Darren Jacklin If YOU had $1M dollars what could YOU do with it?
Darren Jacklin If YOU had $1M dollars what could YOU do with it?


Recently, I went to dinner with a group of CEOs, and I ended up at the end of the table with a chatty guy who seemed curious and in love with meeting people. I’m an introvert, so I warm up slowly, but the questions coming from this guy were both interesting and meaningful! He asked me, if I had $100 million in my name, what could I do with it? What would I actually do with unlimited wealth? He said that most people can’t answer that question. And frankly, it’s because they are self-focused. To become other focused, we can now see billions of people in need, and the resources we need to help them are only a few mindset shifts away. Sir Darren Jacklin, one of the most successful corporate trainers in the nation, sits on the Board of Directors of eXp World Holdings and other publicly traded companies. He truly is a global philanthropist and enjoys traveling worldwide to promote Elevate 2 Educate, a non-profit organization dedicated to ending human trafficking.

Darren says, “My success is someone else’s miracle.” This is a mindset I love because it draws success and resources to us from a place of love and need rather than pleasure or indulgence. Marcus Aurelius said life is long if you know how to use it. Darren is helping me to see life differently, and I want to share his philosophy with you. Please don’t forget to like these episodes, share them out, and also subscribe. It may seem small, but it helps the algorithms that help us grow and ensures that you don’t miss out on any new and interesting conversations. It also helps us to see that you like what we are doing.

So, if you do like our show, please share that good news with us!

Here is Darren Jacklin. Thank you for listening!

Connect with Darren Jacklin here:


For video versions of podcast:


Connect with Jeramie and our business:


Copy of Jeramie’s book, workbook or audiobook:


Link to our website:

Worley Real Estate Network – Helping agents and investors get a greater return on their time.

Want the best data tool for Short Term Rental Agents to achieve mastery in their real estate business: https://vrolio.typeform.com/worleynetwork

Listen to the podcast here


Darren Jacklin | If YOU Had $100M Dollars, What Could YOU Do With It?

I went to dinner with a group of CEOs and I ended up at the end of the table with a chatty guy who seemed curious and in love with meeting new people. I’m an introvert, so I warm up pretty slowly, but the questions coming from this guy fit the bill. They were both interesting and meaningful. He asked me what I would do with it if I had $100 million in my name. He said, “Most people can’t answer that question. Frankly, it’s because they’re self-focused.” To become other focused, we can now see billions of people in need and the resources that we need to help them are only a few mindset shifts away.

Darren Jacklin is one of the most successful corporate trainers in the nation and sits on the Board of Directors of eXp World Holdings and other publicly traded companies. He’s truly a global philanthropist and enjoys traveling worldwide, promoting Elevate 2 Educate, a nonprofit organization that’s dedicated to ending human trafficking.

Darren says, “My success is somebody else’s miracle,” which is a mindset that I love because it draws success and resources to us from a place of need rather than pleasure or indulgence. Marcus Aurelius said that life is long if you know how to use it. Darren is helping me see life differently and I want to share his philosophy with you. Here’s Darren Jacklin.


Cocktails and Dreams Real Estate Podcast | Darren Jacklin | $100M Dollars


You don’t eat meat.

I eat fish and chicken.

Health choice or personal choice?

It affects my energy level. I get tired. I have been that way all my life. If I eat hamburgers, I get tired.

It’s not the carbs. It’s the beef. It’s the meat.

I was also told it’s my blood type as well.

I didn’t know that there was a correlation there. We know you are all about your health and your energy because you summited Mount Kilimanjaro. Tell us that story.

At age 48, I realized I was overweight. I was traveling all the time all over the world. What happened was I wanted to get into shape. I wanted to start to change my life. I started to hike in Vancouver, Canada. I started hiking with a hiking group. What happened was I started posting and documenting on social media the progress I was making because I released 43 pounds in weight.

You say you released 43 pounds of weight. You didn’t say you lose it because there’s a difference there.

When you lose something, the human brain wants to go find it again. It wants to locate it again. If you lose weight, your brain will want to go find the weight again. Usually, you up and down. When you release it, you’re programming your subconscious mind to say, “I’ve released it, it’s gone for good or gone forever.”

I was posting on social media and a friend of mine, Aaron Kleinerman, reached out to me and he says, “Can we jump on a fifteen-minute Zoom call to catch up?” We jump on a Zoom video call and he’s like, “I’ve been following you on your social media channels. I know you’ve been releasing all this weight. Your body’s transforming. You’re changing. People are coming with you, hiking from all over the world. Would you consider climbing Mount Kilimanjaro in Tanzania, East Africa with me?”

I said, “Absolutely not.” He’s like, “Why would you say that?” I said, “I’m not an athlete. That’s not me. I’m not genetically wired that way.” He is like, “Those are all excuses, Darren. You’re an overachiever in business and finance and stuff like that that you do. The thing is you should be able to do this.” I was introduced to somebody else who is 100% legally blind, and he summited Mount Kilimanjaro with a guide at Mount Everest base camp.

The guide told me, “I’m legally blind. I summited both of these mountains. What’s your excuse?” That was a turning point where we realized, “I should train for this.” I trained a year for Mount Kilimanjaro to go up 19,340 feet in elevation, so about 5,895 meters. It was a phenomenal life-changing experience. There were so many life lessons I unpacked from that, so many takeaways from the mountain.

Now, it’s opened up a lot of doors and opportunities, and I’ve got a guy who I’ve known for twenty years. He’s done 6 of the top 7 summits on the planet. The only summit he’s got left to do is Antarctica, Mount Vinson. We’re scheduled for January 2025. They only allow 100 climbers a calendar year to go up to Antarctica to do this mountain.

It’s rated as the coldest place on planet Earth geographically. It’s the South Pole. We’re going to do it in January 2025, which is 24 hours of daylight, but prepare now for 15 months. It’s about 15 to 16 months of training development in various different scenarios. We do best case scenario, likely case scenario, and worst case scenario to plan and prepare for that.

You’re training for all of these things.

Yes, for snow conditions, blizzard conditions, crevasses, and all that stuff, you train. I trained in Whistler, British Columbia, Canada, and probably down in Colorado sometimes as well.

Did you ever think that you would do anything like this in your life?

Never in my lifetime. I have over 7,000 written goals. This was not one of them.

When did you write down those goals?

I’ve been doing this for a couple of decades now of writing goals. I started when I was about 18 or 19 years old. I was even younger than that. I started writing goals down, but only like 5 or 10 written goals. In my 20s and my 30s, I got more and more serious. When I started to achieve bigger goals, personally and professionally, then I became committed. Things started to take off in my late 30s and my 40s. I was on a lot of airplanes, traveling a lot. When I’m on the airplane, I would put my headphones on and put inspiring music on. I’d be on an 8, 10, 12 or 16-hour international flight and I would start brain dumping different goals and dreams.

I would be looking through different magazines, watching different YouTube videos, different documentaries, talking to different people, having conversations, and getting different ideas. Even with hiking now, I belong to different hiking groups throughout North America and also internationally, so people post online all these different hiking trails. I go to all trails, I check it out, and add it to my goal list.

Different travel goals, humanitarian goals, philanthropy goals, financial goals, health goals, relationship goals, business goals, acquiring companies, and more real estate businesses. I have a list of secret goals that no one will know until I die that I will do around the world, secret goals that I will serve people and contribute to people’s lives and do things anonymously.

I have a list of secret goals that no one will know until I die. These secret goals of serving people, contributing to people's lives, and doing things anonymously. Click To Tweet

After you’ve passed. You’ve set it up.

I set it up, and I have things I do throughout the world. Nobody knows, not even my partner. I do it privately. It’s within my heart, and upon my death, if people take the time to read through all my list of goals that I’ve checked off and achieved, they’ll see my list of private goals.

You’ll serve humanity one last time. That’s phenomenal. You seem to have a lot of energy. At 47, I probably have half the amount of energy that you do, or at least it feels like it because entrepreneurs oftentimes pursue many different pathways at once. There’s a mental energy burn that can take a toll on the physical body as well. Do you ever get ambition fatigue?

