REI161: A BETTER WAY TO BUILD WEALTH

W/ SEAN O’DOWD

1 February 2023

In this week’s episode, Patrick Donley (@jpatrickdonley) talks with Sean O’Dowd about why he thinks there is a better way to build wealth through starting a business and using the profits to buy real estate investments. They also discuss how buying a diamond engagement ring provided the impetus for Sean to start his one man consulting shop, how he grew this side hustle into a business that nets $500,000 per year, and a unique strategy he has developed to plow 90% of his profits into building a real estate portfolio.

Sean graduated from the University of Pennsylvania’s Wharton School and worked at Boston Consulting Group. He left behind this traditional path to success to take a bet on himself and built a one-man consulting shop and dumps all of his profits into real estate.

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IN THIS EPISODE, YOU’LL LEARN:

  • How buying a diamond engagement ring provided the impetus to start a consulting side hustle
  • What he learned working for one of the top consulting firms in the country
  • How he grew his side hustle into a one-man consulting shop that nets $500,000 per year
  • Why picking the right partner in life is so important
  • Why his first real estate investments didn’t pan out
  • What his current real estate strategy is that has proven much more profitable
  • Why he thinks house hacking is a terrible idea
  • And much, much more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

[00:00:02] Sean O’Dowd: This is an unbelievable slam dunk. We have the property in the market right now in this whole area, this whole driving distance that has a huge advantage compared to everything else because of the school district. We’ve got tenants beating down our front door and they want to commit to us for years to come. Some are offering to pay years of rent in advance just to lock up our properties.

[00:00:26] Patrick Donley: Hey guys. In this week’s episode, I sat down to talk with Sean O’Dowd about why he thinks there’s a better way to build wealth through starting business and using the profits to buy real estate. We also discussed how buying a diamond engagement ring provided the impetus for Sean to start his one man consulting shop, how he grew this side hustle into a business that nets half a million dollars a year, and a unique strategy he’s developed to plow 90% of these profits into building a real estate portfolio.

[00:00:51] Patrick Donley: Sean graduated from the University of Pennsylvania’s Wharton School and worked at Boston Consulting Group. He left behind this traditional path to success to take a bet on himself and built a one-man consulting shop in a real estate portfolio that’s now approaching 2 million in value. This was a really fun interview for me and is filled with great ideas to get inspiration, both in real estate, building a business and life in general.

[00:01:13] Patrick Donley: Sean is a super smart guy and I hope you get a lot of value from our discussion today. Now, without further delay, let’s jump into this week’s episode with Sean O’Dowd.

[00:01:27] Intro: You are listening to Real Estate 101 by The Investor’s Podcast Network, where your hosts Robert Leonard and Patrick Donley, interview successful investors from various real estate investing niches to help educate you on your real estate investing journey.

[00:01:50] Patrick Donley: Welcome to the Real Estate 101 Podcast. I’m your host, Patrick Donley, and with me today is a young man I’ve been following on Twitter for a little bit recently that I’ve really enjoyed and learned a ton from, Sean O’Dowd. Sean, welcome to the show.

[00:02:02] Sean O’Dowd: Hey, thanks for having me. 

[00:02:04] Patrick Donley: Yeah, it’s great to have you on here. Really appreciate your time. I know you’re a busy guy. As I mentioned, enjoyed reading your tweets and more recently watching your YouTube videos that you’ve been putting out. You’ve put out a lot of great content. You’ve got a unique and interesting story. For our listeners who don’t know of you, talk to us a little bit about your background and why and how you’ve developed a pretty large following on real estate Twitter, which I think you’ve got a little over 20,000 followers, which is significant I think. 

[00:02:29] Sean O’Dowd: It’s funny because the Twitter thing almost happened by accident, but the headline on me is I’m Sean, I’m here in the Chicago area, was born in the area, moved a bunch growing up, went to the east coast for school, which was Wharton, then came back to the Chicago area, worked in big consulting for one of the consulting firms, left and expected I would never be back.

[00:02:48] Sean O’Dowd: One thing kind of led to another where I almost needed to start my own independent consulting firm, which I did, and it ended up growing a lot faster than I ever expected it to. I’ve always been interested in real estate, so I’ve been taking the, the money from my consulting firm and putting that into investment real estate in the Chicago area. And Twitter, I just joined a couple years ago, on a moment notice, started following, interacting with people who were saying interesting things and one thing kinda led to another and, here we’re, and it’s a much larger Twitter following than I ever expected. 

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[00:03:18] Patrick Donley: I love Twitter. For listeners who aren’t on it, I highly recommend it.

[00:03:22] Patrick Donley: Great education. As a kid, my dad’s dream for me was to go get an MBA at Wharton, and that never happened. So you fulfilled my dad’s dream, but as I said, you graduated from Wharton and I’m sure it was a great experience in many ways. I wanted to get your thoughts on the importance of higher education when it comes to real estate specifically.

[00:03:41] Patrick Donley: So having Wharton on your resume obviously gives you a lot of credibility in the eyes of others, whether it’s bankers, lenders, investors, that kind of thing. Would you encourage a younger person to pursue that traditional route of getting great grades, getting into a top school to land an investment banking job, or a consulting job?

[00:03:58] Patrick Donley: Or would you like the Sweaty startup guide in a cuber who’s been on a show, encourage somebody to maybe forego that and get their hands dirty, get started doing a side hustle, making money, get started investing in real estate. Give us your thoughts on the importance of education and how it’s played out for you.

[00:04:16] Sean O’Dowd: The short answer is I think there’s, there’s multiple different ways to kind of skin a cat here, and I think multiple past work. So the, the get good grades, get to the good school, gets a high paying job outta, outta college path is the one that I took. And honestly, I’m super fortunate that it worked out for me.

[00:04:31] Sean O’Dowd: Like there’s a lot of people try to get into really good schools every single year. Not a lot of people do. A lot of people try to get really good jobs after school, not a lot of people do. It’s a really low odds path of success. And honestly, I was quite lucky that I made it through the way I did. So if it works for you and you have that luck to get through, great.

[00:04:48] Sean O’Dowd: But I, in my opinion, I think what Nick is talking about is through a higher odds chance of success here. Like it’s a lot easier, in my opinion to start a business and get a business to $200,000 a year EBITDA than it is to go to the school, get good grades and get the job that could pay you $200,000 a year at graduation.

[00:05:06] Sean O’Dowd: But honestly, you’re probably going to be working a lot higher hours than the guy who started the business and was making grand EBITDA right off the bat. I think there’s multiple different ways to do it, and if you can go down the school path, you might as well to keep your options open. But there’s pros and concent, tradeoffs either way, and both paths definitely work.

[00:05:25] Patrick Donley: So right outta school, you did work for one, you know, a top consulting firm, and as you said, you’re now known for a one man consulting shop that nets approximately half a million dollars, which is super impressive. Talk to us about some of the learnings that you had working at that larger consulting firm that you’ve been able to carry over into the work that you’re doing today.

[00:05:43] Sean O’Dowd: That’s right. In terms of what I, where I started and what I’m doing today, I think when I think about the big consulting firm, there’s a couple big takeaways. Number one is clients are typically paying a consultant to solve their problem for them, which sounds [00:06:00] ludicrous and very basic, but at the end of the day, what I’ve found with a lot of my competitors on the independent consulting side is a lot of them tend to raise my hand and go, I’m great.

[00:06:09] Sean O’Dowd: Hire me. I can do amazing things for you. Hire me, hire me, hire me. When in reality the consultants who are the ones who are being hired are the ones who say, Hey, client, it sounds like you have this specific problem. You probably have this specific problem because you’re running into this instance in the market in my, the best way for you to have your problem solved is to do X, Y, Z thing.

[00:06:33] Sean O’Dowd: Those are the things that the big consulting firms are doing. They’re approaching clients and saying, here’s what I think your problems are and how you can solve them. While a lot of the independents are like, hire me, hire me, hire me. And if you approach it as a, the way the big consulting firms do and say, Hey, I’m here to help you.

[00:06:49] Sean O’Dowd: I understand your problems, then you’re in a much, much, much better position to actually work with that client to help them and deliver value. That’s number one, takeaway, number two, that’s really interesting from these big consulting firms, the, the bbs of the world is the consultants are not necessarily paid for the amount of work that is done.

[00:07:07] Sean O’Dowd: They’re paid for the value that is being delivered. What I mean by that, the way that I was trained, my first day at, at training for the consulting firm that I worked for was if there’s something that you’re doing and it takes you longer than five minutes to figure out how to do it, you should not be the one doing it.

[00:07:24] Sean O’Dowd: What I mean by that, and especially in the independent world, is I can put a job posting on Upwork for literally any specific skill in the world, and I can find somebody in five minutes who will do a better job than I can at a lower rate than I can. It’s almost irresponsible of me as an independent consultant to not be hiring that person and almost subcontracting that work out to them because they’re going to do a better job than I can.

[00:07:48] Sean O’Dowd: So taking that of, Hey, you know, like I can build a pretty good PowerPoint slide, or I can hire somebody who’s going to build a great PowerPoint slide and a third of the amount of time, and I can instead spend my time thinking about the client’s actual problem. I should be doing that. That’s the better use of everyone’s time.

[00:08:05] Sean O’Dowd: The last thing. So I guess the three big things that I learned from the, the large consulting firm is your job is not necessarily to find the right door, it’s to close doors down. So this is another they less they explained it, but if you of yourself as a company and you’re in of a room with an infinite number of doors and each door is open and represents different strategy.

[00:08:25] Sean O’Dowd: For example, like you could be McDonald’s and you’re working for McDonald’s, like one potential door, one potential strategy for them is to give everyone a free car when they buy a Happy Meal. Now, that’s obviously ludicrous and not going to happen, so you can close those doors down, but there’s still so many doors that could be option.

[00:08:44] Sean O’Dowd: If you’re a consultant, you don’t need to necessarily pick the right door. You need to close down doors that aren’t good options and help narrow in on what the field of options could be. That in itself is really, really valuable for clients and ends up being something that that [00:09:00] delivers a lot of value when it’s kind of a nonsensical framing when you first think about it.

[00:09:04] Sean O’Dowd: So I guess those would be the three big things. 

