Latest News - Adrienne Green

How One AI Handles 20,000 Buyer Conversations at Once

September 7, 2026September 7, 2026

If you have ever felt like your business runs on leads that go nowhere, you are not alone. In this episode, I sit down with Sheldon Wolf, a founder, investor, and operator with over 35 years of experience across real estate, finance, and technology. Sheldon built Intellitary, an AI-powered platform he calls the “Un-Brokerage,” designed to pre-qualify buyers and sellers before they ever reach an agent. We get into why most lead generation is a waste of money, what it really takes to build a business that survives the next market shift, and what he believes the real estate transaction will look like five years from now. If you are ready to rethink how customers find you, this conversation is worth your time.

For a complete guide on optimizing and scaling your real estate investments, download my Time + Freedom Starter Pack! This essential tool walks you through ten key steps for organizing a profitable property portfolio. Click here to get your copy today!

Hello and welcome. I’m Adrienne Green, and here we talk about how, as a real estate entrepreneur, you can get out of the grind and start getting the freedom that you really got into real estate for in the first place. And to speak to that, today I have with me Sheldon Wolf. Sheldon, thank you for joining me.

Thanks for having me. It should be a lot of fun.

So Sheldon, my understanding is you’ve spent over thirty-five years as a founder, investor, and operator across real estate, finance, and technology, all things I love. So for our listeners who are just meeting you, what does your world look like today?

One Owner, One Contact: The System Behind 300 Managed Properties

September 3, 2026September 3, 2026

Before you dive into the full conversation below, here’s a quick preview: in this episode I sit down with Cameron Tope, who owns more than 30 rental properties himself and manages over 300 more for investors in the greater Houston area, all run remotely from San Diego. Cameron walks through the breaking point that led him to build his own property management company, the systems he uses to turn a property in 10 days instead of 30, why vacancy costs investors far more than a management fee ever will, and how operating as both an owner and an operator shaped every decision along the way. If you want a real look at how systems, KPIs, and delegation work together in a scaling operation, this is worth the watch.

Got it, here’s the full transcript in one continuous piece, start to finish:

I am Adrienne Green. We focus on how real estate entrepreneurs can break free of the grind and create the freedom they wanted at the start, and Cameron has a lot of wisdom to share on the subject. So can we start, Cameron, with giving our listeners a quick snapshot of your world in the sense of real estate. Properties you own, what you’re doing for others, what it looks like for you today.

Today I have just over thirty properties myself personally that I own. And we manage about three hundred for investors in the greater Houston area. And I do this all a hundred percent remotely from San Diego, California.

Amazing. Love that. And my understanding is that there was a breaking point with property management that made you decide to build your own company. Can you talk to us a little bit about the pain point you had and what prompted you and how you made that decision?

From Medical Sales to a 10-Agent Investor Team Across 3 States

August 24, 2026August 24, 2026

Every real estate entrepreneur reaches a point where the business they built can no longer run through sheer effort alone. In this conversation, I talk with Niyi Adewole, who went from a single house hack in Louisville to a 30-unit rental portfolio, a ground-up self storage development, and a 10-agent investor-focused real estate team spanning three states. Niyi walks through the tasks he held onto for far too long, from invoicing to transaction coordination to guest messaging, and exactly what pushed him to finally hand them off. We also dig into how he evaluates new opportunities, how he manages a business across multiple states without ever setting foot on some of the properties, and why he believes consistency beats big bets every time. If you have ever felt like your growth is capped by your own hours in the day, this one will give you a lot to think about.

Hello listeners and welcome back. I’m Adrienne Green and today we’re here with Niyi Adewole. Here we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start, and Niyi is a great example of that. Thanks for being here with me.

Thank you for having me. I’m pumped to be on.

To start off, give us the quick version of your portfolio and business and what they look like today.

My name is Niyi Adewole. I have been investing in real estate for over a decade and built that portfolio well before I got a license. I got licensed in 2021 and have now built out a team. What it looks like today is I have a self-storage unit that’s 225 units that we built from the ground up a few years ago. I used to have 30 long-term rentals, but I traded those in to build that self-storage and buy some other properties. I own eight short-term rentals, five long-term rentals, and I land on flips and then help other investors get started in real estate as well.

The One Task This Fund Manager Still Won’t Delegate

August 21, 2026August 21, 2026

If you have ever felt like your business cannot move without you personally holding every relationship together, this conversation is for you. I sat down with private lender Alexis Morgan, who built a fund from eighteen years old with no corporate background, no playbook handed to them, and no shortage of moments where they thought certain tasks could only be done by them. What changed was not working harder. It was learning how to turn relationships, investor communication, and even the parts of the business that felt too personal to hand off into real systems their team could run. If you are scaling a real estate business and trying to figure out what to build, what to delegate, and what still needs your hand on it, this one will give you a lot to think about.

I’m Adrienne Green and today we are here with my friend Alexis Morgan. Here on this podcast we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start. Alexis is an interesting story because I don’t know that you ever really experienced the grind. What do you think?

