How I Built a Consulting Business From a Google Doc and an Email List

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All of this was an accident.

My company, Inbox Collective, is a one-person consultancy built to serve newsrooms, non-profits, and brands by teaching them how to build an audience, better engage with their readers, and drive revenue. But I never expected to become a consultant or build a business around newsletters. I was just trying to launch a side project — and accidentally created a business instead.

From accidental beginnings have come actual success. Over the past three years, I’ve consulted directly with more than 90 different news companies and creators, and gotten the chance to speak about my expertise on four continents. I wanted to share my story with you — how it started, what’s worked, and what’s next — for one reason: There’s a path here for indie consulting, and I’m hoping my story inspires others, particularly in the news and non-profit world, to consider this line of work.

But if you want to understand how I got here, it helps to understand how all of this began.

The ‘Not a Newsletter’ Origin Story

Let’s take things back to January 2019. After a few years of building the email team at BuzzFeed, I’d gotten a job as the Director of Newsletters at The New Yorker. It was a great job working on a growing team at one of the most influential publications on the planet. I’d joke often with friends that it wasn’t a dream job — simply because I’d never been ambitious enough to dream that I could work at a place like The New Yorker.

Over the previous six years, I’d started to build a profile in the email world. I’d given keynotes in New York, London, and Brisbane, Australia. I’d been quoted in news articles about the email space. And on a monthly basis, I’d get a few emails from people in other newsrooms, asking if they could pick my brain. The questions were usually the same: How should they structure their team? What made for a good newsletter? How should they grow their lists? And what strategies should they try in order to convert readers to paying subscribers, members, or donors?

So after the umpteenth request, I started to think: There should be a place where people in the news world can go to learn about newsletters! I decided to start something myself.

Here’s where that first I-wasn’t-trying-to-build-a-business choice came in: I put together this guide to email marketing strategies, and published it… as a Google Doc. In that first edition, I wrote:

I’ve spent the past six years helping [BuzzFeed and The New Yorker] build stronger relationships with their readers, and along the way, I’ve learned a lot about how to send really great emails. I also end up reading a lot — more than a normal person should, frankly — about how others build, send, and think about email, and I wanted to find a way to share that with you.

I called my Google Doc “Not a Newsletter” for an obvious reason: It wasn’t a newsletter! But I did want to start building an audience, so I also created a TinyLetter account, and encouraged anyone who enjoyed the Doc to sign up to be alerted via email when I published the next edition. In the first 72 hours, more than 400 readers subscribed to that email alert. (A few days later, realizing that I might have accidentally created something successful, I bought the domain notanewsletter.com.)

I chose the wrong tools from the start. Google Docs offers me no data about my readers — to this day, I’m not sure how many people read it on a monthly basis — and, interestingly, the Doc is completely unsearchable in Google itself. TinyLetter didn’t offer even basic integrations or data.

No one starting a business would choose tools like these. But I never thought I was building a business, so I never gave my tools much thought.

In fact, it took me months to realize that I might even be able to make money from my growing email list. Three key things happened along the way:

1.) ‘Not a Newsletter’ readers started reaching out to me to ask for help.

Many readers — particularly those in newsrooms and non-profits — started emailing me back to ask: Is there a consultant or an agency we should be talking to if we want to improve our email strategy? Over and over, I apologized and told them that I wished I knew anyone I could introduce them to.

Later on, my wife politely pointed out that many of these readers had been hoping to work with me — I’d simply been too oblivious to realize it.

2.) The Google Doc opened up new opportunities for public speaking around newsletters.

One of my early readers was Tim Griggs, a consultant who’d been working with the Facebook Journalism Project on a series of accelerators to help local newsrooms. He invited me to speak at one, in Austin, Texas, to a group of U.S. newsrooms. That went well enough that he invited me to speak at more that year, in Berlin, Montreal, Paris, São Paulo, and Sydney. These speaking gigs helped me realize that there was an opportunity to serve a wide audience around email.

3.) ‘Not a Newsletter’ — along with many of these speaking gigs — helped me meet people who worked as consultants, and who I could talk to about building a business like this.

