# 3 exits in 10 years, and why buyers smell desperation · Worth Owning · Horizon

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![](/images/guests/jacqueline-dinsmore.jpg)Worth OwningEp. 03Jacqueline Dinsmore

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Worth Owning · Episode 03

# 3 exits in 10 years, and why buyers smell desperation

Hosted by **Krystyn Harrison** · With **Jacqueline Dinsmore**, Managing Partner, CaravelSep 2025 · 40 min

0:0040:00

Watch or listen on[Apple Podcasts](https://podcasts.apple.com/us/podcast/jacqueline-dinsmore-3-exits-in-10-years-from-bay-street/id1830558138)[Spotify](https://open.spotify.com/show/5hOpLGuAecUP1KyJerEMwC)[YouTube](https://www.youtube.com/watch?v=9wUlwqDujR4)

## Sold FlapJack Kids months before COVID would have shut its stores

Overview

Jacqueline Dinsmore left a Bay Street law career at Blakes when her mother was diagnosed with breast cancer. After her mother recovered, the two started a handbag business on maternity leave that reached about 250 stores, then turned it into FlapJack Kids, a reversible kids clothing brand run with her parents and husband. They sold it in 2019, just before COVID shut the brick and mortar stores that made up 95% of its sales. She has had three exits in under a decade.

Jackie explains why the FlapJack Kids sale worked: the buyer owned one of their factories, had watched the business grow, and was buying several brands to share one overhead. The deal came from the relationship, not the spreadsheet. Her professional services exits taught her the other side, where culture, low attrition and strategic fit matter as much as revenue, and a buyer will pass on a firm that does not fit its plan.

Then the parts owners skip. After the sale her mother was sad, and Jackie talks about the success hangover and staying on as the last founder standing. She has watched owners show up to a sale with no minute book, no IP plan and no idea what a data room is. Her advice: relationships matter more than pitch decks, take care of yourself first because buyers smell desperation, and run your business as if due diligence starts tomorrow.

Chapters

What you’ll learn

01Why your best buyer may already know your business

02How buyers read burnout and a messy data room

03What buyers of professional services firms look at beyond revenue

04How to prepare for the emotional hit after a sale

Where does your business stand today?

[Get your Optionality Score →](/optionality-score)

## More on the episode

Episode 03Sep 2025 · 40 min

Note: Krystyn, Matt and their guests may hold interests in companies discussed in this episode. Worth Owning is not financial, legal, tax or investment advice, and is for informational purposes only. Do your own research and speak with your own professionals before making any financial decision.

[Where this shows up in your businessWould your business pass diligence tomorrow?The Exit Partnership gets your books, documents and data room ready before a buyer asks, with a Partner who has been through the deal.See the Exit Partnership →](/exit-partnership)

![Jacqueline Dinsmore](/images/guests/jacqueline-dinsmore.jpg)

Guest

Jacqueline Dinsmore

Managing Partner, Caravel

Jacqueline Dinsmore is a former Bay Street lawyer who co-founded FlapJack Kids with her family and sold it in 2019. She has had three exits in under a decade, including two in professional services, and is managing partner at Caravel.

[caravellaw.com](https://www.caravellaw.com)

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