Inside My Brain

Thoughts about startups, tech, marketing, and life

CATEGORY: Startups

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, 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.

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.