Before this, I was completely unaware of the world of indie consulting. As far as I knew, consulting was something that only companies like McKinsey did. But in early 2019, as I started to identify this as a potential next step in my career, I got the chance to meet (and to ask many, many elementary questions of) people who’d held a job like this, and to figure out if it was something I might be interested in. (Among the many who offered their time and advice: Aaron Berger, David Weiner, Justin Bank, Lissa Cupp, Lynne Brennen, Ray Pearce, Ryan Tuck, Scott Cohen, Tim Griggs, Tom Critchlow, and Yasmin Namini. Inbox Collective doesn’t even make it through three months without your advice and counsel!)

In May 2019, I bought inboxcollective.com and registered in New York as a single-member LLC. In June, I told my bosses at The New Yorker that I was leaving to start a consultancy.

That’s the point where I started making changes to build a real business.

I moved my email list from TinyLetter to Campaign Monitor to get better data and segmentation, along with the ability to build out a welcome series. I launched the first version of the Inbox Collective site — on Google Slides, naturally, to match the Google Doc, and to make sure I didn’t waste any money or time building out a website that I didn’t yet need. (At that moment, all I truly needed was my email list.) I did an interview with Keywee, now renamed Anyword, to publicly announce my new business. And I emailed my readers — the list had grown to 1,976 subscribers — to tell them that I was leaving my job to start this consultancy.

I knew I needed to generate as many potential leads as I could. So in that announcement email to the “Not a Newsletter” list, I wrote:

These next few weeks, I want to talk to as many of you as I can, learn more about what you’re working on — and find ways to help. So here’s my request: Hit reply to this email, or send me a note at dan@inboxcollective.com, and tell me:

• What are you struggling with when it comes to newsletters?
• If you could wave a magic wand and fix something with your email program, what would it be?

Send me an email and tell me — maybe it’s something small I can help you with over email, or maybe we can set up 20 minutes to talk it through over the phone.

Over the next eight weeks, while I was winding down my work at The New Yorker, I held more than 75 calls with readers. Thanks to some restructuring at Condé Nast, several floors had empty offices. I took over one, running up and down the stairs between my real job and my soon-to-be-real job when I needed to take calls during work hours. In July and August, I spent the usual 40+ hours on my paying job, and another 40 hours a week on Inbox Collective. It was exhausting — but more than a dozen of those calls led to client work.

That’s the story of how a Google Doc accidentally launched this consultancy. Three years later, here’s what I can answer for you about actually building the business.

What Kind of Newsletter Business Is This?

I’m hesitant to use the phrasing for myself — I’m still learning new things every month about email! — but what I’ve built falls into the Expert category of newsletter. I’ve built expertise on a specific topic — in this case, email newsletters — and built an audience that looks to learn from me.

How Big Is Your Audience? And How Does ‘Not a Newsletter’ Grow?

I launched Inbox Collective when I had fewer than 2,000 readers. But an advantage of an Expert newsletter is that you don’t need a massive audience to build a business — you just need a loyal audience where you have a clear opportunity to help.

My newsletter now has more than 8,500 readers, with unique open rates of about 50 percent per month. (Interestingly, that number has remained virtually unchanged over the past two years.)

When I first launched “Not a Newsletter,” readers discovered it via one of my social channels, particularly LinkedIn, or through several Facebook groups devoted to newsletter tactics. Over time, those readers started to share it with their colleagues and friends in the industry. These days, word of mouth is easily the single biggest source of new signups. The others: Talks or webinars that I lead, and interviews that I do for articles or podcasts. As Inbox Collective grows as a site, I expect sign-ups on articles we publish will eventually become the leading source of growth.

How Does Inbox Collective Make Money?