[00:09:06] Patrick Donley: Those are great points. How long were you at the large consulting firm before going out on your own? 

[00:09:12] Sean O’Dowd: So I was there for two years. I did basically the, the standard two year program and then bounced out on my own. 

[00:09:19] Patrick Donley: I understand that a huge part of taking that first consulting gig, and we’re going to get into the details of that here in a little bit, was the purchase of a rather pricey piece of jewelry.

[00:09:28] Patrick Donley: A a diamond ring that you bought for your, now your partner, now wife, her name is Per and I love that story, but in your case, putting yourself behind the eight ball really led to some opportunities that maybe you wouldn’t have discovered otherwise without having that added pressure. Give us the backstory on that purchase, how it developed and how it led to what you’re doing now.

[00:09:48] Patrick Donley: because you had a big bill that 

[00:09:49] Sean O’Dowd: you had to pay off. I had a big bill and I don’t recommend this at all, but it did kind of light a fire and it really worked out for me. I had met this phenomenal [00:10:00] girl. Her name was Pear, and I knew I was going to propose to her. She was and still is today the, the absolute perfect person for me.

[00:10:07] Sean O’Dowd: We met and I, I snuck away to a Julie store. There’s a big Tiffany’s on Michigan app, so I snuck over there and a really nice lady named Bonnie started showing me different, different rings they had. And I had no intention of buying a ring at the time. I wasn’t trying to do anything at that moment. But Bonnie showed me this ring that only Tiffany’s makes, or at least that they did at the time.

[00:10:28] Sean O’Dowd: That is one center stone flanked by two pair shaped diamonds. And she showed me this ring. She goes, this is called our pair ring. And I’m like, all right, well this is a done deal. I have to get this ring for my soon to be fiance named pair. So that was my decision and was like, I have to do this. I looked at the price tag.

[00:10:47] Sean O’Dowd: It was exceptionally, exceptionally high. We’re talking to Rob about roughly a six figure purchase here. And I was like, I don’t have the money to do this, but this is the right ring. And she’s like, well, we do have this lovely 0% down financing option. [00:11:00] Which me was like, okay, 0% financing. It’s a one year fixed term.

[00:11:04] Sean O’Dowd: There’s inflation. Like I’m going to be up a decent amount of money because it’s an expensive ring and inflation, like, let’s do it. So I got the ring, felt really smart, felt really good about myself for about two weeks. And then I got my first bill from Tiffany’s, which after the down payment was 4,500 bucks and I was like, oh, I need to find a way to pay this very quickly.

[00:11:24] Sean O’Dowd: That’s what led to my independent consulting career. I had left big consulting firm I was at, was working at a startup in Chicago and I basically needed a side hustle to make money. I went online, I started Googling like ways to make money today, found Upwork, which is a a large like gig economy type platform that connects freelancers and clients.

[00:11:45] Sean O’Dowd: Joined the platform, figured out a strategy to start getting clients and made 200 bucks that first day and said, okay, great. Like this is something that could work. And I just kept on doubling down on that. And granted, I was doing this at night when my girlfriend was asleep, so [00:12:00] she wouldn’t know. I was doing some weird work for some inexplicable reason to raise money, and maybe that can give something away.

[00:12:07] Sean O’Dowd: But that’s how I got started, was backing myself into the corner, finding up work and saying, okay, I need to find a way to pay my bills every two weeks. There’s a lot to be 

[00:12:15] Patrick Donley: said for putting yourself behind the eight ball. A little bit like that. Although, like you said, I don’t know if I’d recommend the stress and pressure of it.

[00:12:22] Sean O’Dowd: I definitely wouldn’t recommend it. But to your point, like there’s a, there’s a concept of burning the ships and backing yourself into a corner and having no other way to do. I think there’s ways that you can maybe artificially manufacture that pressure for yourself of like, I’m trying to hit a goal and I’m going to hit the goal by X number X day, rather than like risking your entire financial future and credit score on one particular decision, which is what I did.

[00:12:46] Sean O’Dowd: But the idea of creating some sort of a pressure for yourself, I think is important because I think it does lead you to taking steps that you haven’t taken to your date to help get to an outcome that you haven’t reached just yet. 

[00:12:57] Patrick Donley: Absolutely. It’s easy to get complacent and we [00:13:00] we’re going to get into some New Year’s goals and ideas like that here shortly, but I also, well, you mentioned Pair and I, I wanted to talk about the importance of picking the right partner in life.

[00:13:09] Patrick Donley: You give a a lot of your credit to, of your success to, to your wife. Tell us why and how she’s been such a big influence on you and what role does she play in your day-to-day activities Running the consulting firm and real. 

[00:13:22] Sean O’Dowd: So Paris, everything for me, and none of this would, would be possible without her.

[00:13:27] Sean O’Dowd: So there’s a lot of different facets that that takes on. The number one most important, like right off the board is just her unbelievable and unden denying support in me. Like I was leaving like a six figure job at 22 years old when we first met, and that was, that’s an objectively ludicrous thing to be doing, and she was unbelievably supportive of me when I was leaving.

[00:13:49] Sean O’Dowd: I was deep in the interview process with one of the very large, famous, high, high paying hedge funds and also with a tiny little startup in [00:14:00] Chicago, and I ended up at the startup and she was supportive of that when again, like I should have been putting all my time and energy into that hedge fund that I was talking to.

[00:14:07] Sean O’Dowd: So just that the unbelievable and consistent support from her has been incredible. On top of that, though, she is truly my business partner in every possible definition of that. Like if I’m doing something in my business, I’m talking about with her at night, in the morning. She’s, I guess, technically a silent partner in all of it because she’s always providing input advice, counsel on my day-to-day and what I’m doing.

[00:14:29] Sean O’Dowd: That’s specifically on the business, on the real estate side of things, everything that we do is done together. Our investment decisions are our 50 50 decisions. We make every purchase together. We make every sale together. And from a management perspective, there are some things that tend to fall on me a little bit more.

[00:14:47] Sean O’Dowd: I’m technically a licensed agent, so I tend to do more of the say showings when trying to get the properties rented. But there’s a lot of stuff that’s on the backend of real estate investing, the insurance policies, it’s working with vendors, it’s making [00:15:00] sure our tenants have paid. All of those things could fall on pair or I, and we’re very interchangeable on that cause we’re a team and at the end of the day, we’re a team in business.

[00:15:07] Sean O’Dowd: We’re a team in real estate. And it certainly wouldn’t have happened without the motivation to get pair her ring in the first place and the growth wouldn’t have happened after that. And that motivation was gone without by. 

[00:15:19] Patrick Donley: I think having the right partner is huge in life. I mean, it can make or break you honestly.

[00:15:24] Patrick Donley: That’s really awesome and I love your story, so thanks for sharing that. So Sean, I think you got paid something like $10 for that first consulting gig on Upwork, and as I mentioned earlier, you’ve now grown that to half a million dollars in net income, which is really impressive. Tell our listeners a little bit more about how Upwork works for those that would be interested in doing what you’re doing and starting a side hustle like that.

[00:15:48] Sean O’Dowd: Upwork is really large company. They’re public at this point, and they basically match clients and freelancers and consultants who are looking for work. And Upwork is great. I’ve made a lot of money in Upwork. A lot of people have [00:16:00] made a lot of money in Upwork. However, it gets criticized a little bit because it is really difficult to get started.

[00:16:06] Sean O’Dowd: The reason why is Upwork, like everything else in the world, is run on a review based system. You’ve taken Uber, you give a five star review at the end of the drive and you finish an Upwork project. A client will review you based off of five stars. Now that’s a problem for you as a new person when you first get started because when you apply for a gig and a client’s looking at the 10 people who apply, if nine of them have five star reviews and you have no reviews, cause you’re brand new, you’re at a massive, massive, massive, massive disadvantage because why should they take a risk on you when they have a known quantity at known commodity and someone else who’s already got the reviews?

[00:16:41] Sean O’Dowd: So when I first got started, I applied on hundreds of projects, had no success, couldn’t figure it out until I realized that exact point. The hack around that is you need to figure out to find projects that if you search for in the filters, have keywords immediate immediately today or urgent in their description or title.[00:17:00] 

[00:17:00] Sean O’Dowd: The reason why is those clients need somebody immediately and they don’t have the luxury of time to wait for somebody who’s got five star reviews to come up and apply for that project. If you apply for that and you’re the first person to apply, They’ll just hire you no matter what. And that’s what I did.

[00:17:17] Sean O’Dowd: So I found my first project was proofreading an email. It was for a customer dispute and my client needed somebody to look at it in the next half hour. I was the first person to apply. He didn’t care that I didn’t have reviews, he just needed somebody to read it. I applied, I got the gig. I made barely any money.

[00:17:35] Sean O’Dowd: But that’s not the point of your first projects. Your first projects needs to get rid the reviews. So I did a good job. I got the five star review. I was like, alright, ok, now I’m onto something. So I did it again. I worked for a dermatologist. I made like two bucks an hour on that particular project. But I got another five star review.

[00:17:50] Sean O’Dowd: And then I did it one more time and I got another five star review. And at that point my like per hour earnings was $1, $2, $3. It was tiny. But [00:18:00] now I had the review score on my profile and was dangerous. So then I could apply for the hundred an hour projects, the $200 an hour projects. And unlike before where I was just pitching and not getting any responses.

[00:18:12] Sean O’Dowd: Now I’m a five star review person. I was getting a lot of responses and I started interviewing for 200 an hour projects and I started winning those projects and at that point the money just starts accumulating. Cause you’re making a lot more because you took that step first of building reviews. 

[00:18:29] Patrick Donley: Yeah.

[00:18:29] Patrick Donley: That’s a great hack. And you’ve since moved on from Upwork, if I’m not correct to another platform. Tell us about that. What? What’s that platform? 

[00:18:39] Sean O’Dowd: Upwork is great when you first get started because it teaches you a lot of things like how to sell work, how to manage a client relationship, how to pay quarterly taxes, like all of these things that you don’t really think about.

[00:18:50] Sean O’Dowd: Upwork is a great learning ground for, however, what Upwork is not really going to let you do is make a couple hundred thousand dollars a year. It kinda taps out and when you reach [00:19:00] that point, you say, Hey, I’ve learned a lot, but I’m ready to go and expand. That’s when you look for a new platform. So for me that’s.

