Happiness at Home with Michael Perry

July 25, 2023
James Whittaker

Check out this episode on the Win the Day Podcast

You cannot get through a single day without having an impact on the world around you. What you do makes a difference, and you have to decide what kind of difference you want to make.”

Jane Goodall

If you’re a parent, you’ll know that keeping your family happy, your house organized, and your own stress levels down is almost impossible. However, our guest today is on a mission to solve that problem once and for all.

Michael Perry is the founder and CEO of tech startup Maple, an acronym for Make All Parents Lives Easier. After becoming a father in 2020, Michael launched Maple as a free mobile app to change the world of parenting and have your home running like a well-oiled machine.

Already, Maple has partnered with more than 70 brands and has more than 80,000 users in the US and Canada alone. 

Previously, Michael was the founder of Kit, an AI employee for small business owners, which was acquired by Shopify in 2016. At Shopify, he was a Senior Director of Product and oversaw Partnerships until he left in 2020 to launch his parenting app Maple.

Michael has been recognized by Forbes, Inc Magazine, and Business Insider for his role as an emerging leader and influencer in marketing, tech, and AI.

Outside of the business world, he is a proud father, uncle, brother, son and husband. 

In this episode:

  • The biggest contributors to household stress and conflict
  • How to balance business with family
  • The biggest mistakes parents make (and how to fix them); and
  • How you can use technology to bring more happiness into the home.

Michael is also extremely open about his struggles with anxiety and self-hatred, which is certainly refreshing in the world of filters and edits.

Before we begin, the right bit of inspiration can completely change the trajectory of someone’s life, so if there’s a friend or loved one who needs to hear this episode or could use some help to Win the Day, share it with them right now.

Let’s WIN THE DAY with Michael Perry!

James Whittaker:
Michael, great to see you. Thanks for coming on the show.

Michael Perry:
Thank you so much for having me. That was probably the most impressive rundown I've ever heard of me. I'm nervous now!

Well, I'm so excited you're here, and what a journey you've had.

To kick things off, is there a story of struggle or success from when you were growing up that gives us a bit of a sense of what your childhood was like?

As time has gone on and I think back on my childhood years, I feel so incredibly fortunate for the household that I grew up in. My mother had me in her early 20s. My father was in his early 20s. My mother was a waitress, my father was a car salesman. 

I feel really fortunate to the extent that my parents very early on put this huge amount of emphasis that work ethic was going to matter, and that you were not going to allow any one particular thing to define who you are. And so while I struggled with school at an early age, barely making grades, my parents always had this unlimited belief that somehow, some way I was going to find my true self.

From a very early age, I had a set of parents who deeply believed in what I was capable of becoming.

And so when I look back, the stories and tribulations of being a young man, the thing that really sticks out that I feel the most grateful for was that from a very early age, I had a set of parents who deeply believed in what I was capable of becoming. 

There's one moment that always kind of sticks out with my mum marching down to the principal's office, reminding them that I was struggling to pass classes, that didn't mean I was stupid, and that I just learned it in a different way. And I think just all those moments kind of compounding gives you the belief system in yourself to do really great things and overcome very difficult situations.

What were some of the strengths and weaknesses you had in terms of learning?

Well, when I was super young, my dad used to take me to work with him all the time. So I started working when I was seven years of age. 

My uncle ran a video store. My father was selling cars. So I kind of went back and forth between working at a video store on the weekends to going to work with my dad. He used to pay me $3 an hour to wash cars. He would take me to car shows. And I really had the privilege of observing someone that was incredibly talented and how he communicated with people. 

My father used to always tell me, the person who's buying the Volkswagen is just as important as the person that's buying the Rolls-Royce. And so just learning how to treat people as an equal, at a young age, really has set me up for success in terms of how I've been very successful at developing partnerships, building a business and things of that nature. Just basic human decency goes a very long way.

My father used to always tell me, the person who's buying the Volkswagen is just as important as the person that's buying the Rolls-Royce. 

I was always hyper creative in school, but sitting at a desk was not the right arena for me, from 8:00 in the morning to 3:00 in the afternoon. Where I learned the most was standing on a car lot, standing in a video store and really learning about how real life worked. 

By the time I was 13-14 years old, I was working a 40-hour a week job. And by the time I was 18-20, I was making $150,000 a year selling cars. That whole journey is a pretty uncommon story for kids. Most kids aren't working at seven or having the unique opportunity to directly learn from their parents in a business environment. 

So I've always kind of used that as my competitive advantage that, at 37, I've been at it for 30 years. So even though I'm competing against people who might have more runway of time on earth, they've been here longer and been around the block, I've been at it just as long.

I had a lot of struggles that I've spoken about a lot on the show, anxiety specifically when I was in high school and starting university, which I think is something that, in my experience anyway, is something that doesn’t ever fully disappear. 

