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Before jumping into the lessons we’ve learned, let’s first dive into why we were able to learn these lessons. In early October 2010, my future cofounder, Joe Donohue, and I were caught in the oddest workplace whirlwind we’ll ever experience (I say this with confidence, at one point the FBI broke down a door). Without going into too much detail, and to save you a rant-filled article wherein I go find that nearest whiskey bottle, let’s just say it was the perfect storm of incompetence and neglect. The silver lining was the team that was assembled there—with at least four local businesses rising from the ashes.

Shortly before the implosion of the aforementioned company, we arrived at work one day to find an odd feeling in the air. The owner of the business, who only visited on special occasions when he needed a website quickly “wired up,” was in the lobby with the person pretending to run the business. We could see what was coming next. All 27 employees were called downstairs for a special meeting that included several cases of beer. Everyone was being laid off and the company was shutting down, just over a year after launching.

So there we all were, beer in hand, listening to the alligator-shoe-wearing business owner deliver a speech that was muffled by my own thoughts of what the next steps were going to be. Then my lack of concentration was broken by a friend who stood up and said “Whelp, see ya later,” and walked out the door (that guy would later team up with another employee to start a great digital studio). Some Q&A continued while most of the fired employees packed up and walked down the street to get another drink.

When Joe and I joined that company we had both started businesses and freelanced in the past, so the concept of fending for ourselves wasn’t quite as scary as it may have been otherwise. We had also seen the writing on the wall and had begun discussing what our next steps may be if things were to go south—or completely crater, as this case ended up.

Within a couple weeks, Mostly Serious was born.

Earlier this month, Mostly Serious turned five years old. Beyond the obvious benefits of turning five, like getting branded coozies and pens, we have also been rewarded with a wealth of knowledge derived from the lessons we’ve learned along the way.

Mostly Serious is an interactive agency that specializes in creating and managing brands, websites, applications, and other custom solutions for our clients. We also build products of our own, and that has taught us just as much as our client projects. Having walked down both paths in our five years, there are advantages and disadvantages on both sides, but neither could survive without the other—or at least we couldn’t survive without both. Client work pays the bills and presents new opportunities while our products keep us up-to-date on new technologies and maintain our sanity. Sometimes you just need to build something to build it.

We were self-funded and started out of a bedroom in my house, which we shared with a couple dogs and later, as our first hire, my future wife (we were already dating, that isn’t a tip). We have always focused on building the type of company we would want to work for and attracting like-minded people who want to help us build it. That was our plan then and still is today.

What we didn’t know was almost everything else. I am a designer by trade and Joe is a writer, a combination that works fantastically for an interactive space that regularly struggles with the concept of creating content, however it’s not the best combo for sending invoices and cutting checks.

Within our first year we hired a project manager/office manager/help-us-fix-all-of-these-things-because-we’re-seriously-going-to-lose-our-minds person. I will echo this below, but when starting a business, hiring a lawyer and an accountant immediately is vital. I knew about the first but not the second. I really wish I had.

Over the next four years we would achieve many milestones: landing our first international client, hitting double digits in employees, launching an internal product, renovating our ideal office space, working with some of our favorite local companies, and getting branded coozies made. Seriously, every company should have those.

We would also mess up a lot. And I mean a lot. Our clients that have stayed by our side have experienced a few of those bumps with us, but they knew we would learn from our mistakes and move forward as a better company that offers better services. As a testament to the power of relationships built on trust and hard work, our first client, Holloway America, is still with us today.

Although there are some basic problems that are consistent for almost every company (like who is going to do the dishes) there are also going to be many, many unique hurdles along the way. That is why knowing how to handle problems in general is much more important than knowing how to fix a specific problem. Being aware of the processes to follow will alleviate a lot of the overwhelming aspects of starting and running a company and make problems less difficult to manage.

This list may act as a roadmap on how to handle problems. Mostly, it is going to be a personal reflection on the fastest five years of my life.

1. Choose Carefully.

Every new interactive agency will choose at least three crucial components that will shape its future:

  1. Cofounders
  2. Employees
  3. Clients


Have you ever gotten married to someone because they had dated some people you knew previously and it hadn’t gone too bad? I mean, he clearly had experience and wasn’t crazy, so why not, right? That’s how insane it seems to start a business with someone you haven’t worked directly with for a long time.

