Fail Forward in Real Estate: How an ER Doctor Turned Setbacks Into Investing Experience

Temi Ajao (00:00)

I would say don’t be afraid to fail forward. Like everything is not going to be perfect. Everything may not be like a slam dunk initially. But then like that experience that you gain, it only helps you get stronger. It only helps you like be able to do analysis much better. It only allows you to keep to your gut like process, like while you’re thinking about buying deals. And I think that also it’s important to make sure that you have other investors that you’re around that you are discussing all of these things with.

Issa Hannah (02:02)

Welcome back to another episode of the Real Estate Pros Show. I’m your host, Issa Hannah, and today we have Dr. Temi Ajao with us. Dr. Temi, welcome to the show.

Temi Ajao (02:11)

Hi, good morning. Thank you so much for having me on the show. I’m excited.

Issa Hannah (02:14)

Super excited to have you. Not only are you an ER doctor, which, a lot of education, a lot of knowledge there, but about 2023, you’ve recently decided to become a real estate investor and you’re already rocking the game. So to our viewers at home, wondering, okay, what does Dr. Temi do in the real estate world, can you kind of give them a rundown of what you’re focused on nowadays and then a day-to-day in your world?

Temi Ajao (02:35)

yeah, yes, absolutely. Yes. So I got into real estate back in 2023. but my story kind of started a little bit before then. So I kind of always wanted to get into real estate because my dad is a real estate investor. He’s been investing for the past 25 years as a landlord in the Northeast. And so he’s always said to me that,

Yes, you have like the highest education, you have all this like income, But then there can always be a time where that income just goes away, right? And so it’s like, how are you building alternates alternative streams of income? And so back in 2017, which was around the time where I finished my residency, my goal was okay, let me help start building up a port a portfolio. But I got stuck in like analysis paralysis. I was like on bigger pockets, doing all the research, thinking that I needed to

approach real estate like I was approaching medicine almost, so like studying, and not making a move. So finally with work, I got burnt out with work. And I now said, what, like I’m just gonna go head forcing, get a deal. I joined a real estate investing program. And then I landed my first deal in Houston here locally and it was a seller finance deal.

where we did a rehab on it. So that was our first rehab. And it was a cosmetic rehab. So we know changed a couple of light fixtures, did some electrical work around the house, did some plumbing work. It took us about four to five weeks and yeah, basically turned a two-bedroom townhouse, made it pretty and all of that stuff. And then we threw it on Airbnb.

And the nice thing was that at that time the seller finance deal, like the mortgage was super low. because I hadn’t done an Airbnb before. So I was like, I projected that these would be the numbers, but you don’t always know exactly what you’re gonna get until you get into the deal, like for real, for real. So the first couple of years, everything’s going well and

know it’s cash flowing and all of the things and I have like people coming in and booking on the platform and then when I first started it I was like going there all the time because I wanted to make sure that I might materially participated in the deal. So I self-manage it. I don’t have any property managers or anything at that at that home. And so imagine I’m like I’m still working full time as an ER doctor.

And also managing a short term rental. And so, like I said, I went in full force and I was like, this is a lot.

Issa Hannah (04:55)

It is. It definitely is.

Temi Ajao (04:57)

And managing the guests and the, and learning how to like now go from like, okay, I’m the ones managing it directly to like now making it manage on its own. And so now for the most part it runs, it like operates itself. I have some systems in place on the back end. So it’s been operating for the last three years on its own as an Airbnb, which is which is nice.

Issa Hannah (05:18)

yeah, definitely. and shout out to your dad, as a fellow real estate investor, and former agent who’s represented hundreds of clients. I’ve had a lot of doctor clients, ER doctors. You guys have, like you said, the highest level of education. You make great money, but every doctor, when they were my client, they would always in the back of their mind, Okay, what happens when I retire? I want to live the same lifestyle. I’m not gonna say make the same money. I need to come up with different streams of income.

You guys naturally gravitate to real estate. And you guys are super good when you do jump into the real estate world because, like you said, you were doing all the analytics, you were studying, you were doing all this for a long time. in real estate, when you get good enough, you can project those numbers almost to a T sometimes. so the fact that you came in and you did a lot of reading, you came in already well prepared, more prepared than the first.

average investor. So I love that. And then having a dad in the in the business, you grew up hearing evictions, knowing the process for this, doing that. So you grew up around the game. So it’s just a matter of time I think before you got into it. And here you are since twenty three. You bought that first one. You’ve bought two more since then. Is that right?