I'd read something about your background as well, that you had some struggles around anxiety?

I have extreme anxiety. I had anxiety even this morning. I had to do my own mental preparation knowing that I was coming here. 

And it's something that you have to just recognize that we all have demons that we're battling. I don't think anyone who suffers from anxiety wants to have anxiety. Anyone that's dealing with an anxiety disorder will be the first to tell you it's not a fun thing to have to take on every day. It's so difficult. And I've gotten to a place, thankfully, where I can feel it coming on and I'm able to communicate that now to my wife and to the people around me that I'm struggling right now. 


You’re reading an excerpt of this interview. To access the full Win the Day episode with Michael Perry, including bonus content that doesn’t appear here, check out the YouTube or podcast version. 🚀


It's definitely taken me away from doing some of the things that I love. I used to do a tremendous amount of public speaking. I used to get asked to speak at conferences. Because my story is relatively uncommon, to go from no formal education. I didn't finish college, selling cars, teaching myself how to code, building a venture-backed business, selling it to a publicly traded company.

So I get asked to speak a lot about that because I think there's a relatability in that I wasn't some kid that was a wizard and then went to Stanford or MIT or Harvard and then became some big success. That feels so untouchable for so many. But I've had to stop publicly speaking a lot because getting in stage in front of 20 people is almost harder than 5,000 now. 

And just the anxiety, the triggering is just... It's something that I have to really, really, really want to help that audience understand the possibilities.

Where does it come from you? Obviously there's a genetic component with some of these things, but certainly in my experience, there seems to be a mixture of lifestyle and genetics.

Yeah, I'm sure that some of it is deeply genetic, and my mum deals with some anxiety as well. 

Honestly, I think if I'm giving the most truthful answer, I think that there's a lot of self-esteem and self-judgment. In most of the environments, most of the places where I'm starting to feel like I am melting, that I'm feeling like my heart racing, my hands are sweating, I'm feeling it, it's always almost stemmed around the judgment of failure. Is my business going to collapse?

I still have immense, immense anxiety almost on a nightly basis about whether I'm going to make it or not in life.

I lay in bed at night dripping in sweat still. I've been an entrepreneur, software entrepreneur now since I was 21. So I'm 16 years in, and I still have immense, immense anxiety almost on a nightly basis about whether I'm going to make it or not in life.

It's a big burden to carry just having any business. Then you throw being a parent into the mix…

Oh my God. Yeah. 

I mean, you're a father. There is no body of work that matters more. It's interesting. I have less anxiety about doing the job of fatherhood right. I have a tremendous amount of anxiety about my children in the world, something happening to them, something being hurt.

The problem with people who are managing anxiety is that oftentimes you're filling the white space of your mind with a lot of negative forecasting. It's like, "This isn't going to work. I'm going to fail in front of this audience. I'm going to say something stupid. My kids are going to get hurt." That's so much part of the problem for me.

Oftentimes you're filling the white space of your mind with a lot of negative forecasting.

I can't speak to every person out there. And so oftentimes I have to just quickly try to replace those negative thoughts with positive outcomes, and that's how I kind of bring myself back. “It's going to be okay. My kids are going to be okay. My business, there's no guarantee, but I have a high bar of confidence that my business will survive, it will make it, we will have impact. We will be the company that we've set out for, I will be the father I set out to become.”

And you have to kind of talk yourself off a cliff.

What do you love most about yourself?

Well, if I'm being super truthful, I've worked extensively with an executive coach now for some time. I am someone who battles with a tremendous amount of self-hatred.

So I'm still trying to find that answer.

There's something called a hundred board and I used it to achieve a meditation goal I had. My plan was to do 100 meditations to hopefully start eliminating negative self-talk. About 60-something days in, I noticed that my negative self-talk – which had been my biggest weakness for 30 years – was eliminated completely through doing that. 

And it's amazing when you turn a corner in something that you don't realize how much more energy you can have. Just like people who have a bad diet, they don't realize how much energy they can have if they start to do the right practices.

Yeah, there's an aspect of me that feels like my self-hatred has propelled and fueled a tremendous amount of success. It's a really difficult aspect of the relationship with myself. Because there's some aspect... If you really looked at where I started in life, the neighborhood I grew up in, the environment I was in, I'm probably in the 0.00001% of people who make it.

A lot of that self-hatred has a lot associated to my desire to get myself to that next level, to change that trajectory, to not like where I'm at, not like how I'm performing, not like how I'm showing up, not like how I'm thinking, not like how I'm leading.

I have not found the ability to love myself and do great work.

So much of the obsessive self-analyzing that is hyper focused on my flaws is almost like I'm constantly trying to iterate on myself. I have not found the ability to love myself and do great work.

