My two year old is a better person than Uber’s CEO

Kids fight.  Sometimes there’s only one of the toy that they decide they need.  Other times one will take something that really does belong to the other.  And still other times, they just get lost in the moment and rough playing devolves.

And sometimes things escalate to the point of tears or one of them just being way too mean. When any of these situations arise, we (the folks who brought these two into the world) call a time out.  Playing stops.  Toys are put down and we tell them to face each other and apologize.  Here’s where the real fun starts.

The five year old, doesn’t like to apologize.  He doesn’t like to admit any wrong doing, even when he’s crazy, crazy wrong.  Like when he’s gone so over the line, that any grey is distant memory.

He always tries to think one step ahead, to spin his apology, to find some way, any way , to minimize his guilt.  What he fails to understand is that all he has to do is say “I screwed up.  I made a bad decision.  I’m sorry and it won’t happen again.”

Instead, he refuses to make eye contact, looks down as the lame and often forced words fall from his mouth.  He succeeds in saying he’s sorry, but he fails to be sincere.

The two year old is a totally different story.  As soon as things escalate, he knows he’s in the wrong.  Even if he didn’t start it, he looks his brother in the eye and says he’s sorry.  Immediately.

He’s not thinking about getting away with it because there’s nothing to get away with.  He’s busted.

The funny thing is, even when things aren’t his fault and we bring the boys together, he apologizes.  Does he not understand what it means to be sorry?  Maybe, but I don’t think that’s it.  I think he’s sorry for the situation that he helped cause.  I think he realizes that things got out of hand and he played a part in it.  What he wants is to go back to the way things were before they escalated.  He wants a return to normalcy.

I guess I’m not surprised that Ãœber cheated and did something down right low to their competitor Gett.  But their apology, er statement was way too five year old, and not nearly enough two year old.  They purposely stole time and money from Gett’s drivers, and damaged Gett’s brand.  I don’t care that they claim they paid cancelation fees.  This is much bigger than those fares.

What Über really did was steal potentially positive first experiences of new customers with Gett.  My first experience grabbing an Über was down right magic.  I immediately saw how much of an improvement it was over cabs and pretty much every other way to pay for a local ride.  For that three day period, Über robbed Gett of that potential good will and that is a much bigger problem.

I used to love Ãœber.  They brought ice cream to my office, have safely taken me hundreds of miles, most of their drivers rave about their new found financial success and control over their lives, and only once did I feel like my life was in danger.  But the fact that their CEO thinks that one of his teams conspiring to materially damage the the business of a competitor was just “too aggressive” and not wrong, is troubling and telling about what’s really behind the curtain of Ãœber.

I’ll give you a hint, it’s not a scrappy underdog trying to better your life, it’s actually an evil incumbent who thinks they can do no wrong and will stop and nothing to crush the next Ãœber to roll into town.

All Ãœber’s CEO Ryan Graves needed to do was to say was “We screwed up.  We’re sorry.  It won’t happen again.”  Sure, he can’t say anything that would make it sound as if the tactic was his, or any manager’s idea, but he still should have actually apologized.  I for one, am sad that he didn’t.

Parenting is not about stuff

Like every man, I remember my first time … I had some high hopes. You see, my wife was really pregnant, and I really liked stuff … so this should have been fun for us, but it just wasn’t. In fact, it was actually kinda stressful. Our first visit to Isis Maternity just wasn’t all that soothing and educational zen that I expected to walk into.

So the big news yesterday was just how fast Isis had shutdown. The Twitterverse was shocked and awed. There were some great articles trying make sense of it all. The arm-chair quarterbacks have been out in force but as someone who has two kids and two flamed out businesses to my name, I was amazed they was ever even IN business. Here’s why:

There’s a hole in the bucket dear Liza, dear Liza.

You better capture some MAJOR cash from your customers if they only have half a gestation cycle to give it to you. The first five months you’re just not buying stuff. The second five, you’re starting to read about all the crap you (think) you need to pull off this parenting thing. And then there are baby showers and all the other random gifts. We did it all and had many generous and willing co-conspirator, but by the time we had the second one …

Having a baby is not Nascar.

