But the times, they were a changing. People like to say that change is good, and for the most part it is. Where would we be without change? Probably still eating raw meat and living in a cave somewhere. So yeah, change is good, but it can, and often does really suck. It’s often like quicksand, you can fight it and struggle, or you can slowly work your way through it. I’ve done both. I’m guessing so have you.
I’ve been a Founder, CEO, COO, lawyer, real estate broker, writer, producer and healer. As an entrepreneur you have to accept that change is part of the job description. That doesn’t mean there aren’t days you’re huddled in the corner, trying to will it away, but for the most part you learn to roll with it.
After a decade of running my first company with an amazing group of partners and people we had to shut the company down. In two years we went from one of the fastest growing companies in the U.S. to having to close our doors. Almost ten years on, that’s a change that still stings. But I hope that some of my experience can help other people.
Looking back, even at the high point of my first company, I was looking for an exit, telling my partners I wanted out. I was making money but I wasn’t fulfilled. It wasn’t exciting anymore and I was bored. I wanted change, but when it came I fought with everything I had to keep things the same. Change came anyway.
After that I really needed a break and studied with Alberto Villodo, a modern day shaman who teaches the healing ways of the Inca. It was also at this time I delved wholeheartedly into Zen Buddhism with Roshi Rich Hart, and that began a ten year practice, whose lessons I still live by today. My sister Vivian, an incredible healer, and I traveled Europe working with people and teaching workshops. As much as I thought I was helping and healing them, they were helping and healing me. It was an amazing time. When you get hurt by life, like broken type of hurt, sometimes you need to call a timeout, and take care of yourself, and find that joy again.
After practicing for a couple of years I decided to come back to New York and try my hand at real estate. I had friends and family in the business and it seemed like a good opportunity. I opened up my own brokerage and began my new career. I mostly focused on commercial and residential rentals, and it felt good to be negotiating deals again. Real estate is a simple business. Someone has a property, someone wants a property and it’s your job to bring them together. The trouble starts when people get too emotional. When AI starts taking over negotiations, deals will get done quicker.
As much as I enjoyed my time in real estate, I knew that I had to get back into technology. Maybe to prove something to myself. Maybe to prove something to others. And probably a little of both. It’s one thing to leave something behind and it’s another to be forced out. I felt like I didn’t leave on my own terms and I wanted another chance.
Over the next five years I probably started five different companies, looking for that feeling I once had. A marketing company, a video production company, a real estate app, a gifting company, and a chat bot. Some worked better than others. Some were funded and some were boot strapped. Among so many other things, I gave talks, presented at national seminars, negotiated with VCs and spoke to thousands of customers along the way. It was exhilarating, exhausting and experiential. Looking back now it all kind of becomes a blur, except for the people. I made life long friends and others I’ll never see again.
Life is funny that way. People that are so important to you, at least you think so, and you see every day, are gone just as quickly as they arrived. Life is too short to spend time with those you don’t get along with, trying to make it work. But sometimes you don’t have a choice. And yet, you do, and it’s a tough choice. But when you get to the end, it’s an easy one.
When my last company wound down I wasn’t sure what I wanted to do. What a funny way to say shut the doors. I think people like safe, clinical words to remove the emotion. Closing a company is difficult and painful, even a small one, because you had such high hopes and dreams, and put so much time and effort into it.
Here I was 43, practically ancient in the tech world, having missed out on a big pay day, and yet had enough success in life that I had options. That’s not always a great thing because when you have options you’re afraid to make a choice, at least I was, and still am at times. But it’s better to have options than not.
In 20 years of working I had never worked for someone. I had always done my own thing and I thought it was time to go down that path. With my experience, skill and knowledge I figured I could quickly and easily find somewhere I could contribute to. Three months into conversations and interviews I quickly began to understand that things aren’t what I assumed.
My personal path was working against me, in that people wondered if I could work under someone else, if I could take orders, if I could follow someone else’s vision. And of course I had wondered these things myself. I’ve always enjoyed working with a team of smart, passionate people. When people say that a strong team is the most important thing to succeed, it’s not a cliche, it’s the truth.
If I found the right company, with the right vision, and the right people, I could happily join such a team. My goals now are different than they were. Fulfillment is not only something I want, it’s the most important thing.
Which brings me to today and to you. Recently I’ve been reading a lot, from business books, to self improvement books and to marketing and sales books. At the same time I’ve delved into podcasts and newsletters. What I keep coming back to is that I love politics, I love technology and I love to write. After a recent reading of James Altucher’s book, Choose Yourself, I decided to do just that and not wait.
I love technology, not the coding or the semiconductors, but rather the people behind them. These are passionate people who tend to dream big and want to change the world. On the other side I love the people who use technology, these early, fearless adopters who dream of a flat, interconnected, on demand world. You need these two types of people, otherwise the promise of technology will never come. It is these people’s stories that inspire me and I want to learn from and share with you.
With a daily newsletter, a blog and a weekly podcast, I hope you’ll join me as I explore this new, exciting path. I hope you enjoy reading and listening, because I know I will enjoy learning and creating. It wouldn’t be the same without you.