Cofounders are for a startup what location is for real estate. You can change anything about a house except where it is. In a startup you can change your idea easily, but changing your cofounders is hard. And the success of a startup is almost always a function of its founders.”

Paul Graham

Managing a relationship with cofounders is a unique experience. Although I hinted at a comparison with marriage, that isn’t an accurate representation. Agreements are an absolute must, but there are many questions that should be asked early in the selection process to find out if that person is a good fit for the business and the other cofounders. Some of these questions should definitely be:

  1. Are you prepared to devote a large portion of your life to this?
  2. How much time can you commit to this business?
  3. What percentage do you plan to own?
  4. Is there anything in your life that will make this company a secondary interest?
  5. What are your compensation requirements?
  6. When will you give up?

Although I knew some of these questions before starting Mostly Serious, others have come while building this company. You will be in the trenches with these people. You will celebrate with them. You will disagree with them. You will have to resolve conflict and move on with them. And sometimes you won’t be able to resolve the conflict, but you‘ll have to move on because there are other people who require the company to advance.


Early in our company’s history we stole a line form Valve’s employee handbook, which states that “…any time you interview a potential hire, you need to ask yourself not only if they’re talented or collaborative but also if they’re capable of literally running this company, because they will be.”

Our team is our most valuable asset. It isn’t even close. Second place is probably the coffee pot. A loophole often overlooked by businesses, especially startups, is the power of an engaged team. In the startup hubs, points are given to early hires and titles are handed out to assist in future placement after the app has cashed out or been acqui-hired by Hooli.

From left to right: Maranda Provance, Spencer Harris, Aimee Hendricks, Jarad Johnson, Lucy Howell

Although we offer some of the standard perks, like equity in the business our employees are helping build, we are more focused on the impact each person can make. Like Valve, we embrace the concept that every single employee should be able to run the company. They should be able to steer us toward success and away from risk. They should feel invested, because they are.

This requires an almost unreasonably high set of requirements when we expand our team. We have hired roughly two people per year since opening, and each of those hires were both difficult to find and immediately obvious when we did find them. Some companies will hire every talented engineer they can get their hands on, but those companies are clearly demonstrating their lack of respect for company culture.


We turn away nine out of every ten potential clients. Sometimes the budgets don’t match, sometimes the timelines don’t match, and sometimes our teams don’t match. There is a false belief held by those who have not worked in the client-service space that a lost project is lost revenue. That is not the case. Every new client comes with opportunity cost.

Even if you’re hungry, even if you‘re desperate, never work for a bad client.

Massimo Vignelli

A very basic way to illustrate this concept is to consider where each path will lead. If you choose to work with clients who under-value your time, that effort will result in more clients who further devalue your work. If you work with clients who provide the trust, resources, and assistance that leads to a successful result, your efforts will bring in similar clients. Choose your path carefully, because when you commit to doing cheap work for assholes, it will be difficult to dig back out.

Since creating clear selection criteria and turning away potential clients who don’t match up, we have seen the quality of our clients — not to mention the results we can produce—increase dramatically. Although it can be hard to turn away clients when the pipeline is low, it is absolutely worth the short-term losses in the end.

2. Hire Smart People. Then Trust Them.

Every new employee must be capable of running the business. If that rule has been met, the next step is to provide the freedom necessary for employees to effect change and build something of their own.

At Mostly Serious, the ability for bright people to positively impact the company is built into our structure. We do not place arbitrary titles on people purely based on their history with the company. Even the founders must earn their positions every day. Although “partner” has been used to denote those with vested equity, we’ve recently removed even these titles in place of what we label an organic structure.

When we launched in 2010, Joe and I had agreed we would implement an entirely flat structure. We had always been fond of Valve’s approach and believed we could build a team capable of utilizing a very similar approach.

The flat concept worked effectively through our first two years.

After a couple large projects saw one too many bumps for our team to accept, we began asking questions about our process, team, and relationship with our clients. The solution we found would require two large changes:

  1. We would divide into departments and assign heads to each based on a previously demonstrated ability to perform in that role.
  2. We would overhaul our processes across the board, an exercise led by the new heads of each department.

One year after implementing these changes we found that nearly every issue we were experiencing had been remedied. In the process, we had abandoned our flat structure in favor of something that fit our team better—an organic structure, closer to the way Valve operates on a team level.