While having a baby is a really repetitive thing ((sleep, feed, poop) X every day until 1 year), it’s not Nascar. You don’t go straight, then left, then straight, then left a whole bunch of times and then pit for new tires. Babies are soft and cuddly, they really don’t wear stuff out (except disposable diapers, which I’m pretty sure they didn’t sell). So once you have it, you use it, and then use it again, but when you’re done, it’s not like those Nascar tires with 1000 left turns on them. The things you bought from them (for list price, ie: a lotta money) are like books. You didn’t read the words off the pages, they still work and can be read by the next mommy and daddy. So you give it to someone else who will use them, love them, and then pass them along. Boom another customer for them gone or maybe like us, they roll for $40 in parts and then never come back.

But people will always be having babies …

Likely true, but their market wasn’t everyone having a baby, it was rich people having a baby. The store was stocked with nice to haves. Sure, we bought that $40 worth of pieces parts for our (hand-me-down) breast pump, but babies were making it before Isis and they will survive now in the post-Isis wasteland that we now inhabit.

But Content is King!

And man, that is where they killed it. They created (and emailed) great content. And seeing as how this is my jam, I was impressed by how well they did this. But, I’m left wondering as I sit in my nice armchair and toss short passes over the middle, what role content actually played in their death. I disagree that content is not king. I’d counter that content is kidney. Content is a vital organ that your business really needs in order to live a happy, prosperous life. Can you live with out it? Sure, but you’ll need dialysis (re: tossing tons of money after customer acquisition, etc) to do so. And it’ll stunt your growth and it will define how and where you live your life (ie: no 4 day camping trips in the woods).

I wonder if for Isis, their great content was not king or kidney, but life support. Their business obviously could not survive on it’s on, and in fact was kept alive long after it should have died.

Having a few failures under my belt, I am incredibly empathetic to the folks who gave years (and cash) to try and make Isis succeed. That said, I’m more impressed by the way they just shut off the lights and dropped the mic, rather than fighting any longer. It’s really hard to stop fighting and give up, but there are so many other, different fights that need to be fought. Hopefully their next ventures will be greeted with more success and provide even more great content.

Thank you Google

I spend a lot of my day, most probably, on email.  I spend more time consuming, thinking about, replying to, or acting as a result of email than I do with my sons (2 and 5).  I spend more time on email than I do awake with my wife in the same room.  I probably spend more time on email than I do sleeping.  I definitely do not sleep enough …

So Google, the company that is pioneering driverless cars, the fountain of youth, and “secure” internet searches did something amazing today, the took a really, really long time to deliver much of my email.  Their coverage of the event has an Googley quantity of stats and numbers to tossed in.  I guess those are supposed to make me feel like “wow, these folks really take this seriously.  After all, they’ve done some basic math to understand how many of their customers were impacted and math is, like, hard.  Right?”

The thing is Google.  I’m cool with this.  It’s ok.  I’m actually not mad at you at all … seriously.

Today you showed me just how terrible I am at email.  You showed me just how disruptive Gmail is to my day, to my productivity, to happiness at work.  The fact that it takes me until late at night to mostly get through my daily load (~300) and it’s only getting worse.

But today for the bulk of my workday, I was getting only about 50% of the messages folks were sending my way and it was glorious!  Guess what? I actually got to finish some things I started.  I actually got to help people when they needed my help.  The slower rate of incoming email actually had me checking less, and spending more time on tasks.

I know this is nothing new.  There are folks all over these here green internets waxing poetic about how they regained the spring in their step just by backing away from email more and for longer periods of time.  But I never thought this would work for me.  I’ve always prided myself on going above and beyond to get back to folks as quick as a can with as thorough an answer as possible.

It wasn’t all smiles and happiness though as I got about 50 really not-awesome emails whilst I was driving home and here I am at 1am with some still unread.  Maybe tomorrow Gmail will fail a bit harder so I can catchup.

T.O.M. and the Oreo

In 1997 I graduated from college.  Shortly thereafter, I landed my first real job.  I built web sites and interactive CD’s (remember those?) at a small B2B marketing agency in Cleveland, OH*.  It was a crazy place to work.  Not just because half the company smoked in the office and all of the company boozed in quantities that would have made Roger Sterling blush, but because of the manic intensity and sometimes brilliant creative team.

The night before a valuable RFP was due or new boards were needed for a crack-of-dawn meeting or we were just that behind again, it was frenetic.  Commands would explode from the creative director’s fishbowl office, bursting past the silvery evidence of his stress-driven chain smoking.   Copywriters would work and re-work the ideas while the art directors would try to create something awesome.  They would work in whispered fear of their boss, of failing.  And still, the continually impressed with the work that slowly paged out of the printer once the smoke cleared.

