October 27, 2025

00:20:47

William Hollis: The AI-Driven Network That's Changing How Real Estate is Funded

William Hollis: The AI-Driven Network That's Changing How Real Estate is Funded
AI Chronicles with Kyle James
William Hollis: The AI-Driven Network That's Changing How Real Estate is Funded

Oct 27 2025 | 00:20:47

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Show Notes

In this episode of the AI Chronicles podcast, host Kyle James interviews William Hollis, founder and CEO of Raise AI, a company that leverages AI to streamline capital raising in real estate. Hollis shares his journey from a self-taught software engineer to a successful entrepreneur, emphasizing the importance of coaching and collaboration in achieving business success. The conversation delves into how Raise AI utilizes AI tools to enhance investor communication, automate processes, and improve overall efficiency in capital raising. Hollis also discusses future initiatives for the company, including an AI-driven investor relations tool that aims to connect investors with opportunities more effectively.

 

Links:

 

Raise AI: theraiseai.com

 

GPT Trainer: Automate anything with AI -> gpt-trainer.com

 

Key Moments:

  • Raise AI uses AI to streamline investor communication.
  • William Hollis's journey began with a fascination for technology and real estate.
  • Joining a mastermind helped Hollis learn effective capital raising strategies.
  • Coaching can significantly enhance personal and professional results.
  • AI tools can increase the number of investor calls booked by 30-50%.
  • Hollis transitioned from offering free services to charging clients for his expertise.
  • AI is used at every step of the capital raising process at Raise AI.
  • The importance of accountability in mastermind groups is crucial for success.
  • Future AI initiatives include an investor relations tool connected to multiple opportunities.
  • The rising tide of AI will benefit all clients of Raise AI.

Chapters

  • (00:00:00) - Introduction to AI in Real Estate Capital Raising
  • (00:02:10) - William Hollis: Journey to Founding Raise AI
  • (00:05:53) - The Importance of Masterminds and Coaching
  • (00:09:28) - Transitioning from Free Work to Paid Services
  • (00:11:01) - Leveraging AI in Capital Raising
  • (00:14:48) - Results and Impact of AI Tools
  • (00:16:38) - Future AI Initiatives at Raise AI
View Full Transcript