This change was not in line with the original vision of our company structure, but our team determined it was the right solution to our problem.

3. Make the Tough Decisions.

Our company structure was not the only thing we’ve had to correct. Making the wrong decision is common for every startup. What is important is how to respond to being wrong.

I’m a very stubborn person and I hate losing much more than I enjoy winning. This can extend itself in areas it is not welcome, like making business decisions or trying to understand how my buddy Dave can possibly think the Oklahoma City Thunder have more talent on their team than the Golden State Warriors, which is just absurd and wrong. See?

Around a year into our existence we brought on two additional partners to assist in an expansion effort that would bring on larger clients with more complex problems and create an internal product company, which we ran similar to Google’s famous “20% time” (which appears to not actually exist). For those unfamiliar, Google claims to provide employees an entire day to work on side projects. Naturally, we felt this would be the perfect model for our team to build and release our first internal projects.

This was probably the greatest learning experience of our five years. Not only did we build three different products (and released one), we also shut them all down within a year.

Shutting products down is hard. At this point, we had spent well over a year building them, often spendings nights and weekends on them to avoid disrupting client projects. But when we looked at the situation objectively, it was clear that we had created a money pit — more precisely, three money pits.

The reasons for our initial product failure has been well documented and will likely land in a followup article, but it was clear at the time we would not recover from those mistakes. The right decision was to shut it down.

4. Edit Your Company.

One of the primary causes for our initial product failure was a lack of focus. Instead of building one product the entire team could rally behind, we split off and simultaneously created three primary products with several others being started along the way. We had no focus.

There are a thousand things that we could be doing, but there are only one or two that are important.

Jack Dorsey

We don’t have a CEO. Mostly because we are a 10-person company; if 5 of 10 people are executive staff, it’s purely ego stroking, not helping to improve the business. At the time, we also didn’t have a singular person leading our product ambitions. This led to a chaotic environment where a very small team was building products other people on the same team couldn’t even understand. Instead of utilizing all of the resources available to us, we were splintering and only utilizing a small percentage of our team.

We have since built editing into our company in a variety of ways, primarily by acknowledging our misstep and striving to edit ourselves better in the future. We’ve all heard that business owners must learn how to say no often… and now you’ve heard it again.

5. Hire a Lawyer & Accountant.

Find these people immediately. Do not pass go, do not talk to a logo designer (or your nephew’s friend), and don’t start looking for an office. Go get recommendations and buy each a coffee. Get close with them because you’ll be in this long ride together.

6. Embrace Your Community.

When Cosmo Kramer decides to hang photos of everyone in his apartment complex, Jerry doesn’t like it. Don’t be Jerry. Your community needs you and you need your community.

We’re located in Springfield, Missouri, a small Midwestern town filled with some great and some terrible people. You might have heard of us as the town that hates nipples and gay people, but I promise we’re working to fix these setbacks.

We love Springfield. We ask every potential new hire what they love about Springfield and how they are making it a better place to work and live in. Our team is involved in a number of efforts to improve our city, including Springfield Creatives, Springfield Community Gardens (we even built that website), and, started by our own Maranda Reynolds, The Geek Foundation.

Most importantly, your community needs you. Even in cities not quite as malleable as Springfield, there are still small pockets that can enact very real change. Find like-minded people and do something to make your life better and help those around you.

7. Work Hard.

Starting a business is not easy. It is very hard. I personally believe most startup successes come with an overly romanticized story of sacrifice and dedication, like the claims that Elon Musk worked 23 hours a day. But it’s not terribly far off if you’re unreasonably dedicated to your goals.

I’ve watched, and been a part of, 48-hour-pushes without sleep, months of 18-hour workdays, and I’ve slept under and on desks many times. Every company leads a delicate balance between dedication to meet goals and abuse of talent. I would never ask anyone who works for me to put in more time than myself, which helps, but eventually you have to acknowledge the limitations of productivity.

We aim for six hours of productive time per day. These are billable hours put toward the creation of client or internal products. Although most people are working for around eight hours a day, we trust that everyone on our team will find the right balance to achieve maximum productivity.

And when push comes to shove, everyone is going to do whatever is necessary to meet our deadlines and commitments. There is really no replacement for hard work when necessary.

If you’d like to know more about our approach, follow up with the piece I wrote on our office hours and work-life balance.

