The Worst Time to Launch

Creating a business while the world masked up, scaled back and shut down

By Matt Steel
22 June 2020

At the beginning of summer in the year when every day felt like Tuesday – aka 2020 – I left a well-paying job and launched a new business with only one client.

Covid was in full effect. In the US, riots bloomed like wildfire from Seattle to DC. Social and political upheaval surged on every continent. The words economic crisis hung over the world like a motionless thundercloud that could burst at any moment.

It was a hard year to start a business, but I know I wasn’t alone. Other people started businesses in 2020, of course, especially near the end of the year as lockdowns and restrictions began to lift. That said, I suspect many of them planned longer, saved more, didn’t have several kids.

What was I thinking? People rely on me. My wife, Leslie, is our family’s coo (read: her very full-time job is caring for our children and managing our home). The kids? Two girls, two boys. Eight eyes looking to Leslie and me for guidance and care. Forty growing fingers, forty fidgety toes.

Hunker down and hang on till the storms pass, said the lizard brain. Responsible grownups earn regular paychecks, said conventional wisdom. This is an awful time to start a company, said almost everybody else.

At the Crossroads

I’m all for responsibility, but I never cared much for convention. The timing? Better to start with why. To frame my purpose, I’ll turn to the artist and author, Elle Luna. If you’ve read her soul-stirring visual essay, “The Crossroads of Should and Must,”1 you might guess what I’m about to say. If you haven’t, either read it now – I’ll wait for you – or bookmark it for later.

Here’s a sliver from her beginning.

“There are two paths in life: Should and Must. We arrive at this crossroads over and over again.

“Should is how others want us to show up in the world – how we’re supposed to think, what we ought to say, what we should or shouldn’t do. It’s the vast array of expectations that others layer upon us. When we choose Should the journey is smooth, the risk is small.

“Must is different … [it’s] who we are, what we believe, and what we do when we are alone with our truest, most authentic self. It’s our instincts, … the things and places and ideas we burn for, the intuition that swells up from somewhere deep inside of us.”

At the crossroads of Should and Must, I believe timing matters very little. We aren’t in charge of time, after all, and our best plans are just guesses. Choosing Must is a terrifyingly simple matter of doing or not doing.

Must arrives unexpectedly. For me, it tends to come after and sometimes within deep prayer and solitude. Must is clear. Must is calm and overwhelmingly vibrant. It’s like standing on the rim of an erupting volcano in total, unshakeable equanimity.

I reached the crossroads of Should and Must, or rather it reached me, on a walk with Leslie on a bright Saturday afternoon, April 4, 2020. And I knew, I just knew in my bones what I had to do.

To learn contentment in all things: this is vital. But working against the grain of your own design is destructive. It dishonors God. It dishonors the people who raised and nurtured you, even if they’re the ones telling you to play it safe.

For some of us, for the misfits, the path to responsible providence and even long-term stability requires breaking molds and bucking systems. Even when the world is coming unglued.

I ran a design studio from 2009–2013 and was a partner at another agency for a few years after that. Since then, I’ve learned a thing or twenty about business management. In 2020, I lept again and my prayer is that this is my final leap. Not a startup, but an end-up. A last job. Something to leave for the grandkids. And this time, I wasn’t alone. I set out to build a brandworks and design practice with a partner. A brother, in fact.

Jon Steel enlisted in the US Army in 2008 and was nearing the finish of an overseas deployment as I wrote the first draft of this story. He began in the Infantry and moved into Firefighting, Combat Engineering, leadership training and logistics. Outside of the Army, Jon has advised and invested in several successful ventures. He’s sold everything from mountain bikes to investments and wine. Jon makes friends everywhere he goes. He talks straight and pulls no punches. There’s no façade and zero bullshit with Jon. He could sell backcountry camping to Coco Chanel.

Jon leads business development, finance and operations. As an avid outdoorsman, conservationist and land rights activist, Jon brings a strong affinity for environmental and social justice to our studio. 

I do what I enjoy most and have done since 2003: guide clients through the creative process from start to finish.

