$0 to $4,539,659 (2022 Update)

This is my yearly update post on my content marketing business.

Five years ago I started a content marketing agency called Optimist.

After quitting my full-time job at a venture-funded startup to work as a freelancer, I quickly, “filled my dance card.”

From there, I started a content marketing agency called Optimist to focus on using content to drive growth—primarily for startups and tech companies.

In the last 5 years, we’ve grown the company to about $1.5MM in annual revenue.

It’s been a fun and challenging journey:

• Year 1 - 0 to $500k ARR
• Year 2 - $500k to $1MM ARR
• Year 3 - $1MM ARR to $1.5MM(ish) ARR
• Year 4 - $3,333,686 Revenue

Each year, I’ve shared lessons and progress as we’ve grown, trying to document a transparent look at our victories and our failures. I've gotten tons of feedback, questions, and messages over the years. It's been one of my favorite parts of growing this company.

Coming off of 2020, last year was a much different experience.

Thankfully, 2021 was less stressful and less hectic. But it wasn’t without its own challenges.

Nevertheless, I do feel as though having 5 years under my belt has given me a new level of understanding—and a healthy dose of perspective—that I want to share in this update.

How Optimist Works

First, an overview/recap of the Optimist business model:

• We operate as a “collective” of full-time/professional freelancers
• Everyone aside from me is a contractor
• Entirely remote/distributed team
• Each freelancer earns $65-85/hour (Recently raised and reset our pay rates)
• Clients pay us a flat monthly fee for full-service content marketing (includes research/strategy, writing, design, and content promotion/outreach)
• Packages range in price from $7-20k/mo (Raised our rates; now offering a minimum package at $10k/mo)
• We offer profit share to everyone on our core team as a way to give everyone ownership in the company

Second, a breakdown of Optimist by the numbers, as we stand now:

• $4,539,659 in total revenue as on December 2021
• 15 clients on retainer
• ~$140k MRR
• 27 "core" team members (freelance/contract)
• $68,869 paid in profit share in 2020
• Gross profit margin ~30%
• Net profit ~20%

Here’s our monthly revenue from January 2017 to December of 2021:

Optimist Year 5 (2021): A Year of Maturity and Stability

While 2021 was not a year of huge growth, it was still our highest revenue year to date. We hovered pretty close to our target of $125k/mo and ended the year just under $1.4 million gross. That brings our lifetime earnings to just over $4.5 million.

Most importantly, it was definitely one of our most stable years to date. 2021 felt like a transformational year in terms of finding both stability and maturity as a business.

My wife, Laura, also took on a new role this year—at a venture-funded startup. She’s been a rock—my partner through all of the ups and downs of entrepreneurship. And, now, with us operating in the same universe (startups, broadly), I’m inspired by her ability to find balance—even when the stakes seem high.

As an entrepreneur, I feel like I’ve learned some particularly valuable lessons this year and spent a lot of time trying to shift my thinking, focus on my mental health, become a stronger leader, and also think long-term about my journey as an entrepreneur even beyond Optimist.

With the benefit of 5 years of hindsight, I also feel like I have a much healthier perspective on the company and the trajectory.

When I sat down to write everything I was thinking about in 2021, it turned into a monster post.

So this year, I’ve decided to break it down into a short series. I’ll be sharing 5 parts over the coming weeks:

1. Lower the Stakes
2. Working “On” the Business Rather than “In” The Business
3. Productizing a Bespoke Service
4. Repositioning the Business
5. Returning to My Roots as an Entrepreneur

Hopefully, you enjoy the posts and each one offers a different and detailed look at my experience and the lessons I’ve learned (and been learning) over the last 5 years.

Thanks to everyone for your support.

Anyway—here’s Wonderwall. 😁

Part 1: Lower the Stakes

When you first start, everything feels like an emergency.

Every small hiccup feels like a massive challenge. Every lost dollar feels like your last one. Every piece of criticism stings like a fatal flaw.

I spent the first 4 years of Optimist feeling an almost-constant hum of dread.

There are a million things that could go wrong:

• What if our biggest client leaves?
• What if we lose 3 clients next month?
• What if one of our most important team members quits?
• What if clients don’t pay their invoices?
• What if we can’t deliver the results we expect for this client?

Some days I felt like crying. Some days I felt like hiding. Some days I felt like quitting.

I felt vulnerable.

Other days, I felt invincible. Everything went right and these fears evaporated from my mind as I was confident that we were on the right path and things could only get better.

Then I’d remember those fears and it would bring me right back down to reality.

This, my friends, is the reality of entrepreneurship. It’s a rollercoaster.

