The Difference Between Winning and Losing

When I was in 4th or 5th grade, I went on a summer hiking trip up in the Adirondack mountains.  It was a three-day trip with about 15 kids.  At night we camped out in tents along the trail.

Overall, I recall the experience fondly and the trip started off great.

The first day was bright and sunny.  I was one of more the more athletic kids, so along with a few others, I set a pretty aggressive pace for the hike.  We were way out front ahead of the pack.  I remember what it felt like to be out front – it felt good.  It felt like we were winning.  We could stop to explore different areas at will, we could leisurely enjoy views of the mountains, we were in complete control.

Day two was a bit different.


A-B-D: Always Be Demoing

Back in 2015, I was introduced to Jonah Goodhart, CEO of MOAT.  Jonah is a well-known ad-tech leader with many exits to his name (you can read more about Jonah here) but, at the time, I knew him primarily as an early investor and board member of Right Media.

Jonah is a nice guy and even today (three years later) I remember having a positive conversation with him.  However, what really stuck in my head is what happened after we finished the stated agenda of our call.  Jonah said (more or less) – “while I have you on the phone, let me show you our product” – in an instant, before I could even ask why, he had a screen share up with about 20 pre-loaded browser tabs open.  He then launched into a comprehensive product demo covering every aspect of the MOAT viewability product.  The demo was flawless – like he had practiced it a thousand times.

I remember walking away from the call a little puzzled.  Why did Jonah Goodhart just spend an extra 20 mins on the phone with me to deliver a product demo?

Two years later (in 2017) MOAT is purchased by Oracle for $850M.  Thinking back to my call with Jonah I now understand why he stayed on the phone with me.  It wasn’t because a demo was part of our phone call – it was because a demo was part of every conversation he had. (more…)

The Two Under Two Club

With full hearts we welcomed our second son Graham into the world this past week.  He’s doing beautifully, as is his mother, and his older brother Jack is handling the transition with class.

When we came home from the hospital mid-week we realized that we are now in the prestigious “two under two” club, meaning we have two children under two years old.

Prior to having Graham, I talked to a lot of friends about what to expect as the parent of two children and many of them used the same analogy to describe it.  “It’s like ‘one on one’ defense”.  Most of them joked that going from two children to three children was the real challenge “then you had to switch to ‘zone defense’”.

Levity aside, as someone who played men’s lacrosse for most of my youth, it feels a lot more like ‘man down’ defense.  The only time when ‘one on one’ dynamics are really possible is when both parents are directing 100% of their attention toward caretaking.  If either parent wants to do anything independently (or god forbid use the bathroom or take a shower) it puts the household into an immediate shorthanded formation where one parent is covering two children.

We’re only one week in, but so far so good.  I think the best part so far has been watching the two boys interact.   Watching two children that you created interact is really quite magical.

A Lesson in the Power of Price Perception – Courtesy of Build-A-Bear Workshop

Last Thursday, Build-A-Bear workshop announced that they would allow customers to “pay their age” for their products.  For those not familiar, Build-A-Bear workshop sells customizable teddy bears and other stuffed animals for – after customizations – roughly $50-$60, so it’s no wonder that the “pay your age” event garnered a lot of interest.  Around the country parents of young children salivated over the opportunity to get their youngsters a new stuffed pal at a steeply discounted price.

At this point, we all know it was a disaster.  So many people showed up for the event, they had to shut it down only a few hours in.

Hindsight being 20/20, we now know that this was a terrible idea for a variety of obvious reasons:

  • The promotion was announced only three days ahead of time, so there was limited time for everyone to prepare or gauge interest
  • The Build-A-Bear product takes a pretty long time to make, so any sort of significant price promotion was likely to overwhelm store capacity
  • They incentivized parents of the youngest children to come (the younger the child, the bigger the discount) – and as a parent of a young child I can tell you they aren’t great at waiting in line for a long time
  • And of course – an unfulfilled promise of a new stuffed animal to a young child is a pretty serious problem for a parent.

But those issues aside, here’s what I found so compelling about this business gaffe:

The promotion was billed as “pay your age” – which successfully lodged in the minds of their customers that they would be able to get a fully customized furry companion for their three-year-old child for just $3.

However, that wasn’t actually the deal. (more…)

Hey – Do you want to invest in Bitcoin?

I got the text around the start of the year.  Some of you have gotten the same text.  Mine came from an old friend who works in the financial industry – but he was far from the only person asking this question:

“Hey – do you want to invest in Bitcoin?”

Going back over a year I had heard about blockchain – particularly the applications to the digital advertising industry (where I work), but I had never seriously considered investing in any crypto currencies.  Also – I wasn’t really sure I understood what a BitCoin was or why it was so valuable – so I took some time, talked to a few people, and really tried to understand what was going on under the covers.

After a few days of research, I could confidently say I think I understood it.

I work in tech… and after a few days I got to “I think I get it”.

However, the more I learned about Bitcoin the more skeptical I became about it’s prospects and all crypto currencies.  I also learned that the first text I got: “do you want to invest in Bitcoin?” was actually critical piece of what makes bitcoins so valuable.


Talking About Politics and Online Trolls

If you ask most people, they will say that religion and politics are the two things you should never talk about with family or business associates.  Those two topics are just too divisive – it’s too risky to even talk about them.

Is this really a good cultural norm?  Not being able to discuss things with people close to us?

It’s true that these issues are divisive, but doesn’t that mean it’s more important to discuss them with people we care about so we can all progress our thinking?

