Smart Business Dealmakers

Perhaps the worst thing a business owner can do ahead of the sale of their company is not be prepared. Not only could that crater the returns the owner was hoping to get for what is often their life's work, it could nuke a sale entirely. Fortunately, attorney James Hipolit has advice for those who've never sold before. In this podcast, the M&A partner with Troutman Pepper Locke covers the basics, from first steps to pre-diligence to common pitfalls, offering advice to get first-time sellers off to a strong start.

One area of complexity in a buy-side M&A transaction is commercial insurance. Given all the potential liabilities, hidden risks, industry-specific needs and coverage gaps, knowing what to look for during due diligence is critical to maximizing post-deal value. On this episode, Brian Stovsky, senior vice president and practice leader for the Oswald Companies and Unison Risk Advisors Mergers & Acquisitions Practice, and Joe Curtis, vice president and director of benefits for Michigan at Oswald Companies, talk about buyer pre-and post-close M&A due diligence considerations of commercial insurance for risk management. 

At the 2025 Dallas Smart Business Dealmakers Conference, Zenwork Founder & CEO Sanjeev Singh shared the entrepreneurial journey that led to a nine-figure private equity minority investment. From launching Zenwork with his wife to scaling the business and bringing on a PE partner, Sanjeev discusses the challenges, pivotal moments and strategies that fueled Zenwork's growth.  

There are many myths about ESOPs — that they're complicated or that once within its structure a company owner loses control, or that banks won't lend to them. David Solomon, a member at Levenfeld Pearlstein and head of the firm's Employee Stock Ownership Plan practice, is here to bust those myths. In this episode, David sets the record straight on what an ESOP is — and what it isn't.

What happens when a publicly traded company transitions to become privately owned? During the midday Fireside Chat at the Boston Smart Business Dealmakers Conference, two CFOs share firsthand insights on the realities of life as a public company, the strategic considerations behind their respective sales to private equity firms, and what the transition process entailed. Cassandra Hudson, CFO of StackAdapt and former CFO of EngageSmart, and John Wagner, former CFO of Brightcove, sat down with Bank of America Managing Director Phil Ianniello to discuss what changed post-transaction and how the shift has impacted operations and financial strategy, and offer key lessons from navigating this major transformation.

A letter of intent, often referred to as an LOI, is essentially the first formal document in a sale process between a buyer and a seller. It not only establishes the intent of two companies to move forward into a sale process, but it sets some terms for the process that sellers should carefully consider. Tony Montanaro, transaction advisory partner with Louis Plung & Company, talks about LOIs and what sellers need to know about the terms within them before moving forward with a deal.

Kicking off this year's Boston Smart Business Dealmakers Conference, we explore innovative strategies, regional growth and the transformative power of public-private collaboration in shaping the future of Massachusetts and the Boston region. In this panel, moderated by Smart Business Chief Content Officer Dustin Klein, Timberline Construction CEO Steven Kelly and Commonwealth of Massachusetts Chief Digital Officer Janak Joshi explore the dynamic landscape of economic development in the state.

Things seem to be looking up for the St. Louis economy. And with positive national economic trends expected to continue, the city seems poised to build on its momentum. At the 2025 St. Louis Smart Business Dealmakers Conference, Dustin Allison of Greater St. Louis Inc., Rhonda Hamm-Niebruegge of St. Louis Lambert International Airport and John Manetta of Bank of America joined Bank of America St. Louis President Marilyn Bush to analyze the economic indicators, infrastructure developments and investment strategies shaping the city's future. 

What really makes a company tick? And more importantly, what makes it worth more? At the 2025 Pittsburgh Smart Business Dealmakers Conference, a group of regional executives and investors dissected the art — and science — of creating serious company value. From scaling strategies that turn small wins into big exits to the nuanced dance of acquisitions and sales, panelists John Lewis and Christopher Brodman of Metz Lewis Brodman Must O'Keefe, Rob Carskadden of 3 Rivers Capital, George Pilafas of Continuim Equity Partners and Patrick Patterson of Level Agency pulled back the curtain on what drives growth in today's deal-driven market.

Self-funding health insurance through a group medical captive can be a way for businesses of any size to better manage what is often their second greatest expense. And, according to Roundstone Founder and President Mike Schroeder, it may also be a way for business owners to increase the company's value ahead of a sale. On this episode of the Smart Business Dealmakers Podcast, Schroeder talks about the self-funding model as well as its impact on an M&A transaction.

