Hitting $1 Million ARR

Last year, I posted about growing Optimist from 0 to $500k ARR in our first year.

It was super popular and got a lot of folks who were interested. So, figured I'd come back and share another major update from year 2 of business.

After launching Optimist in December of 2016, we have grown the company to an MRR of about $85k.

That puts us on track to do $1MM run rate in 2019.

Trajectory:

Just a quick recap on Optimist and our business model:

• We're a full-service content marketing agency
• Most of our clients hire us to help scale organic traffic and generate MQLs from content
• Clients are primarily startups, usually VC-funded $10mm+
• Our engagements generally run $6-10k/mo, which is an all-in cost
• We bring a team of 5+ to run everything from strategy and research to content creation, promotion, linkbuilding, etc. Everything is white-hat, above-board content marketing according to current best practice
• Target margins ~40%
• Our model is hybrid between a traditional agency and an outsourcing operation. We have a team of ~17 freelancers and work as a "collective". No full-time employees, 100% remote/distributed
• We pay a competitive hourly freelance rate + offer profit share model for freelancers

As of today, we have about 14 total clients on monthly retainer.

This last year has been one of growth and reflection. As a company, we have evolved our model into something that looks and feels more like a real business. We’ve reinforced our team, created a more fluid structure, and focused on improving operations and communication.

It’s also been a year of growth for me.

This company grew out of my own personal freelancing business. It was an extension of me—and I felt a lot of need to control and own so many of the moving pieces.

I’ve learned to step back.

In focusing now on shaping my own role—thinking about what part I truly want to play in the future of Optimist, what parts of my job can scale, and what parts I’ll need to hire out or delegate.

Our next goal is to get to $1.5MM ARR.

That should roughly cap us out in terms of our current capacity to manage clients (have 2 principals now, capable of managing 6-10 clients each).

When we get there, I’ll likely put the brakes on the company and stop accepting new work without churning any of our existing clients. I want to focus on slow and controlled growth—I want the business to feel strong. I want the work to be less hectic and stressful. No kinks in the process.

Over the last year, I have found myself really trying to return to my initial state as an entrepreneur. I want to unpack my ultimate goals/motivations and try to figure out how to build that thing that will ultimately make me the most happy.

My main question has been: How do I want to spend my time? What kind of company do I want to have?

Obviously. I could focus entirely on revenue and growth. I could grind it out -- and maybe we would have grown larger/faster if I did. But, at the end of the day, I realize that my passion is the strategy and the operations of the thing. I like to have time to incubate and come up with ideas. I don't like the treadmill of growth-at-all-costs and I think it reflects in the level of work that we deliver.

More importantly, I know what makes me happy. And it's not the "hustle" of the thing.

Yes, growth and sales are exciting. But, I'm a natural introvert. I'm a numbers and words guy. I like spreadsheets, data, and reading.

So, I want my time to be spent on these tasks. And part of that probably means sacrificing some potential growth to shape the role that I want and to build a company that I want to run.

Anyway -- I'm going to cut my rant here. I'm happy to answer questions. We operate with basically 100% transparency; so very few (if any) topics are off-limits here.