After a Year of Ownership – Fit & Next Steps

March 17, 2025

by a searcher from University of Denver in Denver, CO, USA

For those who acquired a business and realized after a year that it wasn’t the right fit, how did you navigate the situation?

If you found yourself feeling stuck, drained, or questioning whether to push forward or pivot, what steps did you take? Did you try to reshape the business, bring in leadership, or explore an exit?

I’d love to hear from others who have been in this position and how you approached it.

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Reply by a searcher
from Harvard University in Palo Alto, CA, USA

Thanks for the tag ^redacted‌. Based on my own experience and the experience of other searchers who acquired companies, the first year will be your hardest due to the steep learning curve, uncovering unavoidable skeletons in the business and adjusting to be a full time CEO of a small business. On top of that, if your deal involved the seller keeping all the AP at close, you will have the additional stress of making your working capital last until your business turns cash flow positive. I would suggest that if you see a pathway to being cash flow positive within the next 3-6 months or if your company is already cash flow positive, start making changes to the business now to reshape it to be more inline with what you originally envisioned. Sometimes making small changes that produce positive results and putting your own stamp on the business will make you feel better about your situation. You can start in an area of the business that you have expertise in already (marketing, sales etc). For example in my first year, I compiled a set of client success stories and the clients' approval to use them as sales collateral. Feel free to DM me if you'd like to discuss further and happy to bounce off ideas. Good luck

Reply by a professional
from University of Virginia in Holmes, NY 12531, USA

Thanks ^redacted‌. First, I think ^redacted‌ has a tremendous post above that asks the right and necessary questions to get a handle on what precisely is going on.. I’d note - it’s not especially unusual a year in - esp, w first time buyers - to have many or all of those feelings. And having them doesn’t necessarily mean it’s the wrong business for you. Was it a turnaround situation from the outset? How, with precision, is the reality diverging from expectations? Are the issues emanating from not-as-strong-as-expected financial performance? Free cash flow issues? Or is it more operational? While to be clear, I am NOT recommending that you look to exit - I don’t know nearly enough about the situation - I always advise clients - and work in partnership with them - to operate the business so that it’s *always* sellable and/or prepared for a capital raise. That’s just best practices IMHO. I’d be glad to chat with you and see if I can be helpful at all. Please feel free to shoot a note to redacted Matt

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