Dan Martell is the CEO of SaaS Academy. He also co-founded and raised venture capital for his previous startups - Flowtown and Clarity. Dan is a former advisor to billion-dollar SaaS companies like Intercom, Hootsuite, and Udemy, he is an investor in 40+ startups and he runs the biggest Youtube channel for SaaS entrepreneurs in the world. Dan was named the top angel investor in Canada in 2012. Even though he didn’t go to college himself, Dan prides himself in being invited to speak to the MBA classes at both Berkley and Stanford.
In this raw conversation, five-time tech founder Dan Martell shares about the time he went to jail and how rehab gave him the tools to become his best self. He also talks about the importance of reaching out and how we can truly be there for one another.
Thanks for making the time to do this. I was super excited to connect with you because Mike [Brcic] and a lot of people from MMT were telling me that you’re awesome.
Well, I appreciate that, Cherry Rose. The truth is I pay them to say those nice things because it's just easier, so that's why. I don't want to give you a false sense of expectations.
[laughs] I'm excited we're connecting. I know you've been a seasoned founder, but also, a seasoned investor.
Yeah. I'm a weird person in that sense as well because I'm also really open about my past and my journey. The fact that I grew up in a really chaotic environment, ended up in jail twice by the time I was 17, rehab, and software being the thing that saved my life. That always throws people off when I speak at conferences because they're like, "Why is he telling me this?"
I want to have people understand what drives me and why I do what I do, and because of that, I get a lot of people that reach out that are struggling and having challenges. They feel comfortable knowing my story so they share theirs. Many times it is, "Please don't tell anybody. It's off the record. Nobody knows this."
I had a lot of friends in the tech space take their lives, depression, challenges, entrepreneurial guilt, and making it okay to discuss I think is going to serve a lot of people. It sounds like you're leading that charge in a way and it's appreciated.
Thank you for the acknowledgement. I have been through a lot of pain myself, so this movement means a lot to me. How did you get here?
I went through a lot of chaos as a child, as a little kid. Second oldest of four. The oldest is a boy. I've got two younger brothers, and at 11 years old, I got diagnosed with ADHD. I got put on Ritalin. I thought for a long time that there was something wrong with me, that I was broken, I had a huge anger issue. I acted out quite a bit at home, to the point where my parents didn't feel safe even having me in the house.
When I was 11, I got put into a crisis center and eventually, into foster care. Really, just things spiraled out of control. When I was 13, my parents got divorced. I discovered drugs, cocaine, marijuana, acid. You name it. Pretty much anything that would get me high and ended up in jail.
The first time I went to jail, I was 15. When I got out, I said, "I’m nNever going to do that again," go get a new set of friends. Literally, it lasted 24 hours. I Eended up right back where I started within a day, and a year later, found myself drunk and high in a high-speed chase. I smashed into the side of a house and went to pull a handgun that was in a handbag next to me. I pulled the gun to let the police do their job. Lucky for me, the gun got stuck, and I woke up sober the next day in a jail cell.
That's what shaped me. Over the next few years, I had people show up that really helped guide me. There was a guard named Brian that sat me down after I got in a fight and just told me that he believed in me. He didn't think that I belonged there and that conversation really shaped everything.
I mean, it was the first time in my life (at 17 years old) that an adult had said that to mean adult at 17 years old… it was the first time that I ever believed it.
Then I got released early to go to a rehab center and I did. 11 months of working on myself, redefining my relationships, my anger issues, my emotions, and learning how to cope. It was at the end of that program my life raelly changed. I was helping one of the maintenance guys, this guy named Rick, clean out an old cabin. It was a church camp that they took over, and in one of the cabins, there was this old computer with a yellow book on Java programming sitting next to it.
I booted it up the computer and started reading the book. It read like English, which I always thought computer code would be like hexadecimal numbers, and zeroes, and ones. I plugged the computerit in to the terminal, and all of a sudden, I got it to say, "Hello World." I literally thought I was a genius. Anyways, I'm a tech guy at heart. I'm an extreme extrovert today.