That's really, really interesting. 

We spoke a little bit there in terms of relatability, and there have been people on the show who are actual geniuses, but people can't really relate to that so much. And I can't relate to that so much. 

But people who have imperfections, they're open about their vulnerabilities, that's what people love. It's what people embrace.

At the end of the day, this experience on earth has taught me even geniuses have problems. I haven't met a problem-free person. Some people are very good about hiding that. Some people are unwilling to talk about that or share that, which I think it does a disservice. 

It's the Instagram of real life. Instagram is this amazing storytelling platform where you get to curate who you are to the world. That's 99% of the time not true. Not talking about our own flaws means that we're curating ourself in the public eye. 

There's a tremendous amount of opportunity to become softer and better. It's not just like, "Oh my God. You're so good at this." It's like, well, fuck, I go to bed at night hating who I am. That's just real life. And there's mornings I wake up and I am overwhelmed with gratitude with where I'm at.

It's a very strong yin yang.

Big polarity there.

It's huge. 

And the reality of it is, and I believe this, if you like where you're at in life, then you have to embrace all the fabrics that have woven that together.

I love where I'm at in life. I love my wife deeply. I love my sons. I love my company. I love where I live. My life has turned out exponentially better than I could have ever imagined ever in my life. But there's a lot of demons that I still hold onto. 

At least bring me back in 10 years and maybe something has changed, but I haven't been able to let go of that.

It's hard when you're on that journey of acquiring users, raising money. Of course, you need more exposure to be able to do those different things. You're carrying the burden of your own home and everything else too. It's a very difficult thing because people are aiming for targets that keep getting moved, another carrot over the horizon. 

We can't help but feel that our life is supposed to be perfect, but no one ever promised that your life is going to be perfect. In fact, it's the complete opposite. Stephen Hawking said that "The universe doesn't allow perfection."

And there's also no balance in the short-term, especially if you have young kids and two working parents.

There's a whole different level of humility. The last three years for me have been extraordinarily beautiful and extraordinarily hard. I have dealt with more in the last three years, especially in the last 18 months. 
And I'm not a ‘woe is me’ person. Life is fucking hard for everyone. Excuse my language. But it's been tough. In three years, I've had a house burn to the ground. I've lost everything. I obviously have a four-year-old and a year-and-a-half-year-old, so I brought a new child home. I started a new company. I raised $6 million in venture capital. I fired people, rebuilt my team. I've had several family members pass away to illness. I've built a house.

If you like where you're at in life, then you have to embrace all the fabrics that have woven that together.

Life's coming at you. But one of the things that I deeply believe at this stage of my life, this is the only thing I actually feel that I have some clarity around, is that it takes a long time to understand: what are you greedy for?

Some people, they're incredibly greedy for money. Some people are very greedy for travel. Some people are very greedy for collectibles, whatever. I'm incredibly greedy to experience life. And if you really believe in that greed, if you really want to experience life, because I'm a firm believer that this is just such a magical thing to get to be alive, then you have to prepare yourself for a tremendous amount of pain, a lot of hardship, lot of joy, a lot of love, a lot of sadness, a lot of happiness, and some depression. 

And if you miss any of those things, then you didn't fully get to experience the human opportunity that our species is afforded. We're a very unique breed. Very few get to really feel all that.

So when this is all happening, my house burns down, it's like, well, you can rebuild a house. I also got to balance that out with bringing another baby home. No sleep? Well, someone once told me I wasn't going to have a baby. Raise money, super hard. Well, I also got turned down 50 times for my last company. I'm experiencing it. 

When you approach life in a super simplistic way of just bring it on, let me feel it, let me have balance, don't skew it one way for too long, it becomes just so much more digestible.

How do you reconcile chasing your own dreams and experiencing all of life while at the same time putting your children in an environment for them to get the most out of life? 

That's a great question. I recently had to make difficult decisions around this. First time in my life, I've made decisions as a father versus as a son or a brother. 

My wife and I made a decision recently to leave the Bay Area. That was a hard decision. My parents live five minutes away. My sister lives five minutes away. My niece and nephew live five minutes away. My brother-in-law, my family was there. But ultimately, when I talk about the greed of experiencing life, I have lived life as a poor man. I have now lived life as a somewhat comfortable man. I have lived life as a son, as a brother, as a life partner. I've lived life as a founder.

My children, specifically my children, because they're IVF children, they didn't ask to be here. So now I have to live my life as a father, and that's the only title that will never be stripped for me. My wife can divorce me, I'm single again. My children, I will die a father. And so it became very easy to put them at the forefront of my decision-making framework because the life experience that I seek the most right now, the most above anything else, is creating memories with my kids.

Do you have a family purpose as well as a career purpose?

