Healthy Self
June 3, 2022

Business Coaching That Changes Lives

Entrepreneur and business coach Steve Cavanaugh shares how he attends to both business and human needs through his Master Mission trips.

Entrepreneur & Business Coach Steve Cavanaugh has taken great joy in helping many people start and scale large businesses. But Steve has taken even greater joy in helping to change people's personal lives. Steve states that many times, business challenges are really rooted in life challenges. Steve has created a unique group coaching called Master Mission. These Master Mission trips have allowed many people to slow down and reflect, as Steve helps each person navigate through the messiness and come to places of healing. He helps people learn how to break down facades, so they can get down to dealing with life challenges. Steve loves coaching and attending to both human and business needs. Through these Master Mission trips, many people's lives have been changed for the better. And Steve has helped equip entrepreneurs to affect future generations internally and externally. Steve shares that in order to go further, you actually need to slow down.


Business Coaching That Changes Lives

We have got a great guest with us. His name is Steve Cavanaugh. He lives in the great State of Florida. We will be talking about his entrepreneurial journey, the life that he lives now, and the life that he lived beforehand. What we like to do here on the show is get down into the spiritual realm and talk about MasterMission and how entrepreneurs, business owners, and people who work for a living and have a family, but maybe they have something else like a purpose or something else that drives them to do what they do. Go out there and whatever journey they are on, the work that they do, or the thing that matters most to them. How do you engage in that to make your life more meaningful? Steve Cavanaugh, welcome to the show.

Thank you so much for having me. It's always a pleasure to speak with you. I'm happy to speak with the audience.

If you were to write an autobiography but you are doing it in less than 3 to 5 minutes. Now I may ask some follow-up questions. Tell a little bit to the folks about where you came from, what work you have been doing, and your family. What does that look like for you?

I was born and raised in Southern Maryland, Western Shore in Chesapeake Bay in a little town called La Plata that no one has ever heard of. It's about 35 minutes south of Washington, DC. I grew up there. I had a good upbringing. I enjoyed it. I grew up on a small farm. It was a rural slowly becoming suburban. Now, it's very much a suburban and a bedroom community for Washington, DC. In any event, that's where I'm from.

Fast forward, I will cut out a whole lot of stuff and get you to the beginning of my career, which is probably what your readers are more interested in. I graduated from college in 1999. I immediately took a job in the IT field, which had nothing to do with any degrees that I earned in college, which is fun. The silver lining in my work experience and my job from 9:00 to 5:00, which was more like 9:00 to 6:00 or 7:00. The experience was I didn't like to commute an hour to work and then an hour on the way home. I didn't like to have a supervisor telling me what to do.

I have always had this rebellious streak about me. That certainly was at play when I was in that job. For four long years, I had to do something else. I read Rich Dad Poor Dad. The CASHFLOW Quadrant was the first book that I read, which was the sequel to Rich Dad Poor Dad for those of you taking notes at home. I said, “I could do this. This is awesome. This sounds great.”

Long story short, I bought a rental property. On the day that I closed on that first rental property, I had to have a job in order to qualify for the mortgage to buy the rental property. On that day that I closed on it, it was a day off. It was a Friday that I had taken off. I drove down. It was like out of a novel. It was a rainy day. It was the afternoon. It was dark outside and everything. I left the settlement with my title binder and folder in my hand. I was super excited. I just bought this property.

I drove an hour to my job so that I could hand my two weeks’ notice to my boss in person on that Friday because I had used the job for all it was good for, including qualifying for the mortgage, that one last thing that happened there at the job. I didn't make it the full two weeks. I had a trip plan with my buddy to go up to some concerts in New York. I made it a week and a half and I said, “See you later.” I took some vacation days, those last couple of days.

