Business

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

by Matt Uhler

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Latest daily rankings: Oct 21. New rankings will appear after the next update.

Recent history only — this show has no current ranking on the Business, Canada chart. These are recorded positions from the last 7 days, not current rankings.

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Date	Combined Rank	Apple Podcasts
Oct 21	—	—
Oct 20	#188	#188

Latest episodes

Failure Is an Option: Lessons from 6 Venture-Funded CEO Roles - Mike Grossman

October 21, 2026 · 46 min

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…
Fast Failure, Real Growth: Lessons From Lawyer.com CEO - Colleen Joyce

October 14, 2026 · 42 min

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…
Two Business Brokers Talk LOIs, Due Diligence & Deal Killers - Ryan Armstrong

October 7, 2026 · 45 min

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…
Why Smart Leaders Fail: Emotional Intelligence Lessons from Amazon - Rich Hua

September 30, 2026 · 38 min

Why do brilliant people sometimes make terrible decisions? According to Rich Hua, former Chief EQ Evangelist at Amazon, it's because stress can cut your effective IQ in half, and most leaders were never taught how to manage it. In this…
How Losing Everything Led to Success - Ryan Beckmann

September 23, 2026 · 52 min

Ryan Beckmann built and lost multi-million-dollar RV dealerships, won a 40 Under 40 award the same year he became homeless, and fought his way back from addiction to found Hero Picks and The Last Save. In this raw conversation, Ryan shares…

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Building a Business From Nothing (Literally) — Rodney Steidinger

September 16, 2026 · 45 min

Matt sits down with longtime friend and ZebraScapes Landscaping founder Rodney Steidinger, who built his company from a minivan and a trailer during the 2008 recession into a thriving, multi-generational business. Rodney shares the…
Why Most Business Owners Are Afraid of Social Media (And How to Fix It) - Beau Bullard

September 9, 2026 · 43 min

Most business owners over 40 have never posted on social media — and it's not because they don't know how. It's fear. Matt Uhler sits down with Beau Bullard, founder of Bullard Media, to unpack why attention is today's most valuable…
The Costco Write-Off Trap and How Bad Tax Advice Kills Your Business's Sale Price - Nik Agharkar

September 1, 2026 · 43 min

Tax attorney and wealth advisor Nik Agharkar of Crown Point Tax joins Matt to unpack the difference between tax evasion, tax deferral, and legitimate tax strategy — and why so many business owners unknowingly torch their company's sale…
Know Your Number: Exit Planning Secrets - Anthony Perez

August 26, 2026 · 41 min

Most business owners spend decades building their company but almost no time planning what happens after they sell it. In this episode, Matt sits down with Anthony Perez of Harvest Wealth Strategies to talk about "knowing your number," why…
Buying a Business 101: A First-Time Buyer Asks Matt Everything

August 17, 2026 · 51 min

This week's episode flips the script — Beau Bullard, who's never bought a business himself, turns the tables and interviews Matt with the exact questions first-time buyers ask most. They cover finding your core competency, why profitable…
What Private Equity Looks For in a Deal - Eric Wiklendt

August 10, 2026 · 44 min

Eric Wiklendt, Managing Director of SpySide Equity, joins Matt Uhler to break down how private equity firms evaluate, acquire, and transform manufacturing businesses. Eric shares the "fix and build" framework his firm uses to grow…
Nearshoring Explained: How to Build Remote Teams - Brian Samson

August 5, 2026 · 40 min

Nearshoring is reshaping how U.S. companies build teams — and Brian Samson, founder of Plugg Technologies, has spent over a decade helping businesses do it right. In this episode of What's Your Deal, Brian joins Matt Uhler to break down…

Full episode archive on Apple Podcasts →

About the show

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 decisions, reduce risk, and build long-term wealth through small business ownership. From first-time buyers to experienced investors, we cover how to find the right business to buy, structure deals, secure financing, grow cash flow, and position your business exit. If you're serious about buying a business, investing in small businesses, scaling income, and creating financial freedom through ownership and exits, this podcast is for you. New episodes weekly. Subscribe and start building your path to business ownership and long-term wealth.