I mean, I feel really very lucky that my career, where I'm investing my time directly overlaps with the vision of what I'm trying to create at home. So there is no off and on switch. 

The way that I think about this is quite simply our purpose is the same as every other living species. Our purpose is not to go be a great founder. Our purpose isn't to go play in the NBA. Our purpose to be a doctor. Our purpose is to take care of one another. That is the human purpose, to make sure our species continues on and is alive and well.

Now, society wants to tell you a different story. Scientifically speaking, our purpose is to care for one another. And so I think about that in terms of rings. My tiniest ring, the closest ring, the thing that I'm most in control of, are my sons and my wife. We're a team.

Our purpose is the same as every other living species: to take care of one another.

The next ring out of that is my family. The next ring out from that are my employees. The next ring out from that is my community where I live. The next ring out from that becomes further out of my control. But what I'm trying to demonstrate to my sons is that you have to, whether you're a doctor, you're still serving that purpose of taking care of your community. Your profession sits somewhere in that ring, whether you realize it or not.

This podcast sits inside of that ring. You're being a guiding light for people who are wanting to listen to this, to be motivated, inspired, change their trajectory, for them to play inside of those rings. And so I don't drift away from that framework. My life is so complicated, but it's also so radically simple. I take care of my children above anything else, and I work incredibly hard to be a thoughtful member of this species.

How do you feel about your previous business venture in terms of meaning and the feeling that you got compared to the work that you're doing now and how well you have linked up your personal purpose with your work?

I really think that there have been two lives that I've lived on this earth. I've lived life without children and with children. And when I look at my life without children, I was not the same person I am today. They've been the largest change of who I am. 

So in my last life, my last company, I grew up in the Catholic church, and my mother made me be an altar server from third through eighth grade. And one of the most important lessons that I learned in that experience – I'm no longer a practicing Catholic, I find myself much more aligned with Buddhism – but the most beautiful thing that I saw or I witnessed was the act of servitude, just giving to somebody else.

I remember this incredible story, this moment that I experienced where I watched this priest wash the feet of the first pew of people that showed up to church. And afterwards, I was super young. I was in the fifth grade. I said, "Father, why did you wash their feet?" And he said, "It's my job to serve them." And I always approach business in this very simple way of who am I willing to be a servant for?

I always approach business in this very simple way of who am I willing to be a servant for?

In my last life, I was a servitude to entrepreneurs because my grandfather was an entrepreneur, my uncle was an entrepreneur. The men that I admired were entrepreneurs. And I felt a deep connection to that community to give them every creative and strategic ounce of time that I had on this earth. 

And I feel very proud of the work that I did, which has quite honestly impacted probably a million people. I feel very honored about that and proud that I selflessly worked relentlessly hard for the betterment of those people. And when I became a father, I realized that my servitude was to my children, but my servitude was to sit at that intersection of my family and people trying to build families. It was how can I give everything emotionally to my children, and how could I give everything intellectually to my new community?

And so, I don't take a paycheck. I work completely for free. I feel very lucky that I've put myself in a position that I can do that. But my servitude is to families. I am a servant to them. I work relentlessly hard for them.

How does servitude to yourself in terms of daily rituals fit into that whole equation?

You ask the hard questions!

And in my experience as well, to clarify, I feel like rituals, daily routine, all that has evolved so much for me, trial and error, different phases of life, becoming a parent, different things to deal with.

Totally.

For me in the morning, I have my time in the sunshine. I do a journal. I've done it like 700 days in a row now. I need that space to be able to do that so I have more to give to everyone else.

That's beautiful, by the way. 

I'm probably in a chapter right now in my life where I'm not really taking good care of myself. That's just my only honest answer. There was a chapter in my life where I meditated every day, I found peace in my heart every day. 

Building a business is incredibly hard, especially with the ambition and the vision that we have at Maple. And being an equal partner in a relationship is really hard, and being a good father is really hard, being a good son is really hard. 

Any of those jobs done well require a tremendous amount of time, and I have made, for right now, I have made the very intentional decision to put all of those roles before caring for myself. I don't advise that, I don't think it's a bragging thing, I don't think it's a good thing, but I recognize that my business will fail, my relationship will fail, and my short experience of young children will be regretful if I don't make a very strong commitment to prioritize those three things. And there's very little room in my day outside of those three things.

There are times when you recognize that change needs to occur and you're ready to embrace that.

A hundred percent.

If you're not around, none of it matters. I mean, it sounds so easy. It's like take care of yourself. I mean, when there's been good surf, I'm an avid surfer, I'll find time to go surf and find some time to separate myself from reality. But I think there's a difference between shaped rituals, consistent habitual behavior versus these one-off moments where you're recognizing you need to invest in yourself. 

