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

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 covers why you should focus on inputs instead of outcomes and the danger of chasing adjacent opportunities. He also explains when it's worth defying your board, why spending discipline matters, and how a fully remote team of 300+ changed his view on recruiting. Connect with Mike Grossman: Book: Failure Is an Option, available on Amazon, Barnes & Noble. Website: failureisanoption.com https://www.instagram.com/failureisanoptionbook Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to:…

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 usually isn't the team that gets you to $20 million, and how a money-losing live events experiment became a profitable annual conference. Colleen and Matt also dig into fast failure, learning to delegate, and what AI really means for lawyers and the people who need them. Connect with Colleen Joyce: lawyer.com lawyergrowthsummit.com https://www.facebook.com/lawyerdotcom https://www.linkedin.com/in/colleenjoyce/ https://www.linkedin.com/newsletters/fast-five-tuesdays-7265815097552326656/ Instagram: @lawyerdotcom Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's…

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 listing, and vetting buyers. They also cover LOIs, due diligence, financing and closing, and why the best deals leave buyer and seller as friends. Connect with Ryan Armstrong: https://www.tworld.com/agents/ryanarmstrong Phone: 480-447-3504 Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people…

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 episode of What's Your Deal, host Matt Uhler sits down with Rich to talk about emotional intelligence and why it may be the most underrated skill in business today. Rich grew up focused almost entirely on IQ: straight A's, a perfect SAT score, and engineering at UC Berkeley. He calls it his "genius robot" plan, and it worked well until he got married and realized something important was missing. That realization launched a lifelong study of EQ. At Amazon, he wrote the six-pager that created his own role and built a 70,000-person community. He ultimately helped bring EQ to more than 1.5 million people inside Amazon and across leading companies worldwide. Connect with Rich Hua: LinkedIn: linkedin.com/in/richhua Email: rich@richardhua.co Connect with Matt Uhler / Amped Success:…

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 what it took to hit bottom, why service to others became the key to his own healing, and how he's now building "Beyond Awareness" — a platform designed to connect survivors of trauma and abuse directly to real-time resources and sustainable funding. Connect with Ryan Beckmann: https://www.linkedin.com/in/ryan-beckmann-heropicks/ https://www.instagram.com/ryanfbeckmann/ Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple…

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 breaking point that forced him to hire real leadership, how he built a family business empire with his three daughters, and the core values that guide every hire and promotion at ZebraScapes. Connect with Rodney Steidinger: https://zebrascapes.com https://www.instagram.com/zebrascapes/ Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a…

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 currency, why iPhone content outperforms professional cameras by up to 800%, and how business owners (and the buyers who acquire their companies) should think about personal brand, legacy, and authenticity on social media. Connect with Beau Bullard: https://bullardmedia.org/ https://www.instagram.com/beaubullardaz Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed…

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 value with aggressive write-offs. They dig into the "Costco conversation," why most CPAs aren't equipped to strategize (only to prepare). A must-listen for anyone planning to sell a business — or just tired of overpaying Uncle Sam. Connect with Nik Agharkar: https://www.crownepointtax.com Social media https://www.instagram.com/nikagharkar/ https://www.instagram.com/crownepoint_tax/ https://www.linkedin.com/in/nikagharkar/ Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen &…

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 owner dependency is the #1 deal killer, and how to turn business equity into lasting personal and generational wealth — before it's too late to plan. Connect with Anthony Perez: Phone: 619-241-6336 Email: anthony.perez@harvestwealthstrategy.com Social media @harvestwealthstrategies - Instagram @harvestwealthstrategies - YouTube www.linkedin/in/anthonyperezj Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify,…

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 businesses go up for sale, how valuations really work, SBA loan qualification, seller-carried notes, blue sky, employee retention, and what actually makes a Main Street business tick. If you're buying — or selling — this is the FAQ episode you need. Connect with Beau Bullard: www.bullardmedia.org https://www.instagram.com/beaubullardaz/ Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen…

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 EBITDA and scale revenue, how they handle underperforming key employees, why smaller businesses struggle to execute transformation, and what a five-to-seven-year hold period means for deal strategy. A must-listen for anyone curious how PE thinking differs from Main Street business ownership. Connect with Eric Wiklendt: https://speysideequity.com/team/eric/ https://www.linkedin.com/in/ericwiklendt Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to…

