Dad Life

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Pop quiz: What do Jeff Bezos and I have in common?

Well, other than having a face only a mother could love, we both invest heavily in Contemporary Art. Great minds really do think alike

Jeff has $70 million held in contemporary art right now and if Jeff’s betting big on an asset class, he’s expecting a solid payout. My allocation to art might not be as big as Jeff’s...but, I’m a much better art investor than he is ( I think). I’ve already got a Warhol, Banksy, and a Basquiat in my portfolio, thanks to Masterworks.

No, I didn’t need millions to buy entire paintings like Jeff, because Masterworks has fractionalized masterpieces from the untapped $1.7T art market for me. 

Contemporary art prices returned 14% on average each year from ‘95 to 2020, compared to just 9.5% for stocks. Add some compounding growth magic, and bang, art outperformed stocks by nearly 3x. I'll be adding more art to my portfolio in October - so join me on Masterworks with this special Not Boring link today.*

Hi friends 👋, 

Happy Monday! It’s a big day for a little man today, so this one’s going to be a little different.

We’ll be back to web3, startups, and investing next week. If you want your fix, I linked to three Not Boring Founders episodes down below.

Let’s get to it.

Dad Life

Today is our son Devin’s first birthday. Happy birthday Dev! 🥳 

You can’t read yet, but maybe one day in the future, when you get in trouble, we’ll make you read all of my old newsletters as punishment. If you’re reading this, then, don’t do whatever you just did again. 

I was planning to put my head down and write a piece to send like I do every Monday, and I was about 60% done, plenty far enough to finish if I spent most of the day Sunday like I always do, but we had his birthday party yesterday, and our friends and family were in town, and I realized that enjoying that with him and Puja and everyone was so much more important than rushing back to the computer to get a normal newsletter out. 

A year ago, I would have been terrified to go off course for a week when momentum is strong. I feel deeply accountable to all of you to send a newsletter out every week, to the sponsors who make Not Boring part of their marketing plans, to the founders I’ve backed and to the LPs who’ve backed me. The sheer numbers on that side of the aisle are overwhelming. It can throw my perspective out of whack, push me to work seven days a week every week. But there’s only one person out there depending on me for his survival; the rest of you will be fine for a week. 

Growing a business and growing a kid in the same year has been an incredible, intense ride. Instead of a normal piece this week, I thought I’d reflect a little bit. It might be fun to read this together in four, nine, twelve, fifteen, or seventeen years, on some big birthday milestone in the future. Plus, I’ve read a lot of pieces about being a working mom, but fewer about being a working dad. Thanks to work from home, more dads are getting to be a bigger part of their kids’ lives, which is both the greatest thing in the world, and hard. I’m throwing my thoughts in the ring in case they’re helpful to anyone trying to balance it all and feeling constantly behind. Me too. 

(As if he knew I was writing a full Not Boring on Monday morning for the first time ever, or maybe out of excitement for his birthday, or probably because he had pizza and ice cream for the first time yesterday, Dev decided to stay up most of the night last night for the first time in a long time. I blame any cheesiness below on dad brain.) 

First things first, I know we’re incredibly fortunate. The most amazing thing about this past year has been that we’ve both gotten to spend it at home -- whether home was in New Jersey with Puja’s parents, at the shore with mine, or back in Brooklyn -- with the buddy. I always just assumed that whenever I had a kid, I’d have to leave in the morning, go to an office every day, and try to make it back in time to read him a book and put him to bed. That’s if I was lucky and didn’t have to travel. 

My dad had to travel for work all the time when I was little. A couple weeks ago, he told me the story of flying to Miami for a morning meeting, flying home in the afternoon to take me and my sister to the St. Dennis Fair in the evening, and then waking up the next morning at 4am to get back on the plane to go down to Miami for the next day’s meetings. That wasn’t unique; I distinctly recall day trips to Germany. At the time, when I was like ten, I thought that was so cool. Who else’s dad popped over to Europe for the day? Now… I can’t even begin to fathom how exhausting that must have been. And I can’t imagine how challenging it was for my mom to raise me, and then my sister and brother, while working, and then getting her PhD and starting her own business at the same time, while my dad was traveling. Every bit of work ethic I have comes from both of them, and I feel very soft when I think about how much they did versus how much I do. Getting on a plane every few months, or watching Dev on my own for an afternoon, and then sitting in front of a computer and writing wipes me out. 

It’s hard to fully appreciate your parents until you become one. 

Either way, it was a foregone conclusion in my mind that I’d miss things like first words, first steps, first everything. That’s just what working parents do. If you want to provide for your kid, that means not seeing them sometimes, and trying to be successful enough that you could maybe set your own schedule at some point when they’re a little older, maybe even retire early. COVID has been terrible for a billion reasons, but personally, the silver lining has been not needing to make that trade-off. Work and home are the same thing. 

We’ve gotten really lucky. At the beginning of the pandemic, I’d quit my job, shuttered the company I was trying to build, and was an unemployed newsletter writer with fewer than 500 readers, all free, and no income. We’d just found out we were going to have the baby futurely known as Dev. It was a scary time to bring a kid into the world, globally and locally. Puja was thinking about taking a new job at a startup, and we had to spend a lot of time thinking about whether it made sense to give up her healthcare with a kid on the way. But we got to live with Puja’s parents when Dev was born, and spend a lot of time with my family. I got to work from the basement rent-free while I was income-free. And I got to pop upstairs every time I wanted to see the little man. 

