Cash Flow Connections - Real Estate Podcast
Jun 19, 2026 · 30 min · 11 segments
In today’s RaiseMasters Radio episode, I sit down with Ellis Hammond to talk about the lessons that only come from surviving market cycles, raising capital through challenging environments, and…
Ellis HammondGuest
Hunter ThompsonHost
So you went from, member to getting started to having a lot of success, raising quite a lot of money, becoming a coach, which is something we take very seriously.

Obviously, Ben Frazier was the previous coach, but you have taken his role as one of the lead capital raisers now at Aspen Fund.

You've been able to maintain a very good reputation through a lot of different markets and a Seeing the inside now, what have you learned going through this solopreneur, scrappy, struggling kind of vibe, which all of us do at the beginning of our careers, to fully buttoned up shop, almost half a billion under management? What are some of the lessons you've learned, man? I know there's a lot, but what do you see making that transition for people that are in your spot now?

I don't know what I want to talk about, but I think this is exactly the benefit that Bob and Jim had.

And the benefit that I did not have when I started my previous company is that I had not lost anything.

That mindset, that experience, and especially in real estate, because these cycles can take 10 to 20 years to really happen again.

And so you may come into it as an early real estate investor and have no idea that real estate can drop in value by what it's done or interest rates can rise.

You just have no context for that, right? And so I think the biggest difference in the things that I've learned now and what I would look back, I'm like, man, I wish I would have taking it a little bit more slowly and really understood debt, for example, and interest rates as another one.

And I think that is the real privilege I get here at Aspen is to be around guys like Bob and Jim and Ben.

But Bob and Jim, primarily because they're older and they've been through several cycles and not with Aspen, Jim was bankrupt, literally bankrupt.

And then to build it all again, What does that do as someone who's really trying to build a legacy business and the decisions you make? It's wildly different than starting a business at 25 years old when you're just ready to rip it, man.

And so it's been so good because I look back and I think about how hard it was, even when things were good, to build our business early on.

So you went from, member to getting started to having a lot of success, raising quite a lot of money, becoming a coach, which is something we take very seriously.

Obviously, Ben Frazier was the previous coach, but you have taken his role as one of the lead capital raisers now at Aspen Fund.

You've been able to maintain a very good reputation through a lot of different markets and a Seeing the inside now, what have you learned going through this solopreneur, scrappy, struggling kind of vibe, which all of us do at the beginning of our careers, to fully buttoned up shop, almost half a billion under management? What are some of the lessons you've learned, man? I know there's a lot, but what do you see making that transition for people that are in your spot now?

I don't know what I want to talk about, but I think this is exactly the benefit that Bob and Jim had.

And the benefit that I did not have when I started my previous company is that I had not lost anything.

That mindset, that experience, and especially in real estate, because these cycles can take 10 to 20 years to really happen again.

And so you may come into it as an early real estate investor and have no idea that real estate can drop in value by what it's done or interest rates can rise.

You just have no context for that, right? And so I think the biggest difference in the things that I've learned now and what I would look back, I'm like, man, I wish I would have taking it a little bit more slowly and really understood debt, for example, and interest rates as another one.

And I think that is the real privilege I get here at Aspen is to be around guys like Bob and Jim and Ben.

But Bob and Jim, primarily because they're older and they've been through several cycles and not with Aspen, Jim was bankrupt, literally bankrupt.

And then to build it all again, What does that do as someone who's really trying to build a legacy business and the decisions you make? It's wildly different than starting a business at 25 years old when you're just ready to rip it, man.

And so it's been so good because I look back and I think about how hard it was, even when things were good, to build our business early on.
The rest of this transcript — segmented and speaker-labeled, so you land on the exact moment something was said
Search every transcript — by keyword, by phrase, or by meaning, across every show Radar indexes
Trends — what is surging across podcasts, measured against its own baseline
Alerts — when a name you follow appears in a newly indexed episode
No account is needed to search Radar.