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 why nearshoring has become a go-to strategy for outsourced talent. Brian shares firsthand experience building an 80-person remote team from the ground up, the real cost breakdown between hiring domestically versus nearshoring, and how his company handles everything from sourcing and vetting to compliance and IP protection — while stepping back so clients build direct relationships with their hires. Whether you're a small business owner considering your first remote hire or scaling a larger team, this conversation offers a practical, no-nonsense look at how nearshoring works — and whether it's the right move for your business. Connect with Brian Samson: https://plugg.tech Linkedin - https://www.linkedin.com/in/briansamson/ Connect with Matt Uhler / Amped Success: Instagram:…

In this special episode, Sarah turns the tables and interviews Matt about an exciting new project: a community built for anyone thinking about buying a business. This new space opens the door for the masses to get questions answered live, weekly, with everything archived and searchable. Buying a business doesn't have to be guesswork. Get direct access to a business broker with nearly 30 years of experience in The Dealmakers Hub! This is a community built for people actively exploring business acquisition. Inside you'll get: Weekly live Q&A calls with me (Matt Uhler) Exclusive self-guided course "Don't Just Buy a Business, Buy the RIGHT Business" Real-world acquisition insights A growing library of call recordings Most of all… COMMUNITY! Learn alongside other buyers, ask your questions, and see what's actually working. As part of our inner circle, you get 7 days completely free. Please note that to reserve your spot you'll enter your payment info, but you won't be charged a thing until the trial ends. Cancel…

Eben and Ali Hartzenberg arrived in America with nothing, started from scratch, and built a portfolio of nine retail businesses. In this episode, they open up about facing fear, the power of data over intuition, what makes their marriage-meets-business-partnership work, and the red flags that tell them to walk away from a deal. Connect with Ali and Eben Hartzenberg: Ali@bennali.com Eben@bennali.com Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people discover the show.

Most business owners exploring an exit only hear one pitch: sell to private equity or a strategic buyer. Matt Middendorp, Director of ESOP Consulting at VisionPoint Capital, joins the show to make the case for a third path — selling to your own employees. Matt breaks down what an Employee Stock Ownership Plan (ESOP) actually is, the biggest misconceptions owners have about price, control, and legacy, and why ESOP companies often outperform their non-ESOP peers on growth, retention, and productivity. We get into eligibility rules, vesting, valuation, timelines, and one of the most overlooked ESOP tax benefits — one that can mean a tax-free exit for the right seller. If you're a business owner weighing your exit options, or just curious how employee ownership actually works in practice, this episode lays it out in plain terms. Connect with Matt Middendorp: www.esopready.com matt.middendorp@visionpointcapital.com 715.897.0879 Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website:…

Most business owners think they're making rational decisions. Robin Afinowich says otherwise. In this episode, Matt sits down with Robin Afinowich — a clinically trained mental health counselor, national speaker, and daughter of M&A legend Jim Afinowich — to unpack how unresolved stress and trauma quietly shape the decisions business owners make every day. From childhood adversity to burnout in leadership, Robin breaks down the science behind why high performers overwork, over-please, and struggle to stay present — and what to do about it. You'll learn why the "fawn" response is the most common (and most dangerous) pattern among executives, why stress and trauma leave the same physical fingerprint on the brain, and why the body always tells the truth even when the mind is "holding it together." This isn't a therapy session — it's a practical look at the inner drivers behind outer success, and why ignoring them eventually costs founders their health, relationships, and joy. Connect with Robin Afinowich:…

What actually creates lasting wealth? And why do so many entrepreneurs hit a ceiling despite working harder than ever? In this episode of What's Your Deal?, Matt Uhler sits down with entrepreneur, investor, and marketing strategist Alexa D'Agostino to discuss the uncomfortable truths behind scaling a business, building wealth, and transitioning from founder to owner. Alexa has built and exited multiple companies, helped generate billions in revenue, and created the exclusive Wealth Mastery Summit, where high-level entrepreneurs, investors, and operators gather to solve real business challenges. Together they explore why wealth isn't built through one lucky break, how founders unknowingly become the biggest bottleneck in their businesses, why finding the right "Number Two" is critical for growth, and how successful entrepreneurs know when to pivot instead of stubbornly pushing forward. If you're building a business—or planning to acquire one—this conversation will challenge the way you think about leadership,…

Most business owners spend years building income through their business, but far fewer create a strategy to turn that income into lasting wealth. In this episode of What's Your Deal?, Matt Uhler sits down with wealth advisor Ted Young of Anasazi Investment Group to discuss the financial decisions that can make or break a business owner's future. Ted shares the biggest mistakes he sees entrepreneurs make, why diversification matters, how to prepare for a successful exit, and what it really means to become "work optional." The conversation also explores retirement planning, investment strategies, tax considerations, market volatility, and the emotional challenges many owners face after selling their businesses. Whether you're actively growing a company, preparing for an exit, or simply trying to make smarter financial decisions, this episode provides practical insights on building wealth that lasts. Connect with Ted Young: Anasaziinvestmentgroup.com Ted.young@raymondjames.com 602-953-8802 Connect with Matt…

