Small business deal uncertainties

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April 11, 2026

by a searcher from Northwestern University - Kellogg School of Management in Chicago, IL, USA

I'm under LOI for a small print media advertising company in my targeted Midwest region. The business has been fairly stable, but with modest declining revenue in recent years and a need to strengthen margins--the biggest growth lever will be through digital development. My background is in tech and digital transformation, so this is where I'd fit in strategically. The business is smaller than I'd like, but checks other important boxes (e.g. target region and service-based). There have been some emerging flags during diligence including: (1) Cash flow realities of this business make it too small for me to go 'all-in' from a personal income perspective, (2) Declining revenue and margins in recent 3 years (~3-5% per year decline) stated as tied to lack of digital capabilities, (3) Strong family ties to current operations, (4) Net take-home of this deal does not meet the owner's full needs for 'early retirement' as he wanted, so he's becoming more nervous. I'm considering either walking from this deal, or making an equity partner offer. As a partner, I could drive digitization of the business and ready it for a stronger exit in 5-8 years, keep the owner vested in the business while providing him needed income, and allow me to remain out of the day-to-day. I generally like the owner, find him trustworthy, honest, and we have complementary skills. Does anyone have experience with partial equity purchase of a small business? Is this generally a bad idea or not worth the effort? What makes an offer like this attractive to a seller?
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Reply by a searcher
from Dartmouth College in Cary, NC, USA
Partial equity purchases work best when the seller has real skin in the game post-close — sounds like yours does. The bigger watch-out is the retirement gap. If he needs more than this deal delivers he'll be a difficult partner no matter how much you like him now. The declining revenue needs to be properly baked into the price — if it is, the digital transformation thesis could absolutely work. What does your valuation look like? DM me if you want to run through the numbers together.
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Reply by a lender
from Eastern Illinois University in 900 E Diehl Rd, Naperville, IL 60563, USA
Happy to do a free deal review from a lenders perspective and provide you some feedback. It does look like there are some real concerns there that you have identified. One thing your going to have to decide on is whether you can make the changes from the outside and are willing to not be full-time in the deal. If we can be of any assistance, you can reach me here or directly at redacted
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