My Entrepreneurial Seizure


The Moscone Center was quickly receding, sitting perched in the middle of this chilly sun washed San Francisco street. There were palm trees and the sunlight unnaturally bright; a stunning cityscape painted over a layer of griminess. This morning, there is no hint of the scene that played out in the week before. The reason I was here.

I had flown in last week to attend a software developer's conference. This was no ordinary conference with morning donuts and talks on best practices. This was Apple's World Wide Developer Conference or WWDC. At that time in 2008, WWDC was the only place in the world where you could go to find out how to code iPhone apps and sell them directly to millions of Apple's customers.

Most of the 5,000 people who would jam into the Moscone Center that week believed that they would be building the next big amazing thing. Many had already built amazing things. These people were Apple's techno-elite and their world was about to explode in a way no one could predict.

I too was here to build something. What I wanted to do was build a wine note app and sell it directly to people with just my laptop. I wanted to start a business in my garage but I wanted it to stay in my garage and remain small. A lifestyle business.

But, I had a big problem: I had no idea how to build an iPhone App or really any kind of software. Three months ago I had never even used an Apple computer. This was why I stood in the long line that snaked it's way through the city streets waiting for the Moscone doors to open.

This morning I was waiting to hear from the person who inspired me three months ago to believe that I could build something that people might buy. That person was Steve Jobs.

Hearing Steve Jobs speak those three long months ago set off a chain reaction in my life that ultimately brought me here to the opposite coast, alone. A few days after hearing that keynote I bought the cheapest Mac I could find so I could try to learn how to build apps on my own. I conceptualized my first app idea. Events snowballed and I started listening to the Internet Business Mastery podcast which in turn inspired me to get obsessed with becoming an entrepreneur.

By the time I was waiting in this line in the cold San Francisco street I had already invested in a new Macbook and started to think of this app project as a business. Including this trip, I had invested almost $4,000 to get to this point.

I was in the midst of what Micheal Gerber dubbed The Entrepreneurial Seizure,

"An entrepreneurial seizure is the moment the entrepreneur decides it would be a great idea to start his or her own business. It's when one believes that knowing how to do the work of a business is all one needs to understand in order to start and grow a business." Micheal Gerber, The E-Myth

In short, I was doing all this to learn how to do the work of a business. At the time I didn't know who Micheal Gerber was and it would be years before I fully felt the impact of my entrepreneurial seizure. But, that's a story for another day.

The excitement became palpable as we finally shuffled into the conference floor. Hip sounding but unidentifiable music played from all the speakers. Groups of guys huddled together, each group with it's own chief holding court who had already built indy apps for Mac or even corporate apps for BlackBerry.

We tried to coolly ignore the former vice-president Al Gore and this cabal of attendants. But, the presence of the big-shot adds to the sense that something big is going to happen here. All of us, even Gore, were swooning in breathless anticipation of Jobs. What would he say?

When Jobs finally takes the stage, he every utterance is met with woots and claps. We are all mesmerized. Much of the keynote are housekeeping items like this item on the number of developers who were given the accreditation needed to publish apps on the store.

"But first, the iPhone. In the first 95 days, 250,000 people downloaded the iPhone SDK. 25,000 developers applied, and 4,000 were admitted. " Source: CNET Live Blog

I was not one of those 4,000 people who were admitted. Even if I managed to learn enough to publish I could still be out of luck if I wasn't approved by July.

Jobs also talked about the how successful the iPhone had become after being launched only one year ago. He paraded a series of developers who had already finished apps really for sale on day one of the app store.

After Jobs keynote, the week would continue with me furiously taking notes and attempting to understand the iPhone SDK. Each night the conference would spill out into the streets to be continued at local bars were we would share our plans for conquering our worlds. Eventually the alcohol would drive us back to our rooms to sleep off the buzz.

By the time I found myself in that cab, speeding away from the Moscone Center I was determined to make my app business work. I would visualize how many apps I would need to make the past three months "worth it", asking myself questions like:

  • Will I sell enough apps to cover the $100 developer certification fee?
  • How many apps do I need to sell to recoup the $4,000 I just spent?
  • How many apps I would need to sell to quit my job?


