How to Make, Track, and Keep New Years Resolutions

I spent the majority of my childhood in a gym playing basketball. I loved it. It’s the only thing I ever wanted to do. 

I would dread January 1st each year, as my beloved sanctuary transformed into a mob of Resolution’ers doing their best Along Came Polly impressions. Raindance! Luckily, that group would start to thin out in late-January. All was back to normal by Valentines Day. 

For most people, resolutions don’t last. Here’s my advice on making them sticky: 

How to Measure and Identify Resolutions (Problems).  

Setting concrete goals is always a popular resolution route. Goals certainly feel more actionable than broad statements like “I’m going to learn to code.” 

Let’s take “I’m going to weigh <fill in weight> pounds in 2014!” as an example.

Goals like this do two things. First, they make you feel inadequate until you reach them. That’s no way to live. Second, if you do reach them… then what? You either set a new, lower goal, or fight and claw to stay at that “perfect” weight. Again, no way to live. 

The key with resolutions, as with startups, is choosing the right problem to solve. Then, identify the metrics/inputs you’ll need to track/improve to solve the problem. A specific weight is a vanity metric unless you’re a boxer. It’s like a startup where the goal is 200,000 users. Ok… what will that get you? 

Understand the problem you’re solving. Do you want to lose weight to be healthier and have more energy? Look better in a swimsuit? Attract the opposite sex? Throw the Five Whys at your resolution to get to the underlying problem, then determine the trackable inputs that’ll solve it. 

How I Track Things. 

I started tracking my diet about a year ago. I’d noticed I felt healthier, was more productive, and slept better when I ate well. I hated putting detailed food info into nutrition apps, and I have no interest in calorie counting - more vanity metrics. I made my own simple input system in excel. 

For each meal, I’d record a score of 0.0, 0.5, or 1.0, depending on whether my meal was unhealthy, moderate, or healthy. I color coded these to make them more visual. Sometimes I’d write exactly what I ate, sometimes I’d just write “crap.” The only important thing was the color/number. About 4 months in, I started tracking exercise as well. 

I set weekly and monthly goals, and my habits changed drastically. I eat far, far better now than I did back then. I take pride in my green 1’s, and try to limit or eliminate my all red days. 

Here’s my September: 


When I set goals, I try to make them trackable on a daily, weekly, and monthly basis using the system above. If I can’t, they won’t happen.

On To The Resolutions:

1) Control My Days. 

Problem: I procrastinate and waste time.

Solution: On Sunday of each week, I’ll pick the two most important, pressing things I need to get done the following week. I’ll section off time throughout the week to make sure they get done. Nothing interrupts that time, nothing is more important. 

Tracking: I’ll list these in excel on a weekly basis. They’ll get scored just like diet / exercise. This isn’t saying that every task can be done in a week - those that aren’t will be broken down - just that my most important tasks need to dictate my workflow. 

2) Control My Decisions. 

Problem: I don’t make decisions as quickly as I should. 

Solution: Identify the two most important decisions I need to make each week - the ones that keep me up at night and distract my mind,

Tracking: List them in excel, and make a decision on them by the end of the week. Delete them after the decision is made. Deal with the decisions after they’re made. If I make the wrong decision, fine, I’ll deal with the ramifications sooner rather than later. 

3) Make Something Every Time I’m Bored.

Problem: The creative bone atrophies when it isn’t used, but gets exponentially better when it is. When I’m bored, I have a tendency to give into the boredom and watch things like White Collar. 

Solution: When I’m bored, I’ll make something instead. This could mean writing a blog or a skit for SNL (still my dream job), outlining a newsletter for FYL, sending a funny email to my friends or calling my mom (“making” her happy). I hate being bored, but I let it happen anyway. Building a trigger to combat it should help. 

Tracking: Every time I give into the boredom, I’ll note it in Excel. Every time I avoid the boredom, whatever I make will be better than a green 1 anyway, so no need to track it. 

I’ll see how these go. They’re all easy to implement and should have a positive impact on my life. 