Episode Transcript

Kyle James (00:01.112) Hey, welcome to the AI Chronicles podcast. I'm your host, Kyle James. And today we'll be talking about how a real estate capital raising company called Raise AI is using AI inside their own business. And we'll share the exact steps that you can take in order to implement AI for yourself. Now, before I dive into that, listen closely. Are you looking to implement AI inside of your own company or maybe just struggling to get your AI to stop hallucinating? Speak to GPT Trainer. GPT trainer literally builds out and manages your AI for you, eliminating hallucinations for good. Go to gpt-trainer.com. I promise you, it'll be the biggest time saving decision that you've made all year. Trying to set up AI on your own is like trying to build a house from scratch. Sure, you could do it, but the time and frustration is going to take you to get it finished. It may not be worth it. It's a thousand times faster and safer to hire professionals. Scheduled consultation today. Once again, that's gpt-trainer.com. Today I have with me on the show William Hollis, who is the founder and CEO of Raise AI, where he helps real estate capital raisers and fund managers leverage AI-powered automation to streamline investor communication, maximize deal visibility, and secure funding faster. With a unique background as a self-taught software engineer turned real estate investor, Hollis specializes in bridging the gap between cutting edge technology and the real world challenges of raising capital. Very excited for this conversation. Hey Hollis, welcome and how are you doing my friend? Hollis (01:39.928) I'm doing great. That was a fantastic intro. have to say that was, was clean with me. You've got to dial. Kyle James (01:44.582) Did you like that? Hey, you sent it to me. I was just reading it. I don't know if it was a tonality I did, but I'm impressed with it. like, wow, this guy's an all-star. I think I'm pretty sure that we better hit some home runs here on this podcast. Everyone's like, wow, this guy, okay. So yeah, it's great to have you on the show. for everybody listening, tell me a little bit, how did Ray's AI come to be? And give us some background with how you founded the company. Hollis (02:11.768) Yeah, for sure. So from a very young age, two things I was very, very interested in were owning real estate and technology for two totally different reasons. Technology, I've always just been fascinated by understanding how things work. I took apart our first family computer, the Windows 95 giant machine. People probably don't even remember that those existed now, but I took took apart our very first computer, completely disassembled every piece of it. I got my butt beat and put it back together. But that was really the beginning of something incredible for me that led me down this path of kind of teaching myself how to originally build video games, then moved on to websites and web apps and kind of the rest of this history from there. And then kind of simultaneously when I was very young, our landlord just seemed to be so wealthy. Like, I mean, he was the... He had the most money I'd ever seen physically in person at my life. I was probably seven or eight years old and it's the first of the month and he's collecting the rent and he's just stuffing the hundred dollar bills into his wallet. It's so fat, it can't fold. It's like bending the feet of his four tourists. And so that just was always a little bug in my ear, so to speak, of, know, man, I need to figure out how to get into real estate investing. Fast forward many, many years later, I've started Kyle James (03:24.494) Hahaha Hollis (03:39.588) you know, investing in real estate, start trying to understand how to raise capital to buy larger apartment complexes as opposed to, you know, single families or small multifamilies, things like that. And I fell flat on my face pretty hard the first time I tried to raise capital. So I said, I need some help. I went and joined a capital raising mastermind and it was really great. I got a lot of kind of education on how to really market an opportunity, market an investment, how to really communicate with investors well. Um, but I realized that most people were doing this, you know, raising capital, like it was 1942, they had an actual Rolodex. Some people had a physical, this is only eight or nine years ago, maybe seven, seven years ago. People had a physical Rolodex of names they would call when they wanted to raise capital for a deal. And was like the cool guys had like a spreadsheet. Like I was like, man, you guys know there's computers out there. Right. So, um, I kind of started building automated processes for myself, for my own capital ways, my own company. I would just share them with people in the mastermind. Hey, this is how I'm doing it. This is different things that I'm doing. And one day I would do it for free. I built a lot of people systems for free initially, automations. There wasn't too much AI in the very beginning, but as you know, obviously it started to become more popular. started to integrate that. And then one day I'm doing some work for a guy for free and he says, man, it's taking you a long time. And so he goes to me, would you go faster if I paid you? And I thought to myself, I probably would. Yes. So that was actually how the company started was someone who I was doing work for, for free decided they wanted it. They wanted it done faster. So they paid me to do it. And Kyle