DealQuest Podcast with Corey Kupfer

Corey Kupfer

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, partnerships, and strategic alliances, licensing, raising capital and onboarding key employees, negotiating, structuring, finding, valuing, closing and integrating deals. Don’t be the one at the table who doesn’t grasp the power of Deal-Driven Growth!

  1. 6d ago

    Episode 423: Making M&A a Force for Good with Hannah Sandmeyer

    In her first 90 days running corporate development for a venture-backed acquirer, Hannah Sandmeyer closed sixty million dollars in EBITDA. The company had raised a billion dollars in a single Series D and its whole model was growth by acquisition. Then it collapsed when the promised IPO never came. That experience showed her how powerful M&A can be, and it set up the question behind everything she does now, which is what that power looks like when it serves something other than speed and price. Hannah is the founder and CEO of Up and Over Advisors, the first certified B Corporation in the world dedicated exclusively to values-aligned M&A sourcing, and the founder of Steward Market, a live three-sided marketplace for ethical business transitions. She also co-hosts the Ethical Exits podcast. WHAT YOU'LL LEARN: Why mission-driven founders belong on the buy side and not only the sell side, how shared values and trust can change a deal's structure and open the door to seller financing, how employee ownership and acquisition can work together, and how Steward Market uses values as searchable infrastructure so sellers can find a buyer by mission and hold period rather than valuation alone. HANNAH'S JOURNEY: Hannah grew up in Boise, Idaho, wanting to be a civil rights lawyer for the ACLU, studied political science, and came to see M&A as social and economic justice work because an ownership transition is a redistribution of power. She spent about 18 years in go-to-market and revenue roles before being asked in 2021 to run a corporate development team, where she learned that buying a company is just a different kind of sale. After that acquirer collapsed, she started her own firm expecting to do fractional sales work for B Corps. Instead, founders kept asking her to help them buy companies, and fractional corporate development was born. When she suggested that mission-driven founders could be acquirers too, they recoiled, which led her and her partner to launch Ethical Exits to explore what mission-driven M&A actually looks like. KEY INSIGHTS: Once you see the power of inorganic growth, you cannot unsee it as a lever. The real question is not whether acquisition is good or bad, but what you point it at. Values are a real deal variable. When a buyer and seller genuinely share goals and build trust, sellers become more open to seller financing and less fixated on all cash or the highest multiple. Employee ownership and acquisition can reinforce each other. Hannah points to a social work company that converted to an ESOP, acquired other firms, and began cutting checks north of a million dollars to retiring social workers. An ethical exit is not a partisan idea. Yvon Chouinard put Patagonia's purpose into a trust, and Eddie Smith turned down offers north of four hundred million dollars for Grady White because, as he put it, the company has a soul. The two men likely sit at opposite ends of the political spectrum. Real freedom is reciprocal. Wealth and ownership expand a person's power to make consequential decisions, and for Hannah that increases obligation rather than removing it. Perfect for founders weighing a sale, would-be buyers who assume the buy side is not for them, and advisors who want the deals they work on to protect more than price. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/hannahsandmeyer FOR MORE ON HANNAH SANDMEYER: Website: https://stewardmarket.com LinkedIn: https://www.linkedin.com/in/hannahsandmeyer Podcast: Ethical Exits, https://ethicalexits.com FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:02] - Introduction to Hannah Sandmeyer and the intersection of M&A and mission  [05:44] - Hannah's first capital raise in fifth grade with a chess team coupon drive [12:06] - Landing in corporate development in 2021 and a billion-dollar growth-by-acquisition model[16:30] - Starting her own firm and the birth of fractional corporate development [27:32] - Patagonia and Grady White as models of the ethical exit [38:03] - The Three Legged Stool employee ownership and acquisition story [46:07] - How Steward Market works as a three-sided marketplace [01:01:11] - What freedom means to Hannah Guest Bio Hannah Sandmeyer is the founder and CEO of Up and Over Advisors, the first certified B Corporation in the world dedicated exclusively to values-aligned M&A sourcing, and the founder of Steward Market, a live marketplace for ethical business transitions. She also co-hosts Ethical Exits, a podcast exploring how ownership transitions can protect mission, workers, culture, and community. A former Peace Corps volunteer turned M&A operator, Hannah works at the intersection of ownership, capital, and moral courage. Based in Portland, Oregon, she is an avid cyclist raising a preteen and a chicken named Greta who believes she is a dog. Related Episodes Episode 325 - Kelly Finnell: How Employee Stock Ownership Plans Actually Work. A deep look at ESOPs as an exit and succession tool, and how employees become owners. Episode 293 - Sunny Vanderbeck: Building and Selling a Company Without Treating Profit and Purpose as Enemies. Conscious capitalism and value creation over short-term profit. Episode 366 - Jodi Hume: Founder Exits and the Emotional Journey Behind Major Business Decisions. The psychological weight of selling and what founders need to prepare for beyond the transaction. Keywords/Tags ethical exits, values-aligned M&A, B Corp, employee ownership, ESOP, stewardship ownership, mission-driven acquisitions, seller financing, deal structure, Steward Market, Up and Over Advisors, three-sided marketplace, buy side, legacy preservation, mission continuity, conscious capitalism

