What is a game that's rigged in my favor?

Many lifetimes ago, I became immersed in the game of blackjack. I read all the books, online forums, studied the greats and practiced daily.

It was a wild ride that ultimately ended up with me being able to buy an apartment when I graduated college.

It was a game where I was able to eek out a tiny advantage. Math, statistics, probability, memory, socializing and the ability to handle my alcohol allowed me to grind out some wins and a whole lot of free comps which were a very welcomed upgrade over my normal college life.

The biggest takeaway from that time, aside from the emotional resiliency of being able to handle swings of 1000s of dollars in seconds, is to play a game that is rigged in my favor.

The easiest way to identify the games where I have the most advantage is to look at the unique combination of my gifts.

What is the intersection of things that I'm good at that many people are not?

• Entrepreneurship & problem solving
• Influence & business development
• Technology & product development
• Leadership

These 4 areas have been the focus of most of my adult life and have produced outsized results for me. The places where I can naturally excel are the roles that allow for some combination of these skills to shine. The more the merrier.

It's all too common to spend time playing a game we can't win, don't want to win or where we don't have any tangible advantage. If the goal is to out-produce our potential, then the starting point is to triple down on our unique combination of genius.

The games I'm playing these days are much different than the games I played as a know-it-all, "can't tell me nothing" college kid. But. They are still very much architected in a way that I'm more likely to win than lose.

Is it time to build?

On April 18, Marc Andreessen published a piece called "It's Time to Build." I've read it several times and consumed much of the praise and counterarguments that came along with it.

And now, I can definitively answer the question when I ask myself, "Is it time to build?"

Yes, it is absolutely time to build.

It's taken me 10 days to be fully certain because the answer comes with significant ramifications. Not something to be taken lightly.

During this time, I've utilized many forms of distractions to kick the can down the road and allow this decision to breathe. Some of those distractions have been productive like contributing to The $1k Project and Sponsor A Quarantine, deep cleaning the entire apartment and naps in the park. Others, not so productive, but it was all part of the process.

What are the ramificiations of deciding to build?

I'll answer that question with three more questions. Do I really want to start another company fully knowing the everyday rollercoasters that come along with that? And even more so, do I really want to start another company in the middle of a global pandemic? Is now really the time to be inviting more uncertainty into my life when we already have more uncertainty that anything we've ever experienced in my lifetime?

Again, the answer to all of them is yes. While starting a new company right now may seem insane or even masochistic, I truly believe that there has never been a better time to be an entrepreneur. The world has a whole new set of problems that didn't exist even a few weeks ago. And that's what entrepreneurs do, they solve problems.

One thing Marc wrote instantly jumped out to me. It's something I've been passionately talking about for the last few years.

"We need to get all the talent we can on the biggest problems we have, and on building the answers to those problems."

I've been calling this The Avengers Initiative for obvious reasons. Bring together the most talented people to solve the problems that bring humanity forward.

I've had a few false starts with getting this initiative off the ground, learned a megaton and have been secretly "recruiting" these amazing individuals for years. I certainly didn't know that we'd be in a situation quite like this, but I knew in every ounce of my being that there would be a time, many times throughout this lifetime, where we need the most talented people to build. It pains me that this initiative hasn't come together faster or that it isn't further along at this moment.

And yet, it's time to look forward and start building today.

Marc suggests that...

"Every step of the way, to everyone around us, we should be asking the question, what are you building?"

My answer to this question is something that I've been experimenting with behind the scenes based on what I learned teaching leadership around the world.

I believe that there is an opportunity to leverage technology to massively improve learning outcomes across the planet. Specifically, I believe the combination of a modern curriculum and experienced based learning can lead to a zero marginal cost education platform with radical improvements in student engagement and retention.

I will be writing more about this as the prototype for this product comes together in the next few weeks. If you interested in experimenting around how we build the future of education, let's jam.

And now we build.

Can I move the needle every day despite the chaos?