I do if I’m doing things that are not to my highest hierarchy of values or directly in line with my mission or vision. I do things that if they’re a shiny object or distraction, I get depleted of energy. If I’m doing low-priority activities, for example, if you had me cook, some people like cooking, I don’t. I’d rather make reservations, hire a chef, or have food delivered. House cleaning, things like that, if I’m doing those types of things, I drain my energy. I’m always working with things that are in my hierarchy of values of what’s most important in my life.

One of my questions for you is how do you filter the decisions that you make or the opportunities that you take on?

The team of people around me. I have people around me. I have a couple of other females around me, women, that do this. They filter and go through things. That’s a big thing because I qualify my time. To protect my time is a big thing. You saw all the messages that come through my social media channels and emails on a daily basis of being pitched for things. It’s unbelievable.

How many is it, do you think?

Sometimes it could be a couple of hundred in a week. I know some people that are in a lot more. Between all the platforms, a few hundred times a week.

Do you have an admin that filters through them?

I have a chief operations officer who goes through stuff, and I do have an admin person as well. There are certain people with the inner circle that have been vetted and prequalified that when things come through them, I know that they’ve been vetted, there’s been due diligence on it, or at least discovery, so I take it more seriously. It’s more of a higher priority to take that person. I always get approached by people wanting me to write them a check and solve their financial problems. I get that daily.

How do you handle that?

I got two in one day. I got a guy who blew his motor in his vehicle and wanted me to know if I’d pay for his engine.

How did he find you?

He sent me a private message through LinkedIn.

He thought you had money and might want to help.

I don’t even know who he is. I wouldn’t know if he walked right by here now. I have no idea. Another guy wanted to know if I’d pay for his daughter to put her through university.

When did that start happening to you?

It would’ve started probably the first time I went to NASDAQ to ring the closing bell, 2018 with eXp. I got multiple mailing lists. I think my information got out there publicly on the internet because when you’re a publicly traded company, you’re on a board of directors. A lot of these financial people across North America that are in the financial services industry want you as a client because you’re like a whale client to them. They want to leverage you and they also want to sell you products and services. You get on these databases and then they start calling you and trying to get to you all the time and stuff. There are ways to pre-qualify those people as well.

I want to take a little time and let the audience know that you are on the board of directors at eXp Realty, one of the most revolutionary and disruptive real estate companies, following a pathway of other disruptors. I moved my team, my brokerage over to eXp, and I vetted the company out. My leadership team tried to break it. We took eight months and we tried to break it. We couldn’t. There was still a lot of interesting transitions moving over as we were a fiercely independent brokerage. For me, it was very difficult to come under the submission of new leadership because that’s one of the issues in my life that I’ve always had.

Aside from my dad and my grandfather and strong men in my life who love me passionately and care deeply for me, I’ve had a lack of great mentors. I’ve been forced in my life to learn everything myself as I go. I’m the guy that would look at Mount Kilimanjaro and say, “I’m going to do that.” I wouldn’t wait for somebody to say, “You should do this.”

I’m fascinated by your approach. I want to dig into a couple other stories that you talked about. In a way, Darren, it was difficult for me to come under this submission of leadership because, biblically, I believe that’s what we’re supposed to do. In order to be exalted, we must submit to authority, whether that’s your dad, a spiritual authority, a boss, or a leadership in an organization. I have found that God has unlocked the greatest opportunities for me when I come under submission. eXp Con 2022 was the first time I got to hear Glenn speak. I was relieved to see such a humble man.

He’s a humble, integral, heart-centered man. He deeply cares about people.

Meeting you at BA and spending a little time with you made me feel alive again. It restored my belief that people with means aren’t out to get you. It’s very hard to find someone, in my experience, with means that actually cares.

Also with high levels of integrity.

That’s why I’ve had a difficult time submitting to mentors. Let me tell you an example of one. I have had the opportunity to connect with some very high-level private equity firms. A gentleman that I know, we were in New York together. This person I know, I think a lot of him. He’s very smart. He’s one of the smartest people that I’ve ever met in my entire life in terms of real estate and commercial real estate. He’s still one of those people that I can call.

He’s got a great background, too. I decided that that’s the guy that I want to be like or a version of that guy. I’m always going to be myself. We got back from dinner one night and an interesting thing happened to me. I’d never seen a prostitute in my entire life. We went to New York and this woman flashed her coat open as we were going by. It caught my eye and I asked my friend, “Is that a prostitute?” He’s like, “Yes.”

I’m fascinated by people. I watch people. I watched that prostitute from the balcony. A few minutes went by and this gentleman, who I thought very highly of and still do, I watched him go over to the prostitute, lean in, have a conversation and they both left for the elevator. I felt absolutely defeated. What that does for me is I’m unable to learn from that person anymore.

The trust was broken.

It was. I still trust him, but I don’t trust him with my future. I trust him with information. I trust that he’s an expert in a category, but I don’t trust him with my future, which means my family’s future and my legacy. It was an honor to meet you because of your accomplishments. I’ve begun to recognize a pattern in your accomplishments and in your achievements. eXp is interesting because you were one of the original three who started the company and you’re so humble about it. It’s unlocked a lot of doors for you. Tell me a little bit about what it was like in the beginning. eXp is an unknown company. It’s you, Glenn, and Jason Gesing.

I came in 2013. There was a couple of hundred people in total in the whole company. I came on as the first independent board of directors member. There was Glenn Sanford, the Founder, Jason Gesing, and myself. I was the first independent director. The three of us would meet every Thursday morning at 8:00 AM Pacific time for a standup meeting.

What kind of things were you talking about in those days?

We were looking at things from a compliance standpoint. Compliance is a big thing. Also, risk mitigation and asset protection.

Talk about compliance. I was introduced to eXp many years ago by someone in my market who didn’t know how to pitch it. It’s a very intelligent company. It’s not easy to get people to take the time to understand it. I cared about my agents so deeply and I thought, “There’s no way that this one broker in the state of Missouri is going to take care of my agents the way I would.” I had 50 agents.

They’re like family to you.

Honestly, I grilled Chris, who’s our Missouri broker. The man is phenomenal. He’s got a great leadership team. Since coming over, I haven’t had a single agent complain about that. That was a limiting belief for me. There was absolutely no way this is going to work. Did you have those kinds of conversations to overcome those?

In the early days, we had a lot of critics, skeptics, and naysayers. I had people that I’ve known for many years because I spent 25 years traveling the world as a corporate trainer as well. I used to travel almost 300 days a year globally. I had a lot of people in the real estate industry that ran mega teams and large franchise. I had a lot of financial investments involved. They would come and actually do interventions with me. They were concerned for me going down a path with a startup company, an unproven model with no financial backing and building airplanes while flying it. They were concerned for me. They wanted to come in and say, “Darren, you have to realize something. I’ve been doing this for many years, a lot longer than you. You don’t know what’s going on here.”

They were worried about your reputation.

Also, I was in the wrong environment with people and stuff. It was interesting because when I was going through my discovery and due diligence as well for eXp to serve on the board and being asked for that, I went to 73 different people. I made a list in my journal. All 73 people across North America said, “Do not get involved in this company.”

Why would you do it?

The family that introduced me to Glenn was an ultra-high net worth family and they were writing a check. I was following the money because they had financial skin in the game. Nobody else was writing a check. I’ve been involved in rooms before where people think it is a great idea. I started to watch people, and I’m thinking, “Of all the people I talked to, the family that I dealt with was one of the most successful families in North America.” They’re more successful than some of the other people I was talking to.

Why did they decide to do it?

They’d known Glenn for many years and they had financially invested with Glenn before in previous ventures back in the 1990s.

There’s a trust factor there.