That's what I did. I had a mentor, a woman who had an office near where I was working in those days. A mutual friend of ours said, “I could introduce you to this woman. She knows what's going on in this county that we were at.” She introduced me to the tax rolls. She sat us down. I don't know if you remember doing this, but there were books on the tax rolls. They were big and you had to have a big conference table to lay them out on. She had this little magnifying glass that you would read the lines.

That's how we marketed to this neighborhood that she turned me and a couple of friends into and she said, “The builders are building.” Keep in mind that this is when things are starting to ramp up before that 2005 time. She said, “Write down all this information, all these people's addresses, and mail to them because builders are hungry for lots in this particular neighborhood.” Sure enough, I went home and I did a very small marketing campaign to that neighborhood.

Very long story short, I had a gentleman call me. He had two of these lots for sale. We were able to put them on a contract. We ended up flipping them to a local builder and that deal made over $100,000. That was a $100,000 wholesale deal, 2 lots right off the bat. I said, “This works. This is good.” I took that money and then I put it into some marketing. I had a tiny little classified ad in the back of PennySaver.

I had calls coming out from PennySaver. One of them was a townhouse that a woman was looking to sell. We bought that property and I made around $63,000 on that first rehab deal. I took it as a sign from God that this should be something that I should be involved in. That's when everything started moving from that point moving forward. That was back in 2004 when I first got started. It's been a journey.

You started in Southern Maryland. You lived there for a while. You had your job. Now, your entrepreneurial journey starts. I know but the audience may not know, now you live in Florida. How did you get there? What's business like? How do you operate your business being a person who has a business that still operates in Maryland, but lives full-time in the great State of Florida?

I love it here. I'm in Southeast Florida, West Palm Beach Area. My wife and I have been coming down here since the early 2000’s. Her folks moved down here from Long Island, New York. There are a lot of New Yorkers in New Jersey folks in the area who were leaving those states and droves, especially these days because they have high taxes. We have been coming down here for a long time. We fell in love with the area. It is exploding. There's no more room. If you are reading this, you can't move down here. We can't take any more people. We got room for Mike, but that's it. Sorry.

I have to back up. I have to give a lot of credit to Steve Cook and the folks at Lifeonaire, who has been a mentor, a coach, and a friend of mine for many years. Business life, spiritual, and all sorts of ways. A great confidant and just a great guy. He developed this Lifeonaire concept, which perhaps you have talked about in another episode which is, “Come up with a vision for your life. What do you want your life to look like without regard to money, business, or anything like that?” Once you figure out what you want your days to look like and your life to look like, and the time that you are spending on this earth to look like, then you can go ahead and backfill the business stuff in once you have filled your calendar up with the stuff that you want to do.

IDP 8 | Business Coaching
Business Coaching: Once you figure out what you want your life to look like, then you can go ahead and backfill the business stuff.

One of the things that became apparent throughout the years of coming down here and loving it so much and then having to go back to Maryland was that we wanted to move down here. We wanted to move our family down here. We wanted to live 2 miles from the beach, which is where we live now. We want year-round warm weather, which is, unfortunately, I have to say. What is it 2023?

It's something that we almost take for granted now. We don't even think about the fact that it would be freezing in Maryland or it'd be gray, rainy, drizzly, and just nasty. The lifestyle upgrade has been huge. As a result, we have been a much more active family. When it's cold outside, you just don't want to go outside.

Not to get off topic here. I want to stay true to a couple of things that we are going to talk about. One of the things about living in Memphis and a lot of our folks, sometimes they live in the Midwest. That is the thing that my wife and I noticed most. December, January, or February, if it's cold outside or if the weather is bad, we are not going to get active. I get it. Everybody I talk to has moved to Florida. The only negative that I hear from people is that, “We don't get the four seasons, but we get the best season,” is what they said.

You mentioned something about changes and mentorship. You talked about the mentor that you had. You talked about Steve Cook, the mentor who helped you get started in the business. With Steve and with other mentors in your life, how is having a mentor in the guidance of your spiritual life, what's that look like for you?