    Episode 423: Making M&A a Force for Good with Hannah Sandmeyer
  2. Sep 23

    Episode 422: Alternative Ways to Fund a Business with George Dubec

    When George Dubec and his wife sold the largest singles network in South Florida in the early nineties, the buyer was another matchmaking firm looking to expand into events. What they were actually paying for was the database. "They couldn't replicate me and my wife as the face of the business," George says. Nearly forty years later, that lesson still drives how he advises business owners. George Dubec is considered one of the top business and social networking experts in the United States. He began his career as an engineer, rising to executive staff at Packard Electric, a division of General Motors, before moving to Florida in 1985 to build companies of his own. He has hosted radio and TV programs including the Internet Business Hour, has judged the Web Awards since 2006, and now serves on the advisory board of America's Real Deal, a business investment television show. WHAT YOU'LL LEARN: How business owners can access capital outside the standard fundraising path, including tax credits, tax refunds, and legal settlements that already belong to them. Why a customer database may be the most saleable asset a company owns. How fractional deals, crowdfunding platforms, and crypto-based sweeteners are reshaping who can invest and who can raise. And why a two to five minute pitch video now opens more investor doors than a polished deck. GEORGE'S JOURNEY: George grew up in Boardman, Ohio, in a town he compares to Happy Days, where he saw the first television set in the neighborhood and the phones were still party lines. He was the first person in his family to graduate from college, attending Youngstown State University. He spent roughly eighteen years at General Motors as an engineer before buying his job out and relocating to South Florida in 1985. With his wife he built the largest singles network in South Florida, running it from 1985 until about 1992, before online dating existed. After selling, he moved into the early web with a company called Webstream, hosting sites, then building them, then adding search engine optimization. He launched the Internet Business Hour radio show in 1998 and ran it for about twelve years. He technically retired from the company in 2010 and shifted into alternative funding work with business owners. KEY INSIGHTS: Data is the asset owners undervalue. The buyer of George's first company wanted the list, not the events. He now maintains a database of forty thousand clean email addresses and tells owners to build one, because it can generate revenue long before an exit and may be what a buyer is actually purchasing at the exit. There is money most owners never look for. George describes himself as an alternative funder, helping business owners recover capital through tax reimbursements, tax credits, tax refunds, and legal settlements. As he puts it, going out with a pitch deck and asking for money is really tough, and most owners stop at the one channel they already know. Widened access comes with a vetting problem. Alternative investments were once closed to all but the wealthy. Opening them up has real benefits, but George is candid that many of these platforms have two or three years of history and no track record to evaluate. "It's kind of like the wild frontier. It's like digging for gold." The pitch video is the new front door. Investors are buried in decks and one-pagers they do not have time to read. George recommends a two to five minute video of you and your principals as the thing that earns the deck a read. What investors are assessing in those minutes is whether the person pitching has the attitude, moxie, and experience to make it work. Freedom requires a system. Asked what freedom means to him, George argued that eleven superstars who each do their own thing will never win a football game. "You gotta find a system that suits you, that you can be free in the system." Perfect for business owners who have been told that bootstrapping and venture capital are the only two real options for funding growth.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/georgedubec FOR MORE ON GEORGE DUBEC:  https://theultimatenetworker.com  https://techunfilteredagi.com  https://www.americasrealdeal.com  FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps[02:17] Growing up in a no-tech Ohio town and seeing the neighborhood's first television set[06:36] Eighteen years at General Motors, buying his job out, and starting the largest singles network in South Florida[09:07] Selling the business and why the buyer was really after the database[13:43] Crypto coins as an investor sweetener, fractional deals, and other funding paths outside the usual channels[25:00] The four ways companies get funded on America's Real Deal, from sharks to a private stock exchange[26:23] Why a two to five minute pitch video matters more than the deck[44:27] Freedom inside a system and the football team analogy Guest Bio George Dubec is a business and social networking expert based in South Florida. After roughly eighteen years as an engineer at Packard Electric, a division of General Motors, he moved to Florida in 1985 and co-founded the largest singles network in South Florida with his wife, operating it until the early nineties. He then entered the early web industry with Webstream, working in hosting, web development, and search engine optimization, and launched the Internet Business Hour radio show in 1998, which he hosted for about twelve years. He has judged the Web Awards since 2006. Today he works with business owners on alternative funding sources, serves on the advisory board of the business investment show America's Real Deal, and hosts a new podcast called Tech Unfiltered. He is writing a book titled How to Thrive and Survive in the New High-Tech AI World. Related Episodes Episode 350 with Tom Dillon covers when not to take venture capital money and walks through alternative funding sources including private credit, SBA loans, term loans, and sale-leasebacks. It pairs directly with George's argument that most owners default to one channel and stop. Episode 370 with Gerry Hays examines democratizing access to early-stage investing through very small stakes, which speaks to the same tension George raises between widening access and protecting less experienced investors. Episode 351 is a solocast where Corey explores deal structures beyond mergers, acquisitions, and capital raising, including joint ventures, strategic alliances, and licensing agreements. A useful companion for owners looking to grow without a traditional raise. Keywords/Tags alternative business funding, tax credits for business owners, tax refunds, legal settlements, pitch video for investors, America's Real Deal, crowdfunding, Start Engine, WeFunder, fractional investing, private stock exchange, accredited investors, customer database value, business exit, authority marketing, personal branding, podcasting for business, AI agents, networking, deal-driven growth, DealQuest Podcast, Corey Kupfer, George Dubec

