The Coffee Chat (#55)
My conversation with Brett Rounsaville - Former Disney theme park designer, Amtrekker who fired Trump on National TV, Founder Yes, More & Co and Dad to two girls!
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Hi there 👋🏽
I've always resonated with the idea that life should be filled with constant motion. Stillness? It has never been my thing. From a young age, I've had this insatiable craving for action, for getting things done. I pride myself in being a thinker and a doer, with a relentless bias towards action.
Yet, in 2024 I wanted to do something different. I wanted to test out this new idea of not having any resolutions but just a word that I embrace and live. I found myself embracing a word that's seemingly at odds with my nature: "Unrushed." It's become my mantra, both personally and professionally.
Over the past two months, I've embarked on a journey of self-discovery, one where I've consciously slowed down. It's a stark departure from my usual whirlwind pace, but it's been transformative.
I find myself healing a part of me that was maybe damaged?!
I am grabbing fiction books, listening to music rather than just podcasts, and reconnecting with old friends through phone calls.
Feeling unrushed doesn't mean I've abandoned my ambitions or goals. Instead, it's about approaching them with a sense of grace and patience, understanding that the journey is just as important as the destination. It's about finding balance in a world that's constantly pulling us in a million different directions.
In a world that's always rushing forward, I am trying to find the courage to pause, to listen, and to embrace the beauty of being unrushed.
☕ Now, on to today’s coffee chat…
Meet Brett Rounsaville
Thanks to this newsletter I have met some impressive folks but hands down Brett is one of the coolest! Through our whole conversation I kept telling him - OMG you have led such an interesting life.
Brett started out as theme park designer for Disney.
Then left that behind to go on a crazy adventure - Over a two year period of time he travelled across America and crossed every single item off his bucket list. Here is him being interviewed on Good Morning America where he tells Donald Trump you are fired! He was referred to as the “Amtrekker” and was a legit micro celebrity.
Then at some point he found himself working at what was once called Twitter and witnessed Elon Musk coming in to change it to X!
And now he is the Founder / CEO of Yes, More & Co, a platform to make shopping from small brands fun again.
Brett at some point I am sure will write a book. There are just SO many amazing stories in him.
Below is my conversation with Brett…
Please tell us a little bit about yourself and your family
My name is Brett and I have two girls, five and seven and as of last year September, they both go to the same school and that is the most magical piece of parenting I've experienced yet. One drop-off, one pickup and we are saving tons of money on childcare - all of a sudden it feels like we got a raise.I am trying to tell myself - 'Don't get excited. You're still a parent.' but it's crazy how many problems that get solved now that both daughters are going to school - we save an hour plus a day, and then the little girl comes home extra tired so she sleeps better, and she comes home extra hungry, so she eats better. It's been magic. I highly recommend letting your kids grow up.
Professionally, I have a very unusual background. I started my career as a theme park designer for Disney. That is all I ever wanted to do from the time I was eight until I became a designer for Disney in my early twenties. I worked there for a while, and then I left because I made this list of 50 things I've always wanted to do. And I told everyone I wasn't going to come home until I did all 50 things, and I wasn't going to spend any money on lodging while I was gone.
And so I thought I was taking like a month-long vacation, but it took me two years to do all 50 of those things. And that was two years of like sleeping on park benches and bus stations and train stations and strangers' couches. This was 2007-08. It got really big also because it was the same time when the video iPod came out and I was doing a short documentary podcast once a week and then writing about it five times a week. So I was a content creator, well before there was a way to monetize being a content creator!
Once I was done with that adventure I stumbled into the startup world - I joined a startup that made these enormous real-world adventure games. The founder of that company gave me my first money to build my first startup, which was an iOS app. It was a camera app with a game layer - every day, everyone would get the same new mission. Take a photo that satisfies the mission, and then the community votes the photos up and down and creates leaderboards of awesome photography. Still super proud of that product. It was highly rated but had a really small audience, and it stopped growing at about 10,000 users, and so I ended up shutting that down in 2019.And then similar to the whole world life changed considerably during the pandemic. So when the pandemic started, I was mostly just a dad on the couch who was kind of happy with being a dad on a couch. And then I realized I was going to be trapped in my house with two little girls. So I tried to front-load some birthday presents by going to a local toy store and buying a couple of things that monsters could play with.
And it turned out that the toy store was closed, obviously because it was a pandemic. Every time I would take my dog out for a walk, I would see all the shops closed, not knowing where the next sales were gonna come from and stuff. I had a very blue-collar upbringing where my parents owned their own business - an upholstery shop. Maybe that is why I could not really see these people struggle because I saw my parents in them and felt I had to do something to help.
