Inside My Brain

Thoughts about startups, tech, marketing, and life

TAG: Startups

Startup Weekend DC Recap

Startup Weekend DC (SWDC) was held this past weekend at 1776 and I volunteered to help out with the event. It was an awesome experience, and here’s a quick recap.


Startup Weekend events bring together entrepreneurs who launch startups in 54 hours. Non-technical people, designers, and developers pitch ideas, form teams, build products, create a pitch deck, and present their work to a panel of esteemed judges at the end of the weekend. Many teams continue to work on their ideas after the weekend is over, and businesses are launched as a result. It’s a long, intense weekend but invigorating and motivating for everyone involved.

The event started on Friday evening with some introductions to the weekend’s format and an exercise that simulated what would happen over the next couple of days. Basically, impromptu teams were formed and were provided with two random words with which they had to create a logo and business concept and pitch it to the crowd. The teams came up with really creative ideas, and that set the tone for the weekend.

Attendees then pitched their own ideas for products that they wanted to build and recruited others to help them do so. There were about 35 ideas pitched, ranging from a website for mock interviews to a karaoke app, and the total was whittled down to 16 that were actually pursued. Teams were formed and they started working until 1AM.

The work continued Saturday morning at 9AM. Throughout the day, teams were brainstorming ideas, validating their concepts, creating mockups, coding, designing, and developing business models. Mentors were helping the teams refine their work. And we were there to support the attendees with advice, food, and lots of caffeine.

On Sunday, there was a palpable tension in the air, as teams had to present their pitches at 5PM. The participants were scrambling to finish their prototypes and put together their pitch decks. Some teams were confident while others were sweating, but everyone was cranking. It was intense!

The pitches were great (you can view them here) and the amount of work these teams did in such a short amount of time was amazing. The best pitches clearly communicated the value proposition of the idea, had a simple prototype that showed how the product would work, and addressed the business potential of the concept. The prize winners were as follows:

  • First Place – HelpCloud, a customer service application for Google Glass
  • Second Place – Traject, an analytics platform for non-profits
  • Third Place – Blossom, software that analyzes your text messages
  • Honorable Mention –, a video platform that helps you discover bands playing in your area

But all sixteen teams did an awesome job!

I have a deep connection with Startup Weekend. I attended SWDC in November 2011 as a participant, and it really confirmed my desire to be an entrepreneur. At that event I pitched Dokkit, my smart calendar idea. Though I didn’t get to work on Dokkit over that weekend, I gained so much knowledge about how entrepreneurship worked. I learned how to do an elevator pitch, worked with developers to create a product, put together a pitch deck, and met a bunch of really smart and motivated people with whom I stay in close contact with today. The event solidified my desire for entrepreneurship so much that I quit my job seven months later to pursue my startup! SWDC had such a positive impact on my life and it was awesome to give back by volunteering.

Props to SWDC co-organizers Mack Kolarich, Denis Baranov, and Barbara Lee, 1776, and all of the mentors, judges, volunteers, and participants who contributed to this great event. DC’s startup community is certainly alive and kicking, and I’m looking forward to helping out at future Startup Weekends!

Breadth vs. Depth – What’s Better For Your Career?

I’ve thought a lot and have had many discussions about this throughout my career. Should I be a generalist and build a broad base of skills and knowledge so I can be flexible and work different jobs in many industries, or should I go deep into one specific skill and/or industry and become a specialist? What’s best for long-term success? Forbes and the Harvard Business Review thinks generalists will rule the future; I tend to agree but I don’t think it’s that cut and dry.

There are some careers where it’s necessary to be a specialist, otherwise you likely wouldn’t have a career. College professors and scientific researchers come to mind; you need to be an absolute expert on a particular subject to be successful.

On the other hand, industries like consulting, which is where I started my career, breeds generalists. Consultants, especially in the early stages of their careers, work on a wide array of projects across many industries. As they become more experienced, some may focus on a particular function (such as strategy, marketing, or operations) or a specific industry (e.g. healthcare, technology, consumer packaged goods), or a function/industry combination. But overall, consultants are armed with a broad array of skills and knowledge that many take with them to executive positions at other non-consulting organizations.

So, like with many questions, the answer is, “it depends” – on your goals and your personality.

If you want to start or lead a company, having breadth is a must because you have to understand all aspects of your business, including sales and marketing, product development and management, engineering, finance and accounting, human resources, and more. Sure, you can outsource or hire specialists to handle many of these functions, but you must have at least a cursory level of knowledge of all of these to effectively run a company.

You can also do really well by being a specialist. You can focus on a particular sector of finance (e.g. fixed-income investing), marketing (e.g. email marketing), engineering (e.g. Java programming) or any other function, and be the go-to guy or gal in that specific field within your organization. Additionally, you will presumably really like what you do, since you’ve found enough affinity for it to specialize.

I’m in the generalist camp. Like I mentioned earlier, I started in consulting and enjoyed jumping from client to client and working on different types of projects. As a marketer for the Washington Caps, I liked touching many different aspects of the business, such as CRM, database marketing, advertising, mobile, social, and analytics.