[00:19:07] Sean O’Dowd: They’re based out in Boston. Phenomenal, phenomenal company. They’ve raised a bunch of money. Mark Cuban’s an investor in them, but what’s interesting about Catalent is it’s basically the same model as Upwork of connecting consultants with clients. But in Catalent’s case, the clients are fortune hundred executives and private equity funds.

[00:19:26] Sean O’Dowd: So rather than doing a small two to three day project on Upwork for a small business owner, I’m now doing a three to five month project for the CEO of a fortune. As you can imagine, they’re paying substantially, substantially more than Upwork is. And honestly, the work is also much more interesting too.

[00:19:42] Sean O’Dowd: Like I’m currently working on a project that is going to have a huge wide range of implications for a massive, massive company. Like there will be a CNBC news article based on the projects that I’m working on right now. And that is fun because I’m actually doing something that’s going to add a lot of value.

[00:19:59] Sean O’Dowd: And [00:20:00] it’s really cool to be a part of something like that. Once you can make that step up from to a Catalent, it’s better for you from a learning perspective. It’s better for you from a project perspective. It’s better for your bank account, but it’s also just more fun cause it’s more impactful work. 

[00:20:14] Patrick Donley: Are you bringing in other outside consultants?

[00:20:16] Patrick Donley: Like you said, if it’s task that you’re not, it’s not your your thing. Are you bringing in other outside consultants to help you manage all of. 

[00:20:25] Sean O’Dowd: The short answer is yes and no. I don’t have anybody on payroll because that would crush margins, and I don’t want to do that. What I do have though, is a bench of 15 to 20 freelancers that I’ve actually hired myself through Upwork, who are very, very, very good at a specialized skill.

[00:20:42] Sean O’Dowd: For example, I’ve got somebody who works for me when I need her support. She’s got her master’s in library science. She’s a phenomenal researcher, better than I could ever be. She’s got her master in library science, so if I need her to research something, like I’ll bring her on board to do that. I’ve got somebody who is the best Excel builder I’ve ever met in [00:21:00] my entire life.

[00:21:00] Sean O’Dowd: He’s better than anyone at McKenzie, at BC’s, phenomenal when I needed an Excel, like I’ll bring him on board to help out with those particular things, but they’re coming in in the freelance capacities when I need support. They’re there, but they’re not, say a full-time employee on payroll. My next 

[00:21:16] Patrick Donley: question is a little self-serving.

[00:21:17] Patrick Donley: I wanted to go into what it’s like for you running a solo shop. Working at TIP, The Investor’s Podcast Network is very solitary. We everything’s done remotely, work from home. Lot of upsides to it. How do you handle the lack of camaraderie with workers that you used to have with working at the consulting firm, but now you don’t?

[00:21:38] Sean O’Dowd: That’s exactly the void that Twitter feels for me. To your point, like this is a relatively lonely path. Like I don’t have coworkers to talk about the game with. I don’t have someone to go on a coffee break with, and I used to do those all the time when I was working in an office. So it’s kinda lonely without having that.

[00:21:55] Sean O’Dowd: And Twitter has become that. Like there’s a lot of people I’ve got to meet on Twitter. [00:22:00] We talk a lot in the dms, we message, we text, we talk on WhatsApp, Twitter and people on Twitter have really become my colleagues in a lot of ways and it’s sounds absolutely ridiculous because Twitter is Twitter and there’s so many connotations when someone says Twitter, especially today.

[00:22:15] Sean O’Dowd: But in a lot of ways it is literally my colleague network and it’s how to prevent loneliness in this independent consulting world or any job really where you’re working home in an an independent capacity. I think a 

[00:22:27] Patrick Donley: lot of people on real estate Twitter would say that same thing. I find that there’s a lot of friendships that have developed just on real estate Twitter and it’s, it’s awesome.

[00:22:37] Patrick Donley: It’s not a hundred percent like face-to-face stuff, obviously, but it’s still, as you said, it does provide some sense of camaraderie 

[00:22:44] Sean O’Dowd: to your point. Like there’s a conference that Godfather

[00:22:51] Sean O’Dowd: California year because our youngest child was being born exactly at that time, but it is a several thousand dollars [00:23:00] ticket and flying out there, flights, hotels, whatever, would be several thousand dollars. And like I am going to be thrilled to pay that money to go to that because it’s really going to be an opportunity to go hang out with people that I’ve gotten to know and really enjoy meeting.

[00:23:13] Sean O’Dowd: It’s literally friendship to your point. 

[00:23:16] Patrick Donley: Yeah. I think you’re referring to Moses Kagan in reconvene. I am, yes. Yeah, he, he was just on here, eh, about a month ago. His episode, just No kidding, was released. His episode came out maybe a week ago. But that reconvene seems awesome and it seems like a great group of guys that are out there and I forget what it is, but it’s September, October, maybe of next year.

[00:23:36] Patrick Donley: It looks amazing. I’m hoping to go too. Well, 

[00:23:39] Sean O’Dowd: I’m looking forward to meeting you in person 

[00:23:41] Patrick Donley: there. Definitely, definitely. So you’re obviously really entrepreneurial and you launched a company at one point called Close Concierge, and you were really open. This is what kind of attracted me to you on Twitter was that you were really open and transparent about it, about its failure, and I think many people appreciate that level of [00:24:00] honesty with regard to what worked and what didn’t work with that venture.

[00:24:04] Patrick Donley: Tell us about the venture, Close Concierge, what it was, and maybe the biggest lessons that you took away from running that company. Maybe what you would’ve done differently. Looking back on things, 

[00:24:14] Sean O’Dowd: consulting has been amazing to me and I really, really enjoy it. But there’s a big, big problem with it, and the problem with consulting is you are essentially always on a hamster wheel.

[00:24:26] Sean O’Dowd: It’s really hard to take a break. It’s really hard to go on vacation, and you’re not building any equity value within the business. You’re not bringing on a staff, you’re not doing things like that. It’s basically you. Cause of that, I started about a year and a half, two years ago, looking for an opportunity to start a business and launch a business that could eventually grow and maybe even be more profitable than the consulting, but would also give the ability to take a vacation and step off the hamster wheel every while there’d be a good team underneath me that could help Facilit.

[00:24:59] Sean O’Dowd: So looking [00:25:00] around, one thing that kept on coming up is being in the real estate world, I kept on hearing agents say, Hey, I really would love a transaction coordinator, someone who is going to come in and basically help with all of the backend paperwork behind the themes that allows the agents to focus on what they like to do best, which is the actual selling of the home.

[00:25:19] Sean O’Dowd: So I said, ok, like this keeps on coming up. It seems like there’s an opportunity here. I kinda approached it as a consultant. I looked at the market opportunity. I got on the phone with a bunch of agents to ask why they were interested in even hiring for this role. Like why, why it mattered to them. I talked a bunch of freelances about what they were doing and said, you know, like, this seems like there’s actually like a really strong market potential here.

[00:25:41] Sean O’Dowd: Let’s do this. Let’s go after it. So launch the business and Close Concierge was that. And we were exactly that. We were the back office for real estate agents. What ended up being our problem and where we struggled with scale is we quickly realized, I’m saying we, because there was a team of about seven at its [00:26:00] peak.

[00:26:00] Sean O’Dowd: What we quickly realized and what we were quickly running into was that each agent runs their business in isolation and very differently to every other agent out there. For example, we would be working with one particular agent and that agent was quite unhappy with, with me and my team at one point.

[00:26:18] Sean O’Dowd: Cause we addressed one of her clients in an email as Bob rather than Mr. Jones. Was very, very, very unhappy with us because that’s how clients in her business had to be addressed. Mr. Jones, she’s like, ok, great. We’re trying to build out low-code automation so we could take on more clients. We’ll make an adjustment to that and, and we’ll say like, if agent name is blank, we’ll make sure that all of our emails are Mr.

[00:26:39] Sean O’Dowd: Jones, not Bob, for example. Then three days later, we’d run into a situation where the agent would go, Hey, I’d love to hire you guys, but I’m only hiring you if you can go into my sky slope and do XYZ as well. Ok, great. We’ll do that. So on and so forth. But we kept on running into these one-off scenarios where everybody was doing something light differently [00:27:00] and it was a non-negotiable for them.

[00:27:01] Sean O’Dowd: We had to do it that way, or they 

weren’t 

[00:27:03] Sean O’Dowd: going to bring us on. And the pie of things that we needed to do and the customization we needed to do just kept on growing and growing and growing where it got to the point where we, it just wasn’t tenable for us to scale this business. And it was either a decision of this as a small, like one person with a couple people supporting maybe UHS freelancers or go back to the independent consulting world.

[00:27:28] Sean O’Dowd: And if those were the two tradeoffs, the independent consulting world was just, it was substantially more profitable, IT smarter decision for both family. Back to consulting that kind kind of came out from that was if you’re trying to serve a million customers and do think unique for every single customer, it is really hard to do that unless that customer is a very, very, very high ticket customer who’s paying you enough that you have the infrastructure behind you to do that.

[00:27:53] Sean O’Dowd: You were a premium price. We were more expensive than every other TC service out there, which was part of our downfall [00:28:00] too. Cause we were more expensive. The agents were expecting that premium level of service where we could do their customization, but we weren’t premium priced enough that we could really facilitate that.

[00:28:10] Sean O’Dowd: And while we tried to play around with pricing, it just, it didn’t make a lot of sense for us. Interesting learning opportunities to say the least. If I had to go back and go into an industry like this again, I would go in with very premium price and a very customly concierge white service, or would go in with very low price and it’s one size fits all.

[00:28:29] Sean O’Dowd: Take her to leave it or, and this is what I would probably do. I would just acquire a business and, and run an acquired business instead where it’s already got infrastructure set up and just trying to fine tune an existing infrastructure. How long did that venture last? I was doing that venture for about a year and a half, although that is slightly misleading because I was also doing consulting work for about 75% of that time.

[00:28:55] Sean O’Dowd: So I was only actually myself fully dedicated to it, full-time about a year or so, [00:29:00] I guess. Yeah, it was about a year all in actually. 