The way I handled that guilt was I drew a circle around my house and I started calling every retail business in Oakland and making friends and generally trying to figure out if there's a place where their problems intersect and my skill set at some point. And I hit on this idea that I wanted to create sort of a hyperlocal Amazon where you can buy whatever you want online. It all shows up your door in a couple of days.
That is when I stumbled upon what April Underwood was doing - she was trying to solve the same problem in a different way. We started having like regular zoom calls and sharing information and then one day she announced that she raised a bunch of money and asked if I would like to make our paths converge, and so I quickly grabbed onto her coattails and we started building a few different things. But eventually it became the company known as Nearby. To be clear she was very much the founder and I was very much employee number one! Eventually that company was acquired by Twitter.
I feel like I've lived like six lifetimes…
Please go on…I am literally hooked. So you saw Twitter change, right?
Twitter was bonkers.
I have so much to say. I might just write a book.
And then I left Twitter, the end of November 2022. I don't know how closely you follow the news, but I was one of the people who decided not to click the hardcore checkbox. Once I left Twitter, I basically jumped straight into my next venture l, raised funding and started Yes, More & Co, a platform to make shopping from small brands fun again.
Oh wow. What a fun interesting life you have lived! Tell me more about your partner?
My wife - She is awesome. She's so much so much more impressive than me. We met in high school - essentially we went to high school together, we were not like high school sweethearts or anything. Just great friends who kept in touch through college and then during the time I was bouncing around the country she was following that trip and in fact decided to do one of the things with me which was hike to the bottom of the Grand Canyon! That was our first date She is now a nurse and works with a large multinational pharma brand in their quality team to ensure things do not go wrong in a hospital setting.
She is also a multi-time Ironman, has run more marathons than I can count and certainly a better parent and a better friend than I am. She is good. I like her.
Your daughters are so lucky. Both their parents are such interesting people living such full lives. What great role models. So many of us live our lives in such narrowly defined little boxes that it is so nice for them to have a mom and dad who are truly multi-faceted …
That is super insightful. I like that.
And we are just about starting our conversation! I have so many questions. I think it's fascinating that you went ahead and actually did this whole I am going to do these 50 crazy things. What pushed you to do it? I feel like a lot of people come up with bucket list in their younger days but don’t really do much about it. I'm curious, what was that trigger where you said - Hey, I'm going to actually go and live this life and do these 50 crazy things?
Important part is that this predates even the term bucket list. So the movie had never come. Three factors came into play. First, both my sister and a coworker made 50 lists around the same time, and I thought, What a novel way to center yourself and decide what to do next. Secondly, I found myself needing to make decisions about my future. Since I was eight years old, I had set my sights on becoming a theme park designer. I had moments of inspiration, worked towards that goal for 16 years, achieved it, but then felt empty. Although I loved my job, it was highly competitive, and there was little room for advancement. It was a dream job. But also, it was a lot of people's dream job and so you had to wait for people to die in front of you before you could move up in the company because just no one was going to leave that job anytime soon.
Between knowing that there was no chance for advancement, knowing that accomplish this huge goal that I'd been working on forever, and then having this example put in front of me of like being able to center yourself with this list really drove all of it and then I made the list printed it out and put it on my kitchen table.
And then just felt like an idiot every single day. Every day I saw this list and it was all easily accomplishable things if I just decided to go do them. And I wasn't deciding to go do them. I was just like going to work every day. I wasn't even like taking a weekend off to do one of the things on the list. One day I told myself I have to take a month long sabbatical and just do this list. Of course, one thing led to another it did not take a month, instead it took a long time! I was clear I was not going to go take another job till I just did all 50 things
So, we've been chatting for about 20 minutes now, and I've gotta say, you strike me as quite an interesting person. You know, the kind of person who'd be the center of attention at a party. Most of us, we get so caught up in our roles as parents or employees that we sort of lose that spark. But you, you seem different. You still have that twinkle in your eye, and you're out there doing quirky, fun stuff. Have you ever thought about how you manage to stay interesting after becoming a parent? Is it something you consciously work on, or is it just who you are, Brett?
Well, here's something I'd like to emphasize to you and everyone out there: It's important to recognize that what you see of me, or anyone else for that matter, is just the highlight reel. You're comparing that to your behind-the-scenes footage, and let me tell you, it's still a grind every single day. But maybe what sets me apart a bit is my knack for breaking things down into micro tasks. I'm pretty good at taking big goals and breaking them into small, manageable steps, and I'm okay with making just a little progress each day.
