Agency Year 1: Make All the Mistakes

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Instead of belaboring another tale of failed startup to development shop, we want to help others learn from some particularly painful challenges we overcame in our first year of action. Leggo.

How you know it’s time to shutdown your startup

After running our startup for 10 months, the project was our baby. We became addicted to (vanity) metrics like traffic and design awards and used that fuel to keep us going. But even without those results, man it was sooo painfully hard to give up.

Your loyal users, expert mentors, and closest friends invested their precious time and energy in your startup so there’s an overwhelming responsibility to continue building. But over time, the labor of love completely drains you—especially when it’s not a real business. Even at that point it took one of us to finally call it quits before the journey was over.

Pro-tip: Each month take a hard look at where you’re at financially, stress-wise and with your passion for the project. You won’t know whether it’s time to shutdown or not, but you’ll have useful data to realistically think through your current situation.

How we got our first clients

We’ve done a bit of freelance work with professors and friends in the past, but since we were completely focused on our startup, our network had severely shrunk.

When the time came to figure out how to get clients to pay us to build stuff, we were at a complete loss. It was embarrassing being partially-formed adults and struggling to pay rent, but it also meant it was time to be vulnerable.

We just cold applied to freelance jobs.

We (mistakenly) didn’t utilize any great connections or word-of-mouth, instead we just emailed like everyone else. We’re not completely delusional—going to MIT, getting incubated and building a company for a year is a non-trivial amount of experience—but seriously that didn’t matter at all. Our first client took us on only because we understood his problems.

We can’t emphasize this enough, but providing value to your clients is entirely based on you deeply and intuitively recognizing their goals.

How we did it: We read through the entire company blog (which is no small feat) and took each of his four starter questions as seriously as a college essay. In the end we knew so much about the company and had thought critically through their important issues, that our phone call made it seem like we had worked there for years.

Pro-tip: Design and code are just implementation details. Focus. On. Goals.

Having a background not in tech

Not having a background in tech is for sure a challenge, but similar to how we got our first client, the only thing that mattered was that we understood our client's needs.

You see, we’re both architects—the kind that design buildings. Working in the architecture industry for nearly a decade, our experience isn’t exactly applicable to digital design. But strangely it sorta is.

Architecture as a service industry is just like a digital agency and for the most part we have the same roles: talking to clients, designing iteratively, and building the final project. Yes of course the medium is different (websites vs building) but the process is so similar that it’s kinda freaky.

Whether you were a musician, lawyer, painter or biologist in the past doesn’t really matter. Solving problems with your existing skill set is the ultimate normalizing factor.

Pro-tip: Don’t tell anyone you’re a blank, tell them you can solve their problem.

Dealing with unhappy clients

Daaaaamn we messed up. So many times. From scope creep to choosing clearly the wrong framework, our clients had to put up with some rough decision making.

Look, as an agency this is going to a happen. You’re too often making seemingly rational decisions on limited data and have to go with your gut.

Clearly explaining the logic and soothing things over is in everyone’s best interest (good wine helps too). Yes mistakes happen, but accepting the consequences and compromising for a solution will endear you to the client, and often a strong relationship will evolve. Plus you have a better perspective on the issue when it inevitably arises again.

Pro-tip: Don’t mess up :) …but actually when you do screw up, own up to it. Being transparent and human breeds leniency.

Working with friends as clients

Don’t do business with friends is such a repeated mantra it’s gotta be a thing right? We learned if you want to go against common sense, you have to be explicitly open.

With friends the issues are mostly surrounding money so know that going in. Be up front about the costs associated with a project, for instance a website costs $x0,000 because it takes a designer, developer, and ongoing maintenance…

But then, hook your friends up. Everybody likes a good deal and as long as they are aware the Friend Discount is deeeeply discounted, it clarifies what is and isn’t possible. Put the actual costs on both the proposal and the invoice.

Ultimately you want your friends to succeed (if you don’t that’s a completely separate but understandable position :) ). This year we took on 3 friends as clients and the only goal was to help them expand their businesses. And truthfully seeing our friends’ succeed is just as fulfilling as seeing our own business grow.

Pro-tip: Tell friends how much things costs and why. Then hook them up.

Should you work for free

This answer took years of deliberation (and it’s still a work in progress) but ultimately we believe, Yes!

Similar to working with friends, Dann Petty (@22:34) gave what I consider the best argument: Do work you like with people you like.

The value of design is a tough sell because it isn’t directly tied to revenue. And it’s an even tougher sell to young companies because they’re so resource limited.

But we always do our best work for projects we deeply care about and truthfully it doesn’t matter how much we get paid. Doing a super dope starter project for a company that you love has a whole series of unexpected repercussions: the company doing incredible well and inadvertently promoting your work, design awards, and even just an opportunity to try something new that’s fun.

Pro-tip: Free work has a dirty stigma, but ignore the haters. Do work you like with people you like!

What skills from the startup are actually useful

So “cop out” since it’s kinda broad, but the most useful skill has been without a doubt marketing abilities. Yes we write way better code and our designs have definitely improved, but the ability to get 150k people to our website in 3 months was insanely valuable.

That ability led to us directly getting clients, and also independently building projects that made money based on—you guessed it—getting traffic. We built HTML Arrows and HTML Color Codes both as useful tools and as ways for us to create passive income.

We now believe marketing is the most important skill to develop when starting a business that has product/market fit (customers). If you are a programmer or designer and want to start your own gig, stop right now and learn marketing. A great place to start is Patrick McKenzie’s blog (a self-proclaimed geek who turned marketing into a game-like engineering challenge).

Pro-tip: As two introverted guys who just love making stuff it’s tough to admit, but learn marketing. The challenges and projects you get will exponentially increase both in profitability and sophistication.

So where are we

Hot damn, that was a bunch of advice.

So we’ve only been an agency for a few months, but clearly we’ve learned a lot things not to do. For an interesting post next year, we’re hoping to make a ton more mistakes but also have a few learnings along the way.

If you’re really itching for more unsolicited advice, want a shoulder to cry on or need a dance partner, holla! As always beers and advice are on us, reach out on twitter or

Thanks to @AndyStone and @Calebarclay for reading drafts of this.