Friends and Family Funding and Why I’m Dreading Thanksgiving

I love meeting with students after my GA Class. It’s one of the main reasons I teach the thing.

However, a troubling trend is emerging among the “I’ve got a job and want to start something on the side” crew. A reliance/dependence on friends and family funding to test hypotheses. Worst of all, there’s an air of nonchalance around the whole thing. 

I’ve heard over and over that people have “a few family members who are good for $15-20k each,” and that by taking this money they’ll be able to “hire some devs and see if this thing has legs.” I’ve even heard variations of “I’ll give it 6 months, and if it doesn’t work, no harm no foul.” 


Charlie O’Donnell wrote a blog about easy money and tough questions. If you’re raising friends and family money, you probably won’t get many tough questions. Maybe they’ll ask about financial projections or competitors, but they’re likely not in a position to pound you on product/market fit, customer acquisition, key metrics, hires, etc. They’ll invest because they like you and think you’re smart. 

Not all likable, smart people can start companies. 

I’m dreading Thanksgiving this year because I took money from family members who liked me and thought I was smart. I’m deep into my second pivot, and haven’t yet delivered an exit two years after that initial money. I’m confident I will - I bust my ass every day - but I haven’t yet. 

They don’t blame me at all. They’re just as loving and supportive as they ever were. But it’s different. Maybe it’s all in my mind, but that’s still different.

Thanksgiving becomes Thanksgiving plus a 20 minute board meeting. That sucks. All I want to do is mess around, make jokes, catch up, play some football, and overeat.

Instead, I’ll talk about our (awesome) new CTO, discuss traction and why the thing isn’t out when we said it will be, then demo a buggy product at the dinner table. 

I’m incredibly, INCREDIBLY, grateful for them taking a risk on me. I’m confident in myself and my product.  

But I’m not sure I’d do it again. I wish I’d hustled a bit more and kept my family out of it, and think new entrepreneurs should try to do the same. 

Quick Thoughts on Coin and the Pending Crowdfunding Backlash

In a 48-hour period I saw Coin pop up hundreds of times - from emails to social feeds to in-person conversations.

They NAILED their demo/launch. Interesting idea with “wow” moment, great product video, social triggers/feedback loop (“I just bought my Coin!” was basically trending on Twitter), solving a real problem, etc. None of that is really interesting to write about because it was basically flawless. 

So, here are my other takeaways/feelings on Coin:

1) Name your startup whatever you want: Google has made URL’s completely irrelevant - it doesn’t matter at all that these guys don’t own Not an earth-shattering point, but people still think they need the right URL for their product name. Just name your product whatever will resonate most with customers then make a URL with “get” or “only” or “app” after the name - when people type it into their search bar Google will take care of the rest.

2) Kickstarter-y Things Will Have Some Backlash Soon, and Coin may be the tipping point: I’ve gotten a few things from crowdfunding campaigns and been underwhelmed with most. In my experience they don’t ship on time, often don’t work as advertised, are outdated by the time you get them, have varying levels of customer support, etc. We (perhaps unfairly) assume that because someone can make a tight product demo video they can make a great product with support and all the other niceties we expect from great companies. It’s really hard to nail that stuff. There’s only a handful of companies that do and you know them all. And, while they are “raising” money with pre-sales, it’s empty money - if these products had raised some sort of formal cash, they’d have support through this process from people with experience and a vested interest. Instead, we throw them money and say “figure it out!” This was fine early on, because Kickstarter was full of early adopters who understood these risks and limitations. Not with Coin. Most of the people I saw who ordered them aren’t early adopters - I can pretty much guarantee they’ll be disappointed. When it ships, I see a whole bunch of “this thing sucks” tweets as vendors don’t accept it, mastercard (or whoever) isn’t compatible, whatever. The first iPhone stunk, and that was Apple.

