Every founder eventually faces it: Raise capital, recapitalize, or sell?

Matt Plooster, CEO & Co-Founder of Bridgepoint Investment Banking, joins This Is M&A to break down how founders should think about control, liquidity and timing.

With over $41B in completed transactions and experience at Morgan Stanley and Deutsche Bank, Matt shares how to:

• Raise growth capital without losing control
• Structure recapitalizations the right way
• Know when it is truly time to sell
• Run the private equity playbook without private equity

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Bridgepoint Investment Banking advises middle market companies on capital raising and M&A across healthcare, industrials, consumer, transportation, and technology sectors.

Learn more about Matt and Bridgepoint: Website: https://bridgepointib.com LinkedIn: https://linkedin.com/in/matt-plooster-6b91741/ Email: mplooster@bridgepointib.com

Connect with your host, Steven Monterroso: LinkedIn: https://linkedin.com/in/determined2succeed/

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🎧 Listen now on Apple Podcasts, iHeartRadio and all streaming platforms.

#thisismapodcast #mna #founders #capitalraising #privateequity

Founder-owned exits are rarely clean breaks. In this episode, Nick Cipiti of CriticalPoint reveals the psychology behind partial exits and how buyers can structure deals where the founder wants to stay involved.

Nick is a Managing Director at CriticalPoint with over a decade of experience in middle-market M&A. He specializes in founder-led transactions, carve-outs, and private equity deals where structure and alignment matter as much as valuation.

With personal stories and tactical insight, Nick breaks down: • Why seller motivation isn’t always what it seems • How sponsors behave under dry powder pressure • The structures that align incentives without eroding trust

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Learn more about Nick: Website: criticalpoint.com LinkedIn: linkedin.com/in/nick-cipiti-7b099b9/ Email: ncipiti@criticalpoint.com

Connect with your host, Steven Monterroso: LinkedIn: linkedin.com/in/determined2succeed/

Follow This Is M&A Podcast on LinkedIn: linkedin.com/company/this-is-m-a/

🎧 Listen now on Apple Podcasts, iHeartRadio and Spotify.

#thisismapodcast #mna #founders #privateequity #liquidityevent

Cross-border deals are tough and only a few teams get them right.

Feng Han has executed 100+ transactions in over 13 countries across healthcare, life sciences, and MedTech. In this episode, he reveals the red flags sellers miss, why strategic fit matters more than you think, and how international acquirers are behaving in 2026.

With decades of experience at Henry Schein, Fosun, and Pagoda Capital, Feng now leads Laurel Hollow Capital as Managing Partner.

Founders and dealmakers will walk away with practical tools for avoiding value erosion in international M&A.

📌 Learn more about Feng: Website: laurelhollowcapital.com LinkedIn: linkedin.com/in/feng-han-55b1901 Email: feng.han@laurelhollowcapital.com

🎙 Connect with your host, Steven Monterroso: LinkedIn: linkedin.com/in/determined2succeed/ 📢 Follow This Is M&A Podcast: LinkedIn: linkedin.com/company/this-is-m-a/

Selling your company is not as straightforward as it seems.

In this episode of This Is M&A, Hitesh Nathani, Managing Director at CriticalPoint, reveals the myths that quietly destroy value, and what every founder, operator, and acquirer needs to understand before and after the LOI.

With 19+ years of experience across valuation, private capital, and operating strategy, Hitesh exposes what really happens when private equity gets involved and why most companies fail to realize the value they expect. Founders, operators, and investors will walk away with a clearer view of what it takes to sell well, avoid post-close chaos, and command attention from serious buyers.

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Connect with Hitesh Nathani: Website: criticalpoint.com Email: hnathani@criticalpoint.com LinkedIn: linkedin.com/in/hiteshnathani/

Connect with your host, Steven Monterroso: LinkedIn: linkedin.com/in/determined2succeed/ Follow This Is M&A Podcast on LinkedIn: linkedin.com/company/this-is-m-a/

Timestamps: 00:00 Intro 01:45 Myth 1: “I’ll talk to bankers when I’m ready to retire” 07:02 Myth 2: “Selling my business is straightforward” 13:33 Myth 3: “I don’t need a banker—PE firms are calling me” 23:24 Hidden risks of engaging buyers directly 27:01 Myth 4: “The highest price is always the best deal” 34:44 Seller priorities beyond price (legacy, culture, outcomes) 35:00 Myth 5: “I don’t need a QOE report” 44:00 Hitesh’s Why: Why I left EY for founder-focused work 46:00 Conclusion And Contact Information

Can you scale from zero to $1.2B in under 2 years? Alan Gessel has... five times! In this episode, the CEO of Graystone Corporate breaks down how he built operations, raised capital, and managed risk while scaling at extreme speed.