History, experience, and trust factor. They get to know and trust each other. They introduced me to Glenn in 2013. It was interesting because in 2011, I was flying from San Francisco to New York on United Airlines. I wrote down in my journal that, as part of my 7,000 goals, I wanted to get onto paid advisory boards and paid boards of directors of public and private companies. I had all these people, all these naysayers, saying, “Darren, listen, you barely passed public high school. You don’t have an MBA. You don’t have a PhD. It’s not going to happen. You’re not going to get on paid advisory boards and paid boards of directors.” Now, I serve on multiple paid advisory boards and boards of directors of companies.

Here’s what I don’t understand. You’re already a successful person and you made the decision to pursue growing eXp Realty. Shouldn’t your track record of success be enough for your friends to say, “Darren’s making a good decision here?” Why did they care so much to try to stop you from doing something?

I was very successful like yourself. Being in your brokerage and your market center, why switch and come to eXp? You’re already established as a brand. You already have a reputation in the community. I was already known in my industry of corporate training, travel in the world, training the largest companies in the world, and works on the most successful in influential people in the world. They were concerned that this is a shiny object is a startup residential real estate company. I was already working with RE/MAX, Coldwell Banker, Century 21, and all these other companies. They ask, “Why would you go to this startup unknown company that has no money that’s building airplanes while flying it?”

When we did come over to eXp, half of my team didn’t come with me. I had this leadership moment because my values had changed. I had been praying for an opportunity. As a matter of fact, God spoke to me very directly and he asked me if I would be willing to be an apostle for him to the people in the business world. I was in my hot tub. I was very stressed. We had done $256 million in 2022, over 900 transactions. I had to make my wife disband her team so that she could come in and help me broker that. I have a Theater degree, Darren. I don’t know how to do any of this. I figured all of this out as I went.

I solved the problems for the agents. The agents became my calling card. I would do anything for them. I fought fiercely for them. It was difficult when I felt like they didn’t believe in me to take this to the next level. I understand it differently now. I read a book by a man named Sam Chand. He’s a great leader, especially to pastors and other business people. His book is called Leadership Pain. I highly recommend the book. He also wrote a book called How Leaders Create Chaos, which is another good one.

Sam Chand’s book nourished me during this time because I went into a deep depression, which is a difficult time to go into a deep depression, just as I’m trying to grow my career and as the almighty God has asked me to do something for him. You find this in Old Testament stories often. It was difficult for me because people who I helped raise them up in life, I felt like they had a different opinion of me.

I felt like what you said. They perceived that I had a Shiny Object syndrome, when really, my goal increased. It multiplied in my own mind. I knew that I had to become a different man and I knew that I needed the operating systems for accounting and brokering that eXp could provide so I could sow into the lives of the 5,000 people I haven’t met yet, not the 50 people that were right in front of me.

It was difficult, but Sam Chand’s book said, “Leadership equals growth. Growth equals change. Change equals pain. Leadership equals pain.” It was a rite of passage for me as a leader, and it took me a while to understand it fully. I was waiting to hear from God to make the decision to join eXp or not because all of these people had their lives riding on my decision and the leadership team. It was one of those moments.

Leadership equals growth. Growth equals change. Change equals pain, so leadership equals pain. Click To Tweet

It’s like when you asked your dad for something. If your kids ask you for something and they ask you for a bike, they’re like, “Dad, can I have a bike?” You love your kid. You want your kid to have things. You’re like, “I would love for you to have a bike.” Your kid comes back to you the next day and says, “Dad, where’s my bike?” How did that make you feel?

The kid’s like, “Dad, you remember when you said yesterday that you would give me that bike? Thank you. Whenever you’re ready to get me that bike, I want to thank you because I know you love me and I’m ready for that bike whenever you’re ready and willing for me to have that.” That’s my relationship with God. That’s how I treat that relationship. I have kids. I love being a dad and I understand the mind of God being a dad. This was a moment where I was like, “I need an answer right now. I need this.”

I was praying, saying, “Lord, I need to hear from you now.” I stepped out of my hot tub. I took three steps. I had taken two days to decompress. It was 11:00 in the morning. I took 2 to 3 steps and my knees buckled and I hit the ground. I had to catch myself on the beam that holds the stairs up. The best way to describe it is that I went into almost like a trance state. I heard very clearly in my spirit and tears started flowing for no reason. I felt all the pain and stress that I had felt for the previous year, the weight of all the decisions that I have to make, and all of the pain that I knew that I would have to go through on a new journey.

I felt God asking me, “This feeling that you feel right now, there’s other business people in the world that feel like that. Will you go to them? Will you tell them that I love them and to not give up?” I made a decision to say yes. That’s the decision that I made to join eXp, so here we are now. The leadership is important to me. My relationship with you is important to me because it is part of that.

I feel like I’m now able to connect with people all over the world. My network has grown severely and I’m able to, in a cool relational way, ask people how they’re doing and build relationships, which I didn’t realize until 2023 how much I love to do it. I thought I was an introvert. You seem to love to network and build relationships.

I love people. The thing is that I can look into people’s eyes and I can see pain or trauma. I can see if they’re not good enough, not smart enough, not worthy enough, they don’t matter, or they’re invisible. I felt all those things growing up. I can look into somebody’s eyes and I can dial right into someone. I recognize it. I’ve never done drugs before in my life, so I don’t recognize narcotic people. People say they’ve been in AA or Narcotics Anonymous. I don’t relate to that because I’ve never abused drugs or alcohol in my life. When I was under stress, I’d always go knock on doors when I was a kid and solve people’s problems, like cutting their grass, shoveling their snow, delivering newspapers, raking leaves, painting fences, and doing things like that.

I was always being in service because I always realized that growing up, we don’t have money problems. We have thinking problems. There’s no lack of money. Go solve a problem and serve people. As human beings, all we are is a network of conversations. Everything you want in your life is going to come from conversations. People always say to me, “You have 7,000 written goals. How do you expect to ever accomplish that in your lifetime?” I said, “I don’t have to accomplish it by myself because most of my goals and dreams don’t require my actions.” It’s all about creating teams and teamwork. Now with artificial diligence and virtual assistants, I can have things happening all the time, achieving these goals and dreams.

Your origin story is very interesting. You were a melon salesman.

Watermelon on the side of the road.

I am the great-grandson of a watermelon salesman. Southeast Missouri.

I picked thousands and thousands of watermelon and cantaloupe. To this day, I don’t eat cantaloupe anymore because I ate so many of them growing up when I was homeless and financially broke on the street. I got a job picking watermelon and cantaloupe. I still eat watermelon. I learned a lot doing that.

What did you learn?

The thing was is that the farmer I worked with was a very integral man. He did everything by his reputation. He was known by his melons. He was very passionate. He talked to his melons all the time out in the field. He knew everybody. He was very good at a network of conversations at the farmer’s markets, meeting other farmers, bartering, and trading stuff. I learned the power of the relationships of how they take care of each other in community, which is important.

No matter if you have a great crop that year or you don’t have a good crop, they still take care of each other. That was very important. Also, the importance of your word and the handshake. I saw many handshake deals on the farm while I was working over there. Somebody came by and needed to borrow the tractor or something, it was all done by a handshake. Also, the importance of the integrity of that. Your word is your bond. Your word creates your world. That’s very important to me with that.

What’s interesting about you being a melon farmer is in your book, you talk about this wealthy gentleman coming to you saying, “Get in my car and let’s go take a look,” and casting a vision for you of this vacant lot. He asks you what you see in this vacant lot and you are unable to see it.

I saw a chain link fence with an empty real estate lot.

He saw a real estate development.

He saw how he could generate 4 or 5 story commercial real estate building, generate the cash from that building, borrow money from investors to build that building, and then create positive cashflow that actually created another home for him. Every time he built assets, he could actually build another real estate property.

Did he buy watermelons from you?

He did. That’s why I met him on the side of the road.

He must’ve liked you.

What happened was I was on welfare. I was working for cash at the watermelon farm on the side of the highway. He came by in a Lincoln Town car. It was the first time I’d ever seen a $1,000 Canadian dollar bill at the time. They don’t have it anymore, but it was crazy. He had five $1,000 bills. I’d never seen it before in my entire life, only on television. This guy had a billfold of five crisp $1,000 bills. I was intrigued by that. How does somebody do that? Here I am, down on my luck. I’m flat broke financially, trying to figure out where my next dollar is going to come from.

