# Horizon LIVE: what makes a profitable business sellable · Worth Owning · Horizon

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![](/images/guests/jacqueline-dinsmore.jpg)Worth OwningEp. 17Jackie Dinsmore and Brent Holliday

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Worth Owning · Episode 17

# Horizon LIVE: what makes a profitable business sellable

Hosted by **Krystyn Harrison** · With **Jackie Dinsmore and Brent Holliday**, Caravel Law and Garibaldi Capital AdvisorsApr 2026 · 56 min

0:0056:00

Watch or listen on[Apple Podcasts](https://podcasts.apple.com/us/podcast/horizon-live-how-to-sell-your-profitable-business-jackie/id1830558138)[Spotify](https://open.spotify.com/show/5hOpLGuAecUP1KyJerEMwC)[YouTube](https://www.youtube.com/watch?v=G_IgImf6sQY)

## Under $5M in revenue, you lose about 65% of buyers

Overview

In the first live session of Inside M&A: Opening the Playbook, Krystyn sits down with Jackie Dinsmore, managing partner of Caravel Law and a founder who has sold three companies, and Brent Holliday, founder and CEO of Garibaldi Capital Advisors, a tech-focused M&A firm since 2013. Jackie sets the frame: a profitable business feeds the current owner, and a sellable business feeds the next one. Brent adds the number: under $5 million in revenue, a tech company loses about 65% of its buyers.

They walk through how to stage a business like a house for sale: minute books, legal documents, clean financials and a data room ready before anyone asks. Brent explains EBITDA normalizations in plain English, including how paying yourself $800,000 for a role worth $200,000 can mean about $3 million of value at 5 times. Jackie adds that the brand has to be stronger than the owner, and that surprises kill deals.

Then the moments owners get wrong. When a buyer calls, take the call, let them talk and never name a number first. A real process takes 6 to 8 months at minimum, and Jackie’s three exits each took a year or more. Keep the circle tight, sell toward something rather than away from burnout, and before you sign, ask to speak with founders the buyer has already bought.

Chapters

What you’ll learn

01How to stage your business so a buyer trusts it

02How normalizing your salary can add millions in value

03What to say, and never say, when a buyer calls

04How long a sale takes, and when not to sell

Where does your business stand today?

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

## More on the episode

Episode 17Apr 2026 · 56 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 businessWant a business that feeds the next owner?The Exit Partnership gets your house in order before a buyer opens the closets.See the Exit Partnership →](/exit-partnership)

![Jackie Dinsmore and Brent Holliday](/images/guests/jacqueline-dinsmore.jpg)

Guest

Jackie Dinsmore and Brent Holliday

Caravel Law and Garibaldi Capital Advisors

Jackie Dinsmore is managing partner of Caravel Law, with about 120 lawyers across Canada, and has sold a consumer products company and two professional services firms. Brent Holliday founded Garibaldi Capital Advisors in 2013 as Canada’s first tech-focused M&A advisory firm, after about 15 years as a venture capitalist.

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