If you’ve ever dreamed about walking away from your W-2 and building a real estate business that actually creates freedom, not just more work—you’re going to want to hear this. I sat down with my longtime friend and investor Dave Menapace to unpack how he scaled from a Cape Cod rental to managing 30+ properties, launching multiple businesses, and reclaiming his time and peace of mind. We dive deep into the mindset shifts, systems, and market nuances that helped him grow 9 income streams, avoid burnout, and craft a life by design. Whether you’re early in your journey or needing your next breakthrough, Dave’s story will challenge and inspire you.
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Hey everyone, I’m Adrienne Green. And today we are with my long time friend and colleague, Dave Menapace. Get ready for insights to help you scale, systemize, and create more freedom. Thank you so much for being here with me today, Dave.
Thank you. I’m excited to be here. It’s been a fun journey since we first met.
Yes, and that’s what I love. Dave and I go way back. He was an investor when I was his agent back in Chattanooga and he was doing BRRRRs. Now Dave, you’re a full-time real estate investor and entrepreneur—your whole world is real estate now.
Yeah.
Yeah, and it’s funny, I was thinking before this—where was I when we met? Because we were virtual. It just came to me. I was sitting at the dentist’s office waiting for my appointment on BiggerPockets in the forums, and I was like, this lady Adrienne keeps popping up and we were ready to buy another house. I messaged you from there. That was probably 2020. So we’re coming up on five years. How about that?
Yeah, that’s amazing. It shows the power of just being where your ideal client is and adding value there—which I know you do so well with your co-hosting business. So before we get too far ahead of ourselves, Dave now has this co-hosting business. He’s an investor himself. He’s doing so much in the investing space. Take us back to the early days of real estate investing and share how you got to where you are today.
I love it. I’ll keep it high level because this can easily turn into a four-hour podcast, but it started in 2019. We bought a home in Cape Cod. The idea for renting it came from the listing—it said it had a rental history. I live just outside of Boston and had spent my whole life vacationing in Cape Cod. My wife Kim and I knew we wanted to continue that. We ended up buying a cool little home near the beach.
After launching that rental, we came across the book Rich Dad Poor Dad. That book really gave us the idea of settling into real estate investing. We started realizing our whole relationship to money and real estate was shifting. Quick tip for anyone: you don’t need money to buy real estate—you just need to decide you’re going to buy real estate. You’ll figure the money part out.
Fast forward about a year. Our primary and Cape homes had gone up in value. We wanted to expand our portfolio, but we didn’t want to tie up all our capital in Massachusetts. We wanted reps—real estate investing takes repetitions. That’s what led us to look at more cost-effective real estate across the country. We wanted to try renovating and long-term rentals and working with hard money. That ultimately led us to you in Chattanooga.
I live outside Boston and had gone rock climbing in Chattanooga five or six years prior. I had familiarity with Tennessee, and when we connected, the people there were just nicer—from lenders to agents to title attorneys. Everyone was willing to share their network.
I listened to a pivotal podcast on BiggerPockets. I don’t remember the episode, but someone on there said: “Take one action every day.” It could be big like closing on a house, or small like printing a form. That stuck with me. This is a game of steps, not sprints. Fast forward, and I’m at least 1500 steps down the road.
We were buying long-term rentals in Chattanooga, doing the BRRRR strategy—buy, renovate, rent, refinance, repeat—and bringing in investors as needed. After a few years, I wanted another short-term rental. I wasn’t managing my long-term rentals at that point and still don’t. We bought another short-term rental at Sunday River, a ski resort up in New England.
During that time, I got my real estate license. I just wanted to learn something new. I was done with grad school and wanted a new challenge. After buying the house in Maine, you and Harley invited me to the Short-Term Rental Wealth Conference in Nashville. That overlapped my birthday. I had already taken a swing and left my job to go full-time in real estate. I felt comfortable enough that if I took a sabbatical and needed a job, I could find one again. It was a calculated decision—and I’ve never gone back.
That conference helped me learn how to build higher cash-flow businesses that kept me out of the corporate world. One was the co-host property management business—we manage about 30 properties and are about to take on a hotel, mostly in New England. I did that so I could quickly identify sales opportunities as a realtor.
We launched a short-term rental consulting firm that helps homeowners who don’t want a manager or expensive mastermind. We also have a real estate team, and I do business coaching and run a mastermind. So from one stream of income, we’ve grown to nine—but always with thought and intention. Oh, and I have two kids too.
You really do have a lot going on. And your first non-primary purchase was in 2019. Now it’s 2025. In six years, you’ve gained so much freedom through real estate. I’d love for you to share how your daily life looks now compared to your W2 days. What freedom have you gained?
Could we maybe break that into two parts? My schedule now looks very different than it did one, two, or three years ago. There’s a self-growth evolution we all go through. It might help people to hear that.
Absolutely. So when you first left your W2 and started doing real estate full-time, what did that transition look like?
