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.
Four years ago this week, I left The New Yorker to launch Inbox Collective. I kept things simple at the start.
I launched Not a Newsletter as a Google Doc so I wouldn’t have to build a website. It was enough to start.
I set up my email list with TinyLetter, not something more sophisticated, so I could launch faster. It was enough to start.
I set up my company’s website as a set of Google Slides, again so I could get something live as quickly as I could. It was enough to start.
I didn’t spend money on a logo or business cards. I realized: Why would I need those on Day 1? I just needed enough to start.
Four years later, a lot has changed. I’ve switched email platforms (twice, actually), built a real website, and brought on freelancers and contractors to help with some Inbox Collective work. I still don’t have a logo or business cards, though — maybe one day, but that day isn’t today.
The question for you is, and always should be: What do you need when you start? Figure out the stuff that’s worth spending time and money on right away. The rest can come later — or, as the work progresses, you may find you might never need it at all.
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Above, the original Inbox Collective “website” was just a public set of Google Slides.
This year, I started writing a quarterly review of my business.
Every quarter, I take 20-30 minutes to go into a Google Doc and jot down a few thoughts on the quarter’s work. What worked well? What am I excited about? What needs work? What’s on the horizon? I write it all down.
The more of these I write, the more I can track my progress over time. I’ve got my spreadsheets to show me the hard numbers — but the quarterly review is a way for me to track how I’m feeling about the business.
It doesn’t take much time, but as I progress, I’ll be able to better understand the trajectory of Inbox Collective — what I did and why I did it. It’s another tool to help me hold myself accountable and to build a better business.
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The data is great, but it helps to be able to track the bigger story alongside it. To that point: At top is a photo of a chart, taken by Isaac Smith for Unsplash.
At the start of the year, I made two small bets with Inbox Collective.
The first was on Dine & Deliver, this dinner series I’m co-hosting with the team at Who Sponsors Stuff. The bet here was simple: Could we start to bring small communities together, in person, in cities all around the world, to talk about newsletters?
Neither of these are short-term investments. I think Dine & Deliver has the potential to grow into a much bigger series of events in 2024 and beyond; I’ve already seen the web traffic to inboxcollective.com double in 2023, and I think we can double again by the end of the year. There’s so much room for growth here — and like with Dine & Deliver, growth should unlock opportunities for revenue: Sponsorship, affiliate revenue, and consulting work.
I don’t expect an immediate return on either of these bets. My goal for 2023 was to break even on both, and I will.
In 2024, I might be able to bet even bigger on the future of the business.
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That’s a photo of me leading the discussion at a Dine & Deliver dinner in Washington, D.C., earlier this year.
When I first started Inbox Collective, I thought most of my job would involve projects and travel.
I’d do an audit for a newsroom, then travel to their office to lead a workshop. I’d take the lead on a big project, where I’d get into a client’s email platform to build something for them. I’d do talks in person. I’d speak at conferences in front of big rooms.
And the job changed when the pandemic hit. I wasn’t traveling for work anymore, which meant more calls and presentations on Zoom. A lot of friends told me they hated Zoom — I found that I loved it. I could actually work with more teams and help a lot more people since I wasn’t spending all my time on planes. I could work with newsrooms and writers in far-off parts of the world, and do so on my schedule.
And at the same time, I started to realize that I didn’t love project work. It took up a lot of time and was full of frustration — exactly the stuff that made me want to go solo in the first place.
So the job changed. I shifted towards the work I liked most: Coaching, writing, and IRL work that involves lots of 1-to-1 time. I took on some audits, but only occasionally. I farmed out work that I wasn’t enthusiastic about to other consultants or agencies.
This week, I traveled to LA for work for an on-site with a client and a Dine & Deliver dinner. I was in LA for 36 hours. I landed just before 2 a.m. in California. I got home the next day after midnight.
And I loved the work I did on site, but it was a reminder of how happy I am with the job I’ve created for myself. It’s definitely not the job I thought I’d have four years ago.
It’s better.
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That’s me on the flight back from LA. I might not have been smiling if I’d realized that I’d get home at 12:30 a.m.
One of the great lessons from BuzzFeed was to launch stuff quickly. Put it out there in the world, try to build an audience, and then decide what to do next. The simpler and faster, the better!
Over the past three years, what’s happened is that the business has grown and grown. And it’s become obvious to me that I didn’t just need a better website to explain how I consult with brands. I needed a place to share more stories to further serve the email community.
So here we are: Inbox Collective is officially a real website. We’ll be publishing a few times per month, with case studies, how-tos, feature stories, and more. You can check it all out here.
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.
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At top is a slide from an audit presentation to an Inbox Collective client.
When I was getting started with Inbox Collective, I made a conscious decision: I wanted to help as many people as I could, which meant I needed to share a lot.
Not a Newsletter remained free — even as others built large, paying-subscriber-only lists — because I knew that keeping it free and open would allow me to help newsrooms, non-profits, and individuals who couldn’t afford to pay.
I launched new resources for readers to download and use, like my list of growth ideas, because I knew it would help them take the next steps with their newsletters.
I gave away time every month for 1-on-1 calls, so I could dig in with my readers and really help them figure out specific challenges.
And I’ll admit: I was worried at times about this! Was I giving away too much? Would people think, “Well, I guess he’s shared everything he knows! No need to listen to this guy anymore!”