    Episode 422: Alternative Ways to Fund a Business with George Dubec
  3. Sep 16

    Episode 421: How to Vet a Franchise Deal with Matt Stevens

    Matt Stevens walked away from his first closing table controlling two duplexes, having put nothing down, holding a check for forty seven hundred dollars. That deal taught him that things he assumed were impossible were actually available to him, and it started a career built on reading structure before reading price. Known as The Franchise Guy, Matt has more than 30 years in the franchise industry and has sat in nearly every seat at the table. He has been a franchisee, a franchise coach, a franchisor, and now a franchise consultant. He was rookie franchisee of the year, turned around struggling divisions, and served as a board member and partner inside a two billion dollar franchise group. WHAT YOU'LL LEARN: How to evaluate a franchise opportunity beyond the investment number, why first rights of refusal have essentially disappeared from franchise agreements, how territory math changes the economics of multi-unit ownership, the behavioral due diligence most candidates never perform on themselves, and where the real growth is happening in franchising right now. MATT'S JOURNEY: Matt got into franchising by reading an advertisement on a hallway wall at Wake Forest University. He joined the business that became CertaPro Painters when there were only 67 operators across Canada, New England, and the Mid-Atlantic. The deal had a zero dollar investment to get in and a 25 percent royalty on the back end, a trade both sides made deliberately. He spent about ten years in that system, moving from operator to coach to the franchisor side. Before franchising, Matt spent nearly two decades in rental property, building to 14 units before selling his last property in 2017. Over one six year stretch in franchising, he found, recruited, signed, trained, and mentored 167 franchise owners across nine states in a single system. Today he helps candidates cut through franchise marketing using non-public research on franchisors, their development teams, and their existing owners. KEY INSIGHTS: Every piece of human behavior is driven by inputs and outcomes rather than rationale or common sense. Matt was frustrated by several franchisor decisions when he was an owner. Once he became a franchisor, those same decisions made complete sense. His advice to candidates is to assume every rule exists for a reason and to ask why. First rights of refusal on territory used to be common in franchising and are now essentially gone. Matt's read is that the only reason a franchisor offers one today is that they are desperate to sign that candidate. What replaced it is a growth schedule tied to what an operator can realistically execute. Territory secured early is what Matt calls growth insurance. One territory costs X, three cost roughly 1.6X, and five cost roughly 2.2X, and six territories can be serviced with the same phone number and van as one. In fast moving markets, what is available today will not be available later. The hardest due diligence is the kind candidates perform on themselves. Investment and territory are confirmable. What is not confirmable is whether a person will replicate the daily behavioral patterns the system requires. One of Matt's screening questions is how long a candidate can go at zero income before hitting the panic button. The least appreciated opportunity in franchising is the mundane service business. Matt's framing is that in a market with 400 competitors within 30 miles, you are not competing against 400 companies. You are competing against the two others the customer called. That is how he became the largest buyer at his Sherwin Williams store in Keene, New Hampshire by May of his first year in the painting business at age 20. Perfect for anyone weighing franchise ownership, operators planning multi-unit growth, and dealmakers who want to see how structure and price get traded against each other in a real agreement.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/mattstevens FOR MORE ON MATT STEVENS: https://heisthefranchiseguy.com  https://podcast.heisthefranchiseguy.com/DQ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [03:26] - The first deal, two duplexes controlled with nothing down and a check at closing [14:14] - Why first rights of refusal disappeared and what it means when one is offered [21:14] - The behavioral due diligence candidates skip and the four Ds [31:43] - What separates successful franchisees, including the ABS framework[47:44] - What freedom means to Matt Guest Bio Matt Stevens, known as The Franchise Guy, is a franchise consultant with more than 30 years in the industry. He has been a franchisee, a franchise coach, a franchisor, and a franchise consultant, and was named rookie franchisee of the year early in his career. He has turned around struggling divisions and served as a board member and partner inside a two billion dollar franchise group. Matt is a franchise gold and century club member, a Business First Columbus 40 under 40 honoree, and the author of a three hour course on thorough franchise review. He holds three business degrees from Florida Southern College and Wake Forest University and is a MENSA member. His process walks candidates from first conversation to confident decision using real world validation, insider questions, and practical coaching. Related Episodes Episode 329 - Cliff Nonnenmacher on master franchising and who is not a fit for the franchise model. A useful companion for understanding the layers of ownership between single unit franchisee and franchisor. Episode 333 - Greg Mohr on franchise agreements, protected territories, and how franchisors identify their ideal franchisee. Pairs directly with Matt's discussion of what franchisors assess in candidates. Episode 330 - Pete Mohr on owning and exiting multiple franchise businesses, including buying himself out of an agreement that was not working. Offers the operator's view of what happens when the fit turns out to be wrong. Episode 336 - Devan Gonzalez on building an emerging fitness franchise from the franchisor side, which connects to Matt's read on growth in health and wellness. Keywords/Tags franchise consulting, buying a franchise, franchise due diligence, franchisee validation, franchise territory rights, first right of refusal, right of first offer, franchise royalty structure, multi-unit franchising, home services franchise, health and wellness franchise, deal structure, business ownership, entrepreneurship, DealQuest Podcast, Corey Kupfer, Matt Stevens, The Franchise Guy

    Episode 421: How to Vet a Franchise Deal with Matt Stevens
  4. Sep 9

    Episode 420: How to Make a Business Partnership Work and Exit Well with Corey Kupfer

