After two years of searching part-time while working full-time, I’m starting to wonder whether I’m missing something or whether acquiring a quality small business in the Chicagoland area is simply more difficult than the success stories make it appear. A little background on my search: * Reviewed more than 150 CIMs * Submitted multiple IOIs and LOIs * Evaluated both on-market and off-market opportunities * Built relationships with brokers, lenders, and attorneys * Met directly with sellers * Have equity and financing relationships in place for the right opportunity My search has become a balancing act between three priorities: Geography: My family is in the Chicagoland area, so relocating is not a realistic option. I’m focused on businesses I can operate in person within the Chicago metropolitan area. Financeability: I’m looking for a business that can support acquisition financing, not simply one with an attractive stated SDE based on substantial add-backs. I’ve encountered several opportunities where the seller claims a certain level of SDE, but the tax returns show minimal income, break-even results, or losses over multiple years. Transition risk: I’m open to learning a new industry, but I believe an existing team and meaningful seller support are important to a successful transition. Buying a business in an unfamiliar industry when most of the customer, technical, and operational knowledge resides with an owner who plans to leave after 14 or 30 days seems like significant risk. My criteria have evolved throughout the search. I originally focused on businesses generating more than $500,000 of SDE, but I’ve become more flexible as I’ve seen how competitive that segment of the market can be. Along the way, I’ve also considered buying a franchise or launching a bookkeeping or accounting firm from scratch. I keep returning to acquisition because many established businesses took 20 or 30 years to reach their current scale. It’s difficult to justify spending the next decade or two rebuilding that foundation when I could instead acquire a company already generating meaningful revenue and focus my energy on improving and growing what the seller has created. I would greatly appreciate the opportunity to connect with or be introduced to buyers who have recently acquired a business in the Chicagoland area. My goal is to expand my network, learn from those who have successfully navigated this market, and better understand what it takes to get a deal across the finish line.