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.
When I talk with a prospective new client, they almost always tell me: We want to grow as much as possible, as quickly as possible.
And that’s natural — but my follow-up question is usually: Why?
If you’ve got the team in place, and the strategy in place, I understand the need to grow, and grow quickly — you’re trying to reach a level of scale where your business can flourish.
But so many of the teams I talk to aren’t there yet. They don’t have the team yet. They don’t have the strategy yet.
And in those cases, growth shouldn’t be the top priority. Their priority should be growing their audience to the point where they can prove out their editorial concept and business model. Only once they’ve done that should they shift into growth mode.
Yes, growth always sounds great. But maybe it’s worth asking yourself: What are we in such a rush for?
I’ve been working with a few newsletter writers who are in a period of transition. For nearly two years, they’d been writing multiple newsletters per week. Now, they’re all trying to figure out what to do next. Should they write more, or less? Should they change the way they monetize?
And my advice, over and over, has been simple: Whatever you do choose to do next, make it work for you.
There isn’t a single way forward here. There is no one-size-fits-all answer.
Which means that the right answer, for now, is the one that works for each of these writers. It’s up to them to figure out what they want to build and how they want to build it. There’s no need to build around someone else’s constraints or rules — they’re free to do what’s best for them.
Maybe that means, as I told one writer, telling their readers that they’d be taking a month off in December so they can get ahead for 2023 and pre-write the first few months of newsletters. “I’m allowed to do that?” they asked me.
You are, I told them, because this is all about making it work for you.
Maybe it means changing up the way they monetize. One writer’s been trying to push forward with a paid subscription, but it isn’t working as well as they hoped. But they do have a fairly large, engaged audience. Advertising might be a better way forward for them.
“Can I just cancel the paid offering and switch businesses models?” they asked me.
You can, I said, because if you’re going to make this work, it first needs to work for you.
What’s the best route forward? Figure out what’s best for you , and work from there.
A client had a question recently about something I’d worked on at BuzzFeed, so I went back into my email archives to try to find an answer. And what I found, unexpectedly, was this email:
It’s from the end of year 1 of my work at BuzzFeed. It said:
Monday marks 1 year since we really launched the newsletter program here at BuzzFeed. Quick numbers for you:
January 2013 5 newsletters — all automated, with about 20,000 total subscribers Newsletters drove 46,000 clicks to BuzzFeed Newsletters were the 28th biggest referrer of traffic to the site
January 2014 14 newsletters — all hand-curated, with more than 125,000 total subscribers Newsletters drove over 650,000 clicks to BuzzFeed Newsletters are the 8th biggest referrer of traffic to the site
I’ll be honest: I knew I did a lot of work that year — I just didn’t remember how much work!
Looking back, I know I was motivated to prove that newsletters could be a great tool for BuzzFeed, and I remember working long hours to keep the newsletter strategy moving forward. I was making stuff up as I went along, and I didn’t really have many resources at my disposal. I was lucky to have a few wonderful supporters in my corner who helped me stay on track. But even now, looking back at this email — which I wrote — I’m stunned at those results from year 1.
Did I really do that?
I know I can be dismissive of some of the work I’ve done in the past. I know I’m better at this now than I was a decade ago. I don’t always want to talk about the mistakes or lessons I learned along the way.
But I don’t get the chance to build Inbox Collective without that work I put in ten years ago at BuzzFeed. I’m grateful for that work, and I’m proud of it.
Bob Uecker’s a former baseball player, and longtime radio broadcaster for the Milwaukee Brewers. (You might also remember him as the announcer from the movie “Major League.”) Last week, on the final day of the season, with the Brewers eliminated from postseason contention, Uecker spent the final broadcast of the season telling baseball stories.
Bob Uecker today talking about how he started with the Brewers scouting the Northern League. He didn’t know to have a stopwatch. “I’d cup my hands like I had a stopwatch, then ask the guy next to me, ‘What did you have him at?’ They’d say ‘3.4 seconds.’ I’d say ‘Yeah, me too.'”
It reminded me of something Adrienne Miller described in her book, “In the Land of Men,” about her first day at GQ:
“As [GQ editor David] Granger and I spoke, it became apparent that I did have one thing going for me: I was able to talk about past issues of GQ. Later, he said that I got the job because I was the one person he’d interviewed who’d actually even bothered to open the magazine.”
“ ‘Never underestimate how unprepared most people are,’ he would later observe, correctly.”
Don’t forget your stopwatch. Read the magazine in advance. And if you’re not sure what you need for the first day, ask. Otherwise, you might not be prepared to do the work.
So here’s how a response to a welcome email led to one of the best things I’ve done in my three years of running Inbox Collective.
In October 2019, I get an email from Jan Birkemose, who runs the Danish media website Medietrends. He got my welcome email and wrote back, telling me a little about his business. We start trading notes back and forth. He tells me about these courses he’s running, including a two-day class all about email.
