Inside My Brain

Thoughts about startups, tech, marketing, and life

Honesty is the best policy

Last night I watched the 60 Minutes episode about why Greg Smith left Goldman Sachs – because the firm’s culture was degrading and the bank was being dishonest and ripping off its clients. This ignited some thoughts in my big noggin about how honesty and openness impacts a person’s and company’s success.

Over the last few months that I’ve been involved in startups and entrepreneurship, I’ve had many conversations with entrepreneurs about the companies they are building, their experiences in the past, and their lessons learned. What has awed me is how brutally honest they’ve been and how candidly they speak about their travails.

I think entrepreneurs HAVE to be brutally honest to have any chance to succeed. First, they have to understand what skills they lack and find co-founders and employees to fill those gaps. Once a team is built, they have to test their idea and iterate repeatedly to find product/market or service/market fit, many times completely scrapping the initial idea they were so passionate about. If there are problems with the product/service, team, or market, they have to be able to recognize this and change accordingly (like I did). Entrepreneurs need to be frank with their investors, advisors, and board members about their progress and need to communicate frequently and sincerely with their customers and employees to keep them. Not all of these entrepreneurs (nor I) are guaranteed success in the end, but being open and honest will give them the best chance.

It shouldn’t be any different for employees in large corporations, but we’ve seen many examples of dishonesty and deception, such as the Goldman Sachs story above, and the fall of Lehman Brothers and other financial institutions during the subprime mortgage crisis. Maybe it’s the pressure to maximize sales and profits that larger companies face from investors and shareholders that causes this dishonesty. Maybe senior management is corrupt from the start and fosters a culture of deception, which trickles down to lower-level employees. I’m not sure what it is, but I do believe that if you’re open and honest, both with yourself and others, you’ll be more successful in business and in life. And if you’re a company with an open and honest culture, you’ll find the same success.

I’d love to hear some other examples where dishonest companies and employees faltered, while honest ones succeeded.

P.S. I have read articles (like these in Forbes and NY Times) saying how Greg Smith’s story isn’t believable. Yes, the irony that this blog post is about honesty is not lost on me. 🙂

In the Startup World, They Say to Fail Fast…so I Listened

Here’s a great blog post called “Why I Quit My Job, Killed a Company in Six Weeks, and Still Feel Great!”. Well, you’re reading a similar post right now.

As you may know, I’ve been working on a startup called Dokkit. And as of yesterday, I’ve split up with my co-founders, only after a few months of working together. Wow, that was fast! Here’s what happened.

I thought of the idea for Dokkit about a year ago and fleshed it out.  I then started looking for some teammates to help build it. I attended startup events in DC, created profiles on entrepreneur matchmaking sites like CoFoundersLab.com, and just networked like hell.

Over the span of a couple of months, I found three developers who joined the team as co-founders, which was awesome, because the biggest hurdle for a non-technical entrepreneur is to find programmers to help build the product. We discussed the product strategy and they began developing. There were some debates about what technologies to use to build Dokkit, what the UX and UI should look like, and other important topics. We weren’t always on the same page about everything (which is completely fine), but the debating was enough for one of the developers to leave the team. I understood why and I moved on, continuing with the other two developers to build the product.

Then in July, I quit my job at the Washington Capitals to dedicate more time to Dokkit. Whoa! That doesn’t have too much to do with the story, but I think it adds some drama, right?

Anyway, a few weeks later, we performed a user test with about 70 people and got some great feedback. Unfortunately, that’s where our visions for Dokkit started to diverge. The team had some heated debates on what the purpose of Dokkit is, how the user would navigate through the application, and what the product would look like. I believed that our visions were too different to reconcile, and on a more personal level, I think the team just lacked cohesiveness and fit. Thus, I decided to leave, and the Dokkit team as we know it is no more.

Here’s what I learned from this:

-Move slow on some things, move fast on others – I should have moved a bit slower in forming the team. I wanted to build Dokkit quickly, so I recruited quickly and failed to take into account many of the “soft” factors, like cultural fit and alignment, that are so important in team-building. But I moved fast in leaving, which I think is a good thing. Maybe the team could have worked it out and become successful, but the signs were telling me to make a move.

-Seek advice from others who have been there – Before making a decision, I spoke with many entrepreneurs who have been through problems similar to what I faced. Their insight was absolutely crucial to my decision and I’m really grateful for their help.

-Failing feels oddly invigorating – Sure, I’ve failed before in my career, but in my mind (maybe not my bosses’), they were pretty small in the whole scheme of things. This is completely different since I’m on my own and the move has a big impact on my life. Nevertheless, I do feel great. I was definitely stressing out about the decision to leave, but now that it’s been made and I’ve “officially” failed, I feel kind of free and invigorated. It’s tough to describe.

