Mike Simmons
Welcome to an exciting episode of The Underdog Show Podcast. In this episode, we delve into the world of entrepreneurship and real estate with Mike Simmons, a highly accomplished professional who has graced the stage alongside industry titans such as Gary Vaynerchuk, Ryan Serhant, Jocko Willink, Russell Brunson, Walter Bond, and Any Frisella. As the owner of a thriving real estate investing company and a partner in one of the nation’s leading real estate mentorship and mastermind organizations, Mike specializes in helping entrepreneurs create efficient systems, streamlined processes, and effective automation that enable them to work on their businesses rather than be enslaved by them. With a track record of empowering countless entrepreneurs to optimize and expand their ventures, don’t miss Mike’s insights.

In this episode, Pamela and Mike talked about how his success came to be. Some of the topics discussed are as follows:

  • What inspired Mike on his journey to where you are today? What are the culture and challenges instilled in his family growing up?
  • Why being an entrepreneur is not meant for everyone?
  • What are the drivers that pushed Mike to achieve success?
  • How did he get into real estate? What have become the challenges and lessons he learned? How did he get passed that?
  • The difference between flipping and wholesaling
  • Mike’s biggest piece of advice
  • Coming up in the next few months?

Listen to this exciting episode. Join us for the conversation! Listen to the full episode here:

If you found this story worth your time and made changes in your life, we’d love to hear from you! Subscribe and leave a review ⭐⭐⭐⭐⭐

Catch up with Mike Simmons here:

The Underdog Podcast host is none other than Pamela Bardhi. She’s rocking the Real Estate Realm and has dedicated her life as a Life Coach. She is also Forbes Real Estate Council. To know more about Pam, check out the following:

Want to elevate and protect your hard-earned assets and your family? Tune into our free masterclass on how to protect your assets: https://www.youtube.com/@elevatethroughrealestate


Click To Read The Transcript

Mike Simmons’ Inspirational Journey to Real Estate Success

Pamela Bardhi
Hello, everyone, and welcome to the underdog podcast. today I have an incredible guest here with me Mike. how are you, my friend?

Mike Simmons
I’m doing great. Thank you for asking. I appreciate it. It is we’re going into summer in Michigan where I live. And so the weather’s great. Trees are green. I’m loving it, I’m happy.

Pamela Bardhi
I’m loving that. And I was just complaining about Boston. because if you live in New England, you are always complaining about something weather wise. The fact that it’s winter in the mornings. then it turns into summer in the afternoons and then by the evening, it’s fall.

Mike Simmons
100% Well, we went from this is the worst I’ve ever seen in my Michigan. we went from 80 degrees one day, two days later, 40 degrees. That’s the biggest jump I’ve ever seen in my entire life. It was crazy. But so what happens when you’re in kind of the north part of the country, you get that?

Pamela Bardhi
Oh, my God, gotta love it. But hey, that’d be grateful for it somehow. Right?

Mike Simmons
Right, changing seasons leaves change. That’s beautiful. We don’t get that everywhere. So that’s good. Totally, totally.

Pamela Bardhi
Oh, my goodness, like, it is so incredible to have you on this podcast. As I was telling you before our column like, you’re just a rockstar, man. you’ve done so many incredible things work with so many different entrepreneurs and done so much in the real estate space. I’m super inspired to hear your journey and all of that. And I’m going to start off with my first question. because I almost want to know where it all originated. like what really inspired you on your journey to where you are today?

Mike Simmons
What inspired me um, well, I don’t know how far, far back I should go. But I was raised Midwest Michigan automotive family was in the automotive industry union. work nine to five mentality, get all the overtime, you can get mentality. The play, I always say the playbook that was handed to me. as a young man growing into an adult was get a job in a union company. work as many hours as they’ll let you work, retire at 65 or 70.

And then just sort of like live off the rest of your life like that. That was what everyone did. I saw there was nobody that was an entrepreneur anywhere in my universe. so it took me until my mid to late 30s. Before I even started thinking about is there anything else I could do? Because, wow, I hate my job. And wow, I’m not happy in this industry. I was in the automotive industry. it was awful is brutal.

And I was in my early to mid 30s When I started kind of questioning things. I thought at the time, I’ll have to invest my money. then the only way to invest your money at all is the stock market. so I’m going to look up how to buy and sell stocks. And it was like reading an encyclopaedia was so boring, or like a dictionary. I should say was so boring.

And I would get on like Google or Yahoo at the time and start searching. like through investing in stocks and real not real estate. but stocks and bonds and stuff. And it was horrible. And I would always end up somewhere else I would be on like ESPN or something. I would always like get out of there. so horrible. But if you scroll down on Google or whatever, investing far enough, you’ll hit real estate.

When I did, I was like, Oh, I know people do this, like no one ever told me this. And I started reading about how I could invest in real estate success stories. I became a success story junkie at the time just reading about other people’s success, right. And I made a decision in 2003 that I was going to be a real estate investor. Okay. The cautionary tale for everyone out there. a lot of people probably are in this boat.

I made the decision in 2003. But I didn’t actually buy my first property until 2008. So I spent five years in paralysis, analysis, self doubt, fear, all the things that keep people exactly where they are. even though they want something different. The people who don’t ever go anywhere else or do anything else or take that leap. It’s because they’re just they’re afraid.

And they’re just overloading themselves with information and making excuses. And I did that. But the difference is, I was raised by a Marine. My dad is a vet, Vietnam veteran. He’s a Marine, and he’s everything you think of when you think of a stereotypical Marine. No excuses, no mercy. You know, we all have it right. so what wasn’t allowed and we had all boys in my house.

So it was like testosterone city and it was just crazy. one thing that wasn’t tolerated was fear and procrastination. so I realized after five years of being an adult. and not being under his roof and wanting to do this real estate thing. that all I was doing was procrastinating because I was afraid. And I sort of hit emotional rock bottom.