Temi Ajao (06:24)

Yes, And so yeah, the next one that we bought, this one was a single family house as well, in the like kind of nicer area of town in the heights. And that property was like a 2500 square foot like burn property. So burn property had been on the market maybe like two or three weeks, and it was like severely undervalued.

and then yeah, pretty much jumped in, got that. So it was a full gut rehab. So now we had some experience, but to do a full gut rehab, that was like a whole it

Issa Hannah (06:58)

Well

Temi Ajao (06:59)

was a whole big project. and so it started that one. that one has finally sold.

Issa Hannah (07:04)

Wow, nice.

Temi Ajao (07:05)

Yeah. So this is the one where it took a little bit of time for it to sell. But the projections were good in the beginning. So bought it under value, probably got it for about $310,000, and then put about $150,000 of work into the house. So new roof, new plumbing, new electrical, new floor, like everything was new, like foundation work and all of that was new. But the issue with it was that when

We bought it, the single family has always been used as a commercial property. And so people had used it in the past for like a yoga studio. People have used it as a gym before. And so initially, when first doing the analytics, the goal was to now convert it from because it was a two-bedroom, two bedroom, one and a half bath. And so a ton of space, huge lost space in the back that was like 800 and something square feet.

And massive property. so initially the goal was to convert it to a three-bedroom or four bedroom and two-bath. But then I think the contractor that I was working with

the contract and the architect, they kind of talked me out of my gut of what I wanted to do with the property. They were like saying, the city’s gonna give us all these problems, the city’s gonna do this, the city’s gonna do that. And I realize that as a real estate investor, a lot of the times you have to trust your own gut. Like you have to trust what you think you can do with a deal. And but I

kind of let them talk me out of it because I felt like, well, they have more experience than I do. And I’m not entirely sure like what the city’s going to do. Cause I never had to, the first property I didn’t really have to pull any permits. But then this one I did have to pull permits. And so there was a little bit of fear and doubt that was there that I said, okay, what, let me just convert it back to the original, like what it was, what it is already. But I think that slight decision there is what cost me

So much time in holding costs. So I ended up helding that property for almost, two years before it finally sold. And beautiful property. People will come, they would walk it, they would say, This looks great, it’s wonderful, da-da-da-da-da. But then there was some other factors that would not allow them to buy the deal. Or they would say that

there’s not enough parking in the area. Like cause especially if it was a commercial property and I had a restaurant that wanted to come and buy the property, but then they were saying that, there’s not enough parking. And those are some of the things that I’m like, mm, see when you go for the next deal, that’s not happening again.

Issa Hannah (09:31)

Mm-hmm. Hundred percent. You live and you never lose, you always learn. So even if you sat there and you held it, you were sitting there learning, like, okay, I should have listened to my gut because the residential, a single family home would have sold like that much quicker, especially totally brand new. And then wow, the education you’re already getting. Your second property you had to rehab a fire damaged property. fire

yeah.

I probably was in the game ten years before I had to touch a fire damage property. And guys at home, fire damage is not it’s one of the hardest ones to do because you have to A get the property up to the new code. So let’s say that property was built before five, built before the new codes came out. Yes. now you’ve got to update it to the new code. You’ve got to pull permits for everything. They scrutinize everything. Before you even go in there, you have to let the house basically

Air out, you can’t even go in there for like two to three months. So the fact that you got it done on your second deal, and you’ve sold it, right? You sold

Temi Ajao (10:26)

it’s so yeah, it’s sold now.

Issa Hannah (10:27)

There you go. you learned that right there. It is years worth of investor knowledge that you gain just by doing that. And then you have the good gut for the investor. you knew that it would have sold a lot quicker had you done your original plan. And to my investors at home, a lot of times, they could be the best contractor, but they don’t want to have static with the city. They don’t want to

have to go above and beyond for the city. So a lot of times when they try to like, sway your mind this way and away from it, it’s for them. It’s not for you. So, this is just investor to investor. I wanted to share that. And now I want to ask you, you kind of touched on a little bit of a nightmare. I want to get the nightmare from you now. give us your biggest real estate nightmare that you’ve had so far in your investing career.

Temi Ajao (12:01)

Yeah, that second deal, It was really tough. And the holding, the macroeconomics of the environment changed. And so, it got to a point where okay, now this how the house is fully rehabbed and ready to go and it’s on the market. It sat on the market. and I think a lot of it was because.

The house it appraised for the post appraised for about 700 and something thousand dollars. So we’re talking, bought it in for 310, put in 150K of work, and it appraised to, the projected numbers, which was wonderful. But then the the type of buyer that’s gonna go in for that type of property is not always gonna be your like first-time home buyer, And then at that time, 2024.