A few months later, Jan invites me to speak as part of that course. It goes well. He invites me back for another session later that year.
And then two more in 2021.
In December 2021, I happen to find myself in Denmark after Mette Will invites me to speak at Email Summit DK. (Thanks again, Mette!) On my last night in town, Jan and I meet in person for the first time. He asks if I’d be interested in hosting an email workshop of my own in Denmark in 2022.
Yes, I most certainly would.
I’d been wanting to do one of these for a while. I’d built up a series of workshop session that I do with individual newsrooms, but I’d never done them with several different orgs in a single room. Only thing had stopped me: Planning the event itself. Booking a space, coordinating with all the different teams, scheduling lunches for a big group — that part seemed intimidating to me.
But Jan had done these sorts of workshops dozens of times already. If I was going to take the leap on something like this, I needed a partner like him.
Fast forward to mid-September. It’s the end of a beautiful fall week in Copenhagen, and we’ve got 20 participants from 16 organizations (who came from four different countries) in the room together. They’ve learned a lot of the past three days (and, thanks to Jan’s planning, been fed every day!), and are telling me about what they’re going to do next.
They’ve got ideas: For surveys to run, and growth tactics they want to implement, and newsletters they want to launch. There’s a lot of excitement in the room, and a lot more work to do, but this group is ready to take it on.
Now that it’s all over, I’m feeling grateful for the opportunity to share what I’ve learned, and grateful for partners like Jan, who believed in this workshop idea and gave me the chance to lead it.
(And thanks for writing back to that welcome email, Jan! It’s amazing to think about the doors that a single email reply can open.)
———
That’s me with the group at the end of the workshop. What a week!
So we’re at the US Open last week. We’ve seen some great tennis already, but there’s one star we really want to see: Serena Williams. She’s playing in the night match at Arthur Ashe Stadium, the venue’s biggest court, but we don’t have tickets for the night session. So we do the next best thing: We find out when she’s practicing, and wait on the practice courts for her to arrive.
While we’re waiting, we’re hearing the roars from Ashe, where Coco Gauff, the 12 seed, is playing her second round match. She wins the first set, but trails 5-3 in the second set. The match seems destined for a third set. But then Gauff turns things around. She wins her serve, then breaks her opponent. The match goes to a tiebreak. We hear the roars as Gauff wins the tiebreak, the set, and the match.
And a few minutes later, we hear another round of applause from one end of the practice courts. We look up. It’s not Serena — it’s Gauff, walking out from Ashe directly onto the courts. “Her serve was off today,“ whispers someone behind us. I check the stats: Gauff finished the match with more double faults than aces. Not great.
So there she is, on Practice Court #5, mere minutes after winning a big match on center court, and she’s back out with her coach, working on her serve. For a lot of players, making the third round of a major would be a career highlight. But for Gauff, who made the finals of the US Open last year, there are clearly bigger goals in mind.
It reminded me that even the best in their field have an off day. And what do the greats do after an off day? They get right back to work.
Even when you’re at the top of your game, there’s always more work to do.
———
That’s a photo I took of the practice courts, there on the right, at the Billie Jean King National Tennis Center in Queens.
There are a few different ways to become a PGA Tour member, but the most direct is by being one of the top players on the Korn Ferry Tour, which is the top minor league circuit for men’s professional golfers. Just making it to the Korn Ferry Tour itself is hard enough — it requires first going through a series of qualifying tournaments, and then life on the Korn Ferry is a grind. While the PGA Tour offers massive checks, the Korn Ferry’s prize money is relatively paltry. (The player who finished in third place in yesterday’s PGA Tour event won $885,000; the prize money for the entire field at last weekend’s Korn Ferry event was $850,000.) But to get to the PGA Tour, you have to go through the Korn Ferry Tour, so those with dreams of playing on the big tour have to go through the minors first.
And yesterday, the PGA Tour announced the 25 golfers who played well enough during this Korn Ferry Tour to qualify for PGA Tour’s upcoming season. I was reading through their bios and found myself amazed by some of their stories.
Among the qualifiers are Paul Haley II, who qualified for the PGA Tour back in 2012 but played poorly in his one season on Tour. He spent a decade bouncing around the minor leagues of golf, but will be back after a strong season on the Korn Ferry. “Maybe if you were younger, you stress out about really small things and when you play bad, it seems like the world is coming to an end,” he told a PGA Tour reporter. “You’re not going to have your best stuff every week. You’re going to miss the cut. You’re going to shoot over par. But just taking that step back and realizing everything is still pretty good.” This time, he’ll aim to stick around on the top circuit in golf.
There’s Ben Griffin, who quit golf and was working as a mortgage loan officer — until his grandfather died, and Griffin decided to give golf one last shot. (A line in his grandpa’s obit: “His motto was ‘Hit them long and straight,’ having loved golf.”) A year later, Ben qualified for the PGA Tour.