What happens when one of the most influential financial educators of all time sits down to talk business, investing, and the mindset behind wealth creation? In this episode of What's Your Deal?, Matt Uhler welcomes Robert Kiyosaki, author of Rich Dad Poor Dad and founder of the Rich Dad brand. With more than 40 million books sold worldwide, Robert has spent decades challenging conventional financial wisdom and encouraging people to think differently about money, investing, debt, and entrepreneurship. Robert shares the lessons he learned from having both a "rich dad" and a "poor dad," why rejection is a necessary part of success, and how developing entrepreneurial thinking can change the trajectory of your life. He discusses the importance of financial education, the difference between consumer debt and income-producing debt, and why he believes understanding cash flow is one of the most valuable skills anyone can learn. Connect with Robert Kiyosaki Website: RichDad.com Instagram: @therealkiyosaki X:…

What if you could build multiple streams of income through ownership in small businesses — without running every business yourself? In this solo episode of What's Your Deal?, Matt Uhler breaks down the exact framework he used to build ownership interests in more than 20 businesses across multiple industries through strategic equity deals and partnerships. If you are interested in learning more about the Multiple Streams of Income Framework please email - admin@ampedsuccess.com Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people discover…

What if the biggest threat to your business isn't competition, the economy, or a bad deal—but your own operating system? In this episode of What's Your Deal?, Matt and Audrey Uhler sit down with performance strategist and executive coach MJ Gordon to discuss why so many high-performing entrepreneurs feel overwhelmed, exhausted, and stuck in a constant state of stress. MJ has worked with leaders from organizations like Adidas, the NFL, and NerdWallet, helping them improve performance without sacrificing their health, relationships, or quality of life. Together, they explore the hidden costs of operating in perpetual fight-or-flight mode, the impact of cognitive overload, how ADHD and brain wiring affect entrepreneurs, and why recovery may be the missing ingredient in sustainable business growth. Whether you're building your first business, managing multiple companies, or simply trying to keep up with life's demands, this conversation offers practical strategies for creating more capacity, clarity, and…

What does it really take to build a successful life without sacrificing your health, family, happiness, or purpose along the way? In this episode of What's Your Deal?, Matt Uhler sits down with legendary entrepreneur and speaker David Meltzer for one of the most powerful conversations we've had on the show. David shares the lessons he learned after losing over $100 million, rebuilding his life through faith and purpose, and dedicating his mission to empowering over 1 billion people to be happy. Connect with David Meltzer Instagram: @davidmeltzer LinkedIn: David Meltzer YouTube: @DavidMeltzer Podcast: The Playbook Podcast Connect with Matt Uhler / Amped Success: Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/ Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com Listen & Subscribe: Be sure to subscribe…

In this episode of What's Your Deal?, Matt sits down with longtime business partner Kristian Gose and private lending veteran Bill "Billy A" Anastopoulos for an inside look at the world of private money lending, hard money loans, fix-and-flip financing, bridge loans, and real estate investing. With more than 80 years of combined experience and thousands of funded transactions between them, this conversation dives deep into how private lending actually works behind the scenes — from funding deals in as little as 48 hours to evaluating risk, protecting investors, and helping borrowers capitalize on opportunities traditional banks simply can't move fast enough to support. Timestamps: 00:17 – Introduction 02:51 – 80 Years of Combined Lending Experience 04:44 – Lessons from Entrepreneurship & Starting Over 06:39 – How the 2008 Crash Changed Lending 08:02 – What Is Hard Money Lending? 08:59 – Why Private Money Can Be Better Than a Partner 10:17 – Why Investors Pay for Speed 12:01 – How Fast Closings Win Real…

In this episode of What's Your Deal?, Matt sits down with Lindsey Quinn, founder of HeartWise Collective to talk about one of the biggest shifts happening in business today: artificial intelligence. Lindsey shares how she went from running a traditional consulting business in the orthodontic industry to building AI-powered systems that help business owners save time, improve efficiency, and create better workflows without adding more staff or burning themselves out. Matt and Lindsey break down how small business owners can start using AI in practical ways, from creating branded content and marketing systems to analyzing financial data, improving sales conversations, building SOPs, and reducing repetitive computer-based tasks. Lindsey also explains the difference between basic generative AI and more advanced AI agents, while keeping the conversation grounded for business owners who may feel overwhelmed by the technology. Timestamps 01:30 — How Lindsey pivoted from consulting into AI systems 04:00 — Lindsey's…

