Rookie Reply: How Tony Robinson Lost His Job (and Found His Freedom)

Dec 3, 2022

Getting fired usually isn’t a good thing. But in retrospect, it was arguably one of the best things to ever happen to Tony Robinson. Before being the internet’s poster boy for short-term rental investing, Tony Robinson spent his days working for someone else while climbing up the corporate ladder. When he unexpectedly got fired (2 days before Christmas), he had to reimagine what his life would and could look like.

Tony took a chance on himself and his real estate business, a chance that has paid off massive dividends to this day. He now lives life on the schedule he wants, spending time with his wife and son, without having to worry about a boss one day letting him go.

If you want Ashley and Tony to answer a real estate question, you can post in the Real Estate Rookie Facebook Group! Or, call us at the Rookie Request Line (1-888-5-ROOKIE).

Ashley: This is Real Estate Rookie, episode 146. My name is Ashley Kehr living my best Alex Cooper life in a full matching sweatsuit launching on my couch with microphone at hand, with my lovely co-host Tony Robinson, the same black shirt he wears for every recording.

Tony: This is actually a new black shirt that I got for Christmas. So, I got several black shirts for Christmas, but if this is your first time hanging out with me and Ashley, welcome to the Real Estate Rookie Podcast where every week twice a week, we bring you the inspiration, information, motivation that you need to get started and to keep going in your real estate investing journey. So, Ash, what have we got on the docket for today?

Ashley: So, we had talked about this a little couple of days ago, and I really want to do this as our Rookie reply. So, you did an Instagram post about how last year. So, this was right around the time you had just become the podcast host and you had gotten fired from your job. I would love to talk about that because we had the conversation. When you got fired, as to say you were just going to take some time off, you guys were going on your honeymoon, different things, and then you were going to start applying and getting a new job. And I said, I don’t think you’ll ever go back, ha, ha, ha. But okay, good luck. And so, let’s follow through, what has happened.

Tony: Yeah. So yeah. So, if you guys didn’t see, if you guys haven’t followed me on Instagram, it’s @tonyjrobinson, but I posted December 23rd will be a day that the kind of really important day for me, for my family, because December 23rd of 2020, I got fired for my job and unexpected kind of out of the blue.

Ashley: And right before Christmas too.

Tony: Two days before Christmas, I’ve been married for a month, like you said, my honeymoon was coming up. So, just a lot of weird thing, just really weird timing. And like most people after you get fired, you’re kind of in shock. There’s some in fear that kind of rushes over you, I think like most people. And like I shared with Ashley, my initial instinct was okay, cool. Let me go out and find another job. I was a senior level manager at my last company and I had a really big team and I had kind of climbed the corporate ladder. But when you get fired from somewhere trying to go out and find something else is a little bit more difficult, right? Regardless of what the reason is you got fired, there’s kind of this stigma that comes along with that. So, it becomes increasingly difficult to kind of find something that’s comparable to what you had before. So, I went on several interviews, put in a bunch of applications and I would go through the whole song and dance and do all the interviews and shake hands and do all those things you’re supposed to do, but I got rejection after rejection. So, I had a decision to make at that point. It’s do I go out and find some other job where maybe I’m overqualified and underpaid because I did get a job offer, but it was for a job that I [inaudible 00:03:01] would’ve taken like four years before, right? When I was fresh out of college, didn’t have as much experience and a fraction of what I was making at my last job. So I could go out, I could find a job where I was overqualified, underpaid, or I could use that as an opportunity to kind of bet on myself and see just how big I could go grow the business that we had started. So, made the decision to better myself and it was quite the wild 12 months ever since.

Ashley: Was there one moment where you were like, okay, that said I’m going full time into real estate, I’m going to make this work or was it more like gradual, like wow, this is actually working for me continuously buying short term rentals?

Tony: Yeah. There was kind of a moment, and two moments really. One was, I had tried to get a job at a company that I worked for before and I left there on good terms. I crushed it when I was there. I was doing a good job kind of climbing up the corporate ladder there as well. And the job that they offered me was the job that I had mentioned, where it was a job that I was overqualified for. I knew to my core that the skill sets that I had and the ability that I had was going to be underutilized in that role. And along with that, the compensation was going to be far less than what I was accustomed to as well. And it was at that moment that I kind of had this epiphany that it’s like, okay, if that’s what the job market is for me right now. If this is a company that already knows what I’m capable of and this is the best that they’re willing to offer me, how many more companies had never heard of Tony J. Robinson, what are they going to do for me? So, I think it was in that moment that I’d sit down with Sarah, my wife and I was like, “Hey, I think that the universe is kind of pointing us in this direction that we need to and pause and take a moment to really double down and better on ourselves.” And the craziest thing Ashley, was that I lost my job on December 23rd. The first podcast episode that I was on for BP came out six weeks before. And when I’m looking at this, I’m like, “Man, here’s this opportunity that I thought that was gone with stepping into the Rookie show and out of nowhere, that opportunity comes back.” And then six weeks later, my job, this ability that I have with that, that gets taken away. It just kind of felt like those two things happen too close to each other for it to be coincidence, for me not to capitalize on opportunity.