Dev got to spend most of his first year really getting to know his grandparents, and his Aunt Meg and Uncle Dan. Now that we’re back in Brooklyn, Meg has come home from Ghana a few times and gotten to spend time with him; she stayed with us a couple times in the past week and wakes up with him in the morning like a saint. Dan and Sienna live in New York and come over every Sunday. Puja’s parents and/or mine are here practically every week. 

Balancing everything is still challenging. I sent a newsletter four days after Dev was born and have worked practically seven days a week straight through. In April, I launched Not Boring Capital just to up the degree of difficulty. I’ve never worked harder in my life. I feel like I’m dropping balls everywhere -- when I’m working, I’m not being as good of a dad or husband as I could be; when I’m taking a break at 4pm on a Tuesday to take him to the playground with Puja, I’m not working hard enough. 

There’s a reason that world-changing companies are often built by young people: it requires a maniacal focus and the ability to put everything into a company. I’m not willing to do that anymore. I’m constantly turning down in-person meetings, dinners, and other time-consuming things that would probably be good for my career but would mean less time with Dev and Puja. At least when the baby is little, I think you can choose two of three:

  • Good parent

  • Career growth

  • Social Life

I’m trying to be a good dad and grow Not Boring and Not Boring Capital. That means trading off a social life for now, which I’m totally cool with, and not being nearly as responsive as I should be to email, texts, DMs, etc… which I need to get better at. If your email is sitting somewhere in my inbox unread, I’m sorry 😬

Puja is an absolute hero -- an incredible mom, a natural, on top of everything when I’m absent-minded, consulting, running her own company, and still making time to hang out with friends and family. She does more than I do, actually does three out of three, and makes it look easy, even though I know it’s not. She blows me away. I’m so happy Dev is picking up all of her incredible qualities (including, thankfully, looking more like her than me). 

The first time he was on Invest Like the Best, Sam Hinkie said, “I think it's the single biggest decision of your life and I don't think it's close, who you choose to spend your life with.” There are a couple of reasons for that: first, because you’ll spend the most time with that person, and second, because that person will contribute 50% to your kids’ … everything. Your kids will be half you, and half your partner. When I listened to that podcast, we weren’t parents yet, so I kind of got it conceptually, but it’s really struck me over the past year how right he was. I see so much of Puja in Dev, and love watching her be his mom more than anything. 

And then there’s Dev himself. The kid is unbelievable. When you’re pregnant, everyone tells you how hard it’s going to be. It’s kind of like pledging a fraternity, they say, the best thing that you’ll never want to do again or something. They tell you that for the first few months, the kid will just be a blob. That it’s boring. I don’t think we felt that way for a single day. He’s had his own personality from the beginning, and even when he was just a couple weeks old, you could tell that there was something going on behind those wise brown eyes. 

It’s all gone into hyperdrive recently, though. Even though he’s only one, you can already tell that he’s kind and funny and smart and driven. He shares his pacifier and his bottle with us even though he wants them so badly. He’s the most determined kid I’ve ever seen. He won’t stop until he gets what he wants. He laughs, he walks, he’s starting to talk. Last week, he parroted blue, yellow, and notebook (we’ve been watching some Blue’s Clues). He says mama and dada like he knows what he’s talking about. He’s like a little grownup in a baby body. 

Even now, just a year in, I have an idea of what he’ll be like as a kid and even kind of as a grownup, which is wild. I can’t wait to see the little man he turns into, and then the bigger man he turns into after that. When I see teenagers starting companies or making NFTs or doing anything impressive-beyond-their-years, my first thought is that Dev will be doing some really incredible things really young. When I see companies like Primer or ClassDojo or Replit, I get so pumped about all the ways Dev’s going to be able to learn. I thought the idea that you want your kids to be smarter and more successful than you was bullshit before I had one, but now I want that kid to blow me out of the water.

I’m like the Steve Buschemi, “how do you do, fellow kids?” old guy of web3, this stuff will be native to him. Or maybe he’ll be onto web4 and roll his eyes when I talk about web3. I’ll ask him to do a TikTok dance, and he’ll roll his eyes and say, “TikTok is for Zoomers.” We’re going to inevitably hit a point when he’s explaining the latest trends to me; if Not Boring survives for another decade, it’ll likely be Dev behind the scenes telling me what to write about, and correcting my embarrassing use of old terminology. Thanks in advance. 

But I don’t want to wish away the present. Right now is pretty spectacular. Even when I’m working every day, I get to wake up with Dev in the morning, take him for a walk, pop downstairs and hang out between meetings and calls. If he takes a step or says a word, I can drop what I’m doing and go see it for myself. We get to hang out as a family every day. I get to give him a bath and put him to bed every night. That wouldn’t have happened if we weren’t working from home, or if I weren’t working for myself. None of this would be possible if Puja weren’t holding it all down. Dev’s so lucky to have her as a mom, and I’m so lucky to have her as a (much-better, more than equal, far superior) partner. 

The first year with Dev was the best, and the best is yet to come. Happy birthday little man.

Not Boring Founders

If you want some startup and NFT content to carry you through the week, I got you. I’ve been experimenting with a new podcast, Not Boring Founders, where I interview founders in the Not Boring portfolio. I want the vibe to be “casual conversation with the mics turned on.” We’ve broken both of those rules three episodes in — one podcast is with the founder of an NFT project that hasn’t taken VC money and another is a fireside chat with — so expect that we’ll break them often, but the goal will remain constant: giving more shine to the people building the future.

We’re going to keep doing more of them. Check out our last three episodes, subscribe, and review (working on audio quality! feedback on the content is appreciated):

Nick Greenawalt, Wanderers

Reed McGinley-Stempel & Julianna Lamb, Stytch

Chris Toy, MarketerHire

Thanks for reading (and listening), and see you next week,


*See important disclosure