The real good ones, they build consistency. They journal 700 days in a row. They eat healthy. They go to the gym. Whatever it is that people need to build their system around, it's about consistency and discipline.

My consistency and discipline, it exists, but it just doesn't exist in terms of me. I get up at 6:00 in the morning, or 5:30. Whenever my kids wake up, I'm up. I make them breakfast. I'm at work by 7:30, 7:45. My wife takes our kids to school. I work pretty consistently till 4:00 PM. I go home. I spend time with my kids. I'm present. I have dinner with my kids. I wash my boys every single night. I put my boys to bed every single night, and then I go back to work. And that's what I have to do to be their father and build a venture-backed business and be an equal partner in my marriage.

And there will be times where the release valve is a little bit different, the intensity in those moments will be a little bit different, and I can then factor in the good behaviors that once existed in my life. I think the difference is at 37 versus 27 or 37 versus 30, is that I'm far more cognizant that I'm not doing a good job of taking care of myself, but I also see the light at the end of the tunnel. 

This is a game plan. It's a decided upon intentional use of time.

So in an interview here on the show with Tim Storey, he mentioned if you're not aware that the decisions you make at the moment can impact you in a way that it could take decades to overcome, but as long as you can stay not far from center and just keep everything moving forward, then that's quite noble, at least in the short-term.

Yeah. I mean, everything is better compounding. Bad behaviors compound, good behaviors compound. And I think that it's more so having the life experience. And on my fourth cycle of building a company, to understand how fragile everything is around me right now. 

I'm in an incredibly fragile spot. And so it's my job, at the end of the day, when you decide to be a founder and a father, it's my job to protect those two things. That is what you sign up for. You paint both sides of the fence.

Take us into the moment that you realized Maple needed to exist, and what was the problem that you wanted to solve with Maple?

At the time I was at Shopify. That's where I was at for four and a half years. I became a father. And just as a little bit of backstory to it, I think that at the end of life, there's like five or six or seven or eight things that you just can never forget. Everything else kind of just mushes together. One of those moments for me is the first time I held my son. It was such an insane moment. It was such a big shift in my thinking. 

I went from within seconds of thinking my whole life was about building companies, making money, winning awards, leading teams, yada, yada, yada, yada, yada, to within, oh my God, my only purpose is to care for this child. It's the only thing I can't fuck up. You know what I'm saying? 

It's the only thing I cannot mess up is being a father to this kid.

And with more interaction, that feeling only grows.

Yeah, you really understand why a parent would die for their children and kill anybody for their kid. You get it. It's nature taking over. 

And I went back to work, and two things happened simultaneously. One was I was having a harder time being authentic because that shift, that moment also changed my community. It changed my servitude. I was like, holy shit. I don't feel like I'm an entrepreneur. 

I mean, you have to imagine the identity crisis. I started my first company when I was 10. First company. I spent my entire life thinking of myself as an entrepreneur and wanting to be the world's greatest entrepreneur. And within seconds, my dream became that I want to be the greatest dad ever. Seconds. It still blows my mind four years later that that's what happened.

As a technologist, I started looking at what products out there could make life more balanced and easier.

And I went back to work. I wasn't feeling authentic. And then on the flip side, my wife and I had been together for a really long time. We're on year 17 now, but we're 13 years into our relationship with this newborn child, and we were no longer just two people living together. We were trying to share this responsibility. And I was going to work, she was at home. We had a three-month-old, and I just was not understanding what I could be doing better. 

It felt like there was just chaos at home. Doctor's appointments, just so much was going on. I was so out of the loop. I felt I'm failing at this new purpose, and that just felt awful. As a technologist, I started looking at what products out there could make life more balanced and easier. We've built technology to bring efficiency to every single job on earth.

This doesn't exist without technology. This whole whole industry doesn't exist without technology. SaaS businesses, fam tech, farm tech, ed tech, med tech, like everything, technology has changed everything, yet parenting has remained the same. 

And it just dawned on me that I was going to work every single day to try to make entrepreneurship, the hardest thing on earth, easier. Why was I not committing my brain power to making our life's work easier? This is our life's work.

How many podcasts guests have you had on this show? 100? 200? They will not be at your bedside at the end of your life. Not one of them. But your kids will be. And that is the most important thing for us to realize – that when you die, the world won't remember you, but your kids are going to miss you every day.

Does it frustrate you when you see companies like Facebook and Instagram using all their resources to, in many ways, make us worse off?

It kills me. It kills me because we have some of the brightest people in the world trying to figure out how a shark can swim around a cereal bowl. I mean, my God. What's wrong with us?

I really think about this. Are we that greedy for the wrong thing? It almost brings tears to my eyes. Because I've been around some actual geniuses, to your point. People whose brain power exceeds anything I will ever be capable of. So many of our problems are solvable. It's just such a disgrace that we're not all leaning in to fixing life at home, fixing climate, fixing these things that are a threat to our species.