    A business partnership is often the first deal an entrepreneur ever does, long before any M&A or capital raise. In this solocast, Corey Kupfer steps back from the usual deal categories to talk about what it actually takes to be in a partnership, drawing on his own partnerships across multiple businesses and decades of helping clients form, evolve, and separate theirs. Corey Kupfer is an attorney, dealmaker, and negotiator with more than 35 years of experience. Beyond drafting the documents for new partnerships, he has guided partners through evolution, buyouts, and separations, and he serves as a mediator for partners working to part ways well. WHAT YOU'LL LEARN: This episode covers the due diligence founders most often skip, how partnerships fall out of alignment over time, what a partnership agreement can and cannot protect, why no employee ever matches an owner's commitment, and how to separate through a negotiated exit rather than a costly fight. COREY'S PARTNERSHIP JOURNEY: Corey has been in several partnerships over the years, starting with a law firm partnership formed in the 1990s that ended over economic differences and a different view of perceived value, then reconnected warmly with those partners decades later. He also built a real estate investment partnership with his partner Dan that stayed strong through the great recession because of aligned values and superb communication. His last partnership ran from 2010 to 2015 and ended in a difficult split over vision, values, and culture. Even so, that chapter deepened his work in the RIA space and introduced him to clients and colleagues he values to this day, a reminder that even partnerships that end can create lasting good. KEY INSIGHTS: The personal and cultural due diligence matters most and gets skipped most. Even when you already know someone well, you still need an honest conversation about this specific venture, your shared vision and values, and your goals and timelines. Partnerships evolve because the business, the people, and the market all change. Following where clients and the market lead is usually smart, but that evolution can pull one partner into alignment with a new direction while leaving the other behind, even when they started out aligned. The agreement is a roadmap, not a guarantee. An operating agreement or shareholders agreement can set the methodology for a split or buyout, but whether partners actually stay together comes down to trust, respect, communication, and a willingness to evolve. Litigation is rarely the best way to separate. The damage to the business, clients, and employee retention often means everybody loses, and the opportunity cost of the distraction is something people almost never calculate. A partnership is one deal type among many. Go in eyes wide open, get as clear an agreement as possible upfront when you cannot yet know who it will affect, and keep checking whether the partnership stays in alignment and integrity for you. Perfect for entrepreneurs weighing a partnership, founders navigating a separation, and anyone who wants to structure the deal before there is anything to fight about.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/businesspartnerships FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/  Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00] - Why business partnerships are often the first deal an entrepreneur ever does [03:28] - The due diligence you owe yourself, even with friends and family [07:33] - How partnerships and the people in them grow apart over time [09:20] - A PR firm buyout and an operator versus developer split, when growing apart is nobody's fault[13:44] - Corey's own partnerships, from a 1990s law firm to real estate with Dan to the 2010 to 2015 split[19:46] - Why no employee ever matches an owner's commitment, and why it can still feel good to be the only decision maker[23:32] - Building a clear agreement on decisions, economics, and the what ifs[25:57] - Separating well, opportunity cost, and the CPR process from Authentic Negotiating Host BioCorey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. He is an entrepreneur, attorney, consultant, author of Authentic Negotiating, and professional speaker whose firm helps clients structure business partnerships, joint ventures, mergers and acquisitions, and capital raises. He is the creator and host of the DealQuest Podcast. Related EpisodesEpisode 351 - Solocast 77: A solocast breaking down joint ventures, strategic alliances, and the exit provisions that work like a partnership prenup. Episode 336 - Devan Gonzalez: A real world business partnership where the partners set up a clear conversation to keep friendship and business separate. Episode 366 - Jodi Hume: The emotional dimensions of exits and the decisions founders face when it is time to move on. Keywords/Tagsbusiness partnerships, partnership due diligence, vision and values alignment, operating agreement, shareholders agreement, buyout, negotiated exit, partnership separation, opportunity cost, mediation, authentic negotiating, CPR framework, entrepreneurship, deal-driven growth, DealQuest Podcast, Corey Kupfer

    Episode 420: How to Make a Business Partnership Work and Exit Well with Corey Kupfer
  5. Sep 2