The jury is still out on whether I’m going to continue to pursue Dokkit. I still love the idea, and regardless of the competition that has popped up in the past few months, I don’t think anyone has really figured out the smart social calendar space just yet. The funding world for consumer web apps has taken a turn for the worse, which of course will factor into my decision on what to pursue next. So as I consider what my next startup move is, I’m going to work on my consulting projects and continue to learn how to code.

So there’s the story of my first, and definitely not my last, startup failure. I failed fast but I think I failed right.

I know failure isn’t everyone’s favorite topic, but I think there’s so much to learn from it. I’d love to hear your thoughts about how you’ve failed, whether or not it had to do with a startup.

Recap of Tough Mudder

On Saturday, I ran the Tough Mudder race in Frederick, MD. It was awesome. Below is a recap and some lessons I took away from the race:

Tough Mudder is Extreeeeeeeeeme

The race entailed 12 miles of running and 20 obstacles involving mud, mud, and more mud, water, electricity, climbing, jumping, lifting, pushing, pulling and more. And on top of that, we did it all in a torrential downpour, basically running the entire race sloshing in mud and more mud! Crazy.

I’ve done a Mud Run in the past and that’s nothing compared to the Tough Mudder. This is a true test of both mental and physical strength and endurance. My entire body is killing me, I have cuts and scrapes all over my arms, legs, and torso and I even have bruises underneath my fingernails. It hurts to type this blog post, seriously.

Teamwork, Camaraderie and Perseverance are Essential

You can’t run this race alone. I ran it with two of my buddies and we pushed each other throughout the race. But it also felt like every Mudder was my teammate, as everyone helped each other scale the Berlin Walls, climb over the mounds in Mud Mile,  and complete many other obstacles. And even though it felt great for me to get past each of the obstacles, it actually felt better helping others complete them.

Everest was a killer obstacle where you had to run up a 15-foot-high quarter pipe coated in mud and grease, then leap and grab the hands of other Mudders, who help pull you over the top. One of my teammates had a lot of trouble with this one, primarily because “tall” isn’t a word you would use to describe him. In front of a gallery of hundreds of people, he tried to climb Everest about five times, each time sliding down in shame and embarrassment (I imagine he felt that way). On his final try, he was able to get a solid leap and we were able to grab his hands and pull him up. He never gave up and we worked together as a team to get him through it. It seems cliche but that’s what Tough Mudder is all about.

Poor Organization Made This Event Even Crazier

I don’t know whose fault it was, but the traffic going in and out of the event site was insane. 10,000 people converging on the country roads of Frederick, MD made for one hell of a traffic jam. It was so bad that we parked our car about two miles away from the event site and had to walk those miles before and after the race!

Overall, the Tough Mudder was amazing and I’d totally do it again. I have a sweet t-shirt and bright orange headband to prove that I finished. We’re going to try other similar races, like The Spartan Race, to compare. I’d love to hear from other people who completed the Tough Mudder or any other races about what they think.

What I’ve Learned After One Month On My Own

It’s been exactly one month since I left my gig at the Caps and I’ve learned a few things working for myself at home.

The more flexible and unpredictable your schedule is, the more important discipline and routines are 

Now that I’m on my own, I have complete control over my schedule. I can plan meetings when I want, I don’t have to start work at any specific time, nor do I have to commute to an external location everyday. But I’ve found that the unpredictability of this schedule can cause dips in productivity. Who’s to stop me from waking up at 10am everyday and only working until 3pm? I’m the boss, so I can do what I want, right? Sure, but I’d get absolutely nothing done.

So I stay disciplined and replicate my morning routine that I had while working for the Caps. I wake up at 7am, walk the dog, make breakfast, shower, then immediately start cranking out work. When Noon rolls around, I’ll either make lunch and eat, or fit in a mid-day workout. If there are days when I have meetings or I need to run errands during normal work hours, I’ll work into the night to complete my 10-12 hour workday. Staying disciplined and following a routine has been really helpful in staying productive working from home.

Power naps really help productivity, too

You’re probably thinking “WTF?!” after having just read the first section about discipline. But it’s true – power naps are awesome for productivity. Everyone’s been through the 2:30 in the afternoon lull at work and power napping helps me get through it. There have been articles in Inc., Businessweek, and other publications about how companies embrace nap time during the work day and studies show how this positively impacts productivity.

But again, I have to be really disciplined about this, or my 20-minute nap can turn into a 3-hour one (like it sometimes does on the weekend). I nap sitting semi-upright on my couch so I’m not that comfortable.  I set the alarm on my phone to ring after 20-30 minutes and place my phone across the room so I have to physically stand up to turn it off. After I wake up, I splash my face with water and immediately get back to work, feeling refreshed.