For instance, I once dreamed of being a theme park designer, but now I've been knee-deep in e-commerce startups for the past five years. I've drifted away from that world in ways that sometimes leave me feeling a bit unsatisfied. However, I've found ways to scratch that creative itch, like working on my daughters' Halloween costumes every night for the past month. It might not seem like much progress each evening, but looking back, it's rewarding to see how those small steps add up over time.
This mindset applies to everything in life. Even with the company I'm recently founded, it's been a year and a half of tiny, incremental steps before I even considered raising funds for it. Sure, things have picked up speed now that I have a bit of investment and a team working full-time, but it's those initial baby steps that laid the groundwork for where we are now.
I really believe in just doing things, taking micro steps and the power of compounding
So, another thing that strikes me as interesting about you is your tendency for self-reflection. In a world where so many people get caught up in labels and identities, you've walked away from some pretty significant ones, like Disney and Twitter. It seems like you've really taken charge of shaping your own path. Has becoming a parent influenced this self-authorship journey at all? Did it change how you approach life, take risks, or handle uncertainty? I'm curious if fatherhood has prompted any shifts in your perspective or approach to life decisions?
Oh, absolutely, fatherhood has changed me. Legacy is everything. Those little steps I mentioned earlier? Well, they've gotten a whole lot smaller now. Every task I manage to squeeze into a day feels like a tiny victory. But there's also this intense drive to prove yourself to your children, you know? To do something that they can look up to and be proud of. It's funny, but that drive is even stronger for me than doing things I can be proud of for myself. I remember when my first daughter was born, I felt this overwhelming pressure to document every moment, every adventure, those first two years of her life. So not long after she came into the world, I ended up writing this whole manuscript, went through the whole process of finding an agent, tried to sell it to publishers—22 rejections later, but hey, I gave it my all. And you know what? It was all fueled by this immense desire to be worthy of my child. And that feeling hasn't faded, even now that she's seven. I still feel like I have to earn her respect every single day.
So, when you talk about earning respect from your kids, what exactly does that mean to you? Because for some folks, respect might come from climbing the ladder in a growth startup or becoming a partner in a law firm. But then there are others who would argue that coaching your kid's Little League team or being there to cheer them on at soccer games is just as respectable, if not more so. It's all about different perspectives on what it means to live a fulfilling life. So, when you think about this idea of earning your kids' respect, how do you personally define that? What actions or values do you prioritize in order to achieve it?
That's a really thought-provoking question, and honestly, I'm not sure I have a perfect answer for it. But let me try to unpack it a bit. I believe there's a part of me, and probably any entrepreneur for that matter, that feels a bit broken inside. It's like this inherent drive to create something, to fill a void or fix something within ourselves. For me, I think it traces back to my early fascination with Disney. I mean, even as a kid, I was amazed by stories of Disney building his own camera and animating in his garage. It was like this idea that you could start from nothing and build something extraordinary. But then, with the internet coming into play, it felt like that kind of grassroots innovation was lost. However, as I've grown older and seen what the internet can offer, it's like this renewed belief that anyone can create something meaningful, even from their garage, metaphorically speaking. It's like saying, "Hey, if they can do it, why not me?"
But here's the thing about confidence - I'm not inherently confident in myself, nor do I believe anyone else is. We're all flawed, imperfect beings. Elon Musk, Jeff Bezos - they have their own insecurities just like the rest of us. But they've managed to accomplish incredible things, sometimes by just taking small steps repeatedly and being okay with that. So, when people ask me where my confidence comes from, it's not about me being super sure of myself. It's about knowing that even flawed individuals can achieve remarkable feats, and sometimes it's about embracing those flaws and taking those small steps towards something bigger.
Changing gears a bit, you mentioned your current venture is this idea of making everything easier. You mentioned how life can be tough, and you're on this mission to simplify things as much as possible. Could you share some practical strategies you've adopted to, let's say, enhance efficiency or streamline your daily routines? I mean, let's be real, as a parent, time is precious, and finding moments for yourself can be a challenge. Have you and your partner implemented any specific tactics or changes in your household to minimize friction and make life run more smoothly? Like, besides the obvious stuff like having your kids attend the same school, are there any other adjustments you've made that have significantly eased the day-to-day grind?