    Episode 419: Walking Away From a Silicon Valley Buyout with Brad Kugler

    What if the smartest deal of your career was the buyout you refused to close? That is the call Brad Kugler made when a Silicon Valley firm tried to acquire his marketing platform. The original offer valued his company at roughly 19 times profit, but when the buyer cut it 20 percent late in the process, Brad ended the deal, and thirty months later he has no regrets. Brad is the CEO of Direct Mail 2.0, Who's Mailing What, and DM20.ai, and a serial entrepreneur with more than 35 years of building businesses through constant change. Brad grew a VHS distribution company from a million dollars to 25 million before streaming rode it back to zero, an experience he says taught him more on the way down than on the way up. He carried that hard-won judgment into every deal that followed, including a full acquisition process with Symphony Technology Group that he ended when the buyer used a churn recalculation to cut the offer 20 percent. For Brad, the freedom to run his own company outweighed the cash, the culture mismatch, and three years under a private equity group. But Brad is far from deal-shy. He acquired Who's Mailing What, a direct mail intelligence platform running since 1984, for 20 percent below asking price, grew its revenue by 50 percent, and used its four-decade database as the foundation for DM20.ai. That tool runs three frontier AI models against each other to predict how a direct mail campaign will perform, all for about 50 dollars. With his core market shrinking, a printer list that fell from more than 11,000 names to 3,600 in nine years, Brad now grows by acquisition and joint venture rather than fighting for share in a capped market. For any entrepreneur weighing an exit, an acquisition, or a raise, this conversation offers a grounded look at how self-awareness shapes better deal decisions at every stage of a career.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com FOR MORE ON BRAD KUGLER: Website: https://www.dm20.com LinkedIn: https://www.linkedin.com/in/bradkugler/ FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:03] - Introduction[03:54] - A VHS business from a million to 25 million to zero [11:24] - The 19x offer and the culture red flags [13:14] - Why he walked away [17:10] - A friend's exit and what money cannot buy [27:08] - Acquiring Who's Mailing What  [38:16] - Growing by acquisition in a shrinking market [47:44] - What freedom means to Brad Guest Bio Brad Kugler is the CEO of Direct Mail 2.0, Who's Mailing What, and DM20.ai, three brands under one company dedicated to helping marketers and commercial printers get better results from direct mail. A lifelong entrepreneur and innovator with more than 35 years in business, Brad combines data, technology, and market intelligence to help businesses make smarter marketing decisions and uncover new growth opportunities. He grew a VHS distribution company from a million dollars to 25 million earlier in his career, and today he is focused on inorganic growth through acquisitions and joint ventures while building AI-driven tools for the direct mail industry.Keywords/Tags direct mail marketing, marketing technology, walking away from a deal, buy versus build, strategic acquisition, proprietary data, AI in marketing, DM20.ai, Who's Mailing What, growth by acquisition, joint ventures, shrinking market strategy, later-stage entrepreneur, exit strategy, self-awareness in business, deal-driven growth, Brad Kugler, DealQuest, Corey Kupfer

    Episode 419: Walking Away From a Silicon Valley Buyout with Brad Kugler
  6. Aug 26