The highs are higher and the lows are much lower

The extremes are more amplified working for yourself.

In my past consulting gigs with Tefen and Navigant Consulting, closing a new project deal or completing an engagement was a big deal. At the Caps, a successful marketing campaign, the launch of a new mobile app, or a big win over the Penguins was cause for celebration. I’m not taking anything away from these events, as they definitely elicited happiness and excitement. But when you’re on your own, the littlest wins, like an insightful product test, a completed analysis for one of my consulting clients, or a meeting that went well, seem huge. I can’t even imagine how I’ll feel when something bigger like a product launch happens. My head will probably explode.

On the flip side, the lows feel really, really low. Projects that move slower than I expect drag me down more. Reading about how the stock prices of Facebook, Groupon, and Zynga are dropping like a bag of bricks doesn’t give me much confidence as I build a consumer web app. The doubt that creeps in can be paralyzing.

But that’s the game I’m playing and I need to deal with this roller coaster.

That’s all I have for now. I’d love to hear from other entrepreneurs about their everyday experiences, or from anyone who works from home.

The Importance of Disconnecting From Work

I wrote a blog post a few weeks ago about how sometimes I wish life were simpler and we could more easily disconnect from our gadgets. Lately, there’s been a lot of content out there about how to better disconnect from work, which is something that I and many people have a problem doing.

When I was working at the Caps, I almost never disconnected from work when we were in-season from September to May (too bad not June). That’s nine months non-stop of constantly reading and writing email, strategizing, executing, managing, firefighting, and stressing. I’d take a few days off in February or March each year to go snowboarding out west, but I’d bring my laptop and catch up on some work during downtime and really never stopped thinking about it. I otherwise rarely took vacation in-season. This is a recipe for burning out, which I admittedly did towards the end of every season.

Now that I’m on my own working on Dokkit and consulting, it’s gotten even worse. And I’ve been doing this for only two weeks!

That’s why I love these articles and posts about how small business owners and startup CEOs are approaching vacations and completely disconnecting from work, whether it’s for themselves or their employees.

This NY Times article shows how you can prepare yourself and your company for when you take a real, disconnected vacation.

This post from a startup called Full Contact talks about their Paid Paid Vacation policy – not only do they pay your salary when you are on vacation, they actually pay for your vacation, too! Awesome!

This Inc post talks about how Red Frog gives their employees unlimited vacation time and how that really helps them be more productive.

It’s tough but I think we can gain a lot from being truly disconnected from work every now and then. What do you think?

Don’t Be Afraid to Take That Big Step

Fortune Big StepFortune SaltThat’s what the piece of paper from a fortune cookie told me. It also told me how to say”salt” in Mandarin.

I held on to that fortune and now I’m following its wisdom (not the learning Chinese part).

Today was my last day at the Washington Capitals / Monumental Sports and Entertainment and I’m leaving to work on my tech startup, Dokkit. Check it out, sign up, and let me know what you think!

My time with the Caps and Monumental was amazing. I worked with so many smart people and learned so many things that will no doubt help me in the future. I’m really appreciative of the opportunities and responsibility that I was given here. And I got to watch hockey games for a living! As awesome as this job was, it was time to take a shot at this entrepreneurship thing.

I’m in for the ride of my life. I have no idea what I’m doing. I’ll have no income for a while. I’ll never work harder, face more uncertainty, and ride more of an emotional roller coaster than I will now. Fellow entrepreneur Daniel Odio told me that working on a startup is like “getting punched in the face all day, then waking up the next day to do it all over again.” Awesome, can’t wait. I’m nervous, excited, stressed, and scared. Really scared. But I’m doing it anyway. I might fail or I might succeed, who knows. But I have to take a shot.

Go big or go home. Shit or get off the pot. No regrets. Or any other motivating tagline you want to use. So if you’re thinking of making a move, I say, “Just Do It.”

But it all begins by taking that big step.

What if life were simpler, like on TV shows?

Don Draper Drinking

Dedicated to the winners and the losers, Can it be that it was all so simple then?
Dedicated to all Jeeps and Land Cruisers, Can it be that it was all so simple then?
-Wu-Tang Clan, “Can It Be All So Simple”

Some of the best shows that are or were on TV take place in another era. Shows like Game of Thrones, Deadwood, Downton Abbey, and Mad Men portray how times were back in the day in different parts of the (sometimes made-up) world. When I watch these shows and think about how life was so simple, I sometimes ponder whether I would have rather lived in those eras as opposed to now.

