Cash Flow Connections - Real Estate Podcast
Aug 21, 2026 · 24 min · 10 segments
In today's RaiseMasters Radio episode, I sit down with Jesse DeLillo to unpack the lessons he’s learned from placing roughly $70 million in investor equity and helping hundreds of capital raisers. We…
Jesse DeLilloGuest
Hunter ThompsonHost
Honestly, it's like a lot of the automations, we were doing most of it manually.

The things that we've been able to implement, they work, but it just takes so much time to manually do it.

Setting up automations and using the system and processes to get people into the door and having clear follow-up sequences, it just made everything a lot more streamlined.

We've been able to just raise significantly more more capital at a much more consistent pace rather than rushing at one point blitzing our list and then kind of holding off now we have a really good follow-up process and a nurture sequence but we really took that away and i think that that's one of the biggest one of the biggest things honestly for all capital raisers is that consistency i mean staying in front of your clients because you can't you're not going to raise capital if like you just have a deal and then you try to blitz people and then you have to wait and then you have another deal and then you blitz people again like if you're not really building like true relationships you're not going to have a lot of success we did a lot of in-person things that that translated into some capital raised as well and i like where we're kind of steering the ship here with a lot of our clients now who want to get back into going to live events hosting their own meetups going to meetups doing things like that i guess those tend to translate into quicker relationships and just more capital in the door quicker so

Ballpark, just for the listeners, how much capital have you placed? What are the kinds of deals you've put them into?

So it hasn't been any family office or we've partnered with one family office on one deal at one time.

Yeah, between my team and I, you know, we've been, we deployed it into multifamily, some self-storage deals.

We get to work with some of our own clients, partnering on deals and allocating into opportunities that we see.

We tend to invest our own dollars first, kind of see if the operator's good, and then we may allocate a larger check to them.

But we really enjoy this, really that window, and then seeing how they perform in the next couple of years.

Honestly, it's like a lot of the automations, we were doing most of it manually.

The things that we've been able to implement, they work, but it just takes so much time to manually do it.

Setting up automations and using the system and processes to get people into the door and having clear follow-up sequences, it just made everything a lot more streamlined.

We've been able to just raise significantly more more capital at a much more consistent pace rather than rushing at one point blitzing our list and then kind of holding off now we have a really good follow-up process and a nurture sequence but we really took that away and i think that that's one of the biggest one of the biggest things honestly for all capital raisers is that consistency i mean staying in front of your clients because you can't you're not going to raise capital if like you just have a deal and then you try to blitz people and then you have to wait and then you have another deal and then you blitz people again like if you're not really building like true relationships you're not going to have a lot of success we did a lot of in-person things that that translated into some capital raised as well and i like where we're kind of steering the ship here with a lot of our clients now who want to get back into going to live events hosting their own meetups going to meetups doing things like that i guess those tend to translate into quicker relationships and just more capital in the door quicker so

Ballpark, just for the listeners, how much capital have you placed? What are the kinds of deals you've put them into?

So it hasn't been any family office or we've partnered with one family office on one deal at one time.

Yeah, between my team and I, you know, we've been, we deployed it into multifamily, some self-storage deals.

We get to work with some of our own clients, partnering on deals and allocating into opportunities that we see.

We tend to invest our own dollars first, kind of see if the operator's good, and then we may allocate a larger check to them.

But we really enjoy this, really that window, and then seeing how they perform in the next couple of years.
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