465 episodes listed below
Growth, negotiated one deal at a time.
DealQuest treats growth as something that can be structured, negotiated, and planned. Corey Kupfer talks with business owners, executives, leaders, entrepreneurs, and dealmakers about deals that shaped their companies, from tuck-ins and exits to partnerships and tax strategy.
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DealQuest is a business interview show about growth through deals. Its center of gravity is practical M&A, but the scope is wider than buying and selling companies. Episodes move through capital raising, strategic alliances, tuck-in acquisitions, franchising, real estate, sponsorship arrangements, equity compensation, and exit planning. Corey Kupfer brings a dealmaker's lens to each conversation, pressing guests for the story behind the transaction and then for the lesson inside it. The result is brisk but usable. A guest might explain how advisor-client relationships transfer in a practice sale, and the conversation quickly turns to retention, trust, timing, and what the buyer must not overlook. Another episode might follow a founder through multiple technology exits, using that history to talk about product timing, acquisition paths, and repeat entrepreneurship. The show is especially interested in the lower and middle market, where structure, diligence, and human judgment often matter as much as headline price. It also pays attention to softer motives. Some owners want the biggest check. Others care about legacy, family, charity, employees, or a second bite of the apple. DealQuest makes room for those tradeoffs without turning sentimental. Its recurring strength is translation: legal, tax, valuation, and deal language gets pulled back into plain business choices. The interviews are guest-forward, but they rarely drift. Short acknowledgments and follow-up questions keep the pace moving. Recent conversations with people such as Jerry Blakely, Raj Singh, Andrew Ackerman, Greg Waller, and David Flores-Wilson show the range: practice transitions, startup investing, company sale value, tax-smart exits, and risk allocation. For founders and owners, the show works like a field guide to becoming more deal-literate before the next opportunity appears.
Made for: For founders, business owners, executives, advisors, and investors who want clearer judgment around acquisitions, exits, partnerships, capital, and succession. It also suits operators preparing for a sale or trying to understand what makes a company more valuable.
What sets it apart: DealQuest stands out by keeping deal mechanics tied to lived business stories. It treats terms, taxes, valuation, retention, and legacy as connected parts of the same owner decision, not separate expert silos.
Why do some companies grow by leaps and bounds while others only inch forward? Simple. They embrace Deal-Driven Growth in addition to organic growth! DealQuest is where you learn how to strategize, prepare for, find, and complete deals to grow your company faster.Listen in as host Corey Kupfer takes you behind the scenes with some of the world’s most fascinating deal-savvy business leaders. This is the one place where they can share openly the secret to deals they have done (or failed to do) and the issues, opportunities, benefits, pitfalls and lessons learned.Here you learn first-hand all about: Powerful deals that require little capital, mergers, acquisitions, and tuck-ins, Joint ventures,…
Based on 5 episodes we listened to · September 2026
Corey Kupfer makes deal structure, risk, valuation, and post-exit consequences legible through practical conversations grounded in real business decisions.
DealQuest Podcast with Corey Kupfer treats dealmaking as a chain of consequential choices rather than a victory lap. In guest conversations, Kupfer keeps returning to the mechanics beneath growth and ownership: how risk is allocated, how a sale is structured, what due diligence…
The sale price looks good; Corey Kupfer wants to know what you'll do afterward.
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Short reviews from the PlayNext desk, based on the episodes we processed.
Andrew Ackerman gives founders a practical way to think about lawyers, negotiation, and risk.
Andrew Ackerman turns deal-driven growth into something entrepreneurs can actually use when the negotiation table gets crowded. His central point is simple and useful: counsel should help identify where the real risks sit, which ones are major or minor, where to bargain hardest,…
A practical discussion of how preparation, process, and buyer competition shape a company's sale value.
For owners weighing a sale, this episode treats value as something built through process, not guessed at in a boardroom. Corey Kupfer's conversation with Dr.
A practical discussion of exit structures, equity plans, and the human goals that tax strategy alone cannot settle.
Exit planning comes through as a business choice inseparable from personal goals. David Flores-Wilson looks at what can sit behind a monetization event: pursuing the top price in a strategic deal, rolling up for another bite of the apple, using an ESOP to preserve a legacy, or…
Rental wealth is presented as patient work sustained by knowledge, action, and genuine enjoyment.
Rental-property wealth comes across here as a practice built over time, not a shortcut. Joe Miller ties education and knowledge to keeping calamity out of the process, and he treats enjoyment as part of what makes commitment last.
A candid look at the deal terms and identity shock that can follow a business exit.
DealQuest's conversation with Bill Davey frames a business exit as a shift in responsibility, identity, and daily purpose, not just a transaction.
Rob Walling on bootstrapped SaaS growth, plateaus, and exits — with founders who lived them.
Abbey Ashley's playbook for turning your job skills into a virtual assistant business.
SaaS operators on scaling, pricing and AI, metrics included.
Alex Blumberg interviews guests like Megan Phelps-Roper and Shane McAnally about failure and reinvention.
John Wells discusses strategic group home investments for long-term wealth building, focusing on sobriety and mental health properties in Denver.
A mobile DJ who became a real estate investor and hard money lender shares how he built wealth over 47 years.
After selling his business, Bill Davey played golf every day but found himself missing the chaos and feeling empty.
Corey Kupfer interviews franchise expert Greg Mohr about how to franchise a business the right way, covering strategies for growth and common pitfalls.
Corey Kupfer interviews Jodi Hume about founder regret, exit clarity, and what money can't buy, sharing insights from her career as a COO and turnaround CEO.
Corey Kupfer interviews John Martinka, the 'escape artist,' about creating lucrative exits for small businesses and driving growth through acquisitions.
Jaden Sterling discusses how a single stock tripled in value, enabling him to build a real estate empire, and shares his journey from Wall Street to creating an accessible investing platform.
Hannah Sandmeyer, founder of Up and Over Advisors and Steward Market, traces her path from wanting to be an ACLU lawyer in Boise, Idaho, through the Peace Corps and 18 years in sales to ethical M&A.
Leah and Rebecca Wiser, twin sisters and creative partners, discuss how they built a successful business partnership and help service-based businesses enhance their brands and websites.
Jerry Blakely discusses strategies for achieving 97% client retention in financial advisor practice transitions.
Corey Kupfer's DealQuest episode asks whether every entrepreneur should become a dealmaker, despite deals offering ways to accelerate revenue, value, talent, geography, and product expansion.
Marty Fahncke tells Corey Kupfer how a grassroots sporting-goods company sold for $1.5 million and how he later estimated that rejecting rollover equity cost him approximately $24 million.
Raj Singh, VP of Product at Mozilla, tells Corey Kupfer how his Cookpad, Salesforce, and Opera exits each came together under different timing and market conditions.
Corey Kupfer opens with deal-driven growth.
DealQuest Podcast host Corey Kupfer interviews Dr.
DealQuest episode 390 focuses on tax-smart exit planning, and David Flores-Wilson spends much of the conversation on QSBS, C-corp conversions, and equity compensation.