Jayson Gaignard

Jayson Gaignard is a Canadian entrepreneur, networking specialist, and author who founded MastermindTalks. In 2004, Gaignard founded VIP Services Inc., a Toronto-based full-service concierge company. The company evolved into an online ticket seller and changed its name to Tickets Canada, which generated $5 million in annual sales.

In 2012, Gaignard began curating dinners in Toronto, Canada with small groups of entrepreneurs that focused on relationship building. The invite-only dinners became MastermindTalks—larger conferences for entrepreneurs geared toward health, wealth, self-improvement, and networking. Past MastermindTalks speakers include Tim Ferriss, James Altucher, A. J. Jacobs, Esther Perel, Dave Asprey, Guy Kawasaki, and Marc Ecko. Forbes described Gaignard as one of the top networkers to watch in 2015.

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Jayson Gaignard talks about the darkest moments of his life and how he overcame them as an entrepreneur and as a father. He also shares what it means to live in alignment and why we need to build communities that bring deep connection.


Thank you for being part of this movement, Jayson. I was really excited to have you. When I speak with founders, so many of the conversations are about wanting more support, a sense of community. You were one of the first people that I thought about because you've done so much work in that space.

Tell me more about your journey. What is your story?

Quite simply, I was never much of an academic. Never really fit into the traditional education system and ultimately dropped out of high school.

Initially, I was a mechanic and it was one of those things. I always worked throughout high school, so I was one of the guys with a lot of money. When you live at home and you have a lot of disposable income, generally a lot of people in their teens will pool their money towards having the nice car. I did that for a little bit and realized that really wasn't my calling.

I always felt drawn to entrepreneurship. Like most entrepreneurs, I showed signs of the entrepreneurial bug at a young age, with lawn cutting businesses, snow removal businesses, and all that kind of stuff.

Ultimately, my first business turned out to be a personal concierge firm, where we basically run errands for people. Our slogan was, “If it was legal, moral, and would save you time, we'd take care of it.” We did everything from watering people's trees, to chauffeuring people around, to breaking up with people's girlfriends. I mean, as long as they paid 50 bucks an hour, I'd pretty much do anything. That's the plague of most early-stage entrepreneurs is that they'll try to serve everyone and that was very much what I did in that first business.

I realized early on that service-based businesses are difficult to scale, especially given my skillsets at the time. When people thought of the word “concierge” back in the day, they thought of a hotel concierge. When they thought of a hotel concierge, they often times thought of concert tickets. People started to come to us for concert tickets and we'd store tickets through these big brokers in the city, paying huge, huge fees that we'd have to pass along to the client.

So we started stocking our own little inventory with the hopes of saving our client base some money. Ultimately, just through word of mouth, people kept on coming back and telling their friends. That product side, the e-commerce side, started to eclipse the service-based business that we had before.

We just pivoted into the e-commerce space, and within three years or so, we grew to $7 million dollars a year with no outside investments. I was very inspired by Tim Ferriss' book, The 4-Hour Workweek. At one point, I achieved that model of success where I was traveling the world and making a ton of money.

However, with all that money and all that free time, I started to ask myself questions like, "Why am I here? Will I be remembered? How many people will show up to my funeral?" And I was not happy with the answers I was giving myself. I was climbing up Maslow's hierarchy of needs and I was having a crisis of meaning. I realized that I built the wrong business.

I built a business that I hated, to enable me to buy things that I need, to impress people I didn't like. Although I was in a position where I could've sold the business, it would've required me to stay in that business for another year or two to position it for sale. I just couldn't do it to myself.

When I realized I was out of alignment, I had to get out as soon as possible. The plan was to scale the business down to zero, then I'd have a little bit of money left to start something new.

Unfortunately, things didn't go as planned. It was very much the death of a thousand paper cuts. The minute I decided I didn't want to be a part of the business anymore, I removed myself from it. I'd only check in like once a month. The business, from an internal perspective, just kind of cannibalized, and I didn't really care. I just really wanted out.

Ultimately, getting out I did. After about a year of scaling down, two things happened that were beyond my control. When the dust settled, I was a quarter million dollars in debt, which was August of 2012.

There's a saying that when one door closes, another one opens, but it sucks to be stuck in the hallway. That was a really, really dark hallway for me at the time.

The following month… Everything collapsed in August. September 1st, I got married to my wife. In the Bahamas, in September 1st, my daughter turned six months old. It was definitely a tough transition period, because I no longer had a business, no longer had cash flow. I didn't know what I was going to do next.