Yeah, I'd say the biggest change we've made is being intentional about not overloading our kids with a bunch of different activities. We try to limit it to just two activities at a time for each of them. Right now, it's soccer and ballet, although ballet just wrapped up last week, so it's just soccer at the moment. And the key is that we've steered them towards doing the same activity whenever possible. So instead of running around to different practices every night, we have set days like Tuesdays for ballet and Thursdays for soccer, where they both participate. This way, we have more days in the week to spend as a family or tackle things at home. It not only simplifies our schedule but also allows us to enjoy more family time together. And speaking of home, we make sure to use that extra time for little tasks that make the next day smoother, like pre-packing lunches and snacks. It's all about finding ways to streamline our routines and maximize our time together as a family.
And what are things that energize you? How do you regain your energy? What do you do for self care?
Nothing gives me more joy than creating something from nothing like that. That zero to one process, whether it's like starting a company or making the kids Halloween costumes that brings me so much joy.
Makes sense. So, I guess that's why you keep yourself busy with these little projects, right? It's like your way of tinkering. Becoming a parent is a pretty monumental life change for most people, and it often leads to discovering new things about yourself that you might not have been aware of before. So, after becoming a dad, what have you learned about yourself that perhaps wasn't so clear to you before?
Oh, my goodness, the biggest revelation for me has been realizing that I'm not as patient as I once believed. I used to think I was the epitome of calmness, but then, when you have a child, metaphorically speaking, who is genetically programmed to push your buttons, you realize you're not quite as zen as you thought. Don't get me wrong, I still consider myself a pretty patient person, but it's been eye-opening to see my limits.
And as for structural changes, it all comes down to this drive to be worthy of my kids. That's been the driving force behind most of the adjustments we've made
Are there any commonly shared parenting tips or advice that you think people should take with a grain of salt?
I think one of the most crucial aspects is having a strong partnership with my wife. So, my advice tends to lean more towards marriage than parenting per se. One piece of advice about marriage that I always cringe at is the whole "never go to bed angry" thing. Personally, I'm all for it – if you're angry, sometimes it's best to just hit the hay and deal with it in the morning when you're both refreshed and level-headed. As for parenting advice, well, I don't believe in a one-size-fits-all approach. Every child is unique, with their own personality, and every parent brings their own set of traits and values into the mix. So, there's no magic bullet solution. What works for one family might not work for another. It's all about finding what works best for you and your family and being respectful of the fact that not every piece of advice out there will suit your situation.
🤓 Open tabs…
(I have modeled this section after those “open tabs” that we all have with a few (okay 30-40) interesting links that we promise we will eventually get to one day. These are the links that I had open for sometime that I finally got to …)
⭐ Grace Puma shares how working women can shatter the glass ceiling
Puma has developed a framework for answering these questions, which she calls the SOAR method:
Self-assessment: Think about the strengths you’ve already got under your belt and those that you need to develop further.
Opportunities: Keep an eye out for paths to broaden your skill set.
Action: What do you need to do to create growth opportunities for yourself?
Red flags: Think through the obstacles that might pop up in your career and derail your growth, having a plan B at the ready.
⭐ How America Became Addicted to Therapy (🎧)
Therapy is so destigmatized now that a lot of us sound like therapists. We’re “codependent,” “triggered,” “catastrophizing.” We cut off our friends who are toxic. Justin Bieber doesn’t fear an exposé on the damage of childhood fame; he freely discusses his trauma and healing. Oprah wonders what happened to you. And once you figure it out, you’ll find hours of free advice on TherapyTok.
Friedman, who has been teaching and seeing patients for more than 35 years, is pleased about the new openness. But he’s also worried for us. Treating therapy as routine has led to the “medicalization of everyday life,” he says. On this week’s Radio Atlantic, Friedman proposes a radical idea: A lot of people could probably quit therapy.
⭐Tired? Distracted? Burned-out? Listen to this (🎧)
Your life, after all, is just the sum total of the things you’ve paid attention to. And we lament our attention issues all the time: how distracted we are, how drained we feel, how hard it is to stay focused or present. And yet, while there’s no shortage of advice on how to improve our sleep hygiene, or spending, or physical fitness, there’s hardly any good information about how to build and replenish our capacity for paying attention.
📖 My private thoughts from my very public diary…
(Sometimes on X (Twitter), sometimes on Threads)
I would love to hear from you, feedback is always welcome!
And if you happen to know an inspiring working parent who should be featured in a future edition (or if you yourself are one) - please do get in touch
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Disclaimer: All views expressed are my own and do not necessarily reflect the views of my employer