Naturally, we called it Steel Brothers.

The Design Problem

One word sums up all of our reasons for starting this practice: design.

I’ll unpack that in a bit. First, I’d like to reflect on my time at Parisleaf, my last job, and express gratitude to the bosses who befriended me and showed great kindness to my family.

When I accepted the job at Parisleaf, I wasn’t sure if I’d ever come back to self-employment. But, I was certainly ready for someone else to shoulder the burden of business development. Chad and Alison Paris provided that and then some. 

I got to work and the work was medicine. In less than four years, I had the joy of leading the creative process for dozens of large and small projects, more than twenty of which proved to be portfolio-worthy. Our work brought clients to happy tears on a few occasions. We rebuilt the agency’s creative team. I began to understand and practice brand strategy. I began to learn how to lead.

For the Cade Museum,2 we fused influences from Monty Python and Marshall McLuhan to form a witty and inquisitive identity. We designed a color-drenched exhibit that graces the Museum’s central rotunda.

We helped Walker Architects articulate their purpose and position, which they used the next day to pitch and win their first-ever eight-figure contract. Eighteen months later, we watched them flex their brand identity and turn a dilapidated Bob’s Big Boy into a chic new studio.

I incorporated the Enneagram into Parisleaf’s branding process, resulting in brand narratives and identities based on real human motivations and attributes. Qualitative discovery was already happening at Parisleaf, but the Enneagram component brought a more authentic dimension to the work. In turn, those brands proved to be vital money-making and culture-building tools for clients. We gave this approach a name: Essential Branding. Chad and Ali took a gamble by allowing me to weave a piece of what Ian Cron calls “spiritual technology” into the branding process. It’s unusual, it’s powerful, and I’ll keep using the Enneagram in my work and personal life until I’m dead.

We brought Crippen, a Central-Florida accounting firm, out of the design doldrums. We rewired their brand platform with a focus on the results they provide for their clients: simplifying the business of business.

We helped Chestnut Hill, original purveyors of the Dunstan Chestnut tree, navigate a complex communications challenge. We gave them a unified brand strategy and identity with branches that speak to two very different markets.

We partnered with Cala Luna, a boutique hotel in Costa Rica, to identify what they’re all about: We’re here to wake people up in paradise. We delivered a lyrical visual identity that celebrates liminal spaces and the joy of savoring life with all six senses.

We accidentally rebranded the City of Gainesville. Fast Company wrote about it.

Chad and Ali entrusted me to lead them through the rebranding process. We changed Parisleaf’s logo and much more.

In April 2018, Chad and I were driving back to Gainesville after a business trip. He asked, “If you could boil Parisleaf down to one word, what would it be?” My immediate response: “Purpose.” Turns out, he had the exact same word in mind. Now, everything they make is grounded by purpose – helping clients discover their “why” and make their mark. 

I designed a symbol that reflects the insight it takes to bring essential truths into the light. Today, Percy the owl soars on their website and business cards.

From this perspective, the job sounds plum, right? But as I said before, there was a design problem.

Bringing Back the Knives

Shortly before I left Parisleaf, I saw an interaction between two agency owners on Twitter that grabbed my attention. One of them remarked that “The one thing they never tell you about starting a company is don’t do it.” The other wryly quipped, “You know that thing you love doing? Wouldn’t it be great to manage people doing that?”


Granted, I wasn’t an owner at Parisleaf, but I was part of the leadership team and that quip hit me square in the feels.

Running a business is a creative activity. Mentoring is creative. Creative direction – obviously. I love all of those things. Teaching people and watching them hone their chops over time – it’s magical. 

But what if you also love coming up with ideas and using your actual hands to bring them to life? What are you supposed to do if that love never fades, if authorship lives at the very center of your being? What if your interaction with the work is mainly reviewing other people’s work, leaving you feeling like a penniless window shopper on Madison Avenue? You paint or write poetry on weekends, but that doesn’t quite fill your cup. You studied graphic design (or English, or farming, or brain surgery) so you could do it, not graduate from it. You feel torn and inauthentic. Are you broken?