What does it really take to get approved for an SBA loan when buying a business? In this episode of What's Your Deal? with Matt Uhler, Matt sits down with SBA lending expert Steve Johnston and financing specialist Lindsay Denton to break down the truth about SBA loans, business acquisition financing, and why most buyers get it wrong. If you've heard horror stories about SBA loans taking forever—or getting declined at the last minute—this episode will completely change your perspective. They cover what lenders are actually looking for, how deals get approved (or denied), and why the story behind the deal matters just as much as the numbers. Whether you're a first-time buyer or an experienced investor, this conversation will help you avoid costly mistakes and position yourself to get funded the right way. Timestamps: 00:16 – Meet Steve Johnson & Lindsay Denton 03:14 – Why SBA loans get a bad reputation 04:20 – The biggest misconceptions about SBA lending 05:00 – How long SBA loans actually take (real…

What does it take to build a business that scales beyond you? In this episode of What's Your Deal?, Matt sits down with franchising expert and entrepreneur Jeff Dudan to unpack what makes franchise ownership work, how to scale a business through systems, and why great businesses are built with the end in mind. Jeff shares how he built and scaled AdvantaClean to over 240 locations before a successful exit, and how he now helps franchise brands grow through HomeFront Brands. Timestamps: 1:16 Jeff Dudan's Entrepreneurial Journey Begins 4:42 Building AdvantaClean from Startup to National Brand 7:50 The Inflection Point That Led to Franchising 12:42 Partnership Lessons Every Business Owner Should Know 17:55 Choosing the Right Partners and Avoiding Common Mistakes 19:38 How to Scale a Business Into a Franchise Model 24:23 Reverse Engineering Growth and Building for Outcomes 29:24 Territory Strategy, Resales & Creating Franchise Value 33:35 How to Evaluate a Franchise Opportunity Before You Buy 36:05 Why Skills,…

What happens when a key employee becomes one of the most valuable partners in a small business? In this episode of What's Your Deal?, Matt Uhler sits down with longtime business partner Ryan Carr to discuss small business ownership, business partnerships, leadership, entrepreneurship, company culture, employee management, and business growth. Ryan shares his journey from employee to owner after starting with a Northern Arizona commercial property maintenance company in 2016 and becoming a business partner in 2018. Today, he helps lead one of the top commercial property maintenance companies in Arizona, providing parking lot sweeping, pressure washing, fleet washing, portering services, snow removal, and exterior maintenance services. Timestamps: 01:35 - How the business sale and partnership came together 04:25 - Ryan's transition from employee to owner 05:40 - Ryan's background before joining the company 07:05 - Why confidentiality matters during a business sale 08:05 - How ownership changed Ryan's mindset…

In this special anniversary episode of What's Your Deal?, the mic flips as Sarah interviews Matt Uhler on one of the most requested topics yet—how to build multiple streams of income through small business ownership. After producing 40+ episodes covering buying, managing, and exiting businesses, this conversation dives into the strategy Matt has personally used to build a portfolio of 20+ income-producing businesses—what he calls his own "business mutual fund." Matt breaks down the Faucet Framework, a proven system for creating diversified, predictable income without relying on a single source. From minimizing risk to structuring partnerships the right way, this episode gives you a real-world blueprint for financial stability and long-term freedom. If you're a: Business owner looking to diversify Investor exploring small business opportunities W2 employee wanting more control over income This episode is for you! If this topic interests you, fill out this form to get early access and details on our upcoming…

What does it really take to leave a stable career and step into business ownership? In this episode of What's Your Deal?, Matt sits down with Kevin Mizell, a former government construction engineer manager who walked away from a high-level career to buy a small business—right in the middle of the pandemic. Kevin shares the real, unfiltered truth about what it's like to go from a W2 job to owning a business. From taking on large debt for the first time, to navigating labor challenges, to realizing that "passive income" isn't what most people think—it's all here. If you've ever thought about leaving your W2 job and buying a business, this episode will challenge your assumptions and give you a grounded, real-world perspective on what it actually takes to succeed. This isn't theory. This is what it looks like in the real world. Timestamps: 02:00 – Leaving a stable career for business ownership 06:00 – Early entrepreneurial thoughts and risk considerations 10:00 – Choosing the right business (and core competency)…