    Episode 418: No Cash, No Credit Real Estate Deals with Zachary Beach

    Zachary Beach bought his first house for little more than closing costs. The seller was mid-divorce and could not make the next payment, so Zach took title subject to the existing loan and later sold it on rent to own. That messy first deal came together as about a seventy thousand dollar deal and broke him into the industry. Zach went from bartending to his father in law's real estate business at twenty five and has since completed or advised on over a thousand deals. He is the CEO of Smart Real Estate Coach and a three time best selling co-author of Real Estate on Your Own Terms, The New Rules for Real Estate Investing, and Sell with Authority for Real Estate Investors. WHAT YOU'LL LEARN: How to structure creative real estate deals with no cash, no credit, and no banks, why implementation beats knowledge, how the three paydays system turns one property into three income streams, and how those same skills scale into acquiring companies. ZACHARY'S JOURNEY: Zach did not grow up around entrepreneurship or financial literacy. His first transaction was selling golf balls three for a dollar as a kid, and his real estate company is named Watch Street after the block where he picked them. After burning out on bartending, he joined his father in law's old-school, paper-heavy business and built the systems that became Smart Real Estate Coach, now a real estate investment company disguised as a coaching company with deals in more than eighty markets. KEY INSIGHTS: Creative financing is a people business first. Zach carries multiple tools, including seller financing, subject-to, and lease purchases, and matches each to the seller's problem instead of throwing away most of his leads. The three paydays system is the core model. A property sold on rent to own generates a deposit up front of three to ten percent, monthly cash flow, and a future cash-out from a built-in buyer. Rent to own only works when it is set up right. Zach would criticize ninety nine percent of rent-to-owns himself, which is why his team runs a quasi-underwriting process and credits the down payment toward the purchase price. Perfect for W-2 employees seeking a way out, burned-out investors watching the traditional model stop penciling, and operators exploring acquisition-driven growth.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/zacharybeach FOR MORE ON ZACHARY BEACH: LinkedIn: https://www.linkedin.com/in/zacharyrbeach Facebook: https://www.facebook.com/ZRBeach/ Company: https://smartrealestatecoach.com Free books offer: https://3paydaysbooks.com/dealquest FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:03] - Introduction and Zach's path from bartender to real estate dealmaker [08:38] - The first real estate deal, a subject-to purchase on a roughly $180,000 property [22:55] - The biggest mistake investors make and why implementation beats knowledge [32:56] - The three paydays system and how creative financing creates three income streams [36:15] - Addressing the rent-to-own criticism and the quasi-underwriting process [43:12] - The integrity real estate roll-up and acquiring elite educators Guest Bio: Zachary Beach is the CEO of Smart Real Estate Coach and a partner in multiple seven figure businesses. He went from bartending and personal training into his family's real estate business at twenty five, and has since completed or advised on over a thousand deals using creative financing strategies including seller financing, subject-to, and lease purchases. He is a three time best selling co-author of Real Estate on Your Own Terms, The New Rules for Real Estate Investing, and Sell with Authority for Real Estate Investors, and he co-hosts the Smart Real Estate Coach and Not Just the Transaction podcasts. He mentors students across the country and is building an integrity-focused real estate coaching roll-up. Related Episodes: Episode 191 - Jack Bosch: Building a real estate education business on real deal