I wasn’t like losing my house. I serve my family or anything crazy, I was making pretty good money. But I hit emotional rock bottom where I started feeling bad about myself. because I knew the only thing that was keeping me getting up. and going to a job in an industry I didn’t like, was fear. It’s like that it just felt bad. And I started feeling bad about myself.

And I just said, at one point, I would rather fail at real estate than continue to be afraid to try. so I took the leap, and we bought and my wife bought our first house to flip in 2008 and never looked back. I said, I tell people all the time. So what inspired me was your question. Honestly, the pain of my current situation was more. got to be more painful than the thought of failing at trying something else.

That was the inspiration. Like, I think sometimes people will run faster, to avoid pain. and work harder than they will to get pleasure. And the pain had just built up so much that I had to try something else. because even failure would be better than getting up and going into the same job again. But I told people when I did my first deal, I made money at the time. this is Michigan 2008, when everything had crashed, prices had dropped by 50 75%.

so I bought a house for $40,000. I put $15,000 of renovation into it. And I made $15,000. it was I had never seen $15,000 in one place ever in my life. It was like winning the lottery for me. And it was very much like if somebody hoped with somebody. would hold your head under the water for a long time. where you started panicking a little bit and you couldn’t breathe.

And then you came up for air, like taking that breath. how good that would feel and how you just feel like you almost died. but you made it like that’s how I felt after I did my first deal. I felt like I was literally taking the first gasp of ox of oxygen in my life. like I had just started my life like that day my life started. And I just feel like I wouldn’t be doing what I’m supposed to be doing. as opposed to following a playbook that was handed to me that I never asked for didn’t want. but didn’t have any other one, you know.

And so that gravitational pull of your family and friends and your environment. and how you grew up and what you were told. all of that stuff can hold you back. I always use that analogy, like I had to break out of my family’s gravitational pole. to do the normal thing to get outside of that gravitational pull to do what I want it to do. that’s an easy that pole is very strong.

There’s a lot of insecurities and conditioning and your parents typically not everyone. but most parents love their kids. And my parents loved me. They weren’t trying to like keep me back. They were trying to protect me by saying this is this. This is the safe route which we all know is not really that safe. This is what we all know is what we all do,this is what you need to do. They didn’t know anything else.

And so to encourage anything else would have been reckless for them. That would have seemed reckless for them. And the last thing was when I finally started real estate did my first house. I flipped houses on the side while I worked my day job for like four years. because of that conservative upbringing, my wife grew up very poor. She’s very fiscally conservative.

And for her like, hey, we flipped the house I made $15,000. Let’s quit my $80,000 year job and just do this. That wasn’t happening, right? So I had to work within what was real for my situation. I had kids and a house and all this right. So I did this for like four years on the side. And I made a tonne of mistakes. It took me a long time. But I finally got to the point where I thought I can make this work.

And I told my wife I said if I can save one year salary. put it in the bank, and we don’t touch it. we only use it if this isn’t working. if that is the case I’ll go back and get a job. but let’s just put one year salary aside. give me a runway of about eight or nine months. and then another three months to find a job if I have to. are you okay with that?

She goes if you can put that in the bank and yeah, for sure do it. So I did and like two or three months later. I had already gotten another year salary in the bank so it was game over at that point. But I don’t think it’s always necessary to burn the boats. and it’s sexy and glamorous to go out burn the boats and don’t give yourself a plan b.

Okay, let’s tap the brakes you might have a spouse who’s not as ambitious as you are. or not ambitious that’s wrong word risk of you know more risk averse the universe yep yeah. Or you know whatever you might have a situation. so let’s not like put your kids you know health in jeopardy. because you don’t have health insurance because can’t afford to like let’s not do all that. but it can be done right and so I just stopped making excuses and made it work.

Pamela Bardhi
I absolutely love that. My oh my god. So many things I want to flip back to because you made some really important things throughout. I’m like, hold on, it’s like a burst of the generational curses. because that’s exactly what you were talking about. and kind of unlearning all the things that you’ve learned. And that’s the thing is like most of us have been conditioned to this. like nine to five lifestyle.

and it’s not that our families are trying to hold us down or those around us, to try and elevate us. But like you said it’s because they’re trying to protect us. Yeah, at the end of the day, it’s not that they’re trying to play small. or anything like that this is just what they know. So in their world, this is their way of security.

So it’s like, how do you how did you break that? And for anybody who’s listening that like, maybe comes from that type of family. that’s really trying to do something different. and just can’t seem to like, move the needle. or maybe is just making having that realisation. of like, Hey, me, I feel like I’m supposed to do something else. Like, this is not for me.

Mike Simmons
Yeah, it’s tough. because it’s hard to, it’s hard to work within a culture that you weren’t raised in. if you want to put it that way, like the culture in my family was. it wasn’t a nine to five, that’s a banker mentality. Like my, my dad got up at, like five in the morning. sometimes three in the morning to go to work at four. and work until four, right, he was working 12 hour shifts a lot. And that was what he valued.

And that’s, frankly, what he respected. so that was what I was told I needed to do. but it’s not coincidental that I didn’t break out of all that until I was in my mid-30s. Because studies have shown that most people don’t really think of truly think about their retirement or ageing. Until somewhere in your 30s. you start thinking about that most people, some people are really smart, and they think about it early. And that’s great.

But the average human, in their 30s, somewhere starts thinking about how do I retire? Am I going to be able to and that’s what I did. so I started just extrapolating what I was making cost of living raises. you know, all that crap in the corporate world. And I was like, I’m never really going to be able to retire and have the life that I want. And do I really want this I started questioning things.

And I’ll be honest, like, I didn’t go to college right after high school. because I got in with a union company, right after high school. And I thought I didn’t love high school. Like most kids don’t love high school. I was like, Why do I need College? I’m in a union job. I was told if I got into a good union job that paid well, that’s the goal.

so why am I gonna go to college and I took a couple of classes community college. and just said, I’m out like, I’m doing this, that’s where I’m gonna be the rest of my life. Well, fast forward, it was ups that I was working for, at the time. wrecked my back at a early 20s, wrecked my back couldn’t stay there.