Interest rates are, are quite high. And so, there’s going to be a difficulty with, people coming in that need to have the down payment to be able to get that type of house. and then two, with the interest rates too, it’s like, well, because of the style of the property, people wanted more bathroom space, all of the things. So then I was like forced to think of, okay, who else could buy this?

And so at that, there was a point where church wanted to actually buy the house. And I was even thinking of doing creative with them because my first deal was creative. I bought it on seller finance. And so I was like, I’m open to doing seller finance. you guys can come. I don’t care. Take the property.

Issa Hannah (13:24)

A hundred percent.

Temi Ajao (13:25)

But then at the same time, because of the all in cost and because of like everything that has been spent, I was getting a lot of lowball offers. And I was like, well, I can’t I can’t do that. So I we just ended up holding on to the property quite a bit. So then now I get to a point where it’s like, what do I do? Do I just come continue with these holding costs or refinance? So I’m like, okay, boom,

we need to get out of this interest debt, this high interest debt. and so we ended up refinancing, thank God. But the refinance process, it took a lot longer too than I expected. There was a few hiccups along the road. even with like the appraisal, they wanted an app, I think they did like three or four appraisals. And I was like, I don’t know why we keep on doing all these appraisals. This is what this house is worth.

Like say like, okay, we’re gonna do a desktop appraisal. All right, we’re gonna come in and do an appraisal. Okay, now we gotta do one more appraisal. So I was like, okay, continue to do the appraisals. Every time the appraisal came back at what we projected it to be. And so then finally we were able to refinance. And even I think we were going to refinance into a DSCR loan. But then we met the,

rental DSCR rates or something like that. And so then they were like, we can’t do a DSCR loan on this deal for the refinance. And I’m like, okay. But luckily I was working with a loan officer who was resilient. That man blessed our life. Like he was like, okay, we’re gonna get this deal closed regardless.

And so we ended up doing a bank statement loan because I’m a ER physician and I have that income to support it. We were able to do a bank statement loan and then refinance out of the deal in that way. And so that was our saving grace. So paid off the private money person, paid off the hard money people, everybody was happy, and then now we got to move forward as well until we were able to sell the house. But yeah, it’s

Issa Hannah (15:18)

100%. It does take a bit of fiery damage property financing issues. but you got through it on the other side, and now you’ve gained so much knowledge from encountering these problems because yeah, you do have to deal with it. One of your strengths you said was you’re resilient. you’re not gonna give up. So you didn’t give up, you made it through, and you’re that much more knowledgeable in the real estate industry because of it. And I want to make another point to my viewers. a good loan officer.

Every loan officer is not created equal, you guys. Everybody has their specialties. Exactly. And they need to fight for their client A. B, they need to be very well versed on all the different products. because when you when you do talk to a client, you’re having a conversation. But in your mind, as a loan officer, you should know what loan product to put that person in and what backups,

that you would have to pivot. So shout out to your lone person because yeah having a good one like that, man, they make it so much more easier and so and less stress free. So quite a nightmare story for sure, especially for your second property. But wow, you got through it and I know that now you ever encounter something like that again. It’s one, two, three, you’re gonna be able to get through it.

Temi Ajao (16:24)

One to

three. yeah. Yeah.

Issa Hannah (16:26)

And then five years down the line, I know you’re an ER physician. I know you’re probably gonna do it for a lot more than five years, but real estate wise five years, where am I gonna see you out? How many properties? what’s the number in your mind?

Temi Ajao (17:20)

Yeah, five years from now, I hope to have at least 20, to 25. that would be the goal. And and it would be a mixture of like multifamily units and working in partnership with other people. But I think that this real estate journey, it makes a lot of sense when we work in partnership. and I think you can scale faster that way, and then you have multiple heads looking at the same deal.

you work together as a team. because I’m like my background as an ER physician, everything we do is working in teams. And so I think that it just makes sense that that’s where I would head towards in the future of my real estate business. because I’m also still gonna work as an ER physician. I would never really quit, but I will probably scale back quite a bit. and so in that process, I see myself

Doing both. So working a couple of shifts here and there, but then also like working on my real estate business, scaling that, like bringing people together, talking about generational wealth, like really helping everybody kind of gain freedom in that sense. And it’s more so like time freedom. That’s what I think everyone is kind of looking for is that time freedom, having alternate sources of income, having passive cash flow, like true passive money. and so.

Kind of that’s the goal that I see myself in the next few years.

