I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing teams.
I left The New Yorker a year ago today. Leaving a place as special as that to start a consulting business is a true leap, and I’m lucky to have had so many amazing people supporting me on this journey.
To everyone who offered words of encouragement, advice, introductions; to everyone who shared my Google Doc with their friends; to every client who believed in me and decided to take a chance to work with a one-man newsletter operation:
Thank you.
And, of course, to Sally, for encouraging me to take the leap. I could not have done this without her.
Here’s to an amazing, unexpected, unforgettable first year. And here’s to wherever the road leads next.
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Thanks again toWesley Verhoeve, who took the headshots on my site. They’ve been republished here with his permission.
When I left San Antonio to start Stry.us, I didn’t know what I’d find in Biloxi.
When I went to Springfield and hired a staff, I didn’t know what we’d actually make.
When I took a job at BuzzFeed, I didn’t know the kinds of work we’d do over the following years.
When I started at The New Yorker, I didn’t know the projects that we’d put out into the world.
When I left that role to start Inbox Collective, I didn’t know where I’d be in a year. I didn’t know the work I’d do, the clients I’d be lucky enough to work with, or the connections I’d make.
I had no idea.
And I still don’t know what things will look like one year from now. I have a guess — I think I can see around the corner — but I truly don’t know.
Ask. Learn. Be curious. Wherever the road goes, your curiosity will lead you there.
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That photo’s one I took at Salt Lake City International Airport earlier this year. I remember thinking as I was taking that photo: Who would’ve guessed that my work would have taken me to such beautiful places?
Nine years ago, I attended a baseball game I’ll never forget.
It wasn’t a particularly important game: Nats-Phillies, in the middle of the 2011 season. The Nats finished that season 80-81 — out of the playoffs, again.
It was a humid night in D.C. We sat through a two-hour rain delay before the game really got going, and once it did, the Nats fell behind, 4-0. By the 7th, with a score of 4-2, my friends said they were tired and wanted to go home. I couldn’t blame them — it was late, and the game really didn’t matter.
Still, it was my last baseball game of the season — I’d be heading to Columbia, Mo., for a fellowship in a few days — and I wanted to see it through. I’d been to enough baseball games to know that if your team’s losing by a few runs that late in the game, they usually don’t come back.
But then again: You never know. And I remember from my days covering the team that you can’t finish your game story until the final out.
My friends went home, but I stayed.
In the 9th, the Nats faced Ryan Madson, the Philadelphia closer who’d only blown one save all year. But the Nats came back, stringing together a few hits to tie the game. Then came Ryan Zimermman, the third baseman and the face of the franchise. Two outs, bases loaded, bottom of the 9th, full count — and he hits a walk-off grand slam to left.
I remember texting my friends and telling them to turn on the TV. I remember their disbelief at the score. (“We…won???”) I remember how strange it felt to be truly surprised by a result like that. Up until those last moments, it seemed unlikely — even impossible — that the game could have ended the way it did.
I almost never leave games early anymore. As long as there’s still more to play, there’s more story to be written. You never know when you’ll get the chance to write a better ending.
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That photo is of Nationals Park, and was taken by Sung Shin for Unsplash. The video is of the walk-off grand slam — wait until the very end.
In 2010, while reporting in Biloxi, Mississippi, on the anniversary of Hurricane Katrina, I stumbled upon this story:
A century earlier in Biloxi, there was a man of some renown named Walter Hunt. He didn’t go by that name, though — in town, locals called him Skeet.
Skeet was quite the figure in Biloxi. At age 26, he’d become the youngest alderman in the city’s history. He’d been the grand marshall of the Mardi Gras parade. Later in life, he’d move to Washington, D.C., and become a captain of the Capitol Police. (He’d ship up fresh seafood from the Gulf on trains when he was trying to curry favor with members of Congress.)
But in 1925, Skeet took a gamble. He’d inherited an island, twelve miles out in the Gulf of Mexico, from his grandfather, and decided to build a casino on it. He called it the Isle of Caprice — “caprice,” as in, a sudden, unpredictable series of changes.
For a few years, things went well for Skeet and his casino. Business boomed. In 1927, an estimated 40,000 visitors came to the island. Ethel Merman played the lounge.
Then in 1931, Skeet’s team went out to the island to get the casino ready for the summer season.
But the casino wasn’t there.
What must it have been like to be a member of the crew, floating out in the Gulf of Mexico, and suddenly realizing that Isle of Caprice had been built not on an island, but a sandbar? What were they thinking as they discovered that over the winter, when the sandbar moved, the casino had sunk into the Gulf?
All the staff could find was a single pipe sticking out of the water, still connected to a well that had been dug deep into the ground. Everything else was gone.
I’ve been thinking a lot lately about Skeet’s story. I’m thinking about all the things that will be different once we’ve emerged from this pandemic. Businesses will change, cities will change. We don’t know what life will look like in a few years, but things will almost certainly be different.
Right now, that once-solid ground is shifting underneath our feet. Standing still isn’t an option. It’s up to each of us to recognize that we need to move with the tides — or we will sink.
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At top, that’s a postcard from the 1920s of the island. Below, a photo of Skeet from a Mardi Gras parade.
The truth is, I almost didn’t leave The New Yorker when I did.
I knew that I wanted to start Inbox Collective. I knew there was a market for my services. I knew that I had an opportunity to help the journalism world.
But I wasn’t sure if the timing was right.
Sally was in nursing school. She was 18 months in, with a year of classes left. She’d graduate in Spring 2020. And my thought was simple: Sally still had a few semesters of tuition left to pay, we were a one-income household, and if Inbox Collective didn’t work, we’d be a no-income household. Leaving my job to start a consultancy was a gamble, and the safe move was to wait until Sally had graduated and gotten a job — sometime in the summer of 2020.