Technology has no doubt made us more connected, efficient, and productive. But it has, to some extent, shortened our attention spans, trivialized relationships, and overwhelmed us with content. So, would I trade today’s complex, gadget-based life for a simpler, less cluttered life back then? Let’s compare.

  • Game of Thrones – Days filled with practicing sword fighting or archery, drinking arbor wine and eating salted beef and pigeon pie seem pretty cool, but I’ll pass on riding horses all day, ugly clothes, and not bathing.
  • Deadwood – Pan for gold, sell some tools, drink whiskey, visit a whorehouse and form a government – not a terrible life. But the bumpy dirt roads, uncomfortable boots (I have flat hooves and those boots would hurt) and risk that someone can just come up and shank or shoot me outweighs all the good simple things.
  • Downton Abbey – Life’s pretty good if you’re a Crawley, but even getting waited on all day might get annoying, and so might those accents.
  • Mad Men – Sipping whiskey or vodka at 11am while thinking of clever taglines, followed by a liquid lunch with a client, followed by a nap on the couch in your office, followed by a liquid dinner, all while styling in a sweet suit? Awesome! Transistor radios and black and white TVs don’t compare to iPods and HDTVs but I think we might have something here.

All non-funny jokes aside, I wouldn’t trade today’s life for any of those in the above TV shows. But there are times when I’m overwhelmed with emails, tweets, newsletters, meeting requests, etc. and I just want to sit back, take a swig of vodka and score a nap.

What do you do when you get overwhelmed with a ton of communications and content? How do you disconnect from the clutter that technology brings? Would you trade today’s life for the simple life in one of those shows?

Birthday Thoughts – This One Feels Different

Today is my 34th birthday and though 34 isn’t a “significant” number like 21, 30, or 40, this one feels important and really different to me.

Maybe I’m just a little more mature, though my actions going out in DC later tonight might prove different.

Maybe I’m just getting old, like my ankles, wrists, and back are telling me.

Maybe it’s because I’m now engaged to be married to my beautiful fiancee (never did that before!).

Maybe it’s because I read this blog post by Brad Feld this morning. Which made me think about all of the life changes that are coming soon (more about this at a later date).

Regardless, this one feels different. Good, but different.

Eh, I’m probably just getting old.

Do you work to live or live to work?

Think about it. Which one describes you?

You “work to live” if your job is a means to provide for the other parts of your life, such as having an awesome social life, acquiring desired possessions, traveling, caring for your family, etc.

These people typically have very stable, well-paying, 9-to-5 jobs.  I have friends with children who work primarily to care for their families, and others who work to go out to eat and drink five nights a week. I’d say a lot of accountants work to live (my accountant friends – I’ve heard your complaints, don’t fight me on this) as do others in very traditional industries such as CPG and manufacturing. You can definitely like your job but it isn’t what drives you in life.

You “live to work” if you are super-motivated at your job, proactively look for problems to solve, and are willing to sacrifice, whether it’s money, stability, a social life, whatever, to pursue a career that you truly love.

I’d say that most entrepreneurs embody the “live to work” principle, typically sacrificing job stability and a social life to build something they are passionate about.  Many who work in the sports and entertainment industries live to work as well, typically forgoing a larger salary in other more lucrative industries to work with more exciting subject matter.  Writers and journalists may also fall into this bucket. I’m sure I’m leaving many other jobs and industries out, so please comment to include yours.

One camp isn’t better than the other, and there are definitely pros, cons, and sacrifices made by people in both segments; it all depends on life’s priorities.

So do you work to live or live to work?

What’s your version of winning the Super Bowl?

Eli Manning SB trophyI’m a big NY Giants fan, so I was totally pumped when they won the Super Bowl this past Sunday. But as I watched the Super Bowl parade yesterday and saw all the players’ and fans’ happiness, I thought to myself – What’s the normal person’s equivalent of winning the Super Bowl?

We’re all professionals at something, just not a professional athlete at the highest level and the biggest stage.  I think of the times that I’ve felt really good after accomplishing something, and I bet it pales in comparison to what Eli Manning or Tom Coughlin felt. What’s the career equivalent for people like you and me? Is it landing a big sale, getting that promotion or completing that big project successfully? I’m not sure it compares to lifting the Lombardi trophy over your head. Or if you’re an entrepreneur, maybe it’s selling your company or filing that IPO?   I should ask Mark Zuckerberg soon.

Maybe it’s something personal, like getting married or having a child? I don’t know, I haven’t done either of those. Or maybe buying that shiny new luxury car or big house, which signifies that you made it? Who knows.

So what is it? Have you ever felt such a sense of accomplishment that you felt that you won the Super Bowl of your world, and if so, what happened? Let me know!