What an AI matchmaker taught me about who really needs my help
Dennis Edogun, Boardy Boardman, and Francesco Ientile. Boardy's first move as matchmaker: put two people in a room who work on the same problem from opposite sides.
The introduction
This morning I met Dennis Edogun. Boardy set us up.
If you haven't met Boardy, he's an AI who introduces people who should know each other. He joined the start of our call, said why he'd matched us, and stepped back to let us talk.
The match was sharper than I expected.
One problem, two angles
Dennis and I both work with owners of small businesses in Ontario. He works on the risk side. I work on the sales side. Both of us end up sitting across from the same kind of owner. Someone who has built something real, but the business still lives inside their head. If they step away, the business stops.
Dennis helps owner-led businesses identify and reduce owner-dependency risk by documenting critical knowledge, strengthening systems, developing leadership capability, and building operational resilience. Through risk advisory and business continuity planning, he helps owners build businesses that can grow, operate, and eventually transition without relying entirely on them. The result is a stronger, more resilient, and more valuable business.
Why it matters
The Canadian Federation of Independent Business reports that most small business owners in Canada plan to exit their business in the coming decade. Over $2 trillion in assets will change hands. Only 9% have a formal, written succession plan.1
That gap is where Dennis works.
In Dennis's words
"I help owner-led businesses reduce owner-dependency risk. Every business creates more than profit: it creates livelihoods, opportunities, and legacy. My role is to help owners build systems, leadership, and resilience so the business can continue to thrive without depending entirely on them. When a business can operate without its owner, it becomes stronger, more valuable, and far more transferable. Because every business creates more than profit: it creates livelihoods, opportunities, and legacy. My mission is to protect everything your business makes possible."
Where Sandler fits
The Sandler work I do fits the same problem. A sales system that lives in one person's head carries the same risk. When the owner is the top salesperson, no buyer wants the business. The doors just close.
A documented sales process, used every day by more than one person, protects the value of the business the same way documented operations do.
Find out how much of your business depends on you
I run an X-Ray assessment for owners who want a straight answer. It measures how your sales process actually works today, who holds the relationships, and what happens to your revenue if you step away. It takes a short survey from you and your team. You get the findings back in a one hour conversation with me. No cost, and no pitch at the end.
Book Francesco
francesco.ientile@sandler.com
416-841-0038
If you know an owner building something worth protecting, send them this. If you know an owner who can't step away, send them to Dennis.
Boardy, thanks for the intro.
About the author. Francesco Ientile trains and coaches owners of small and medium businesses across the Greater Toronto Area. He owns Sandler in Markham and works with owner-operated firms on one thing: building a sales process the business runs on, rather than one that runs on the owner. Find him at go.sandler.com/beyondgrowth or on LinkedIn.
1. Canadian Federation of Independent Business, "Over $2 trillion in business assets are at stake as majority of small business owners plan to exit their business over the next decade," 10 January 2023. Read the release.