I had a pastor. We loved our pastor. Pastor Mike Hilson from New Life Church in La Plata when we were in Maryland. He was fantastic. He gave this sermon one time and he said he wanted to live his life in such a way that when people would look at him, then they would look up. Steve has done a very good job of living his life like that.

There are people who are gifted with and believe in pressing people and evangelizing. Trapping people in a corner and trying to push their beliefs on them or whatever the case might be. Steve is the exact opposite of that. Steve is like, “I'm going to go ahead and be a faithful guy and live my life. Whether you choose to take this or not, I'm not going to force you to live my life this way.” When you spend enough time with somebody like that, you can see the fruits in their life. Then it's up to you, whether you want to live your life that way or not.

Steve got that gift. I have also been mentored by Steve Cook. One of the things I noticed is that over time, the folks who come to him don't want to talk about faith. They don't want to talk about Jesus. They don't want to talk about those things. They just want, “I need mentorship for my business. My life and business is a wreck.” With those particular folks, Steve has always had a way of meeting them where they are. The walls come down and then like, “Tell me a little bit more about your faith.” I have seen that happen time and time again with that man. You nailed it.

We don't want to discount. There are people who are gifted in going and preaching the gospel. Our world needs that too. For Steve, he knows who his audience is. It's pretty interesting to see a lot of faith journeys be impacted by him. What's great is I have seen, like you, other guys that have been mentored by him do the same thing. It's Discipleship 101 and Steve Cook has been blessed doing that.

Steve Cavanaugh, you live in West Palm. One of the other things that you do besides real estate investments, you have some self-storage deals, but you also impact other people's lives. You have a group with Alex Pardo called Ascend. What I want you to tell the audience is how have you been impacted by the people in that group. They come to you for coaching and guidance, but let's reverse it a little bit. Talk about how coaching those people has had an effect on you and your spiritual journey.

Let me back all the way up and say I have coached people in real estate investment around the 2007 or 2008 timeframe starting then. I ran a coaching group in Southern Maryland for several years. We did a lot of deals through that program. I coached 43 people over that time period and we sold over $80 million worth of real estate projects that we were principals on. Not a small thing. I cut my teeth with leadership and coaching through that endeavor.

It was very fulfilling. I had a number of students leave their full-time jobs. As we were alluding to when you are placed in a leadership position, and then you have the ability to lead people in subtle, but positive and good ways. In any event, there's that. What do I get out of it is your question. It's very fulfilling when you have students who are able to provide for their retirement because they weren't going to have any.

I had one guy I worked with as an example. An older guy who’s retired. He was an airline pilot for American Airlines. After September 11th, 2001, in order for the airlines to stay in business, they had to essentially reenable their pensions for their retired pilots. He lost his pension. Everything he worked so hard and his entire career for was taken away from him as a result of this.

To his credit, instead of being a victim and woe was me, he said, “I'm going to learn a new skill and that's real estate investing, and this is going to help me pad my retirement or rebuild my retirement.” To have a hand in something like that is a pretty gratifying thing. I had another woman who was working three jobs or something crazy. She was able to do a handful of deals, buy some rental properties, and create some financial freedom for herself. That is extremely gratifying as well.

I want to take it a level deeper. I want to tell you stories about the MasterMission Trip. I have got another one coming up that I want an opportunity to talk about it if you don't mind. We had one a couple of years ago. A guy came on this MasterMission Trip, which MasterMission is part mission trip, part mastermind, part adventure trip, and part foodie trip. We have been getting better and better about going to good restaurants.

This takes place in Antigua, Guatemala. I lead a trip there once a year. It's a small group. It's twelve people. We try to get the right people together in a group. We stay in the same Airbnb. We stay in a very nice gated community. A very big house. We visit the poorest areas of Antigua, Guatemala. We support a school there called the Escuela Integrada.

