The operator tax, the magic five, and handing you the keys

In this episode

Dillon England had me on the Board of Advisors Podcast, and we got into the stuff I talk about with business owners every week: where the bottlenecks are, why you keep hiring to cover work a system should be doing, and what it looks like when you finally have one dashboard that tells you where every job stands.

It's a sixteen minute conversation, so nothing gets stretched. We walk through a real example from one of my own companies, the client we signed the same day we recorded, and the way I actually run this: I build it, I train your team, and then I hand you the keys. There's no forever retainer.

• The operator tax. One person in one of my companies was checking two and a half million lines a year by hand, working sixty and seventy hour weeks. We built a system around that work and pulled back $200,000 a year in payroll, which at a ten times multiple is $2 million in enterprise value.
• 14 admin seats down to 4. One construction client has 50 employees, and 14 of them do nothing but answer phones, enter job orders, and chase invoices across three spreadsheets. Over about six months that team goes to four, and roughly $500K in payroll comes back.
• The magic five. There are probably 50 things that would help any given business. We're not trying to boil the ocean, we find the five that actually move the needle and build those first.
• You own the system. I'm not an agency with a forever retainer. I build it, I train your team, I hand you the keys, and if you want more later, we talk again.

Jump to a moment

• 00:00Dillon's intro
• 00:41What Caddy is: a fractional AI Chief Executive
• 01:20The operator tax, with a $2 million example
• 02:43Cutting a 14 person admin team down to 4
• 04:20The magic five
• 06:24No forever retainer: you own the system
• 08:53The three ways AI pays you back
• 10:04Who's a good fit
• 12:57Why discovery comes first
• 15:08Where to start

Who we are

Meet Caddy is an AI deployment company in Dallas, Texas. The flagship service, ACE, puts a fractional AI Chief Executive inside operations-heavy mid-market businesses for 90 days: discover the highest-value AI opportunities, build the automations, train the team, and hand over the keys.

Everything is deployed at the admin level of your own enterprise AI plan, so you own the system and the data, and you can run it yourself after we leave.

Dillon England is the host of the Board of Advisors Podcast. Thanks for having me on, Dillon.