Industry Leader Todd Cahill Joins DreamTrips: “I’m Going All In”

According to a recent press release: 

After six years away from direct selling, veteran leader Todd Cahill shares that he has joined DreamTrips, reuniting with DreamTrips owners Mark and Tammy Smith twenty years after they first started building businesses together.

Why DreamTrips. Why Now.

By Todd Cahill

I met Mark Smith in 2005, the year my first child was born. That child is now a junior at Belmont University. Mark’s leadership paid for those years. It fed my family.

He became my mentor. I built two companies under him. In one of them I built a team of more than 100,000 people doing $10 million a month. It held there for years. I was not the reason it worked. I was in my twenties, I was coachable, and I had a leader who knew what he was doing. Give me that same leadership with what I know now, and I think we find out what I am actually capable of.

Then we parted ways. I spent six years building on the B2B side. I did well. But there is very little residual, and you work twice as hard for every dollar. There were stretches where I wondered if the best run of my career was already behind me. I was working harder than ever and building nothing that would still be there if I stopped. That is a quiet kind of tired. If you have ever poured yourself into something that did not last, you know exactly what I mean.

When I learned Mark and Tammy own DreamTrips, I reached out. Then I looked at my own life. In the past twelve months I traveled to eleven countries with my girlfriend. Travel is not a concept to me. It is the thing I want more of, and it is what I want to give my kids.

What sold me.

The market. We are not another product company fighting for shelf space. Travel and tourism contributed $11.6 trillion to the global economy last year. That is nearly one in every ten dollars on earth, and it is growing faster than the economy itself. That is a different game and a bigger one.

The retention. When the product is an experience, you do not cancel it. Once you have been to Prague, or stood in a room with great people at a resort in Mexico, you plan the next trip.

The reach. I helped open Korea years ago, but that was physical product, and product across borders is harder than ever. This is digital. That changes how fast and how far this can go.

The foundation. Mark and Tammy did not start from a whiteboard. They bought a company with roughly five million members and fifteen plus years of relationships with resorts worldwide. Most companies spend a decade trying to build what this one had on day one. What it needs now is leaders to take it global. That is the exact problem I know how to solve.

The timing. I build with AI every day, and DreamTrips being powered by it matters to me. But I also understand human connection. This is the moment those two belong together. Powered by AI. Lived in person.

For years I felt guilty traveling because I needed to work. Now the traveling is the work.

Everything rises and falls on leadership.

I learned that working personally with John Maxwell for years. Not product. Not timing. Not comp plan. Leadership. So when I evaluate an opportunity now, I start with one question. Who can I actually trust?

Mark and Tammy own this company outright. No private equity. No board. That got my attention, but it is not why I said yes. I said yes because I have been in thousands of situations with them. I have watched them do the right thing when it cost them something. I trust them one hundred percent, and at this stage of my life that is the only currency that matters.

What I actually want to build.

The money was never what I missed. I missed developing people. Watching somebody who did not believe they had anything in them stand up in a room a year later and lead. I have been chasing that feeling since I was 23.

So I am not coming back to chase a rank. I am coming back to develop leaders, globally. Leadership events in Scotland. Greece. Australia. Rooms where people get built, in places they will remember for the rest of their lives, with a business that pays for them to be there.

With this foundation, the technology under it, and enough leaders to carry it, I believe we can double this company’s membership in five years. I say that as someone who has been around long enough to be skeptical of that kind of sentence.

What I bring.

24 years full time. Four companies since 2005, and I reached the highest rank in all four. I have been on national television. I am published by Greenleaf. I am an executive producer on a feature film coming out in 2027, and I star in it alongside A-list talent.

In all of that, I have never seen anything like this.

This is the one I am most excited about, because this is a legacy build. I am stepping into a company that has welcomed 5 million members and done close to a billion dollars a year.

None of that matters to you unless it turns into something you can use. So here is what it turns into. The systems, the content engine, the follow up, and a way for a person with a full life and a real job to run this without living on their phone. And content that is simply traveling the world and sharing it. There is no compliance minefield in showing people where you have been. I am not going to hand you a link and wish you well.

My book is called You vs. You. One of the battles in it is You vs. Your Finances. I have never met a person who does not want to travel more. For most, the money is what stands in the way. This is the first thing I have found where you can work on both at the same time.

Who I am looking for.

Not everybody. Professionals. Builders. Parents who want their kids to see the world instead of hear about it. People who got burned before and swore they were done, and still felt something reading this. People who hate the cringe as much as I do.

You do not need to have done this before. You need to be good at something and willing to be coached. That is exactly how I started.

If that is you, come find me. I will answer you myself.

I am putting the personal brand I spent twenty-four years building directly next to DreamTrips. I am going all in alongside Mark, Tammy, and the DreamTrips team. The people who taught me how to run in the first place are the people I am running with again.

If I bring something to you, I have lived it, vetted it, and put my own name on it. My name is on this one.

— Todd Cahill