5 min read

One night in August 2012, I felt completely defeated. I had been working all summer towards the launch of my first startup, MarketOSU. It was a simple idea – basically Craigslist for Ohio State students that required a student email to create an account.

For months, I had been marketing an August 20th launch date for the website, and checking in with the two guys on my team who were building the site. They assured me that everything was coming along!

Then, on August 19th, they sent me a staging site to look over. It was just about ready for launch, they said. I remember looking at the page and my heart sinking.

There’s no way we’ll launch this on time.

That night, I sent a ton of detailed, specific requests for things to change. And I waited, and hoped for the best.

Fast forward to March 2016, and I’m in the same boat. My engineer, Brandon, and I had been working towards a May 20 launch date of a major redesign of our website, Tixers.

I was on a David Bowie kick, obsessed with his goodbye album, Blackstar. I had a countdown in my bedroom for the number of days until I released this website as my Blackstar before stepping away from the company.

We were working nights and weekends in his free time to make it happen, and I was constantly refreshing pages, testing the functionality, and sending specific requests for things to change and adjust.

It’s so close. But we need to do these few things. These things would make it perfect.

Those situations always felt high stress, and I didn’t quite grasp why. Everything was coming along, and it was almost like what we wanted, but these few things could really push it over the edge!

I couldn’t code it myself, or I would’ve. Didn’t he want it to be perfect like I did?

This week, Eric and I launched the first issue of a major quarterly publication we’ve started, called the update.


The update is a highly-curated, quarterly publication of editorials, stories, and trends happening in startup communities outside of Silicon Valley.

**I could write a whole piece about why we are doing it, how we’re doing it, and so on…but I’ll leave that for this week’s podcast episode (subscribe here on itunes, search “upside” anywhere else).**

We started talking about the update back in November 5, and started advertising it in December. Originally, we planned our first quarter release for January 15, and then we realized how much work it was truly going to take.

Launch day was approaching, and at the beginning of the week, we had just about all the raw materials we needed to pull it off — we just needed to build the web page out. And how hard could that be? I’ve built several WordPress sites now.

Launches are expected to be a little messy. Reid Hoffman, the founder of Linkedin, famously said that you should be a little embarrassed of your first product or you launched too late.

As a case in point, we just passed Uber’s birthday, and this was their launch website.

But it seems as the internet matures, and tools for designing and developing online get better and better, the pressure to launch something beautiful and useful has reached new heights.

I’ve never claimed to be a designer or a developer, but I do take a lot of pride in how my work looks and feels. So I spent a lot of time in WordPress trying to make it look good.

And as I dug in, there was so much more to be done than I realized. For every item I checked off my list, I realized there were two more aspects I was forgetting.

There was the overall layout, then the design of specific elements, introducing new typeface because of previous brand standards didn’t work, thumbnails for the pieces, making it mobile friendly, defining the page metadata…you get the point.

I was sharing my progress with Eric in real time, and he was sending me changes and edits in real time. Little things – things that absolutely make the overall whole better and more polished, but didn’t he understand that there were bigger problems? I haven’t even built the actual blog pages yet!

Suddenly, my perspective on 2012 and 2016 was totally different. I understood why those moments felt tense with my developers. I understood that they were worried about core, fundamental pieces, and I was looking at the details.

And I also understood exactly what Eric was feeling, because I’d been there too.

It’s so close. But we need to do these few things. These things would make it perfect.

Empathy is powerful.

By the time it was ready to make public, I had spent so much time looking at it that I couldn’t zoom out and look at the macro anymore.

Is this even good? Will anyone care?

Sometimes in the past, that question would stop me from even sharing it with the world.

But people seemed to think so, and the feedback keeps rolling in. It’s always scary to launch something new, but damn does it feel good to see people use or enjoy it.

PS: Obviously, I’d love for you to check it out. And if you’re feeling generous, a quick RT on this tweet goes a long way.