In that time of transition and despair, somebody posted on social media they had an extra ticket to go see Seth Godin in New York. I had no other obligations at the time and I had been a big fan of Seth's work for years, so I decided to take her up on the opportunity.

I went to his workshop and the theme was the connection economy and how there's huge value in connecting like-minded individuals. At the time, I felt very, very socially isolated and very alone on some level, so I started these dinners where I'd invite eight entrepreneurs out for dinner with the focus of connecting them.

At first, when I did it, I almost canceled two hours prior. I'm like, "Nobody's going to see value in this. They're going to think I completely wasted their time," but thankfully, that first dinner turned out to be a success. I decided to continue on with these dinners, even though my peers thought I was crazy because I didn't know how I was going to make rent the following month.

The way I rationalized it was that the bank could take my car, but they can't take my relationships. Investing in myself and investing in my relationships were really the safest investment I could make, so I continued on with the dinners. Then I had an opportunity to do an event with a gentleman named Tim Ferriss, who's a multiple-time New York Times best-selling author now, with a big podcast platform. He’s also an award-winning angel investor.

I never thought I'd be in the event space, but I just saw the chance. Instead of having eight people at a dinner, I could have 150 at an event, so it was purely a social capital play. I'm like, "If I can break even and bring 150 amazing people together, that's a huge win for me."

That event is significantly different than a traditional conference. It's much closer to a wedding than anything because I didn't know the traditional rules of doing an event. We did that event in 2013 and we had 4,200 entrepreneurs apply for it.

Since then, we've had 17,000 entrepreneurs apply for MMT, which is capped at 150 people annually. We just wrapped up our event at Park City in September. Our next event in 2019, which is 11 months away [from the time of this recording], is sold out. We've locked down a venue for 2020. We'll be selling that one shortly too.


Amazing. Thank you for sharing your journey. It is a testament to the work you do that many of my friends, who have been to MMT, talk about how it has changed their lives.

You spoke a lot about alignment and connection. What have been some of the most important lessons that you've learned about yourself? About living a life that reflects you?

I mean, listen. When I had started that first business, I did it by just, I guess, playing to the gospel of entrepreneurship where you pick a business based on opportunity and proximity. How can you make the most amount of money as quickly as possible, given your skillset, right? I mean, that's how most of us are taught to figure out what we're going to do from a business perspective.

When I landed in that first business, it was highly profitable, but we were in the event ticketing space. And the funny thing was is that we sold millions of dollars of Leafs tickets every year, but I've never been to a Leafs game. You know what I mean? It's hard to get behind something that you're not, or it's hard to sell something, and that being your life, when it's not an area of passion for you. Ultimately, it became a pain point.

I don't tell too many people this, but those closest to me know that there was opportunities to sell that business on the way down. I saw the business as such a pain point that it caused me to focus on the wrong things. When opportunities came my way, such as friends who wanted to buy the business, I refused to sell it to them. I'm like, "I don't want you to come back to me years down the road saying that this business ruined your life as well."

In contrast, now we serve 150 people at MMT, I'd easily have 135 of them to my wedding. These are my favorite people on the planet. I've been lucky enough to really blur the lines between work and friends and family. My wife is involved in the business and 95% of my social time is with these people. We do a family vacation every year, where 20 or 30 of the families gather. We're doing a Disney cruise in February, and last year, we rented a property in the Bahamas and vacationed together. I'm very, very lucky, and very grateful for what has happened, but it's also been conscious choice.

When I was in that transition period, I knew that I didn't want to end up in the same situation again, I wanted to make sure I climbed the right mountain.

One exercise I did, which turned out to be really powerful, was identifying what my perfect day would look like. The core purpose of business is to make money and the core purpose of money is to perpetuate experiences in your day-to-day life.

If you look at things in that thought process, then the next logical questions are: What do you want that perfect life to look like? What time am I waking up? Who am I waking up next to? Where am I living?

Not clear on the business, but clear on the life that I wanted to lead. When opportunities started to come my way, I could ask myself, "Is this going to take me closer to my perfect day, or is it going to take me further away?" And if it was going to take me further away, then it was easy for me to say no.

I wouldn't want to start a tech startup, because that would take me the long hours, and that kind of stuff would take me further away from my perfect day. But ultimately, the career path I've chosen with MastermindTalks is ... It's like, I did that exercise five years ago and I'm about 95% towards what I said.