[00:29:03] Patrick Donley: So I want to now get into real estate. We’re a real estate podcast and I want to jump into your real estate investing and your experiences that you’ve had. I understand you plow about 90% of your earnings from the consulting into real estate, maybe not now.

[00:29:18] Patrick Donley: I think it sounds like you may have taken a break, and I want to get into your kind of current market views, but what were your initial inspirations to start investing in real estate? Specifically why not some other asset class and what was the first strategy that you decided to pursue? 

[00:29:32] Sean O’Dowd: Real estate is always something I’ve been really excited about doing.

[00:29:35] Sean O’Dowd: I mentioned the very start of this. I’m originally from the Chicago area and that’s true. I was born actually like 10 minutes that direction. However, I actually moved 22 times by the time I went to. I was bouncing around all over the place, always in a new home. And I got meet a lot of real estate agents because we were constantly like leaving our house and sometimes selling it or sometimes buying but to rent.

[00:29:59] Sean O’Dowd: So just [00:30:00] the point where I’m spending of with real estate agents, I find this super fascinating. And growing up I would be in the car with my mom and we’d drive past a house with an open house sign and be like, Hey mom, please stop and go look at it. Cause we were doing it so much. I just kept on finding it more and more and more interesting.

[00:30:16] Sean O’Dowd: And then I started spending more time just scrolling Zillow. It was way back in the day when I just launched and it was always something that I knew I would really wanted to do. Once I got to college, started to get more serious about learning more, so I spent time on bigger pockets. I listed a podcast, I did things like that and I kept on coming back to this concept that seemed like everybody was talking about at the time, which is lower price, multi-family and out-of-state location.

[00:30:42] Sean O’Dowd: And those arguments for made a lot of sense for me. My wife and I said, okay, like let’s do this. She also had always wanted to be in real estate, so we started looking for property and we found a couple, we bought a seven unit in under the Illinois, Iowa border in the MO area [00:31:00] cities, and we bought a six unit up in Wisconsin.

[00:31:02] Sean O’Dowd: We were also under contract on, for one reason or another, mostly inspections. So we were in, we finally had kind of gotten started with real estate investing the way I had always kind of wanted to, and I was five years old with 13 units and felt great. I had accomplished my lifelong goal of buying real estate.

[00:31:20] Sean O’Dowd: My friends thought it was super cool and I could say I owned 13 different apartments and all that stuff. Everything was great except when you actually looked at the PNL of those properties. Cause the PNLs were never green. They were always, always, always red. And we learned a very expensive lesson for a lot of reasons on why this out-of-state, small, multi-family strategy can actually be a really, really difficult strategy to make money in.

[00:31:47] Sean O’Dowd: So we sold all those properties and, and kind of stepped back and said, is there a smarter, better way for us to be doing this? 

[00:31:53] Patrick Donley: So what was the reason, I mean, I’m sure you ran the numbers going into it and they had to look good. What was the reason they, they weren’t [00:32:00] cash flowing positively. 

[00:32:01] Sean O’Dowd: So there was a couple of different reasons that we ran into, and the reasons different differed across the different properties and different properties that we were close on a couple right off the bat because these were outta state and because these were like B minus properties, management was a necessity.

[00:32:16] Sean O’Dowd: And when you’re hiring managers, like right off the bat, that’s seven and half percent of your revenue. Right there. What’s misleading about that though is, and none of our managers charged for maintenance or anything like that, so we were like, ok, like this is going to be a good deal. Like they’re not on extra for maintenance.

[00:32:31] Sean O’Dowd: Seven, what’s misleading about that and what we experienced was when you’re talking about like a, b, C plus property of some of your tenants is going to be very, very short. So we had tenants who were going to be moving in and outta the property every four to six months, and the problem we ran into that was the property manager was taking 50% or hundred percent of that tenant’s first month rent because they had placed that tenant in the property.

[00:32:59] Sean O’Dowd: Now [00:33:00] the problem with that though is if they’re only in the property for four months and they of the first month rent, they 7%, 7%, 7%. Their weighted terms of were

[00:33:17] Sean O’Dowd: were getting killed on the management side of things, that was a huge problem that we ran into. The other thing that we ran into is, what I’ve learned is there are real estate investors everywhere. No matter where you are in the country, there’s a local real estate investor, and if you are an outstate investor and you have been upon a property online on Zillow, truly, whatever it might be, and it looks great, but it’s been sitting on the market for a hundred days, 200 days, 300 days.

[00:33:42] Sean O’Dowd: The local investors in that area saw that property couldn’t. There were local investors, they would’ve seen that property and decided to pass. And if the local investor with boots on the ground passed on the property and they know way more about the property, it’s location, the area, what everything you do as an outstate investor, if the local [00:34:00] person passed on it, there is no way that you are going to make money on it as an out-of-state person.

[00:34:05] Sean O’Dowd: And we found out later on, after we bought some of these properties, despite what our agents had told us, that they were in a very undesirable area of town for one reason or another, even though it looked great. For example, one of our properties was actually on a golf course. So like we were looking at it on Google Maps and we’re like, this looks phenomenal.

[00:34:22] Sean O’Dowd: We see the satellite photo, there’s the green, it looks great like golf course property. That’s incredible. Not a desirable area of town. Tenants didn’t want to live. Another property we owned looked great. It was a very small town. Almost every piece of multifamily real estate was owned by one of three people that were all in an entity together.

[00:34:43] Sean O’Dowd: If you were buying a property in that area and say the property manager had 90% of their business with that other entity, when a good tenant came up, the other entity was getting the good tenant. And these are things that you run into in just smaller town areas where you just [00:35:00] had a huge informational disadvantage and you’re going to be playing with local politics where you’re as an out-of-state investor, just not going to win in that situation.

[00:35:09] Sean O’Dowd: So I, I’m very skeptical on out-of-state investing unless you’re talking about buying a property that’s three 5 million. It’s got a lot of scale to it. It’s going to be fixture community. Small multifamily properties are risky out perspective. 

[00:35:28] Patrick Donley: So how did those two deals end? Did you end up selling both of them off at a loss and licking your wounds?

[00:35:34] Sean O’Dowd: Yeah, we sold ’em at a loss. We got out as fast as we could. In both cases. I think we owned the properties. I smidge more than a year and learned a very expensive lesson on those sales. Yeah. 

[00:35:47] Patrick Donley: All right. So you obviously you would not give advice to pursue out-of-state investing? It, it’s always made me nervous too.

[00:35:53] Patrick Donley: It, you know, I get why it’s somewhat popular, but I also like being local and being able to see my stuff ev just better [00:36:00] control, I think. And I think the incentives are not aligned. Like with the, you mentioned the property managers, like the incentives just aren’t often aligned and they’re not going to look out for you first, in my experience.

[00:36:12] Patrick Donley: Absolutely. Particularly if they have their own properties too. You know, like if they’ve got their own properties that they’re managing, they’re going to get the better tenants, not you. What are some other mistakes that you see newer investors making that, that you run into? 

[00:36:25] Sean O’Dowd: I think one mistake that comes up very frequently is jumping in too quickly.

[00:36:30] Sean O’Dowd: Now. I know there’s a lot of talk, you see it, a lot of talk online about the idea of like taking action and just starting to write offers, like starting to move forward, and I, I understand the genesis of those, that advice, which is, I know things are hard. It’s really hard to take that first step, so just trying to encourage two people to take that first step so they get moving.

[00:36:50] Sean O’Dowd: The problem with that in the situ is you’re missing out on what your biggest advantage can be as a real estate investor. Unless you’ve got a ton of [00:37:00] capital at hand and you can compete for a really hot property by just massively overpaying, the only advantage you have as a real estate investor is a better awareness of the market.

[00:37:10] Sean O’Dowd: That’s it. As a new investor, I would, if I say, I know I want to buy my first property in 2023, great. I would not write my first offer until July 1st. I would spend the next six months getting laser, laser laser focused on one specific zip code. And my goal should be, I’m going to know this one specific zip code.

[00:37:31] Sean O’Dowd: There’s 40,000 different zip codes in America. That’s not hard to pick. Pick one zip code, and I’m going be the best in the world at this specific zip code. And if you do that and you spend 10, 15, 20 minutes on Zillow every single day, learning that market, seeing the new house hits the, that hits the market, asking yourself, well, what do I think this house is going to sell for?

[00:37:53] Sean O’Dowd: When is it going to sell? Why is it going to do that? You’re going to get very, very, very, very in tune with what’s [00:38:00] actually happening in the market. That means once it comes time for you to actually start writing offers, you can be selective. You can be intelligent about which ones you’re picking, because when you see a hot deal hit the market, you’ll know it because you built up that informational advantage.

[00:38:15] Sean O’Dowd: And then you can move very, very, very quickly to secure the hot property. All of the properties we’ve bought have been multiple offer situations. All of those properties that we bought were on the market then off the market in 24 hours. So if you didn’t check Zillow that day, you wouldn’t have about that property because it was on and off.

[00:38:34] Sean O’Dowd: Also, because we had built the informational advantage up and spent all of our time studying the market, when a hot property hit the market, my wife and I knew immediately it was a winner. And we were the first offer in every single time we had the offers in before 9:00 AM some some cases. So, cause we had taken the time, built the advantage and could therefore identify the hot deals and then strike very fast once those hot deals hit, [00:39:00] that gave us a huge advantage over everybody else in our market and that’s why we were able to get those properties.

[00:39:05] Sean O’Dowd: And that’s the mistake I see people missing and they’re like, I’m just going to start taking action and running offers like you’re going to miss out on building that informational advantage. And you’re never going to know what those hot deals are because they’re going to be on and off really fast and you won’t have seen it.

[00:39:20] Patrick Donley: Yeah, that’s such good advice, just focusing and having a niche and knowing it really well. I think it’s awesome advice. Talk to us now about your new strategy. That first going outta state didn’t work out. You, you licked your wounds, you came back and you’ve got a new strategy that I want to hear about that I find intriguing.

[00:39:37] Sean O’Dowd: We completely flipped the script, so we knew we wanted to stay in real estate investing, and the one thing that we, we, we, we started thinking about this and we realized when people talk about real estate investing, they always talk about the asset. Like, what does this property look like? What are its, its stack?