3) I ordered one, and it was like 40% because of peer pressure. All that said, I ordered one. I love the idea and hope it works. I also felt pressure when I saw people who weren’t early adopters buying them and wanted to prove I was an early adopter. Is that ridiculous? Absolutely. Is it incredible product management by Coin? Yep. I thought I was above all that stuff, but apparently not. Touche, Coin.

Five Sentences On: Allen Iverson and Authentic Branding

Allen Iverson officially retired from the NBA yesterday - you can watch his heartfelt retirement speech here.

Allen Iverson was my favorite basketball player not named Michael Jordan. I’ve never seen anyone so small (he was maybe 5’9) be so intimidating, aggressive, and ruthless.

I’ve also never seen anyone so honest and comfortable in their own skin in the face of constant criticism.

That authenticity is what I’ll miss most about AI.  Special players are now identified at such early ages that their personalities are seemingly stolen or stunted by advice that the vanilla, LeBron James no-stance-on-anything path is the quickest to marketing dollars.

My fondness for AI and indifference for LeBron is a good lesson for brands: people respond to authenticity and are incredibly good at sniffing out phoniness. That doesn’t mean lying - of course that’ll surface - it means things like outsourced social media PR or a founder who doesn’t truly believe in their product post-pivot.

No matter what your authentic looks like, and a lot of people didn’t like what AI’s authentic looked like at first, it’s better than the alternative.

The Brilliance of Snapchat

For two years I didn’t think Snapchat was a big deal. 

The press surrounding Snapchat’s new “Stories” feature helped me to finally see the light: Snapchat is the best proxy for human interaction on the planet.

I have no opinion on Stories yet, nor did it factor into my moment of clarity. It was the press, and a few subsequent conversations, that opened my eyes to the brilliance of an app I once described as a “frivolous sexting tool I wish I’d had when I was 17.”

Sarah Lacy discusses communicating with her husband “almost exclusively” through Snapchat (they work in different cities). My friend Nick tells me Snapchat keeps his sometimes-tenuous relationship with his remote cofounder light, going as far as to say it’s “saved their working relationship.” My cousin claims he hasn’t friended someone on Facebook in years, but he’ll add people on Snapchat so they can “get to know me.”

That doesn’t sound like frivolous sexting to me.

Facebook and Instagram are aspirational platforms used mostly to brag. They probably make you depressed. These are not earth shattering observations.

I use Instagram a lot. I check Facebook daily, but that’s a dying habit. What I don’t like about both platforms is that when you post, it feels like you’re screaming “this is a good representation of how I want to be viewed,” or more accurately, “This is the best I’ve got!”

There’s a lot of pressure that comes with “this is the best I’ve got!” Thankfully, real life doesn’t have too many moments like that.

That’s what the 23 year old founder of Snapchat, Evan Spiegel, understands so well. Moments are fleeting. Most things in life aren’t permanent. When I make a bad joke with my buddies, I don’t carry a sign around with that joke on it for the next 5 years. I move on and make another one 5 minutes later.

Evan Williams, cofounder of Twitter, gave a brilliantly simple explanation of successful tech in a recent interview:  

“Take a human desire, preferably one that has been around for a really long time…Identify that desire and use modern technology to take out steps.”

We desire to share our lives. We want to invite people in. We date people we meet at school or work because they are, by default, thrown into our circle of intimate daily moments. These moments aren’t pressure filled - they’re often routine. And they’re really, really important. They’re the moments Sarah described sharing with her husband.  

When I worked in finance, I hated that I didn’t get to choose who I spent 90% of my life with. Snapchat, at it’s core, is about choosing who you share these critical moments with. They do this significantly better than any service out there, and that’s a big, big deal.

How PED testing brings parity to Major League Baseball

Note – this has nothing to do with eship - I thought of making some correlation to how the Rays are running a Lean franchise, but to be honest I just felt like writing about sports on the Metro North this AM. 