What does it really mean to be a great leader? In this episode of What's Your Deal?, Matt sits down with leadership coach Keith Cowling to unpack what most people get wrong about leadership—and how to actually build influence that lasts. Keith shares lessons from over 30 years of working with business owners, teams, and individuals, revealing why leadership starts internally—not externally. From letting go of ego to learning how to truly develop people, this conversation goes far beyond surface-level advice. If you've ever struggled with managing people, holding others accountable, or balancing leadership at work and at home—this episode will challenge how you think and lead. This isn't about control. It's about growth, influence, and becoming the kind of leader people choose to follow. Timestamps 01:49 – Why most leadership stays surface-level 02:36 – Keith's early struggles with leadership and control 04:09 – The turning point: focusing on people over productivity 08:40 – Leadership vs. success: why…

In this episode of What's Your Deal?, Matt sits down with repeat guests Luke McCarthy and Colton Imming to break down one of the most misunderstood topics in today's world—Bitcoin. This conversation goes far beyond crypto hype. It dives into the fundamentals of money, inflation, asset ownership, and long-term wealth strategy. Luke and Colton share why they've shifted their focus from traditional assets like real estate into Bitcoin, how they're using it to protect their wealth, and what it means for the future of investing. If you've ever questioned how money actually works—or why it feels harder to get ahead—this episode will open your eyes. Timestamps 02:10 – Bitcoin vs Cryptocurrency: What's the Difference? 03:25 – Bitcoin vs Gold: Understanding Scarcity 04:45 – The Hidden Truth About Money & Inflation 10:45 – How Bitcoin Changes Your Understanding of Money 11:50 – Why Inflation Doesn't Always Look Like Inflation 14:40 – The Growing Wealth Gap Explained 16:10 – Why Governments Will Keep Printing Money…

What happens after you sell your business? In this episode of What's Your Deal?, Matt Uhler sits down with Paul Hickey, CEO of Legacy Wealth Management, to talk about one of the most overlooked parts of business ownership: what comes next after the exit. Paul shares insights from decades of experience in global finance, investment banking, IPOs, mergers and acquisitions, and entrepreneurship. Together, Matt and Paul unpack why so many business owners focus on getting out of the business but fail to prepare for life after the sale. They discuss the emotional side of exit planning, the identity shift many owners face, how to avoid blowing through hard-earned wealth, and why creating a life plan is just as important as creating a financial plan. Paul also explains the value of starting early, building a team before the sale, and using strategic planning to reduce taxes and generate sustainable income after an exit. This is a valuable conversation for business owners who want to sell wisely, protect their…

In this episode of What's Your Deal?, Matt sits down with Carlos Salguero, President and Founder of CS3 Investments, to break down why multifamily real estate isn't just "real estate"—it's an income-producing business. Carlos shares his journey from growing up in Ecuador working in his family's print shop to building and exiting multiple businesses, and ultimately scaling into commercial multifamily—now totaling 1,900+ doors. Together, Matt and Carlos connect the dots between buying businesses and buying properties, including how experienced operators find opportunities in deals that developers often leave on the table. They also walk through the mindset shift many entrepreneurs face after realizing that owning rentals can turn into the "triple T's" (tenants, toilets, and termites)… and how syndications can provide a more truly passive route for business owners looking to diversify beyond their primary company. Timestamps: 00:16 – Introducing Carlos Salguero: From Ecuador to 1,900+ Multifamily Doors 02:42 –…

In this episode of What's Your Deal?, Matt sits down with John Bowens, Director of Head of Education & Investor Success at Equity Trust, to break down one of the most overlooked wealth tools for entrepreneurs and investors: self-directed retirement accounts. John explains what "self-directed" actually means, why most retirement money stays locked in mutual funds by default, and how investors can use IRAs, 401(k)s (and even HSAs) to invest in real estate, private lending, private equity, pre-IPO stock, cryptocurrency, and precious metals—all while keeping the tax advantages of retirement accounts. They also dive into the ROBS (Rollover for Business Startups) structure and how some buyers use retirement funds to acquire a business without triggering taxes and penalties—plus the common mistakes and prohibited transaction rules that can trip people up if they don't understand the guardrails. If you've ever wondered how to put your retirement money to work in the assets you actually understand—this episode is…