There’s Erik Barnes, who had to take a job stocking shelves at a grocery store during the pandemic (base pay: $17/hour) to make ends meet when the Korn Ferry Tour went on hiatus during the early part of the pandemic. He’s 34 years old, but after more than a decade as a pro golfer, he’ll finally make it to the PGA Tour.
And there’s Kevin Roy, who once missed the cut in five straight events, which meant that he went more than a month without collecting a paycheck. Scrolling through Instagram one day, he saw a hat with the words “Have More Fun” and bought it. While other golfers wore hats with sponsor logos on it, he wore his “Have More Fun” hat as he turned his season around and qualified for the Tour. He’s 32 and will be a PGA Tour rookie.
It’s remarkable the things that people will do to achieve their dreams — the sacrifices they’ll make, the work they’ll put in, the challenges they’ll overcome. Even people at the top of their field struggle. But sometimes, reading stories like these reminds me that it’s possible to reach the top of your field — even if it takes a little bit longer than you expected.
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At the top, that’s a video of the 25 Korn Ferry Tour members who officially qualified for next year’s PGA Tour.
There’s a lot that’s frustrating about being human, but here’s one thing that’s annoyed me a lot lately: You’re not always at your best.
There are days you show up to do the work, and things feel a little off. It doesn’t matter what the work is — it could be a project, or a big piece of writing, or a day on the golf course. Some days, you show up and know you’re not quite right, even if things felt amazing the last time you showed up to do this work.
It’s hard to accept that your body feels a little different today, that your mind’s in a different place, that your energy’s different than usual. Maybe you know why, or maybe you don’t. But you know, because you know yourself:
Today will be less than perfect.
I like being at my best. I like how confident I feel when I know that I’m doing my best work.
But there’s something to be said for getting through those days when you’re at 70%, when it’s not all there. You make the most of what you can with what you have that day. You find a way.
Accept less-than-perfect for today. Better days will come.
———
Naturally, that post was inspired by a morning on the golf course. The day before, I hit the ball so well and felt confident over every shot. The next day, it looked like I’d never hit a golf ball before. It happens.
Newsrooms sometimes hire me to produce an audit of their email strategy. They’ll give me logins to their email system and their analytics, and I’ll interview key staffers to understand what they’re doing and where there are opportunities to improve. Then I’ll turn my findings into a slide deck.
When I first produced these audits, the final deck was about 50 slides long. But as I did more of these, and started to identify other areas to cover during an audit, the decks started getting longer. 50 slides became 100, and then kept growing from there. My most recent audit checked in at 206 slides.
As a partner for these newsrooms, my job is always to overdeliver. I want to make sure I give them everything they’re looking to learn — and then some.
But last year, I noticed that when I’d present these longer decks, I wasn’t getting much feedback from the newsrooms. They weren’t asking questions about specific slides or tactics, which seemed odd, since they’d been so curious earlier in the process. What had changed? After I followed up with a few clients, I got my answer: I was overwhelming them with information.
So that became my new challenge: How could I overdeliver without overwhelming?
A few changes really helped. Up front, I started setting clearer expectations for what a client could expect from the audit. I told my teams: This is going to be a lot, and I don’t expect you to do every single thing in here. That freed up the teams to pick and choose what tasks to execute on based on my findings.
I also changed the structure of my presentations. Instead of one big audit reveal at the end, I started coming to my newsrooms with initial findings — a shorter presentation, about 45 minutes long, to talk through the most important topics, and to get feedback about things they wanted to see more of in the audit. That gave them a chance to start thinking through the big themes of the audit before the final deck was presented.
I changed the structure of the deck itself, adding a section at the start with a list of suggested tasks to prioritize. That helped teams understand which tasks were ones to work on right away, and which were ideas to put on the back burner.
I told newsrooms not to invite their entire team to the final audit presentation. Did the sales team really need to sit through 90 minutes of discussion about email deliverability or growth? No, not really. Instead, I started giving the audit presentation to a core group of stakeholders, and then set up smaller presentations to specific teams (sales, product, editorial) so they could focus on the findings most important to them.
And lastly, I started setting up monthly calls to check in with teams after the audit, to talk through their prioritization list, and to help remove any roadblocks in their way.
I’m still searching for other ways to overdeliver without overwhelming. The audit process isn’t perfect, and there are going to be ways to continue to make it even better.
———
At top is a slide from an audit presentation to an Inbox Collective client.
If you launch lots of new products or features, several aren’t going to work. You’ll be excited about a big new newsletter launch, and you put it out into the world, and the audience just doesn’t like it. It happens!
The truth is: If you’re not failing, it means you’re probably not trying enough new tests.
When you fail, move on quickly. Don’t double down on your mistakes. Keep testing, keep trying. The more you try, the better the chance that you’ll eventually stumble into something that truly works.