But Sally convinced me to take the leap anyway. She reminded me that I had momentum and a clear opportunity. There was something else, too, something we talked about a lot at the time: The window for me do this was open, and we weren’t sure how long it would stay open. There was risk in leaving my job to start something new, but also risk if I waited too long and the window closed.
Now looking back, if I’d waited, I don’t think I’d ever have left to start Inbox Collective. Taking the leap to start a business is tough enough during good times, but during a recession and a pandemic? There’s no way.
It’s a reminder that when you’ve got something you’re excited about, and something you feel ready to take on, the only time to try it is now. If you wait, the window might close, and you might miss out on that opportunity forever.
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That’s a photo of me giving a talk in Sydney last year — one of many pretty amazing experiences that I couldn’t have had without taking the leap.
When I think back on my time at BuzzFeed, there was a lot that made us successful. We hired a talented, diverse group of creators. We invested in learning and development programs so staff could continue to grow in their roles. We built strong product and data teams to provide the resources so we could try things that no other media company could do.
But we also were willing to let a lot of things go.
There’s a long list of BuzzFeed projects that launched — some to significant fanfare — that didn’t work.
There aren’t many who still remember projects like BuzzFeed University (a program to encourage advertisers to build their own sponsored content), Fre.sh (a dashboard tracking the biggest stories on the internet), or Star.me (a social network that allowed you remix content). We launched these, and quickly realized that they weren’t working.
Sometimes, BuzzFeed launched projects that flopped — but showed a few signs of promise. Often, someone on staff would latch onto those projects and try to figure out how to take what had worked and turn it into something new.
But with certain projects, we knew early on that there wasn’t an audience for the thing we’d built. So instead of compounding our error and continuing to funnel resources and staff into a failure, we let it go, and moved on to whatever was next. There was always another idea that was worth trying.
No one wants to see a project fail. But it happens. Anytime you launch something new, make sure you know in advance how you’ll measure success for this new thing — if you do that, you’ll be able to see clearly when a project works, and when it doesn’t.
When it doesn’t, you may have to let it go. If there isn’t an audience or a need for the project, no amount of tinkering or investing is going to help. Better to quickly move on to the next idea than to lose more time trying to fix what doesn’t work.
When I think of Carl, I think of his friendship and partnership with Mel Brooks — in particular, their work on the “2000 Year Old Man.” I remember listening to those records as a kid and being amazed at how funny they were. It was just two comedians having a conversation, but those records always made me laugh. (“How many children do you have?” “I have over 42,000 children. And not one comes to visit me.”)
What amazed me most was how silly they were. I think the “2000 Year Old Man” was the first time I realized that adults were allowed to be silly. Until then, I thought that was something only kids could be. I still tend to gravitate towards people who are silly — silly people have such amazing energy, and bring a sense of joy and wonder to everything they do.
The more I watched from Carl — from “The Dick Van Dyke Show” to “The Jerk” — the more I saw that silliness and playfulness in everything he did. As I’ve thought about him this week, it’s the quality I keep coming back to.
Thanks for the laughs, Carl. And thanks for teaching me to be a little bit silly every day.
By the end of January, I had my calendar for the entire year pretty much set.
I knew where I was going to give talks this year, and had the flights planned out. I knew which weddings I’d be going to. I had some vacation days penciled in.
Then Covid-19 hit here in the U.S., and all of that changed.
I used to have a nice balance of remote work and in-person work. Now, like everyone else, my work’s shifted entirely online. I’m not sure when I’ll fly next or when I’ll travel again for work.
And that’s OK! I’m lucky to be the position that I’m in. Inbox Collective is doing well, and I’ve got my hands full with work. I feel incredibly grateful for the opportunities that I have.
Still, I’m realizing how much I miss being able to look forward to the next thing: The next trip, the next birthday party, the next night out. Zoom is such a useful app, but it’s not the same as being there with friends or clients.
Here’s the closest thing I’ve found to life before Covid-19: This past weekend, my wife and I decided to get out of town for a few days. We rented a car and drove upstate. We didn’t do much — we ate, we drank, and we saw a few friends from a distance — but just knowing that we had something like that on the calendar lifted both of our moods for an entire week.
Going forward, I’m going to try to keep putting something on the calendar to look forward to. It could be small (setting aside some time to meet a friend in the park) or big (a road trip somewhere). I’m not going back to the pace I had a year ago, and that’s alright by me. Just knowing that something’s coming up is enough to keep me moving forward.
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That’s a screenshot of Flighty, the app I use to track my travel. That’s what my travel schedule looked like from March through June. (Obviously, it all changed.)
I’ve been thinking a lot about the platform I have, and how I can use it to help. Then I had an idea for a way to do just that — to help newsrooms and nonprofits send better emails, and to raise a bunch of money for an amazing cause. In the first 24 hours, we raised more than $1,000 for The Marshall Project.
So here’s how you can help and get access to a resource to help you grow your email lists, too.
I’ve created a new guide with 25 great ways to grow your email list. I hope you grab these slides, get your colleagues together on Zoom, and talk through them. I think you’re going to find a few new ideas worth trying.
To get access, all you have to do is first make a donation to The Marshall Project, a non-profit newsroom that covers criminal justice. I can’t imagine a more important moment for this kind of reporting. You’ll be supporting an amazing cause.
If you donate $10 or more, I’ll send you the slides. In July, I’ll donate 100% of all contributions to The Marshall Project. (And if you’d rather donate to them directly, you can do so here. Forward me the confirmation email and I’ll send you the slides.)