Honestly, it was less freedom at first. I was not great at owning my schedule or setting boundaries. In the short-term rental world, I had homeowners, guests, virtual assistants, team members—and of course, my family. And I treated everything with the same urgency. Everything felt like a priority. It caused a lot of friction. The family almost left. My business almost collapsed. But I’ve seen this happen to a lot of people. Growth doesn’t come without struggle. My real freedom came in the last 12 to 15 months.
So what did that evolution look like?
I had to pause and create space. Think of it like muscle recovery—if you keep working the same muscle, it can’t grow. Same goes for business and leadership. I took six weeks off last summer, only worked 3–4 hours a week, and I made more money than ever—about 10x my old W2 salary. I gave myself time to enjoy life and stopped fearing that I wouldn’t make money.
Giving space to my team allowed them to step up. I invested in leadership development so I could become a better leader and focus on the things I wanted to be obsessed with in business. When you leave a W2, you often dive into your passion project—but then it becomes more demanding than your old job. And you might be making less money. It takes business development and personal growth to turn that around.
These days, I rarely start work before 11:30 am. Thursdays are an exception when I coach students all day. Even that used to stress me out, but I reframed it. Now it’s one of my favorite days. Real freedom is here. My income isn’t tied to working eight hours—it’s tied to how effectively I lead.
I became obsessed with client satisfaction. Then I became obsessed with team satisfaction. If I could make this the best place for my team to spend their time, we’d all win. That obsession didn’t require 40 hours a week.
Now I have time to care about my health, my marriage, my kids. I realized everything doesn’t need to share the same priority. That clarity allowed me to own my time.
I learned that 100 years ago, “priority” didn’t have a plural form. We’ve made everything a priority, and that’s the problem. Having a theme or value—like client satisfaction—lets me know what to say yes or no to. Life gets easier.
This is the stuff no one teaches you. It took me facing serious personal and professional consequences to learn. But hopefully for others, the lesson can be simpler.
That’s powerful. So what are some of the things you used to think were important that you’ve since let go of?
A lot of it was fear—fear of criticism or letting people down. When you’re an entrepreneur, every client is a boss. But I was letting others’ priorities override mine. I had to stop.
I did a two-week time study. 80% of my meetings had less than a week’s notice. That showed poor planning. I was letting people insert themselves into my schedule. Now I set boundaries and plan with intention.
And I protect time. Time to think. Time to be with my family. If someone wants to chat about a market idea, that’s not urgent. My assistant can schedule it for next month. Creating space allowed me to speed up. That summer proved it—we made more than ever.
Thank you for sharing that, Dave. It’s so relatable and valuable.
My pleasure.
Let’s shift gears. You’ve worked in multiple markets—Chattanooga, the Northeast—so can you talk about how real estate investing is local and varies by region?
Totally. Real estate investing often gets treated like a spreadsheet, but it’s really about people. When I first got into Chattanooga, I flew down and met everyone—realtors, lenders, attorneys. That human element matters.
In Maine, it’s similar. But up there, vendors are hard to come by. The most successful investors fly in, spend a month getting to know the area, meeting the vendors, learning their home. That builds trust.
In Cape Cod, there’s more vendor availability, and homes are simpler. But in markets like Maine, things can fall apart fast if you don’t know your property or people. I’ve seen investors buy a home, stay two days, and then be clueless when things go wrong.
You have to invest time capital, not just financial capital. Know your market. Know what it takes to succeed there.
That’s a great point. What about snowy markets like Sunday River? What should investors be thinking about?
So many things I didn’t know. Utility costs can spike suddenly. You’re often paying for delivery of electricity, not just usage. Snow means you need plowing and shoveling—some folks don’t do both.
Water sources matter. Know the difference between a dug well and an artesian well. You don’t want a dry well with guests.
Internet access, wildlife, delivery logistics—all play a role. Costs ended up being 6x what I expected. Just assume your expenses will be higher and do your homework.
That’s so useful. We’ve gone from mindset to snow logistics—thank you for all of this, Dave. Let’s wrap with a few rapid-fire questions.
What’s a transformational system you’ve implemented in your business?
Daily systems with my team—morning check-ins, end-of-day reviews. We use L10 meetings weekly to go over KPIs and stay aligned. It’s helped us move faster with more clarity.
And your go-to tool for operations?
Monday.com. Every business I run lives in there. It’s user-friendly, powerful, and keeps me sane.
Same here. Final question—what’s one book or resource that transformed your investing journey?
Think and Grow Rich by Napoleon Hill. I’ve read it at least 50 times. It’s never start-to-finish. I open it to the chapter I need. It’s timeless. That book taught me how to think.
Also, The Last Dance documentary on Netflix about Michael Jordan. It’s about using competition to see how good you can become. That mindset applies to business too. If I get better, my clients, team, and family benefit.
I love that. And if someone wants to connect with you?
Go to davemenapace.com. You can see all my businesses and book a call with me. Or email me at dave@davemenapace.com. I’m also on Instagram and Facebook @davemenapace. I promise you’ll always leave our conversation with more value than you started with.
Thank you so much, Dave!
Thank you!