Ashley: Let’s kind of tell the backstory of that too, when they first announced that there was going to be another BiggerPockets Podcast that you were in the top three as a contender. And when you didn’t get it that first round like you said you thought that it was over and then less than a year later, you find out that you do get it and you’re in now, and then you get it fired from your job. Do you want to just explain briefly why you got fired? Because I think it’s very important because there wasn’t something that happened or you did a bad job. It was just like almost a weird situation that could happen to anyone. And I think that’s, you don’t have to say who you worked for or whatever, but just to, I think to briefly explain because this could really happen to anyone.

Tony: Yeah, no for sure. I mean, I don’t want to get too deep into the weeds on it, but it wasn’t performance related. I had just gotten promoted. I was crushing it. I was very well received by the leadership team there, but there was a policy that I wasn’t too familiar with that I wasn’t following, that my team wasn’t following. And because I was the senior manager of this big organization, they felt that it was my responsibility to really know the ins and outs of all the different policies that my team should be following. So, because this policy wasn’t being followed in my organization, they said, “Hey, Tony, you’re the person that’s responsible for making sure that that’s in place.” And they let me go for that reason.

Ashley: The reason I want to bring that up is because when you’re working a job, when you’re working for someone else, you don’t have control over those situations. But now Tony, as entrepreneur, he gets to make his own policies and gets to decide what happens. And I wanted to bring that up just to showcase how constrained you are as an employee in your job. And of course not all jobs at all, but just, you have it so much better now, especially being my co-host.

Tony: That’s the best part. But I mean, but here’s the truth, Ashley, is that the day that I got fired, I had coworkers, people who worked for me, they all reached out to me and said, “Tony, we can’t believe that this happened. We’re all going to miss you.” But the company kept moving. Nothing stopped because Tony left, right? The company didn’t come crumbling down because I was fired. And I think that’s the part that really stood out to me is that, and this isn’t me trying to having this ego being like, oh my God, I was so important that, but it’s just a humbling reminder that 99% of people who work at W-2, if you die today, you would get replaced tomorrow and things would keep moving. There are very few people who are irreplaceable within their company. Even the people that start the companies, right? You think when Steve Jobs died and he left Apple, Apple has now become a multi-trillion dollar company even without Steve Jobs. And that’s the truth about a lot of these W-2 positions is that even if you feel secure, even if you feel safe, you are one downsizing away, you are one merger away, you are one economic recession, you are one not getting along with your manager away from potentially losing your job. And I just feel blessed that I never fully relied on just my W-2 as my only source of income and financial security and that while I was climbing that corporate ladder, I was also in the background building my own personal financial foundation that I could fall back on.

Ashley: Having those multiple income streams. Because if one of those legs give out no pun intended on my leg, you have another leg to stand on. But and that’s such a great point as to if you are working a W-2 job and you don’t like it or you don’t want to be stuck in it, or you don’t know if it’s going to last forever, start building that side hustle, that side business, that real estate empire now, because there are so many ways to get started in real estate while working your full-time job. And I’ve seen this post so many times on Instagram lately is about how your W-2 job should that money should be used to fuel your real estate business and to be putting that money into it. And that’s what the purpose of your W-2 job is to feed into investing in real estate and use those funds you make from your W-2 to buy properties, to invest in real estate, to pay for rehabs or whatever it is. And I think that’s such a great point is to you don’t have to quit your job to become a real estate investor. And there are people that make it work. They decide, I’m quitting right now and I’m going to just be a full time investor and go full blown. But there’s also people that work for 10 more years and build up their empire and use their W-2 job to kind of fund it and get it going and then maybe they retire and quit their job. So, there’s so many different ways to do it.

Tony: Yeah, I mean, and that’s the kind of situation we were in is where we were living on, I don’t know, maybe like 30% of what we were making from my W-2 job. And the rest was just kind of like building our emergency fund which we ended up needing and kind of helping with the purchase of our short term rental, so I’m definitely grateful and thankful for the income that I was given from my W-2 because it did kind of give me that foundation. But one thing I want to touch on Ashley, because I think this is the part that doesn’t get enough, like doesn’t get talked about enough is that I was scared.

Ashley: Did Sarah quit her job already at this point or was she still working?

