Inside My Brain

Thoughts about startups, tech, marketing, and life


Process > Results

I recently listened to the book titled Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by poker champion Annie Duke

Being a poker player, I was naturally compelled to read this book. And being an entrepreneur, I totally understand the difficulty of making decisions with little information. And Thinking in Bets crystallized this concept really well. 

The premise of the story is that in poker (and life) you have to make decisions with imperfect or very little information, and due to luck, the right decision may result in a negative outcome. 

For instance, before the flop comes, pocket Aces is the best hand in poker. So it’s always the right decision to raise pre-flop. But against another pocket pair, there is an 18% chance you will lose. So if your Aces get beat by another pocket pair, were you wrong for playing your Aces the way you did? 

On the flip side, you can make a terrible decision and play your hand like crap, and still win.

Here’s another example. In Super Bowl XLIX, the Seattle Seahawks had a 2nd down at the New England Patriots’ 1-yard line with 26 seconds left on the clock and a chance to win the game. They had one of the best goal-line running backs in Marshawn Lynch. But head coach Pete Carroll decided to call a pass play, and Seattle QB Russell Wilson threw an interception to end the game 

Many have called this the worst decision in football history. 

But what if Russell Wilson threw a touchdown? What would people have thought about Carroll’s decision? They would have likely said that it was “gutsy”, “brave”, and “fearless”.

In reality, the decision actually made sense, primarily due to clock management and the defensive formation the Patriots ran. I won’t get into it here, but you can check out this Slate article and this SBNation article for more info. 

We all make decisions with imperfect information.

Maybe it’s a decision to hire someone for your team at work, and that person doesn’t perform as expected. 

Maybe you decide to buy a new house in a great neighborhood, but a black swan event happens and the house’s value goes under water. 

In both cases, you could have done all of your research correctly, checked off all of the boxes, dotted your T’s and crossed your I’s. But sometimes things happen that you have no control over. 

If this happens, do you doubt your decision-making abilities? Do you not trust your process anymore? 

Certainly, you should try to find the holes in your thought process. Did you not see something you should have seen? Did you not do enough research? 

But if you’re confident you did all you can do, you shouldn’t doubt yourself just because the outcome wasn’t positive. 

If the outcome turned out the way you expected, I’d bet that you would think you’re a genius, right? Right. 

So the point of this all is to separate the outcome from the process. Whether you were right or wrong, you can’t let the result of your decision cast doubt on the work you did to get there. 

I think this is a really important mindset to have. Process over results!

Have you been in any situations where you thought you made a correct decision that turned out negatively? I’d love to hear your thoughts!

In poker, business, and life, there’s only one real way to learn – by doing


I took the last two weeks off from blogging because I was traveling for Thanksgiving to NY/NJ and the Amazon Web Services re:Invent conference in Vegas. I hope you didn’t miss me too much.

Anyway, while in Vegas, I of course had to hit up the poker table. Many times.

During one late night/early morning session, a pretty young guy (let’s call him Chad, I don’t remember his real name) who was also there for the conference sat down next to me. Nice guy, pretty chatty, and probably had a few drinks in him, like everyone else at the table.

He sat down with $100 and lost it within 20 minutes.

He whipped out another $100 and lost that within another 15 minutes, most of it to me on one hand.

He took out another $100. At this point, the guy sitting on the other side of him and I started helping Chad out a little. We told him how it was OK to fold once in a while (he essentially played every hand), the importance of position, and other poker fundamentals.

Regardless, he lost that last $100 pretty quickly.

When he left the table, I looked around and said “I guess there’s only one way to learn,” and everyone had a good laugh.

You can read all the poker books in the world and watch the World Poker Tour on TV, but once you step into that casino and sit down at the poker table, everything changes. And the only way to learn is to play a lot of real hands and probably lose some money.

You can read all the books and blog posts about how to build a company, recruit a team, develop a product, and more, but until you actually start putting in real work, you won’t learn how to do all that.

You can prepare yourself for raising that baby, but childcare books won’t ever prepare you enough for changing that first shitty diaper or dealing with a 2-year old’s temper tantrum.

The only real way to learn anything is to do it.

I’m not sure if Chad will learn from his experience in Vegas. After all, it was late, he was probably drunk, and it’s Vegas, so who really cares about losing a little money, right?