experience. Bosch's path from investor to educator parallels how Smart Real Estate Coach teaches from actual transactions. Episode 183 - Kent Ritter: How to invest in real estate. Ritter's emphasis on consistent execution over big promises reinforces Zach's point that implementation is what separates successful investors. Episode 332 - John Martinka: Buying businesses and the dynamics of roll-ups. A useful companion for Zach's acquisition strategy and the difference between aggregating for size and adding real value. Episode 293 - Sunny Vanderbeck: Serial acquisition, roll-ups, and building a repeatable deal program. Relevant context for anyone thinking through an acquisition-driven growth model. Keywords/Tags: creative real estate financing, subject-to deals, rent to own, no money down real estate, three paydays system, seller financing, lease purchase, real estate coaching, Smart Real Estate Coach, Zachary Beach, W-2 to entrepreneur, real estate roll-up, real estate acquisitions, deal-driven growth, DealQuest Podcast

    Episode 418: No Cash, No Credit Real Estate Deals with Zachary Beach
  7. Aug 19

    Episode 417: From Nine Rejections to Two IPOs with Babu Sivadasan

    What if the job you almost didn't get became the foundation for building two public companies? That's exactly what happened to Babu Sivadasan, who was rejected by nine firms before landing his first job out of college, a job he still calls the best deal he ever made. Babu is a serial entrepreneur and engineer who co-founded stamps.com and later co-founded Envestnet, two category-defining platforms in commerce and wealth management technology. He's now the founder of Jiffy AI, applying artificial intelligence to how software gets created and deployed. In this episode, Babu traces a 1990s patent that became stamps.com, a demo computer damaged in his suitcase before a make-or-break Postal Service pitch, and an accidental pivot into wealth management that led to Envestnet. He also shares why he believes natural language will replace traditional programming, and how that belief now drives Jiffy AI. Whether you're weighing whether to raise capital or curious how AI is reshaping wealth management technology, this conversation offers a rare, three-decade view of how founders build through very different technology eras.WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com FOR MORE ON BABU SIVADASAN: https://www.jiffy.ai  FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [02:20] - Rejected by nine firms before landing his first job [05:17] - The 1990s patent that became stamps.com [13:19] - A damaged demo computer and a make-or-break Postal Service pitch[25:15] - The accidental pivot into wealth management [32:41] - Unifying a fragmented advisor tech stack at Envestnet [54:06] - Jiffy AI today: Series B funded, $61 million raised Guest Bio Babu Sivadasan is a serial entrepreneur with deep experience building and scaling public companies backed by a strong engineering foundation. He co-founded stamps.com and later co-founded Envestnet, helping shape category-defining platforms in commerce and financial services. He is now the founder of Jiffy AI, applying natural language AI technology to how software is created and deployed for the wealth management industry. Babu is also an active angel investor and mentor, supporting startups across Silicon Valley and India. Related Episodes Episode 328 - Richard Manders: a fellow engineer-turned-founder whose curiosity about how things work led him from an early career in automation to building and scaling multiple companies with private equity backing. Episode 370 - Gerry Hays: explores how collapsing startup costs and artificial intelligence are reshaping who can raise capital and become a founder, a theme that runs through Babu's own move from the cloud era into the AI era. Episode 350 - Tom Dillon: examines when founders should look beyond venture capital for funding, a question Babu faced directly in the cash-strapped early days of stamps.com.

