Jon Pole On What Makes Someone Want To Buy An “Unsexy” Business
- Kyle Winder
- Apr 28
- 3 min read
Acquirers care more about culture and cash flow than hype—Jon Pole reveals what really drives value in legacy businesses.
About This Episode
What makes someone want to buy an “unsexy” business?
Jon Pole has acquired 19 traditional radio stations. On paper, it’s an industry many assume is in decline. But for an experienced buyer like Pole, these deals are less about media trends and more about community, cash flow, and culture.
In this edition of Built to Sell Radio, part of our Inside the Mind of an Acquirer series, you discover how to:
Understand what professional buyers look for in traditional businesses
Position your company for someone who values consistency over hype
Justify a five-to-seven-times multiple in a slow-growth market
Replace emotional equity with operational systems
Keep your team intact post-sale—without triggering mass exits
Avoid being undervalued just because your industry isn’t trendy
Simplify your exit for a smoother, cleaner handoff
If you run a main street company—or a traditional business in an industry that’s lost its shine—this episode shows how an acquirer sees your value, even when others don’t.
About Our Guest
Jon Pole
Jon Pole is the President and Co-Founder of My Broadcasting Corporation (MBC), one of Ontario’s leading independent radio broadcasters.
With a deep-rooted passion for local media, Jon launched MBC in 2004 alongside his business partner, Andrew Dickson, with a vision to bring community-focused radio to underserved markets across Ontario.
Under Jon’s leadership, MBC has grown to operate over 20 radio stations, delivering hyper-local news, entertainment, and sports coverage to small and mid-sized towns across the province.
A strong advocate for independent media, Jon has played a vital role in preserving the voice of local communities through accessible and relevant broadcasting.
Definition
Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.
Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.
Letter of Intent (LOI): This document outlines the basic terms and conditions of a deal before a formal agreement is drawn up. It serves as a mutual commitment between the buyer and the seller to move forward with the transaction on the agreed-upon terms.
Quality of earnings (or “Q of E”): When an acquirer has secured an exclusive position to purchase your business via an LOI, and the transaction is over $1 million or $2 million in value, the acquirer will often hire an outside CPA firm that specializes in reviewing financial documentation, to provide an analysis of your historical EBITDA compared with the values provided in your CIM. A Q of E report can often be a milestone, enabling an acquirer to consider a major portion of their due diligence completed.
Re-Trading: This occurs when a buyer attempts to renegotiate the purchase price of a deal after initially agreeing to one. It is often seen unfavorably as it occurs after due diligence, seemingly exploiting newly discovered information.
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