Most entrepreneurs think raising VC money means they've "made it." But Tom Dillon learned something different during his years in investment banking and running a PE-backed company. After analyzing countless deals and experiencing the pressure firsthand, he discovered that VC money comes with a specific expectation: IPO-level returns. "For a lot of VCs, they kinda look at things in terms of roulette table. They really need one of those to hit big." The problem? Most successful businesses exit th...
Jul 09, 2025•43 min
Georgi Feidler shared some incredible stats with me... Over 50% of small businesses are owned by Baby Boomers. 60% of those have zero succession plan. That's billions in wealth transfer happening right now and most of it is going to be messy. Georgi has spent 20+ years helping founders navigate this transition. Her approach isn't just about finding buyers - it's about building businesses that can actually survive without their founders. The brother/sister case study she shared shows how creative...
Jul 02, 2025•51 min
Attention entrepreneurs: If you think working 80+ hour weeks makes your business more valuable... the data says otherwise. This conversation will change how you think about business building forever. James Brown didn't just sell his business for multiple cash offers he proved that less owner involvement equals higher business value. James is the founder of BizTech Guru, a business consultant who transformed his own accommodation business over many years from requiring 120-hour work weeks to just...
Jun 25, 2025•44 min
If you think Shark Tank shows you how real investment deals work, it's time to look deeper. After 35+ years of structuring actual deals, I have some thoughts. Don't get me wrong. Shark Tank has done incredible things for entrepreneurship awareness. It's entertaining. It introduces people to concepts like customer acquisition costs and business valuations. But as someone who negotiates real deals, the show misses so much of what actually happens. Mark Cuban's "shot clock" negotiations? Not how re...
Jun 18, 2025•22 min
If your definition of success still sounds like someone else’s dream… It’s time to rewrite it I was deeply moved by this conversation with the incredible Rha Goddess. - CEO of Move The Crowd, the author of The Calling, and a cultural innovator who has helped hundreds of changemakers stay true to themselves while making bank. In this episode, she breaks down how to negotiate deals with soul, reclaim your worth in high-stakes rooms, and redefine success on your own terms. We talked about ambit...
Jun 11, 2025•56 min
Feeling stuck inside someone else’s definition of success? If you’re a financial advisor dreaming about building a business on your terms, this is for you. Because here’s the thing… The RIA model is one of the most powerful paths to real independence in the wealth management space. And this DealQuest episode, we’re talking with Chuck Failla—founder of Sovereign Financial Group and a fierce advocate for advisor freedom. He’s breaking down: - Why so many advisors are finally making the leap - What...
Jun 04, 2025•50 min
Why REPORTERS might know more than the CEOs they cover… Couldn’t agree more with the insights dropped by Diana Britton and Ian Wenik on this episode of DealQuest. In case you don’t already know Diana & Ian… Ian is the Editor at Citywire RIA and host of This Week in Wealth Diana is the Managing Editor at WealthManagement.com and host of The Healthy Advisor Podcast Together, they’ve interviewed just about everyone in the RIA space (yours truly included) They’ve spent years behind th...
May 28, 2025•53 min
For YEARS, business owners have been told to wait for the right time to make deals, especially when the economy feels uncertain. But… that strategy could be killing your momentum. In this solocast episode of the DealQuest Podcast, I’ll break down… - Why fear-based decisions kill more deals than a downturn ever could - How to shift your mindset from reactive to strategic - What smart deal structures look like in a changing market - How to stay confident (even when the headlines say panic) A...
May 21, 2025•21 min
What you think selling a startup looks like vs. what it actually looks like Here’s what most founders assume about startup acquisitions… You need to raise millions in VC funding first Only “unicorns” get acquired It’s a long, complicated process with lawyers and bankers You need to scale like crazy before you sell Only big-name founders get exits NOPE. You can build a lean, profitable business and sell it without a huge team, a pile of funding, or a decade of hustle. And Andrew G...
May 14, 2025•47 min
Is your business really built to scale? Most entrepreneurs dream of growing fast… but here’s the truth: speed alone won’t get you to sustainable success. This insight from business growth expert Robert Levin says it all… Scaling isn’t just about getting bigger—it’s about getting better, stronger, and more profitable in the long run. And more and more entrepreneurs are learning this the HARD way after chasing growth at all costs… These failures are due to poor scaling decisions… Expanding too qui...