8. Productivity Over Office Hours.

My first real job was at a sign shop, where I would show up at 8am and work until 5pm, with a 30-minute lunch break somewhere between. I hated it. I woke up at 7:15am and three snoozes later would rush to get ready and fly in the door just before 8am. I wasn’t as productive as I should have been because I wasn’t considering my production. I was showing up to fill a slot of hours.

We wanted Mostly Serious to be different. We have no office ours, outside of one person who self-assigned themselves hours because he works better that way. Everyone can, and should, come and go as they please. Our goal is to give our people the tools they need to work whenever they are most productive. For some people, like myself, that’s early in the morning and late at night. For others, it’s the standard 9-to-5. And for some, it’s small sprints throughout the day broken up by walks, going to the gym, meals, and so on.

Henry Ford brought new ideas to a stagnant workplace philosophy that reshaped the workday in America. As outlined in my article mentioned above, “Work-Life Bullshit,” we use this knowledge to drive our own policies:

Henry Ford revolutionized the workday in America by introducing the 40-hour workweek and making weekends commonplace in 1926. Lest you believe Ford was anything but a ruthless businessman, he was clear that he took this action purely as a business policy and not for humanitarian reasons. He correctly believed that rested employees were more productive and more likely to purchase the same products they were pumping off his assembly lines.
Ford’s brilliance paid off, showing increased productivity and, in 1927, expanding to his office workers. Slowly, the 5-day, 40-hour workweek became a national standard. Since its implementation, it has largely gone unchanged, with greed taking the place of innovation, as corporations utilize part-time loopholes to leave impoverished workers relying on government financial aid just to get by. Looking at you, Walmart, you disgusting warehouse of waste.

9. Fix Things Quickly. Move On.

Shit is going to go bad. At some point, one of those tough decisions will need to be made. Make the decision and move on.

One of our clients, People Centric Consulting Group, educates companies on the dangers of toxic employees. We have had toxic employees. This isn’t to say that these employees were incapable or even wrong, but their vision did not match our company’s vision. We waited too long to remove these people and, after doing so, immediately saw the positive results. When things aren’t working in your company, they will spread like a cancer and infect everyone and everything around them. Remove the cancer, and your company will very quickly be back on track.

This absolutely is not relegated to toxic employees. From large to small, dealing with problems immediately and effectively will do wonders in allowing a business to grow safely and intelligently. We’ve fired one client in the history of our company and it was absolutely the right decision. Again, it wasn’t that they were bad people or we didn’t want to do the work—our visions simply did not align.

10. Your Office Doesn’t Matter (Until it Does).

Remember our first office? It was a slanted bedroom in my house. We had to arrange the desks in a way that avoided people sliding away from them. It was tight; it had just enough room for four people to squeeze into; the air conditioning just barely worked upstairs; and dogs regularly needed you to stop working and take a very important petting, walking, or bathroom break. We loved it.

Not only did we love it, but people would regularly come work out of our bedroom office. There was excitement there, knowing we were building something and all we needed were computers, time, and whiskey.

We’ve had three actual offices since then and we now work in a renovated space that fits our culture and workflow perfectly. I remember near the end of our tenure at our second office—a quiet, dark space without many windows and a conference room blocking the only natural light in the office—we could feel the morale just wasn’t quite there. Something was off.

I remember Joe mentioning that the new office, which we had just started tearing apart, would pick everyone back up. That seemed silly to me. We started out of a bedroom and were beyond excited. Where we were was much, much nicer. Why did we need an office to bring back that drive?

There comes a point where hard work requires a payoff. Something to remind you why you’re doing what you’re doing. For some, that’s launching a product or a cause and seeing people react. For some that’s a new gaming machine or television. For our company, in that moment, it was an office space that we would all genuinely be excited to spend our days in.

It worked.

hat’s five years with Mostly Serious summed up in ten topics. While building a company that encourages us to live the lives we want, life has continued happening, sometimes quietly and sometimes very loudly. Three babies, and a fourth coming in a couple weeks, have been born to our team members. A friend and coworker moved to the left side of the country, allowing us to open an office in San Francisco. Some have experienced loss and heartbreak.

I guess what I’m trying to say is, the lesson we’ve learned most of all is to build something that enhances your life. You spend a lot of time working, creating, and building—that time should make you happy. It has for us.

Here’s to five more. 🍻

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