What happens is I take these people down there who in many respects are high-level entrepreneurs, investors, and great strong people in their own right. They come down there. They see the poverty. We take them from a high place. We might be hiking up a volcano. The same day we go and then we are in some ten shack where the folks. They are malnourished. We are taking them food bags and we are praying with them in their homes.

As you can imagine, this serves to break people's barriers down. We are able then to uncover and peel back the layers of the onion in the mastermind session years of fear and false beliefs and help people break down all the facade to get onto what is the biggest life challenge for them. A lot of people think they have business challenges, but a lot of times business challenges are mental challenges or life challenges. People are just going too fast in this society to realize that. Something like this trip does a great job of helping break that down.

I'm thinking of a gentleman, who I won't mention his name, but he was on this trip with us a few years ago. He hadn't spoken with his dad in years. He and his dad had a messed-up relationship. His dad had gotten divorced from his mom. His dad went and remarried. Probably about 45 minutes into his 60-minute turn, one of the other gentlemen at the retreat challenged him and said, “Why don't you call your father right now?” We are there to push each other and nobody wants to be challenged. No man wants to be challenged and say, “No. I'm not going to do that.” He said, “That's a challenge. I will accept that.”

He got out his phone. After several failed attempts to get his dad on the phone, he was able to. He put his dad on speakerphone in front of the group. He said, “Long story short, I'm in Guatemala with a group of friends. I got telling them about our messed-up relationship. I just want to call you and tell you that I love you.” His dad said, “I don't even know how to say this, but I have been praying morning, noon, and night that you will call me someday. I'm so sorry. I didn't reach out to you. I thought that you and your sister had completely written me off. You had every reason to do it. I have just been ashamed that I have just wanted to extract myself from your life. I can't thank you enough for giving me a call. I love you.”

He's crying. Everybody is crying. The dad is crying. It was a beautiful event. He said, “I'd love to get together and have a cup of coffee with you when I get back to the States.” He said, “Please give me a call when you get back.” It was a great moment. He hung up the phone and we prayed over the guy and everything.

He has a relationship with his dad now. He's a young guy. He's going to have children. Now, they are going to get to know their grandfather. Generations have been restored as a result of running this trip leading and coaching people in this way. I could go on and on. I could probably spend the next hour telling you stories about people who have been impacted in very similar ways through the MasterMission.

IDP 8 | Business Coaching
Business Coaching: Generations have been restored as a result of running this trip and leading people in this way and coaching people in this way.

What's interesting talking about Antigua, Guatemala, and how we are going so fast. One of the things I hear when you are telling the story is that the people who are coming down the MasterMission are almost forced to slow down. For those that have been and haven't been, in Antigua, Guatemala, I have been six times. For some reason, there's this thing called Antigua Time that my wife and I talk about where we slow down. It just forces you to slow down.

The other thing that happens over there is you realize that in our American culture, our pace is crazy as far as how fast we go every day. I could tell you that I have been going 90 to nothing since I got up. Antigua slows you down. When you get a bunch of entrepreneurs and business owners over there and they are slowed down, and you take them through that process of showing them what real life is like for most people around the world. I can see how that would break down walls and barriers.

Tell me another story because I love these stories. I'm having a hard time keeping myself together when I hear that when a dad and a son reunite, it's the best feeling ever. We were talking about another meeting that I had. Somebody asked the question on eight of us, “What's the last movie you cried at?” It's like, “There's no movie that I cried at.” I can't remember, but Field of Dreams is a movie where when the dad plays catch with his son, it gets me every time. It's the end of the movie.

Sorry, if I ruined it for you. That gets me every time. Steve, tell me another story about somebody who came on your MasterMission Trip. I know some of these people know that they are going and know a little bit of details, but some of them are going for the first time and they don't know what to expect. Give me another story there.

I have got a great one for you. If you want to hear about God's hand and how he has shown himself in my life. This is amazing. I just ran a trip. I live in a nice gated community here in Southeast Florida. In the middle of our neighborhood, we have a clubhouse that's got a tiki bar and the pool and everything. What happens is the families will gather there every Friday night. We usually have a live band or a DJ. It's a lot of fun.