James (05:21.198) Hmm. Hollis (05:37.592) I said, you know what, I should probably start charging everyone. That was the beginning of the company. Kyle James (05:40.684) Yeah. Yeah. So, I want to, I want to ask you this. So there's two interesting parts here. So first, the mastermind, like, cause you said you fell flat on your face and like, how did you decide the mastermind was the best next step and like, and what in the mastermind was it that like, maybe change some things that your previous, you know, objectives weren't really satisfying, you know, paint that picture for me. Hollis (06:06.488) Yeah. that's really a really good question because what happened was my wife got pregnant and I'm, I'm into working out. I've always been kind of a gym rat and, but I knew that guys have kids and then they get dad bod, right? I just had this thing in my mind that dad bod. If I have a rad, my son gets what was born, I'm going to get the dad bod. So up until that point, I had never hired a trainer before. I made incredible strength gains on my own, just YouTube university and whatever, you know, anybody was doing. And I hired a trainer and I got the best results I'd ever seen in the, the period of four to five months. I mean, just incredible. Like the fat was just coming off the, the two pack was starting to show. and I was like, wow, coaching really does work. I'd been very opposed to coaching in anything. Kyle James (06:58.68) Yeah. Hollis (07:06.306) up until that point, just because I felt like it was a money grab and like, there's so much free knowledge out there that if you're a self-starter, you can kind of figure most things out. But this was the, that was the first experience I had where I got a coach and it, you know, five to 10 X my results. So kind of on the tail end of that experience with my fitness coach, I had the struggle with the capital raising and I said, okay, let me see if the same thing will apply. If I go out and hire a coach, to help me do this, will I actually be able to 10x the results? So the reason it was so helpful, the coaching was so helpful, that's kind of how I got into it, but the reason it was so helpful was a couple of things. One, you don't know what you don't know, right? And so this, was a community of maybe when I joined, maybe 150 members in this mastermind. Yeah, I did. It was a paid mastermind. I went with paid, I'll tell you why I did that in a second, but. Kyle James (07:53.55) Yeah. Did you pay for it or is it like a free? Okay. Hollis (08:03.354) there was so much knowledge just in that room and people were surprisingly forthcoming. Like I thought people would want to gatekeep, you know, knowledge and industry and things like that, but people were surprisingly forthcoming with what they were doing and kind of how they were overcoming different challenges. And there was just a lot of, of help, you know, I realized I didn't have to do all of the pieces of the business myself. So leading up to that point, whenever I did a real estate deal, I Did the acquisition, I managed the contractors, I found the realtors, I basic, I got the loans, I did everything, right? And this was the first time I'd seen like, wow, I can just partner with someone on this deal and I don't have to do all these things that I hate to do. I can just kind of stick to the, know, stick to what my strengths are. And I learned that within the framework of the mastermind, but then also there was a level of accountability there, right? If you go into a room. You're on a zoom call with, you know, 20 people and everybody says, Hey, what you're working on? And you're like, Oh, I'm putting in five offers this week. Well, next week they're going to be like, what happened with the offers? Right. Um, um, that accountability factor was something that I saw benefit from with the fitness coaching and it definitely translated over into the, um, mastermind as well. Kyle James (09:04.364) Yeah, right, right. Kyle James (09:16.524) Yeah. So getting, so it's like kind of the, the, the mindset chain. Well, it really changed when you had the trainer and the trainer into them, into the mastermind. then obviously collaborating and being, and then from there, you said something like earlier, you and then that client that you're working with, you're doing it for free. he says, Hey, if I paid you faster, or if I paid you, would you move faster? And then was that the moment when it just like, it just clicked for you or like, take me back to that time and walk me through what was happening. Hollis (09:46.326) Yeah, I mean, the fact that there was a business here clicked for me because up until that point, I mean, the technology stuff I love and it comes really easily to me. Real estate private equity is an older space. mean, even now, our average client is definitely over 40, maybe in their 50s. And so, you know, they don't have the most facility with technology oftentimes. But here comes me, the young hotshot. I'm, you know, 30 at the time or something like that. And it was just easy. So I would just do it. I was really just focused on building my real estate private equity company. And I had no intention on creating kind of an AI based agency services company. But when the guy said he would pay me, I said, wow, okay, let me see who else will pay me. Like if he's willing to pay me, let me just see if everyone else will pay me too. Kyle James (10:41.322) Hahaha Hollis (10:44.726) And lo and behold, I kind of had five clients out