Hello friend,
Why you're getting this: this is my Friends Newsletter, a brain dump of interesting things that I send to interesting people I've met and friends I want to stay in touch with. Zero pressure to stick around—just click unsubscribe if you don't want to get it (don't worry, I won't be notified).
We talked about:
It's a fun one. Listen here: YouTube / Spotify / Apple Podcasts
Zoe's sister Ariele and her friend Lina were visiting the other weekend when Ariele casually dropped this compliment.
I immediately leaned in and wanted to know more.
If I have one passion in life—maybe even an addiction—it's making new friends.
Most people want money. A nice car. A flashy watch. A beautiful house.
Why? Because they think if they get those things (money, success, an impressive outfit), it will somehow translate into the life they dream of.
A life where they have a great partner, interesting friends, and a community that welcomes them.
They crave connection—they just try to get it in the wrong way.
The reality is that building the connection we all crave doesn't require money, success, or fame—in fact, those things often get in the way of it.
Instead, building friendships and community simply requires openness, warmth, and consistency.
After decades of striving for the other stuff, I've come out the other side and realized that my goal in life is really just to have great relationships and a strong community.
If you can build a life that revolves around friends and family (plus sleep and exercise), you have most of the key ingredients for a wonderful life.
Science backs this up: decades of studies like the Harvard Study of Adult Development show that close relationships are the strongest predictor of long-term health and well-being.
I've always been lucky that making friends comes naturally to me, but one thing I've struggled with over the years is creating cohesive groups and communities.
I've always been jealous of those people who have a "crew".
You know the ones.
If you aren't one of them, they're very irritating.
I've always had a wide ranging group of friends. I can pretty much land in any major city in the world and have coffee with a pal.
But where I've previously failed is creating cohesive groups.
In the past, I had a million disparate relationships, but few collections of people that I'd feel confident inviting over to my house without feeling low-grade anxiety.
I asked her how she builds friendships. She told me her secret:
"Whenever I go out for a group dinner, pickleball, movie, whatever—I always create a group thread and give it a funny name. Then, if I like the group, I just keep texting the group thread. Before you know it, everyone gets comfortable, chemistry gets built, and then you have this little crew to do stuff with."
So simple.
Something that takes almost no effort—but when I thought about it, I realized many of my favorite friend groups had formed the same way: purely by accident, through group text threads.
It's a great trick.
But here's what I've realized: while Lina's group text move is perfect for sparking new friendships, it only gets you half of the way there.
The real magic happens when those spontaneous hangouts become intentional and structured.
That's why, in my own life, I'm focused on creating rituals.
Rituals are things you do over and over again, typically with the same group—the glue that turns strangers into friends, and friends into family.
As you get older, life gets busy.
Unlike in college, community doesn't just happen anymore.
If you aren't intentional about building friendship, you flat out won't.
You'll go to work. Come home. Put your kids to bed. Occasionally have a double date with another couple. Go make small talk at soccer practice and ballet.
You know. Life.
Those things are all fine. But they often don't create true community and relational depth.
To build a deep friendship, you need reps.
You can rarely go deep in the first few hangouts. It takes time to get to know one another.
The same is true of groups. I've been in business forums—confidential support groups where we talk through personal, family, and business issues—for almost twenty years. That's where I first discovered the power of rituals.
A group of six of us meet once a month and attendance is mandatory. Unless your kid's in the ER, you come.
We each prepare updates, sharing highs and lows from our personal, family, and business lives, and take turns sharing our updates one by one.
When I first joined one of these groups I thought it would suck.
What did I have in common with all these people anyway?
They all ran businesses in different industries and to be honest, I didn't think I really clicked with most of them.
Flash forward twenty years, and my forum mates are some of my best friends.
What made it work was the consistency and structure.
It became a special ritual—something I did every month—and over time we got insanely close.
So, over the last few years, inspired by the success of my forum, I've focused on building more recurring rituals.
These are my current ones:
I've now expanded to four different groups of 6 people. Each meets once a month, so I do one per week
I find this creates weekly time to catch up with my friends while adding structure that pushes us to talk about deeper issues. It's part bullshit session, part group therapy, part business strategy.
My forums have resulted in some of my deepest, highest trust friendships and years of incredible laughs, group trips, and inside jokes.