May 07, 2025•52 min
Want to make your business irresistible to buyers? Let’s talk MARKETING in M&A… Too often, businesses focus only on financials when preparing for an acquisition— But buyers don’t just pay for numbers. They pay for BRAND, POSITIONING, and GROWTH POTENTIAL. If you’re ignoring marketing due diligence in M&A, you’re leaving money on the table. A strong marketing strategy = higher valuations, smoother transitions, and long-term success post-acquisition. So, ask yourself… Is your marketing eng...
Apr 30, 2025•43 min
Thinking about selling your business? You need strong G2 & G3 leadership in place first. Tune into my solocast episode to see why it’s a game-changer for valuation, deal structure, and a smooth exit. If you're an investor or business owner planning for the future, pay close attention… Because leadership gaps can kill a deal before it even starts. A strong leadership pipeline ensures: Higher business valuation More attractive deal structures Seamless mergers & acquisitions A legacy that o...
Apr 23, 2025•23 min
"YOU DON'T HAVE TO CHOOSE BETWEEN YOUR CAREER AND REAL ESTATE INVESTING." Many people believe you can't successfully invest in real estate while maintaining another career or business. THINK AGAIN. Joel Miller has been investing in rental properties since 1978 and has flipped over 100 houses since 1991 – all while maintaining a 35-year career as a professional mobile DJ with 5,051 appearances. And guess what? His first property from 1978? He STILL owns it 47 years later, and it's a "cash cow" wi...
Apr 16, 2025•49 min
Mergers are exciting… until the real work begins. I had an incredible conversation with Jonathan Gardner on this podcast episode. This is something we don’t talk about enough… (We spend so much time focusing on closing the deal)… But we’re not REALLY talking about what happens after—the post-merger integration that can make or break the entire deal. When you… Align teams and company cultures seamlessly… Avoid the costly integration mistakes most businesses make… Ensure a smooth transition for cu...
Apr 09, 2025•41 min
Had an incredible conversation with Devan Gonzalez about scaling a fitness business the right way—without burning out or sacrificing quality. We broke down how he went from corporate trainer to thriving gym owner, built a game-changing franchise model, and turned sales into service (no sleazy tactics here). We covered so much in this episode, including: - How Devan went from corporate trainer to thriving gym owner - The business model shift that benefits everyone—clients, trainers, & the gym...
Apr 02, 2025•49 min
Sovereign wealth funds are changing the M&A game! Keep reading to find out how Everyone is talking about private equity in mergers and acquisitions... but they’re overlooking a major player. Sovereign wealth funds are making big moves in the investment advisory space. And they’re reshaping valuations, deal structures, and long-term exits in ways that most advisors aren’t prepared for. If you’re in M&A, you need to know what’s happening Sovereign wealth funds now control over $11 trillion...
Mar 26, 2025•19 min
Hold on to your coffee cups, folks —we're diving deep into the world of private capital, emerging markets, and coffee investments today! In this episode of the DealQuest Podcast, I’m chatting with Cole Shephard, founder of Green Coffee Company, about how he turned Colombian agriculture into a business powerhouse. This episode is a game-changer for anyone interested in real estate, coffee, or emerging markets. Here’s the deal—Cole’s journey from corporate finance to entrepreneurship is packed wi...
Mar 19, 2025•49 min
Want to unlock the real secrets of building a successful franchise? Then you NEED to hear this conversation with franchise expert Greg Mohr! In this episode, Greg breaks down the biggest mistakes new franchise owners make and what it actually takes to create a business that works for you—not the other way around. Greg has helped countless entrepreneurs break free from the 9-5 and find the perfect franchise fit for their goals, lifestyle, and financial freedom. If franchising has ever crossed you...
Mar 12, 2025•46 min
Want to learn the secrets to a lucrative business exit?! Then you NEED to check out this episode with business transition expert John Martinka! John has been helping entrepreneurs buy, sell, and scale businesses for over 25 years… In this episode, he’s revealing the key strategies that make the difference between a profitable business sale and a missed opportunity. BTW… these are real-world tactics that ANY business owner can apply to maximize their company’s value before an exit. If you’ve ever...
Mar 05, 2025•40 min
If you’re trying to predict where the M&A market is headed in 2025… you need to hear this. The economy, the election, the shifting deal landscape—there’s a LOT to unpack. And in this episode, we’re breaking it all down. What’s happening in the market right now Where deal opportunities are (and where they’re drying up) The biggest risks and how to navigate them • • • FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/2025MAMarket • • • FOR MORE ON COREY KUPFER: https://www.linkedin.co...