A few weeks ago, I gave some advice to a dear friend who is starting a similar and yet very different position to something I have previously done. This advice had nothing to do with the incoming pandemic, but it seems even more relevant for all of us today.

When she sent me a text last week to let me know that she's thinking about that advice every day, I realized that it was exactly what I needed to be thinking about myself each day. Funny how it always seem to work out that way.

Here's the question I shared with her:

"What is the most important thing that you can be focused on to move the needle for the business each day?"

Everything else is going to be a distraction.

In her position, it is likely she'll have several people in the organization asking for her help on different projects and assignments. She should be hyper diligent about where she is spending her time. If something isn't tangibly moving the needle forward, it should be delegated, deferred or flat out rejected.

And here I am. Being consumed by the COVID19 news cycle. Trying my best to help my family and friends stay safe and make smart decisions. Doing what I can to boost my immune system while being locked down in "shelter in place" mode for the foreseeable future. And that advice just hit me square in the face.

I will be asking myself each morning: "What is the most important thing that I can be focused on to move the needle for the business each day?"

While moving the business forward is only part of the bigger overall picture right now, I still want my work time to be as laser focused as possible. Now more than ever.

How can I be wrong more?

As I was re-designing this personal website and getting back into writing, I had a choice to make. What should I do with all the old posts that I have written?

There was a loud voice in my head that voted to get rid of it all. Start fresh. Keep it simple and clean. No need to keep that old content around anymore.

While all of those reasons are valid, it was masking the real reason behind that thought. Some of those old posts are bad, poorly written and completely wrong.

I wrote about the future quite frequently, so it's easy to look back now at how wrong so much of that was. Some of it was only slightly wrong and some of it was completely and comprehensively wrong.

Ultimately, I decided to keep it all there, keep it public and searchable.

I want to be wrong more.

Having that archive public is a good reminder of that. While some of those posts were wildly inaccurate, others were tangentially correct. Some of my Free Startups Ideas turned into companies and raised capital. Some of my analysis and predictions were close to correct. None of that is important though.

The process of taking the time to think through possible futures, digest those thoughts and write it all out in a coherent manner makes me better. It helps me be a better leader and entrepreneur. I want to make sure I'm doing more of that, so I'm happy to keep being wrong as frequently and publicly as possible.

Where do I begin?

With today being the first day of a new decade, it felt appropriate to write about some of the feelings that come up at the beginnings.

I have started more companies in my life than I ever imagined. I've spent time on additional products that I never even made it to the official company stage of life. And I'm right in the middle of starting something again.

And almost always there's been this question of "where do I even begin?"

There's so much to build, read, write, create, explore, learn, grow, and do that it can feel overwhelming. I've found this simple formula that has served me well, and I'm writing about it now as a reminder.

In solving any complex problem or building anything signficant, I've found it's best to look for the building blocks to unlock the next level.

Break down the situation into the significant and major accomplishments that make the rest of the game easier. Level up each step of the way to accomplish bigger and better things.

Here's a quick real life example of this.

When we started NY Tech Day, neither myself nor my partner had any connections in the NYC tech community. We didn't have an audience to jump start this. We were literally started from scratch with a powerful idea and a lot of skeptics.

I knew to hit the massive numbers we were promoting and expecting, we needed to up level quickly. I started by getting two prominent startups to agree to attend as featured startups. It took a list of 50 dream startups to get there: 48 no's to get to 2 yes's. With those two on board, we were able to get some initial press. Now with 2 featured startups and a few press articles, we were able to attract investor interest. Then the attendees started flowing. Then the sponsorship sales became easier. And finally the rest of the startups jumped on board. None of that could have been done without executing at each level of the game. Building blocks.

All told, we ended up with 200 startup exhibitors, 4000 attendees and over 10 high dollar sponsors for a first year event in a brand new market.

As I sit here at the beginning of this new year and with this new venture contemplating where to start, I'm reminded of the simple and powerful answer.

Start on Day 1. Level 1. Figure out the skills required to complete this level and move on to the next.