Over the last 20 years of building companies, I've started five tech companies. The first two were complete failures. The last three had quite a bit of success. I exited those. The last two were venture-backed inat San Francisco, so I raised money for some of the best investors in the world. Steve Anderson from Baseline Ventures led both of my rounds at my two previous companies, Clarity and Flowtown, but I also had Mark Cuban invest; not through Shark Tank, but directly as an angel investor.
I don't know. Honestly, Cherry Rose, my life, it doesn't make sense. Like the odds were against me, the stats were against me. I should have ended up dead in a ditch.
You know what I think? The world rewards those that make courageous decisions, and from an investment point of view, those are the kind of founders that I invest in, the ones that show they're resilient, and are willing to put in the time and do the hard work, right? It comes back to what's the impact on their mental health and their wellness around that.
So, We can go anywhere as you want, but that's me. I'm a diehard entrepreneur. I don't watch team sports or anything. I pretty much work out &, talk about SaaS businesses. I'm a heavy software guy. That's pretty much what I do every day. My purpose in life is to connect with passionate, excited, motivated entrepreneurs that want to 10X their life. If I wake up and do that all day long, then my day was a win. That's what I do. That's who I am.
I'm a father. Like literally, the coolest thing that happened to me in the last five years is… my son Max, and 11 months apart, my son Noah. The realization is crazy to me, that I'm responsible for beings, something that's going to live way past my time here on earth.
I didn't even expect that. I was like, "Oh, wow." It's not even being a good dad. I now have the opportunity to break all these previous patterns that I had been exposed to. Start a new lineage of what's possible for my kids' kids' kids' kids' kids. That's what drives me.
I just wanted to acknowledge you for your honesty. It is so refreshing and I am touched.
I know you support a lot of founders and there have been a lot of problems with mental health in our industry. What do you see right now with mental health?
I coach a lot of really high-performing entrepreneurs, guys that have built hundred-million-dollar-a-year companies in five years, right? It's definitely a mental game. It's a mindset thing. It's not about the business model anymore. It's not about the tactic. It's really about leadership, and do they feel like they're the right person to continue that charge? I always ask myself like, "Where did I get that from?"
One thing is I believe that I can only keep what I give away. Right? I need to give it first. It's this kind of abundance mentality I'm incredibly grateful, so I have a very structured gratitude process every morning, every night. Even whenever I get into a negative thought. Actually, the other day, I was talking about the book The Untethered Soul by Singer.
Such a good book.
Exactly, right? I definitely recommend it, so just talking about like those moments where you start to see yourself going down this like negative thought pattern. Acknowledging and stopping it, then letting it release. Right?
I just feel like there's a lot of that. There's the physical aspect too. I'm a big fan of sweating every day and it's not because of my physical appearance needs. I just do it for the mental clarity. I had very severe ADHD. Medicated. Blah, blah, blah.
Whenever I start to go into a funk, if I'm not able to kick it quickly, I go surf, run or workout. We have those days where we just feel like we got kicked in the stomach hard and it's nothing we did. It just happens to us. I try to immediately go into, "Who needs me the most right now?"
Yeah, there's something powerful about that. About service.
Actually, I'm getting a little emotional because... [tears up] I don't know. I just think like there's so many people that showed up for me and I don't even think they know. You know what I mean? Like when we reach out and we don't tell people why, but we're really hoping they answer.
Any success I've ever had is because somebody was there, and those moments were really hard. When they answered the phone, I really shared with them the crap I was going through. The universe sometimes... Like when we think of somebody, we should definitely reach out because there's something... There's a reason why that person came into our mind.
Right. I would love to ask… What's been like the most difficult part of your journey?
There is no situation that anybody could be going through for the most part that I haven't personally gone through, right, from people trying to embezzle to acquirers, last-minute drop of deal to partnership challenges, et cetera.