Feb 26, 2025•19 min
Are YOU the bottleneck in your business? In this episode of the DealQuest Podcast, I’m joined by Pete Mohr, certified exit planning coach, to share actionable strategies to reclaim your time, build a self-sustaining business, and exit with confidence. You’ll get the lowdown on: - Creating a business that works for you - How to plan your exit strategy early -The secret to building a brand and team that thrives without you If you’re tired of feeling like your business can’t run without you (beca...
Feb 19, 2025•49 min
When it comes to business growth, it’s not about chasing every opportunity or following the latest shiny object. Here’s the thing: You need to focus on what actually works. So stop overcomplicating it. What really moves the needle? Building systems that help you scale and finding the right strategies that actually make sense for YOU. In this episode of the DealQuest Podcast, I sat down with Cliff Nonnenmacher, a serial entrepreneur and franchise mastermind, who’s built and scaled successful busi...
Feb 12, 2025•51 min
If this is the year YOU plan to scale your business while unlocking the freedom you’ve always dreamed of… Then this podcast episode is for you! Richard Manders, an accomplished entrepreneur and seasoned business coach, joins me to discuss: How to prepare your business for inevitable challenges (even when things are going great)... The secret to choosing a capital partner who adds real value beyond just funding… Why aligning leadership roles with your strengths can supercharge growth... And how c...
Feb 05, 2025•56 min
Business owners everywhere are chasing the quick wins — faster content, bigger audiences, more sales. But here’s the thing: Authenticity is the real game changer If you're in business, you know how easy it is to fall into the trap of sales pitches and automation. But listeners, clients, and followers? They’re craving something different. They want connection. They want value. They want YOU. In this episode of the DealQuest Podcast, I’m sharing why I’ve stayed true to providing real value — no ad...
Jan 29, 2025•15 min
Want to build generational wealth but don’t know where to start? Hint: It’s sitting in your wallet. Credit isn’t just for emergencies or big-ticket purchases—it’s a tool that can unlock funding for your dreams, fuel your business growth, and secure a financial legacy. But if you’ve been stuck thinking credit is a limitation, it’s time to flip the script. On this DealQuest Podcast, Herman Dolce breaks down: How to leverage credit for financial independence Steps to start building generational wea...
Jan 22, 2025•45 min
Learn all about how ESOPs can help you sell your business to employees while preserving company culture and maximizing tax benefits. This episode of the DealQuest Podcast with Kelly Finnell is packed with insights! Wondering how to plan for your business exit? Or how an ESOP could provide a smooth transition while rewarding your team? Tune in to hear Kelly break it all down, plus real-world examples of how ESOPs have transformed businesses. Ready to listen? • • • FOR MORE ON THIS EPISODE: https:...
Jan 15, 2025•50 min
What does resilient leadership look like in business? If you’re ready to scale your business to new heights, there’s one lesson you can’t ignore: resilience. Sejal Lakhani-Bhatt, CEO of TechWerxe has gone from global banking floors to leading her IT company to $10M in revenue. And she’s sharing her secrets on how to overcome loss, lead with vision, and scale sustainably. This episode is packed with gold for anyone aiming to grow their business, no matter the obstacles • • • FOR MORE ON THIS EPIS...
Jan 08, 2025•41 min
The holiday season provides an opportunity for introspection. It is a time to evaluate the choices we have made and to envision a brighter future. We must question our motivations and ensure that our deals are not driven solely by external forces or societal expectations. Instead, they should be in harmony with our authentic selves and the lives we genuinely want to create. Building a business or making investments should not be solely for the sake of growth or validation. It should be a means t...
Jan 01, 2025•21 min
What does freedom mean to you? Is it more time to do what you love? Financial stability to take risks? The ability to build a life on your terms? In this Best Of Episode, we dive into the diverse and deeply personal perspectives of 9 amazing guests as they unpack what freedom truly means to them. From redefining freedom beyond money and time to making decisions that align with your vision—this episode is full of inspiration and insight. Ready to reflect on your own definition of freedom? • • • F...
Dec 25, 2024•19 min
Want to make your business more financially stable? Brooke Lively, financial expert and founder of Cathedral Capital, has the answers. She’s breaking down how to create predictable income streams, keep your financials clean, boost business valuation, and plan a profitable exit! What if I don’t have recurring revenue? No problem! Brooke breaks down strategies for businesses with non-recurring revenue models (like law firms and consultancies) to create stability and attract buyers Do I need to hav...
Dec 18, 2024•43 min