of the gate just from the people who I'd been helping. said, hey, listen, this starting to take a lot of my time. I'm going to have to charge. And most people said, yeah, OK, that makes sense. And yeah, the business kind of started from there. Kyle James (11:03.63) Why? And like from there, it's like, once you get the one client and then it's like the two or the three to five, and then you're like, okay, now my time is becoming more valuable here. Either I charge more or I find a way to go, to make it go faster. So now let's talk about the faster part because you're using AI, right? Like what exactly are you using it within, within raise AI and like, why did you, why did you build that out in the first place? Hollis (11:28.888) Yeah, so taking a step back, my only professional job I've ever had, like a desk job, was working for what was at the time the number one enterprise level AI company in the world. So I've gotten the chance to build AI solutions for Disney. I've done work for Nike, JP Morgan Chase, Verizon Wireless, a whole bunch of companies. And so coming into the capital raising space, even as I was building out some of the simpler kind of automations, just simple automation, email, drip sequence kind of things, even as I was building those things out, I was always looking for ways to make it smarter, make my work faster, but also the end for the client on the other side, right? Make the product that they receive perform better. And so really the initial goal was to build a powerful conversational AI, right? So what we use right now at Chia GPT, that's kind of generative AI. It's kind of meant for you to give something back. You put an input, it says something back to you. Conversational AI is a little bit of an older concept, even that comes from automated customer service voice tool, IVRs, right? Kyle James (12:47.329) Right. Hollis (12:51.076) But really my initial goal was if I can build that, something like that, text-based for capital raisers to use with investors, opens up a whole new world because the biggest problem that capital raisers have or people trying to raise capital have is as you do all of this work to get leads, investor leads in the door, how are you keeping up with them? How are you communicating with them at a good, reasonable cadence? making sure you don't forget anybody. And then the other side of that, like, are you doing that from your personal phone? So your phone is just blowing up 24 seven, you're at dinner with your wife and you're dinging, dinging, dinging, right? With these, these, these text messages and things like that. So that was the original thing I was, I was looking to solve. So that was kind of the first problem that we tackled. And around that time, you know, Chad GPT started to blow up and a lot of different other AI tools. Kyle James (13:26.99) you Hollis (13:45.85) to solve a lot of other problems begin to come on the market as well. So another thing that we do for investors is, or for capital raisers, operators, help them to create all of their marketing, right, for whatever deal they're trying to promote for their company, whatever things they might have. So we have some AI tools that they can just go in and kind of talk to that will help them create entire kind of marketing campaigns that they can use, whether that's... through paid media or just simple organic traffic, videos, different things like that that they want to promote. And now we're really taking it a level deeper with bringing things into the back office, specifically for real estate enterprises. So you raised your capital for your deal, awesome. Well, what about finding more deals to buy? What about... underwriting those deals? What about finding lenders for your deals? What about, you if you bought an apartment building and you said, okay, this is an ugly apartment building, we're going to buy it, fix it up, and now we need to rent it out. Well, how can we use AI to do that too, right? So kind of at every step of the process with commercial real estate, solving all of the problems that our clients run into and leveraging AI at every step. Kyle James (15:05.666) Yeah, for sure. And so talking a little bit about since you've been building this thing out and like obviously expanding to different areas on the backend as it, as you dive deeper, like what types of results would you say you've seen so far either, either, you know, internally on your perspective or even like externally with some of your clients that have been using the AI tools. Hollis (15:27.554) Yeah, for sure. mean, so one thing we track is call schedule rate, right? So basically, you run a Facebook ad and somebody clicks the ad and they say, you know, they say, yeah, I'm interested in this thing, blah, blah, blah. How many of those people who said they were interested, those qualified leads actually schedule calls, right? So we just rolled out V3 of our AI two-ish months ago. And just from that, we saw between a 30 to 50 % increase in the number of calls booked, investor calls booked by using AI tools. So, and the reason that's so important, I mean, 30 to 50 % is a good, is a good jump, but the reason that's so important is because every one of those investors represents potentially hundreds of thousands of dollars. Right. So one investor can invest 200,000. Kyle James (16:10.168) That's big. That's a lot. That's a lot. Yeah. Hollis (16:25.008) 500,000, even 50 or $70,000 into a project. And for the operator, me, I'm buying