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

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).

Mid-day the conversation turned from investment to acquisition. This was unexpected, but delightful.

We finished @defunkt's quick trip the next morning with his first baked oatmeal experience. He flew back to SF on a full stomach and still raves about that oatmeal. 😂

The Offer

Two weeks later Steve and I flew to SF to meet with all the company leaders. They presented a pitch and threw out an offer. The neatest thing I can remember is @defunkt demo'd an early version of Atom (this was Dec 2011).

My strongest memory is of our time in the situation room (the fancy office in GitHub HQ 2.0). It was blazing 🔥 and both sides were nervous. Not one of us had been involved in an acquisition. Just a bunch of sweaty rookies. 😅

GitHub offered the usual – jobs with salaries and benefits, some cash up front and stock options.

Steve and I have always been focused on long term value, so we countered with double the stock options.

GitHub knew what they had. So they countered with double the cash. Ooooooohhhhh do I wish I'd negotiated one last time for any additional equity. Live and learn.

Lesson: Never accept the first offer. Always negotiate. Even though we didn't get more equity, we doubled the cash by countering once.

Happy Birthday 🎂

On November 25, 2011 (my 30th birthday), we accepted. The hilarious thing is we started at GitHub on December 5th, effectively on a handshake. Needless to say the lawyers weren't very happy on either side.

After a few months of legal back and forths, we finally just told the lawyers to agree on something so we could all sign and be done.

Lesson: Create and sign the paper work first. I've done a handful of handshake deals in my life and they've all turned out great. But that is insanely rare.

Hello Old Friend

Speaker Deck never really went anywhere at GitHub. It grew and people used it, but it mostly sat in maintenance mode.

In 2017, a few people contacted support about buying Speaker Deck from GitHub. At this point, GitHub was so successful that even taking time to vet a buyer and do the deal wasn't worth it to them.

Due to my history with Speaker Deck and the fact that I was maintaining it on the side at GitHub anyway, I volunteered to vet a buyer.

Why Not Me?

Then, it occurred to me. I wanted to be the buyer.

But why would a company sell a product to an employee? Well, if you trust the employee, its a win/win. 😎

GitHub gets to move Speaker Deck to a new home. The new home is trusted and vetted. They don't have to shut the service down. That's a PR win for them. Due dilligence isn't necessary because I created the app and was maintaining it. I knew what I was getting into.

From my point of view, it was also a win. I got a creative outlet to work on something small that I controlled. GitHub was thousands of people at this point, which didn't leave me with much control over anything.

I made an official offer to acquire Speaker Deck from GitHub in August 2017. It took a while, but they approved in December. They even cut the offer I made by 90%. They basically gave the site to me. Super cool. 🤓

Lesson: You'll never know if you never ask. The worst result is they say no.

Closing the Deal

But months later, there was no movement on the deal still. Then, out of nowhere I got an email in June 2018 saying they wanted to close immediately.

I was like sweet! Friday, June 4th, 2018 we signed the paper work and Speaker Deck was coming home.

Microsoft Comes Knocking

Little did I know the reasons behind this quick change. A day later, I was at the park with my son. I got a text from someone saying there was a rumor that Microsoft was acquiring GitHub.

There had been many rumors of different big companies acquiring GitHub during my time there. Normally, I took no stock in rumors like these – other than using that big fake number to calculate my fake net worth. 😆

But this rumor felt different.

Why had the Speaker Deck deal suddenly closed out of nowhere after months of no change? Microsoft owned LinkedIn, which owned SlideShare. I could connect the dots (not that Speaker Deck ever factored into Microsofts decision, haha). It had to be true.

And it was. GitHub had to know that Speaker Deck would be dead if they were acquired by Microsoft, so they quickly shipped it off to me. And it lived on. Again, super cool. 🤓

The Second Reign

Following the Microsoft acquisition of GitHub, I took some time off. We (Steve joined me on this Speaker Deck venture) didn't really do anything with Speaker Deck (other than a redesign and some ugprades) and floated the bills for it (low thousands a month) for nearly a year.

At some point, we decided to put some tasteful ads on it to reduce the out of pocket each month. For a while, it broke even and a few months it even made money. But then covid hit and advertising revenue went nearly to zero 📉.

Steve and I knew we needed to do something to stop the bleeding. We had a mutual friend who was interested in it and considered cutting our losses and selling to them.

Instead, we rolled up our sleeves and went to work on making it profitable. You know, crazy idea, right? Charge people for your software.

We added multiple new features (following, notifications, private decks, priority uploading, scheduled publishing, etc.) over the next few months and launched several of them as a Pro account last December.

My hope was that within a year Speaker Deck would break even. The great news is that each month since charging money (including the very first) Speaker Deck has generated more revenue than expenses.

And last month between the MRR and ad revenue, it is now sustainably making money each month.

Lesson: Charge money for your software. Charge more than you think people will pay. Do it now.

Goodbye Old Friend

So how do I get from sustainably making money to selling Speaker Deck again?

About a month back I was stressed. And I'm pretty sure Steve was as well. I hate feeling stressed. Some stress is unavoidable. But all my stress was self-inflicted.

Trying to push 3 apps (Box Out, Speaker Deck and Flipper Cloud) forward with 2 developers (Steve and myself) can be frustrating.

We're only going to work so many hours in a day, so our options seemed like:

  1. be satisfied with each app inching along.
  2. contract out some help for 1-3 of the apps.
  3. get rid of an app.

We were never going to be ok with option #1. I know we can make great products. My goal this time around is to learn distribution.

I want to see if I can make a product grow faster. It just seems like a fun thing to learn. Growing faster is the opposite of inching along.

Lesson: When you aren't sure, diversify. When you are sure, concentrate and focus.

Getting Some Help

So we started down the path of #2 above. For sanity's sake, it was time to get help.

Our plan was to each set aside a chunk of our money for Fewer & Faster. This chunk plus Speaker Deck's profits could fund contracting work on Speaker Deck until it could fully fund itself.

I knew what needed to be done on Speaker Deck. But just didn't have time to do it. Contracting would make it possible to move the app forward without me being stressed (maybe). We could get help with spam fighting, support and development work.

An Afternoon Call

Unrelated, Steve and I were chatting on the phone one afternoon about adding a new person to Fewer & Faster. I was pacing back and forth in my office, still feeling a little stressed from the mountain of work that could and should be done, when Steve was like, "We should just sell Speaker Deck."

I had the same thought in the 🚿 the day before. But hadn't said it out loud to anyone – even my wife. I agreed and immediately reached out to our friend again.

They were still interested. They made an offer a few days later. We accepted and closed the deal Tuesday of this week. I worked with them to transfer every thing. It's done.

Speaker Deck has a new home. And I'm excited about that.

I'm excited that now I have only 2 apps to focus on. My primary focus will continue to be Box Out, but now any other time can be funneled to Flipper Cloud, which is really my passion, instead of split between Speaker Deck and Flipper Cloud.

We didn't sell Speaker Deck for the money. Its likely we could have shopped it around and made more. We sold it to focus.

Also, I'm excited for my friend – who was already helping us a bit with several Speaker Deck related things. Now they can take the reins and make an impact without feeling like they have to wait on Steve or myself to respond or approve or build.

I'm already seeing how fast they are responding to support requests and wishing we would have done this a month or two ago.

Lastly, I'm excited because I finally helped prove that Speaker Deck has value and can be a business, which I believed a decade ago when we started it.

Its making money. Its growing. That's neat.

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