Double Burrito Day

On Tuesday, I had the honor and opportunity to speak at Digital East 2014. Afterwards, several people congratulated me on the recent sale of my company and asked ‘How does it feel?’ It all happened so fast I never really had a chance to think about it, until now.

Leap: Interrupted

In the Spring of 2008 I decided that I wanted to pursue an MBA. So I quit my job, took the GMAT, and began the process of applying to MBA schools. It was a decision that surprised most of my friends and family, but the timing seemed right…right up until the moment the sub-prime financial crisis went thermonuclear. Suddenly an MBA didn’t seem like the wisest investment. Suddenly nothing seemed like the wisest investment. Day by day, I sat and watched as the market sank into the seventh layer of hell.

Miracle On The Hudson

By January, the economy – and stock market – had gone from bad to worse and from worse to Weird Al Yankovic (Even Worse). Then a funny thing happened on January 15, 2009. Still weighing my options, I turned on the TV that afternoon to learn that US Airways Flight 1549 made an emergency landing…on the Hudson river.

Later that evening, my big sister and I were texting back and forth about the miracle when she asked:

Carina: “How bad is it?”

Lenny: “Bad. Really bad”

Carina: “You need to go back to work”

Lenny: “Yeah, I do”

So I did as I was told and I went back to work as a Software/Business Intelligence Consultant. And for a few months things were good, but it wasn’t enough. I still had an itch that needed to be scratched. So in the midst of the worst economic recession since The Great Depression, I did what any insane person in my position would do…I quit my job (again) and started an iOS app consultancy.

Leap Then Look

In the beginning, it was just my co-founder and I and we ran the business out of his basement. Keep in mind that when we started the company, Blackberry phones outsold iPhones by a wide margin, barely anyone knew what Social Media was, and Netbooks were being hailed as ‘the next big thing’ in computing. In hindsight, we look like psychic geniuses. But the reality is, we had no idea where the market was going. We were just having fun building apps.

It was tough sledding the first year. There were a lot of nights where I thought we might not make it. But we kept grinding it out and eventually we were able to grow the business and then hire a third and then fourth employee. I think the turning point for us was when we realized that the basement bathroom situation could not support a fifth employee. It was starting to get gross downy here. In order to grow the business, we needed to find some real office space – which wasn’t exactly cheap in the Northern Virginia / DC Metro area. So we went out and signed a lease for a small office space. Looking back, it’s not as though we really had any other choice. At some point you have to push all-in or slowly bleed to death. So we pushed all-in, but I remember looking at the company’s bank account and realizing that unless we signed more clients, we only had enough money to run the business for another two months.

SaaS: My favorite palindrome

Slowly but surely we grew the company. We signed a couple of big clients, a few startups, sprinkled in some gov’t work, and by the end of year three, we had more than doubled the size of the company. From our first office we moved into a bigger office – and bigger bathrooms! Things were going well. So when Howard (an old boss) called and asked about acquiring my company, I was reluctant. But five weeks later we had been acquired by a Geo-Marketing SaaS startup.

The Leap Home

Since the acquisition a lot of my friends and family have asked (and wondered) why? On the surface, it wouldn’t appear as though my new home has a whole lot to do with ‘mobile’ or apps. They’re not wrong, but they’re not right either.

Consider this: Twitter began as Odeo, Starbucks began as a maker of espresso machines, and remember when IBM made computers?

“To improve is to change; to be perfect is to change often” – Winston Churchill

Too often I run into people that have nothing more than an idea and they call themselves entrepreneurs. But that offends me because it means they want all of the reward and none of the risk. I think being an entrepreneur means having the courage and conviction to stand at the edge of space and leaping towards the earth. No net and no parachute.

How does it feel to have sold my company? … Not bad 🙂

Happy Pivoting!

“the more detailed you estimate, the more the total will tend towards infinity”