Warde Manuel, University of Michigan's Donald R. Shepherd Director of Athletics, oversees an athletic department that sponsors 29 varsity teams with more than 950 student-athletes and around 400 staff members. To run it, the former collegiate athlete relies on more than just his 30 years of experience in athletic departments. Warde also leans on his MBA. In this episode of the Smart Business Dealmakers Podcast, sponsored by Old National Bank, the official bank of the Big Ten Conference, Warde talks about hiring top talent, maintaining culture, funding in the age of NIL, and how much running an athletic department is like running a business.

Dive into serial entrepreneur Matt Liotta's experience navigating mergers, acquisitions and public offerings with multiple companies. Liotta, the co-founder of Volato, a fractional jet company he took public through a SPAC, chats with Tom Singh of Merrill Lynch about the strategic decisions behind scaling Volato, as well as the lesson's he's learned about structuring deals, adapting business models, and maintaining innovation in a competitive market.  

What will be driving M&A as we head into to 2025? In this roundtable discussion at the Charlotte Smart Business Dealmakers Conference, Murphy Clark of Inspira Financial, Patty Comer of AccruePartners and Greg Fornelli of SRI and Stock Car Steel & Aluminum talk with First National Bank's David Sedor about the drivers behind valuations, assessing and retaining talent during an acquisition, how interest rates are impacting M&A, and more.

Social media, believe it or not, can have an effective role in the world of venture capital. At the Houston Smart Business Dealmakers Conference, Carrie Colbert of Curate Capital, Aquila Mendez-Valdez of Haute in Texas and Darek Woodward of ROI Ventures talked with Smart Business's Dustin Klein about how to craft a captivating online brand that attracts investors, builds a thriving community of future deal flow, and uses influencers to skyrocket the value of your investments. 

Name Image and Likeness rules have changed the game in college athletics. With more money needed to attract and retain the country's top talent, private equity and other firms are looking to bridge the financial gap and capitalize on the evolving landscape.  At the 2024 Minneapolis Smart Business Dealmakers Conference, panelists Blake Baratz of IFA, Katie Harms of Space Options, Cale Johnston of Roy Inc. and Gabriel Szerda of AB CarVal discuss the business future of college sports with moderator Steve Kozachok of Taft, offering insights into the trends and complexities driving this dynamic market. 

Colorado is emerging as a national hub for biotech, life sciences, and healthtech. At the 2024 Denver Smart Business Dealmakers Conference, panelists Elyse Blazevich of Colorado BioScience Association and Colorado BioScience Institute, Kimberly Muller of CU Innovations and CU Healthcare Innovation Fund, Afshin Safavi of Colorado Health & Tech Centers, and Blake Unterreiner of Agilent Technologies explored the flow of capital into the state, the success of innovative businesses, and the groundbreaking technologies spun out of universities. Moderated by Dustin Klein of Smart Business, they showcase the forces propelling Colorado to the forefront of the industry and what's expected in the coming years.

At the 2024 Chicago Smart Business Dealmakers Conference, midday keynote speakers Andrew Berlin of Shield.AI, Berlin Packaging, Chicago Cubs and South Bend Cubs, along with Rob Sine of Blueprint Sports, talked with Smart Business Network's Dustin Klein about how strategic opportunities in asset diversification and the current economic climate are reshaping the landscape for athletes, institutions and franchises. 

A recent Federal Trade Commission rule aimed to prohibit employers from attempting to enter into non-competes with all workers. Though that rule might never take effect, state-level trends governing the use of non-competes leave plenty for businesses and dealmakers to navigate. Royer Cooper Cohen Braunfeld partners Matt Brinker and Alex Nasser break down the trends and offer advice on how M&A professionals can prepare and structure deals in the current environment.

With a presence in 36 cities and 20 states, zTrip has become the largest taxi fleet operator in the U.S. largely through acquisition-driven growth. With a remarkably refined deal strategy and new insights from a passed-over SPAC opportunity, the company is now competing with the country's most recognizable ridesharing companies. Founder and CEO Bill George talks about the genesis of the business, its acquisition process and the secret sauce that's helping the company continue on its extraordinary trajectory.

While we're still arguably in a period rife with challenges, there seems to be a more positive sentiment forming — not enough that everyone in the M&A environment is happy, but maybe enough to signal that the deal market is ready to turn the page. At the inaugural D.C. Capital Region Smart Business Dealmakers Conference, Debbie Ricci of Guidehouse, Don Bassell formerly of ARKO, Alex Shahidi of Riveron and Chris O'Geen of Wells Fargo, on a panel moderated by Riveron's Robert Berdanier, explore today's market conditions and what it all means for executives looking to get deals done.