The Yankees went on a run from 1995 – 2012 where they made the playoffs 17 times in 18 years. A number of good players came up through the farm system, and these players were supplemented by top, established talent signed in the free agent market. These players were low risk, and came with a prohibitively high price tag (the Yankees were one of a handful of teams that could spend the kind of money they spent). Their returns were predictable. These free agents were somewhere in the 28-31 age range, and would be at the top of the game until their late 30’s. I’ll use one quick eship analogy - The Yankees used the rest of the league like an incubator, with the last year or two of a player’s contract being their demo day.  If they proved themselves, the Yanks would fund the hell out of them.

The above strategy was always weighted in one direction or the other – sometimes the homegrown talent were the ones signing the big free agent contracts – but any time during that stretch if the Yankees were weak at, say, first base, they’d simply sign the best free agent first basemen on the market. This was not always a formula for World Series titles, but it was always a formula to keep them safely in the top 3-5 teams in baseball every year.

In the PED testing era, this strategy no longer works.

I think the most glaring effect of the PED crackdown has been the length of time players are at the top of the game. Without PED’s, when players turn 32 their physical abilities start to dissolve and their propensity for, and time recovering from, injuries increases. Once players hit 35, the drop-off is pronounced, save for a tiny group of outliers.

What this means is that when the Yankee sign a 30 year-old player who’s been at the top of the league for 5 years, their window to stay at the top of the league is maybe 2-3 years as opposed to the 5-8 during the steroid era. Contract lengths haven’t adjusted, so players and agents expect the 8 and 10 year deals elite players were awarded in the early 2000’s when they sign that “second contract.” This means teams like the Yankees end up paying the Arod’s and Pujol’s of the world top dollar until they’re 40 and completely useless. We’ll see if Robinson Cano’s deal follows suit. 

This heavily stacks the odds in favor of the model the Tampa Bay Rays have been forced to employ, since they couldn’t afford that “second contract” even if they wanted to. Developing and drafting talent, signing young players who have shown flashes of brilliance to long deals at reasonable prices (Longoria, Price, etc.) , then unflinchingly flipping them once they hit their prime (Shields, Garza, Crawford, Pena, etc.) for 4 more prospects like Wil Myers is a real strategy for sustained success.

It used to be that most 33 year old “superstars” were better than 25 year old superstars, simply because their physical skills were intact but they were 8 years savvier then the 25 year old version. That’s no longer the case.

So even though the Rays can’t afford their star players in that second contract, those players are almost immediately less effective then they were for the Rays when they were 25 - and are now under huge contracts guaranteeing the team will need to trot them out at high prices when they’re 36 and average. I’d argue it’s better the Rays can’t afford them, so it forces them into the right decision of flipping them in their prime. They’ll have an advantage at most positions by staying young.

Sure, experience plays a role when you’re trying to win a championship. The Rays showed a lack of poise when the made the World Series a few years back that cost them despite having a more talented team.

But as the average age of the best players gets younger, parity will increase, and the ability to draft and develop talent will become (already has become) far more important than the ability to buy it later on.

This year, the Pirates, Royals, Indians, Rays, A’s, and Orioles have either earned or are contending for playoff spots. The tides have turned.

The Yankee fan in me hates this shift. The entrepreneur in me loves it. Creativity and strategy are winning out over money. Unfortunately, my team is on the wrong side of that equation. 


Social Media Power Rankings

Not 5 sentences, but with all the preseason NFL stuff going on I’ve got Power Rankings on the brain. Here are my current Social Media Power Rankings (tried to limit to 5, but that left off some heavy hitters so I expanded to 10): 

1)   Twitter – Gets better the more you use it, my #1 source of news, nothing else is really close.

2)   Instagram – Best representation of my actual friends, most “pressure” of any social network (posts are high quality), and I’ve enjoyed video (though it’s drastically different from Vine for this reason).  

3)   Foursquare – The best network for discovery – seeing my friends go to and like a restaurant guarantees that I’ll at least check out it’s fsq profile/reviews/pics. And I love the ad potential. 

4)   Tumblr – I like posting, but I don’t really have a great set of blogs I follow – I find the cool ones like Natgeo post so much they overshadow my friend’s posts, and the format isn’t scroll friendly like the 3 above.