I play 2-3 times a week, and I have an ever-growing group thread that we're always adding random friends of friends to.
It's great exercise and a fun way to casually get to know people I'd never meet otherwise.
I rent out a restaurant once a month and invite a broad range of local entrepreneurs to have lunch.
We share recent wins and struggles, introduce anybody that's new, and then sit down for lunch with no small talk allowed (we use conversation cards to prompt people to talk about deeper stuff).
ELC has created a lively community of local entrepreneurs who can band together to solve problems and connected a bunch of my favorite entrepreneurs who wouldn't otherwise know each other.
Once a year, I invite all my most interesting friends from all over the world to hang out together in Victoria for three days.
I call it Interesting People. It's not a conference—it's 100% focused on getting everyone to click and get to know one another.
I run it with my friend Nick Gray, who literally wrote the book on creating events that create connection and I can safely say that it's unlike any event you've been to.
I joke that Interesting People functions like FedEx: once a day, all of their delivery planes land in Anchorage, Alaska and swap packages. This masterful coordination gives FedEx the ability to deliver packages anywhere in the world within 24 hours.
IP is an opportunity for me to do the same with my entire network of friends from across the world. Doing so always results in good things: new friendships, business and creative partnerships, and a tribal community.
A few friends and I recently started Sunday—a secular group that takes the religion out of church while preserving everything else.
I've always envied my religious friends. They just seem happier. But I don't think that joy comes from biblical stories—I think it comes from the ritual itself.
Every week, they get a built-in moment to pause, zoom out, reflect on life, and connect with their community.
So, we decided to build that same structure, minus the religion. Sunday is our weekly gathering for introspection, gratitude, and community.
If you're in Victoria and interested in joining, send me an email.
Every August, me and a bunch of my dad friends rent out a summer camp for a few days with our kids.
It's the ultimate win-win: the kids make incredible core memories together and become buddies, our partners get a break, we all take time away from screens and work, and I get to introduce my dad pals to one another.
I just started doing special 1-on-1 trips with each of my boys once a year.
Last week, I got back from a trip to Disneyland with my oldest son, and just looking at the photos makes me feel like I did some low-dose MDMA. I keep realizing that I only have 10 years left—at most—for special stuff like this, and the hourglass is almost half drained.
The days are long, but the years are short, and between this and Camp Dad, I feel like I've started building some core memories for the boys to lean on when they're older and I'm annoying them at family dinners.
All of these rituals have created their own unique cohesive group or community (including a group text thread) and have meant that I have a social scaffolding where, if I just follow my calendar, I will naturally spend a ton of time connecting with the people I love.
It requires a bit of advanced planning, but once you're in the groove it feels effortless to have a vibrant social life. And it all starts with a group thread!
What about you? Got any good social tricks or rituals? Reply to this email, I'd love to hear about them.
'Rich Men North of Richmond' by Oliver Anthony (Spotify).
If you haven't heard it, you should listen. I get tingles up my neck every time I listen.
If you study history, there's this recurring pattern—what Robert Greene would call the cycle of generations.
Every few decades, the pendulum swings. The establishment tightens its grip, the next generation pushes back, and suddenly you get an explosion of extremes on the left and the right. Rebellion, control, and chaos.
You see it today. Black Lives Matter, the trucker convoys, the campus protests, assassinations, the rise of populism and conspiracy theories.
As Mark Twain famously said, history doesn't repeat, but it does rhyme.
And right now it feels like we're rhyming with the late 60's/early 70's.
Back then, that tension produced some of the best music of all time. Protest music about what was happening in the country.
I'm thinking of songs like:
These songs are all incredibly melodic middle fingers to the system.
But unless I'm missing something, we are in a similar time right now and yet this type of music seems to have vanished.
Where are the Trump protest songs? Who is our generation's Bob Dylan or John Lennon?
Sure, people post their outrage on TikTok, but where's the SONG?
A song so good that even the most ardent Republican father can't help but sing along to it as he drives his kids to school.
This Oliver Anthony song feels a bit like that.
I don't know what it's like to grow up in poverty in the American South, and I doubt I align with his politics, but I can't stop listening to it.
It's so moving. I can't imagine that anyone with a heart could listen to his voice cracking and not feel something towards the struggling working class people he's singing about.