In some ways, when looking out into the deal environment, it seems as if uncertainty will be the only certainty. With the instability a constant challenge, both buyers and sellers are trying to determine how best to prepare for the unexpected, which is all that can be expected. Brady Ware Advisory Group Practice Leader Jon DeMoss and Shareholder Eric Carter offer their take on the current market and how dealmakers can capitalize on opportunities despite the obstacles. 

Why would anyone do business in Columbus? Well, if you ask the panel of experts who kicked off this year's Columbus Smart Business Dealmakers Conference, there's a lot of reasons. Industry leaders Dr. Linda Lehmkuhl of MedVet, Aaron Weir of CollisionRight, Kim Zavislak of KPMG, Katie Bishop of J.P. Morgan Private Bank and moderator Leslie Johnson of Ice Miller discuss the opportunities they see in Central Ohio and how they are attacking the challenges of expanding in a city on the rise.

The past few years have been dynamic for M&A. Rising interest rates, inflation and a host of other issues have brought uncertainty across numerous sectors. But still, deals are getting done. Kicking off the 2024 Philadelphia Smart Business Dealmakers Conference, Bank of America's Jim Dever and Fritz Franz, Archetype Solutions' Chetan Bagga, PeopleShare's Ryan Clark and SeventySix Capital's Chad Stender share their experiences operating in this market and discuss what it takes to get M&A deals done in today's environment. 

Akron-based accounting and business advisory firm Apple Growth Partners is set to merge with Fargo, N.D.-based Eide Bailly. AGP — which through a strategic effort by Chairman Chuck Mullen grew to become the 18th-largest accounting firm in Ohio —will see its 24 partners and 125 staffers join Eide Bailly's 3,800-person team. Chuck and tax principal Jeff Brooks talk about the deal and all that's led to it — from both joining AGP after its acquisition of Brott Mardis back in 2008, to how their recent conversation about ChatGPT ultimately sparked the firm's sale.  

There are unique challenges and opportunities to running a closely held or family-owned business and having an effective board. At the 2024 Pittsburgh Smart Business Dealmakers Conference, four entrepreneurs shared tips and insights on how to present effectively to boards, emphasizing the importance of storytelling, simplicity and prioritizing critical information. The panelists also emphasized the importance of diversity, strategic focus and proactive management in effective board governance. The participants were Joe Cardosi, Meredith Meyer Grelli, Jason Wolfe and moderator Patrick Colletti.

At this year's Cleveland Smart Business Dealmakers Conference, regional leaders David Gilbert from the Greater Cleveland Sports Commission and Destination Cleveland, Greg Harris from the Rock & Roll Hall of Fame and Brian Zimmerman from the Cleveland Metroparks discuss how their innovative strategies have transformed Cleveland into a powerhouse for major sports events, scenic parks, and arts and culture. In this roundtable discussion led by First National Bank's Boyd Pethel, they highlight how their collaborative efforts drive economic growth and position the region as a must-visit destination for tourists, sports enthusiasts, and cultural aficionados alike.

The past few years have been volatile, with rising interest rates, inflation, and lots of uncertainty affecting the M&A market. At the New York Smart Business Dealmakers Conference, Bank of America's José Tavarez leads a conversation with Revel's Frank Reig, ChargeLab's Shaun Stewart and Bank of America's Shawn Hoyer on what dealmakers can expect for the remainder of 2024 and beyond.

Tariq Farid built Edible Brands from a single store in 1999 into a flourishing franchise empire that today has nearly 1,000 stores. Now he and his daughter, Somia Farid Silber, who is also now Edible's president, are rebranding, expanding and plotting the company's future. At this year's Atlanta Smart Business Dealmakers Conference, the two sat down with Tom Singh, a managing director and senior resident director with Merrill Lynch Wealth Management, to discuss the company's founding, flourishing and future.

There was a sharp decline in dealmaking during 2023 as the post-pandemic boom subsided and uncertainty intensified. Louis Plung & Company Partner Tony Montanaro joins the pod to discuss the factors influencing this change, how transactions are being affected, and what preparations sellers can make to have the best outcome in 2024 and beyond.

Robert Anderson Jr. served more than 20 years in the FBI, overseeing criminal and cyber investigations worldwide, including the Edward Snowden investigation. After the FBI, he served as managing director for a global organization helping companies respond to and recover from thousands of data breaches, as well as evaluate M&A target companies for cybersecurity vulnerabilities. The now Chairman and CEO of Cyber Defense Labs sat down with Smart Business Chief Content Officer Dustin Klein at the Dallas Smart Business Dealmakers Conference to discuss a range of issues, from Anderson's transition to the boardroom to his insights for business leaders on the evolution of cybersecurity threats.