[00:39:56] Sean O’Dowd: Is it a multi-family? How many units, how many bedrooms? That [00:40:00] sort of thing. What people tend to not focus on is who is the person who’s actually going to be living in this property, who’s the. And why would the customer rent this particular property or this particular unit compared to any other property or any other unit out there?

[00:40:15] Sean O’Dowd: And what we realized is we were looking at all of these properties is a lot of them didn’t really have a strong competitive advantage that would make it more desirable for tenant compared to anything else that was out on the market. Like, okay, maybe this one has a nicely redone kitchen, but so do these other 20 properties that are within a 20 minute drive.

[00:40:34] Sean O’Dowd: Why one property versus the other? So we decided that we wanted to find and only invest in properties that had a huge competitive advantage compared to anything else out on the market for us that was school district. So we found the absolute best school district, undisputed clear number one school district in the area and said, what does the market look like in that particular market?

[00:40:57] Sean O’Dowd: So that’s the market we picked and we zeroed [00:41:00] in on that particular market very, very quickly. What we learned very quickly, because we were studying it every single day, was that there was absolutely no rental inventory if you wanted to rent a house in that market, it just didn’t exist. It wasn’t there.

[00:41:13] Sean O’Dowd: And when we did, when there were rentals, they would be on and off Zillow in 24 hours. So you’re like, okay, like this is interesting. There’s been three or four rentals in the six months we’ve been studying this property, and they seem like they’re renting very, very, very quickly. There’s probably some, some demand here.

[00:41:29] Sean O’Dowd: Maybe we’re onto something. So that’s exactly what we did is we bought our first home in really, really, really, really good school district and said, we’ll see what happens. We were absolutely flooded. Flooded with interest in applications from tenants left right in central, who were like, I really want to be in this school district so my kid can graduate from this high school and go to the best possible college they can.

[00:41:54] Sean O’Dowd: I don’t want to buy for various reasons. A lot of them were saying, I only want to be here for four [00:42:00] years so my kid can go through high school. Like I don’t, I don’t want to buy, I know I’m going to lose money cause you should be in a house for seven years before if you’re going to buy it. So we said, okay, like this is really, really, really interesting.

[00:42:10] Sean O’Dowd: There’s a lot of interest here and nobody seems to be tapping in on it. The other cool thing about it was because tenants wanted to be there for high school, we were able to sign 100% of the, or I have 100% of the people who reached out said, I want to do a multi-year lease. Can I sign a three year lease?

[00:42:25] Sean O’Dowd: Can I sign a four year lease with you? I’m happy to put annual escalators in it, but I don’t want to have to worry about potentially moving cause it’s been so hard to find a house in the first place in this area. Can you do that? And my wife and I were talking, we’re like, this is an unbelievable slam dunk.

[00:42:41] Sean O’Dowd: Cause we have the property in the market right now in this whole area, this whole driving distance. That has a huge advantage compared to everything else because the school district, we’ve got tenants beating down our front door and they want to commit to us for years to come. Some are offering to pay years of rent in advance just to lock up our [00:43:00] properties.

[00:43:00] Sean O’Dowd: So we said slam dunk, we have to do this. We got that first property rented. First property was 440,000. Purchase price. We put 20% down, 20 year note, fixed interest out of pocket. Call it, what is it, like $90,000 to buy the property. We got that thing rented and we’ve had it for over a year now. Our cash flow on that property in year.

[00:43:22] Sean O’Dowd: It’s going to be around 15,000. So 15,000 on an 88,000 down payment. Our return on invested capital in the first year is north of 20% for this property. And it’s a class A rental, so there’s not a lot of maintenance. We hear from the tenant never because nothing ever breaks, everything’s paid on time, it’s on auto deposit.

[00:43:45] Sean O’Dowd: It’s a great, great property. So we said, let’s keep on doing this, let’s keep on unlocking this. So we kept on studying the market and every single time we saw a property that fit what we were looking for hit the market in this particular school district, we were the first ones there. And fast forward couple [00:44:00] years now, we’ve got a really nice portfolio of these properties and we still haven’t run into a situation where there wasn’t just massive, massive demand for these properties solely because of the high school district here.

[00:44:11] Patrick Donley: Did you back into that just by dumb luck or was it a strategy that you identified like, this is what we’re going to do, this is what we’re going to pursue? because I know it’s going to work. 

[00:44:20] Sean O’Dowd: It was a little bit above. So we knew that we wanted to buy a property that would have a competitive advantage that no other rental in the area would.

[00:44:29] Sean O’Dowd: So we did specifically try to buy in a great high school district knowing that high school would be, that property’s competitive advantage from the customer’s perspective, the tenant’s perspective. That property had something to offer than anything else, which was a diploma from this particular high school.

[00:44:45] Sean O’Dowd: However, what surprised us was we almost underestimated how much tenants were going to care about that and how great it was going to be for the tenants, because there’s properties that are arguably nicer than ours and two minutes outside of the high school [00:45:00] district that have sat vacant for months. For months.

[00:45:04] Sean O’Dowd: And for our properties, we had 30 applications in the first 24 hours. We knew it was going to be something that was going to be a driver for our particular properties. What we didn’t realize was how big of a driver it was going to be and how excited tenants were going to be for it. We also didn’t anticipate the multi-year leases too, which was just something that came outta nowhere.

[00:45:23] Sean O’Dowd: I wanted to 

[00:45:24] Patrick Donley: talk about that. That’s gotta be, it sounds like a key component is that the minimum you’re doing is a three year lease. Is that accurate to 

[00:45:30] Sean O’Dowd: say? The shortest lease we have is three years. 

[00:45:34] Patrick Donley: Three year lease. And then you’re also doing a 20 year loan, is that also right? 

[00:45:40] Sean O’Dowd: Yep. Three year lease and a 20 year loan on the property.

[00:45:42] Sean O’Dowd: Why’d you 

[00:45:43] Patrick Donley: decide that to go 

[00:45:44] Sean O’Dowd: with 20 years? 20 years was a function of just working with our lenders. So we do all of our transactions with a, a local lender that’s a small community bank. Really, really, really fantastic guy that we, we like quite a bit. And they were able to give us [00:46:00] just phenomenal loan terms and we really liked the people there, but they wanted them on the 20 year leases.

[00:46:05] Sean O’Dowd: So we said, Because we looked at the numbers and like the cash flow number I gave you were cash flowing a thousand dollars a month per door, and that’s with a higher mortgage payment. Cause it’s 20 lease compared to 30 years. At the end of the day we were still making a ton of profit off our investments, so we figured it was worth because we were still making money and it was what the lender was looking for.

[00:46:26] Patrick Donley: It also seems like there’s this movement for a lot of people to rent their own home. I watched my first million with Sam Far and I don’t know if you watched that show, but both of those guys are renting their own home. They don’t buy. Same thing with like Rich Dad, poor Dad. He recommend, you know, your home, he says is a liability.

[00:46:43] Patrick Donley: Did you also follow that path a little bit by renting initially to save up, to invest in your rental portfolio? 

[00:46:50] Sean O’Dowd: Yes. We had I think, three cash flowing rentals before we bought our own first property. It’s funny, one of our tenants actually is doing the exact same thing. [00:47:00] One of our tenants is renting from us, but she owns a big portfolio of properties in the Chicago area, which is like hilarious cause it’s awesome.

[00:47:07] Sean O’Dowd: Like I, she’s killing it. Hats off to her. But yes, we bought rentals before we prioritized our own property. Cause we ran all the numbers. We looked at it from a financial perspective and every single way we cut it 20 years down the line, we would end up with substantially more stable retirement if we had first prioritized buying properties for rent rather than buying properties for ourselves.

[00:47:30] Sean O’Dowd: And everybody likes to talk about like your appreciation and you can, your appreciation and your primary residence and you can sell it without taxes. Well, your rentals are going to be appreciating too, so you can sell your rentals and 10 31 them into a bigger rental. Or you can refinance them after you pay them off, pull a decent amount of money out, you still keep the properties and that refinance is cash freight.

[00:47:52] Sean O’Dowd: We did that. We did end up buying. The only reason we did was because of our kids. So we’ve got, we’ve got two kids now. [00:48:00] I’ve got a two year old and a six month old, and we had a lucky situation where there was a property on the market that fit us as a family, and that was about 30 seconds away from my parents and about A1 Minute drive away from my wife’s parents.

[00:48:15] Sean O’Dowd: We had to do it from a family perspective, but I don’t know if we would’ve done it if we hadn’t first purchased the rentals. 

[00:48:21] Patrick Donley: What does your current portfolio look like now and how, what are some of the tools that you’re using to manage it? I heard you mention a software package that you use that I wasn’t familiar with, but talk to us about your current portfolio and then how you’re manag.

[00:48:34] Sean O’Dowd: So current Ford portfolio, we’ve got four rentals in the Chicago area. Average purchase price was 4 36, all rented, all three year lease minimums. All are going to be at minimally 15% return on invested. Capital one is below 20, the other three or above 20. In terms of how we’re managing it, though, we’re entirely self-managing the properties now.

[00:48:57] Sean O’Dowd: I know that’s a scary term, but it’s actually been a [00:49:00] really not that bad process for us at all because of what the software we’re using, which is a company called Heley. Now he Lane, it’s an online rental management software that does pretty much the same thing as all of the other online rental management softwares with one unique twist.

[00:49:16] Sean O’Dowd: And what that unique twist is is they have a 24 7 team of maintenance professionals on staff. So if, for example, the furnace blows were in Chicago and one of our tenants places gets very cold, the tenant will call he Lane, not us, and say, Hey, my furnace is at He Lane will then walk, work with them to talk ’em through how to like reignite the pilot light and try to fix it.

[00:49:41] Sean O’Dowd: And Hem Lane will also get on the phone and call an HVAC company in the Chicago area. They’ll find the vendor, they’ll send the vendor out, they’ll get quotes from a couple different vendors and then they’ll email us and they’ll say, Hey, are we good to spend X, Y, Z to fix this? And we’ll email back and say Yes.

[00:49:58] Sean O’Dowd: And the whole [00:50:00] process is managed for by them and we don’t have to do anything. So it ends up being, I think it’s 60 bucks a month per. And it’s a huge, huge, huge, huge incremental savings compared to a full-time manager. But they’re doing the most time intensive thing that a manager will be doing in the first place, which is the, the actual maintenance they do, but we don’t hire them for the leasing of the properties.