I can feel my stomach tighten as I walk into my manager's office in the Princeton NJ office where I work as an analyst for the Educational Testing Service. I was about to talk to my boss about reducing my hours to half time so I could work on my business.

On the plane trip back I had been furiously working on my app, Wine Pad, and it was clear to me that to get to my goal I would need time. I knew that I needed to get this app ready for the launch of Apple's new App Store in only a month or so. The technology was changing everyday and the whole process was uncertain. I was under the gun, but determined to make Wine Pad happen.

The idea behind Wine Pad was simple. If you go to the gift section of most book stores you will see "wine journals" that are basically notebooks with special pages designed to take notes on wine tasting. So, you will see areas on each page for the type of grape, what the wine smells like, the vintage and so on. It's the kind of thing you buy for 10 bucks to stick into a gift basket with wine bottles to mark an occasion.

A Wine Book Example of a Wine Tasting Note Book

Why not make an app that was like one of those notebooks except that it would always be with you on your phone? And you could snap a picture of the wine label to make it easier to remember. It would be just as good, if not better, than those notebooks at the gift shop and I could sell it for as low as 5 bucks. This idea was simple enough for one person to take on.

Eventually, my boss and I come to an arrangement. I would work 20 hours each week split into two and half days. We would try this for about six months or so before reassessing. My boss was thinking that this was a short term action and that things would go back to normal by the end of the year. I was thinking about how I can use the iPhone camera to save wine labels in my app.


I breathe a sign of relief, as I sit in my upstairs home office in the late July afternoon. After weeks of intense work, major setbacks and big technical glitches the App Store opened on July 10th. Wine Pad, version 1, was complete and submitted to Apple for review.

This is what the first version of Wine Pad looked like:

Wine Pad v1

Wine Pad Screenshots

Wine Pad's underpinnings were about was simple as they could be as well. The most notable technical achievement was the inclusion of a SQLite based library I coded myself used by the app to persist each wine note.

The road to this point was uncertain and full of frustrating setbacks, the worse of which was that I had to work on this project before my developer certification was even approved.

I had been working on learning iOS and switching to Mac since March and I had been frantically working on Wine Pad for weeks at this point. If my developer certification was not approved, all this work would have been for nothing.

Not only had I finished Wine Pad over the past month, but I had also filed the paperwork I needed to start my company, opened up business bank accounts and credit lines, I started a blog named Going Indy, and I set up a web presence for the new company that I dubbed App Shop, LLC.

The App Store launched on July 10th and while my app had been submitted it was not available yet to buy.

Everything hinged on Wine Pad getting accepted into the App Store, but Apple's system was still glitchy and once I submitted the app I didn't know what to expect.

Filing paperwork, opening bank accounts and web hosting had set me back another $1,000 and if Wine Pad was rejected it would have been all for nothing.


With my laptop propped on my knees in front of the TV, I furiously type out a 6:38AM blog post on Going Indy.

Wine Pad was finally accepted into the App Store at the end of the first weekend. This was a huge relief, and this was the first chance I got to record this success in my blog.

Among other things, I was excited to finally call myself an entrepreneur:

"Now, I can officially call myself an entrepreneur. Since Sunday, I have gotten about ten emails and 8 official reviews so the product does seem to be selling. Most of the feedback has been positive or has suggestions that will go into the next update of Wine Pad."

This was a key moment, up until this point in my life I had never sold anything at all. Now, I was selling software to people all over the world. I was a completely different person on that Wednesday than I had been on that March afternoon five months ago when I watched the keynote where the App Store was announced.

I was finally in business, I could see reviews and I got emails. My business website was getting a ton of traffic. I was tentatively hopeful that my sales would cover the $100 developer certification. Mostly though I was exhausted.


