Super Bowl weekend is upon us. So let’s make some predictions.

1. Puppy Bowl will be as awesome as ever.
2. The Super Bowl Ads will underwhelm. I’ve already watched most of them and so far…meh.
3. Katy Perry’s halftime performance will be interrupted by breaking coverage of Aaron Hernandez’s daring escape from prison and into University of Phoenix Stadium where he will hold Tom Brady hostage until someone answers his questions about deflategate.
4. Patriots win in a blowout. History has shown that only Eli Manning can stop Tom Brady in a Superbowl.

Happy Super Bowl-ing!

There’s an old saying that goes: “The bigger they are…” – I forget the rest 😉

I was just speaking with a co-worker about how companies like McDonald’s and Samsung – once the vanguard of their industries – have suddenly come crashing down, hit the ground, went through the ground, kept going, and then took a left turn in Albuquerque. Meanwhile across town, Apple sets a world record for most profitable quarter EVER and Shake Shack prepares for a highly anticipated IPO.

McDonalds in particular leaves me scratching my head. Burgers, Fries, and Milkshakes. How do you screw that up? I could venture some theories but it really doesn’t matter.

In the end, I think we’re witnessing the cataclysmic decline of what was once an the icon of American Entrepreneurship, success, and capitalism.

Maybe it’s the millennials? Maybe something that big has to collapse under it’s own weight? Personally, I think they need to  bring back the McDLT.

“Keep the hot side hot and the cool side cool”

Words to live by.

I like to write. Writing relaxes me, it’s cathartic. So it’s puzzling to me why I can never seem to find more time in my day to post a blog. A sentence, a thought, or maybe just an emoji 😄

I suppose it’s human nature to postpone, procrastinate, and to put things off ’til later…then again maybe I’m just a lazy ass.

So let’s try and reboot and find the time to do the things that matter. There’s always time, just like there’s always an excuse. Everyone has a choice.

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”