Tony: She was working a job that she wasn’t super happy with. She ended up leaving that job and she used to work in the entertainment industry. So, she went back to that job, working in the promotions department, and then COVID happened and then they shut down all of the promotions and marketing that she was doing. So, she was out of work as well, right? Because of COVID. So, neither one of us was working a W-2 job at that point in time. So, it was very scary for both of us to think like, “Oh man, we went from getting this really nice paycheck every two weeks, these big bonuses every quarter to now having nothing coming in at all. So, it was very scary, but I think what helped us get through it was A, that we had saved up a lot of money before and we knew that we had a long enough runway to at least make it through the year. And that’s kind of the conversation that her and I had, I was like, “Okay, let’s just give it 12 months. And if we can make it through the next 12 months and we feel good about where we’re at then okay, let’s just kind of keep rolling with this thing.” And we knew that we had enough savings to get us through the 12 months. The other thing is that we worked like crazy over those 12 months to really grow, right? It’s like we had three short-term rentals when I lost my job. And we’re at 12 right now within like 500 contracts. We’ve grown a lot in that 12 months as well. So, we had the financial cushion, we had the safety net, and then we worked really hard in the meantime to kind of bring everything together, but it was definitely a scary moment for us when it first happened.

Ashley: And I hear this a lot on personal finance podcasts and in books is that people who reach their financial independence and are living off their index funds or whatever, is that people always say to them, “Oh, what happens if the stock market crashes?” And their answers always, “Well, I’ll just be like everybody else. I’ll just go and get a job.”

Tony: Right.

Ashley: And they’re like, “If my worst case scenario is being like everybody else, I think I can live with that.” And that’s kind of the ultimatum you gave yourself is, “Okay, over the next 12 months, if I don’t make it work, well, then I have to go and get a job.” But you made it work and I am so proud of you and Sarah, like just watching you guys over the past year and all you guys have accomplished has just been amazing and I’m so proud of you guys.

Tony: No, and I appreciate that Ashley. And if there’s one final thing that I can share with people, I remember writing, like I would journal. And one of the things I would journal is part of like my goals. And this is when I was in college before I’d even got into the workforce, I would say my goal is that I want to be able to drop my son off at school and then pick him up in the afternoon. I specifically remember writing that down. And when I look up at the past year, it’s like, that’s literally the life that I’ve been able to live. It’s like I drop him off at school. I pick him up in the afternoon. I can take him to his basketball practices. I’m there for all this games. I can go to the gym in the middle of the day at 1:30 when nobody else is there. If I want to go on and take a trip, I don’t have to ask for PTO or worry about having to deal with all this stuff. When I was working on W-2, every Sunday night I would spend maybe two to three hours on my laptop just chugging through the emails that piled up during the week and just getting ready for Monday again. And I could just feel my energy dropping every Sunday night. But now it’s like literally every day to me feels like a Friday, maybe, right? It’s like that same feeling that you have on Friday when you worked your W-2 is how I feel every single day. And even though I’m not making nearly as much money as what I made when I was in my W-2, the freedom and the happiness that I feel is worth way more than that change in income. So, I feel so-

Ashley: Fulfilled.

Tony: … Definitely fulfilled, but even that moment of me getting fired, that could have been a terrible moment for so many people, but I feel so grateful that it’s become, I think one of the best things that could have happened to me, because it’s set me on this path to a life that’s the actual life that I’ve dreamt of for so many years. And it was that W-2 being taken away from me that forced me into this new life. So, I’m grateful for what felt like a setback in the moment. I’m grateful for it now, because I know is what I needed to kind of step into this life.

Ashley: Yeah. Tony, I’ll say it again, I’m so proud of you guys and what you guys have accomplished, and I’m so excited to see where you have become and that you don’t have to go back to work because, well, actually, because the reason I’m excited is because we don’t have to do 6:00 AM Zoom meetings anymore to accommodate your work schedule.

Tony: Yeah. So, what actually talking about when I was working on W-2 and we were doing the podcast, I would be up at like 5:30 Pacific time so I can knock out the interviews before I start at work. So, I’m also glad I don’t have to do that anymore either for sure.

Ashley: Yeah.

Tony: Yeah.

Ashley: Okay. Well, Tony, thank you so much for just being open and honest with everyone and kind of sharing that part of your story with us. And I hope that’s beneficial to a lot of people, not maybe somebody who did lose their job recently but also somebody who wants to leave their job, like what are the things to do to prepare, like, have that cushion have savings in place and have a business plan in place. You knew you were going after short term rentals, you knew your focus, you knew what you’re going to do. You had built your team. So, having those things ready before you actually do leave your job and then worse case scenario, you go back to working a job.

Tony: Yeah.

Ashley: Yeah. Well, thank you guys so much for listening. I’m Ashley at Wealth from Rentals and he’s Tony, @tonyjrobinson. And don’t forget if you guys want to sign up for the Real Estate Rookie Bootcamps, I am hosting how to get your first or next deal. And Tony is hosting a short term rental bootcamp. So, check them out on and we’ll see you guys on Wednesday.

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