Did you not have ambition at that time?

I did. I had ambitions, but I was also scared. I had a lot of uncertainty, fear, negative self-talk, and criticism around me in my environment. I was never going to amount to much and never do any else in my life. I was playing the role of the victim. “Why me? Why does this have to happen to me?” I was playing the blame game. He came by and bought a whole bunch of watermelon. Most people come by and buy less than $10 with watermelon on the side of a highway. He came back 3 or 4 days in a row to buy watermelon. He was buying about $50 or $100 quantities of watermelons.

I thought, “This is strange. It’s a different pattern. Nobody does this.” He must be going down the road and reselling the watermelon because we know we had a great reputation and best in class watermelon. On the final day, I asked him, “Sir, would it be okay if we get together sometime? I’d like to learn more about you.” I set up a time with him to meet him at a coffee shop. I didn’t have a vehicle because my car got repossessed. I actually borrowed a vehicle for a friend of mine and actually borrowed $20. I didn’t have any money. I was getting paid every Friday from the farmer. I borrowed $20 from a friend of mine. I also bought his car and went and drove up to this guy, Harry’s house.

He ended up in the country. I got to this big huge log house out in the country. I thought, “How do people live this way? This is a massive size log house, probably 10,000 square feet.” I ring the door buzzer and this lady comes and she goes, “You’re here to see Harry. Come on in. Can I make you something to eat?” I thought it was either his wife or his daughter. I said, “No, that’s fine,” even though I was hungry. I wanted to be a professional and not ask for anything. She asked me 3 or 4 times, “Can I make you something to eat?” I said, “No, that’s fine.”

Harry comes downstairs, he goes, “Did my girl make you something to eat?” I said, “No.” I said, “Harry, is this your daughter or wife?” He goes, “No, it’s my personal chef.” I said, “How does somebody have a personal chef?” That’s something I see on television. I’ve never met somebody with a personal chef. That was very powerful to see that.

Harry then said, “Will you stick around tonight? I’ve got a team of people coming over and I’m going to have a meeting.” Harry lived off his money’s interests’ interest. He’s extremely financially wealthy. What happened was he set up a flip chart in his room and was buying a whole bunch of land and he was going to subdivide it into a big development. He was using other people’s money. He had a banker, a lawyer, and an insurance person. He had all these different people all around him as his advisory council to help facilitate the projects.

He let you in to watch.

I was way over my head. I didn’t understand anything they were talking about that night. At the end, Harry said to me, “My friend, what’d you think of this?” I said, “It was cool, but I don’t understand any of this stuff.” Harry said to me, “You don’t have to. It’s not about the how, it’s about the who. You don’t have to know how to do all this stuff. You have to know the who, who’s on your team who can help you facilitate to do all this.”

It’s not about the how; it's about the who. You don't have to know how to do all this stuff. You just have to know who's on your team and who can help you facilitate all this. Click To Tweet

Did you decide to go meet with him before or after he showed you this vacant lot?

This is my first meeting with him outside of selling the watermelons on the side of the road. We built a relationship over a few months. One day, he said to me, “Would you be willing to come with me?” I went with him in his Lincoln Town Car and he had a phone inside of his vehicle, the big brick phone with the antenna. It was like $3 a minute. It was expensive. I’d never met anybody who had a phone inside of their car. That was something like Star Trek or out of a movie.

Why do you think he said yes to you?

I think it’s my ambition, my determination, and my perseverance. I was a sponge and curious to learn. I reminded him a lot when he was younger, the ambition, the energy, and the enthusiasm to want to make a difference and change. I learned now from being around a lot of very influential wealthy people that a lot of people get around, people who are much older, for their energy, history, experience, and wisdom. You get around people who are younger than you for their creativity, imagination and their energy.

Fast forwarding in your career a little bit, you were a telemarketer. You were one of the best telemarketers in all of Canada.

I used to make 400 cold calls a day, 2,000 cold calls a week, and had a 98% rejection rate.

Most people wouldn’t be able to handle that kind of rejection.

It was a turnstile of people coming in and some people would last two hours on a shift and they’d be off the floor.

It’s an unfair advantage in sales to have that switch that you can turn off. How did you turn it off and not fear rejection?

I talked to Amir. I got trained to always speak to Amir. Imagine there’s a person in front of you’re talking to them. The first few weeks was brutal, but I needed the paycheck. After a while, you develop thick skin. I developed thick skin. It was like fishing. You hook the fish and you got to fight with it and play with it for a while.

You reframed it into something fun.

We did a lot of role-playing. It was scripted. We read scripts in the telemarketing firm. I was selling magazines across Canada between 5:00 and 9:00 PM, Monday to Friday. After seven months, my boss came and said, “You can’t go any further here. I suggest you leave.” I’m like, “I need the paycheck.”

That’s what I was going to ask you. Correct me if I’m wrong, but your boss was like, “You should quit. You should move on.” Why would a guy tell his best salesman to go quit?

He knew it was a dead end for me and he saw more potential in me than I saw in myself. He also believed more me than I believed in myself. His name was Glenn. He saw more potential in me. When I left, my last day, I went to these telephone stores to actually get telephone books. I bought a Meridian telephone and we would pre-program the last two numbers. If your number was 773-01234, you would dial the last numbers. I started to make 400 cold calls a day from alphabet A all the way to Z through the telephone books. I was calling businesses to see if I could sell them corporate training services to come in and train their staff on how to grow and build a company.

That’s what you did after you left being an employee of that job. I’m assuming you had some savings saved up.

No, not much. I did side jobs a lot of times, side hustles to help pay the bills.

You became a business owner at that point. You’re like, “I’m going to do corporate training because I know how to sell.”

It was from 1995 to the year 2000. I made over 100,000 cold calls over that five-year period. Some months, I was 2, 3, 4, sometimes even 5 months of a stretch behind on my bills, calling the telephone company, calling my bill collector people to renegotiate, “I’m going to get this turned around. Believe in me. I’m making all these phone calls. I can prove it. I’m in the game. I’m hustling, I’m grinding. I’m not sitting on the couch watching TV. I’m in the game and I’m getting rejected.” That showed that I was creating activity. I was taking action lots.

You weren’t known.

Nobody knew me.

You’re having to sell somebody on bringing you in. You’re having to sell your track record and what you’ve done and get them to pay you to coach their team.

The first company who was ever paid me was Investors Group Financial Services. The second company was Century 21 real estate. It was the first two companies that ever paid me. The first payment I got was $50 as a keynote speaker.

What did you do? Did you speak for an hour?

I was speaking for 45 minutes to a group of financial advisors or financial planners.

How’d that go?

It was phenomenal because I was speaking on overcoming adversities, failures, and challenges, which I was rejected a lot, so I had a lot of practical experience in doing that. These are financial planners, financial advisors going out, networking, and prospecting to get clients to sell financial services and products. That led into other opportunities. I got a big break a few years later. I met a gentleman at Stanford University who actually introduced me to somebody. They had a summer program called SuperCamp, SuperCamp.com. I got invited to come down and be a facilitator and a team leader there. I went down there and I worked with a lot of very affluent kids from all over the world at this program at Stanford University.

I got a chance to meet the students and the parents. That opened some doors up for me as well. I got invited from Stanford to go to Singapore and work with SuperCamp over in Singapore. I met some very influential people over there. I was a person who was always knocking on doors, always making phone calls, and always talking to people. People used to always say to me, “You talk to everybody.” I always believed as a young kid that we’re a network of conversations. The more conversations you have, the more opportunities live inside the conversations.

It seems to have worked out well because you became one of the top corporate trainers in the world. You were traveling 300 days out of the year.

It was 276 days a year. I traveled about 300,000 miles a year. I trained 157 of the Fortune 500 companies.

Did you have a spouse or partner?

No. I was single most of the time because I was on the road 276 days a year.