Sitting at my favorite window seat, at our downtown Starbucks, I try to figure what to do about Wine Pad. Things soured less than a month after the heady launch of Wine Pad. I leaned in and wrote on my blog that:

"The setback this week is that I cannot get an update published to my Wine Pad product. This is very frustrating since I worked on that thing day and night.

Also, if the preliminary numbers are at all correct many people have bought the app and are affected by its shortcomings. I do not want to lose this audience, however if I really cannot get that fixed I need to consider re-publishing Wine Pad so I can get the right features in."

I had worked day and night to update Wine Pad which had a minor bug and needed more features. However, because something went wrong in the original code signing process I just couldn't update the app. There was no way to get help and Apple didn't respond to emails. This was devastating.

I somehow managed to attract many customers for the first time in my life. But, it about to all go to shit because the app wouldn't work for all my users. I had a fix but I couldn't get it to my audience. My product was out of my control.

While there were no reliable analytics from Apple during this time I know that my initial audience was in the thousands. If there was a time to establish a brand on the App Store, that July would have been the perfect time.

Looking back, it's clear that this was a pivotal moment. My app could have been the beginning of something big. Instead, this stumble put me into a situation where I had to start over from the beginning. Because of the code signing problem I couldn't even use the name Wine Pad.

I had to remove the app from the store, I lost my audience and I had to start over. This experience with Apple was a red flag, but at this point I was hooked so I doubled down and released a version 2 of Wine Pad that fixed the problems and included enhancements.

Many customers who purchased the original Wine Pad were angry. It looked like a money grubbing move and they said so in the App Store comments. This hurt my brand. Wine Pad represented the best I could do in coding, branding and marketing. The apps that came after were all just attempts to recover from this stumble.

A smarter person may have quit at this point. But, for me the idea of even making one sale was humbling. Selling hundreds of apps felt like validation at the time so I blindly moved forward throughout the Summer and into the Fall.

In spite of the problems, by the end of the summer I had exceeded the $11,976 figure that I had in my head since my trip to the west coast. This was the figure that I needed to reach to consider quitting my 9-5 job.


Cool October air rushed past me as I walked along one of the main hiking trails that honeycombs the ETS campus in Princeton. Recently, I started receiving wires from Apple. This was my share of the profits from the apps sold in July and August.

I had never seen numbers like that coming into my bank accounts before. Those first few payments were over $10,000 and they seemed to come all at once. It appeared that my business was working. I had a decision to make.

These spontaneous hiking trips were happening more and more frequently while I was at my day job. Even when I was at my desk, all I could think of was my apps and my business.

I was restless. My boss could see this too and we were in the second half of my trial half-time status. She wanted to start talking about what projects she could line up for me early next year.

The idea of leaving such a comfortable situation that I worked so hard to build over the past 8 years seemed crazy. I was at a turning point, the signals that I was getting made me believe that I had a chance to do something amazing and on my own terms. That dream that I dared to consider out West was happening, but I had to decide if I would embrace it.

I was really torn up over the two choices I had in front of me.


Standing at the edge of a nearby lake in Langhorne, Pennsylvania, I push aside waves of dizziness and uncertainty. Yesterday was the last day of my job at Educational Testing Service, a job that brought me unexpected success in my late twenties and the place where I met my wife Stacie.

In many ways, ETS was the best thing that had happened to me up to this point in my career. As a psychology major with few options for a high-paying career ETS provided a real career that actually payed the bills. I learned the kinds of STEM skills that made me employable.

The day before was like many days at ETS that revolved around a lunch. The programming team gave me a nice send-off at Contes, an weirdly popular pizzeria in Princeton that we went to often. The day ended with hugs, stories other about people who had left and finally a exit interview.

That day was the first day since I graduated college over ten years ago where I had no obligations and I wasn't worried about money because I had created a passive income stream with my apps.

I spent most of that first day in an introspective fugue. Only a year ago I balked at the idea of even buying an iPhone. It seemed risky somehow. Now I was somehow willing to upend every single part of my life to create something I didn't even know existed a year ago: a lifestyle business.

I was completely free. For now. And I had absolutely no idea what I was supposed to do...