I think entrepreneurship in the beginning is the utmost description of the grind. Not in a traditional sense, but I definitely went through a period of startup and ramping up for sure.

That’s very fair. And yet you are unique because you really started as a real estate entrepreneur before you were ever any other business person, I believe.

That’s correct. I got started in real estate at eighteen years old, and I’ve been doing real estate now almost five years. It’s been the only thing I’ve focused on, the only thing I’ve known, not coming from a traditional corporate background.

How Much Automation Is Too Much in Short-Term Rentals?

August 3, 2026August 3, 2026

I sat down with Akshay Bajaj, a former AI engineer who spent over a decade building systems for self-driving cars and aircraft autopilot before turning that same expertise toward his own short-term rental portfolio. Akshay walks through the exact moment he realized property management had the same core problem as the robotics he’d spent his career solving, and how that insight led him to build an AI system that handles guest messages, vendor coordination, and dynamic pricing while knowing exactly when to hand a decision back to a human. We get into why most property management AI is really just glorified auto-replies, how his platform’s “ask before act” approach protects the guest experience, and where he thinks the short-term rental industry is actually headed over the next few years. If you’ve ever felt like self-managing a rental gave you cash flow but took away your time, this conversation gives you a real framework for getting both back.

I’m Adrienne Green, and today we’re here with Akshay Bajaj. Akshay is a great example of someone who broke free of the grind, and he’s made a tool to help everybody else do that too. So I’m excited here. Akshay, thank you for joining me.

Thank you for having me, Adrienne.

Before we get into the tech stuff, can you start by giving listeners a quick picture of your real estate background? Because you’re not just a tech founder, you’re an investor yourself.

Yes, that’s how I actually started. I was in tech building AI for more than ten years for robotic systems, not for real estate at all. But while I was doing that, I also started my own Airbnb, because in my own journey I found that freedom is the most important thing to me. And the first way I could actually start comprehending how to get freedom was financial freedom. So I started investing in real estate, living in Las Vegas, the hospitality mecca of the world. Thought it’d be great, and actually it went as planned: 92% occupancy and more. I kept increasing prices, things were going good. And then I scaled up to quite a few listings to actually get my freedom back. That’s how I experienced it, because when you start as a new Airbnb short-term rental owner, it’s deceptively taxing. We don’t realize how many small things go into not just the day to day, but also the setup of the listings and finding the listings. So I found all of that out myself, learned the hard way.

The Decision Framework for Fast, Confident Deals

July 27, 2026July 27, 2026

I sat down with Tim Kelly, a commercial real estate investor who scaled from residential deals into multifamily apartment buildings and mobile home communities through partnerships and joint ventures, and this conversation is one I think every stretched-thin real estate entrepreneur needs to hear. Tim shares the exact decision-making framework he uses under pressure, the four things a process needs before it’s actually ready to delegate, and the moment he realized that being good at doing the work was the very thing keeping him stuck. We talk about discipline, identity shifts, and why delegation without clarity is just dumping a task on someone else. If you’ve ever felt like your business can’t grow past a certain point without you personally holding it together, this one will give you a real framework to work from.

Hey everyone, welcome back. I’m Adrienne Green and today we’re here with Tim Kelly. Our listeners know we focus on how real estate entrepreneurs break free of the grind and create the freedom they really wanted at the start. And Tim is a perfect example of this, so I’m excited for you to be here and share your story with us, Tim.

Adrienne, thanks so much for having me. I’ve been looking forward to our conversation, and it’s an honor to be here.

Awesome. Well, to set the stage for our listeners, what does your real estate portfolio look like today?

So, quick version: started like a lot of people, thinking small, in residential, and then I got exposed to bigger rooms, bigger conversations, and bigger possibilities. Today my background is mostly in commercial real estate, so multifamily apartment buildings, mobile home communities through partnerships, joint ventures.

What Most Investors Get Wrong About Self-Directed Notes

July 20, 2026July 27, 2026

Most real estate entrepreneurs have no idea their retirement account could be funding their next deal. In this conversation, I sit down with Matt Moore and Courtney Ferrero from CamaPlan to break down exactly how a self-directed IRA or solo 401(k) works, the surprising range of assets you can actually hold in one (real estate, private notes, precious metals, even a dump truck), and the common mistakes new investors make when they get started. We also dig into how capital raisers and syndicators can use this tool to unlock a whole new source of investor capital. If you’ve ever wondered whether your retirement funds could be doing more for you, this episode will change how you think about that account for good.

Hello everyone. I’m Adrienne Green, and today I have two amazing guests. I have Matt Moore and Courtney Ferrero, who are here with CamaPlan. Here we focus on how real estate entrepreneurs can break free of the grind and create the freedom they wanted at the start, and this is a way you can do that with your money rather than your time. So thank you, Matt and Courtney, for being here.

Matt, let’s kick it off with you. For entrepreneurs and investors who are like, “I don’t know what CamaPlan is,” can you give us a 60-second version of what you do and who your company is built for?