It’s hard to have relationships.

Hard for stability and structure with that. Three weeks a month, I was somewhere in the world. I had so many mileage from hotels, rental cars, and airlines. I would pick people up. It’s like, “Do you want to go someplace in the world?” I had so many miles that they could come with me and everything was taken care of. I sometimes paid the taxes. It was very minimal. I could fly anywhere in the world. I traveled all over the world, doing 50 countries.

You have so many great stories about getting to the next level and overcoming objections. One of my favorite stories about you that you told me when we were in Sarasota one time is the understanding that you could charge more for your services. It was the guy that told you to reach down and grab your balls and double your rate when you were on the phone. Tell that story.

I was in Edmonton, Alberta, Canada at the Crown Plaza Hotel. I was speaking to a group of people in the oil and gas industry for Western Canada. I was one of the guest speakers. A guy noticed me there. He was an executive in a large oil company in North America here, a very well-known oil company. He saw me as a guest speaker. He was one of these guys who doesn’t sit still to listen to somebody. He doesn’t have the attention span.

He got sent there by his employers. He led a whole team of people. He was there as the leader and he found himself bored at these workshops and seminars all the time. He said when I was speaking, he was leaning forward, taking notes, and asking people for a pen. It was out of character for him. He is like, “If this guy can have such an impact on me to have me taking notes when I don’t pay attention to this stuff and actually write things down, then what can he do for my team?” He got a bonus from it based on production. He got salary plus bonus. It was interesting.

What happened was I was in a place called Kelowna, British Columbia, Canada. I was flat broke financially, up and down all the time. A friend of mine called me up and he said, “I want to bring you to this mastermind program.” I said, “I don’t know. What are we going to do?” He goes, “Come as a guest.” I come as a guest. I go in there. There are all these successful people, like a board of advisors like VA. I’m the brokest guy in the group. I don’t have the confidence because I’m putting these people on a pedestal and put myself in the pit. I’m thinking, “I’m not good enough. I’m not smart enough.”

I’m in this room, and they have a thing towards the last half hour to an hour of this mastermind called The Hot Seat. They invite one of the members of the group to come up. You sit in the hot seat and they inspect you. They inspect how your relationship’s going, your health, your finances, your job, career, and business. They pull apart what you’re doing and find ways to contribute, level over you, and serve you. It’s uncomfortable because we all have blind spots.

I’m in the room as a guest and the guy said, “Let’s have Darren Jacklin go up there.” “No, I’m just a guest. I’m not paying to be here. I’m a fly on the wall.” “No, that’s fine.” The guy’s like, “No, go up in the hot seat.” I said, “No, that’s fine.” How am I going to contribute to this group? These guys are so far down the path, further ahead of me than me. I’m here to watch. I’m learning lots, but I’m not going to participate.

The guy’s like, “No, go up.” I get in this argument with this guy, then there are 3 or 4 people arguing with me to go to the front of the room. One guy stands up in front of the group. He goes, “Are you going to keep arguing for your limitations or are you going to go to the front of the room? I’m not going to fight you for your limitations. Get to the front of the room.”

I go to the front of the room and they start inspecting me. The guy goes, “Let me ask you a question. What do you do?” I said, “I’m a corporate trainer.” He goes, “How much do you make a day?” I said, “I get paid $200 a day plus my travel expenses.” “How long do you want to live that way for?” I’m like, “I’d like to get to $500 a day,” because sometimes it takes a day to fly to New York and then I do a whole day of training. It’s $200 and I fly back. It’s actually 3 days to make $200. I can make more money as a greeter at Walmart some days, but I love doing this.

They start picking me apart and inspecting me. The guy goes, “Next month, when we come back, I want you to come back here. I’m going to give you a challenge. You want a challenge? You seem like an overachiever. I want you to start charging $10,000 a day for your corporate training services.” I’m thinking, “No, that isn’t going to work.”

I’m getting rejected at $200 a day. I have a high reject rate at $200 a day. If I ask for $10,000, I’m going to be completely rejected. I’m going to be sitting on somebody’s couch. It isn’t going to work. That’s not possible. This guy starts telling me, “You need to charge $10,000 today.” I said, “That’s not going to work. You have to understand.” “You don’t know what you’re talking about.” I said, “I do know what I’m talking about because I’m making the phone calls every day. I’m making 400 cold calls a day, 2,000 cold calls a week.”

You got the data.

I said, “I know from experience because I’m the one making the phone calls.” I get in this argument with these guys and it’s quite entertaining to some people, but I’m very passionate. I know my industry. The guy says, “Do you accept my challenge?” I said, “Fine, I’ll accept your challenge, but I’ll tell you right now, it’s not going to work. I’m going to prove you it’s not going to work.” He says, “We’ll see.” This is on a Tuesday. Two days later, I get a telephone call from this executive that I met eighteen months prior at the oil and gas conference in Emmett, Alberta, Canada.

He calls me up and he goes, “Can I speak to Darren Jacklin, please?” I said, “Yes, Darren Jacklin.” He goes, “I want to bring you in as a corporate trainer for offsite, which means we go offsite. I want to meet in the Canadian Rockies at the Quantum Leaps Lodge near Golden, British Columbia, Canada. Here are the dates. It’s four months from now. I want to bring you in.” Just to back up, I’m in this mastermind program. They told me that if I’m on the phone dialing for dollars or dialing for companies, if I go to say $10,000 and if I get uncomfortable, I reach down and grab my balls.

It’s to give you a little pain.

Pain or pleasure. I give my word. My integrity is important. I give my word to do this. Two days later, I get this phone call from this executive, from this oil and gas company. He calls me. I thought it was totally set up. I thought, “I know where this is going.” These guys have phoned a couple of buddies of theirs. They got me. They’re calling me. There’s a total setup to see if I fall through my word and be accountable and responsible for my word. I’m thinking, “Okay.”

The guy goes, “How much for a day at corporate training on this offsite?” I paused and thought, “You have got to be kidding me.” I reached down for real. I started grabbing and squeezing my balls. I say, “$10,000.” He goes, “Done. I’ll have my executive assistant call you back in a couple of hours. We’ll get you a FedEx tracking number. We’ll send you 50% of the check and when you train, we’ll give you another 50% plus we’ll pay for your travel expenses.” A couple hours later, I’m thinking, “Is this executive assistant going to contact me?”

She calls me, wants a mailing address for FedEx to send a check for $5,000. What happened was I was behind on my bills and that $5,000, I had to pay people I’d borrowed money from over the last while I was out of integrity because I had over promised and underdelivered. She called me, got my address, and gave me a FedEx tracking number because they had prepaid envelopes with the company. I’m like, “I can’t wait to go to FedEx tonight and see the tracking thing online and see if it’s going to get delivered tomorrow.”

I start calling these people up and say, “I want to let you know I’ve got some money coming in. I’m going to have it in the next day or so. I’m going to pop by and deliver them,” because I always felt I owed money to top buy and give it in person. Not send a check in the mail, but deliver it in person, look the person in the eye, apologize, be integral, sincerely recommit to my promise, and then pay them.

If you owe people money, give it in person. Don’t send a check in the mail. Click To Tweet

What happened was I poured this money. I called all these people. The next day, FedEx arrives. I run to the FedEx truck. I grab the check. I run to the bank. I’m living in Canada. It was a Canadian check at the time, but it was out of province. I go to the bank. I went to see the teller, and I gave her the check. She deposits it. She goes, “Is there anything else I can do for you?” I said, “Yes, I’d like to make a withdrawal. I have to withdraw the $5,000. I still have to pay taxes on it. I’d like to pull a little money aside for taxes in a tax account, but I got to take the money.”