And so at some point in my late 20s, early 30s. I thought I’m really a commodity in the working world. like, I wouldn’t even hire me, I don’t have a college education. I have very little experience, I had to change industries. because I hurt myself, like, I needed to do something. And so I went back to school, went back to college, got my degree. I’m not a huge pusher, for people to always go to college. it’s not always the solution, especially in the world we live in now.

It’s way less important in 2023, as we’re recording this than it was in 1990, or 9095. And so, what it did, is, I had a singular path in my brain of what I needed to do in my life. or should be doing or was supposed to do. College did open up something in my head that allowed me to think differently. to think bigger, and to because my parents loved me. but they never said, What do you want to do? What do you like?

What kind of a life do you want? When you’re an adult? None of that stuff. It was like union job go. Well, college, you start dealing with people who have all kinds of different ideas of what they want to do. And I was a business major. so there were like finance people and people who are more entrepreneuria. and I got to know them. It unlocked something in my head that was like I was in this closet. Not in the closet, but I was in this closet.

And I could only see the walls that were right in front of me. then college just opened the door to like the rest of the world. And I was like, Holy crap. I don’t go to MIT, I don’t have to do this. Like there’s other things out there. that was the first step. then a few years later, is when I found real estate and I was like. This is what I want to do. so for me College, the cost of college was not the degree. It was the mind expansion that I went through.

And some people don’t need that because they have families that are real, like, progressive. like, Hey, you can be an entrepreneur, I can do anything you want to do. That wasn’t my family. My family told me what I should do and that was right. So college was on my mind expand For me. and it made all the difference in the world. But really, I feel like I was an I was this sounds cliche. but I was an entrepreneur trapped in a nine-to-five union job.

I wasn’t a good employee, I had my own opinions about how we should do things. My bosses never really loved me, because I was questioning everything that they were doing. and thinking that I had a better way. Like I was, I was like a lone wolf that was being forced to be in a pack. and I just didn’t work well in a pack. So I was sort of, I think I’m predisposed.

I my risk tolerance is off the charts. like I will, nothing scares me financially when it comes to that. And so I was not really where I needed to be. And the minute that I found the minute that I was put in the environment. that I was supposed to be in, it all felt normal, like I felt completely at peace. where I was, and I loved it. So I think sometimes, you have to try, you have to just do it. It’s not for everybody, I have three kids.

Two of them are not entrepreneurs, and nor should they be. it’s not what makes they would be stressed and unhappy if they were an entrepreneur. One of them is an entrepreneur, her and I do deals together. we just started working together in real estate. She’s awesome. And so my other kids, but they’re just not entrepreneurs. they need to be in a job with structure. It’s fine. Nothing wrong with that. I’m just not a structure person at all.

Pamela Bardhi
Neither am I, to check on that one like to say, I love that. Thank you for so much for explaining that. Because I mean, like, it’s just it’s so different for everybody. like you’re seeing so many people come out of their shells. And you said something really important that not everybody’s meant to be an entrepreneur.

it’s just a matter of like, where do you fit in and understanding what that looks like for you? Yeah, like you said some people’s they burned the boats and gonna quit their job and do it. And I’m the same as you. I’m like Columbo back it up a little bit. You know, like, I started in development when I was 21. I had backups, right? Like, if I really effed up heavy.

I still could go to my parents in law and make up for myself there. But like, as you get older, you got responsibilities. you have kids, you have all these things. like you really got to be strategic on how you do it. So I love that you maintain your business on the side for four years. and then kind of went from there.

And after being in this for five years of analysis paralysis. I know so many people that are in analysis, paralysis mode, right now. a lot of people are scared of what’s coming in the market. I mean, because we’ve got 3 trillion in commercial assets coming due in the next 18 months.

You know, like lose digital currency that’s launching. there’s a whole bunch of stuff that’s launching. pretty soon that’s gonna affect rates again. it’s like dealing with interest rates. And then now on top of that, just a whole slew of so many different things new.

Mike Simmons
I’ve never heard anybody say ever in my business life like since I’ve been entrepreneur. I’ve never talked to another entrepreneur who said. Boy, am I glad I waited 10 years to get started. Nobody has ever said that. Right? And so I get it. There’s things happening in the market. But right now is the best time to get started in real estate.

It just is and then in 10 years, you’re not going to look back. and go I wish I wouldn’t have started early. I wish I would have waited nobody wishes they would have waited I waited till I was in my mid to late 30s. Oh my gosh, I wish I would have started 15 years earlier that would have been awesome.

I would have been 15 years farther than I am now. That’s awesome. People always regret waiting they never regret getting started. That’s my experience. They just do

Pamela Bardhi
Yeah. And it was the same thing. I’m still mad at myself for being in high school in 2009 and not buying real estate

Mike Simmons
it’s funny I calculated one time I gave a presentation on like what I wish I would have known. when I could tell my younger self kind of a presentation. And so I went back and did an exercise and said okay, if I had actually started investing in 2003. When I said I wanted to with the learning curve applied.

nobody starts and just starts making tonnes of money overnight. you learn you make mistakes, even applying a reasonable learning curve. The years that I lost, I calculated in real like actual calculation actual money. I lost $3.1 million in those years that I waited it. so there is a price, there is an opportunity cost that you think you’re being safe.

and not taking the risks, you know what you’re doing. you’re losing money because had you gotten started. got over the learning curve made your mistakes. you would have already been making money if you’d started 10 years ago or five years ago. or whatever it is that people are listening is going I wish I would have started.

There’s real money there’s an opportunity that you’re missing. is passing you by and the worst thing, what’s worse than failure is regret. so you get to the end your life and you’re God willing your 9095. whatever it is when you finally on your deathbed. regret is so final. There’s no way to fix regret it when you’re that age.