The 2024 Boston Smart Business Dealmakers Conference featured a one-on-one conversation with Howard Brodsky, founder of CCA Global Partners, a groundbreaking $14 billion company. In this excerpt, he talks with Smart Business Chief Content Officer Dustin Klein about the common traits of the some of the world's most successful entrepreneurs, as well as the outsized impact delivering the unexpected can yield for a business.

Serial entrepreneur Todd Boyman has been a consumer of plant-based foods for more than three decades. So it shouldn't be a surprise that his business passion and food passion would eventually combine in a new venture. Hungry Planet is a maker of plant-based meats with fewer calories and less fat than conventional meat and other plant-based options. In March of 2023, Todd spoke at the St. Louis Smart Business Dealmakers Conference about his experiences launching Hungry Planet, its growth plans and his thoughts on building strong organizations.

Over 18 years and more than $15 billion in transactions, DGP Capital's Jack Chang has been advising businesses public and private on how to get the most out of their business when it's time to sell. He brought that experience to bear when he joined  us to talk about what sellers can do to make their business attractive to buyers, when they should start the process and who they can turn to for help as they work to maximize their deal.

Rob Hale thinks he's an unlikely person to listen to when it comes to dealmaking. After all, he became a billionaire and lost it all by the age of 35. But Rob rebounded from the failure of Network Plus to co-found Granite Telecommunications, which made him a billionaire again and eventually co-owner of the Boston Celtics. That failure and rebound yielded three essential business lessons that Rob shared with attendees at the 2023 Boston Smart Business Dealmakers Conference.

Human capital and corporate culture play a key role in most M&A transactions. In this episode, we talk to a different sort of business leader about asset management, team building and creating a winning culture — in a very literal sense. Nic Barlage is CEO of Rock Entertainment Group and its many holdings, including the NBA's Cleveland Cavaliers. He oversees more than 500 full-time team members throughout the business operations of the Cavaliers. Nic sat down with Smart Business Chief Content Officer Dustin Klein to discuss talent acquisition and development, building a winning culture, and the importance of leadership. What follows are excerpts from that conversation, which took place in June 2023 at the Cleveland Smart Business Dealmakers Conference.

Jumpstart Capital founder and Managing Partner Vic Gatto has been investing in early-stage health care businesses for nearly a decade. His organization — Jumpstart Foundry, Jumpstart Health Investors and Jumpstart Capital — works to bring innovation to what could be considered a timid but also complex industry. He talks about the formation and evolution of the venture capital firm, the opportunities he's seeing in these early-stage ventures as well as their challenges.

Carrie Thome left the Wisconsin Alumni Research Foundation, where, as the Chief Investment Officer, she oversaw a $3 billion investment portfolio, to co-found NVNG Investment Advisors, an investment platform and network made up of a family of funds. The organization closed its Fund 1 in late 2021. Carrie talks about the organization, leaving WARF to launch it, her experience as a fund raiser and the progress NVNG has made since its start in 2019.

Compelled by the invitation of Jesus to "love our neighbors as we love ourselves," Corner to Corner was founded by Will and Tiffany Acuff in 2011. The young couple wanted to create a relationship-centered nonprofit that focused on seeing neighbors in their low-income Nashville neighborhood flourish on their own terms. In partnership with the community, the first program was aimed at equipping those recently out of prison with the necessary skills to gain meaningful employment. Since those early days, Corner to Corner has grown and expanded programming throughout Middle Tennessee, all in meaningful partnership with neighbors. Will sat down with Smart Business to discuss how it all started, how he raised funds and what the future holds for Corner to Corner.  

Patrick Patterson went from the third person at what ultimately became Level Agency to its co-owner, sitting in the CEO seat for the first time. And shortly after taking over the business, he brought in PE partners — also a first — to help accelerate the company's growth with M&A-minded advisers who can help the agency accomplish its ambitions goals. Patrick talks about the management buyout, how he connected with his PE backers and what it took to close the deal, what life is like with a PE partner and the agency's plans for the future.

While service providers such as hotels and restaurants were severely debilitated by the pandemic shutdown, others thrived. One such example is Reimagine Care, a Nashville-based in-home cancer care enabler. It's taken cancer care from the clinic to patients' living rooms. Aaron Gerber, co-founder and former CEO of Reimagine Care, says the scope of what can be done for patients has greatly changed with tremendous advancements over the last two and half decades. What had not changed was how that care was delivered. Aaron talks about raising capital and providing oncology healthcare to patients in their own homes.