No wonder we’re so vulnerable to online political trolls influencing our thinking and polarizing our country – if we have no practice dealing with these conversations in real life, how are we supposed to deal with them online?


Creating True Long-Term Value

How many different ways are there to create true long-term value?

It’s difficult to even think of how to answer such a question.

Hmm.. let’s see, there are lots of different industries to start, so that makes the problem pretty broad.  Also, there are lots of different methods to improving a business: you can optimize a current business model, you can disrupt a value chain with a new business model, you can just work harder, you can work smarter, etc. etc.

I was thinking about this question over the weekend when an episode of Shark Tank came on the TV.

“Perfect!” I thought.  Here’s a great case study.  The entire premise of Shark Tank is that the “sharks” are gifted business people who create long term value.

However, is that true?

Let’s take a look at Mark Cuban (he just happened to be the one I picked on).  He’s written books, he owns a basketball team, and is overall portrayed as a gifted businessman.  Surely he’s someone who has mastered the art of creating long term value, right?

But how did Mark make his money?  Let’s take a closer look.


Dopamine and How our Brains Look for Patterns

This past weekend I listened to a really fascinating episode of the Radiolab podcast about stochasticity (which is a fancy word for randomness) and finding patterns.  One part of the episode explored the story of Ann Klinestiver, a teacher who was diagnosed with Parkinson’s disease and later become a gambling addict.  Evidently, it’s very common for people with Parkinson’s to develop a gambling addiction.

When I first heard this, it sounded preposterous.  Why would Parkinson’s disease have anything to do with gambling addiction?

Before this makes any sense, first we need to think about how dopamine works.

My understanding of the brain is pretty primitive – but according to the podcast, dopamine plays two key roles in the brain:

  • Role 1) “Pleasure” or reward indicator. Your brain releases dopamine when you’re doing something that feels good or is enjoyable.
  • Role 2) Movement and motor skills. Your brain uses dopamine as a key component of making your body move.

Parkinson’s is a disease where the part of your brain that uses dopamine to move (Role 2 above) starts to die.  That’s why Parkinson’s patients tend to have trouble with movement.

To treat Parkinson’s, patients take synthetic dopamine drugs to help with their movement (that’s where the shaking comes from – too much dopamine makes it hard to stop moving).

So – what does all this have to do with gambling addiction?

That’s where dopamine “Role 1” comes in.


On Being a Draftsperson

I’ve always enjoyed working with my hands, and in college I took classes in jewelry and metals.  I was taught by a Professor named David Peterson who is an extremely talented (albeit tough) teacher.  After studying with David for two or three semesters, I realized that I had never seen anything that he himself created, so one day a few students and I convinced him to bring some of his work to class.  He brought in one piece – it was a salt and pepper shaker (I found a picture here in David’s now-online portfolio).  I still remember when I saw it for the first time, it was one of the most creative, interesting, and impressive works of art I’ve ever seen.

After he showed us the piece, he took out a very large piece of blueprint paper and showed us his draft drawings.  Holy moly – his drawings were so detailed and intricate that they themselves were a work of art.  He had completed detailed scale drawings of every single component of the piece in immaculate detail.

When I saw the drawings, I couldn’t help but thinking how much time the drawings must have taken.  Hours, days probably.  At the naïve age of 20, looking at those drawings, I remember having only one thought:

“What a waste of time!”

In college, when I worked in jewelry, I never spent a long time planning.  I would get a general idea, maybe do a quick sketch in a small sketch book, then just sit down at the bench and start sawing and soldering until I got results that I was happy with.

“Dive right in”

It was the method that I used for a lot of projects in a lot of areas.

Looking back – I now understand why David spent so much time drawing out his creations.  But the lesson took me a very long time to learn.  Here’s why: I often got good results by just diving in!


Follow up on Taxes and Distrust for the Government

It’s been about a month since the article about my family appeared in the New York Times and a lot of folks have been reaching out to ask if we ended up pre-paying our taxes.  The answer is yes!  But, it’s a pretty disappointing “yes”.

Let me explain.

After Governor Cuomo signed the emergency order on December 22nd that would allow New York residents to pre-pay 2018 property taxes in 2017, (and after the article about my family was published in the Times) the IRS made their own announcement (on December 27th) stating that pre-paid property taxes could only be counted as a 2017 income deduction if the taxes were assessed in 2017.

The IRS announcement really blew me away.

Thousands (if not tens of thousands) of people had already pre-paid their 2018 property taxes in full between the time Cuomo made his announcement on the 22nd and the IRS’ announcement on the 27th.  Those poor folks ponied up big bucks thinking they were going to save some money, then the IRS changed the rules on them with only three days left in the year – truly crazy.

Luckily, we did not pre-pay our 2018 taxes prior to the IRS announcement – we were planning to, just were unable to submit the payment due to holiday travel.  What isn’t so lucky is that the vast majority of the $21,000 we pay in property taxes goes to the local school district, and the school budget isn’t finalized until Q2 2018.  The amount of our total 2018 tax bill that we were eligible to pre-pay was actually quite small – just $260.00 out of our overall $21,000 bill (just over 1%).  As it turns out, in Westchester it’s very hard to assess taxes on short notice, it usually takes a few months.  The only people who were able to scramble together and assess taxes in the last week of December were the local town firefighters – who were the recipients of our $260 pre-payment.

Our expected total tax savings from our pre-payment?  Probably around $50.