More than 80 percent of revenue comes via consulting — easily the biggest and more profitable part of my business. There are four different types of consulting that I do:

• Retainer work (38% of the business’s lifetime revenue) — These are clients, often large or high-growth organizations, who pay for a certain number of hours up front. We put a weekly call on the calendar, and identify certain projects that I can take the lead on. These engagements typically last at least three months, and in exchange for their long-term commitment, I offer them a discounted hourly rate.
• Coaching (20%) — These are weekly or monthly calls that I do with smaller organizations, often local newsrooms or digital startups. These clients get time with me to brainstorm ideas and talk through specific challenges or next steps.
• Project work (13%) — These are one-off projects, like helping a client build out a welcome series for their newsletter. I charge based on a day rate, which varies based on the type of client and the value of the work to the client. As I’ve grown the business, I’ve discovered that this is my least-favorite type of consulting work, so I’ve stopped offering it to all but a handful of longtime clients.
• Audits + workshops (12%) — Some organizations, typically newsrooms, ask me to audit their email program and put together a roadmap for their email strategy. These audits are often complemented by hands-on workshop sessions to help these teams understand their unique challenges and next steps.

Where Does the Rest of the Revenue Come From?

• 7 percent comes from paid talks, though that number dropped significantly during the pandemic, as I focused on doing free webinars and events to try to help newsrooms and non-profits figure out how to navigate such uncertain times. 
• 5 percent comes from affiliate relationships or commissions from partners. When I recommend certain products to my readers, I receive a commission from those brands after a sale is made.
• 3 percent comes from advertisers in “Not a Newsletter” and on the Inbox Collective site.
• 2 percent comes via teaching, through programs hosted by places like the City University of New York. 

What Does Inbox Collective Spend Money On?

The short answer: Not much.

My single biggest expense is my monthly contract with Mailchimp, which sends my newsletter. (I switched over from Campaign Monitor earlier this year.) I spend about $1,300 per year to send emails through them.

Other key expenses, which add up to less than $1,000 per year: 

• Zoom, so I can connect with clients and readers.
• G Suite, for my inbox and calendar.
• Vimcal, to help schedule my meetings.
• Bluehost, to run the Inbox Collective website.
• Fathom Analytics, to deliver basic analytics for this website.
• Quickbooks, to organize my expenses.

I’m also testing out a few different audience growth tools on the website: WPForms, for some of the sign-up boxes you see in the footer and on my main sign-up page, and RightMessage, which handles the pop-ups. WPForms costs $100 for the year, and RightMessage costs $79 per month. In the long run, I expect this to be another $1,000 per year in expenses, but one that I’ll happily pay. As my email list grows, so does my business.

I’ve never rented office space — I use part of a bedroom in my apartment for work. There are the expenses that any business has: Internet, as well as a cell phone plan. In 2020, I spent a few hundred dollars to upgrade my computer monitor and webcam. I do anticipate that in the next year, I will spend some money out of pocket to attend conferences or events (though if I’m speaking at one of these events, the cost of a ticket is often comped).

But the best money I spend? It’s on my accountant. Running a business like this — even a one-person operation with relatively few expenses — is still complicated, and it’s worth the expense to find someone who can help you with the filings and paperwork that come with the business.

I’m also very, very lucky: The Oshinsky family is full of lawyers. When I need help drawing up a contract or asking for legal advice, I don’t need to hire someone at a high hourly rate — I can call my dad. Having access to free legal help has saved me thousands of dollars as I’ve grown the business.

Will You Ever Hire Someone to Work With You at Inbox Collective?

In a year, my answer might be different. But for now, I like being a one-person operation. It gives me the freedom to say yes to only the projects I’m most excited about, and it gives me the flexibility to take time off when I want.

One thing I am trying this summer is bringing on subcontractors for occasional work, which allows me to take on larger projects that I might not be able to do alone. The challenge there is finding people with both the skill and flexibility to take on additional work.

I am looking to bring on freelance help to write about the email space, both in “Not a Newsletter” and on inboxcollective.com. (If you might be interested in writing about newsletters, email me at dan@inboxcollective.com — let’s talk!) I’m happy to reinvest some of my revenue on reporting, interviews, case studies, and essays that might help my readers. I think creating more content about email will allow me to have a bigger impact on this space, and help me grow my audience in the long run. (And building out the site opens up new opportunities for advertising or affiliate content.)