It’s over. It’s done. You’ve done it against over failure. You can rebound from failure, you can fix failure, you can go back and do it better. The next time failure is temporary. Regret is totally final. And that scares me. Like maybe this isn’t like the way that you should tell people. or the way you know, it’s not the way people talk about a lot.

I’m driven more by frustration and fear than I am the desire to be financially free. I love it. But fear and frustration drives me more. And so you know, I hear this a lot people ask. Why does Elon Musk still work? Why in the world? Is this guy starting new things? He’s a billionaire, multibillionaire, probably going to be a trillionaire.

Someday, why does he keep working so hard? I found and I’ve talked to a lot of folks like this myself, who are very successful. Most successful people have some level and something in their head. or something that says this could all go away. Because a lot of people, especially people who didn’t weren’t born rich. they remember struggle.

And then there always were, I was listening to a podcast. literally before we started talking about this guy who sold his company for $300 million. And he’s afraid every day that it’s just gonna go away. so maybe that’s not healthy. But a lot of successful people are driven by insecurities, frustration, fear, all this stuff. Trying to prove somebody wrong, like trying to prove your doubters wrong is a negative emotion.

But how many people are driven by trying to prove people wrong. that they are not a failure, that they’re not stupid, that they’re not? Whatever? that’s a big driver, right? Why do boxers who are super great at what they do. most of them come from an environment where they had to fight to live. and then they win the title, they’re millionaires. the matches are further and further apart.

And they end up losing a title because they’re just not hungry anymore. They don’t they don’t have, that fear of not being able to pay their bills. And I think entrepreneurs are that way too. We have to have some level of doubt about what the future holds. for us to sometimes drive us so we don’t get complacent.

Pamela Bardhi
Hell yeah. And I say that all the time. Literally the regret is far worse than fear.

Mike Simmons
Way worse. Experience,

Pamela Bardhi
fear of failure, meaning it’s like, Would you rather be on your deathbed. and say to yourself, shit, I wish I did this? Or actually do it, you know? Or I’d say, hey, you know what, I didn’t do so well at this. But it led me into this path and this path like it’s a whole absolute. I’m you’re preaching to the choir when it comes to that.

1,000% like, and I love that’s a great way and great perspective to look at it. because it’s like what, really do you have to lose by just trying. okay, if it goes sideways, do someone else like, okay, like no biggie. No biggie. And I’d love to dive into your story to get when you did decide to go all in into real estate. because you’ve built some empire. So I can’t wait to hear all about that. And all the awesomeness. Yeah, how that was all created.

Mike Simmons
Yep. So we started my wife and I started off doing this as a team flipping houses. you know, watching all the flipping shows on HGTV, We did that together. I mean, there’s a lot we could talk about here. But I’ll kind of give you the highlights. We started having success pretty quick. You know, in our market in our local market. we were one of the more known flippers, and we were growing which was great.

And I started to think that I’m almost, I got so much confidence. that I thought I could literally do anything and be successful at this point. I’m just got the Midas touch. Like, in my brain, I was thinking this is easy. And I could literally do anything, I think and it’d be fine. so I got out of real estate a little bit. I started a tangential business. It was like adult foster care facilities. I took on a partner.

And my role was to find properties, get them set up for like adult foster care guidelines. Got I think handrails and all the you know, handicapped stuff. And his job my partner’s job was to bring in the clients like bring in the people. who are going to live there that needed this adult foster care. long story short, those are, it’s a great business.

But it’s a business that’s feast or famine. You’re either making a tonne of money or you’re losing a tonne of money. It’s almost no in between. And we started off making money very quickly lost our residence. we started haemorrhaging money. And we had to dissolve the partnership and it was like a mess. I end up losing $30,000 on that whole adventure. it was only like a six month long adventure.

I lost 30 grand and my wife was like, Alright, we’ve got to just stop for six months. Can we just take a break on all of this? Like, can we just go back to like not taking credit because again, risk averse. She’s like, this is too much. I’m stressed out. I said, I agreed, of course because it wasn’t really a question. It was more like we’re gonna stop for six months.

And so we stopped. six months later, I was like, let’s go we got to do something. I want to get back into real estate, I know that I did it. I’m good. Read it. And she’s like, You know what at the time she was a teacher. He’s like, You know what? You do that I don’t want to it’s too stressful for me. This world isn’t good. It’s not good for me.

It’s not healthy. I’m very stressed out all the time. You love it, you’re good at it. I believe in you. I’m gonna be your biggest cheerleader, I support you 100%. I just don’t want to be involved in it. Like, you can keep the day-to-day stress to yourself. and just come home and we don’t have to talk about it. So I did that.

And it was like she was like the restrictor plate in my race car. I was trying to push the gas. she was always trying to pull back a little bit like slow down, we’re going too fast. When she stepped out of the business, it was all gas, no break. Like I went fast, And I started growing fast. I started taking bigger, not risks. But you know, I was being more aggressive with my deals. taking on more than I took out in the past.

And we started growing, and I was flipping houses great. I quit my job. then I hit a point I was doing a lot wrong. But like, in hindsight, I was doing a lot wrong. I thought I was doing it. All right, two mistakes that I made. this is just maybe good information for your listeners. Two biggest mistakes I made while I was flipping is I only had one contractor. one on all my deals one person who was my single point of failure.

And I only had one realtor that I was working with, which is fine. But I was giving that realtor too much power in my business. meaning he was running all my comps, I had no idea how to determine after-repair value. I was just getting houses and turning them and letting him Tell me, what should you buy it for? And what should you sell it for? It’s too much power for someone who doesn’t really work for me.