[00:50:23] Sean O’Dowd: But that’s not a big lift on our side because it’s only every three years that we need to actually do that process. I’m happy to take that lift for the week or two that we’re doing it once the properties are leased. Cause it’s only, it’s only every three years or. 

[00:50:36] Patrick Donley: I like the strategy. I may consider it myself.

[00:50:39] Patrick Donley: I’ve got some lower income homes that of somebody vacated today. And it’s always a, you always, when you first walk in that once somebody leaves, you never know what you’re going to find. And it was not good today. Yeah. . Oh, oh no. Oh, I’m so sorry to hear. No, it’s all good. It’s house that I was going to renovate anyway and get it on the market, so it just a little shocking how some [00:51:00] people live.

[00:51:00] Patrick Donley: And I think with your strategy, I was thinking that with focusing on really great school districts, you’re dealing with a higher end clientele. Just a better client that I think the better tenant I should say. 

[00:51:11] Sean O’Dowd: I mean, to your point, our average rent is, is about four grand a month. So if we’re looking for someone who’s going to be qualified three times monthly income, we’re talking 12 grand a month, it’s $144,000 on the year.

[00:51:23] Sean O’Dowd: Like it’s a pretty high paying job. Like it’s gotta be somebody who’s pretty smart, pretty handy, whatever to qualify for that rental price. So our tenants are, are teachers, software engineers. Corporate executives is basically who our tenant base is. 

[00:51:37] Patrick Donley: It’s awesome. The great thing about this job is I get exposed to a lot of different strategies, but the bad thing is it’s like you get shiny, shiny object syndrome, you know?

[00:51:45] Patrick Donley: It’s like, oh, I want to pursue that now. You know, Sean’s got the right 

[00:51:48] Sean O’Dowd: idea. That’s the problem with Twitter. There’s so many people doing amazing things on Twitter. It’s like, wow. Like that’s a brilliant strategy I never thought of. I would love to do that. 

[00:51:59] Patrick Donley: One of your tweets, [00:52:00] in fact said that I wanted to get into Twitter, that you said that house hacking is a terrible strategy right now.

[00:52:06] Patrick Donley: And my co-host of the podcast, Robert Leonard, he’s got a book that he published and it came out, I think in the summertime on house hacking. Tell us about why you, and you know, typically the idea is that it’s a lower risk way to get involved in real estate, and I think has some merits, but you said it’s a terrible strategy.

[00:52:23] Patrick Donley: Talk to us about that. Why you think. 

[00:52:26] Sean O’Dowd: I am very negative on house hacking. I think the concept and the idea is brilliant, and I think before the term house hacking was talked about, pushed and there were millions of people looking to do it, it made a lot of sense. In today’s world where there are millions of people who know that term and are looking to do it, it is just a really, really, really, really tough strategy to pull off for a lot of reasons.

[00:52:53] Sean O’Dowd: Number one is a lot of people approach house hacking with the idea of, I’m going to do that with a lower down payment, I’m going [00:53:00] to do 3% down, I’m going to do 5% down. The problem with that is that forces you into a conventional conforming well, where you’ve got a bank that’s going to say, I’m not going to give you more than X, Y, Z to go out and buy this property because you’re going to be putting a smaller amount of money.

[00:53:16] Sean O’Dowd: Problem with that is, I did this for one of my YouTube videos. If you do a search in the Chicago area, which is a very, very large area, the number of properties that were not literally in need of complete renovation, I mean like literally the city of Chicago had to put a condemned sticker on the door that fit a house hacking strategy, and you could actually move in and had working plumbing was like three homes, and they were all gone immediately because there was a dozen offers and it was just too competitive of a situation.

[00:53:46] Sean O’Dowd: The odds of finding a property that you can actually house hack are really, really, really small because there’s so many other people who are trying to do it. That’s problem number one. Problem number two is let’s say you get that property, you do move [00:54:00] into that property and you do start house hack.

[00:54:02] Sean O’Dowd: Again, you’re probably going to be on a small, low down payment situation. That means, in most cases, your mortgage is going to be really, really high because you borrowed a lot of money on the mortgage, so your monthly payment’s going to be quite high. That means the house is probably not covering all of your mortgage expenses, or in fact, actually is covering a very small amount.

[00:54:25] Sean O’Dowd: For example, I’ve met people who are house hacking and they put $50,000 down to buy that multifamily unit and they’re super duper happy, because their monthly expenses on that property are thousand dollars a month versus the, say, $2,000 that the mortgage would be, they’re still down a thousand dollars a month.

[00:54:43] Sean O’Dowd: They paid 50 grand for the privilege of paying more money every single month. Would it have been smarter to instead keep renting themselves and take that 50 grand and put that into a house somewhere and put a tenant in that house where it was maybe less competitive? And then the last thing that I really don’t like about the house hacking strategy [00:55:00] is it locks you in to a really high risk situation.

[00:55:04] Sean O’Dowd: Again, low down payment, your odds of foreclosure are substantially higher. You get foreclosed upon it’s game over from your, for your finances. You’re not going to get approved for a mortgage. Again, I know there’s rules out there that are designed to try to help you get approved, but the odds are you’re not going to get approved for a mortgage again.

[00:55:21] Sean O’Dowd: The odds of you getting underwater and being literally trapped in that property and unable to sell it, are unable to move away from that property are also really, really high. In my minds. Looking at house hacking, you’re talking about a strategy that’s uber competitive right now. You might not make as much as you think you are and there’s a smarter ways to make more.

[00:55:41] Sean O’Dowd: And you’ve got a ton of downside risk. You’re literally betting your entire financial future on a high risk strategy. Like there’s other ways that you could be doing it that don’t expose you to so much risk. Like the people in real estate who’ve really, really, really made it. People been around for a long, long time, who’ve through multiple crashes, have [00:56:00] ethos of I’m going to borrow the least amount of money possible.

[00:56:04] Sean O’Dowd: 30% ltv, 40% ltv, 50% ltv. If you start g playing too much in the 96.5% LTV world, it’s really, really, really, really risky. And you’re risking a lot. 

[00:56:16] Patrick Donley: Yeah, it can definitely be a killer. Interesting points. Thanks for making those. I wanted to hear a little bit about your current thoughts now with real estate.

[00:56:22] Patrick Donley: With interest rates up. With prices up, are you looking for investments now? Are you putting your capital to work in other places? 

[00:56:30] Sean O’Dowd: We being, my wife and I are still studying the market every single day. We’re, again, knowing the market is your competitive advantage and we worked hard to build that advantage, so we don’t want to give that advantage away.

[00:56:39] Sean O’Dowd: So we’re still studying the market and if we see a good property, we’ll, we’ll, we’ll definitely move on it. That being said, you mentioned earlier like we’ve put over 90% of our money into real estate over the past couple years and there’s a world of like, we’re going to try to rebalance it a little bit so we’ve got somewhat of a buffer in other places.

[00:56:58] Sean O’Dowd: That being said, [00:57:00] if there’s a great deal, we’ll definitely move on it. We’ve, at least in our particular zip code and a couple others that we’re starting to study as well, and areas outside of Illinois are still seeing a little bit of the 2021 price hangover. What’s interesting about buying properties in single family is you’re buying them from individuals.

[00:57:20] Sean O’Dowd: You’re not buying like, it’s not like you’re buying an apartment building from another investor who’s solely emotionless and focusing on the numbers. When you’re buying a house, you’re buying someone’s house. There’s a lot of emotion that’s involved in it and we’ve seen a lot of homes where they seller saw their neighbor down the street sell their house for half a million dollars and now they want $600,000 because every price is kept on going up and like they’re sad that they missed out on all that price action and they just are still hung up on those prices we’re seeing is basically like high emotion sellers who are keeping the prices at high points, which completely understandable, but until we see prices where [00:58:00] it’s a home that fits what we’re looking for at three ride prices, it’s really hard to move on ’em.

[00:58:05] Patrick Donley: And you’re looking strictly at the MLS, you’re not sending out mailers or things like that, trying to buy houses in your particular area. It’s mostly MLS, correct. 

[00:58:14] Sean O’Dowd: Yeah, so we’re exclusively doing MLS. We have looked into the idea of doing mailers. What we found through conversation with people who have done mailers is in the vast majority of cases, the people who are receptive to mailers are selling homes that need a lot of work.

[00:58:31] Sean O’Dowd: And with my consulting business, with my wife’s job and the hours we’re both working, we don’t have the time to take on a full renovation. So we exclusively want to buy something where we can literally put it on the rental market an hour after we close, and for the reason it’s doesn’t make sense for us.

[00:58:49] Patrick Donley: Yeah, that makes sense. I wanted to talk a little bit broader kind of career advice andTIP I’m not sure if you’re familiar with with us, but we are really into Warren Buffett and [00:59:00] Charlie Munger and value-based investing. I love Charlie Munger. He, he had three rules for a great career. The first one was, don’t sell anything.

[00:59:07] Patrick Donley: You wouldn’t buy yourself. Second one was, don’t work for anyone you don’t respect and admire. And then the third one was work only with people you enjoy. I was just curious, what are your experiences with this, and is there anything that you would add to Charlie’s list? I think that’s 

[00:59:22] Sean O’Dowd: a great, great list of things right there.

[00:59:25] Sean O’Dowd: The only thing I’d add, and I think it’s a temporary thing, is don’t view yourself as too good for any particular job learning experience, whatever. My, my whole career, our whole real estate portfolio literally came from the fact that I didn’t think I was too good to turn my nose at that $2 an hour project.

[00:59:48] Sean O’Dowd: I didn’t think I was too good to proofread that email. If I did think I was too good for that and didn’t bid on those projects, I wouldn’t have gotten the review score, which wouldn’t have led to the upward earnings, which would’ve led to Catalent, which wouldn’t have led to the [01:00:00] portfolio. Being willing to say, you know what?

[01:00:03] Sean O’Dowd: Like I can do that job that no one else wants to and I’m going to learn from it and I’m going to get some sort of advantage. In this case, a review score that will therefore allow me to catapult my career is something that I think we should all be receptive and willing to do. I’m not saying make a career out of doing really not fun, $2 an hour work on Upwork.