Regardless, the lesson is that there’s no better way to learn than by actually doing.

You’ll never be able to replicate situations at the poker table, in business, or life. The only way to learn is having the direct experience of doing.

So what will you do today to learn?

Lessons learned from Isaiah Thomas’ letter to Boston after being traded

Bradley Beal, Isaiah Thomas

Even if you’re not an NBA or sports fan, I think this story is something you’ll appreciate.

Isaiah Thomas is the former point guard for the Boston Celtics and was recently traded to the Cleveland Cavaliers. He recently penned a heartfelt letter on The Players’ Tribune telling how it all went down, how devastated he was, and how much his time in Boston meant to him. It’s an amazing read, so take 5 minutes and read it now – I’ll still be here when you get back.

Isaiah was the last player drafted – the 60th player overall – in 2011. Players drafted in this position rarely last in the NBA, and if they do, they’re typically relegated to the bench and traded many times.

Isaiah is 5’9″, tiny by NBA standards.

After stints in Sacramento and Phoenix, Isaiah was traded to Boston, where he became an All-Star and MVP candidate and led the team to the first seed in the Eastern Conference last season.

His sister Chyna tragically died in a car crash during last season’s playoffs. He flew to the West Coast to attend her funeral, then flew back to Boston to play the next night. And he scored 33 points and logged 9 assists.

Isaiah played months through a nagging hip injury that forced him out of the playoffs. He left his heart and soul on the court every day.

Yet he still got traded.

The guy he was traded for is Kyrie Irving, who is essentially basketball royalty.

He was drafted #1 overall that same year Isaiah was drafted. He played his college ball at Duke. Playing along side LeBron James, he’s been to the NBA Finals three years in a row and won the championship two seasons ago. Yet he wasn’t happy and demanded a trade.

While supremely talented, he’s been criticized as sometimes being lazy, playing bad defense, or being a ball hog.

Sounds like quite the opposite of Isaiah, no?

There are a few lessons that I took away from this situation and reading the article.

It doesn’t matter what deficiencies you have or what others think of you. If you work hard and keep learning and grinding, you can succeed no matter what hurdles are in your way. 

All odds were against Isaiah lasting in the NBA. Yet he continued to work hard and improve his craft, so much that he became one of the top players in the league.

Things can change at a moment’s notice. 

For better or worse.

Take nothing for granted. You can do everything right but bad things can still happen. Stay humble and just keep working.

Be appreciative.

I’m sure Isaiah was angry, and he could have lashed out against the organization and city that he’s leaving. But he expressed his appreciation and love. That’s class.

Ambition is a powerful thing.

It seems as though Kyrie Irving’s situation was amazing. He’s won an NBA championship and has perennially made the NBA finals. Yet he still wasn’t satisfied with this.

I’ve written about the difference between happiness vs. satisfaction a couple times in the past – see here and here. Kyrie’s ambition to “be the man” and play second fiddle to Lebron James led him to request a trade. Was he appreciative of this situation in Cleveland? Maybe. But was he satisfied? Nope.

On the other hand, Isaiah’s ambition to be a great player, despite his deficiencies, got him to where he is today.

Isaiah’s blog post is one of the most personal, heartfelt articles I’ve read in a long time. The guy has worked so hard and laid it on the line every night, yet he still got done wrong. Life’s a cruel thing sometimes.

All you can do is appreciate what you have and keep moving on.

Photo courtesy of Keith Allison on Flickr

How business is like poker

Business can be a lot like poker sometimes.

Many people take the wrong approach to poker and gambling.

When gamblers are losing money, they will keep playing to try to win back their losses. I see poker players spend hours at the table, lose stacks and stacks of money, and have no idea why.

And when people are winning, they’ll “quit while they’re ahead.” They’ll win a little bit and be satisfied with having a few more dollars in their pocket.

I think that’s totally backwards. Maybe we can call it the “gambler’s paradox.”

When you’re down, you should get up from the table, take a break, and gather your thoughts to understand why you’re losing. Maybe even call it a day.

And when you’re up, either your luck is running hot or you’re doing something right, or both. So you should ride that wave as long as you can.

You tend to see this in business as well.

When things aren’t working in business, you may see people stick to the same strategy, pump more money into advertising, and use brute force in an attempt to make things better.