There is an element. It's just like any other place you might go where you got your people who are there to hang out. You got your drunks. I tend to avoid the drunks. I don't have a problem with people drinking. I like to have a margarita now and again there. There are people who spend $3,000 a month drinking. One of these guys I knew, but it was one of these things where every time he would come up, I would try to end the conversation with him as quickly as possible. Be nice and kind to him, but try to find someone else to talk to. I have been playing a lot of pickleball. Have you played pickleball yet?

I have not played, but I have seen you on Instagram playing pickleball.

You are going to get addicted as soon as you play, so be careful. It's instantly addicting, but it's a lot of fun. We have courts next to the tiki bar in our neighborhood. I have been playing these Monday nights. The same guy from the bar would come play on Monday nights. He's got a Hispanic background. I was in Antigua in the fall and when I got back, I was showing the guys one night just the pictures of how beautiful it is in Antigua with the volcanoes and the sunset. There's an active volcano there, Fuego, that shoots up. You can see the lava and everything. It's cool. It's not dangerous or anything. It's just neat.

I'm showing him all these pictures. This is in the fall. He says, “I might want to go on that trip with you.” Immediately, I'm thinking, “There's no way I'd want to take this guy. He'd be drunk. He'd be everything.” The months go by and I get closer and closer. Now it's January and I'm running the trip the next month in February. He comes up to me again. He's like, “Do you have any more room on your trip?”

Keep in mind, this guy is not an entrepreneur or business owner. He's a guy who works a couple of jobs. He's got a family. I was like, “Let's talk about it. Maybe, I will have a spot. I'm still not sure.” I go home. I talked to my wife about it. She's like, “I don't know. You don't want your reputation in Guatemala to get ruined by taking the wrong guy and all the stuff.”

A big event happens where a bunch of guys from my neighborhood and some other guys. They all get together and they get blasted one night. They end up at the strip club. They end up going to the VIP in the strip club. I have never been in a VIP in a strip club, but I can only imagine what takes place there. $5,000 later, and my friend who I'm talking about was there. He passed out in the strip club. He was asked to leave after he ran up $5,000 on his credit card. It was one of those rock-bottom things that needed to happen.

He got home at 3:00 in the morning. His wife had already been called by the credit card company saying, “We believe there are fraudulent credit card charges because this is an irregular pattern of activity on your credit card.” He comes home to his wife early in the morning and just passes out drunk. It was one of those this-is-it moments like, “This isn't the life that I want to be living.”

I find out about it the next week. My buddy comes to me and is like, “I hit rock bottom.” I had the opportunity to have a conversation with him about it. I said, “I want you to go to Guatemala with me. It would be a good opportunity for you to go to Guatemala.” At the same time, a men's group was starting up a church. He said, “I want to start taking my family to the same church that you guys go to.”

I said, “You should also come to this men's group with me. You should go to Guatemala with me.” I pitched to him. I said, “You speak Spanish. You could help our group.” I'm trying to give him some empowerment in that moment to give him a compelling reason why he could be helpful to us. This is a guy who probably for many years of his life has not felt like he's helpful to anybody.

He goes home. He talks to his wife about it. His wife says, “Yes. You should go with Steve to Guatemala.” He comes along with us. Again, he's not an entrepreneur or a business guy, but he comes along with us. We are there. I was afraid the first day that he was just going to drink anything in sight. We did an event, the very first thing. We had a historian come and give us some local history of Guatemala, but he also provided us with a bottle of Ron Zacapa rum. That's making the rounds a little bit. I'm just like, “I hope that this guy doesn't just suck down.” He didn't drink a drop. He had committed to his wife that he wouldn't drink in the future.