And so we got to deal under contract. It was in his hometown, by the way. it was in his neighbourhood almost where he lived. He told me the prices totally believed them. Put my contractor on it. We started working. Throughout the process, my contractor started not showing up. He started trying to upcharge me for things he started. trying to add things on that he wasn’t doing.

like contractors things sometimes are good at shooting themselves in the foot when they have a good thing. They’ll screw it up no matter what. He just got to the point where I don’t know what was going on his life. But he was lying to me. He wasn’t showing up all this stuff. We got through the project anyway. I decided I’m not gonna use him anymore. Like I’m gonna have to find a new contractor. because I’m not putting up with lies and all this stuff.

Well, we put the house on the market. Crickets didn’t sell didn’t sell didn’t sell we lower the price lower to lower. It didn’t sell this. I’m like, dude, what’s going on to my realtor? This is your neighbourhood. You know, you’ve lived here for years. Why? And he like yeah reran the numbers. He’s like, we’re, we’re way too high. We’re way too high. I’m like, This is what we need to be at. Otherwise, we’re going to lose money. because I bought it based on the after repair value. You gave me both prices. You know, I’m going to lose money on this.

His response was you win some you lose some. And I was like, Oh, hell no, we don’t lose any not like this now with that attitude. so I found myself getting rid of my realtor. who was a lot of my brain of my business. And I got rid of my contractor who was my only contractor. Meanwhile, I’m still getting deals coming to me and opportunities. I got a deal that I went looked at it signed a contract. I was like, I don’t have a realtor, I don’t have a contractor.

I don’t know what to do here, I don’t really have the ability to move forward on this. But I signed the contract because it was a good deal. So I called one of my friends that was a house flipper. And I’m like, dude, here’s my situation. I just had to give it to my realtor, I don’t have a contractor like I can’t do this one. But I know you’re looking for deals. I didn’t tell him the price I paid but I gave him a price.

I said would you pay 110 At the time that was with house. That was a good purchase price for the house. I said well, would you be interested in 110 $110,000. He goes give me 10 minutes, call me back in 10 minutes. He goes, that’s a good deal. I’ll take that, I entered the contract for 95. When to closing wholesaled. My first deal didn’t even know what wholesaling was, I just put myself in the middle of it.

And I got it under contract for 95. I sold it for 110. I cobbled together an assignment contract, which I didn’t even know what they were. we did it. And I was like 15 grand, I probably would have only made 20. maybe, maybe 20, maybe 25, probably 20. I was like that was the easiest money I’ve ever made my life. It took me a day. by the time to really realise the money, like two weeks does nothing.

Got another house under contract, literally the same price in the same neighbourhood nine $5,000. I called the same guy and said, Hey, I got another one. Do you want to look at it, He goes Tell me about it. told me about it. I said how’s 110 He goes, I’ll take it. He didn’t even take 10 minutes. He goes I’ll take it because he knew the neighbourhood now. I made another $15,000 in one month. I made 30 grand or two houses that I never looked at hardly never touched. never did anything.

And I was like, whoa, whoa. Now, one thing you have to know about me is through building my businesses and hiring people. And in going through all that, I learned about personality assessments. The disc, the Colby, all these all these assessments of people take well. I took them all because I’m gonna use these to hire. I want to know a little bit about me, what does it say about me?

And to me it was like a little bit like a fortune teller at the time. I was like, How accurate are these things started taking them and they were like really nailing me. But one thing I learned over the last several years, is among other things, I’m incredibly impatient. I like things to move fast, I have no tolerance for things going slow. And so I made this money, boom, boom, 15 grand and two deals.

And I was like, this is a great thing has ever happened. I’ve never felt more alive in my life. Like this is awesome. And so but I didn’t know much about wholesaling. So I found a wholesaler in my market who I was sort of an acquaintance with. it wasn’t really a friend to somebody I knew, took them out to dinner. just extracted everything from him I could everything he knew about wholesaling.

The next day I said I’m wholesaling. And I’ve been primarily wholesaling ever since I love it. We do about 100 deals a year. I love the velocity of wholesaling. I love that I find an opportunity, get it under contract. find a buyer go to closing two, three weeks later, I got the money in my account. Boy, I like that because what I didn’t like about flipping and flipping is great. By the way, my daughter flipped houses for a while I helped her that was what was right for her.

But I didn’t like appraisers. I didn’t love mortgage companies like end buyers. it was just all a hassle, I couldn’t control it, it was all out of my control. And in one of the defining moments that made me really not love it is. And we’ve all had this, especially if you are flipping in the 2008 to 2012 timeframe. People appraisers got real gun shy. because there was so much shady stuff going on prior to 2008.

And these appraisers got real slapped down really hard. And banks got a lot more scrutiny about how they were picking their appraisers. it couldn’t be this good old boy network anymore. so appraisers started erring on the side of caution sometimes to a fault. so I enterpriser come in my house and I had comps all day long.

Like it was legitimately worth I think this particular house was like literally with the sale price should about 180. And that was a very objective, very fair number. And he came in at like 160. I was like, dude, with a wave of a pen. You just cost me $20,000. Like what? Like this is insane that you can’t tell me that this house isn’t worth 180. I’ve got comps that show it all day long. It’s very, as clear as it can be.

And he’s like 160, I was like, Oh, this This isn’t right. Like I’m in a business where somebody else has control over 50 to 75% my profit and I’m in Michigan. I’m not selling million dollar houses, I’m selling houses that are in the 150 to 250 range. You take $20,000 out of my profits, you’ve taken half or more of my profits. I’m probably gonna make 25 or 30 on that. And I was like, this is out of my control. This is not good.

when I started wholesaling, I eliminated most of the people who could have a negative significant impact on my company. And it became more about what I could do the deals. that I could find how can I negotiate with the seller? And how can I negotiate with the buyers like that is way more under my control. so I’ve been doing a lot of that.

And by the way, my business took off. I was doing like I think I was doing 10 deals a year flipping houses. And then I started wholesaling. Within a year and a half, I was doing 10 to 12 wholesale deals a month. like just took off because I loved it, I was so much better suited for that. that’s something people to think about if you want to flip houses. but you hate managing contractors and all that kind of stuff.

