How to build an app, get acquired by GitHub, buy an app back from GitHub and then sell it again

Let's set the scene. The year was 2010. Twitter was exploding. Instagram just became a thing. Myspace was formally dead.

Speaking of formal, my attire was cargo shorts, a t-shirt and crocs (classic clog of course, likely tan to match my shorts) – aka "the nuneform".

I was standing at my standing desk and hacking while my feet rested effortlessly in the most delightfully comfortable shoes in the world.

Scratch That Itch

Speaker Deck started as a happy accident. I mucked up a command line call to imagemagick and passed in the path to a PDF instead of an image. To my surprise, an image was returned.

Was it really that easy to convert a PDF to images? It was.

From there, I knew all presentation building apps could export to PDF. I also knew that showing off a presentation was basically just an image gallery where the images are shown in a particular order.

Steve and I were hustling our products at conferences. We were also both teaching at the University of Notre Dame. A by-product of these acts was a lot of slide decks to share.

We weren't fans of the experience on SlideShare and thought it would be neat to whip something together.

Lesson: Scratch your own itch. Take on giants in huge markets (at least then you know there is a market).

Jon Hoyt was looking to do more programming and hanging out with us more often. So Hoyt started hacking on Speaker Deck. We hired him a few months later. We often joke that Speaker Deck was his job interview.

Lesson: Do some work together before you officially work together.

Speaker Deck launched in September 2011, three days before RubyConf in New Orleans. All of Ordered List loaded up in a van and road tripped from south for the conference.

Go To That Conference

One afternoon at RubyConf, I was enjoying the "hallway track" with @defunkt (founder of github if you don't recognize the OG handle) in the bar at the conference hotel. He was asking about Ordered List and I was asking about GitHub (44 people at the time).

Lesson: Conferences are about the friends you make, not the talks you listen to.

We usually ran into each other at conferences. So I didn't think much of it other than enjoying the chat. RubyConf ended and the Ordered List crew piled back in the van to head back north to Indiana.

Then, it happened. Saturday. 4:25pm. Ding.

A new email from @defunkt with the subject: Investment.

A single paragraph in length, including a 💵 amount and a compliment. WOW.

I still remember my stomach flipping and an immediate smile. Positive feedback always feels great, but from the CEO of GitHub? Heck yeah!

We weren't looking for investment. But how can you say no to that?

I immediately text Steve and he was pumped too.

I wasn't sure how to respond so I waited and tried to not think about it.

Sunday. 24 hours later. Ding. New email. It was @defunkt again. The email started with a completely unnecessary apology. Remember I hadn't responded because I was still reeling with excitement, not due to offense. He also included a huge pitch about how awesome we were and how he could help us (as if we didn't know how much he could help us). He said he could be in South Bend as soon as Wednesday to talk more.

I didn't make him wait after this email. Rarely were Steve and I too busy to meet with anyone. But we were that week. So I told @defunkt his email was awesome and that I'd get back to him in a few days.

Lesson: Silence is a super power if you can live with occasional awkwardness – both in conversation and negotiation.

@defunkt, Steve and I met up the October 27th in South Bend. We spent the entire day talking about possibilities at our office (the tiny tower pictured below).