[01:00:24] Sean O’Dowd: But I am saying, if that’s the enabler that’s going to allow you to break through, be willing to take that step and do that enabler. Because so many people, I talk about this on Twitter all the time, like take that step and try to do it. And so many people are like, that’s too low of an income. That’s not worth my time.

[01:00:41] Sean O’Dowd: Well, if you want to break through, you gotta be willing to take that. You gotta be willing to say, I’m not too good for it. 

[01:00:48] Patrick Donley: That’s a great point. We interviewed Sean Sweeney, who, I don’t know if you follow him on, on real estate Twitter, but he, smart guy, he, his first job was as a receptionist just to get his foot in the door.

[01:00:59] Patrick Donley: [01:01:00] And you know, now he’s a developer in Minneapolis. He’s done several projects. But to your point, you know, don’t have some humility and, and take some jobs that you maybe , you know, your ego wouldn’t want you to take. 

[01:01:11] Sean O’Dowd: And it’s crazy because we talked about it earlier. I went to Wharton’s, the number one business school in the world.

[01:01:16] Sean O’Dowd: A lot of my, all of my colleagues graduated and we were being billed out to clients at a thousand dollars an hour. If people I went to school with knew what I was doing on Upwork, if they knew that I was proofreading emails, they would’ve laughed at me. Literally laughed at me. But, cause I was like, you know what, I don’t, I’m willing to do this.

[01:01:34] Sean O’Dowd: It allowed me to literally slingshot up because I took that step. 

[01:01:38] Patrick Donley: Yeah, that’s such a good point. On another podcast, as I was researching you for the interview, I saw that you were a fan of Felix Dennis and his book, how To Get Rich, and I love that. I love that book. I remember reading it years ago and he’s got a great story to tell.

[01:01:51] Patrick Donley: He was the founder of Maxim Magazine and built this media con conglomerate and was incredibly wealthy, but he spends the first half of that book [01:02:00] convincing the reader to not Rich, and he says, this is a quote, great wealth. Very rarely if ever, breeds contentment. The main thing wealth provides is freedom and optionality.

[01:02:09] Patrick Donley: He’s since passed away, but he said if he were younger, he’d work his butt off till he was 35, retire with a bunch of money and then just drink white wine and write poetry on the beach or something like that. I wanted to hear your thoughts on Felix, maybe some takeaways from the book and his comments on wealth, and since I think you’re 28, how you feel about the idea of retiring at 35 and following his.

[01:02:32] Sean O’Dowd: I absolutely love that book. I, you mentioned Sam Par. I actually found out about that book because Sam Par tweeted about it a year or two ago, and I read it and it, it just really, really, really resonated with me. And I think there’s a lot of lessons in there, but the concept that he talks about of getting rich is not, not end all, be all that a lot of people thinks, think it is.

[01:02:54] Sean O’Dowd: Freedom is really the goal. Again, back at Warton, I was really, really, really lucky to be exposed [01:03:00] to some very, very, very successful, very, very wealthy people. Like we had billionaires come in and speak in class and then go out drinking with the class later on. Like, I’ve closed down a bar with one of the Sharks and Shark Tank.

[01:03:11] Sean O’Dowd: Like that’s just really, really cool experiences that you get. But what’s interesting that you learn from that is it’s really hard to be free in that scenario. Everyone, it’s hard to let it go because once you get good at a particular thing making money, it’s hard to turn that off and say, you know what?

[01:03:26] Sean O’Dowd: I’m going to step back and I’m actually going to enjoy my time with my family. I’m going to do you keep on going for the next. It’s really, really, really smart advice to approach it with the mentality of, I’m going to work really hard until I get to the point where I have freedom for the rest of my life, and then I’m going to take foot my foot off.

[01:03:49] Sean O’Dowd: I’m going to spend my time. Maybe it’s writing poetry, maybe it’s learning to dunk a basketball, maybe it’s traveling with your kids, like whatever it might be. I think that’s really good advice. So to [01:04:00] answer your question, like yeah, that’s how I have approached my entire. I have a goal notebook over here where I wake up every single morning and I’ve been doing this for almost a decade now, and I write my goals down and it’s the exact same goals every single day and its goals for the rest of my life.

[01:04:16] Sean O’Dowd: And I’m counting down days until I reach certain milestones. Like I turned 35 in 2,888 days. Like I would like to be retired in 2008, 88 days and tomorrow I’ll write down, I’ll be 35 in 2, 8 87. I want to be retired. Like I want to make sure I continue to focus on that goal. Cause making money is not the end objective.

[01:04:35] Sean O’Dowd: It’s getting the freedom that the money provides so I can spend time with my family. 

[01:04:40] Patrick Donley: That’s awesome. So you started when you were 18 doing this practice, is that right? Writing your goals down and writing ’em every morning? I 

[01:04:47] Sean O’Dowd: think if I’m counting right here, I’ve got 1, 2, 3, 4, 5, 6, 7, 8, 8 Black and decker notebooks that I’ve filled every single page, every day, all the way back to 18.

[01:04:57] Sean O’Dowd: Writing the same. It’s like four or five lines, [01:05:00] five lines I write down every single day. What was the inspiration for that? It was probably Adam Grant, who’s a Wharton professor. He’s pretty famous. He’s written a bunch of books, give and take. For example, I’m pretty sure I started it as a senior in high school cause I was going to Wharton next year and knew that Adam was going to be my professor.

[01:05:20] Sean O’Dowd: And I read something that he said about like, the importance of writing goals or blah, blah, blah, something like that. And I said, you know what? I’m going to, I’m going to do it. And I’ve done it since then. But the interesting thing to it is I’m got five lines left now. When I first started doing this at 18, it was about 10 or 11 lines because there was things that I wanted to achieve early in my twenties, the things I wanted to achieve in college, that sort of thing.

[01:05:43] Sean O’Dowd: And I have achieved every single thing that I’ve written in those goals. And when I, once I achieve it, I stop writing that goal because it’s already achieved and it’s onto the. So I’ve achieved about half of ’em thus far, and now I’ve got the other half to achieve, and if I achieve ’em all, then maybe I’ll stop doing it.

[01:05:58] Sean O’Dowd: I, I’ll stop doing it and I’ll have [01:06:00] a, a big stack of notebooks full of goals that were slowly over every day for 20 years. Crossed off. 

[01:06:07] Patrick Donley: Isn’t Adam Grant, wasn’t he like the number one ranked professor every year at, not every year, but several years at Wharton? Yeah. Yeah. That’s him. Yes. My wife for Christmas just got me one of his books that I’m, I haven’t dove into yet, but I will for sure.

[01:06:21] Patrick Donley: I’ll definitely have to check that out. I also wanted to mention, I don’t know if you’ve read Richer Wiser, happier by William Green. I think you would love that book. Check it out. Richer Wiser, happier. He interviewed the world’s top investors. You know, he’s been a journalist his entire career and he’s interviewed the world’s top investors.

[01:06:38] Patrick Donley: One of them was Nick Sleep. He’s a guy that he retired at, I think 45. Rough. But he, he had this idea of what he called the X number, like he knew his number that once he hit that he was going to be done. And he did. He returned all the money to his investors and then now he’s involved in more like charitable pursuits.

[01:06:57] Patrick Donley: But he had, he knew what he wanted to, the kinda [01:07:00] lifestyle he wanted to lead, which obviously did very well investing. But I thought that idea of like having that X number was really important and very difficult to do. because once you hit that number, let’s say you do hit it, it’s the temptation is just to say, well, maybe just a little more.

[01:07:15] Patrick Donley: Or if it’s 10 million, maybe it needs to be 15 million or it’s just really hard to stop. I think. I think it ties 

in 

[01:07:22] Sean O’Dowd: really well with what we’re talking about with Felix Dennis, of like, it’s hard, you just want to keep on going for the next goal. And you hit that and you’re like, okay, great. Like maybe I, if I do a little bit more, I can get a nicer car or do a little bit more and like, okay, now I’ll get a boat.

[01:07:37] Sean O’Dowd: And it just like you keep on doing just a little bit more, a little bit more. And it’s the trap that Felix talks about of like you get trapped in the idea of pushing when in reality your goal should be freedom, stepping back and drinking wine and writing poetry or whatever you might want it to be. I wanted 

[01:07:52] Patrick Donley: to get into books and teaching and I read that you used to be a TA at school and that you loved teaching.

[01:07:59] Patrick Donley: I wanted [01:08:00] to know if you were to teach a course on real estate for a semester, let’s say you go back to Wharton and you’re teaching a course, what would be the book or books that you would use for real estate for that class? 

[01:08:10] Sean O’Dowd: It’s a great question. And there’s a lot of good real estate books out there. My books that I would recommend though, would actually not be real estate related because I would try to broaden the student’s thinking.

[01:08:22] Sean O’Dowd: So the two books I would recommend would be here of the Empire Winston Churchill. And but what if we’re wrong? Say those again. I 

[01:08:29] Patrick Donley: gotta write this down. 

[01:08:31] Sean O’Dowd: The first one is here of the Empire Winston Churchill. It’s about Winston Churchill on his 20. And this book is really, really, really, really phenomenal because it’s the ultimate book out there about setting a goal, manifesting that goal, and making that goal happen.

[01:08:46] Sean O’Dowd: So it’s basically about how Churchill in his early twenties decided, I am going to be prime Minister of England and how can I position the next 40 years of my life to get to that goal? And he’s becomes a [01:09:00] prisoner of war. He takes crazy risks, he does all these crazy things, but he is laser focused on that goal.

[01:09:06] Sean O’Dowd: There’s like letters, other people who knew whom at the time talked about how he was like laser focused on that goal. It’s the ultimate book about like setting a goal and then the actual work and steps necessary to get there. I think it’s a good book from a real estate investing perspective because so many people come in with a goal of like, I want to have X, Y, Z cash flow per month, or I want to have this many units or this big of a portfolio.

[01:09:27] Sean O’Dowd: Great. This is a amazing book about how you can actually get there and what that looks like. So that’s the first, the second book is called, but what if We’re Wrong? Really, really, really, really interesting book that helps change your frame of thinking. And the core thesis of the book is what are we wrong about today as humans that people 300 years from now, 400 years ago from now are going to be like, how did those people believe this?

