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Artwork for What's Your Deal?

What's Your Deal? | Business Buying, Business Acquisitions, Investing & Exit Strategies

Matt Uhler
SBA Financing
Business Acquisition
Trauma
Real Estate
Entrepreneurship
Due Diligence
Small Business Acquisition
Buying a Business
Bitcoin
Franchising
Private Money Lending
Small Business Investing
Leadership
Family Bank
Employee Stock Ownership Plan
Nearshoring
Spyside Equity
Private Equity
Manufacturing
Exit Strategy

What's Your Deal? with Matt Uhler is a podcast for entrepreneurs, investors, and business owners looking to buy businesses, build multiple streams of income, and prepare for a profitable exit. Throughout the show, we break down real-world business deals, small business investing strategies, business financing—including SBA loans and owner financing—and exit planning, so you can make confident deci... more

PublishesWeeklyEpisodes73Founded2 years ago
Number of ListenersCategories
InvestingBusiness

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Artwork for What's Your Deal?

Latest Episodes

Nicole Hines joins Matt Uhler to share her journey buying a business without leaving the career she loves. She explains how she narrowed a wide-open buy box down to e-commerce and stationery, and why she walked away from a business that looked great ... more

YouTube

Matt Uhler sits down with Mike Grossman, author of Failure Is an Option and a veteran CEO of six venture-funded companies.

Mike explains how two failed attempts to take a company public led to an acquisition worth meaningfully more than the IPO. He... more

YouTube

Colleen Joyce, CEO of Lawyer.com, joins Matt Uhler to share how she built an eight-figure legal marketplace from a single room and a great domain name. She explains her "sell it, then build it" approach, why the team that gets you to $1 million usual... more

YouTube

For the first time on What's Your Deal, Matt Uhler sits down with a fellow business broker, Ryan Armstrong of Transworld Phoenix. He and Matt walk through the full life of a Main Street deal: preparing the seller emotionally, building a data-driven l... more

YouTube

Key Facts

Accepts Guests
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Acquisitions Anonymous - #1 for business buying, selling and operating
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Recent Guests

Nichole Hines
Corporate attorney and founder of Samira and Caleb
Samira and Caleb
Episode: Buying a Business While Keeping Your Career - Nichole Hines
Mike Grossman
Author of Failure Is an Option and veteran CEO of six venture-funded companies
Episode: Failure Is an Option: Lessons from 6 Venture-Funded CEO Roles - Mike Grossman
Colleen Joyce
CEO of Lawyer.com
Lawyer.com
Episode: Fast Failure, Real Growth: Lessons From Lawyer.com CEO - Colleen Joyce
Ryan Armstrong
Business broker and certified business intermediary who oversees Transworld Phoenix franchise in Arizona
Transworld Phoenix (Arizona)
Episode: Two Business Brokers Talk LOIs, Due Diligence & Deal Killers - Ryan Armstrong
Rich Hua
Former chief EQ evangelist at Amazon, CEO of Epic Leadership Group
Epic Leadership Group
Episode: Why Smart Leaders Fail: Emotional Intelligence Lessons from Amazon - Rich Hua
Ryan Beckmann
Serial entrepreneur; founder of Hero Picks and The Last Save; nonprofit advocate
Hero Picks; The Last Save
Episode: How Losing Everything Led to Success - Ryan Beckmann
Rodney Steidinger
Co-owner of ZebraScapes Landscaping, partner in the business
ZebraScapes Landscaping
Episode: Building a Business From Nothing (Literally) — Rodney Steidinger
Beau Bullard
Founder of Bullard Media; digital marketing strategist and content creator
Bullard Media
Episode: Why Most Business Owners Are Afraid of Social Media (And How to Fix It) - Beau Bullard
Nikhil Agharkar
Tax attorney, wealth advisor, owner of Crown Point Tax
Crown Point Tax
Episode: The Costco Write-Off Trap and How Bad Tax Advice Kills Your Business's Sale Price - Nik Agharkar

Host

Matt Uhler
Host of the show

Reviews

5.0 out of 5 stars from 25 ratings
  • Very informative & helpful podcast. Wealth of knowledge

    This podcast covers a wide variety of business topics and is very informative and helpful. Such a wealth of wisdom and knowledge. I highly recommend!

