10 lessons in 10 years: The odyssey of a brand agency founder

January 1, 2019

On January 1, 2009, after years of studying and freelancing on the side, I launched as Enve Creative, offering web & graphic design to small businesses. Following years of steady, cyclical expansion (and plenty more studying), on January 1, 2016, I relaunched as a full-service strategic and creative agency rebranded as 816 New York.

Ten years. Ten years of gaining and losing. Of grueling weeks and stress, then victories and rewards.

Here’s what I’ve learned:

Do the Work

1. Tame the interaction.

If you can’t imagine a workday not spent checking for and reacting to messages, you’re suffering under the illusion of productivity. Close Twitter, quit Facebook, avoid Instagram. Social media is the illusion of reality.

Due to the brain’s circuitry, humans are constantly switching between two states of awareness: being either task-positive (actively focusing on a task at hand) or task-negative (wandering or daydreaming). “Seesawing” too rapidly between these two networks can leave your brain feeling “dizzy” and unable to commit to either state. (“How to Actually Stop Checking Your Email All the Time“)

Recalling one morning of 27 red Slack flags… I wanted to go back to bed. I refuse to install the app on my phone. I don’t check email after 7:30 PM, never before my first cup of morning tea, and rarely on weekends. My cell phone number is private.

If you could be creating, but you’re not—if you often feel disoriented—pay attention to how much time you’re spending aimlessly interacting or seeking out interaction.

2. “Good news: We can move through this quickly.”

I am in love with the 15-30 minute call. Short agendas with one or two items. Even with 3+ people, the shorter the call, the more focused it is. The more joyous, even.

Shave 30 minutes off any call by instead sending an email with action items, deliverables, and deadlines. Coordinate specifics person-to-person, rather than looping in peripheral people.

Be Human

3. Reward and challenge your team equally.

For some, it’s not easy to relinquish the Captain of the Ship role. Whether you’re steering a 15-foot sailboat or an 860-foot battleship, your crew sees things on the horizon that you haven’t seen—or can’t see. An article. A piece of correspondence. A podcast. An edit. A remembered teachable moment from a past job… Whatever it is, those are gems—always, always listen.

• Shut up during the meeting.
• Let them put their expertise to work.
• Ask for help and insight, and wait for it.
• When the business reaches a milestone, share it.
• Surprise them (a Grubhub gift card with “Dinner’s on [Business Name] tonight” has miraculous powers, I swear).

Honor your team’s strengths, admit your mistakes and weaknesses, guide when and where you can, and absolutely keep your sense of humor.

4. Brainstorm. Brainstorm. Brainstorm.

I’m the least consistent about this. I shouldn’t be. Because it returns me to me and my purpose every time.

Take a day, at least once a month, and get out of the office. Whether you read an industry book, check in with staff members to learn their goals and ideas for the coming months, or camp out in a park or coffee shop, take a notebook (preferably paper) and brainstorm for your business.

Think BIG. This is “no bad ideas” brainstorming. I ranted about this a few years ago; read it here.

Take No Prisoners

5. Smart trumps churn any time.

Speaking of rants… don’t get me started on the amount of bullshit content out there. I’m surprised servers aren’t spontaneously combusting at this moment.

Own your voice. Be smart. Stay out of the mudslide of pervasive superficiality, the mindless churn of “marketing experts” filling content calendars. Don’t imitate your competition—pave your own way.

Trust me, it works. For as small as our agency is, our monthly newsletter far outshines the industry average. Our latest edition’s open rate was 29.2% (avg: 18%), and click rate was 7.3% (avg: 2.5%).

Your audience is far smarter than most marketers will tell you. They’ll sell you on high churn for big numbers—called vanity metrics—that fluctuate wildly.

Don’t dumb yourself down, or you’ll attract the weakest kinds of clients and the least loyal customers. And bots. Many, many bots.

6. Name your willing sacrifices.

What’s more lonely than ambition? Lacking support.

Since starting this business, I’ve sacrificed a very conventional life: marriage, house in the suburbs, dual incomes. Particularly in those early years, all on my own, it was do or die—it was about survival and (sometimes) blind faith. In the last few years, I relaunched the brand with clearer purpose, quadrupled our revenue, and hired staff.

Not everyone could or should do what I did. It was back-breaking and isolating, but also fortifying and uplifting. Every win felt like a BIG win. Every loss was a challenge—I learned to detach from outcomes, to keep moving, always moving… When failure isn’t an option, you find a way.

Have faith in you.

You will disappoint and irritate people. But your purpose is not a villain. Be grateful for those who stand by you, and be patient with those who love and miss you.

As for the rest, decide at which point you’re willing to say, “Fuck ’em.”

Define Your Boundaries

7. Obsessively stay in your lane.

Consistency speaks volumes to your intended audience. More than the size of your business. More than the breadth of your services or your portfolio of work. Your messaging/tone, graphic style, content delivery systems and schedule, the way you present in meetings (online, phone, or in-person), your communication style in formal and informal settings—all speak to your unique identity.

Be that.

Don’t try to be everything that everyone else is. Decide what you won’t do. Which services you won’t provide. Find partners, and publicly honor those relationships. Identify what you do best, and be consistent in every way about how you project it to the world.

8. Toxic clients can’t plunder a strong fortress.

In my early years, I attracted bullies. I was young, desperate for clients—in total survival mode.

Until I realized I wasn’t growing my own business—I was only growing theirs.

No. Bueno.

I would rather live under a bridge than deal with the heart attack–level amount of stress brought on by clients who enslave their staff and contractors, while liberally spraying out manipulation or anxiety.

RUN from these people. They will do nothing for you but distract you from where you should be.

For fuck’s sake: Enjoy the Ride

9. Relax into the work.

Nothing is more stifling to creative flow than pressure and expectation. Often that pressure bleeds out of an overstuffed inbox, a moment of impatience unrelated to work, or some other uncontrollable stressor. And suddenly the work feels like work.

That’s not why you became an entrepreneur.

Working from that headspace means everything takes twice as long and contains more errors. Take 15 minutes to breathe. Or to walk around the block. Or to silent-scream, if that’s your thing.

Step away. Get back to the joy.

10. Be kind to you.

Be generous to yourself and others.
Be open.
Be free.