Kudos to you for hitting 95% for your perfect day. That’s a testament to how you’ve been creating the things that you've actually want. Here's something that I'm curious about: the stories we tell ourselves about success.

What would you advise to people who are in that place where their business or their life is not really for them? How can they make the transition?

Yeah, there's no magic bullet or no single path. Whatever that passion is, that's what you need to pursue. Some people will use a company as a vehicle to create freedom in their lives, so that they can pursue their passion unapologetically.

I'll give an example: Arnold Schwarzenegger. He wanted to get into films, but they had all these weird roles. Ultimately, he became a millionaire in real estate first. Why that worked to his benefit was when he was given roles that weren't in alignment with what he truly wanted, he could walk away because he had the financial means to do so.

For me, all I know is that when I'm not alignment, you can feel it. You can feel it from the minute you wake up to the minute you go to bed, That, to me, is a feeling I can't sit with. I simply can't.

When I was mechanic, what made me leave my job was looking at one of the business owners. He was working on a car and he was only in his early 30s. I remember looking at myself in the mirror and I said, "You know, you're never going to change the world being a mechanic." If somebody chooses that as a life path, that's totally fine. But for me, it just, it didn't sit right.

And then, later on that day at lunch, I was fiddling with my phone waiting for my food. I'm like, "I wonder what the average lifespan is." I was 18 at the time. It turns out the average lifespan, I think for women, it's 80 years; for men, it's 79 years. I took 80 years and multiplied that by 365 days. It was then I realized that I had lived 6500 out of my 27,000 days. I could see every day ticking from that point forward and that caused me to quit that job that afternoon.

I realized that like every day is ticking, that my life is something that's finite. It has enabled me to make those difficult decisions when I am unhappy.


Mm-hmm. I love that you spoke about the finiteness of life and just making each day count. We can be focusing so much on work that we forget to ask if what we are doing has meaning.

Here is the next part I want to ask. Entrepreneurship has a lot of highs and lows, like in your journey. When you think about mental health, what does it mean to you?

Mental health is... I mean, in full transparency, it's something I have had a lot of judgment towards for many years. I'm scared of labels and I'm scared of things that I don't understand. Obviously, mental health is a big, big, complex, multifaceted problem in today's society. People can link it back to nutrition, people can link it back to social ties, and there's so many things that contribute to it. For me, I've had a lot of judgment towards it, which is why partly I haven't spoken up about it all until rather recently because there's more of a need for it.

As you know, I spoke at an event recently on mental health for entrepreneurs. I speak a lot and when I was given that opportunity, I said, "Absolutely, I'll do it," because I wanted to support two friends of mine organizing the event.

When I went to go post about the event on social media, normally, I always say my standard line: "I'm so excited to speak at this event.” But while I was typing that up, I was like, "I'm actually not excited at all to speak about mental health," which is actually on some level precisely the problem. We don't want to talk about it.

It’s something I've had struggles with. When I was spiraling downwards, when the business was scaling down, and I hit rock bottom, I had my own moment of… I guess, suicidal thoughts. It entailed me driving towards the city and seeing a fresh concrete median on the horizon. Although it wasn't premeditated or anything like that, I was having a bad day. There wasn't even a voice in my head, it was just this decision that was made of driving my car right into that fresh concrete median.

And I remember, first, just this sense of peace wash over me. That all the crap that was going on would soon be over, and I'll never forget it. I can't put it into words how that felt, but as I was driving towards that concrete median, I remember looking down at the steering wheel and seeing the word "airbag" in its very distinct font.

I'm like, "With my luck, I will have failed as an entrepreneur, I will have failed as a husband, I will have failed as a father, and I'll have failed killing myself as well, because this stupid airbag will probably save my life."

I ended up pulling to the side of the highway and just regrouping. Thankfully, that was the only moment I've had.

But there's definitely highs and lows to being a CEO of an organization. Even though I'm successful by most people's standards and and I have a beautiful family, and I know how fast I can slip into that dark place. I'm always on edge that it can happen again.

And it's this, honestly, it's this fear that I live with day in, day out. Like I said, when you have good days is one thing, but sometimes, you can have a bad day. A few things can compound that and it's really easy to get into that funk and spiral downwards.

Like I said, it's something I don't fully understand, haven't fully processed. It's something I'm speaking about when people want to talk about it because I think there's value in being an open book.