This has been a very long way of explaining how I got Maple started, but it was those moments, those early moments where I thought my son, and now sons, they are my life's work. This should not be this hard. This should be way more enjoyable. Because the thing that I'm going to regret the most without a doubt in my life, is that I wish I was more present around my children, I wish that I could enjoy them more, I wish I could spend more time with them.

When you die, the world won't remember you, but your kids are going to miss you every day.

I will not be thinking about the missed trip to Ibiza or what company I could have built, or what startup I should have written a $25,000 check to. None of those things are going to be in my mind. Not one. Not even in the sphere. 

If you think back, when do we want to pinpoint the start of software, the internet, going 30 years, 40 years back, and we've kind of over passed by? Imagine how different parenting would be if someone had been working on this for 20 years.

We have messed up so many things, and so I think in a lot of ways, we need a moment. We need some renegades. We need some people to bring us back. I just deleted Instagram and Twitter and everything off of my phone. I just want to be there with my kids.

And when you think about the stress that parenting brings, there's been such an interesting time for me where it's true that to a large degree, that to fully experience life, you have to have kids because it does completely shift your perspective and evolve it so much. It is such a big change. 

But at the same time, I firmly believe that not everyone should have kids.

No, they should not.

Because of the stress and everything else it puts on yourself, on your relationship. Just like being an entrepreneur, it’s not for everybody.

I wouldn't recommend it to anyone. Honestly, I've probably spoken to in my lifetime, 10,000 entrepreneurs, easily. Conferences, whatever. I tell most people, "Don't do this because you want to get rich." That is the number one path to misery. 

You have to be manically obsessed in a probably clinically, mentally ill way with the problem, because it's so hard. Your quality of life is going to be so bad for so long that if you're not at that level, you're going to hate your life. 

To the points that we were talking about earlier, if you're not prepared to change diapers at 3:00 in the morning or go days, weeks, months, years of no sleep, of being up every day before 6:00 AM, no weekends, no breaks. If you're not prepared for that and you don't love that, if that's not the priority of experience of your time, you have to use that one admission ticket wisely. 

If you're not there, don't just do it for the sake of doing it.

Or people who have kids to fix their marriage…

That's the biggest mistake, right? I mean, to each their own, and I'm not one to judge, and I also think that not having kids is... It's the right decision for some, but I also feel like there's a huge aspect of... Again, it's just my hardwiring of being greedy for life, that you're missing out on such a divine chapter, a divine experience as a human being.

I hope I'm not sounding doom and gloom in this interview!

Not at all. It's great. You're keeping it real.

I'm actually a highly optimistic and happy person, but I feel like if you're going to just come up here and sell bullshit, you're doing no one any justice. I wouldn't change my life with a single soul.

I absolutely love where I'm at. The two things I'm most proud of is my marriage and my kids. Everything else is irrelevant.

Why did you decide that the free model was the path you wanted to go down with Maple? And what are the metrics that you use to evaluate how well the business is doing?

So we actually defer the cost of the app onto brands. We have a sponsorship program. We work with people that are similar in our space, who basically absorb the costs on behalf of the users, and we're thankful for our sponsors. 

We, at some point, may have a premium product. Ultimately, what it came down to is that I grew up with a 20-year-old mum, and I had a very difficult time stomaching, asking people to spend money that they may not have in incredibly difficult economic times when I know that the value could be there for them. 

So we will always have a free version of Maple. I think there will be a day where we have to have a subscription version of Maple, but if people don't want that, then they'll have the sponsored version of Maple. So it's always been from day one, our promise and commitment of having a long-term free option.

How we measure success, that's an interesting one because my own definition of that has changed quite radically over time. We used to say time in app mattered greatly because then we know that we're conquering their day. They are using Maple to manage their calendar and their to-dos and to establish some organization inside of the home. 

As time has gone on, I think more about how we can give them time back in the day. So weekly active users, daily active users, obviously core KPIs for us to measure in terms of just general stickiness and efficiency, but I think in order for us to do our job very long term many horizons out, we have to be incredibly committed to taking the burden off of the parent and helping them in such a way that they're given time back in the day. 

Because any parent would tell you that time is their real asset. They have very little of it to do the things that we're talking about. And so how do we actually build those workflow efficiencies and the automation and the simplistic use cases more streamlined so that they almost, by using the app less, we actually give them the most value.

Give me an example of a big problem that you see in the home that can create stress or conflict, and just one of the ways that you go about solving that?

So there's two extraordinarily large problems within the home that I see that Maple is trying desperately hard to tackle. One is just the basic premise that most households run under the 80/20 principle. 