She goes, “Mr. Jacklin, we have a five-day business hold on your check.” I’m like, “I need the money. Can I speak to the manager?” The manager was like, “This is an out-of-province check. You’ve never cashed a check like this of $5,000,” because remember, I’m charging $200. I’ve never cashed a check for $5,000 before. They said, “No, that’s our policy. Five-day business hold.” I have to wait seven days because of the weekend. I called these people up and said, “I’ve got to wait a whole week here before I pay you.” What happened was I ended up getting that all sorted out and straightened out. Four months later, I arrived at the Quantum Leaps Lodge in Golden, British Columbia, Canada, in the Canadian Rockies. I go to this corporate training seminar. Phenomenal event.

There are about twelve participants there. Very phenomenal. They do an evaluation form. They score me very highly. At the end, they go whitewater rafting down the Canadian Rockies. This executive says to me, “You and I got to go for a walk.” This guy smokes about 1 to 2 packs of cigarettes a day. He’s got his Players Light cigarettes there in his pouch. He’s got a cigarette in his mouth. One after another, he is smoking cigarettes.

You thought he might be mad.

I thought he was upset with me. Real redneck guy. We go for a walk down the riverbank and he goes to me smoking a cigarette. He’s got my check for $5,000 behind his pack of cigarettes. He says to me, “I got a question to ask you. When I asked you four months ago, when I called you up and I asked you how much for a day at corporate, why’d you tell me $10,000?” I’m thinking, “I hope he doesn’t try to get a refund because I’ve already spent the money.” The $5,000 that I got as a deposit is already spent and the other $5,000 that he’s got his check, that’s already committed. I’m like a duck. I’m nice and calm and proper, but underneath, I’m pounding fast, but I’m scared.

This guy looks like a violent guy if he gets upset. Real redneck guy, oil patch worker. I said, “I think I did a phenomenal job. Your team was very impressed. We got evaluation sheets. I scored highly on that. I looked at it briefly before I went up with you.” He goes, “Can I give you some feedback? The next time somebody asks you how much for a day for your corporate training services, you don’t open your mouth and tell the price. Otherwise, you’re going to negotiate with yourself. You need to ask what people are willing to pay.”

“Darren, I had a $25,000 budget set aside for you. I was going to pay you $25,000 for the day plus first-class travel expenses to come here and train my team because I know what you did to me in my life eighteen months ago. If you can make an impression like that to me on my life, what can you do with my staff and my executives? You have $15,000 on the table.” He hands me a check and he goes, “I hope you learn your lesson today on this. Let’s go back to camp and have a campfire.” He handed me the $5,000 check. He believed more than me than I believed in myself that he was willing to pay me $25,000 for a six-hour corporate training seminar. Four months earlier, I was getting paid $200 a day.

Did you change everything from that point on?

I realized that when I charge $200 to $500 a day, I deal 4, 5, 6 or 8 people who want to interview from a company. When I started charging corporations $25,000 for a day, the most I’ve ever been paid is $40,000 for a day of corporate training. People say $40,000. If you’re helping a company with an acquisition, a merger, and they’re making hundreds of thousands of millions of dollars, $40,000 is chicken feed.

You have to understand the mindset of that. People are like, “Why would they come here for $40,000 for a day?” It’s because of the return on investment of how they monetize in my training development material. Sometimes I need introduce them to somebody through my network and that one connection be worth millions of dollars to them, buy their company, invest in their company, and become an executive with their company or something. It was all based on that.

It’s not the training. It was the relationship with Darren, that network. That’s what it was worth.

That changed my life. I did go the next couple of months to the mastermind, but later that fall, I went to the mastermind where the guys challenged me. I went in and I actually went to Staples and took pictures. I got photocopied of the checks to verify that I actually got paid $10,000. I shared the story to the mastermind group, which inspired the people. They’re like, “We told this guy to ask for $10,000 and here’s this guy in an oil and gas company telling him to charge $25,000.” My mindset was how to get from $200 to $500. That was a stretch goal for me. I never imagined in my lifetime ever being paid $25,000 in a day. Maybe in a few months or six months, but never in one day of corporate training.

The watermelon farmer and these corporate trainers, the mastermind, your boss at the telemarketing company, your friend who encouraged you to summit Mount Kilimanjaro, everybody sees more in you than you see in yourself. From experience, how would you advise somebody who might be struggling with that or doesn’t even know that they’re struggling with it?


Cocktails and Dreams Real Estate Podcast | Darren Jacklin | $100M Dollars


The key thing is your environment. A lot of times, I would spend time with people I respect and admire, not people I always have an influence on. You want to get around people who you respect and admire, the people who always have influence. We become comfortable in our environments. If people are living paycheck to paycheck, typically, your environment or the people around you are all paycheck to paycheck.

I was overweight, so I was hanging with people who were overweight. I was hanging around people who didn’t exercise. I was talking to my environment. As soon as I started to hike more, I started to be around other hikers. As soon as I started investing in real estate, I started getting around the people. As soon as I started being on boards of directors, I started getting around with the people who were on boards of directors.

The thing is birds of the same feather flock together, as they say. I started to realize that my environment is stronger than my willpower. To somebody who’s struggling now, the key thing is to get around other people who are more successful than you. Two things happen. Number one is the knowledge transfer. Number two is an energy transfer. For example, as we’re here now, if Warren Buffet walked by here now and all he did is looked at you and nodded his head or said hello to you, would that have an impact on your life? How long would it stay with you for that impact?

Probably the rest of my life. I would tell many people about that story.

It’s the energy. One of the things about masterminding is that people always say it is like Rotary Clubs, Chamber of Commerce, Women of Business, private mastermind groups, or sacred societies, whatever you want to call it. Different clubs, different groups country clubs, tennis clubs, private clubs you get involved with, why do people join those clubs? You might feel like you’re failing in your marriage, your finances, your health, or your business, but if you get around people who are succeeding, some of that will rub off on you. Successful people get together because energetically, there’s a transfer of energy and a transfer of knowledge. That’s the key thing. The masses think everything’s a scam. Successful people think there’s an opportunity.

If you get around people who are succeeding, some of that will rub off on you. Successful people get together because there's a transfer of energy and knowledge. Click To Tweet

The thing is most people are not successful in the biz life. They watch television, watch the media, or they go drinking or party, something like that. They do things like that, which are low vibrational things. You’ll find people, whether it’s real estate, pick any industry. One thing that is at the top of my mind, I would be speaking at conference. I have trained over 1 million people and I’d be a guest speaker at a real estate conference with 5,000 or 10,000 people in the audience.

The first three rows are your top incomers, your top achievers. I’d watch people in the back who are struggling. I think to myself, “If I was in the back, I would want to find out what the person the first three rows is doing and if I could go for breakfast, lunch, or dinner with that person.” I’ll give you an example. If we took a group of 10 people, this person’s a ten-aire, a hundred-aire, a thousand-aire, half a millionaire, a millionaire, multimillionaire, deca-millionaire, and then a billionaire, if you had a chance to anybody out for lunch, who would you take out for lunch?


Most people will not take a billionaire out for lunch.

Why not?

It’s because they’re intimidated by him or her. They will go to work on a level based on their net worth. If I’m making $60,000 a year, I’ll get somebody around $60,000, $70,000, $80,000 a year.

I would say most billionaires probably wouldn’t go out to lunch with people because they want to network with other billionaires. This happened to me at Tony Robbins event. I was at the point where I put the $10,000 fee for all of Tony Robbins’ live events on a credit card, believing that I knew I could pay it back with what I would learn. As you were talking about, I showed up. I was the low man on the totem pole. I couldn’t afford to be there. I was trying to learn the best I could to get to the next phase of my life. There were people sniffing people with money to go network. I’ve never felt so rejected in my life from people that would ask me 2 or 3 questions. No. “Do you have money? Can I network with you?” “No.” How would you challenge me to say that?

I have different circles of people that I’m around billionaires all the time on a frequent basis. In fact, I’ve been around three of them, being here at this conference in Las Vegas. I hike with billionaires. In fact, some of the people, if you were around following me, there’s people around me that you would never even know they’re high net worth, ultra-high net worth, or billionaire level. They blend in like everybody else because they don’t want the visibility. They don’t want the exposure. They’re low profile but high impact.

Those people would go out to lunch with you.

