.png)
The Long Game by Ryan Richards
The Long Game by Ryan Richards is a podcast about how real operators think, decide, and build for the long term — and what actually happens behind the scenes when the stakes are real.
Narrated and hosted by Ryan Richards, the show pulls back the curtain on business, real estate, and investing through unfiltered conversations with operators, investors, and builders who have earned their perspective. You’ll hear what worked, what didn’t, and the decisions most people never see or talk about publicly.
This isn’t surface-level advice or polished success stories. It’s a fly-on-the-wall look at high-caliber conversations — the mental models, systems, mistakes, and tradeoffs that shape durable success over time.
Through solo reflections and deep conversations, The Long Game gives listeners proximity to real operators and the clarity that comes from understanding how the best actually think, judge risk, and execute.
If you’re an ambitious builder who wants to learn from real experiences — not shortcuts or hype — this is an invitation inside.
Welcome to The Long Game.
The Long Game by Ryan Richards
My first rental was a disaster... but worth it | The Long Game Podcast
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
Burning down your shed can be a strong deterrent for first time rental owners… here’s what you can learn from it.
In this episode of The Long Game Podcast, Ryan shares what his first rental property actually taught him, starting with a five-unit multifamily that threw everything at him at once: evictions, bedbugs, electrical problems, non-payment of gas accounts, troubled tenants, and one tenant who burned down his shed. None of it was in the plan. All of it was education.
Ryan uses that experience as a jumping-off point for a broader framework on real estate investing: before you choose a strategy, you need to know why you're investing in the first place. The vehicle only works if it matches the goal. Someone chasing generational wealth and someone chasing quick cash are not looking for the same investment, and treating them like they are is one of the most common and costly mistakes new investors make.
He walks through the three main investing paths, flipping, multifamily, and short-term rentals like Airbnb, and maps each one to the type of investor it actually suits: the time you have, the capital you can deploy, the hands-on involvement you're willing to take on, and the long-term outcome you're building toward. The framework is simple, but most people skip it entirely.
What You'll Learn:
- Why your first investment property is almost always a crash course, and why that's exactly the point
- How to identify your core investing objective before you choose a strategy, and why getting that backwards is so costly
- The key differences between flipping, multifamily investing, and short-term rentals, and which type of investor each one actually suits
- Why multifamily is one of the most effective long-term wealth-building vehicles for investors who don't have unlimited time
- How to factor property management into your underwriting from the start so it doesn't catch you off guard later
- Why Airbnb is a business first and a real estate investment second, and what that distinction means before you commit
- How aligning your strategy with your availability, capital, and goals puts your effort in the highest-value places from day one
If you're thinking about getting into real estate investing but aren't sure which path makes sense for you, this episode gives you an honest and practical framework for making that decision before you spend a dollar.
Interested in connecting?
HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
rrichards@trynorthpoint.com | www.financewithteamrichards.com
204 Turnpike Rd, Westborough, MA 01581
Licensed in CT, FL, MA, ME, NH, RI, NC, PA, TN, VT
Follow us on Instagram @financewithteamrichards @the.longgamepodcast
#TheLongGamePodcast #FinanceWithTeamRichards
Chapters:
00:00 Starting With Purpose
00:33 First Deal Crash Course
01:24 The Long Game Mindset
01:44 Pick Your Strategy
02:32 Time Versus Effort
03:23 Multifamily With Help
03:54 Airbnb Is A Business
04:14 Define Your Objective
04:35 Final Takeaways
I didn't know all the situations I was going to run into, everything from evictions, and bedbugs, and troubled tenants. I had a tenant burn down my shed. When I started investing in real estate, I definitely didn't have all the answers, but what I did have was my long-term objective. I knew why I was doing the things that I were doing, and I think that's really important for young investors to understand. So I'm gonna talk a little bit about my story and what I knew going into it that has become more clear to me now that I think will help guide you in your investing journey When I bought my first property, I actually bought a five-unit multifamily, which is a little bit unusual for a first-time investor. But I knew that this property, in my mind, was a good deal. I didn't know all the answers, and I, I didn't know all the situations I was going to run into, everything from evictions, and bedbugs, and troubled tenants. I had a tenant burn down my shed. I had electrical problems. I had issues with the town, inspections with, with non-payment of gas accounts. I mean, everything you could probably imagine, I had at this property. It was the perfect crash course. But I knew going into it that I was going to learn a lot. I knew that at the end of the day, this was a good, a good investment. And what I really just believed in was the long-term plan. The long game is the definition of real estate investing. If your goal is to build generational wealth, you need to do it over a long period of time, and that's real estate investing. But some people don't necessarily want it for that reason. Some people want to buy real estate to make quick cash. That looks a lot different than if your goal is to build wealth over the long term. Some people wanna operate real estate as a business. Maybe you're a developer. Maybe you wanna own Airbnbs. Those are different types of avenues that all achieve different objectives. So when you're looking at real estate investing, you should understand why you're going down that path. Like, what does this mean for me? What is this going to provide for me? To make sure that the business channel you choose aligns with your goals. I know a lot of people who want to build wealth in real estate, and they're out flipping houses. Yeah, you can make some quick cash, but that requires a lot of effort, a lot of commitment, and a lot- and sometimes a lot of capital. So why would I necessarily want to do that if my goal is to retire when I'm 40, right? You'd have to do a lot of flips to do that. But if you get enough multifamily assets early enough, that can be a realistic outcome because that's more of a long-term investment vehicle. And then the type of commitment you're willing to make to that investment definitely changes what's available to you. For example, if you're someone who said, "I don't have a lot of time, but I want to invest in real estate," probably shouldn't take on a flip, right? It's a ton of work, it's a lot of effort, and it's intense. You only have six months to buy, renovate, and sell a property, and every day you don't, interest accrues, so it, it's a stressful process. But if you were someone who said,"Look, I have all the time in the world. I want to make some cash. I'm willing to do whatever it takes," maybe you don't, you have flexible hours at your job, flipping's great, right? You can make that extra income, you can put some time into the property, and you can make, you know, that objective a reality. On the contrary, if you're someone who says, "Look, I have some time, but I can't go out and swing a hammer. I would love to build some long-term wealth And I'm willing to put in some effort. Multifamily investing is perfect for that type of scenario, right? You can buy a property, you can put in a little bit of work, you can hire subcontractors to do the work, and then manage the property over the long term. And that might mean you get a property manager. Maybe you have the time to buy the property, underwrite it, go through the financing, but you don't have time to manage the maintenance requests, the repairs, the tenant challenges, the leasing, then you could opt for a property manager and just factor that into your underwriting. But if you don't know where you wanna go, you might be struggling trying to make a goal work through the wrong channel. I know a lot of people who love the idea of Airbnb. This is something I'm… This is personally something I'm very focused on in the near term, next six to twelve months. But Airbnb is a business. Real estate is the vehicle, but it is a business. So understanding that going into it can change, for some people, the decision on whether or not they actually wanna take it on. So as you start thinking about real estate investing, I just encourage you to find that core objective. Why are you doing the thing that you're doing? And make sure it aligns with your plan, because there is plenty of ways to make money in real estate investing. You just wanna make sure it matches with you, your availability, your work life, your long-term objectives, so that you're putting your effort into the highest value places. Hopefully, you took something from today, and if you ever have questions about real estate investing or business in general, find me online.
.png)