More songs like this, please.
This is the story of one of my most spectacular ones.
The story of how I lost ten million dollars by doing something stupid.
This week, with quivering, shell-shocked hands, I signed documents that hammered nails into the coffin of my greatest business disaster of all time.
We finally shut down Flow, the productivity software company I started back in 2010.
I lost over ten million dollars in total.
Ten. Million. Dollars.
Up in smoke. Money bonfire. GONE.
For reference, if I'd just invested in an S&P 500 index fund with that cash, it would be enough to retire with $300,000+ in annual passive income.
Even worse: it would be worth over $30 million today.
In 2009, Metalab was a small but profitable agency.
The business was making a couple hundred thousand dollars a year in profit and I was trying to figure out how to invest the profits.
Agencies can be great businesses, but they don't have much recurring revenue, and they're only as good as your last project.
I wanted to build something scalable and recurring—something like Basecamp.
We built Flow, a simple to-do app that helped teams collaborate.
It was beautiful.
We launched it, and within 24 hours, thousands of people had signed up.
I was hooked.
We started hiring like crazy—designers, developers, marketers.
We opened fancy new offices and were suddenly spending tens of thousands a month on salaries, equipment, and rent.
I kept reassuring Chris, my then-CFO, now business partner.
He was freaking out watching me burn so much money. Metalab was growing like crazy, but as it grew, we were pouring 80-90% of our free cash flow into Flow and other dumb ideas.
I thought he was shortsighted:
"We are going to make millions! Maybe billions!"
"You have to spend money to make money!"
"Once we launch this new feature, then everyone will see!"
Then I heard a name start popping up. Quietly at first, then a lot.
Asana.
It turned out that Dustin Moskovitz, the billionaire co-founder of Facebook, was a fellow to-do-list junkie, and he was quietly working on his own product.
A few months later it went live.
And I breathed a big sigh of relief.
It was ugly—designed by engineers. Complicated and hard to use.
Not a threat in the slightest.
I felt validated:
With a team a quarter of the size, and a fraction of the money, we had built what I felt was a superior product.
Around this time, Dustin and I had coffee in San Francisco.
He told me that they had raised a huge amount of money and that we'd be stronger together. Perhaps we should join forces instead?
He was super nice, but I wasn't into the idea. After all, we were Apple and they were Microsoft. And we were allergic to venture capital—we were bootstrappers, baby!
(Emphasis on nice. He is a very down-to-earth and humble dude. Ironically, both Dustin and Christian Reber from Wunderlist, my two key competitors who I wanted to hate, turned out to be really good guys.)
He walked me through their investors, war chest, and hires—all formidable—and gently proposed we join forces.
I dismissed this idea immediately.
After all, I was on the bootstrapping train and he was foolishly slurping up Silicon Valley Kool-Aid!
"Nice try!" I thought. "Let the games begin…"
We left with a friendly handshake.
Flow kept growing quickly, but our customers were demanding.
They wanted an iPhone app. They wanted an Android app. They wanted an iPad app. They wanted a Mac app.
Asana quickly released apps on all platforms.
After all, they had a dev team five times our size.
Suddenly it was a key feature when people compared Asana and Flow side-by-side.
Mobile was table stakes.
We had to keep up.
Almost overnight, our burn doubled.
I continued to pound cash into the business.
Our burn kept growing. $20k → $40k → $60k → $80k → $150k/month.
For designers, more developers, more marketers, more office space.
More everything.
Until my bank balance couldn't keep up.
At one point in 2012, Chris even had to inject cash from his personal account so we wouldn't miss payroll.
It was terrifying.
I started to realize how big a bet this was. We were feeding a bonfire with dollar bills.
I had almost zero other investments outside of Metalab, which was going through a slow period at the time.
By this point, I had invested millions of dollars, without even realizing it.
Just continual weekly injections over the course of years.
Death by a thousand paper cuts.
Then, Asana raised even more money and started pouring it into marketing.
Of course, we didn't believe in paid marketing—it seemed douchey and aggressive.
We focused on organic growth…
Until that point, we had just done Field of Dreams marketing:
"If you build it, they will come."
Well, nobody came. We were a fart in the wind.
Suddenly, Asana ads were everywhere.
Billboards. Bus stops. Conferences. Airports. Google. Facebook. Capterra.