5)   LinkedIn – Maybe it doesn’t belong on this list, but checking profiles of people you’re about to meet with makes it indispensable. 

6)   Snapchat – I don’t really use it (I’ve MAYBE sent 2 pictures) and I’m not even sure it’s a social network. But my friends love it. Not my thing I guess, but I see the value and love the integrated ad potential.

7)   Facebook – I check it out of habit, but get 0 value out of the actual site and haven’t posted something in probably a year. Their current value to me is being able to log into other sites and sync my network. This is diminishing, as friending new people I meet happens less and less.

8)   Vine – I wish it were higher, and I enjoy the best Vines, but I realistically check it once every two weeks and only when prompted from a tweet.

9)   Path – No one is on it…but it’s so pretty. If people used it, I would jump on it in a second - for whatever that’s worth. 

10)Google+ - Is there a stranger feeling than that alert email that someone added you to their circles on Google+? It’s very confusing, then leads to 5 minutes of aimless wandering through the feed and realizing that the last friend post was from my sister in like 2012. I actually still have faith in G+, as Google is so integrated into our lives they can continue to force feed it. But for now it’s nothing but an occasional Google Hangout vehicle. 

Five Sentences On: Uber, and Visa as Tiger Woods

I’m not going to talk about the specifics of the Uber fundraise – I’m more interested in my Dad’s thinking on Uber’s potential vs. mine.

I told my Dad what Uber was and the valuation they raised at, and he didn’t believe the market warranted a $3.5 billion valuation.

I pointed out that Uber is poised to disrupt “local” payments – restaurants, coffee shops, bars – a huge market that Google was prioritizing.

My Dad’s response was that “Visa and those guys will never let that happen,” whereas my thinking was that there’s nothing Visa can do to stop it.

When Tiger Woods was at his best, it seemed like other golfers were scared to challenge him – they were beaten before they stepped on the course. I’m not saying that Uber will definitely win the local payment space. I am saying that recent successes of startups over huge incumbents may have this generation of entrepreneurs thinking a bit differently from the previous (my father has been an entrepreneur all his life). This generation seems confident in their ability to stare down the Tiger in the industry, seeing every company on the planet as vulnerable and every market as accessible.

#FiveSentences On: What Startups Can Learn From Psych

*Bonus 10(ish) sentencer - I’m fly fishing in Montana and won’t have a post the rest of the weekend.

I think it’s important for entrepreneurs to study anything with a cult following.

I usually try to stay in the loop on cult TV shows, at least until I have an idea of what earns them their following (AKA how I rationalize watching 8 episodes of Breaking Bad at a time).  

A somewhat obscure cult TV show is Psych, a show about a fake detective on USA, currently entering season 8. The show hinges on Shawn Spencer (played by James Roday), and his relationships with his best friend, Gus (Dule Hill), and love interest, Juliette (Maggie Lawson).

Psych is hilarious, unique, highly targeted (if you don’t get obscure 80’s and early 90’s pop culture references, you simply won’t like it), and embraced social media from day one.

However, these characteristics are table stakes for any “successful” TV show – what gives Psych a cult following?

In my opinion, it’s one thing: Truth.

As I mentioned, the show is great because of the relationships of its main character, Shawn Spencer. He’s hilarious, quirky, and hopelessly in love with his co-worker, Juliette.

Ask viewers and they’ll say Shawn’s and Juliette’s relationship feels real - more than other “TV relationships.”

Why? Because it is real - Juliette and Shawn (James and Maggie) met on set season one and quickly started dating - they have been since.

Customers/Viewers are incredibly good at sniffing out anything phony. It’s impossible to brand/market/build something you don’t believe in – customers will see right through it.

Luckily, the opposite is also true. They’re great at finding authenticity. Build something you believe in, throw yourself into your product, and people will pick up on it.


*This is a big reason clones often don’t work - Poke, Google+, etc. - but that’s for another blog.