Everyone gets 60 minutes to talk their talk, to say their thing, and to use the group coaching environment throughout the course of the week. During his turn, it was revealed that not only did he have several tours of duty overseas where he was very active in war duties. Read into that what you will. Growing up, it sounds like his dad was a real monster. He believes that his dad killed his mom. That came out. His dad was such a monster that when he killed his mom and the mom had a funeral, he would not allow my friend and then my friend's brother to attend the funeral. He never had any closure over his mother's death whatsoever.

You can see, I'm not making excuses for bad habits, but this guy had a drinking problem for a reason. There was a lot of pain to medicate there. Long story short, this all came out in the group coaching environment and he got healing as a result. We all stood around him and prayed at the end of his 60 minutes. He's done very well in the men's group that he and I continued to be a part of, and I have become good friends with this guy.

It's not what the Lord was doing in his life. It's also what the Lord was doing in my life and everybody else in the group. As you are sitting there looking at these mystical volcanoes, as these conversations and healing are happening, it's such an overwhelming and spiritual feeling that I haven't had anywhere else. It's not to say I haven't had spiritual encounters, but these are very powerful. I don't want to promise anybody that if they go with me on this trip, they are going to have a spiritual encounter. I will say that I get filled up on these trips when things like this happen with my buddy. That's a good one.

The Lord has a way of messing with our assumptions and he does a great job of it. Look what he did. I appreciate you sharing that story because there's somebody out there reading who probably has some similar background or story. The scripture says that all things work together for the good. This guy's whole life, his deep valleys that he had, he was able to see something in Antigua that God showed him and put him on the path. It's cool to see that you are listening to the Lord and that you are a part of that.

I want to piggyback on what you just said. His wife came up to me a week or two after we got back from the trip. She said something to the effect of, “Why would you even consider taking him on the trip with you? What did you see? Why him? Why would he go? He's been talking about your trip nonstop. He's talking about all the different people and the personalities on the trip. I know them now through his story, but why would you take him?” I'm going to tell you and your readers exactly why I took him. It’s because that week before when I looked into his eyes, I could see the spirit in his eyes. That's exactly what I saw.

Here's the deal. I am running another MasterMission for sure in 2024, February 7th through the 12th. That's a Wednesday through a Monday. It's If you guys want to go on there and check it out. I want to say this is not a money-making venture for me. I pay my way like everyone else. Room and board. We eat very good meals. We have a staff at the house that makes our beds for us and cooks us breakfast.

IDP 8 | Business Coaching
Business Coaching: I am running another MasterMission for sure in 2024, February 7th through the 12th.

Antigua was a great tourist spot too. Some people want to go sleep on dirt floors. That's not what we do. If that's what the trip but it’s not this trip. We live in very luxury accommodations where we are, but we experience extreme poverty while we are there and it's part of the experience. You should be okay with that. It's $2,000 is what it's set at. The only other cost you have to bear is your flight there. We get together in the States. We meet in Fort Lauderdale, Florida. We fly out on the same flight into Guatemala City. I will be with you the entire time. I'm not going to let you fend for yourself in Guatemala City. It's an hour or hour and a half ride, I'm saying that tongue in cheek, to Antigua. Everything is taken care of is my point. It's completely safe. I have been to many cities in America where I have felt much more in danger than I ever have in Guatemala. Regardless of what you may have heard, it's a safe trip.

There is a possibility. I want to put this out there. I don't know that I'm doing this yet, but I’m eyeing the first week of December of 2023 to potentially do a small men's trip where we do adventure only. We are going to camp at the base of the active volcano, where we get sprayed with some lava maybe overnight. No. I'm just kidding. We are looking at camping, doing an ATV tour, hiking volcanoes, and stuff like that. There's that too.

Thank you again for coming on the show. If you want to know more information about MasterMission, it's You can find out when those MasterMissions are happening, a little bit more about the school that Steve sponsors, and all the things. Steve, thanks for coming on. We will see you, guys, next time.

Important Links