Like it may not be the best route, you might want to do something different. because you will be managing contractors and contractors oftentimes are hard to manage. It’s like corralling cats, right? Cats with personal problems, really, you know? So, if you don’t love that, you gotta really gotta do what you love. and kind of go in a direction that makes sense for you. Oh, totally,

Pamela Bardhi
totally. Mike. I love that. And I love that you took like the wholesaling route. it was kind of the same thing that happened with me. it’s like I was flipping and then you know, love that game. But then I was like, looking at the inefficiencies of my business. I’m like, I can only do so you can only do so much.

You know what I mean? Like with construction, because there’s so many moving pieces to it. Like you said, a lot of stuff that’s out of your control. And flipping is amazing. But you’re limited right so like when it comes to wholesaling. I mean, like it’s pretty much limitless and you’re putting deals together. and like you’re putting all that together and it’s exciting.

And you don’t have that those types of headaches. I know I get this question all the time when it comes to wholesaling. I’d love your input here. but like what are some of the biggest myths that you can bust on wholesaling? And like what are some of the most efficient strategies for someone who’s looking to get into that? Because most people come to me I’m like, Man, I want to learn how to wholesale.

And I’m like, Great, I’m not your person. I know people that are super good at that. like I know how to put deals together but here in mass there’s not really too much wholesalers. because it’s such a heavy like attorney state. And it’s also a lot of agents here a lot of real estate agents.

so it’s very hard to like it’s very difficult wholesaling market. So that’s why I’m not like too too keen on all the all the details. I’d love your input on those because I’m sure it’s an add a tonne of value to people listening. because that’s the number one thing I hear it’s like, Alright. I want to get into wholesaling when they think about real estate,

Mike Simmons
I’m hyper competitive. So when you tell me there’s not all wholesalers and mass. my brain says, Oh, no competition, I need to go there. That’s where I need to do this. But to answer your question, what are the myths? There’s two big ones. One is that wholesaling is illegal. It is not, right. There could be regulations in your city, and maybe there’s certain circumstances. but as a general statement, it’s not illegal.

Okay, that’s number one. Number two, is I’ve been a house flipper at some scale. I have some experience with it like more than most people. And I’ve done wholesaling at scale. The wholesaling business building a host. a successful wholesaling business is harder than a house flipping business. I’ve done both proof of that, or how can I justify that? My daughter came to me, like I told you, she flipped houses for a while.

She came to me when she was 22. Maybe. And she’s like, Dad, I want to do something in real estate. I don’t know what do you think at the time. still, she’s a social worker, she went to school for it, she loves it. It’s what she’s passionate about. She never wants to stop. She was not looking to get out of her business. She’s entrepreneurial, like I said, so she’s always thinking. How do I do more? How do I maximise my time? How do I create income?

So she came to me said, I want to do something in real estate. I’m wide open to whatever you think are what we kind of come to? And I said, Well, do you want to quit your job? No. Okay, how much time do you have available? Some but not a tonne, I can’t be somewhere every day. And so we started going through and I said. I think you need to be a house flipper.

There’s a lot, there’s a moving parts in the house flipping world. But most people I know who are doing house flipping well. they’re not swinging a hammer themselves as the owner of the company. They’re hiring it out. either subbing out themselves, or they’re hiring a general contractor. So I said, what I think you should do is flip houses. I’m a wholesaler, and there’s other wholesalers in the market.

By the way, get in all of our lists, like you should be looking into all of our deals. making offers like crazy, when you find one. we’ll raise the money through hard money, or whatever we have to do. we’ll get you the money. And I’ll help you hire a general contractor. And a general contractor is going to be spinning most of the plates.

They’re hiring the subs, they’re making sure schedules are being met. And you have one point of contact generally, in that your general contractor. He’s honestly doing most of the work. most of the moving parts are handled by him or her right, wherever that is. And so we did that again. sometimes when you don’t know where the dangers are. or what to be nervous about, or how hard things can be.

Sometimes naive people are the most successful. She just saw me. Like, I started becoming successful in real estate. as she was coming online with like, what’s my dad do? Where is he right now? Like, so her experience of real estate is my dad’s a real estate investor. And we’re doing well, right like it works. It’s easy. You know, he’s doing it must be easy.

So she started making offers, like I told her. I said, you make offers you go on these wholesalers list. make offers on everything, just start making offers. She got three houses under contract in the first three weeks and flipped them. and made over $60,000 Within the first six months.

Like she just didn’t know, like I work with people, I coach people on real estate. how to build companies how to build a husband company, wholesaling company, whatever. And I always get loads, no deals, and no one will take my offers. And I don’t know what I like do my 22 year old daughter. who had never done real estate. she didn’t like she wasn’t a kid that grew up going on job sites with me at all.

She didn’t know anything about real estate. She just didn’t know to complain and have negative attitudes about it. Well, this is what my dad said to do. He seems to know I’m just gonna do it. He said, right. How many times have you work with somebody. and it’s like they they’re their own worst enemy? Because they question everything.

They doubt everything before they even try it. You get someone who just says well, if you say to do it. I’m just gonna do exactly what you said. And they just execute. They almost always win because that’s that’s what winning is executing. And she just executed and she won. So, you know, the biggest myth is that it’s illegal. Second biggest one is it’s a beginner’s move. Like if you go online, bigger pockets or whatever.

Most people will tell you common wisdom is you want to get into real estate. you want to flip houses or you want to be in multifamily. Here’s what you do. start off as a wholesaler, because you don’t need any money. You don’t need any experience. It’s super easy. Do wholesaling for a while then start flipping. And then when you want to move into the big leagues go to multifamily, right, that’s fine. The problem is there’s a lot of bad wholesalers.