In this episode of What's Your Deal?, Matt Uhler interviews Larry Yatch — former U.S. Navy SEAL officer turned entrepreneur strategist and high-performance coach — about the unseen survival patterns that drive decisions in business, money, leadership, and relationships. Larry explains why most people misunderstand trauma: it's not about the event — it's about the subconscious strategy your brain adopts to survive when your perception of control is taken away. Those strategies can create success… but they can also create burnout, misalignment, and self-sabotage if they remain unrecognized. Matt ties this directly to what he sees in real deals: sellers backing out at the finish line, leaders who can't rest even when they "have everything," and entrepreneurs who keep grinding because their subconscious equates love, worth, or identity with pain. If you're building a business, leading a team, negotiating deals, or trying to grow your income — this conversation will help you understand what might be running the…

In this episode of What's Your Deal?, Matt Uhler sits down with Colton Imming, to unpack what it really looks like to leave a W2 career behind, bet on yourself, and step into business ownership. Colton shares his path to a private equity environment that rewarded performance — and how a long-term plan with his wife, Katie, helped them prioritize freedom, family, and control over their time. That journey eventually led to Colton partnering with two others to build a holding company focused on acquiring and stewarding small businesses. From there, the conversation goes into the real-world lessons you only learn after closing: why proximity matters, what happens when you lose a major client, why "easy upside" improvements like adding a CRM can be a much heavier lift than expected, and the critical importance of being well-capitalized so you're making decisions for the long-term — not just trying to survive payroll. Matt and Colton also discuss a topic buyers rarely hear addressed openly: the reality of working…

In this special "Deal or No Deal" episode of What's Your Deal?, Matt sits down with returning guest Keith Sklarsky to dissect a real $5.5 million logistics business — and decide whether it's worth pursuing. On paper, the business checks some important boxes: multi-million dollar revenue, strong recent growth, and nearly $1 million in projected discretionary earnings. But as Matt and Keith dig deeper, the red flags begin to surface. From fluctuating earnings and aggressive marketing spend to questionable independent contractor classifications and unrealistic valuation multiples, this episode is a masterclass in disciplined deal evaluation. If you're considering buying a business — or want to avoid making a million-dollar mistake — this conversation will help you think like a seasoned operator. Timestamps 02:10 – Why real deal breakdowns matter 04:30 – Overview of the $5.5M logistics brokerage 06:00 – First guardrails: region, size, and impact 09:45 – Revenue growth vs. sustainability 11:00 – SDE vs EBITDA —…

In this episode of What's Your Deal?, Matt Uhler sits down with Keira Hamilton, a former high school English teacher with a master's in education from UC Berkeley who made an unexpected leap into business ownership. Keira and her husband bought their first business — a San Francisco laundromat — in 2023, learned fast why "passive income" is often a myth, and then sold the laundromat in 2024 after improving systems and operations to make the business more transferable. From there, they moved to San Diego and acquired their next business: Sunshine Window Cleaning, an off-market service company they found through cold outreach. Keira breaks down what most buyers underestimate (especially proximity, staffing realities, and operating complexity), how transparency builds trust in a transaction, and why "perfect certainty" isn't a requirement to buy — but courage, skill-building, and runway management are. If you're exploring your first acquisition, thinking about "semi-absentee" ownership, or trying to understand…

Most business owners spend years building something valuable — yet never prepare it to be sold. In this shorter episode of What's Your Deal?, Matt Uhler and Sarah Rainwater break down why exit readiness is one of the most overlooked (and most powerful) strategies in business ownership. Preparing your business for exit isn't just about selling — it's about running a healthier, more profitable, and more valuable business today, while preserving the option to exit when and how you choose. Matt shares real-world experience from decades of buying, selling, and advising business owners, including why most businesses are not ready to sell when owners think they are, how small financial decisions multiply at exit, and why time and preparation dramatically change outcomes. Whether exit is on your radar now or years away, this conversation will help you start thinking like an owner — not just an operator — and treat your business like the asset it truly is. Timestamps: 00:16 – Why exit readiness matters for every…

In this episode of What's Your Deal?, Matt breaks down real estate through the lens of business acquisition with August Biniaz, Co-Founder and CIO of CPI Capital. This conversation goes beyond property investing and gets into what it really means to acquire, operate, and scale assets like a business. August shares how he evaluates deals, raises capital, structures deals, and manages risk—principles that directly mirror buying operating companies, not just real estate. TIMESTAMPS: 00:16 Meet August Biniaz + CPI Capital overview 01:55 From broker → fix & flips → becoming the GC 03:25 Homebuilding in Vancouver/Toronto and the desire to scale 04:05 Why August moved into private equity + the motivation behind CPI 05:25 Why CPI pivoted toward U.S. deals for Canadian investors 07:17 Funds vs. syndications: how the capital-raise process works 08:48 Why CPI likes multifamily: demand, rent-to-value ratios, and scale 13:12 CPI's strategy: multifamily value-add and "forced appreciation" 16:24 Build-to-rent (BTR): what…