Instead, they should take a step back, analyze where things are going wrong, and adjust accordingly.

When business is going well, many companies rest on their laurels, slow down, and stop innovating.

This allows more nimble and innovative startups to enter and win markets.

When things are bad, take some time off to refresh and rethink.

When things are good, put the pedal to the metal and keep moving fast and innovating.

Don’t fall prey to the gambler’s (or business’) paradox.

What do you think about this paradox? I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at

I hope you found this interesting! If so, please share this article with the share buttons on the left. Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at!

How Nike lost Steph Curry – and why the little things matter

Stephen Curry

I read this amazing article on ESPN about how Nike lost Steph Curry to Under Armour. It’s long, so read it after you read this post. 🙂

Basically, Nike f’d up during their pitch to renew Steph’s deal in 2013. Nike was the incumbent and had every advantage in signing him again.

Yet they didn’t value him and it showed in their pitch.

They didn’t send their top people to the meeting.

Someone mispronounced his name as “Steph-on” and didn’t correct himself.

There was a slide in the presentation that mistakenly referred to Kevin Durant instead of Curry, which showed that the slide deck was repurposed and not reviewed.

Because of these mistakes, Nike lost Steph to Under Armour, a mere upstart in the basketball world. And now Steph is the star of the NBA and Nike is kicking themselves.

It goes to show that attention to detail and how you do the little things loom large.

Back in 2013, Steph may not have been as popular or as important to Nike as Kyrie Irving or Anthony Davis.

But that doesn’t give them the excuse of not being prepared.

They could have pronounced his name correctly.

They could have reviewed that slide deck one more time to check for mistakes.

Nike essentially disrespected Steph by not paying attention to detail.

You can’t give every task an equal amount of attention; more important tasks have to take priority over less important ones.

But you should pay attention to detail, no matter how small that detail is. You should be prepared.

Know how to pronounce your customer’s name; if you make a mistake, correct it.

Double check that presentation for errors.

How you do the little things is how you will do the big things, so make sure the little things are taken care of, because they really matter. Nike found this out the hard way.

What are your thoughts on the importance of the little things? I’d love to hear from you. Write your thoughts in the comments, tweet at me @mikewchan, or email me at

I hope you found this interesting! If so, please share this article with the share buttons on the left. Then sign up for my email list below and connect with me on Twitter for future updates. And check out my podcast at!

This is day 40 of my experiment to blog for 30 consecutive days.

Image courtesy of Wikimedia Commons

Your value is what the market will bear

A few days ago I penned a piece titled “What’s the right way to assess value?

After yesterday, I now know that value is determined by supply and demand, and how much the market will bear.

Yesterday was the first day of free agency for the NFL, and money was thrown around like there’s no tomorrow.

Brock Osweiler, the former backup quarterback of the Denver Broncos, signed a 4-year, $72 million dollar contract ($37 million guaranteed) with the Houston Texans.

Osweiler has started only 7 games in his career, all last season. 7 games! How can you assess a QB’s value after only 7 games?

He was able to land this contract because all of the QBs available in free agency aren’t very good, and the prospects coming out of college aren’t great, either. And every team needs a good QB.

The Texans determined that his value is that high, even though they had very little data to work with.

Low supply, high demand.

The same is happening with “normal” careers like yours and mine.

In the tech world, software developers are commanding huge salaries because good ones are hard to find and hold on to.

Low supply, high demand.

In my past career in the sports business industry, it’s quite the opposite.

Because so many people want to work for a sports team or league, these entities can pay much lower salaries. And there aren’t that many of these jobs available.

After graduating with my MBA, I landed a marketing job with a professional sports team and my salary was about half of what I made as a management consultant prior to business school.

High supply, low demand.

It may be tough to deal with the fact that your body of work, while somewhat important, is overshadowed by things out of your control, like market conditions.

All you can do is work hard, be nice, get things done, and control what you can control.

This is day 25 of my experiment to blog for 30 consecutive days.

Guest Post for Thorn Technologies – The Week in Tech: Facebook at Work, Snapcash, Uber’s evil thoughts, and more

FB at work

Check out my new guest blog post on titled “The Week in Tech: Facebook at Work, Snapcash, Uber’s evil thoughts, and more.