When I went through a brief, but intense, addiction to Mad Men, I often thought back to those career-shaping days when I had never really created or been a part of anything big but had that front row seat for the creative process from my side of our beautiful mansion attic office.  Someone at A&E either sat in my seat, or was one of those abused copywriters before upgrading from Word to FinalDraft.

I thought of those days again when I saw this tweet from Oreo during Great Blackout of ’13 on Sunday night.  Creating marketing that works is hard.  Creating marketing that is memorable and remarkable fast is much harder.  Someone, who likely didn’t get too long to celebrate their internet win, had the bright idea to have the team assembled with someone who could actually approve their work.   This was a great nod to the ever-present realities of creative marketing in a corporate environment (17 approvals to tie one’s shoes) and the need to not pass go to collect the $200 (or 15K retweets) today’s social word.

I really hope the folks at 360i and Oreo who pulled this off had a much less stressful (and smokey) Sunday than those nights in my now distant memory.  But even if their night was just as sucktastic, it was worth it.  In mear minutes they created remarkable and memorable marketing and ruined every marketers’ 2014 Super Bowl Sunday to boot.

* My job title at this firm was Technical Operations Manager, or T.O.M. for short.  Yeah, we thought that was pretty funny.

My awesome shirt

Last Wednesday I wore a new shirt to work.  This might not seem like a big deal to most people, but for me, it was.  You see, this shirt that I speak of, wasn’t a t-shirt and actually had a collar and buttons.  Ok, to be totally honest, while it did have a few buttons, the primary fastening duties were  handled by snaps.  Yes snaps … that awesome.

Despite the awesome that was this shirt and the event of it’s unveiling, the truly awesome part of the day was that that night, while sitting in the old television room* at home with my wife, I happened upon the news that there was a new video on the excellent Dev & Design Blog at work: Keeping Busy During The Winter.  After watching and like it so, I showed the video to my aforementioned wife.

“Wait, this is from today.” she uttered with more than a little surprise.  Yes, at 0:53 of the video, there I am, munching a yummy free pretzel at work while wearing my brand new shirt.  That awesome video went from shooting to the interwebs in hours and that is more awesome than my shirt.  Another example of HubSpot’s Product Team killing it.  Big props to the filmmaker @ssiskind.

* Yes, both the room (122 years) and television (8 years) are old.

Can you count to four thousand, five hundred and thirty-six?

My four year old is fascinated by numbers.  He regularly poses questions like the following: “Dad, what’s 40 + 40 + 40 + 3 + 0 + 1?”  I love how he tosses in the zero as a curveball.  He’s a funny kid.

Like the little guy, I too love to count.  Always have.  I’ve counted pretty much everything.  Letters on road signs as I drive?  Check.  Bonus points for all the letters and digits on license plates in between those road signs?  Achievement unlocked.  The ceiling tiles in my thermo class in college?  Definitely.  Cards at blackjack tables in Vegas, New Jersey, Indiana, Southern Cal, and Aruba?  Ding!

So when I finally cleaned off my glasses two years ago March and realized I’d gone from being a rail for the first half of my life to the width of the old-growth forest stumps that yielded the sleepers over the second half, it’s no surprise that I turned to counting for my solution.  So I started scanning bar codes and figuring out meals.  Data.  Counting.  Awesome.  And amazingly this overpriced iPhone did more fo my health than any gym membership I’ve ever had.

So, it’s been nearly two years and after a brief respit from counting and caring about my fattitude this past fall, I’m back at it.  Counting like the good ol’ days of license plates and doubling on a nine.

Oh, and I bought an ice cream maker attachment for our stand mixer.  I’m just full of good ideas.

Let’s get dirty with some home made ice cream counting with tonight’s recipe, a variation of the ridiculous Philadelphia Chocolate with peanut butter from David Lebovitz’s amazing The Perfect Scoop.

