Raising capital like a professional isn’t about pitching deals—it’s about building trust, systems, and long-term investor relationships. In this episode, we sit down with Dean DeLisle, a seasoned capital markets executive who has spent decades helping investment sponsors and firms create predictable, scalable capital-raising strategies that work in any market cycle.
Dean breaks down what separates amateur capital raisers from true pros, including how to educate investors instead of selling to them, design repeatable capital pipelines, and position offerings for long-term credibility and growth. Whether you’re a real estate syndicator, fund manager, or entrepreneur, this conversation delivers practical insights to help you raise capital with confidence, consistency, and integrity.
Episode Highlights Here:
Brett
Before we jump into this episode, I want to invite you to join our community to help you become a better steward scale to billions and ultimately give more or all of it away. All I want you to do is to click the subscribe button right now. I love your support. It’s incredible to see your comments, and we’re just getting started. I can’t wait to go on this journey with you. Thank you so much for subscribing. It meansthe world to me. Well, welcome to the build two billion podcast where we got successful entrepreneurs and investors on their journey from millions to billions. We believe the key to scaling and compounding your wealth and life starts every single day with the mindset and practice of stewardship over ownership and applying billionaire biblical principles. Our ultimate goal is to have you scale your wealth, compound your life, so you can make a bigger impact for MVPs most vulnerable people. My name is Brett Swarts. I’m so excited about our next guest. He’ a repeat guest of the build it to a billions podcast, and also the capital gains tax use podcast. He’s now become a longtime friend. It feels like we’ve known each other forever. I think we know about three or four or five years now. First met at the family office club. He’s out of the great state of Illinois in the Chicago area. He has a tremendous background and a lot of different things, but he has a unique background in a few things. And in fact, he began his career at Merrill Lynch in 1982 working in building operations at the Chicago Board of Trade at just 20 years old, and with an extensive background in both corporate and entrepreneurial settings, he has led firms’ capital raising and demand generation efforts. In fact, this is pretty prolific. I call him a Hall of Famer capital raiser. Over the past 35 years, he’s raised over $2.5 billion for clients and played key roles in five IPOs and widely recognized for his expertise in investor education, capital raising and demand generation and so much more. Please welcome to the show, Chief Revenue Officer of regiment securities, Dean DeLisle, how you are doing?
Dean
good? How are you doing?
Brett
phenomenal? Great to see you as always, and I’m looking forward to the wisdom we’re about to glean from you. So, for our listeners who are getting to know you for the first time, give us the 92nd version. They can always go back to the other interview interviews, but just give the 92nd versions, and then we’re going to dive into Adam smashing and what that means for everyone listening today, which you’re going to want to listen you’re an entrepreneur, business owner, investor,
Dean
yeah, great. So, so, yeah, no, it’s, it’s exciting. You know? It’s funny. I started off at Merrill Lynch, and I was in the, like you mentioned, in 82 that was a long time ago in the data space, right? And, and now, all of a sudden, fast forward. I’m a partner in a in an investment bank and part owner and chief revenue officer. And it’s just interesting how my career has just, you know, just exploded towards that direction, right? And, and it almost feels like it’s opportunistic, but not an accident, if that makes sense,
Brett
it does. It’s incredible. It’s incredible. And so, let’s dive right into the topic, which is atom smashing, right? Like, so give us that concept. And, yeah, yeah.
Dean
And more specifically, its atom smashing for capital, right? And what’s interesting is, is you think about, you know, take it, take it back to what atoms aren’t, right? So, atoms, you know, atoms aren’t powerful, just sitting by themselves, right? Just sitting their individual atoms, right? It’s not until they collide that that energy and all kinds of cool stuff come out of that, right? And it’s, we could go on and on, on the science side, but what I, what I wanted to do is this was like one of those epiphanies after I, after I wrote my first book, which we had an interview on. It’s called First, it’s on Amazon, and it’s about, it’s, basically a street guide about how to, you know how to just succeed or get whatever you want. Man, just like when your game, whatever that game is. And now that I’ve raised so much capital using it, and people use it for job creation, sales, everything else, but now that, now that we’ve raised so much capital using the methodology I’m like, I need a dedicated book just toward this. And I was sitting there with some of my buddies, and, you know, the founder at regiment is a powerful network force here in Chicago. I’m a powerful network force here in Chicago. We’ve known each other for 15 years, and it’s one of those things where you just pass people in life and you’re like, hey, we’re going to do something. We got to do something someday, you know, you and I’ll you and I say that sometimes it’s like, hey, we got to do a deal. It’s like, you say that, and then life shows up and you both get sucked into different areas. But if, if you, if you take a moment and really intend that, and now you put those two forces together. Crazy stuff happens. You know what I mean.
Brett
So, if you like this little, short clip of the interview I just did, click over here to watch the full interview, and please don’t forget to subscribe. Thanks so much, everybody. You. Good.
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About Dean DeLisle
Dean DeLisle is a seasoned capital markets executive with more than three decades of experience helping investment firms, fund managers, and sponsors raise capital in a compliant, scalable, and repeatable way. He currently serves as Chief Revenue Officer at Regiment Securities, where he focuses on capital formation, investor education, and building institutional-grade distribution strategies for alternative investments.
Over the course of his career, Dean has helped raise billions of dollars across multiple market cycles by designing investor acquisition systems that prioritize trust, education, and long-term relationships over transactional fundraising. Known for his practical, no-nonsense approach, he works closely with sponsors to move beyond one-off raises and build durable capital pipelines that attract repeat investors and sustainable growth.
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