And it’s because they think they need no money and no experience. What made me succeed as a wholesaler fast was I flipped first. So I had private lenders, and I had money waiting for me to need it. And I had been flipping for at that point. when I switched somewhere around five years I’ve been I was flipping houses. so when I got to be a wholesaler, I could look at a deal. exactly the way a house flipper will look at it.

And so I knew what they would pay what a house flipper would pay, I would price it accordingly. I could run rent or I could do a renovation budget. I knew when I walked around the house. what it was going to cost to flip it. so I could put together the budget and everything. so that I knew exactly what a house flipper would pay. And that gave me a strategic advantage.

Most wholesalers don’t have any experience, they don’t know what they have. And so they put out a deal to their buyers, it’s always way too high, or way too low. because they’re just guessing they’re just throwing darts I have no idea. house flipping is an easier if you work a full time job. You don’t have tonnes of time and tonnes of experience. I believe you can launch a house-flipping business easier and faster than you can a wholesaling business.

I don’t think my daughter would have been successful had she tried to be a wholesaler. she didn’t have the time. And so wholesaling has moving parts. Flipping has moving parts, but moving parts in a flipping business can be handled by a general contractor. The moving parts of the wholesaling company can not be just contracted out. It’s in your company, its marketing, its sales.

It’s a transaction court, like all that stuff has to happen inside your company. Somebody has to answer calls, somebody has to talk to sellers. somebody has to talk to buyers, it’s much more active. In my opinion, in my experience than flipping. you can outsource a lot of flipping, can outsource a lot of wholesaling. Now, that being said, wholesaling is very active.

I’m talking to you right now, it’s currently for both of us 2:50pm. haven’t been in my business all day. haven’t been in my business all week. like I have people who work for me, I have acquisitions, people, I have marketing people. I have people who talk to our buyers, I have transaction coordinators, I have a bookkeeper. Like I don’t buy houses, I don’t sell houses, I don’t even know most of the houses that we have. I don’t see them, I don’t talk about them.

Because I run a business, right. I’m not a one man band I have built a company that runs in my absence. and produces seven figures, every in profits every single year. I average two hours a week in my company. And an hour of that is a meeting that we have once a week. the rest of the week, maybe an hour. And that’s just miscellaneous stuff that you have to do as an owner. but very little do I do in my business and approves the seven figures. I can talk to you in the middle of the day.

Mike Simmons Biggest Piece of Advice

Pamela Bardhi
That’s amazing, Mike, that’s amazing. My goodness, thank you so much for breaking that down. And because there’s so many myths about wholesaling. you just discussed how you took your company to basically the pinnacle of what every entrepreneur is trying to achieve. which is the delegation, piece of and systems and processes and people. Now what would be your biggest piece of advice? Would you say to somebody who’s interested in building a business in wholesaling. or just in real estate in general?

Mike Simmons
The biggest thing is, stop talking about it. Stop making excuses, stop thinking about it, just freakin do it, like start doing it right. And then before you think you’re ready, you need to start assembling a team. biggest mistake that I made before my company kind of took off is I had this limiting belief. that I needed to be a big company before I could hire anybody.

But I couldn’t really become a big company. Until I started hiring people, right? I couldn’t do it all myself, you can stay small. it’s fine that not everybody wants to be a company. And I’m not saying when I say big in a real estate, single family world. big as you know, four or five, six people in your company. I’m not talking about 100 people but to go beyond a one person operation. It unless put it this way.

If you don’t care to work 1012 hours a day, great be a one-person operation. you still may not get to seven figures because you just run out of bandwidth. No matter how optimised you are. You’ll run out of band-aid there’s too much happening in any business that gets to them that level. So if you want to run a seven-figure, business and beyond don’t wait until there’s an avalanche of work. that you’re not getting done.

and things are slipping through the cracks and you’re missing on deals. Like that’s too too late. You should have already hired Somebody. So start thinking about putting together your team sooner than later. Even if it’s just a part time admin, who kind of helps you stay organised. make sure that you’re catching emails. make sure that you know you’re not missing anything. like a part time admin from the Philippines is not expensive, right?

That’s a good first start. And when you see how fantastic it is to take things off your plate that just take time. but they’re not high value stuff. You’ll understand the power because before I did my own. Well, I was my own company. I was the whole company. So I was doing sales in my company. I am not a salesperson. That’s not really my skill set. But I was getting deals.

And I thought, I’m okay, I’m not I knew it wasn’t my best thing. But I’m okay. Well, when I hired a salesperson. the first time I heard an actual, like, legit salesperson. I went from doing at the time I hired him, I was doing one, maybe two deals a month, I hired him. And with the same opportunities of appointments, the same everything. I went from doing one to two deals a month to doing three to four deals a month.

Now, that’s tremendously different, that your company has a different company. when you’re doing four deals, as opposed to one. And so I was like, for the first time I was like, Holy crap. That’s the difference between me and an actual person who loves that. And so you start putting assembling people in your company. who are better at that singular thing than you are or as good or can be as good.

Like, that’s a game changer. So people are how you grow, you know, you can have all the systems you want. But if your bandwidth is being exceeded, a system isn’t always a systems. and processes will optimise you write. And so you’ll go from being able to do X to doing x plus one. but you’re never going to do X times 10 by yourself, never.

You have to bring people at your company. And so growing your team and putting rockstars in place. far and away the biggest lever you can pull to grow your company. and to grow it without running yourself to death. I

Pamela Bardhi
I absolutely love that, Mike. because everyone’s just like so scared. See, that was a great tip that you mentioned in there. there’s virtual assistants that you can get for the time being. and then just, you know, grow organically from there. I’m sure that’s exactly what you did it. to get to the point that like, two hours a week, right? You even beat the four hour workweek like by half. Like that’s efficiency right there. I love it.