[01:09:54] Sean O’Dowd: The example it gives is Galileo and the Sun being the center of the universe, and how [01:10:00] literally everybody today in first grade learns that the sun is the center of the universe. But if you said that 300 years ago, you would be publicly mocked and you’d be publicly scorned and blah, blah, blah, blah, blah.

[01:10:09] Sean O’Dowd: And this is a New York Times bestseller from a long time ago. It changes your, your thinking to talk about what if we’re wrong? What are these things that are going to change? And it talks a lot about the economy, it talks a lot about people moving in throughout different areas in the country. Lots of interesting topics like that.

[01:10:26] Sean O’Dowd: And that book was literally the switch that flipped for me, where I was like, I’m not going to think about real estate as an asset. Like how nice is this property? How many bedrooms is this property? I’m going to flip it and think about it. Who is going to want to rent this property and why are they going to want this property?

[01:10:43] Sean O’Dowd: That’s what led to the high school strategy that ended up being the big driver of our portfolio. 

[01:10:47] Patrick Donley: Just as you were speaking about that, the whole, what if you were wrong? I watched the Bernie Madoff series that just came out on Netflix, you know, tells about his whole Ponzi scheme and he was president of NASDAQ and for the longest time [01:11:00] people are like, there’s no way Bernie Madoff is running a, a Ponzi.

[01:11:02] Patrick Donley: Like he and he, he just was able to pull off this scam for years and years and years. Until it became, you know, until it blew up in 2008 or whenever it blew up for him. But it’s the same thing. It’s like, what if we were wrong about that? And like, it should have been, people should have questioned this guy might be running a Ponzi scheme because the returns he was giving were just impossible.

[01:11:23] Patrick Donley: Really. I’d recommend watching it. If you have any interest in that. 

[01:11:27] Sean O’Dowd: I haven’t watched it, but I definitely will. I’ll put that with a list of Richard Wiser Happier. I was 

[01:11:32] Patrick Donley: watching your YouTube videos and I really enjoy them. You’ve done a really nice job on them and think they’re super informative. I think your channel’s going to grow.

[01:11:39] Patrick Donley: I noticed in a sign, I don’t see it now as we are interviewing, but there’s a sign that says get 1% better every day. You gotta be a big fan of James Clear and Atomic Habits, because that’s one of his big premises of the book, is just that small incremental changes in the long run lead to huge improvements.

[01:11:57] Patrick Donley: And like you had talked about, you, you have been [01:12:00] writing down your goals every day for the last 10 years. You started, I think at 11, you’re at five or six. So since it’s the new year and many people, many of us are creating resolutions or doing year end reviews, what are some of the ways that you are trying to get 1% better every day?

[01:12:15] Patrick Donley: And what are some of the goals that you have 

[01:12:17] Sean O’Dowd: for this year? In terms of what I’m trying to get better at every single day, it’s honestly everything. Like I approach the whole day of like, how can I be 1% better in the morning with my kids? How can I be better today at a meeting than I was yesterday? And it’s 1%, it’s tiny, tiny, tiny bit, but like, how can I just be just a smidge better every single day?

[01:12:39] Sean O’Dowd: And how can I ask for feedback at the end of meetings? Like, how could I have been better? How, and trying to gather that information to allow myself to get better. That’s something that I, I really, really, really focus and believe on because believe in, cause if you aren’t doing that, then you’re not just getting, you’re not getting better.

[01:12:53] Sean O’Dowd: And if you’re not getting better, then you’re not going to be able to learn the things that are going to enable you to do more cool, impressive [01:13:00] things down the line. Like the real estate portfolio, the whole, the first six months before you buy a property, you should be spending it studying the market. So you have that awareness that you can move on the right property.

[01:13:10] Sean O’Dowd: I kinda approached that mentality through everything in terms of how I’m applying that tactically for goals. Resolutions for, for 2023. The big one, honestly, right now is YouTube because the consulting business, it’s a relatively mature business now. It’s five, six years old at this point. It’s very stable.

[01:13:27] Sean O’Dowd: Like I know what its income’s going to be. I’ve signed on for my first project through the majority of the first half of this year. That’s like a stable thing. So the question is like, what do I grow? And YouTube is the answer. And it’s funny because I started YouTube really as a hobby because I had some time and I really liked teaching.

[01:13:46] Sean O’Dowd: I was a TA in college. It’s my favorite thing I’ve ever done. And it was like I’ve learned some things through my consulting business that hopefully I could share and maybe if it helps one person, like it’s worth the time to do that. So I started doing the YouTube videos [01:14:00] and what I realized was it’s very analytical and there’s ways to actually get a lot better at it.

[01:14:06] Sean O’Dowd: So for example, if, if you’ve never uploaded a video on YouTube, you upload a video on the creator’s backend, they can look at the video and there’s actually a chart where it shows you what percent of people were still watching the video based off of what time stamp in the video is. They call it like the retention curve.

[01:14:24] Sean O’Dowd: So I can see, for example, how many people are still watching one of my videos a minute in a minute, 30 seconds in, so on and so forth. And that is a super fun challenge for me because that’s a cool way to get 1% better. So I can look at my videos and say, okay. I said something in this last video that took the number of people who were watching my video from 80% at that moment down to 60%, which means a lot of people clicked off my video when I said that whatever I said was not helpful or negative help because people stopped watching.

[01:14:57] Sean O’Dowd: So how can I do better on the next video [01:15:00] where I don’t make the same mistake and I can keep adding value to people? And it’s a fun challenge because it literally giving me all the data you need to get 1% better. I am taking that information and I’ve also scraped a bunch of channels of, of people who’ve kinda successfully blown up on YouTube and I’m trying to marry the two together to reverse engineer their.

[01:15:19] Sean O’Dowd: That’s a long way of saying of my goal for 2023 is hoping to get the channel by the end of the year to a million monthly views. It’s a very big goal, I believe, strongly in the idea of setting like audaciously large goals. Otherwise, it’s not going to be motivating unless you, you’re really shooting for the stars and if you miss, you’re still pretty close.

[01:15:39] Sean O’Dowd: But it’s, my goal is how can I take the data YouTube’s giving with me? How can I take the data I took from the big channels, match them together to get to a million monthly views. 

[01:15:48] Patrick Donley: So how many videos are you putting out a week? 

[01:15:50] Sean O’Dowd: For the last couple months, I’ve been putting out three long form videos a week.

[01:15:54] Sean O’Dowd: Monday, Wednesday, Friday. Those videos are in the eight to 12 minute range, and I’m going to keep doing that through [01:16:00] this year, the entire of the year. What we’ve now launched as of couple days ago, we’re recording this a couple days into January, is shorts. So I’m going to start putting out a short for the four days of week where I didn’t have a long form video.

[01:16:12] Sean O’Dowd: It’s basically going to be, it’s going to be 365 videos released this year. Split between the shorts and the long form content. If you’re not familiar with YouTube, shorts is basically like YouTube’s TikTok is like a 22nd video that fits with the longer videos, you know, on YouTube. 

[01:16:27] Patrick Donley: I think I saw one of yours on Twitter, or I can’t remember, maybe it was on YouTube, but I did see one of your shorts.

[01:16:33] Patrick Donley: Has that been a huge learning curve getting into YouTube and learning that whole process? I know like for me, like I’m learning, we did a newsletter. We started a newsletter at TIP, which I would encourage everyone to read and it’s a free newsletter, can go to our website and sign up for it. But this same thing with the podcast, like it’s all like a huge learning curve for me.

[01:16:50] Patrick Donley: All of this is new stuff, but I love it, you know? And so I’m just curious what, has it been a massive learning curve for you learning how to do videos?

[01:16:58] Sean O’Dowd: It has. I am not an artsy guy. I actually like, this is dead true. I actually failed art in third grade. I am not a creative guy at all. Doing something that’s more creative, that’s more media is massive, massive learning curve.

[01:17:13] Sean O’Dowd: But it’s been a lot of fun. And it’s an area where you can attack it with the mentality of like, I don’t need to be great at this. I need to be 1% better by the end of today. If I go to sleep 1% better, that’s a win. And if you keep doing that for a year plus, like you’re going to be in a really, really, really good shape.

[01:17:30] Sean O’Dowd: The, I’ve mentioned, I scraped data from YouTube channels. Every single YouTuber I’ve found who’s blown up become a really big YouTube personality has at least 300 videos published. 300. That’s a ton of videos. Like you’re not going to blow up on YouTube very quickly if you’re doing three per week. That’s two years of YouTube.

[01:17:50] Sean O’Dowd: So if you approach it with the mentality of like, I don’t need to be Graham Stephan today. I need to be 1% better by the time I go to sleep tonight. But if I get 1% better every single day for two years, then something really cool could come out from me. 

[01:18:03] Patrick Donley: So I want to wrap up and I want to thank you for your time today.

[01:18:06] Patrick Donley: This has been a lot of fun. I’ve enjoyed talking with you. I’ve learned a lot. Not only just about real estate, but goals and all kinds of stuff. So you’ve got a lot of great stuff on Twitter. Talk to people about if they want to reach out to you, what’s the best way for them to do that? 

[01:18:20] Sean O’Dowd: There’s a couple of different ways to do it.

[01:18:21] Sean O’Dowd: My email, imsean@theodowdgroup.com feel free to email me. On Twitter, I’m quite active there, couple, almost all day. So feel free to reach out at any point on Twitter. And then YouTube, I respond to a lot of comments on YouTube, you can’t really DM on YouTube but if you want to reach out from YouTube from the comments that works too. I check all three throughout day. So any one of those three would work quite well.

[01:18:52] Patrick Donley: Awesome. Thanks so much, Sean. This has been great and I really enjoy it. 

[01:18:55] Sean O’Dowd: Thanks so much. It’s been awesome to chat. 

[01:18:57] Patrick Donley: Okay folks, that’s all I had for today’s episode. I hope you enjoyed the show and I’ll see you back here real soon. 

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[01:19:12] Outro: Every Wednesday, we teach you about Bitcoin, and every Saturday, we study billionaires and the financial markets. To access our show notes, transcripts, or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision consultant professional, this show is copyrighted by the Investor’s Podcast network.

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