Alan Gessel is a serial founder, investor, and the current CEO of Graystone Corporate. His resume spans C-suite roles at global firms like Aramark and Sodexo, and his leadership has taken teams from five to 4,500 employees. With over 30 years across buy-side, sell-side, and capital raises, Alan blends operator instinct with strategic depth.

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Learn more about Alan Gessel: Email: alan@graystonecorporate.com LinkedIn: https://linkedin.com/in/alangessel/ Website: https://www.graystonecorporate.com/ LinkedIn: https://linkedin.com/company/graystonecorporate/

Connect with your host, Steven Monterroso: LinkedIn: https://linkedin.com/in/determined2succeed/ Follow This Is M&A on LinkedIn: https://www.linkedin.com/company/this-is-m-a/

Timestamps: 00:00 Intro 03:31 The First Move You Must Make To Grow Fast 05:34 Why Top Performers Are 400% More Productive 10:31 The Critical Difference Between Growth And Scaling 14:45 The "Beware Of Squirrels" Rule For Founders 24:09 Systems You Need Before You Hit The Gas 32:08 Bootstrapping Vs. Raising Capital: How To Choose 45:01 Conclusion And Contact Information

There is a seismic shift in M&A, and most founders are not ready for it. AI is not just transforming products, it is rewriting valuation models, exit timing and competitive strategy.

In this episode, Bob Cronin, Managing Director at Telegraph Hill Advisors, breaks down how AI is reshaping SaaS and software deals, why AI native companies are earning extreme multiples, and what CEOs need to do before the window closes.

Connect with Bob Cronin: Website: telegraphhilladvisors.com Email: bob@telehilladvisors.com LinkedIn: linkedin.com/in/robertncronin/

Connect with your host Steven Monterroso Follow Steven Monterroso: linkedin.com/in/determined2succeed/ Follow This is M&A Podcast: sharevault.com/this-is-ma

00:00 Intro 03:41 How AI Is Disrupting Traditional SaaS Valuations 08:13 Why AI Companies Are Getting 25-150x ARR Multiples 17:25 When Should Founders Exit In This Accelerating Market? 31:00 Why Small AI-First Companies Are Outpacing Giants 40:32 The 12-15 Month Warning: Adapt Or Sell Now

What makes a company attractive to buyers?

It is not revenue alone.

In this episode of This Is M&A, Jordi Pujol, CFA, Managing Director at Objective, Investment Banking & Valuation, explains the financial and operational fundamentals that influence valuation, deal interest, and buyer confidence.

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Connect with Jordi: Website: objectiveibv.com Email: Jordi.Pujol@objectiveibv.com LinkedIn: linkedin.com/in/jpujol1/

Follow your host, Steven Monterroso: linkedin.com/in/determined2succeed/ Follow This is M&A Podcast on LinkedIn linkedin.com/company/this-is-m-a/

Taxes may not kill your deal outright, but they can quietly destroy its value. Christine “Chrissy” Green, Member and Tax Attorney at Steptoe & Johnson PLLC, reveals how middle-market dealmakers can use tax strategy as a competitive edge.

Chrissy works across buy-side and sell-side M&A in the middle market. She covers federal, state and international tax. She also led firm efforts on the Corporate Transparency Act.

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Learn more about Christine Green: Website: steptoe-johnson.com Email: Christine.Green@steptoe-johnson.com LinkedIn: linkedin.com/in/christine-green-37b9b3138

Connect with your host, Steven Monterroso: LinkedIn: linkedin.com/in/determined2succeed/ Follow This Is M&A Podcast on LinkedIn: linkedin.com/company/this-is-m-a/