    Episode 417: From Nine Rejections to Two IPOs with Babu Sivadasan
  8. Aug 12

    Episode 416: Deal Clichés Worth Questioning with Corey Kupfer

    "Give me a price, I'll give you a structure. Give me a structure, I'll give you a price." In this solocast, Corey Kupfer takes that favorite saying of his and uses it to unpack a handful of the deal world's most repeated cliches, testing which ones hold up and which ones only apply in certain situations. Corey has spent more than 35 years structuring and negotiating deals, and in this episode he draws on that experience to walk through what's really behind a purchase price, a valuation multiple, and a few tax and entity assumptions sellers often take as gospel. WHAT YOU'LL LEARN: Corey breaks down what actually makes up a deal structure, from escrow and promissory notes to earnouts and rollover equity, and why "give me a price, I'll give you a structure" is the question that should come before you get excited about a top line number. He also digs into why comparing multiples without knowing what they're calculated on is misleading, when the advice to take cash up front actually applies, and why he pushes back on the idea that most businesses can't be scaled or sold. KEY INSIGHTS: A purchase price is never just one number. Escrow holdbacks, contingent payments tied to retention, earnouts tied to growth targets, and rollover equity can all sit inside a single deal, and each one carries different risk and different timing. Multiples are almost never apples to apples. Most quoted multiples are calculated on adjusted EBITDA, and buyers can adjust that number differently, which means a higher multiple doesn't always mean a higher price. Take cash up front is better advice for Main Street, owner operator deals than it is for the middle market and up, where professional buyers and PE backed firms have more reputational reasons to pay what they owe. The S Corp regret Corey heard at an industry event traced back to a missed QSBS election, not to S Corps being universally worse. Entity structure decisions depend on industry, timing, and ownership goals, not blanket rules. Corey doesn't believe in unscalable businesses, only businesses that haven't found their systems yet. The same logic applies to sellability, most businesses that can't sell today can become sellable with the right changes. Perfect for entrepreneurs preparing for a sale, raising capital, or negotiating a licensing or royalty deal who want to ask sharper questions before they get anchored on a number.  WANT TO BE A GUEST ON DEALQUEST?Apply here: https://beaguestondealquest.com FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/dealcliches FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Episode Highlights with Timestamps:01:01 - The famous deal world saying, give me a price, I'll give you a structure, and why it matters 03:45 - What's actually inside a deal structure, escrow, promissory notes, and contingent payments 06:24 - Why comparing multiples without knowing what they're calculated on is misleading 09:08 - When take cash up front is real advice, and when it isn't 13:41 - The S Corp story from an industry event and the QSBS election behind it 16:45 - Why Corey believes every business is potentially scalable and sellable Related Episodes:Episode 328 with Richard Manders, for a deeper look at multiple arbitrage and how buyers think about valuation multiples. Episode 339 for more on purchase price structures, contingencies, and how retention and earnouts affect what a seller actually collects. Episode 325 with Kelly Finnell, for a related conversation on tax advantaged entity and ownership structures. Keywords/Tags: deal structure, purchase price negotiation, EBITDA multiple, adjusted EBITDA, earnouts, rollover equity, escrow, QSBS, S Corp versus C Corp, business sellability, business scalability, licensing royalties, M&A negotiation, DealQuest solocast

    Episode 416: Deal Clichés Worth Questioning with Corey Kupfer
4.9
out of 5
43 Ratings

About

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, partnerships, and strategic alliances, licensing, raising capital and onboarding key employees, negotiating, structuring, finding, valuing, closing and integrating deals. Don’t be the one at the table who doesn’t grasp the power of Deal-Driven Growth!

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