I’m Probably Not The Coach For You

Right around my 36th birthday, I became a millionaire.

It happened overnight, literally.

I don’t say this to boast. I say it to establish credibility.

I have been in it. I have made it. I know what it takes and how to get there.

I coach from a place of real experience and real success, measured in the currencies of our time. I don’t coach from a framework or repeat what other coaches say.

I coach from a place of endless curiosity, in a pursuit of helping others not just understand how much value they truly offer the world, but also what to do with that value.

I help professionals step outside their box through the simplest form of discovery of all time: conversation.

I ask questions. Lots of questions. And both quickly and over time it will help.

A lot of people wonder what it takes to reach your goals. It takes only two things:

  1. Simple and clear goal(s)

  2. Mindset

On paper, the story is quite simple: I was working at one of the world’s best companies, Linkedin; then, after 3 years I was recruited by one of the fastest growing enterprise software companies in history, UiPath, where I worked for 18 months and let go; one and half years after I was laid off, UiPath went public and I cashed in on the options and restricted stock units (RSUs) I vested in my 18 months and made millions.

I am white. I am a male. I was raised in an upper-middle class household in the New York Metro area (Northeastern NJ).

These things are not lost on me and I place them in the ‘luck’ bucket. I have no idea where else to put them. But my story is much more nuanced and, in some ways, surprising. To be it lightly, it wasn’t that simple.

But I do know how it worked

Here’s why I’m telling it to you below:

This is how I see the world.

I will risk it all for the pursuit of happiness because I believe in myself.

Here’s an abridged version:

  • made millions from uipath stock

  • was laid off from uipath

  • got a job at uipath - did ‘best in class’ work, performance got me more shares

  • Got recruited by UiPath - one of my teammates met a UiPather at a conference, and because of how she had seen me work; my performance; my reputation - she told them I was the only person they should speak with if they were serious

  • Finished as the top performer globally in my function, highest quota attainment (by far) and the largest deal ever closed of it’s kind

  • I was recruited/promoted from Mid Market segment to Key Accounts (by James) because of my performance, reputation, and fearlessness

  • I was a top performer and widely seen as a disrupter and visionary within my function - largely because of the inquisitive questions I would ask, my curiosity to know what drives excellence, and my bold ideas and willingness to try them (and fail)

  • I got the offer that would change the course of my life. That would bring me out of a hole I had dug for myself and into the front lines of the tech world. Through my network I got an interview with Linkedin. I made it my life’s purpose to the best and most prepared candidate they had ever seen. I got the job, and when my manager called her new team members to give a dry run sales pitch I was exempt because I ‘could just do what I did in my interview’.

When I was deciding on where to go to college, the choice became really simple: a good school that I’d really enjoy my time at. I was (extremely) fortunate to have parents that were prepared to pay for (every single aspect of private) school so I knew I had options. I had grown up in New Jersey so warm weather was particularly attractive. My guidance counselor had informed me that the University of Miami was going through a bit of reckoning and would be a great option for me. I prioritized my potential joy and joy is what I got.

I loved my time in Miami more than I can ever express in words.

I had never really considered a career.

It just never interested me for some reason. Before I knew it, however, graduation was upon me and while my friends all had jobs lined up at media or financial firms, I didn’t even have an interview.

I bombed all the on-campus interviews with JP Morgan and the like, but thought it was for the better.

I ended up with a job back home in New York, working ‘production’ (aka logistics) for a court reporting agency. It was more interesting than it sounded, paid very well, but also became as boring as it originally sounded. I left after about a year and learned that doing the same thing over and over again is just something I cannot do.

I was 23 at the time. I spent the next 5 years working random jobs to save some cash (including at my father’s bakery) and then spending that cash traveling around the world. I would run out of money and do it again.

Remember, I had never really considered a career.

But I was sure about was that these were my 20’s, and only had one chance at them, and something deep inside told me that I simply needed to see the world. And it told me that even though all my friends are off building their careers and relationships, that this decision, in the end, would serve me well.

Finally, at 27, I had no more money, no more ‘jobs’, and no resume or career to speak of. I tried some low level sales job, the ones that hire people without serious resumes, but none lasted more than a month.

It quickly dawned on me that I was ready to have a real career - albeit later than my peers - but had no chance at getting a real job to get it started. So I decided to go for my MBA, which I assumed would help level the playing field, even slightly, and grow my network.

I wasn’t going to get into a top school in the US, and it had been some time since my last big trip, so I had an idea: apply to an MBA program oversees.

I attended ESMT in Berlin, which was a brutal academic experience, but was equally balanced with incredible cultural experiences that include: summer vacation in the south of Italy (with Italian friends); a 3-week school project in rural India; Christmas and New Years in Kruger National Park and Cape Town, respectively (again, with local friends I met at school). The business and cultural perspective I gained, being only one of 5 other Americans in the class, was mind blowing.

I came home with a fever for tech entrepreneurship and a terrible idea for a startup that had no chance at succeeding. But something I had learned in business school was to lean into my ‘big thinking’, and a fire had sparked, and I wanted to ultra successful (aka ultra rich). I thought a startup was my best chance…and I was willing to live in my mom’s guest room while I tried.

That startup failed. So did the next two. Which made 3 in 3 years. It was time to move on and finally get a job in corporate America.

And now I had no idea what to do. I even started to panic.

I was 28, living at home with my mom, with no money and the only thing on my resume being inflated roles at my father’s company and an MBA from a German Business school no one had ever heard of.

But something started sink in. It started to percolate. It was right there in the back of my mind, slowly creeping to the front. It was in grasp but still unclear.

Then suddenly, it hit me.

I am different. And that’s what’s going to get me a great job.

I sat down and wrote a short autobiography to try to see myself through a hiring managers eyes.

One thing I realized was that I was pretty interesting! And I had some really hard skills and knowledge that I built up in various areas through this unusual journey of mine:

  1. I was the only one in my social circle that was tri-lingual (German is actually my first language, but hadn’t spoken in two decades. Living in Berlin sharpened this skill. I also spoke solid Spanish after a trip to Spain in high school, and a big backpacking trip in Central America made for great practice)

  2. I learned more about the internet and content/growth hacking than not just the average person, but the average marketer (the biggest takeaway from my failure as a startup founder was that you can learn anything on the internet for free. Like how to get traffic/customers with no budget - when you’re desperate, you look for answers and answers I got)

  3. I had global perspective that almost no one else at my age had (Among my travels included: 3 months working the graveyard shift in bakers in Germany, Austria, and Switzerland in the dead of winter (lots of snowboarding); A two-month long hike from the southern tip of Israel to the Northern tip (about 600 miles); 4 months backpacking through central America, including 2 months of teaching English; MBA in Berlin and the trips to Italy, India and South Africa I mentioned)

Here’s what I do now:

Here’s how it works:

Here’s who this is really for:

This is a real investment

What you get:

clarity, confidence, guidance, new ideas, a plan (with backup plans)

Unlimited meetings/time with me for 2 years