Mike Simmons
Yeah, I mean, listen, I run more than one business. So I can’t be in my real estate business all day, if I want to do what I’m doing. I have a lending company, I have a podcast, and things that I do. So but yeah, you could totally do it, I probably don’t even need to be in two hours. But I just feel like there’s a level of responsibility and negligence that comes with not even showing up. you know that that’s a recipe for disaster.

So I’m just there to keep my hand on the wheel a little bit. And until, you know, full transparency, I have a partner in that business. so I put two hours in, he puts in a couple hours. Like, it’s great, right? And so partners can be great too. It’s a whole different podcast, maybe a whole different conversation. But partnering is, is very powerful. I’ve seen it go wrong a lot, right.

so there’s a lot to consider when you’re going to partner with somebody. but it does allow me to maybe I’d have to put four or five hours in. if it was just me in the company. But I got a partner. So you know, and I did that on purpose. I wanted to spend behalf I wanted to have Time. My Time back and I’m willing to part with some profits.

to give myself more time because trust me, if you’re listening to this. and you’re 21 years old, you’re like, come on, Grandpa, time doesn’t matter. I got all the time in the world. You get to be a certain age, maybe that’s late 20s 30s 40s 50s. whatever it is, at some point, money and time are going to flip flop and you’re how you value things. And you’ll start valuing your time more than money. I promise you it’ll happen.

Pamela Bardhi
Absolutely, absolutely. I love that. Mike, thank you so much for sharing that. And now like what’s going on in your world. you’re mentioning you have all these different companies and all these incredible things going on. like what’s up in your world and like the next six months, or even like the next two or three?

Mike Simmons
Yeah, thanks for asking. So, you know, like you, I’ve had personal success. It’s been great. And I enjoy it very much. It allows me to spend time my family and I love that. I started a podcast years ago because I wanted to be helpful to people. I’m an introvert by honestly, by the way. so if I go to a party, you invite me to your house with 10 other people. I’m gonna be sitting in the corner not talking to anybody. because I’m just not good in that environment.

And so I would go to meetups and RIAs as a new investor, and I wouldn’t ask questions. I wouldn’t raise my hand I wouldn’t socialize because I’m just that that person. And so I started a podcast to try To help people who also wanted help. but they just didn’t know or couldn’t go get it because whatever introverted or whatever it is, I have. So one thing we didn’t talk about.

And I won’t make a big thing here, but just so people understand. Other than hiring, the one thing that made all the difference in my world of going. from, you know, a couple of deals a month, to like, 10 1215. I’ve done 25 deals in a month. The real catalyst for that was, I got coaching. I started seeking out people that were significantly farther down the road than me not just a step farther.

And that was how I learned to hire by the way. So the coaching came before the hiring. the person that I was that was coaching me says like, Dude, you need to hire. So that was huge for me. And so I worked within this coaching programme for years. I helped hundreds of investors inside of this coaching programme. but it’s expensive. When I started, I hired this programme for $25,000 a year, per year.

And it’s a lot of money. And so I thought, I’ve been helping people inside of this environment for a long time. There’s a lot of people out there that can’t afford 25,000. I get that, right. It’s not for everybody. so the beginning of this year. I made a goal to help 100 people reach their goals. and started my own coaching mentoring programme.

And so I’ve been doing that that’s what I’m really spending most of it. Yeah, what are you doing for the rest of the week. you work two hours in your business? What do you do, man? So I’m mostly working with other people in their businesses. That’s how I’m spending a lot of my time. so that’s something that’s really important to me. And I wrote a book a couple of years ago that if you’re cool with it. I’d like to offer a digital download version of the entire book to your folks.

So if they go to my website, Mike simmons.com, forward slash underdog. they will there’ll be a special page for them where they can just download the book. the book, I wrote it, because I would give presentations. And I always have this chart that I put up of my company trajectory. it’s sort of flat, like it’s a little bit of growth kind of flat. And then it just hockey sticks at some point.

so people always ask, what, how did a hockey stick like. this is fine back here when you were struggling? But what happened right here when you hockey stick. like what made the difference? And so I answered this question so often because of that slide. I said I’m just gonna write a book about exactly. So the book isn’t designed for like, how do I get my first deal? That’s not this.

This book is I’m doing deals, but I’m sort of hitting this glass ceiling. I don’t know how to take it from the side hustle. I don’t know how to make it a full-fledged business. How do I make it a full fledge actual business? That’s what the book is. It’s called level jumping. And the reason I called it. that is because a lot of people say I want to take you to the next level. Well, I don’t want to take you to the next level. I want to take you to the next next level, right.

So we’re level jumping in this book. we’re just we’re I’m letting you skip a lot of learning. and go straight to being profitable and running a successful company. So that’s what the book is about. And you can get that for free. If you go to Mike simmons.com. Forward slash underdog. It’s yours.

Pamela Bardhi
Amazing, Mike, thank you so much for dropping that link. And for offering that to the audience. I’m sure they’re gonna find a tonne of value here. Thank you so much for that. And for anyone who wants to reach you and your awesomeness, where can they find you?

Mike Simmons
Um, you can reach out I’m on Facebook, I spent a lot of time there. I don’t go into a lot of social media stuff, but I am on Facebook. And if you go, you can find me at just our real estate.com That’s my podcast. I also have a page on Facebook. you can go there and you can reach out to me. you can email me at Mike at just art realestate.com Whatever you want to do. There. If you grab the book and you’re on my website. you can contact me through the website if you want as well.

Pamela Bardhi
You are amazing. Mike, thank you so much for being here today. Total Rockstar. Thank you for the inspiration. You are amazing. I appreciate it. That’s nice of you. Thank you.

Tune in to the episode to hear the rest of my incredible interview with Mike Simmons. If you found this story worth your time and made changes in your life, we’d love to hear from you! Subscribe and leave a review. The Underdog Podcast host is none other than Pamela Bardhi. She’s rocking the Real Estate Realm and has dedicated her life as a Life Coach. She is also Forbes Real Estate Council. To know more about Pam, check out the following:

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