That may be a cliché, but it’s true—and it’s important to keep in mind when you’re going through the worst of it. Others have felt this same way; they are feeling this same way. And it’s normal.

All of the things I fear will happen probably will happen.

Most of them have happened to Optimist at one point in our 5 years.

But guess what?

We’ve gotten through it. We’ve survived.

As an entrepreneur, there is almost always a fire burning somewhere or a fire that’s about to start.

If you allow yourself to be overrun by the anxiety and the stress of trying to put out every single fire, you’ll burn out. (No pun intended.)

You’ll crumble under the pressure.

To whatever extent you can, you want to anticipate and prevent problems. But, just as important, is your ability to put those potential problems into perspective. Focus on doing the work that needs done right now rather than jumping at the latest minor disaster. Then, come back and solve that problem in a thoughtful way rather than reacting in the moment.

If everything feels like an emergency, it means the stakes are too high.

You’ve got too many eggs in a single basket or you haven’t done enough to build a stable business. And this puts you in a constant reactive state where you’re bouncing from problem to problem, hoping to salvage each situation. But isn’t permanent—at least it shouldn’t be.

Instead, imagine that you were already a billionaire. You run this business for fun just to give you something to fill your days. In that context, the stakes would be low—even arbitrary.

When the stakes are low, you can think and act more clearly. You’re not rushed or pressured.

But you don’t have to win the lottery to lower the stakes.

I personally use a combination of business strategy and personal mental models to help me reframe the business and put myself into a position where I feel more invincible than vulnerable. (There’s always some vulnerability.)

Here are some things that have worked for me.

Set Goals & Build Forecasts

This is probably obvious to anyone with any kind of formal business experience or education. But entrepreneurs come from all walks of life.

Take the time to set goals for yourself and for your business.

Then, turn those goals into some kind of forecast and action plan. Ask yourself if it’s a reasonable expectation or what you’d need to do differently to make it reasonable.

This helps you assess yourself objectively and put problems into perspective.

Maybe you lost a big sale today and you’re feeling The Dread™️*.* You can come back to your goals and forecasts to remind yourself of the big picture, assess the damage, or change your plan if necessary.

You may find out that you’re already ahead of your target and this is really no big deal. Crisis averted.

Or you may realize that you’re nowhere near your goal and you need to simply rethink your entire strategy. This sucks, of course. But it’s better to proactively make changes than passively roll through your days and only look at what went wrong in hindsight.

Build Runway

One of the best things you can do for the stability of your business and your own mental health is to simply build more runway.

“Runway” is the length of time your business could survive if you don’t hit your goal or bring in new revenue. It’s like your emergency fund—taking into account your expenses and your earnings.

If you lost your largest customers, had a cold sales streak, or had something else go wrong, would you have enough time to right the ship before you have to close up shop?

The more runway you have, the more time you have to respond to a bad situation, the more leverage you have in difficult situations, and the lower the stakes will feel on a day-to-day basis.

For us, building runway means not just having cash in the bank, but also having future revenue and growth on the horizon that will help us compartmentalize a single bad event like having a client churn.

I’ve done a few key things that have helped provide runway and stability:

• Save money (duh) - Keep enough cash in the bank to cover your fixed costs for months or years
• Get a business credit card (before you need it)
• Secure a line of credit (before you need it)
• Extend and strengthen your contracts (if applicable) - We ask for 30 days’ notice to terminate a contract. This isn’t a monumental ask but gives us time to respond if/when we have a client who’s churning
• Book future business you can grow into - A pipeline of future business will offset any dips in revenue and give you confidence about the overall growth of the company
• Invest in growth and marketing before you need it - Nothing worse than bad news and a dry funnel

Hit “Save”

There’s an old rule in gambling that says if you want to win, you have to take some money off the table when you’re up.

Take some of your earnings and pocket it. That way you can only lose what you’re still betting.

As a casual gamer, I also think about this like saving my game before I go into a difficult area where I might die and lose my progress. (I know, most games autosave these days.)

Whenever possible you want to create a “fallback” — a soft place to land if things get hairy.

I don’t have a wealthy family or a trust fund to get me by. If my business fails, it’ll hurt personally. So I’m always trying to hedge my bets and make sure that if things go wrong, I’ll have something in the tank to get me through.

I try to do this in a few ways:

• Save money personally - Be prepared to cut your personal salary or income if push comes to shove
• Build alternative forecasts - If you had to cut expenses, what would you do? Plan for that possibility before it’s a reality
• Shift fixed costs to variable costs - This makes your business more flexible
• Diversify revenue sources - If things take a turn in one market, you may have to lean in another direction (e.g., wholesale vs retail or white-label vs direct client sales)
• Diversify revenue streams - Going one step further, you can invest profit in wholly separate revenue streams that will help you build a foundation that isn’t tied to the risks of your main business

Something that we haven’t done but is also an option here is looking for investors, partners, or even an acquisition.