Today we cover Facebook at Work, Snapchat’s partnership with Square, Uber’s hatred of journalists, NYC’s hotspot network, and what Apple wants to do with Beats Music. Enjoy!

I hope you found this interesting! If so, please connect with me on TwitterGoogle+, and LinkedIn for future updates.

Photo courtesy of GCAI Online.

Philly Half Marathon ran, $4605 for American Cancer Society raised

2014 Philadelphia Rock n Roll Half Marathon

In July, I launched my fundraising campaign where I would run a half marathon and raise $1,500 for the American Cancer Society because I really, really, really hate cancer.

On Sunday, I completed the Rock ‘n’ Roll Philadelphia Half Marathon along with 22,000 fellow runners (that’s me in the front right of the picture – just kidding). I felt really good doing it, not only because the race wasn’t as painful as I thought it would be, but because I was running for my father, uncle, best friend and everyone else who has been negatively impacted by cancer. And I was able to raise $4,605 $4,675 dollars from my awesome family and friends to donate to the ACS!

It feels really good to do my part, as small as it may be, and hopefully this disease will eventually be eradicated. I believe that donations are still being accepted, so if you’d like, you can donate here.

Thanks to everyone who donated to the cause and supported me!

Tough Mudder, No Drinking, and Other Updates on My New Year’s Resolutions

At the beginning of 2013, I wrote a blog post that laid out my New Year’s resolutions, which were:

  1. I’m going to run at least two Tough Mudders, Spartan Races, or other similar races.
  2. At some point this year, I’m going to not have an alcoholic beverage for 14 days.
  3. I’ll achieve more focus in my entrepreneurial endeavors.

A couple of these have been or are being addressed recently, so here’s a quick update on my progress.

Tough Mudder #1 Complete

Mudder 2013 Before and After

Three buddies, my brother-in-law, and I ran the Tough Mudder this past weekend at Raceway Park in Englishtown, NJ, and it was awesome. Everyone made it to the finish line (we thought one of the guys might croak) in disgusting, muddy fashion and earned our t-shirt, headband, and free beer.

I ran a Tough Mudder last September so I knew what to expect this time around; couple that with beautiful weather (it was pouring rain during last year’s race), and this race wasn’t as terrible. It was definitely still a tough mental and physical challenge, and getting electrocuted and jumping into freezing water still really sucks.

I need to fit in one more adventure challenge by the end of the year to fulfill this resolution, and am thinking about doing a GoRuck event. We’ll see!

No Drinking for the Next Two Weeks

Starting yesterday, I’m staying away from alcohol for 14 days.

I know this one seems really easy, but I love having a beer with dinner or just to relax, and I don’t think I’ve ever gone more than a week without having a drink.

After the two weeks is up, I’m going to reward myself with drinks at the Drake concert on October 31 and then my buddy’s bachelor party in Vegas that weekend. I think that’s a fair deal!

More Focus in My Entrepreneurial Endeavors

This one is a bit more subjective and fluid, and I’m probably breaking even right now.

I’ve taken on a co-organizer role with Startup Weekend DC, adding responsibility to my plate.  But I’ve been more focused on a couple of my consulting clients and have made some progress on my next startup (more on that in another post). I think I’ll focus more as we continue with the startup, but for now I think I have a good balance.

At this point, all of my resolutions can still be accomplished. But we’ll see where I stand in a couple of months!

New Consulting Engagement – Block Six Analytics

Block Six Analytics Logo

It’s always been a dream of mine to work for an intern that I hired in the past…and now that dream has come true! I’m happy to announce that I’ll be helping out Block Six Analytics (B6A), a startup founded by fellow NYU Stern alum and ex-Marketing Intern of the Washington Capitals Adam Grossman, as a Sales Consultant. You can read the B6A blog post announcing our partnership here.

I hired Adam as a Marketing Intern in the summer of 2009 (how the tables have turned). One of the projects he worked on was valuation of the Capitals’ sponsorship assets, and B6A was founded shortly after that on the same premise. B6A’s software helps sports organizations clearly communicate the value of sponsorships by using a valuation model that demonstrates how targeted impressions generate new revenue for their partners. I’ll leverage my network to help Adam market and sell this software, among other software and services, to sports teams.

I’m looking forward to working with Adam again and helping him build his company!