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The Exit - Presented By Flippa

The Psychology of Selling a Business with Anthony Citrolo, NYBB Group

The Exit - Presented By Flippa

The Exit - Presented By Flippa

Technology

52K Ratings

🗓️ 23 June 2025

⏱️ 31 minutes

🧾️ Download transcript

Summary

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: What really happens when a founder decides it’s time to sell? In this powerful and practical episode, Steve McGarry sits down with Anthony Citrolo, CPA, serial entrepreneur, and managing partner at the NYBB Group, to unpack what really goes into preparing a business for sale. But this isn’t your average M&A conversation. Anthony takes us behind the curtain to reveal the emotional, psychological, and strategic decisions founders face as they approach a life-changing exit. Here’s what you’ll learn: - Why the real exit plan starts the day you launch the business - The #1 mistake founders make when valuing their business - How to prepare your business (and yourself) before a buyer ever knocks - The danger of “key man” risk - and how to build a business that runs without you - What buyers really want: cash flow, scalability, and low concentration - Why 75% of sellers are unhappy post-exit - and how to avoid that fate - How to spot and address hidden risks that could kill your valuation “Most founders don’t realize they’re living vicariously through their business until it’s too late.” Anthony Citrolo With 20+ years in the trenches helping family-owned and founder-led businesses exit, Anthony shares war stories (like Frank, the manufacturer with 98% of revenue tied to 7 customers), practical frameworks, and wisdom earned through decades of hands-on deals. If you're a founder, even if you're years from selling, this episode will change how you think about growth, leadership, and legacy. Listen now to learn how to not just sell your business—but exit on your terms. -- Anthony J. Citrolo is a Managing Partner and Founder of The NYBB Group, LLC, the Exit Strategy Lab and NYBB Commercial Real Estate. Anthony’s clients include privately held companies and family-owned businesses. These are typically companies with revenue of $5M to $100M. Anthony represents HVAC, industrial service, finance, manufacturing, distribution, transportation, healthcare and all service companies. He helps these owners develop a clear and cohesive exit strategy, works to know and improve valuation and actively represents them in a sale or acquisition in a Merger and Acquisition transaction as their advisor and intermediary. Anthony is a CPA and a CEPA (Certified Exit Planning Advisor) and develops comprehensive strategies for owners and families. He also has completed the CEPA course and is a Certified Exit Planning Advisor. In addition, Anthony is a Certified Merger & Acquisition Advisor AND Certified Exit Map Coach. Anthony on LinkedIn: https://www.linkedin.com/in/anthonycitrolo/ Website: https://thenybbgroup.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

Transcript

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0:00.0

Before we get into the exit today, I want to talk about the certified M&A advisors that are on

0:05.7

Flippa. If you are an operator right now running a business and you're thinking about exiting,

0:10.8

you are going to want to get a free online business valuation on the exit landing page.

0:16.7

Without a doubt, it is the smartest thing you can do to start a process and get yourself organized.

0:23.0

So you're going to go to the URL, flippa.com, slash exit, to check out more, and let's jump into

0:28.1

the interview.

0:29.2

Below and welcome to the exit presented by Flipup, the number one platform to buy and sell online

0:34.2

businesses.

0:35.2

Flipa manages over a billion in deal value annually and combines

0:39.4

expert buy and sell side advisory with its market leading valuation tool, deal room,

0:43.9

off market offering, market insights, an AI-based deal-by-deal matching engine. Now for the exit.

0:50.9

The exit is a 30-minute podcast featuring awesome entrepreneurs who have been there and they

0:54.8

have done it. The exit talks to operators who have bought and sold businesses of all different sizes.

1:00.3

You learn how they did it, why they did it, and get exposure to the world of exits. It's a world

1:05.1

occupied by a small few, but accessible to many. On this episode of the exit, I sit down with

1:10.4

Anthony Citrolo.

1:11.9

This is a fantastic conversation about a lot of experience in brokering deals.

1:17.8

Not only do we talk about mistakes that people make around high expectations for the business that they're trying to sell,

1:25.0

but we also talk about some of the just really important things that you can do to try value

1:30.9

and valuation of a business.

1:33.4

Things like adding recurring revenue, things like removing key man risk, things like really

1:39.2

defining your runway as a person.

...

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