If you really want to “take your chips off the table,” you might consider offering up equity in the business to an outsider (or team members!) in exchange for a cash payout that will stabilize your personal financial position.

Shift to Long-Term Thinking

Another key to surviving as an entrepreneur (and making smarter, better, less-emotional decisions about your business) is shifting your thinking from a short-term to a long-term mindset.

View each challenge, problem, or fire as a speed bump rather than a mountain.

Understand that everything that could go wrong likely will go wrong at one point or another.

When you’re in the thick of it, ask yourself:

Is this going to happen again over the course of 1, 5, or 10 years?

Chances are yes—many times over.

Imagine that one of your critical team members leaves tomorrow. In the short term, this feels like a massive blow (and it may well be!) But if you look at your business over the course of years and decades rather than days or weeks, you’ll see that this same scenario will likely happen many times.

You will likely lose an important team member every few years. (Or more frequently!)

Once you realize this, it’s no longer an emergency. It’s an inevitability. And therefore you can—and should—plan for it. Your business priority should not be reacting to emergencies but executing on the things that will turn oh-shit moments into okay-we-have-a-plan-for-this moments.

Secondly, you can see that these challenges are indeed just minor setbacks in the grand scheme of things. Again, if it’s something that is likely to happen over and over again throughout the life of your business, then could it really be considered an emergency?

Over the years, we have lost dozens of clients.

But we’ve ultimately gained more clients than we’ve lost. Losing clients was a setback but not a barrier.

As Bert Cooper (Mad Men) once said, “I don’t want to have to walk down here every time we lose an account. This is an advertising agency. I’ll wear out the carpet.”

You need that perspective.

Rather than reacting to every hiccup like a life-or-death moment for your business, you can see it for what it really is—another problem to solve.

Step Away

There’s a lot of talk about work-life balance, mental health, and the other “soft” aspects of entrepreneurship.

I’m a big believer in this.

I think that having hobbies, taking vacation, and just stepping away from the business for a bit can give you the mental fortitude to make it through tough times. Working insane hours and “grinding” 24/7 may seem like the way to get ahead, but you’re paying a tax on every extra hour you work, every hour of sleep you’re losing, and every experience you’re missing out on.

That tax bill will eventually come due in one way or another.

Stepping away (even for an hour) can also make you a better leader.

Stepping away from a difficult situation or perplexing problem gives your brain a chance to better process and helps you develop stronger and more creative solutions. That’s just scientific fact.

Rest when you need it.

Rest before you need it.

Rest.

Disconnect Your Identity from Your Business

My last piece here is really sort of a “meta” solution to relieving the anxiety and lowering the stakes.

It’s to separate your business from your personal identity.

Last year, I shared some pretty personal thoughts on this subject in another post.

But just to put a point on it: You are not your business.

Some days, it may feel like your entire identity is your role as a business leader and entrepreneur. But the reality is that all of us have many pieces of our identity. We’re children, partners, parents, friends, cousins, gamers, bikers, runners, pet owners, volunteers, singers, chefs, and many other things.

We are all complex humans.

And our careers—our businesses—are only one facet of that.

When you feel at your lowest, try to remember that your failure or success in business does not determine your value as a human.

Even if you fail spectacularly at this one element of your life, you are still all of these other things.

You are still worthy.

Don’t allow your entire identity to be consumed by just this one piece of who you are.

This is something that I’ve tried to remind myself at my darkest moments. When things felt most stressful—when I felt the most dread and thought seriously about quitting—I tried to remind myself that this was just one aspect of my life and doesn’t define me as a human.

If my business fails, my wife will still love me.

I will still be an entrepreneur.

I will go on.

This has been such a critical piece for me. And at this point, I don’t feel that same hum of dread.

I don’t see problems as an existential threat to my business and my life. Instead, I see them like all of the other problems we’ve dealt with over the years. I even see some of the same problems cropping up—things we can address systemically. But, most importantly, I feel confident that we’ll be able to push through and become better and stronger.

This is perspective.

I’m not sure if this is something you can have without at least a few years experience. But I hope it’s helpful for other entrepreneurs to know that those grueling and heart-wrenching moments may feel like minor stressors when it’s all said and done.

Chances are that the worst-case scenario will seem trivial, all things considered.

Alright friends — that's the first part of my update for 2021.