In 1950, four out of 10 children had dual working parents. Today's number is nine out of 10. And so the difference being in 1950, we had this very rigorous kind of system in place that dad was going to work, mum was staying home, dad was making a paycheck, mum was running the household. In 40% of households today, mum is actually making more money than dad. But in almost all households, she's doing more work at home than dad.

So there's a tremendous amount of friction and frustration at home around just the actual labor and planning of the house. It's so tacky and so cheesy, but it's so true that if you ask most dads, "Who's your kid's teacher?" they don't know the name. "`Who’s your kid's doctor?" They don't know the name. "When was the last time your kid was at the dentist?" They're like, "I don't know." Who's planning the vacations? Who's buying the groceries? Who's folding the clothes? You start going down this laundry list of things, and almost always the answer returns back to my wife or mum, but she's also doing a 9:00 to 5:00 job.


You’re reading an excerpt of this interview. To access the full Win the Day episode with Michael Perry, including bonus content that doesn’t appear here, check out the YouTube or podcast version. 🚀


So Maple, as a platform, as a product, it defaults to sharing the load and the responsibilities and bringing more exposure to the inner workings of what's taking place at home. Everything about Maple is trying to be hyper collaborative. 

The second problem is that being organized is a skill. There's a reason why a lot of people are not organized. There's a reason why people are obsessed with companies coming in and cleaning out their pantry and organizing their life.

In 40% of households today, mum is actually making more money than dad. But in almost all households, she's doing more work at home than dad.

There's a reason why a lot of good leaders recognize their own shortcomings and they have the privilege opportunity to hire an admin to help them organize their life, maximize and optimize efficiencies. Most parents don't have the skillsets to do that.

So life feels incredibly chaotic because the biggest dirty secret about parenting is that, and I'm sure you're probably feeling this right now, is that right around the time your kids turn two, you become an administrative assistant to your kids. You're balancing their school schedule, pick up and drop-offs. You're balancing all their friends' birthday parties. My son plays T-ball and he's also in karate, and he's doing soccer practice and he has swim lessons. And so all of a sudden you are the admin to your kid.

And if you don't have the tools and you don't have the organization around that, that admin responsibility falls solely on mum's shoulders, and mum is now trying to balance administrative work for her household, her job, and actually running the household. And so just the general disorganization and chaos and not being able to keep everybody on the same page creates a tremendous amount of frustration. 

I think it's fair to say, and one of our core beliefs is that when Maple is successful, we not only can build happier homes, we're building healthier children because kids feel that stress, tension, the offset of the relationship between their parents.

I won't even get into the details of the horrific feedback emails and support tickets that we have about the venting. We need to redefine what masculinity is and what taking care of your family looks like. It's no longer making a paycheck. That is an expectation. That is not the job. That is the expectation. 

The job now is how much emotional support are you providing your wife and your kids, and how much labor at home are you willing to support as well?

Especially when the mum is going through pregnancy. It might not even be a successful pregnancy the first time, so dealing with emotional things, physical things, all of the feeding and pumping and everything else after that. And then if you have multiple kids, multiple pregnancies in the mix.

Back at work. I mean, it just becomes unbearable and it just becomes unfair.

I talk to a lot of people all the time about parenting, and I just keep it really honest, which is... And I think that this has to be more of the conversation is that when I stood on the altar with my wife, I wasn't marrying an employee. She doesn't work for me. I don't know why people just think that their wife is just going to be working for them. We have a partnership. We are co-founders to a life. We co-created humans. 

I couldn't imagine if my business partner and I operated in the same environment of a traditional heterosexual household. He would be like, "F you." Right? We've been building companies for 20 years. Yeah, he'd be like, "I'm not signing up for this shit. I'm not, you're lackey. I'm not going to fold your clothes." So we treat our business partners as equals. We give them a certain level of respect.

The best piece of marriage advice I ever heard was that marriage is a 60/40 proposition in the other person's favor.

Yes. That is it.

That's exactly right. That's what I'm saying is that it has to be that you're leaning in a little bit. You have to be thinking you're leaning in a little bit harder. When both people think that, things are better off.

But I think that most households operate under this 80/20 principle, and I just think that Maple is deeply positioned as the back office administrative stack to just change that dynamic.

What about the best parenting tips or hacks you've got for people to optimize their home?

Well, besides using Maple, of course!

Honestly, I think that it's so basic, but I would strongly encourage people every Sunday night after their kids go to bed to just check in with their partner. I don't think enough people do that. Just like what's on the docket for the week? Are you good? Where can I help? Here's my week. This is where I'm going to be... I mean, Wednesday's going to be bad for me. 

It's just crazy how people continue to go through the motions and just live life without actually being a team. I couldn't imagine expecting my employees or my co-founder to just know everything that's going on in my head and just assume that they're going to build what's going on in my brain. No, we lay out a roadmap. We have quarterly reviews, we have daily standups. 