a building. That is huge, right? Each one of those people who I can get on a phone call with to then go through and close, that's huge. So that's just been one simple result that we've been able to produce with these AI tools. Kyle James (16:44.922) Yeah, that's so cool. That's a huge amount. Like when you think about like the capacity of like what one deal could go for, like having a 30, even just a 20 % increase is I think worth investing, but going 30 up to 50, that makes a huge difference in like the results you're getting as far as like people booking calls or having that first discovery. And tell me a little bit here. So you mentioned a little bit like how you just released V3. you're doing more in the back end and talked about the underwriting, but like what are some of those upcoming AI initiatives for Raise AI and where do you see it playing maybe the biggest role in your operations next, Hollis? Hollis (17:23.056) So I mean, internally in our operations, we use AI for just about everything. I mean, at every turn where we can plug it in, we use it. So if there any real techies out there, one AI that we're working on. And the reason I'm building it is because I haven't found a good one out there. If someone has one, please just send it to me so I don't have to make it. But so for scoping out our tech projects, Kyle James (17:47.586) Hahaha Hollis (17:53.328) Anyone who's ever done any software development knows scoping is by far the most difficult part of any project because you're really trying to figure out what are we building, what's it going to take, who are all the people that need to be involved, what are all the tools that need to be involved. So we're working on an AI solution for that. That's just internal because that's something that kind of delays our projects quite a bit sometimes is having the time to really scope things out to build real development plans. But then externally, the biggest thing that we're working on, I would say it's kind of twofold, but we have version one already of our investor relations AI, which is essentially an AI that can have a conversation with a potential investor, really get an understanding for what their needs are, what their goals are, and then match them up with a specific opportunity if you have one available as the operator. But the next version of that, which is actually probably going to be released toward the end of this quarter or beginning of September, it's going to be that AI is going to be connected to an entire network of investment opportunities. So now when an investor comes through, we'll be able to offer them specific opportunities available that match their criteria directly versus it being tied to any one specific operator and they're just say, I don't. you're interested in multifamily, although I only do single family, so sorry. Now it's going to be connected to an entire network of deals and of investment opportunities. And that AI will be able to literally hold the investor's hand and walk them through the entire process from, yes, I'm interested to, OK, I sent the money and I'm a part of the team now. So that's a huge thing that we're releasing for. our clients because what that will do is that rising tide will lift the ships of all of our clients, right? So everyone who we're working with will have the opportunity to get their deals in front of more and more and more investors on a continuous basis. So that's gonna be a pretty big, pretty awesome thing we're excited about to release. Kyle James (20:08.877) Yeah, I love that. I love that. I love the analogy there with the rising tide that definitely, definitely will. Cause if you get, mean, AI even hand holding you, if you're an expert in the space, if it can help you 30, 40, 50, 60%, a hundred percent, I think that's probably make make it worth making that jump. You know what mean? So, and it's Hollis Magg, appreciate your perspective. been a solid conversation. And for those who are listening, thanks for listening in, but like, where can people go to learn a little bit more about you Hollis and then. Maybe a little bit more about Ray's AI that you'd recommend them checking out. Hollis (20:41.208) Yeah, check us out on LinkedIn. William Hollis, can just search for me or REI Hollis will also pop up. I'm pretty active. I try to answer most messages that aren't spammy. hit me up on LinkedIn and I'm happy to have a conversation and talk a little bit more about Raise AI. The website for Raise AI is the raiseai.com. can go check us out there. Check out some of our info. Be on the lookout for our new marketplace product that I just kind of talked about, Capital Advisory AI as well, that'll be coming up in the next couple weeks here. Kyle James (21:20.398) Awesome, love it. Thanks so much, all. great having you on the show today, and looking forward to potentially seeing you on the next one. Awesome. And remember, thanks everybody for listening in. And if you're looking to implement AI into your business today, please don't try and do it yourself. The time is just the AI could cause. It may not be worth it. Schedule a call with GPT Trainer and let them build out and manage your AI for you. Once again, that's gpt-trainer.com. Hollis (21:26.064) Appreciate it, man. Thanks. Kyle James (21:44.622) Signing off for now, have a great rest of your day everyone, and we're looking forward to seeing everyone on the next episode of AI Chronicles.

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