  1. Green & Black’s Organic – Dark 85% Cacao Bar – 625 calories
  2. Sugar In the Raw Natural Cane Turbinado Sugar – Sugar, 1 cup – 720 calories
  3. Heavy Whipping Cream, 2.5 cups – 2,000 calories (wowzers)
  4. 2% Reduced Fat Milk, 1 cup – 130 calories
  5. Ghirardelli – 60% Cacao Bittersweet Chocolate Chips, 48 chips – 240 calories
  6. Skippy – Natural Creamy Peanut Butter, 7 Tbsp – 665 calories
  7. Confectioner’s Sugar, 1/8 cup (30gr) – 60 calories
  8. Rademaker – Dutch Processed Cocoa, 6 tsp – 99 calories

And the total for these three pints of awesome?  Four thousand, five hundred and thirty-six calories of awesome.

philadelphia chocolate and peanut butter ice cream

four thousand, five hundred and thirty-six calories of awesome home made chocolate and peanut butter ice cream

Oh yeah.  But, it’s just 189 calories per 1/2 cup serving.  And it’s got calcium in it.  Yeah. Calcium.

New jobs for both of us.

Yesterday was my first day at HubSpot.  It was my first “first day” at a job in a very long time.  There wasn’t really a first at my last company, play140.  We just got started.  There was no culture, no “way things are done”, nothing was set in stone.  That’s one of the coolest parts of startups, you get to do it all.  It’s exciting.  You can try to do everything right that everyone you’ve worked with or for before has done wrong.  And you’ll probably fail.  But that’s a part of the adventure.

HubSpot is still called a startup by some, but in reality, I don’t think it is any more.  This is a *big* company.  They have an unbelievable sales team who sell what is built here for real money every day to people who want to buy it.  They have set “way things are done” for just about everything.  They’ve been around for five years.  There are nearly 300 people here.  It’s kinda crazy.  Maybe I need to change the title of this blog …

While yesterday was my first day here, it was also my wife’s first day as a full-time Mom with our 3.5 year old, Thomas, and our 12 day old, Miles.  So while I was here trying to get up to speed on years of history, projects, work, style and about 30 new names to remember, she was at home entertaining our two monkeys.  I’m not sure who’s day was more exciting or exhausting.  She did let me actually get my shoes off before handing over Miles though.  So it couldn’t have been that bad. 🙂

Don’t be an idiot with your email address

Setting up email is pretty much one of the first outward facing things that a startup does.  You need to own your company identity, and folks need to associate you, your product, your everything, with that identity.  This often happens first via email.

So let’s say your name is Bob Fundergrass, you’re a founder, and your startup’s domain is  If I can’t email you at, you’re an idiot and you are doing it wrong.  I don’t care if you really use, or some other variation, but your first name, what people actually call you, better work.  If it doesn’t, you’re an idiot.

Please don’t make this mistake.  You’re a founder, claim that first name and own it.  Sure, maybe down the road you’ll have 30,000 employees and need a really stodgy, strict format, but right now, you need to make it as easy as possible for everyone and anyone to email you.  Your first name @ your domain is the easiest way to do this.

You have enough things stacked against you already, please don’t add bounced or black-holed emails to the list.

PS: An easy way to do this if you use Google Docs is to set up a Group and name it and set the Group email address as your “easy” address.  Then just set your main account as the owner and select “Also allow anyone on the Internet to post messages.”  Bingo.  You’ll capture those emails and be able to reply from your preferred address.

All your life are belong to us

102 weeks ago, I spent way too much time assembling a list of the folks we wanted share our “hey, our inside baby just became an outside baby” email.  This was not a fun process, but we did it anyway and I’m happy we did.  I also blogged the entire hospital -> labor -> birth from the tiny, craptastic “keyboard” of our long since gone, original iPhone.   In short, I worked to get the message, a message I was very, very excited about, out.

Today, not even two years later, things are different.  With my role at my new startup (+ dad of the aforementioned 2 year old, and husband of a super patient wife), I just don’t have much time to fart around online.  While the world has transition on to Facebook, I’ve slowly transitioned off.  This hasn’t been a big decision – no, I’m not taking a stand against the Rube Goldberg machine that is Facebook’s Privacy Settings.  Rather, it’s been a consistent string of small decisions – decisions not to open the app on my phone or site in my browser.  Decisions to not consume the little blips of my friends and family’s lives.

Missing out

You see, I have a serious issue with status updates.   I must consume them all.  This was easy when FB was small and I could count my “friends” on a couple of hands and feet, but now, even with very managed growth of my friends list and an iron “Ignore” finger for new requests, I just can’t keep up.  Since I can’t handle just a snack of my friends’ lives, for the fear that I’ll miss out on something, I’ve stepped away almost entirely.