I mean, I remember one day, I'm building my company Sspherice. We're about 12 employees, a million bucks in revenue, and I was working 100-hour weeks for about a year, a year and a half. This is like after two failed companies, so it's not like I just came out of the gate. I was about 25 years old, 26, and just reinvesting every dollar back into the business., right?
Started with $85,000. After I worked for a year and a half to save it, to start the business,. I was away with my fiancé at the time and came back on a Sunday. I get a voice message from one of my clients letting me know that one of my key employees was asked to leave thean organization. My employee that was on-site, was asked on Friday to leave. There was an incident and I would be hearing from their legal team.
Just worst-case scenario like, "What the heck happened?" I'm getting sued by this multinational company. I'm a little guy. I'm probably going to lose my business because of one person's mistake. This is crazy. Luckily, I had a mentor at the time and I called him up. He said, "The best thing you could do is put on a suit, jump on a flight, and be at their office when they open up the next morning."
I jumped on a plane 5:45 AM. We're an hour ahead time zone from the East Coast. Ended up in New Jersey at 9 AM, sitting in their waiting room, and I said, "I'm Dan. I'm the CEO of the company. I'm here to do whatever is going to take to hopefully make it right." It cost me $50,000, right, because what happened is they [my employee] essentially lost the contract, and that's why they [this multinational] were suing us.
You name it, I’ve been there. I've had athe fiancé at the time four years into that business… I came home and she drops the ring on the table, on the kitchen table, walks away, and says, "I don't want to do this anymore."
How did you make it through?
One of my mantras. I have a manifesto, and one of them is, "You got to become the person who can deal." Right?
I always ask myself. Whatever I'm trying to achieve, right, at every level, building a venture-backed tech company, scaling it up, and doing things that are world-class, I ask, "What do I need to become?"
Today, my wife, Renee, is my best friend. Seeing mMy kids isare one of my favorite parts in my day. Having and still crushing it in business, that was 100% a byproduct of asking myself that question, "Who do I need to become to have that stuff?"
As vulnerable or sometimes as painful as it is, there's usually a gift beside our wound.
Yeah. People who have gone through the most are the most to give, right? In many ways, I think that life is about becoming a belief collector. It's about going through life and looking for different beliefs and just grabbing the ones you like. Putting it in your psyche and asking yourself how that shows up in your life.
I continuously ask myself how I can get more from a place of honouring the fact I'm alive because somebody had a plan for my life. I just know that in my soul and I would hate to meet that person and find out that I didn't deliver what they thought I could. There's like no good reason that those sequence of events showed up for me, and I'm willing to dig deep and do things that are hard as hell. You know what I mean?
Yes, the pain, the obstacles, the experiences that we go through, they prepare us for the work that we do now.
Philip McKernan, an incredible guy that I've worked with…
Oh, he's so awesome.
Philip. I work with Philip. I went to Peru. I went to Dublin with him. Philip is the guy that I call when I'm really struggling with life questions. His belief is that everybody on Earth is here to help other people get through the thing that was most painful to them in their life.
It's at our core of our DNA as humans, the reason why we share, and create, and educate is because what drives us is to help another human being get through, or deal, or understand one of those deepest wounds. Right?
I love how aligned you are. I have done a lot of this work as well. The deep work, it is the stuff I have done myself and the stuff I do with founders. It has changed my life and I hope I can bring it to our community because people are hurting.
Honestly, Cherry Rose, I feel blessed that I ended up on a rehab center at 17 years old. A place called Portage Atlantic in New Brunswick. For 11 months, I did deep work like personal development, deep work every day. This is a special place, right? One of the reasons it's special is that all the staff were ex-drug addicts.
All of a sudden, you've got people that have been there, done it, giving you advice on how to get through it. Not the person that just read the book. I mean, that lesson at 17 has been the driving force of growth in all aspects of my life. If I want to learn how to do something, I go straight to the top to the person who's done it before and reverse-engineer it.