There is such an over index on communication at work, such an under index of communication at home.

Especially when you look at communication and financial struggles are the two biggest reasons that people get divorced. You're solving both of those in the one hit through Maple.

Most people have told me that they would forgive their spouse for an affair and they will divorce their spouse out of frustration over the workload at home. I'm not encouraging people to go have affairs, but I think that there was a time and a place where that was probably the leading cause of divorce, right? That is not the case right now.

Most people have told me that they would forgive their spouse for an affair and they will divorce their spouse out of frustration over the workload at home.

Most people are just so beaten down and so exhausted of trying to take it all on themselves. The financial stress, the bills, the school schedule, all that stuff that they're like, "If I divorce, you have to legally show up. You have to legally show up in this partnership. You have to have your three days a week." 

It's like, why are we letting it get to that?

For sure. 

Why do we champion people for their professional achievements and how much output at work they have, rather than championing people who excel in the home at raising the next generation?

Honestly, this is going to sound like a broken record, but I think it comes down to what we value. That's the problem. The underpinnings of all decisions is what you're striving for as an outcome. 

If you're looking for financial gain, you're going to coach, invest, do whatever it takes to make more money. We've all done it. It's like you invest in the people. You hire the best people, you recruit, you send people to conference, whatever it is. We will go to no limit to provide people with the resources to be successful in their job. Need a new computer? No problem. Need a screen, certain mouse, there's no limit.

The underpinnings of all decisions is what you're striving for as an outcome. 

When it comes to our home, we put lots of glass ceilings. The employer puts lots of glass ceilings on their staff, spouses put lots of glass ceilings on each other. And so I think that the conversation has to be constant at this point. We need people with stronger moral compasses leading society. And we need to have this constant reinforcement that your life and your life's work and your purpose and your servitude is to the next generation. And that circle starts small and it gets bigger. And we don't value that. 

You watch the news, that's not what's on the news. You have conversations at work, that's not what the conversations are like at work.

Everything around us is an amplification of tension. And it's like we're not even there. Not even present.

I said this, I've never had anything go viral. It's probably the closest anything ever came. I was having a moment. I was on a business trip in New York. I was feeling quite down about some things, and it dawned on me, you talk to most people who've worked with me over, I don't know, let's say 10 years. 

They're going to say a bunch of really flattering things. "Michael's so charismatic, he's dynamic, he's smart, he shows up, he goes to any dinner meeting. He will do whatever." But they're getting the best version of me. They are getting the absolute best cut of the meat.

The people that matter the absolute most to me, my number one prized possession, my family, they get the worst fucking version of me.

And then in the morning and at night when you're tired and you're exhausted, your family's getting the tired version of you, the stressed version of you, the beat down version of you. And so I was feeling absolutely horrific that the people that matter the absolute most to me, my number one prized possession, my family, they get the worst fucking version of me. The worst. 

And they deserve the best. And the reality of it is is that when I had this moment and I had this epiphany, every household is like that. Every household is getting the worst versions of each other.

And try to be kind to each other under that environment. You're beat, you are exhausted, you're drained, you've had a hard day. People are demanding. You're trying to navigate the challenges of life. And then the person who you made a baby with, the person who you love, the person who's going to be there for you when you're sick, the person who's going to miss you when you're gone, they're getting the shit version. 

I'm obsessed with trying to figure out how I can fix that for my own family, first and foremost for my own wife and kids. And if I can build some sort of technology that tries to scale that, cool. But if not, that's okay too. I'm focused right now at a professional level and at a personal level of building the right balance to show up in the right way for everybody. I hate myself sometimes so deeply for being a great boss and being a shitty husband.

Well, the mission you're on, it's awesome. And the parenting journey, everyone's trying to figure it out. Everyone's like, "Oh, look at these people." But behind the scenes you know it’s chaos! You see these perfect photos of snapshots and destinations.

You find out that many of these supposedly happy couples and families, they get divorced, and it's like, hang on a sec. You were telling me how good your life was for the last five years and all this stuff was perfect.

Exactly right.

I think it's really hard going to school and not getting good marks. And I think it's really hard building a business when people think that you're stupid. And my mother used to always say, "Do not seek external validation. Find internal validation."

In my hardest moments, I was like, "She's so right." And in a very weird way, we are using Instagram to seek external validation. We use Twitter to share our mind, to seek external validation. We use thought leadership pieces to seek external validation, but what are we doing internally? By internally, I mean our family.

On your best day, what's an affirmation that you would write on a flashcard that you could show yourself on your worst day?

Be thankful.

Final question, what's one thing you do to Win the Day?

Find gratitude.

Michael, thanks so much for coming on the show.

Thank you, James, for having me. I appreciate it.


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