    Apple Podcasts
    5
    Denise Steid
    United States4 months ago
  • What every entrepreneur needs to know

    After listening to just a few episodes it’s clear that Matt’s experience and knowledge are a must have for any business owner or aspiring entrepreneur. Being in a similar space I’ve learned so much from these podcasts.

    Apple Podcasts
    5
    Ariz1758
    United States6 months ago
  • Invaluable information

    It’s a relief to hear from skilled and talented people on this topic. There are a lot of “experts” on social media that don’t seem to be very deep. but Matt and Sarah are inspiring, experienced, and real.

    Apple Podcasts
    5
    Dwdavistx
    United States2 years ago
  • Great education!

    Wonderful education if you are thinking about business acquisition, this is the place to be 🙌🏼

    Apple Podcasts
    5
    Iheartvfit
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Episodes are praised for depth over surface-level advice and real-world deal context.
Audience notes value the host and guests for actionable guidance in acquisitions and wealth-building.
Listener insights highlight the show as a practical, experience-based resource for buyers and sellers.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Buying a Business While Keeping Your Career - Nichole Hines
Q: Can you share a little bit about what you learned in the process of actually drilling into the numbers?
Hines describes an e-commerce prospect whose tax returns showed losses for three years despite the seller's claims about revenue and add-backs. The seller later revised the SDE downward by $40,000, while the low unit economics and complex earn-out structure made the deal no longer worth pursuing.
Buying a Business While Keeping Your Career - Nichole Hines
Q: Can you walk us through how your buy box evolved from being open to almost anything profitable to what you think would work?
Hines began considering nearly any profitable business, including options far from her location, but realized an acquisition needed to complement Samira and Caleb and fit her time limits. She narrowed her search to e-commerce, especially stationery and gift-related businesses.
Failure Is an Option: Lessons from 6 Venture-Funded CEO Roles - Mike Grossman
Q: How do you manage or how do you evaluate somebody's effectiveness with that many people that remote? How do you measure that?
Grossman says the company set specific objectives, strategies, tactics, and success metrics, then measured delivery against them using green or red status indicators. He emphasizes that clear processes helped coordinate a large distributed workforce.
Failure Is an Option: Lessons from 6 Venture-Funded CEO Roles - Mike Grossman
Q: Can you share an example of a failure that you had in your career, that just changed your trajectory and how that influenced you in a way that was positive?
Grossman recounts two unsuccessful efforts to take a company public, the first interrupted by COVID and the second abandoned when the terms no longer made sense. The failure ultimately preceded an acquisition for more than the company might have received through an IPO.
Fast Failure, Real Growth: Lessons From Lawyer.com CEO - Colleen Joyce
Q: Can you share a fast-failure example and what you learned from it?
The live events experiment initially lost money but eventually became a profitable annual conference, showing how early failures can reinforce brand and create long-term revenue opportunities.

Audience Metrics

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

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About What's Your Deal?

What is What's Your Deal? about and what kind of topics does it cover?

This show centers on practical, real-world strategies for buying, financing, and exiting small to mid-market businesses. Episodes consistently explore how to find suitable acquisitions, structure deals, secure financing (including SBA loans and seller financing), and plan exits to maximize long-term wealth. A running thread is the emphasis on disciplined due diligence, cash-flow optimization, and governance, with guests ranging from tax and wealth-planning experts to private equity operators and successful buyer-sellers. A notable strength is the host's hands-on approach to equity-based ownership and multi-deal portfolios, which provides a distinctive lens for listeners aiming to build diversified business portfolios or prepare for exits. T... more

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Which podcasts are similar to What's Your Deal??

These podcasts share a similar audience with What's Your Deal?:

1. BigDeal
2. THE ED MYLETT SHOW
3. Acquiring Minds
4. BiggerPockets Money
5. Acquisitions Anonymous - #1 for business buying, selling and operating

How many episodes of What's Your Deal? are there?

What's Your Deal? launched 2 years ago and published 73 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on What's Your Deal??

Recent guests on What's Your Deal? include:

1. Nichole Hines
2. Mike Grossman
3. Colleen Joyce
4. Ryan Armstrong
5. Rich Hua
6. Ryan Beckmann
7. Rodney Steidinger
8. Beau Bullard

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