I learned that at 17. That's crazy. I know a lot of people who still haven't figured that out. I learned how to deal with my emotions. Life is about emotional management and understanding what drives us.
I heard some of the most horrific things happen to people that ... I don't know. It's like it's surprising, like it really ... It inspired me that they were still functioning as a human.
I used to build tech companies like Clarity because I was too much of a chicken shit to actually say, "Hey, I want to coach people and help them.” Instead, I'll build a tech platform, and in that way, I'm still a tech founder because that was my identity. Truthfully, I did 1,300 clarity calls. There is no reason I should be doing 1,300 clarity calls in a two-year period. I did it because at my core DNA, it's what I love to do more than anything else in the world.
I want to ask… Knowing and connecting, connection to self, connection to others. It has been a big theme in this interview. What has helped you build deep connections with people?
Yeah. The first rule is you got to go first. Right? That wasn't as obvious to me in the early days. I mean, here's the reality. You want to hear something crazy, Cherry Rose?
What I went through as a teenager and as a child, I didn't share with anybody for 15 years. It's funny that we got connected through Jayson Gaignard and MastermindTalks because the first time I ever shared my story was on his stage in year one.
The only reason I ever shared it was because he came to me the the day before I was speaking, to tell me that they were doing a $25,000 prize for the person who gave the best talk. We're talking Marc Ecko, Tim Ferriss, et cetera. Like all these really well-known professional speakers., right?
I'm a tech founder. For some reason, he asked me to speak, and I knew I wasn't going to win by talking about a marketing growth hack.
I went back to my hotel room, pulled out a piece of paper, and jotted out the narrative that I thought would resonate that I should share. One I could tell without completely falling apart because that was real…
My wife was there. Max was like three months old. She was pregnant because our kids are 11 months apart, and we're in Toronto, and she doesn't even know this story and she's in the audience.
I said, "Babe, hey, I'm going to share something. I just need you to stick around. Listen to it and I want to come find you after.” I went on stage, bared my soul, and shared the story about how I got in a high-speed chase, almost took my life, and how that shaped who I was as an entrepreneur.
I get off stage and I had the most incredible people come up to me and shared their story. Right? I had a guy literally find me in the bathroom. He must have waited until I went in the bathroom and say, "Hey, Dan. Thanks for sharing your story. Can I tell you something? I went to jail as an adult for drinking and driving. I've never told anybody. This is the first time I've ever told anybody…” He started crying and I started crying…
I want to connect with people on that level.
Here I am, hugging a stranger in the bathroom. We start crying together and like I'm just like, "This is what humanity is about." If you want that in your life, you need to share it. You need to go first and what happens is you start attracting people that maybe don't tell anybody else.
Yeah. When we are just open and authentic, we never know who we are really impacting. The friends, the mentors, the people who we could truly connect with.
There are a lot of people who are suffering right now, people in the earlier stages of their journey. What could we do together as a community?
The number one thing is to start building your 3 AM friend. Like who's your 3 AM friend? When you're still up at 3 AM and your world falls apart, who do you call? We could all just start by saying, "Hey, if you're going through a tough time and you need somebody to listen, you can always reach out."
I mean, imagine if everybody did that… Didn't try to fix the problem, just was there to listen. This is a thing about depression and stuff. People who are depressed don't reach out. I know people want to think that that's what they're going to do, but they just don't.
If you have a friend that you know is going through something tough and you expect them to reach out when it gets bad enough, that's crazy. That's not how it works.
People think successful people have their shit together and it couldn't be further from the truth. They just have a process for dealing with more shit. That's it. I don't have my shit together more than any other person. I'm just capable of dealing with more.
Thank you for spending your time with me, Dan. For being real. I am grateful for the cries and the laughs we shared.
This has been absolutely special and unique. I just want to thank you for creating this space because I shared stuff with you that I don't get often get the opportunity to share.
Keep shining your light. I look forward to hanging out soon.