In doing so I’ve missed two births and a tenure award/promotion.  Three life changing events that used to merit phone calls and emails blasts are now owned by Facebook.  When I found out the other day that friends of ours had their first child five days earlier I was floored.  Floored that I didn’t know, that I hadn’t somehow heard.  I *never* miss an email (note: this is not a guarantee that I actually reply, just that I never miss even one).  I was told “it was on Facebook”.  The same thing happened last week when my brother-in-law was awarded tenure and a promotion.  I missed it.  It was on Facebook only.  Sure, eventually I got a call with the info, but I’d missed it when it was news.

This seriously bums me out.  Not that I didn’t see these when they happened, or that I wasn’t personally notified, but that these really amazing, important, life-changing events have been dumbed down to a Facebook status update.  That the care that goes into an actual email, a call, a blog post, is gone.  Now that everyone is on Facebook, you can just carpet-bomb your life’s best moments into the stream that will get lost below the fold before you know it, and way before I know it.

Five rules for startup + family happiness

I spend a lot of time out and about at startup events here in Boston/Cambridge.  The scene has really been picking up steam lately, to the point where there are at least two or three really great meetups per week.  Being a pretty outgoing guy, I do a lot of networking and answer a lot of questions about our company, mentors / advisors, TechStars and the like.  But this post isn’t about any of them, it’s about my family.  Or more specifically, the question I get asked more than just about about any other – how do you have a startup *and* a family?

Rule zero – Pick an amazing wife / husband

Seriously, the only way to do this is to have someone who will really step up and do way more than 50% of the family work.  Someone who understands that this is what you need, that you have the startup defect(1).   Not everyone can handle the serious ups and downs of being married to a “you”.  The term “startup widow” isn’t a joke.  Respect that.  Seriously.  If after laying out the deal (leaving a well paying job, living on savings, working way to much), your spouse isn’t into this, stick with your job until you can de-risk it for him/her more.  And understand that they may never be into this life.  That’s ok.  It’s certainly not for everyone.   If that’s the case, maybe you can join a funded startup and still keep your startup defect happy.

Rule one – Learn to juggle

I’m not kidding.  Really, do it now.  Why?  Cause you’ll quickly see that juggling isn’t about having everything precariously up in the air.  Juggling is about control.  It’s about keeping as many things under control as possible and realizing that you’re constantly going to be losing control of something (a bit), but that’s ok when you’re gaining control of something else and have full control (ie: it’s in your hand) of the last ball.  For me there’s my company, TempMine, my wife, and my son.   I will never be able to do everything I wish I could for everyone.  It’s ok to let your startup fly a bit, so you can keep your wife happy (and sane) and your son remembering what you look like.  Just keep the flight of the company in mind and realize that you have to toss something else before the company lands.

Rule two – Keep everyone in the loop

If I have something family that has to happen, I let my team know.  If I have something startup that has to happen, I let my family know.  Sure, there will always be surprises, but work really hard to make them the exception, not the rule.

Rule three – Over deliver

Your schedule is just plain insane when running a startup, but you make sure you over deliver often.  If this means cranking late in to the night to get something done for your team, do it.  If it means blowing out of work early so you are home for bath-time on a day when you normally wouldn’t, do it.  Realize that your role is hard on everyone, but they’ll forgive you for a lot of the not being around if you over deliver when they least expect it.  This stuff also goes a long way towards keeping you sane.

Rule four – Weekly something

Every Saturday we have a family breakfast.  It’s usually a little  more elaborate then a regular breakfast.   We sit at the table (something we don’t do together often enough) and eat and laugh and just enjoy each other.  I make it.  I clean up after it.  It’s one of my favorite times of the week.  I don’t think it matters what you do, but pick something and do it with everyone.  I wish we could eat together every night, but for now, Saturday breakfast will do.

Hash browns, scrambled eggs, and sausages? Oh yeah!

So, what works for you?    Leave a comment!

1. What’s the “startup defect”?  Well, it’s that thing that makes you *have* to do this.   Starting a company that has a little chance of success and a major chance of eating up your savings and retirement is a *not* the smart thing to do – even when you’re smart person (and I hope you are, because I hear it really helps to be smart when running a startup …)