Senior Advertising Exec turns RE Investor -David McIlwaine || Ginny Bolling

David McIlwaine left a 20-year advertising career after two layoffs to become a commercial real estate investor and syndicator. He scaled from residential brokerage into multifamily deals, became a GP in A Thousand Doors, and now assembles co-GP teams from former corporate executives. His portfolio spans Kansas City, Georgia, Alabama, Arkansas, and Colorado.
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Hey, how's it sound to work less and make more? I am talking about money and there are ways to do that through commercial real estate investing. And a lot of people don't know just how easy it is to do nowadays. So this channel, Pivot to Prosperity will show you how you can do that. It's brought to you by Pivotal Real Estate Investments, where we go find the deals and do the heavy lifting and then bring you the opportunities. So if you want to know when opportunities come available, you need to register at pivotal realestate investments.com every Tuesday at 2 for about 22 minutes. We plan to bring you another video and so like share, subscribe. Thank you. Hi, Jenny Bowling here with Pivotal Real Estate Investments. And you are on the Pivot to Prosperity YouTube channel. And this is where we interview people that are in the business of syndications and those that are involved with investing in syndications or providing services for syndications. And today I have David McIlwain that we will be interviewing. And so David, if you would give us some background on you.
Hey, thanks for having me, Jenny. I'm really excited to be talking to you and your listeners. The executive summary on me is that I was a 20 plus year advertising executive. I was the sales guy that ran the central US for a whole bunch of field offices. One day I got fired. It was the response of a merger where I had hit my budgets for nine consecutive quarters. I hit my budget for the upcoming quarter the day I got fired. And it wasn't a thing about my responsibilities or my performance or anything having to do with my roles. It was about a merger out of my control. I had lived on an airplane. I was in. My favorite seat was seat 1D, aisle right hand side, first row or depending on the airplane, 13D, exit row, right hand side. I'm left handed. I wanted my left elbow in the aisle. I don't know, kind of crazy stuff. But I lived on a plane. I went through this metamorphosis, if you will. I went to a job in a tech world as a CRO for a tech company. Fast forward 24, 18 months later. I had done a series B fundraising. I had helped reverse seven quarters of negative growth to positive trends. I had actually turned the corner. We had closed on the series B fundraising. I came in the next day to execute the plan to hire 35 sales force. There are 35 sales reps across the country. My CEO said to me, hey, guess what? We paid off all our debt. I'm the CRO. I didn't know we had any debt the next day, the next week, I got laid off again. So twice in 24 months, laid off. Regardless of the performance. I looked around. I ended up becoming a single dad through this process as well. And I realized that real estate was the place to be. From there I opened my own residential brokerage. And from there I realized that multifamily was scale in my advertising world. I had sold scale in the past. So when I saw this, I knew in one minute what to do. I literally sat down in an event, in an event, listen to a speaker and changed my entire business model in my life. Fast forward a year later. I was a general partner in A Thousand Doors. I had transitioned my entire business to this. And I love it. I don't know. Is that a good summary?
Yeah, sure is. A thousand doors in one year, that's phenomenal.
Yeah, that was a good start.
And. And that was gp, lp both. Did you.
You just said that's just the GP side, LP side. I. I invested some in the LP side, but the reality is that I knew this was my profession and so I didn't spend a lot of energy and effort doing the LP side because as an LP you can't be involved since this is my profession and I already had seven years of real estate experience prior to getting into multifamily. I knew that putting my passive money to work and other people's deals was going to prohibit or preclude me from putting my skin in the game alongside my investors. And one of the most important things you can do is you can have a shared experience and a shared piece of skin in the game. If I'm not invested, why would I think my investor would want to invest? My job is to grow my net worth and my job is to grow your net worth. If I can't do both parallel, I'm not performing. So I kept my money and used it for gp, LP split.
Totally understand and totally agree with that. Yes, yes. So when you're assembling a team then, David, what, what do you have a set team that you take to any property or do you change it up based on the product that you're looking at or how do you approach that?
Great question. You know, there's a hundred different ways to skin this cat. Real estate's a team effort. What I came to learn was that I would put together a co GP model based on what works for that event at that time. And the beauty of that is that there are a lot of folks like myself who are reformed corporate America executives. We have a ton of skills and we have a ton of knowledge and experience on business and people and personnel. And so I put together a team of CO GPs that have a varied range of experience from real estate to corporate America to operational disciplines to finance disciplines. And I bring them together at a given project based on the needs. Needs at hand.
Right, right. I totally get that. And I think that timing's everything. If someone's already too entrenched with another project, you got to respect that you know or projects they may or may not have all of the bandwidth that you need. And I like to also delve into locale as well so that there's someone with local knowledge. If it's not necessarily a place that I know intimately already. I suspect those are all factors that, that you look at too well. So and your market, where, where all are you buying currently?
I have property in the Kansas City metro. I have property in Georgia, Alabama. I sold an asset to my partners and I left the partnership in Arkansas and I'm looking aggressively in Colorado. I'm based in Denver and I have lived here for 30 years. I know this market intimately. I'm also looking continuing growing in Kansas City. I just brought on an acquisitions partner in this morning. Before we started doing this we were going through a market selection exercise and I'm going to continue to be in Kansas City, I'm going to continue to be in Colorado, I'm going to continue to be in the Midwest. My buy box is typically the central time zone and the mountain time zone. Now that's a wide swath. So I think 23 is a year of evolution and change and that's going to include changing market specific selections. I foresee going a little further north than I have in the past because I think there's some honeyhole markets that people aren't talking about much. I think that Texas has some real problems in some places with insurance costs. The hurricanes have really affected insurance costs. There's no doubt about it. And I just spay is it? I what's the last most recent hurricane? Isla. Not Isla.
Ian.
Ian. Ian. I knew it was an eye. Hurricane Ian. What was the total loss? I think it was 5 billion. Is that what it was?
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