Smart Business Dealmakers: The Middle-Market M&A Podcast-logo

Smart Business Dealmakers: The Middle-Market M&A Podcast

Business & Economics Podcasts

Smart Business Dealmakers interviews the entrepreneurs doing deals, the PE, VC and family office players investing in them, and the M&A advisers making them happen. Topics include raising capital, buying and selling companies and managing a liquidity event.


United States


Smart Business Dealmakers interviews the entrepreneurs doing deals, the PE, VC and family office players investing in them, and the M&A advisers making them happen. Topics include raising capital, buying and selling companies and managing a liquidity event.




Patrick Patterson, CEO of Level Agency

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.


Aaron Gerber, Co-founder and former CEO, Reimagine Care

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.


Ven Raju, President & CEO of Innovation Works

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, Co-founder & CEO of Project Admission

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.


Ashley Reid, Founder & CEO of Wellist

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, Founder of North Iron Holdings

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, General Partner of Cultivation Capital

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, CEO of Leap Partners

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.


Joe DeStefano, CEO of Amplix

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.


Sanjiv Singh, CEO of Near Earth Autonomy

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, Founder of Chamberlain Contractors

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, Founder of Fieldglass

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.


Megan Bailey, former CEO of Personal Genome Diagnostics

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.


Marc Bernstein, Founder & CEO of Balto

Marc Bernstein is scaling fast and having fun at Balto, a SaaS platform designed to provide real-time guidance to contact center agents. That’s even after the founder and CEO added multiple investors to the mix and recently raised $37.5 million in capital. Marc talks about launching the company, how he's maintaining the culture as he's added layers to his management team, and how the typical characterization of investors-as-bosses is all wrong.


Biju Kulathakal, Co-founder & CEO of Halo Investing

Biju Kulathakal is the co-founder and CEO of Halo Investing, the first independent multi-issuer technology platform for Structured Notes, connecting investment advisors and their clients to the world’s largest banks. He talks about launching the company, pitching to investors and growing the business from an idea to more than 200 employees working in five countries.


James Peisker, Co-founder & COO of Porter Road

James Peisker launched Porter Road with what could be considered an ambitious goal: to change the world. What started as a single butcher shop in Nashville selling meat direct from the farm has spread out across multiple states and, through its thriving online business, is now selling across the nation. James shares how the business got started, why banks hesitated to fund it and how the introduction of not just capital but ideas from VC and PE has led to the company's remarkable growth.


Sean Kennedy, Managing Member of TRG

Sean Kennedy launched TRG in 2002 and has since grown it from a three-person team to more than 300. In addition to its impressive organic growth, the company has expanded through acquisitions, bringing on companies from the U.S., Canada and the UK as it works to become an international player in the managed solutions space. Kennedy talks about the company's growth, the differences between its domestic and international acquisitions, as well as the process of integrating teams that come from much different cultures.


Gavin Slader, Head of Investment Banking at JMP Group

What's going on in M&A today? Is it a buyers' or a sellers' market? What are the macro factors having the most impact on dealmaking and who's taking most of the hit? Gavin Slader, head of the investment bank for JMP, a Citizens company, offers his state of M&A — an overview of the conditions dealmakers are facing and predictions for how the 2023 deal year finishes up.


Dennis Barsema, serial tech CEO; trustee of Northern Illinois University

Dennis Barsema has had a storied career leading numerous telecommunications, software and optical networking companies. He's engaged in myriad capital raises, mergers and several acquisitions. As the CEO of Redback Networks, he led the company through one of the most successful IPOs in Wall Street history and completed a multi-billion-dollar acquisition. Dennis talks about his experience with Redback, the issue that almost prevented him from taking the company public, and how his path eventually led him to teaching future entrepreneurs.


Jonathan Dane, founder of Defiant Capital Group

Jonathan Dane, founder of Defiant Capital Group, discusses the launch of his asset management firm in 2020 and how the turbulence of that year helped shape the business. He also shares his perspective on how the investor mindset has changed over the years since, and offers tips on post-business investment life.