Jul 28, 2026 · 1 hr 4 min · 14 segments
What separates property management companies that grow intentionally from those that simply react? In this episode, Marc Cunningham sits down with Andrew Smallwood, Chief Strategy Officer at Second…
Mark CunninghamHost
Andrew SmallwoodGuest
Has your property management company ever done a strategic planning session? You've probably heard that word before, and some big companies will have offsites.

They'll take their entire team somewhere fun for a few days, and they'll talk about strategy and thinking in the future of their company.

Well, for most of us, that's not something that's just practical or realistic to do.

But today, my friends, for the next hour, you are going to listen in and participate in a strategic planning session with my friend Andrew Smallwood, who is the chief strategy officer with Second Nature.

I'm doing a call with him, and he's going to walk me and my company through through some questions on strategic thinking that I think will apply to you as well.

This is thinking about your business in a very straightforward, strategic way that gives you actionable things to do to improve your business he's going to give some advice on how to think differently strategically based upon the size of your company i'm going to give him my thoughts on that and if you're a real small company the way i believe you should think strategically is completely different than if you're a larger company.

So he'll give me his feedback, tell me whether I'm thinking right or wrong on that.

And then he's going to also share common mistakes that companies make as they're going through strategic planning for their businesses.

We went a little longer than I had anticipated because it was so fun and I found this very beneficial.
Read the full transcript.
Create an account to read the whole episode, search across every transcript, and follow the shows you care about.

Has your property management company ever done a strategic planning session? You've probably heard that word before, and some big companies will have offsites.

They'll take their entire team somewhere fun for a few days, and they'll talk about strategy and thinking in the future of their company.

Well, for most of us, that's not something that's just practical or realistic to do.

But today, my friends, for the next hour, you are going to listen in and participate in a strategic planning session with my friend Andrew Smallwood, who is the chief strategy officer with Second Nature.

I'm doing a call with him, and he's going to walk me and my company through through some questions on strategic thinking that I think will apply to you as well.

This is thinking about your business in a very straightforward, strategic way that gives you actionable things to do to improve your business he's going to give some advice on how to think differently strategically based upon the size of your company i'm going to give him my thoughts on that and if you're a real small company the way i believe you should think strategically is completely different than if you're a larger company.

So he'll give me his feedback, tell me whether I'm thinking right or wrong on that.

And then he's going to also share common mistakes that companies make as they're going through strategic planning for their businesses.

We went a little longer than I had anticipated because it was so fun and I found this very beneficial.