In this episode of What's Your Deal?, Matt sits down with returning guest Dana DeVito, coach and consultant with Elite Performance Associates, to tackle one of the most common — and costly — problems business owners face: becoming the bottleneck in their own business. Many owners start their companies because they're great technicians. But as the business grows, that same strength becomes the very thing that limits scale, profitability, and freedom. Dana and Matt unpack why owners struggle to let go, how perfectionism and micromanagement quietly hold businesses hostage, and why delegation without accountability always fails. If you want a business that can grow, operate, and eventually sell without you being involved in everything, this episode is a must-listen. Timestamps: 01:00 – Why owners become bottlenecks without realizing it 02:30 – Technician vs. owner mindset 04:30 – Perfectionism and the fear of letting go 06:30 – Micromanagement: when it helps and when it hurts 08:30 – "I can outwork anyone… but…

In this episode of What's Your Deal?, Matt sits down with Maxwell Nee, Chairman of Family Office Insider. Maxwell specializes in capital structuring, partnerships, and large-scale growth opportunities. Maxwell shares how he moved from an unfulfilling corporate banking career into high-level dealmaking across industries like renewable energy, mining, waste processing, and advertising. This conversation dives deep into the mindset behind raising capital, structuring partnerships that actually work, and why clarity, resourcefulness, and communication matter more than money. Timestamps: 01:20 – Maxwell's background and Family Office Insider 03:40 – Core competency and knowing your role 05:30 – Why partnerships get a bad reputation 08:32 – Deal-making mindset and resourcefulness 13:50 – Capital raising mistakes entrepreneurs make 18:40 – Why subtlety beats aggressive pitching 21:25 – Fun, freedom, flexibility — and thinking bigger 26:20 – Why large deals are often smoother 30:10 – Structuring growth and expansion…

In this episode of What's Your Deal?, Matt Uhler sits down with Eric Tastet, whose journey took him from 20 years in ministry to becoming VP of Client Strategy at Aspire Tour—and the lead instructor for Aspire's Tax-Free Crypto Education program. Eric breaks down what he's learned about human dynamics, why most people get stuck in "learning" instead of actually taking action, and how relational equity is often the real currency behind influence and results. They also dig into the mindset shift between being a contributor vs. a creator, why consistency beats motivation every time, and how self-directed strategies can open the door to building wealth with more ownership and intention. Timestamps: 00:16 Meet Eric: ministry background + current role at Aspire Tour 01:15 Transitioning from ministry to business (and why it happened) 04:13 "Now I know why you're there…" (real talk moment) 05:35 Eric's two roles at Aspire: client strategy + crypto education 09:15 Human dynamics: why people get stuck and how to…

In this episode of What's Your Deal?, Matt is joined again by one of our most-listened-to guests, Lindsay Denton. For the past seven years, Lindsay has worked side by side with Matt arranging financing for business acquisitions inside the brokerage. Now, through Amped Funding Advisors, she is assisting buyers and sellers nationwide structure deals for approval and funding. They break down why business financing is nothing like getting a car loan or a mortgage, why SBA loans come with so many rules, and how to navigate those rules without losing your mind or your deal. Lindsay walks through what really goes into a strong lending "package," why projections and business plans matter so much, and how her team scrubs deals before an underwriter ever sees them. Timestamps: 01:29 Brokerage financing vs. nationwide funding advisory: what's different 03:15 What's in a "package"? Buyer/seller financials, skeletons in the closet, and sourcing funds 04:55 Why you can't just walk into an SBA lender and apply like a…

In this episode of What's Your Deal?, Matt sits down with close friend and colleague Steve Williams, CEO of Aspire Family Bank, to unpack a powerful alternative to traditional estate planning: the Family Bank. Steve shares his journey from growing up in generational poverty to climbing the corporate ladder— and then walking away to build a boutique real estate development firm with his wife. Along the way, he learned the hard lessons of leadership, doing hard things, and raising kids who have accountability instead of entitlement. Covering topics like—why whole life insurance are the only vehicles that truly power Family Banks. Steve explains how families can create generational security (not just generational wealth). You'll hear how family constitutions, governance, and loan-based support can give your kids a "silver hammer instead of a silver spoon"—so they build their own purpose, while your legacy lives on for generations. Timestamps 00:16 – Meet Steve Williams: Corporate background & entrepreneurial…