After years of investing in early-stage companies in the SaaS, robotics, internet of things, health & fin tech spaces, Ven Raju has taken his talents from New York to Pittsburgh where he now heads Innovation Works as its president and CEO, while also holding the position of managing director of Riverfront Ventures. The two organizations have a symbiotic relationship — Innovation Works invests at the earliest stages of a venture while Riverfront provides follow-on capital to those companies that gain traction. Ven compares and contrasts his investment experiences between the two cities, and offers the perspective he's hearing from investors he's talking to as he works to grow Southwest Pennsylvania's startup stature in the market.

Stephen Glicken is working to disrupt ticket sales as we know it with his company, Project Admission. It's a unique model that managed to survive the collapse of live events during COVID and continue to draw investor interest, gain market traction and land significant partnerships. Stephen talks about the business, its growth, fundraising, investors and what he hopes to be saying in the next five years about the company he launched.

Wellist is a consumer navigation company that started by helping to connect patients to services largely outside their care plan — connecting with an acupuncturist, a place to get a wig or someone to clean the house. The company has since opened up its offerings to employees, and in the process has been able to leverage the data it collects to help employers provide better support to their employees and reduce costs. Founder and CEO Ashley Reid talks about growing into the company's now national presence, what outside board seats have taught her about running her own business and the evolution of the company's fundraising.

Shaun Stimpson left a nearly 20-year career in wealth management to launch North Iron Holdings. The purpose of North Iron was to be a vehicle to acquire an industrial distribution company. After an 18-month search, he bought Mitten Fluidpower Corp., which he now runs as CEO. Shaun talks about the move, the acquisition, life as an operator, building a board and his plans for growth.

Barry Sandweiss has co-founded 7 startups, including Lenders One, a company that became the largest mortgage-banking cooperative in the U.S., which he eventually sold. Now he's with Cultivation Capital, a VC firm in St. Louis, sitting on the other side of the investment table. Barry talks about his experience as an entrepreneur, how it's informed his approach to investing, the urge to use his experience to help others and how his entrepreneurial spirit led him to co-found yet another business in 2015 — FinLocker.

John Cerasuolo leads incredibly acquisitive companies. At ADS Security, he led the business through 45 acquisitions in a direct-to-owner model that relied on relationships and an internal team to buy-up companies. Now, with Leap Partners, he's hoping to do the same in the plumbing and HVAC sectors. Already the company he's launched is off to a fast start with 5 acquisitions already complete and a pipeline that could help him realize 20 more this year. John talks about starting the business and how the industry switch and time have affected his process. 

Massachusetts-based technology advisory firms ROI Communications, Blue Front Technology Group and allConnex joined forces in late 2022 to form Amplix. CEO Joe DeStefano says the three long-time, mutually respectful competitors had a familiarity with each other that made the merger a smooth process. When it took less than two hours to put together a proforma balance sheet, they knew they had a great organization. 

In 1985, Sanjiv Singh worked on the first autonomous ground vehicles to operate outdoors. By 2010, he led a team that demonstrated the first autonomous full-scale helicopter flight. Now he's with Near Earth Autonomy, pushing the envelope in autonomy for aerial vehicles both manned and unmanned. He talks about the evolution of the technology, the company's fundraising and the obstacles that must be conquered in order to reach broader commercial adoption of autonomous flight technology.

Harold Green launched Chamberlain Contractors, an asphalt paving company, in 1975 and sold it to Pavement Partners, a portfolio company of Shoreline Equity Partners, in January 2022. While he always had the end in mind, he brought on a partner who didn't share the same goals. Green talks about selling the business, how he resolved the issue with his partner, and his more recent venture that he's hoping to more aggressively grow as he transitions out of Chamberlain.  

Jai Shekhawat is the founder and former CEO of Fieldglass, a cloud-based vendor management software platform that grew to encompass users in 150 countries and more than $60 billion in annual spend, making it the largest such firm in the world. He sold a majority stake in the company to Madison Dearborn Partners, which helped expand the business before selling it to SAP for $1 billion in 2014. Jai talks about the experience from soup to nuts — fundraising, growth, selling and life after.

In 2022, Labcorp paid a reported $450 million to acquire Personal Genome Diagnostics, known as PGDx, a genomic testing company. Megan Bailey, who was CEO of PGDx, stops by the pod to offer a peek inside the deal — what it was like building the deal team, getting buy-in, how they chose Labcorp and why they pursued a sale after successfully raising a $103 million Series C earlier that same year.