My Pleasure," From Chick-fil-A To LOI's
Jorge Sevilla
Attorney specializing in business and immigration law
Ocala Equine ESQ (formerly Sevilla Law)
Episode: Jorge Sevilla: When The FBI Said No And The Bar Said Yes
Shaun Thornton
Business broker and host of Happy Buyer Happy Seller
FitzGibbon Alexander (former colleague/team)
Episode: Shaun Thornton - Shackleton, Steel, and Proof of Funds
Keenan Crowley
Therapist and counselor who shifted from youth ministry to private practice
Private counseling practice in Central Florida
Episode: Keenan Crowley - Therapy As A Business
John King
Founder-CEO of an EOS/leadership coaching practice, former worship pastor and producer, with a background in music technology startups
Episode: John King: From Music Startups To EOS Leadership Coaching
Jimmy Hartley
VP of Operations and third-generation Hartley, leader at H&H Products
H&H Products
Episode: H&H Products - The production of a culture

Host

Chance Sweat
Host of Personal Bets; affiliated with FitzGibbon Alexander / Foundry Leadership

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The Money Mondays
The Money MondaysDan Fleyshman
Creating Confidence with Heather Monahan
Creating Confidence with Heather MonahanHeather Monahan | YAP Media

Talking Points

Recent interactions between the hosts and their guests.

Brody Vinson: Business Is "My Pleasure," From Chick-fil-A To LOI's
Q: How did your early experiences shape your view on risk and entrepreneurship?
Early jobs and family business exposure taught him to value hard work, practical skills, and the importance of choosing the right partners and business models over chasing rapid, flashy growth.
Bobby Davidowitz: Building Wealth Beyond Money, From Bag Boy to CEO
Q: How did you enter real estate and mortgages and pivot to building culture around business?
He shares the sequence from mortgage lending to real estate investing, meeting a broker who invited him to join a culture-focused firm, and ultimately launching a Culture Center Program to fund spaces and build community.
Bobby Davidowitz: Building Wealth Beyond Money, From Bag Boy to CEO
Q: When did you start seeing yourself as an entrepreneur?
He describes entrepreneurship as a path followed over 25 years, often within structured systems, and emphasizes that wealth is multi-dimensional rather than purely monetary.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
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Frequently Asked Questions About Personal Bets

What is Personal Bets about and what kind of topics does it cover?

This show centers on pragmatic entrepreneurship and self-bet stories, with episodes that mine real-world risk, validation, and growth through hands-on experiences. Across interviews, listeners hear how founders and operators navigate uncertainty, test ideas before committing, and scale through disciplined patterns—ranging from private-equity pivots and culture-driven real estate to family-led manufacturing and leadership coaching. Noteworthy is a penchant for concrete lessons, personal anecdotes, and a bias toward practical strategies (pre-framing, stress-testing, governance, and culture) that listeners can adapt to their own ventures. The guest mix tends to prioritize operators who built, scaled, or transformed small- to mid-size businesse... more

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To see how many followers or subscribers Personal Bets has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

How many episodes of Personal Bets are there?

Personal Bets launched 2 months ago and published 10 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Personal Bets?

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What guests have appeared on Personal Bets?

Recent guests on Personal Bets include:

1. Justin Maxwell
2. Bobby Davidowitz
3. Christian Slupe
4. Brody Vinson
5. Jorge Sevilla
6. Shaun Thornton
7. Keenan Crowley
8. John King

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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