One more thing: Hiring freelancers does have some upside for Inbox Collective, too. It should free me up to spend more time working with clients, not writing. I think there are better reporters and writers out there than me — why not focus on the things I do best?

Why Isn’t ‘Not a Newsletter’ a Subscription Business?

I’ve thought about it — particularly back in 2019. Had I decided to focus just on reaching larger newsrooms, it might have made sense. (I would have likely charged north of $750 per year for access, and focused on building out a very different type of product than the current Google Doc.)

But I think my current model suits me far better. For one, it allows me to reach the widest possible audience, including creators and small newsrooms who can’t afford a subscription. “Not a Newsletter” now reaches readers in more than 70 countries, and putting content behind a wall means that I’d probably only be speaking to those in wealthy nations, like the U.S.

Keeping the Google Doc open to all also means that I can pivot to cover new topics. Two years ago, the creator economy wasn’t something I was focused on. In the year ahead, I’m hoping to produce dozens of stories designed specifically to serve that audience.

Consulting tends to be a really good match for the way I work. I love to learn new things, and with every new client, I get asked to learn new skills to solve problems for them. I know more about the email space now than I did when I started this business — and I absolutely love discovering new ways to help my clients.

There’s one more thing: I like having a business with a diverse set of revenue streams, and I want to build a business that can survive in good times and bad. Since 2020, the business has continued to grow, despite the massive changes that the pandemic threw at all of us. If this business can survive — and grow — during tough economic times, I’m confident that I can build something that can last.

How Will the Business Grow in the Next 24 Months?

I’m particularly bullish about my affiliate business. There are so many different tools out there to help those who send newsletters, and it can be incredibly complicated to understand which tools work for certain types of businesses. As “Not a Newsletter” and Inbox Collective grow, I see opportunities to direct readers towards the products and tools that can help them succeed with newsletters. Many of these tools have become affiliate partners of mine — when I refer a new customer to those businesses, I receive a commission.

(Of note: Over the years, I’ve turned down more affiliate opportunities than I’ve accepted. I only have affiliate relationships with businesses that my clients or I personally use and recommend.)

I’ve also started to set up affiliate relationships with other email agencies. There are times when a potential client needs consulting, technical, or design help that I can’t provide, and I’m happy to introduce them to someone who can do the job well. My stance is simple: If both parties win, I’m happy to accept a small fee for serving as a matchmaker.

I’m also excited about hosting workshops for newsrooms. The first of these will take place in Copenhagen in September — we’ll have about 20 attendees from several different orgs come together to learn about how to build, grow, and monetize their email lists. If this first workshop goes well, I’m hoping to do more of these in 2023.

Could Anyone Build Their Own Inbox Collective-like Business?

To me, the biggest surprise of this journey is that more people aren’t trying to build a business just like this. As I look at the news world, I see opportunities for similar businesses that serve newsrooms around SEO, social, copywriting, or data analysis. As a lean, one-person operation, this model absolutely works — if you build an audience and expertise first. 

And this can’t be underestimated: From a financial perspective, I was in a good position at the start of this process. My wife has a great job as a nurse, with health insurance that covers both of us. We had savings in the bank when I started Inbox Collective, which gave me a runway to get started. All of this has been a massive tailwind behind me, making it easier for me to move forward with this business.

That doesn’t mean that building this business has been easy. This job — especially in these first few years — has required long hours and hard work. My earnings are directly tied to how much work I do, a potential recipe for burnout that many self-employed people encounter. But I’m lucky to have met others in this space who’ve been able to offer counsel and help as I’ve grown this business. I’m lucky to have an amazing wife who’s supported me from the start. And I’m lucky that I truly love the work. This is the most rewarding work I’ve ever done, and also the most stressful. It’s not for everyone.

Still, I love the work, and I love the opportunity to serve my readers. I’m hoping that by being transparent about Inbox Collective, I might help others consider launching Expert-like newsletters to serve readers about the topics they know best.

Your community might be out there, too. I hope you’ll consider building a newsletter for them.

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