Issa Hannah (18:34)

I love that because it’s one thing you can’t buy is time. You can’t buy that with money. But you can buy it if you have a lot of rental properties, right? you see the real estate investor. We might be stressed out, we might have a million things to do, but we’re doing it from home. We’re doing it we’re doing it on our own time. We don’t have to clock in, we don’t have to clock out. which is true financial freedom. You guys, true freedom in life to have

Tammy, I do not doubt that you’re gonna crush these goals. you’ve already learned so much in the few years that you’ve been doing it. You get around some other investors, like they say, forget about it. it’s gonna scale up so quickly. It’s unbelievable. I wanna get your advice now for our younger viewers, right? Our new investors. You, I would say you’re pretty seasoned by this point. with all the stuff you’ve gone through. But two new investors, our

the ones that are doing the research and haven’t jumped in yet, if you could give one piece of advice, what piece of advice would that be?

Temi Ajao (19:27)

I would say don’t be afraid to fail forward. Like everything is not going to be perfect. Everything may not be like a slam dunk initially. But then like that experience that you gain, it only helps you get stronger. It only helps you like be able to do analysis much better. It only allows you to keep to your gut like process, like while you’re thinking about buying deals.

And I think that also it’s important to make sure that you have other investors that you’re around that you are discussing all of these things with. Cause a lot of the times, we might have our own vision about what we want. But then another investor might be thinking or might say to you, Hey, have you thought about this? Have you thought about this roadblock? Or when I had this deal, this is what happened. you may not want to repeat what happened with me and XYZ, So

There’s plenty of times where like in my investing group that I was a part of, that they, we analyze a couple of deals together and they’re like, mm, and in my mind I’m like, there’s a great deal. Let’s go. I’m gonna get this. And they’re like, mm, are you sure? And then once they put that in and then re-analyze, then you see that, actually that might be a good deal, but maybe for somebody else or a different time or a different environment, a different macro environment, things like that. So

I think working in teams and like in partnerships really will help you like do well in this business.

Issa Hannah (20:45)

One hundred percent. Because you you’ve got a council of seasoned investors who who’ve seen things that you may not have seen, know how to look at it with a different lens. and investor fuel here. We have about two hundred of very high level operator investors that work together, counsel each other to make their businesses better. So one hundred percent you’re right on that. we believe wholeheartedly in that,

you have some stuff cooking up social media wise. y

Temi Ajao (21:11)

Yes.

Issa Hannah (21:12)

you have a couple of things going. So I’m gonna give you the floor. If people wanted to get a hold of you, follow you on socials, how could they reach you? And what are what do you have cooking up?

Temi Ajao (21:20)

in addition to being an ER physician and real estate investor, I talk a lot about money. And so I’m a financial coach. I do Money Mindset MD Podcast and I pretty much bring a lot of investors onto the platform to talk about like their mindset about money. anybody has any issues with financial trauma or financial anxiety, how to overcome that.

I have worked with clients in the past who have had like, some analysis, paralysis when it comes to their money, or just kind of a different fixed mindset, a scarcity mindset and how we move that towards more having abundance and a growth mindset. And really it’s just about learning where to put your money. Cause it’s one thing to have a high income, but then if you’re not like strategizing it well, if you’re not like diversifying your portfolio or even stewarding your money well.

you can still find yourself living paycheck to paycheck. And so I talked a lot about that on that platform. And so I’m on Instagram, I’m on all the socials. I have a website, www.moneymindsetmd.com. And then also I have a podcast. It’s on Apple podcasts, YouTube now, we’ve transitioned to there. And so all the links are there too. And so if you want to reach out to me, talk to me, see what we talk about.

I am on Facebook, LinkedIn and Instagram.

Issa Hannah (22:35)

Make sure you guys check Dr. Temi out. Money Mindset MD. truly, unbelievable. You’ve you’re wearing so many hats, you got so many things going on and you’re killing all of them. and then to my viewers at home, someone like Dr. Temi who who’s, had the money, made the money, knows about taxes, knows about interest rates, knows this, knows that. She knows how to move in the financial world.

she has a knowledge that a lot of people stuff. So the fact that she’s out here on all the socials trying to give you her knowledge, you better go follow her. So Money Mindset MD on all platforms. You guys make sure to go follow, like, subscribe, everything. And then Dr. Temi it was so, fun to talk to you today. I was truly an honor to host you.

Temi Ajao (23:17)

Thank you. Thank you. Thank you for

Issa Hannah (23:20)

I was super excited to have you and I’m gonna invite you back on the show at a later date. I’m gonna save your number and I expect a text in a few months from me.

Temi Ajao (23:28)

Okay, awesome.

Issa Hannah (23:29)

And to my viewers at home, if you guys enjoyed my conversation with Dr. Temi and want to see more like it, make sure to hit like and subscribe. I talk to people every day that can bring us different knowledge on every aspect of the real estate industry. Until next time, the Real Estate Pros are out.