In this heartfelt episode, Matt sits down with his wife, Audrey Uhler, for an unfiltered conversation about marriage, blended family life, and the realities of running multiple businesses together. They share how they've navigated financial stress, busy travel schedules, parenting transitions, and the constant pull between work and family. Matt and Audrey open up about what it takes to keep both a marriage and a business thriving through seasons of change. They also talk about the emotional shift that comes with an emptying nest, rediscovering purpose, and dreaming up their next chapter together. Timestamps 00:00 – Introduction 03:07 – Dating an Entrepreneur 05:10 – From Single Parents to Blended Family 09:04 – Working Vacations That Actually Work 11:40 – The Excitement and Exhaustion of the Deal Life 13:54 – The Swamp Leak Story 18:41 – The "Fun-Money" System 20:45 – Empty-Nest Emotions & New Identity 24:04 – Vision vs. Logic 34:25 – Designing Their Desired End State 37:10 – The "Hand-Up" Question Resources…

In this episode, Matt sits down with longtime friends Steve and Michele Sullins — two powerhouse restaurateurs who've built, bought, and sold multiple restaurants and retail stores over the past 35 years. Michelle started with a coffee cart in Sedona and grew it into a thriving restaurant empire, while Steve worked his way up from dishwasher to opening restaurants for major resort brands like Hyatt and Loews. Together, they've mastered the balance of systems, leadership, and partnership — both in business and marriage. From promoting employees into management to scaling multiple locations at once, they share how they've built lasting success in one of the toughest industries around. Now, they're taking that experience to Prescott with The Copper Note, their newest concept bringing elevated, scratch-made "world comfort food" to the downtown Prescott area. Timestamps: 0:00 – Intro and why Steve & Michele chose restaurants in the first place 3:34 – Michele's first restaurant purchase in Sedona 4:25 – How she…

Matt shares the origin story behind his career in business brokerage and ownership: growing up with a single mom working seven days a week, taking third-shift janitorial work at 13, and starting his first company at 17. A shop teacher's nudge ("why not start a business doing what you already know?") led to a janitorial company that scaled from one account to 40 employees across New Hampshire and Massachusetts. That first exit came with hard lessons—especially around reading P&Ls and not letting the business "run" the owner. The sale also revealed a bigger truth Matt has seen for 27 years: buying a good business can change a family's trajectory overnight. Since then he's completed over 800+ deals, evaluated thousands more, and taken ownership stakes in 35+ companies (about 20 active today), partnering with "boots-on-the-ground" operators and stepping in most deeply when there's a fire to put out. Matt talks balance, rhythm, and family. Ownership gives freedom to choose where to spend time—but responsibility…

Today we welcome Dana De Vito, a longtime business owner, franchise operator, and co-founder of Elite Performance Associates. From owning Jack in the Box and Scooter's Coffee franchises to coaching business leaders, Dana shares his insights on responsible growth, the difference between consulting and coaching, and why defining a desired end statematters more than tactics. This conversation digs into lessons learned from franchising, building culture, and balancing ambition with life outside of business. Timestamps: 00:01 – Intro & welcome to the show 00:32 – Meet Dana De Vito: from teacher-track to consulting 03:02 – Moving to Prescott & buying Jack in the Box franchises 04:55 – Lessons from fast food ownership & team development 06:03 – The ups and downs of franchising relationships 07:36 – Why Scooter's Coffee: leadership culture & systems 10:10 – Consulting vs. coaching: the real difference 13:38 – Why some owners act—and others never do 18:14 – Crisis survival: losing 97% of revenue & bouncing back 20:50…

In part two of our series on preparing your business for sale, Matt is once again joined by Lindsay Denton. Together they dive deep into the often-overlooked details that can make or break a deal: commingled entities, lease negotiations with landlords, environmental and maintenance concerns, and the importance of correctly titled assets. Packed with real-world stories, hard-earned lessons, and practical strategies, this conversation is a must-listen for business owners looking to maximize their exit value — and for buyers who want to understand the hidden risks behind the numbers. 2:25 – Preparing for sale: beyond financials into entity structures 3:45 – The problem with commingled entities (and how it kills deals) 7:20 – Real-life examples: when businesses can't be valued or financed 10:00 – How separation delays, amendments, and CPA involvement stall deals 12:00 – The effects of messy financials and tax returns 16:05 – Landlord dynamics: renewals, greed, and lease assignments 19:10 – How one owner lost a…