EP354 One Week from Closing, Why Jennifer Stewart Walked Away from the Sale of Her Company

This one is for every entrepreneur who has ever sat quietly with the loaded question: is it time? Jennifer Stewart got all the way to one week before closing the sale of the strategic communications and public affairs firm she'd spent 17 years building - and she walked away.

In this candid conversation, Jennifer traces how an unsolicited email from a New York brokerage led to a fast, unintentional trip to market, what the process taught her about the true value of a service-based business, and why saying no unlocked a wave of yeses: a Vancouver office, deeper government work, a restructured team, and a completely reset relationship with her own business. She also opens up about the seasons of entrepreneurship - the 4:30 a.m. couch shifts while raising two young kids, the recovery from micromanagement, getting over being liked, and why she now protects her mornings and treats her energy as expensive.

Host Colleen O'Connell-Campbell's takeaway frames the whole episode: being exit ready and being ready to exit are not the same thing.

Key Takeaways:

Jennifer started her firm at 25 as JS Communications and built it over 17 years into Syntax Strategic, a nationally recognized strategic communications and public affairs firm based in Ottawa. She is also founder of The Honest Talk, co-owner of Ottawa Valley Green Products, and a board director for organizations including Micropic Biosystems and the Ottawa Hospital Foundation.

The sale process began unintentionally. A New York brokerage had scanned the Canadian market for small-to-medium firms with strong retainers and government contracts, and shortlisted her company. She had been naive to the fact that a service-based business could be sold at all - a belief she now laughs at.

Once she agreed to a valuation, things moved fast: within two weeks of going to market she was in discussions with a buyer, had an NDA signed, and had begun due diligence. Several other interested parties surfaced within a week. She reached one week from closing before deciding not to proceed.

The process fundamentally changed how she runs her business. She now monitors her balance sheet, P&L, and adjusted EBITDA through the lens of enterprise value - not just margin. Agency multiples were roughly four to five at the time, and she notes that service-based businesses are becoming more valuable in investors' eyes.

Her biggest lesson: take control back. She had jumped at the first prospective buyer with a mind