Imagine a chef whose first love is cooking, but eventually, she takes a job as a food critic. Let’s pretend this is the typical path of advancement in the culinary world. In the early days, she apprentices for some gastronomic guru, works on the pastry line, opens her own bistro, sells it, then becomes the food editor of Garden & Gun. The story she tells herself is that she’s being responsible. The travel perks! The shorter workdays! Food is still in the picture, even if that only includes consumption and critique. The writing is fine; everything’s fine. Her knives still see occasional use for the odd dinner party or Sunday brunch.

And yet… and yet. She’s always hungry. She doesn’t know why.

As the head of a small team at Parisleaf, I often had to roll up my sleeves and pitch in. I was glad to do it. But I was rarely the project lead; that’s not your typical creative director’s job. A cd mentors the team, reviews work and shows it to clients. At bigger shops, they never design or write at all. 

The model works for many agencies and in-house teams. But I came to realize it is not for me.

As I remember these hunger pangs and the desolate feeling of penniless window-shopping, I sense envious competition leaking through. Envy is wrong and toxic, especially when it directly affects the people you’re supposed to lead and inspire. Envy fosters discontentment and resentment. But if we notice the desire that stirs envy, we may discover that we’re fighting against the good and wholesome parts of our nature. Sometimes the best way to battle our demons is to lay down our arms.

If and when Steel Brothers grows to the point of hiring a select few full-time creatives, we’ll operate like the city-states of ancient Greece: a small fellowship of largely autonomous, senior-level makers. My name may be on the door, but I’ll be just another monk in the monastery, drawing leviathans in the margins and helping clients figure out how to communicate in a world that won’t stop yelling.

In my last months as an employee, I came to terms with three things.

  1. I was made for independence. I have a vision for the kind of place where I can do my best work, and it doesn’t include having a boss. And at the same time, having a trusted partner means greater focus, going farther and staying clear of self-absorption.
  2. I need simplicity. You wouldn’t know it from the gabby yarns I spin, but this value is a vital corrective. Take one pill a day for the next five decades and call me in the afterlife, says the doctor. Do more with less, as I’ve told the team at Parisleaf. Simplify, says Thoreau. Stop gibbering, says you. Simple is elegant. Simple is really freaking hard.
  3. It’s okay if I, if you, if anyone doesn’t fit someone else’s definition of creative director, marketing director, cmo, ceo. If that’s true, don’t send yourself back to the factory or put your pencils into storage. Make your own damn mold. Serve and lead people from that place.

Jon and I are very different, thank goodness. But the differences are complementary, and our common principles of authenticity, grit, independence and simplicity will anchor us “in any weather,” as the Florida fight song goes.

When we moved to the Sunshine State in 2016, I thought the entrepreneur in me had gone tits up. Whether that guy was deceased or merely comatose, he’s awake and roaring today. He isn’t broken and he isn’t alone. And if any of these words resonate with you, then take that as hard proof that you are not alone, either.

I’m grateful to Chad and Ali for the many lessons, laughs and words of comfort. I’m grateful for all of Parisleaf’s wonderful clients who believe in the power of branding with purpose. I’m grateful to Gretchen, Elisa, Kendyl, Kyle, Jessica and Abbey for putting up with my shortcomings and more dad jokes than anyone should have to endure. God’s peace to all of you.

To Jon and our clients and comrades: I choose Must today and always, and my family and I choose it with and for you. My knives are sharp, polished and ready.

Let’s get cooking.

Notes & References
  • 1

    Read Luna’s essay here. Fair warning: radical career and lifestyle changes may ensue.

  • 2

    All of these links will take you to project pages on Parisleaf’s website. I’d show them here if I could! Also, they changed some things on their site after I published the first version of this story in June 2020. It seems the Enneagram left along with me. Essential Branding is no longer part of their positioning. In fact, they’ve repositioned and rebranded the agency entirely. Alas, Percy’s nowhere in sight anymore. C’est la vie, c’est la guerre.