If people don't buy your struggles, they won't buy your successes, so I have no problem being transparent about it. But unfortunately, I don't have much of an answer, aside from knowing that a lot of entrepreneurs I know that are struggling with mental health. Behind the scenes and really, society as a whole. We're all struggling with it.


Jayson, I just want to really acknowledge you for sharing your story so openly with us. Just the courage that it takes, especially as someone who is so well-respected in our community.

Yeah, it's definitely a conversation that's starting to happen behind the scenes and slowly starting to seep out there publicly. But it's also kudos to you for really committing to doing the work that you're doing. Really spreading the word and getting it out there.


Thank you, Jayson. That means a lot.

You're obviously a community builder. You have such a gift in the way you connect so deeply with founders and how you get them to open up. What do you see as possible for founders, and really, for our community?

It's interesting because I know there's a lot of talk in the tech world about the responsibility of companies like Facebook and Instagram. As tech moves forward, there is social isolation and the impact on that. There was a book called Never Eat Alone by Keith Ferrazzi, who wrote another book called Who's Got Your Back. In that book, he interviewed a thousand people at random and he asked them one question: “Who has your back?"

Surprisingly, 55% of people felt like nobody had their back. Even more surprisingly, 60% of those people were married.

Social isolation is a huge problem, and on some level, what we're doing with MastermindTalks and MMT, we're trying to solve that on a very small scale with a very small group. But there's need, there's definitely strong need for community. We all have a strong need to belong and in the traditional business world, it is not focused around connection. It's often focused around just meetups and networking, that kind of stuff. Very surface level stuff. Unless you have a core group of friends that you can really open up to, that's problematic. It's really problematic.

My hope is that we continue to talk about it. I don't want to put too much weight on your shoulders, but as you keep pushing this boulder uphill, so to speak, it will get to a point where you reach critical mass and everything happens on the way down. I'm optimistic that we'll work our way through it, but I think there's alarm bells that need to be rung, and unfortunately, not enough people are ringing them.

I know some organizations like VaynerMedia, Gary Vaynerchuk's company, they have a psychologist on staff in the office, and they have about 800 employees. I don't know how much overload that one psychologist has, but that's a step in the right direction, right?

I have a therapist. I could not imagine navigating the world without one. I've had one for the last three years, and that's been a game-changer. I cannot, like I said, I literally cannot imagine my life not being able to have a therapist as a sounding board.

We all have a deep desire to feel heard, to feel seen. Even if we're in a marriage, often times, it's difficult to completely unravel yourself. If you're a founder, going back home to your spouse who most likely is not a founder, it's hard. You can't talk to them about trying to make payroll and you don't know how you're going to do it, all those kind of things.

I remember saying once that being an entrepreneur is like one day you're buying cars in cash, and the next day, you're canceling newspaper subscriptions to make payroll. Right?


That's so true.

Just pushing the conversation forward is going to help tremendously. We have Anthony Bourdain and Kate Spade and committing suicide. Just, unfortunately, we're all struggling with mental health and it's going to take a few more people at the top to at least talk about it.

When you ask people, when they hear the word "successful" in the tech space, who's the first person that comes to mind? Elon Musk, right? And you listen to his interviews, he's not a happy man.

And I have no judgment towards him. I think what he's doing is amazing, but he's also sacrificing himself to do it and he's starting to open it. He’s saying, "This is not a path anybody should do. It's incredibly miserable and it's incredibly hard," and so I applaud him.

Yes, he's a brilliant entrepreneur, and he's pushing the whole humanity forward, but there's a cost to it, and he's not immune to that. Having these discussions, opening up, it makes people who are struggling feel they're not alone. I think that's really, really important.


Mm-hmm. I love what you said about bringing this dialogue forward. Being real with one another. Given that, what's the most important thing that someone could do to move mental health forward?

The biggest thing is instead of changing the outer world on some level, focus on changing your own world. If you don't have a core group of friends that have your back, I would start there. We all need to get our house in order, so to speak, before we start trying to change the world.

In my case, that's entrepreneurs. But it could be single moms have a deep need to be understood, appreciated and seen. Former military vets have a deep desire to feel seen and understood and heard and have a strong sense of belonging. Create the semblance of something that as a community is really, really powerful.


Thank you so much, Jayson. For just sharing your story, for sharing your perspective, and for your openness in this discussion.

Like I said, I can't stress enough the importance of the work that you're doing. I know you have a very strong mission behind it and a very strong why propelling you.

If there's anything I could do to support you, please let me know. Huge fan of you and the work that you're doing!

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