They are because, to them, they realize it’s about paying it forward and passing it on because they were wanting your seat. The people I’m around are first or second-generation, but they had to work for it. They didn’t inherit the money. They’re not trust fund people. I have some trust fund people in my network. They’re a little bit different. Some of them are entitled. Some of them are more drama, more problems and challenges go on their life. The thing is that all it is is about making a request.

I always give people an assignment or an exercise. I always give them two questions. First of all, if we look at life, we are all a network of conversations. The more conversations we have with people, the more opportunities live inside of conversations because all we are is a network of conversations. What I encourage you to do is to make requests. Now, there’s a request. There’s a powerful request, there’s an outrageous request. There’s an unreasonable request. You make a request. For every request you don’t make or every question that you don’t ask, the answer’s always what?


When you make a request, only 1 of 3 steps will happen. Step number one is people will accept their request. Step number two is they’ll decline the request. Step number three is they’ll do a counteroffer to the request. They’ll accept, decline, or counteroffer. I share with people to practice doing this through a network of conversations. Practice making requests with people.

The more you to do it, the more you develop a muscle, a pattern of consistency of doing this and you’ll get better and better at it. Eventually, it becomes autopilot. You start making requests for everything. “Can I make a request?” The thing is, what I encourage you to do, question number one is, where am I not requesting in my life? You actually write this down. You take a look at your life like an audit. You actually audit your life, “Where am I not requesting my life?” You look at your life of where you are not requesting. Where you’re not requesting, it’s an area of your life that’s not growth.

For example, you say, “I want to make a lot more money. I want to change my ZIP code or my postal code. I want to travel more. I want to take more trips. I want to send my kids to private school. I’ll put my kids in college or university. I want to have a nicer vehicle. I want to change my wardrobe,” whatever it is. If you start having more conversations, get around people who are financial people, investors, or people who are good at managing or got their money, your finances will change. If somebody’s not a millionaire, I put around four millionaires and they hang around. If you hang out with four broke people, you become the fifth.

I was raised to be a gentleman and to value people’s time. A lot of times, if I don’t have anything valuable to offer, I won’t ask or make any requests because I’m trying to be humble.

Here’s the thing. We all think that we don’t have anything to contribute. It might even be your presence, just you showing up. That is an exchange of energy. There’s a knowledge transfer and an energy transfer. You might have a skill. That could be barbecuing or it could be cooking.

I actually do have that skill. I love it.

It could be the way you connect with your son, your daughter, or your wife that this billionaire or high net worth alternative person does not have in his or her life. Every person has something that can contribute to another person’s human life. Remember this. You guys are having a conversation not by accident. I believe that everybody is by design. Everybody comes in your life on purpose. I can go to the other side of the world and, all of a sudden, I meet somebody who knows somebody where I live. It’s a small world. I think it’s always on purpose. If nothing’s ever in your way, it’s on your way.


Cocktails and Dreams Real Estate Podcast | Darren Jacklin | $100M Dollars


You look at through the exploration process of having a conversation of talking to this person because a lot of times, when you meet somebody who’s successful, you put them on a pedestal. You put yourself in the pit and you think, “Who am I?” Realize that this person has fears, doubts, worries, and insecurities. They’re like you and I. They’re no different. They are good in a certain area of their life. It could be finances or business, but they have another area in which they’re not so good. I’ll give you an example.

A lot of times, you meet somebody who's really successful. You put them on a pedestal and put yourself in the pit, not realizing that this person has fears, doubts, worries, and insecurities. They're just like you and me. They're no different. Click To Tweet

Years ago, there was this very wealthy man. He sold this company to Cisco. He owned a company. It was a food supply company. He sold it for millions of dollars to this company. I went to a Rotary Club meeting one time. This is many years ago. I wanted to meet this guy. I walked into this Rotary Club as a guest speaker. A friend of mine who’s passed away now owned a whole bunch of restaurants. He brought me to this Rotary Club. This guy come and he sat down. His name is Bill. I wanted to meet this guy. He blew me off. There was a 30-year age gap between my age and his age. He wasn’t there for me. He didn’t give me the time of day. I was offended by it.

He’s sitting there and he’s talking to my buddy, Reg Henry, who’s passed away now as well. He is like, “Reg, I’m doing this party this weekend for all these vendors and all these food suppliers. They’re all coming to the house. We got this conference and we’re going to have a pool party. The other day, my grounds man was smoking marijuana and I fired him. I don’t want guys like that on my property. They’re going to be smoking marijuana. I fired the guy. I had nobody to cut my grass.”

“Now my wife wants me to cut the grass. I don’t even own a lawnmower. I don’t even know how to cut grass. I never cut grass in years. I wish somebody could solved that problem for me and cut my grass.” I told Reg that this guy wouldn’t give it the time of day, but Reg knew me very well. I said, “Reg, I’ll cut his grass.” Reg goes, “I got somebody for you, Bill.”

He said, “Good. Here, have him pop by my address. Be there by 9:00 on Saturday morning because the pool party starts at 4:00 and all the crew are coming in at 1:00 to start setting up”. I go borrowed somebody’s lawnmower. I show up at his house. Here’s what I did. I actually brought my clothes for the night because I thought, “If I’m going to be in this room, I’m not leaving.” When I got there to cut the grass, I cut the grass. I cleaned the swimming pool as well. I spent time building relationship with his wife because he wouldn’t give me the time of day. His wife got to know me, like me, and trust me in a very short period of time. She’s giving me lemonade. She made me a toast of tomato and lettuce sandwich.

She goes, “By the way, are you staying for the party tonight?” I said, “Yes.” She goes, “The changing room’s over here by the pool party.” I go and I change because it’s like in business. If you’re in the room, be in the deal. The guy, a very wealthy man, told me that years ago. He said, “If you’re getting a seat at the table, make sure you’re in the opportunity, whatever it is.” That was a big thing for me. I go to this party that night and Bill comes up to me. He goes, “You look familiar.” I said, “I met you recently at the Rotary Club.” He says, “How did you get here?”

I said, “Your wife and I’m good friends with Reg Henry.” “Okay,” and he walks off. A while later, what happened was I was consistent. I realized several months later that he was testing me. He saw me as a young guy. He’s like, “Is this guy going to be focused? Is he going to be committed? Is he going to be disciplined or is he one of these guys that’s going to be all over the place?” He does this with people as his personality to test you to see if you’re consistent. He’s the type of guy that will come in like this.

Let’s say you’re selling him advertising. He’ll say, “Jeramie, you’re ripping me off.” All he wants to see is whether you are going to back off or push back? He wants to see what you’re made of, your character. He’s one of these guys. Once you get to know him, the guard comes off and he’s joking around with you. He’s got a good sense of humor and he is totally fine. Those first few months, it was tough. I was scared to be around this guy. He was so intimidating. I thought it was aggressive and arrogant. After I realized it was an act that he was trying to test me to see what I was made of, I hung in there.

There are two more things I want to touch on. I want to touch on your book and I want to touch on the profit, the new opportunity that you’ve got. Before I do, I wanted to thank you for one of our conversations in Sarasota. Although I do believe I have this mission, I’ve always been somebody who sows into people. I’ve always believed that you reap what you sow. I’ve always put other people first and I’ve always participated in business ventures where I believe I’m serving people. That’s always come naturally to me. I had a block when it comes to money or financial gain because I’ve had a few great years. I’ve got more money than I’ve ever had in my entire life.

During COVID, I paid off everything that I own, including my house, which was a huge deal for me. I felt like I’m good. I don’t want anything else, but there are still things that I want to do. That requires resources. I got to a point where I didn’t know how to want for more because I felt bad wanting more. In the conversation over dinner that we had in Sarasota, you introduced me to your quote, which is also in your book. “Your success is somebody else’s miracle.”

My success is somebody else's miracle. Click To Tweet

That changed me. It totally changed me because it reframed the rest of my life. Now I know I have to succeed because, if I don’t, other people won’t have the opportunities. We hear from a lot of different people that money magnifies who you are. I’m a very generous person. I want to be generous. In times of financial stress, I get very upset. I get tearful when talking to my wife because I want to give more. I want to do more for people.