Definitely. Really appreciate that generous introduction, and Courtney and I both appreciate this opportunity, so thanks very much for being able to chat with you today. CamaPlan is a self-directed IRA administrator. We opened our doors in 2003. We have thousands of clients across all 50 states, as well as DC and Puerto Rico, and we have over a billion dollars of assets under administration, so I say all that just to provide some track record on the company.

Self-Managing 19 Units Without Being On Call 24/7

July 14, 2026July 14, 2026

I sat down with Stephanie Cabral, a full-time real estate investor who built a 19-unit portfolio while working just a fraction of the hours most landlords put in. Stephanie shares the exact moment she realized she couldn’t keep being the person who answers every maintenance call, and the AI tool she built in response, called Pam, that now runs her maintenance operations while still keeping her in control. If you’ve ever felt trapped by your own portfolio, or wondered how to bring AI into your real estate business without losing oversight, this conversation will change how you think about scaling.

Hello everyone. I’m Adrienne Green and today we’re here with my friend Stephanie Cabral. Thank you for joining me, Stephanie.

Thanks so much for having me, Adrienne.

Here we focus on how real estate entrepreneurs can break free of the grind and create the freedom they wanted at the start. Stephanie is a personal example of that. She’s created the life of her dreams, and she’s created a tool to help others do the same. I’m excited to share her story and this awesome tool she built. So let’s jump in. Stephanie, before we get into the how, give us the what. What does your portfolio look like today?

I’m a full-time investor. I have 19 units, five of them are furnished, actually 19 and a half. One of them is something I control, but it will come into fruition in the future. It’s an equity play, but cash flow negative at the moment, but it will be an amazing tool in the future. So I always say 19 and a half. I was very lucky. I started buying in 2012.

The Real Cost of Doing Your Own Bookkeeping

July 6, 2026July 6, 2026

I’m Adrienne Green, and in this episode I sat down with Ana Garcia, a real estate investor and CPA who works exclusively with clients in the real estate space. Ana’s journey started in an unlikely place: a senior auditor handed her a copy of Rich Dad Poor Dad during her very first job out of college, and she’s been building wealth through real estate ever since. Today she and her husband hold fifteen doors across Miami and Broward County, spanning short-term, long-term, and midterm rentals. In this conversation, Anna pulls back the curtain on the accounting side of real estate investing that so many landlords ignore until tax season blindsides them. We talk about why cash flow, not appreciation, should drive every buying decision, the exact financial habits she recommends tracking every month, how to know when it’s time to hire help with your books, and why “more doors” doesn’t automatically mean more wealth. If you’ve ever felt overwhelmed by your bookkeeping or surprised by your tax bill, this episode is packed with practical, proactive strategies you can start using today.

I’m Adrienne Green and today we’re with Ana Garcia. Here we focus on how real estate entrepreneurs break free of the grind and get the freedom they wanted at the start. Ana’s awesome because she is an investor herself and a CPA who works with those in the real estate space. So Anna, thank you so much for joining us today.

Adrienne, so glad to be here with you.

Now for people who don’t know you, can you give us an idea what your real estate portfolio looks like today?

Right now we have fifteen doors. I say we because I own one apartment with my sister, and the rest of the fourteen doors is with my husband. So total of fifteen.

Awesome. And I’d love to hear your story of how you went from CPA to investor.

Eliminate. Automate. Delegate. The Order Matters.

July 6, 2026July 6, 2026

In this conversation, I sit down with Mike Deaton, known in the real estate world as the land guy, who spent ten years building a vacant land flipping business that now funds his entire portfolio and supports a life of full location freedom. Mike and his wife Lydia left corporate careers in 2016 after simultaneous layoffs, with no real estate income, no side hustle, and no backup plan. What they chose to do instead is what makes this conversation worth your time. We cover how they structured their business to run without them in the weeds, the eliminate-automate-delegate framework Mike carried over from 25 years in corporate operations, how they think about deploying capital across land, multifamily, and other asset classes, and why the vision behind the business matters more than the strategy. If you are a real estate investor who is still doing most of the work yourself, this conversation will give you a clearer picture of what it actually looks like to build a business that supports your life.

Hello everyone, welcome back. I’m Adrienne Green, and today we’re here with Mike Deaton. We always focus on how real estate entrepreneurs break free of the grind and create the freedom that they wanted at the start, and Mike is a perfect example. So let’s jump in here. Mike, for listeners who are just meeting you, can you give us the 60-second version of what your real estate portfolio looks like today?

Yeah, happy to. Thanks for having me on the show. So most people know me as the land guy. I’ve been for 10 years building a vacant land flipping business. And that is, I would say, 90% of what my wife and I do in terms of an income level. And that’s what we started with. But over the years, we have diversified into other asset classes, largely multifamily syndications, where we have been both passive investors and we’ve been active deal participants. We’ve partnered in over a thousand doors, around twelve hundred doors. Several of those deals have gone full cycle. So for people not familiar with syndications, a lot of time there’s a fixed value add window where you force appreciation and then there’s an exit. And so we’ve done some full cycle deals.