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To Get Your Business Off The Ground You Have To Start Ugly

Wandering Aimfully Through Starting A Business

To Get Your Business Off The Ground You Have To Start Ugly

The first version of your business, product, or service is always going to suck.
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

At this point in my entrepreneurial career, I have about 30 projects under my belt. Some have been very successful. Some have done just okay. Some have been complete flops. But they all have one thing in common: they started ugly.

You might think that project 29 or 30 started out perfectly, right? With 20+ previous experiences, I had to have figured out how to avoid all the mishaps, errors, and ugliness that go along with a new project.

Here’s a secret: every time I start a new project, even I think it’s going to be different this time. But alas, it’s not. Every project starts out with a hideous mess of disjointed ideas, thoughts, sketches, and assumptions.


Starting Ugly Means Different Things To Different People

For the sake of this article, I’m defining ugly as:

Ugly: A version of my product I’d be embarrassed to show a potential customer.

The project I’m going to share with you throughout this article is called ofCourseBooks. A project I previously co-owned with friends Paul Jarvis and Zack Gilbert. The three of us came together with the idea to create elegant embeddable workbooks.

But guess what? Things didn’t start out elegantly at all.

The start of any project requires an ugly duckling phase

Sketches on paper. Really quickly thrown together designs. A bunch of bad ideas tossed in a Trello board. All of these things are necessary when starting a project.

It is 100% impossible to get a project from initial idea to beautiful and ready for the world in a straight, linear fashion. Instead, it looks more like this:

Start ugly

Yeah, it looks like a mess, and yeah, it often feels like things might crash and burn at any moment.

But here’s the hidden beauty in the ugly duckling phase…

If you accept that this phase of a project is necessary (or even mandatory), you can look at it from a completely different angle. You can embrace the ugly phase, and you can use it to your advantage to create without criticism or judgment.

With ofCourseBooks, we didn’t worry about everything being perfect from the beginning. We just allowed ourselves to create the first version of a logo. The first version of a branding guide. Definitely the first versions of the website framework and design.

And how many iterations did each of those “first versions” end up having?

Paul, Zack, and I all have experience working on previous projects, which helped us understand that things wouldn’t be perfect on the first go-round. We came together as a team and had conversations about letting go of perfectionism, and about our willingness to create new versions of things —without complaining about the extra work.

Just because you start ugly, doesn’t mean you have an ugly duckling of a product forever

This is where the word “iteration” actually means something. It’s not just a buzzword, people! It means making changes quickly and without hesitation. It means throwing away hours of work that no longer serve the greater good of a project. It means swallowing your entrepreneurial pride and realizing that no one ever makes anything perfect on the first, second, or even third try. Shifting your thinking in this way can help you reach the next milestone or level of success faster than you’d imagine.

I remember what it was like pining over designs for various projects, or even over words for various articles. It was tedious, nitpicky work. And it wasn’t until I made the big shift in how I defined the success of my art that I began to understand and embrace that my ugly ducklings could quickly become majestic and powerful mallards!

Nowadays, especially with writing, I just sit down and know that the first version doesn’t have to be perfect. There is no perfect, and an ugly duckling is okay. This single thought has completely removed writer’s block from my vocabulary and life.


Sharing The Ugly Can Actually Be A Great Marketing Tactic

People don’t need the perfect picture to be interested in buying something.

I learned in 2015 that people don’t need the perfect picture to be interested in buying something.

In 2015, I wrote a daily journal for 60 days on the writing platform Medium. In that journal, I shared my heart, soul, and ugly thoughts about what it took to create my next big project (BuyMyFuture). I was scared to publish many of the daily entries I wrote because they were ugly and vulnerable. One, in particular, was titled, “Does anyone even care?” Here’s an excerpt:

Every single day I think to myself: “Does anyone actually care about this journal or my new project?” That’s simply the honest truth. I believe a lot of people who are creators (or business owners) can relate to that feeling. When you’re working on something, even if you have validation of the work you’re doing, it can feel like there is a lack of public interest because the amount of interest could never possibly match your effort. I’ve poured well over 200 hours into Project Galaxy [BuyMyFuture] already. Not to mention the hours that other people have poured into this project. The small moments of public validation are fantastic, but it would take an insurmountable amount of them to match up to the hours that have been invested.

A funny thing has happened over the years as I’ve shared my vulnerable and relatable thoughts: People have trusted me and purchased my imperfect products.

I can actually quantify the value of sharing the REALNESS with the BuyMyFuture project. Over half of the 165 buyers of BuyMyFuture said they read the Medium journal and that it influenced their buying decision!

Being relatable and willing to share my ugly helped generate over $80,000 in one project alone.

(The first year of BuyMyFuture was sold at $1,000 per spot.)

Don’t think of yourself as a marketer? That’s okay, focus on being a content sharer instead!

Going back to ofCourseBooks, we shared a public Google Doc with our podcast listeners and email subscribers. In that doc (as you can see), we shared all our ugly versions and a bunch of our thoughts along the way. Remember, our definition of ugly may vary to your definition of ugly.

And surprise, surprise: many of our founding members say they purchased when they did because we shared the behind the scenes (read: ugly versions). They saw the progress and knew we’d continue to improve our next versions of the product.

Make a mantra to start ugly and embrace its usefulness.

Say this out loud: “I know this is the ugly phase. I’m 100% okay with making mistakes and having to redo work.” The more you say it, the better the outcome of whatever you’re working on will be.

Whether it’s writing an article, building a piece of software, designing a new logo, or all the other millions of ways you can create things nowadays, be okay with having an ugly duckling phase. Understand how beneficial it is, and shift your mindset from worrying about it to leveraging it in the creation of something even better.

Be okay with starting ugly. It doesn’t last forever, but it’s completely necessary.

To Get Your Business Off The Ground You Have To Start Ugly

(Big Fat Takeaway)

The first version of your business, product, or service is always going to suck. Starting ugly is a right of passage. Embrace that as a fact and you'll make a ton more progress.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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