You and I are very similar in that area. I always want to make a difference.

There are transactional relationships in your life and there’s transformational.

I don’t want to see people struggle. It hurts me. It pains me to see people struggle. Yet, I see some people in business when they’re struggling, I know they’re so close to a breakthrough. I don’t like seeing people not having food in this world or not knowing where the next meal will come from because I’ve been there.

I have a limiting belief that there’s no money in transformational relationships. Tony Robinson might tell me otherwise. There’s a lot of transactional relationships before you get to the transformational ones. I want to thank you for that quote and that reframing. People should read your book. The Elevate 2 Educate foundation that you and Tatiana do is very beautiful.

I love that if somebody wants to talk or work with you, they have to walk with you. They’ve got to believe in what you believe in. Your story about going to Africa and seeing a young lady sold for a dollar changed you and Tatiana. You’re doing things to stop human trafficking with your foundation. It’s amazing. I want to do more to participate with that. You challenged me to find something I could live the rest of my life for.

Dedicate your life to a cause greater than yourself.

That will propel me and other people, and it’s probably happened for you too, to higher levels of success and financial gains because you have a good reason to do it.

It’s never about you. You’re just the messenger of the message. You’re the vehicle to facilitate it, to dedicate your life to a cause greater than yourself. I remember one of my mentors in the book, Harry, the guy with the Lincoln Town Car. I sat with him on a park bench one time and I saw him open up an old leather briefcase and write out checks for up to $100,000 anonymously with a numbered company using the city hall as a return mailing address on the envelopes with the stamp.

We sent out a $100,000 in checks that day with a numbered company that was non-traceable. He’d structured set up giving anonymously to people. I made a promise on that day not to ever say where those checks got distributed throughout the community. He said to me, “I want you to someday be in a position to be able to do this.” I saw him write a check one time for $1 million to a charity of his choice. He says, “It’s one thing to make $1 million. Now make it and give it away.” That’s a whole other level. “I made $1 million. Give $1 million away to a cause of your choice.”

How can people get a copy of your book?

The book is Until I Become. They can go to they can go to either Amazon if they have an Amazon account or you can go to UntilIBecome.com or google the website and the name of book. It’ll come up on various different book stores all over the world.

It’s very practical and very easy to read. With my book, I joked that I wrote it at a fourth-grade level because that was the only level I could actually write at. My book’s very easy to read, but yours is incredibly impactful. It’s intelligent. I wanted to leave people with what’s next. What’s next for you? It seems to be you’re going to innovate again. You and Carl Gould, your business partner, and Tatiana. Talk to us about your new opportunity.

I was around the real estate environment for many years, serving as board of directors, but also 25 years doing corporate training. Let’s say 35 years, technically, of being around the real estate industry, 57% of real estate agents don’t pay their income tax on time. I also see that we have an aging population of people in North America. I always look at disruptive business models like we’ve done with eXp. I would say, “What’s the next thing to disrupt certain things?”

If we look at the accounting and bookkeeping industry, it’s a boring industry. It’s a regulated industry. You have to go to school to get a designation to become a CPA or a Charter Professional Accountant. Now, the average CPA in North America is 61 years of age. Him or her, they’re a Baby Boomer. Between now and the year 2030, over 100,000 licensed CPAs are going to retire and exit as Baby Boomers. They have a book of business. They have an accounting firm practice or booking practice that they’ve built up for over several years, some even decades.

There’s value there and those customers don’t want change.

The data shows in North America that the average business person will stay with an accountant for seventeen years. That’s the average life of a client. They got all the data and that’s pretty good. Low attrition rate. The thing is, with the accounting and bookkeeping industry, it’s an industry where accountants don’t like change. Being an entrepreneur, being someone who sees opportunities, I thought with my partner, “Why don’t we go and raise private money, a pool of capital, pay investors 12% annual return over one-year term, and then let’s go start to acquire these accounting bookkeeping firms that are off-market deals through my network of other CPAs?” I’ve got some friends of mine across North America who are CPAs who love numbers and love people, but they’re extroverts.

They’re not your traditional reserve analytical accountant account. They love people, but they love numbers. They go to a lot of networking events and a lot of accounting, bookkeeping, trade shows, conferences, and workshops in North America. They’re always networking with the accountants, finding out who’s going to retire or who’s going to sell their firm or their practice.

We get lead sourced to us of off-market deals because there’s a commission or an affiliate referral fee being paid to these people. One firm we’re actually closing on, the CPA who referred to us, for about 3 to 4 hours of work, he’ll make $20,000 commission. He’s a numbers guy. He is thinking, “I can go out and get all these clients and do all this billable work for my clients, but I can make $20,000 just networking at trade show associations, then source them to Darren, Carl, and Tatiana.”

We’re building a $50 million company. Here’s the thing. It’s easier to acquire revenue than to actually go out and create revenue. For us to build a $50 million revenue company with monthly recurring revenue, it’s easier to go out and acquire all these accounting firms or booking firms and roll them up into one platform and grow and scale it instead of grassroots it.

Imagine how many conversations we’d have to have in trade shows, network events, and social media ads we’d have to run to have a billable time of $50 million. How many clients? It’s easy to acquire revenue than to create revenue. That’s what we’re doing now with profit. We’re building this up. We’ll keep it about 3 to 5 years and then we’ll probably sell it to 1 of the big 4 accounting firms or one of the private equity firms.

We’ll go through what we call a liquidity event. We’ll cash out and put money aside for our taxes, and then the rest of the money will be put into income-producing assets to bless and serve more people. We’ll start something else after we exit that. We’ve built it with the end in mind to exit but to solve a problem for the accountants and bookkeepers. Some of them will stay on with us. Some of them have no energy and they want to exit in their sunset time. We bring them in, we keep the jobs, we keep the people, and we make a difference. The cool thing about it is that it doesn’t matter what the economy’s doing. It doesn’t matter what the weather’s doing. The thing is you got to pay your taxes. It’s something you can’t avoid.

Is there anything else you want to share with anybody?

The biggest thing with things in life is that we’re either coming from a problem, we’re in a problem, or we’re heading towards a problem. Every human being on the planet goes through that. Realize that no matter where you’re at now, if you’re thriving or struggling in your life, it’s a season. If you look at life as being like the four seasons, you might be in wintertime now. If things are not going the way you want them to go in your relationship, health, spiritual life, finances, job, career, and business, you’re in a winter time now. Some people are in a long winter cycle, but spring will come.

The way to get out of that and get into spring is through a network of conversations. Don’t hold anything so close to yourself. Put some cards on the table and have an authentic and vulnerable conversation. Ask for help, “I’m struggling this area in my life now. Can somebody help me?” Sometimes people have to go away from their family or away from their environment because those people are going to judge them, laugh at them, and make fun of them. Step out of that environment into a different environment that’s supportive, encouraging, and collaborative. It could be at your church, online, a Facebook community, LinkedIn, or some other group of people you get around. Start to have an authentic, vulnerable conversation about what’s going on.

Just like people who’ve been to AA or Narcotics Anonymous and all this, the hardest thing is walking through the door. I can remember when I was in Dale Carnegie and Toastmasters, the hardest thing for me was walking through the door because when I got on the other side of the door, I realized that everybody was afraid of public speaking. They’re there to get trained to develop how to overcome the fear and the courage to actually public speak. Everybody in the room in those chairs all had a fear of public speaking.

I actually went through the Dale Carnegie sales training program. I was an assistant instructor at one time. Dale Carnegie was the first book that I read that changed my life. How to Win Friends and Influence People. I learned a lot in there. One of the things I learned is this. How do you learn to play the guitar? By playing the guitar. If you want to learn to public speak, then get in front of people. They force you to do that. It’s great training. Thank you, Darren, so much for your time. It’s an honor to call you a friend. I want to thank you so much for being a guest on our show and I look forward to our growing relationship.

Thank you so much.


Important Links