Even our own Google keywords were plastered with "Asana vs. Flow" paid links.
We started burning money on ads and hiring salespeople just to keep a toehold, but mostly we focused on making the product better than theirs—our one remaining advantage.
But our product was suffering.
In order to stay competitive, we had underinvested in our engineering team due to cash constraints and stretched them across mobile, desktop, and web.
We started to get an endless stream of bug reports from our customers.
Our growth slowed. Then stalled.
20% monthly growth dropped to 5%.
Customers weren't getting the features they wanted.
The support inbox was filled with the same five words: "It's not syncing again."
Our team felt frustrated and under-resourced and we churned through staff.
We had to hit pause and spend years—literally years—rewriting all of our apps, only to emerge on the other side to see…
Asana had hired designers.
At first, a tiny little team. Nothing to worry about.
But after a year or two, they started hiring a huge team of incredible people.
One day I woke up to see that Asana had fully relaunched.
Their marketing site looked… great.
Better than ours.
Their new app, while not perfect, had all the features we wished we had time to make, worked on more platforms, and most importantly was fast and not buggy.
By this point, we were burning over $150,000 per month.
Chris was tearing his hair out and pointed out that we had burnt through something like $5 million with no end in sight.
Still, we powered on for years. We even doubled down and raised money—too little, too late—from some friends of mine.
We decided that we didn't need to "own the market."
We could just have a small slice of pie. We focused on base hits.
For a while, that looked like an okay strategy. Our meager slice of pie.
Our revenue growth slowed, but we kept on growing.
Until one day it didn't.
Churn caught up with us, customer acquisition cost became unprofitable (Asana and others could afford to spend way more due to higher lifetime value), bugs continued to dominate our time, and Asana and others kept making their product better.
By 2022, the comparison was brutal: they were simply better.
They won. We lost.
Twelve years and over $10 million lit on fire. We waved the white flag.
Done burning money in a losing battle.
The writing was on the wall. Dustin was right.
We lost the war, due to my own inexperience, product myopia, and a lack of capital in a highly capital-intensive and competitive space.
We were forced to downsize to breakeven and shift to a team based in India to keep the remaining customers happy, and Flow became a shadow of its former self.
For the past three years, it's been on life support.
But this last week, we let it go gently into the good night.
I signed the documents to dissolve the company and exhaled a sigh of relief.
My most epic business disaster was finally over. With many expensive scars to show for it.
In retrospect, we were like Fiji waging war on the United States with a collection of AK-47s and speedboats vs. artillery and aircraft carriers.
We got obliterated. Obviously.
Looking back as a grizzled entrepreneur and investor, it was inevitable.
VCs, friends—hell, my own business partner—all walked me through this, but it took years to sink in.
It was a slow-motion train wreck.
A thousand paper cuts, driven by my complete inexperience and incompetence.
While I think that failure is the best teacher, I think it's even better to learn by reading about my failures in a newsletter instead of losing $10 million yourself.
In this instance, I learned a lot:
Goodnight, sweet prince 🥲
I'm hosting a very odd conference in Maui.
One for lonely weirdos like me who run holding companies with many (sometimes dozens of) businesses.
I looked it up, and the term for people like us is "Conglomerateur." If you ever want to get punched in the face, introduce yourself as one!
We have some incredible speakers and attendees (Ben Gilbert from Acquired, and Tren Griffin from Microsoft, to name a few) and it's shaping up to be a great event.
If you run a holding company doing $25M+ across a variety of businesses, you should apply.
If Apple made an electric razor, it would look like this.
I just got a Laifen P3 Pro and I'm absolutely blown away by the design and build quality. China is really upping its game.
I got one of these little e-ink displays for our kitchen and I love it.
It's called TRMNL and I have it show countdowns to birthdays, holidays, and vacations, plus our family calendar. It's really well crafted and totally extensible. If you can code (or use ChatGPT) you can basically have it display anything you can dream up). The battery lasts forever and it's super thin and light. Very cool product.
On the one in my kitchen, I just added a countdown clock of how many days ChatGPT estimates I have before I die (17,451 days). Fun customization!
I'm obsessed with this paired down version of 'Strawberry Fields Forever' from The Beatles Anthology. So good (Spotify).
That's all for now…
-Andrew
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