But the results are clear: By giving away a lot, it’s brought even more people into the Not a Newsletter audience: New readers, and, yes, many new clients. By sharing tools, resources, and strategies, it’s attracted a larger audience for me to help — whether they’re working with Inbox Collective or not. (And many clients tell me: We’ve learned so much from you already, so we’re excited to hire you and learn even more!)
The ultimate metric of success, for me, isn’t revenue — it’s impact. So I’ll keep sharing, as often as I can, as much as I can. I know there’s more I can do to help.
So here’s a story: It’s September 2019, and I’m flying to New Orleans for the annual Online News Association conference. It’s my first one representing my own business. I’m not Dan from BuzzFeed or Dan from The New Yorker anymore.
I want to do something to make as many connections as I can while I’m there. All year, I’ve been doing stuff that doesn’t scale — guest posting on other blogs, doing podcast interviews, sharing my content 1-to-1 with friends in the industry. My newsletter’s growing, but I know there’s more room for growth.
So I announce that Not a Newsletter is throwing a happy hour. (Naturally, I call it Not a Happy Hour.) I invite anyone to come out — drinks are on me. I hand my credit card to the bartender and hope the bill won’t be too extravagant.
50 people showed up that day. A bunch of readers brought friends, which meant that I got a few newsletter subscribers out of it — but I also landed three new clients from that night, and got asked to give a keynote talk at a conference. (The total bar bill: About $400.)
When you’re growing an audience and building a brand, do things that don’t scale. That’s where your initial growth is going to come from.
And remember to tip your bartenders well in the process, too.
Inbox Collective is my second attempt at starting a business — a decade ago, Stry.us was my first. I know more this time around, I’ve better organized a network of supporters around me, and this time, I’ve built an audience to support my work. I learned so much from Stry.us, and it’s put me in a far better place to succeed with Inbox Collective.
But even with all that knowledge, I’ve found that there are still obstacles in my way. I believe that these four obstacles exist for everyone who starts something — no matter how ambitious the project or how prepared the team is behind it:
Time — There’s never enough time to do all the things you want to do. In a business like mine, it’s so hard to strike the right balance between doing the work that pays the bills and building the relationships that will lead to paying work down the road. If there were twice the number of hours in the day, I still don’t think it’d be enough. It means that I need to prioritize certain work and say yes to only the things that are most important to me — even though sometimes, I have to say no to stuff I’d really love to be able to do.
Money — This was the big question when I launched: Would anyone actually pay me to do this? The answer’s been a resounding yes, and I feel so grateful for that. But now there’s pressure to keep this thing going. 2020 changed everything — no work-related travel or talks, but lots of remote projects. Could I keep that up for another year or three if I had to? So many of my 2020 projects came from meeting people at conferences and events back in 2019, and if my business stays remote for the foreseeable future, I wonder if I’ll be able to keep this going. I know I can do it, but that fear is still going to be a small weight on my shoulders. Even when things are going well, I’m always going to be looking ahead and trying to plan for what’s next.
Stress — Anytime time and money get involved, there’s going to be a certain amount of stress, too. Inbox Collective is my work, and mine alone. If it succeeds, if it fails, it’s on me. I like the pressure of it, and I’d gladly take this work — even when it’s stressful — over the frustrations of working within a larger organization. (And that might change down the road — that’s just how I feel today!) But it doesn’t change the fact that this job applies real pressure on my life, and it’s up to me to manage that stress. It’s something I’ll always have to deal with.
Failure — At the end of the day, there’s always the chance that Inbox Collective fails. I might not be able to do the work, I might lose clients, I might have to change careers or fields. Now that things are working, there’s pressure to keep this business going, and to keep learning so I can continue to grow Inbox Collective.
I don’t know what Inbox Collective will look like in a year or five. I certainly have no idea whether it’ll be around in 10 years, or beyond that. But I know that as long as I work on this, those four pressures — time, money, stress, and failure — will weigh on me. That’s just part of the job.
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At top, that’s a photo taken of me giving a talk in 2019.
At the start of the year, I had a revenue goal in mind for Inbox Collective. Revenue isn’t the only metric that matters to me, but it’s certainly an important measuring stick for a consultancy like mine.
This week, I broke my revenue goal for 2020 — with two months to go in the year.
But I’ve still had this odd feeling all week. Work is good, I’m as busy as ever, and thrilled about the clients I’m working with. I just hit a big goal, despite all of the obstacles that 2020’s thrown my way!
And yet, there’s this nagging fear: What if this all goes away? What if the business hits a rough patch?What if my clients leave?
What I’m recognizing is this sense of paranoia that I’ve seen in several founders I look up to. It’s a sense that you can’t get complacent, even when business is good. I know I have to keep learning and keep creating new ways to help my community. I know I need to think about new revenue streams. I know I have to start thinking about big choices for 2021 — where I might expand my work, and ways for me to better serve the clients I have.
I feel like I can see around the corner to what’s coming next, and I’m excited about what lies ahead. But I’m still nervous. None of this is guaranteed, and I know I have to keep working to move this business forward. I still have a lot more to learn.
That stock photo — of a motorcycle going through the mud, which, honestly, doesn’t have anything to do with this post — comes via Gabriel Sanchez and Unsplash.
