Buying a business is one thing—but knowing how to actually grow it is where the real challenge (and opportunity) begins. In this episode, Jaryd Krause chats with Matthew Person, a corporate strategist, investor, and M&A expert who’s mastered the art of scaling through acquisition.

With experience across investment banking, corporate development, and private equity, Matthew knows what it takes to turn good businesses into great ones. He’s the mind behind the Square Management System, a framework built to help entrepreneurs align culture, structure, and strategy so growth happens seamlessly—not chaotically.

In this episode, you’ll learn:

✔️ Why understanding customer lifetime value is more important than acquisition cost
✔️ How pricing and packaging decisions influence business scalability
✔️ What makes the Square Management System a powerful tool for growth
✔️ The critical role of cultural fit in M&A integration
✔️ How to manage different revenue types and their impact on valuation
✔️ Why boring businesses often yield the best returns
✔️ The common integration challenges—and how to plan for them
✔️ What successful portfolio builders do differently from the rest

Jaryd and Matthew break down the real drivers of business success, from understanding customer lifetime value and pricing strategy to building systems that make integration smooth and scalable. Whether you’re eyeing your first acquisition or managing a growing portfolio, this episode shows you how to scale smarter, not harder.

🎧 Tune in to learn how to build, buy, and scale businesses the smart way—through systems, strategy, and structure.

Episode Highlights

09:17 – The Square Management System: Matthew’s proven framework for scaling businesses through structure, culture, and alignment.

14:10 – Lessons from investment banking: insights on spotting hidden value and capturing upside in every deal.

18:52 – Smarter deal structures: balancing growth potential with risk mitigation to protect your investment.

21:15 – The magic of recurring revenue: how predictable income streams boost valuation and stability.

23:38 – The art of integration: navigating the human and operational challenges that make or break acquisitions.

29:05 – Culture as the glue: why cultural fit is essential for seamless post-acquisition success.

33:37 – Scaling through systems: how effective management systems create control, consistency, and scalability.

37:38 – Portfolio builders’ mindset: the habits and principles of investors who consistently grow thriving portfolios.

Key Takeaways

➥ Growth by acquisition starts with deep customer and market understanding, not spreadsheets.

➥ Retention drives profitability—a loyal customer base is the real engine of value.

➥ A clear pricing strategy can multiply growth potential without new customers.

➥ Culture eats strategy for breakfast—successful integrations start with people, not processes.

➥ Investment banking experience gives you the lens to structure smarter, safer deals.

➥ Different revenue types (recurring, transactional, hybrid) shape how your business is valued and scaled.

➥ The Square Management System offers a blueprint for scaling operations across multiple brands.

About Matt Person

Matt Person is a seasoned corporate strategist, investor, and M&A expert with over 25 years of experience helping companies build and capture enterprise value. Currently SVP of Corporate Development at Quickbase (a Vista Equity-backed SaaS platform), he also founded Town Square Advisors, where he created the Square Management System: a proprietary framework that drives high performance through alignment, culture, and organizational design built on constrained independence.

Prior, he led global corporate development, deal execution, and growth strategy for enterprise SaaS firms like IDG and Green Street Advisors, as well as worked in investment banking and strategy consulting. Matt combines deep technical and financial expertise with operational leadership and a passion for building winning teams. On this episode of the Buying Online Businesses Podcast, he shares how you can not only buy and scale online businesses, but also structure them and your own mindset to replace your income and craft a life of freedom.

Connect with Matt Person

➥ www.townsquare-advisors.com

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u

➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM

➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

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How to Scale Through Acquisition: Organizational Design & M&A Strategy with Matt Person

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