And in my current career of launching a tech startup, I believe being a generalist will serve me well. The various marketing and strategy roles I’ve played will help me acquire and retain customers and map out the future for my company. And I’ve broadened my skills even further by learning programming so I can work more closely with software developers and add value to them when I can.

So for me, the preference for being a generalist boils down to a couple of reasons: 1) I want to start and lead a company, so the generalist business skills are necessary, and 2) I would probably get bored if I focused on only one specific function. And while I think a broad array of skills is powerful, augmenting that with some deep knowledge of a particular industry makes for the best recipe for professional success.

What do you think? In your field, are you a generalist, specialist, or a mix of both? What pros and cons have you seen being so?

NYU Entrepreneurs Festival – A Great Conference That Caused Some Mixed Emotions

ImageThis past weekend I attended the NYU Entrepreneurs Festival in New York City. And contrary to what you may think I meant by the title of this post, I had no mixed emotions at all about the event; it was an absolutely amazing and well-planned conference. I titled this post as such because attending the festival made me feel many mixed emotions about my current status as an entrepreneur.

Some of the emotions I felt include:


I had no idea how many awesome entrepreneurs attended NYU, and I felt a great sense of pride to have attended the same university. Jack Dorsey of Twitter and Square fame, Herb Kelleher from Southwest Airlines, Founder and CEO of the Ladders Alex Douzet, NYC’s Chief Digital Officer Rachel Sterne Haot, and Dan Porter of OMGPOP / Zynga were amazing keynote speakers and all NYU alumni. In addition, I met and learned from so many other NYU alumni who are working on some great startups.

I also felt a strong sense of pride about the entrepreneurial community that is being built at NYU by Frank Rimalovski and his team. The collaboration between staff, faculty and students was amazing and is sure to continue to grow the NYU entrepreneurship community in the future.


As an entrepreneur, you’re doing something wrong if you speak with a founder about his or her company and don’t get motivated to start or continue to build your own. The passion that founders have for their companies is contagious, and trading ideas and opinions with them only got me more psyched up to figure out what my next startup adventure will be.


Yes, I was completely motivated by speaking to other entrepreneurs, but it also caused a level of anxiety for me, since I’m not currently working on a startup that I can call my own. I quit my full-time job eight months ago to work on Dokkit and basically have gotten nowhere in the startup world. I’ve really lacked a startup identity, which has been eating away at me for a while now, so hearing that other founders have launched products, raised money, and garnered revenue made me feel really anxious and doubt myself and my decisions.


But overall, I felt a real sense of excitement by attending the conference. I’m excited to get to work on my next startup (whatever that will be), excited to grow the new relationships that resulted from the festival, and excited to be a continuing part of the NYU entrepreneurship community (as much as I can from here in DC).

The NYU Entrepreneurs Festival was an amazing event and I’m so happy I attended. Props go to everyone involved in organizing the conference, and I’m really proud to be a part of the amazing things happening at my alma mater.

Lessons Learned from Startup Weekend NEXT

This past Saturday, I completed Startup Weekend NEXT, which is an in-person class that teaches Steve Blank’s process of Customer Development. Twenty-three other entrepreneurs and I met with our teacher, Eric Koester of Zaarly, and other organizers, advisors, and mentors every Wednesday and Saturday over the last three weeks to learn how to “get out of the building” and talk to potential customers before starting to build a product.

This was an amazing but grueling experience which is awesomely summed up by Eric in this blog post. Over the last three weeks, my partner Wight and I spoke to over 60 potential customers and learned a lot about the process and ourselves. In addition to the lessons learned that Eric wrote about, I’ll add a couple more:

  1. You need a lot of empathy during this process. First, I had to understand how my partner worked and what his thought process was. Then I needed to put myself in my interviewees’ shoes to understand how they would comprehend the questions that I asked, to ensure I’ll get valuable feedback without leading them. Finally, I had to empathize with my fellow students to understand their points of view to provide feedback about their projects. I can think of a couple of times when I wasn’t quite empathetic enough during the process and therefore didn’t perform optimally.
  2. Passion is an absolute must in the startup game.  Because starting and building a company is such a grind, you have to be passionate about what you’re doing. Part of the reason I took this class was to test the passion that I had for the idea I was working on. I found that I didn’t share the high level of passion that my partner had, so we decided to part ways. If you don’t have a passion for the startup you’re working on, there’s little chance for success.
  3. Change is good. People learned a lot about how they should change their potential businesses, but I think the most impressive part of this class was seeing people actually change themselves. There were people who were initially timid and afraid of talking to customers who blossomed into outgoing, customer-development junkies. There were also people, like me, confident in their people skills who became really humbled by how difficult this process can be. Everyone had something to learn and it was amazing to see such an immense amount of change over only three weeks.
  4. Eric Koester has really cool socks! If you know Eric, you know what I mean. And I’m gonna get me some cool socks, too.

This class was an amazing journey and I’ll definitely use what I’ve learned in my future endeavors. I’d like to thank Eric, Mack, Denis, Barbara, all of the mentors and advisors, and most notably all of my fellow students for a great experience.

Now let’s get out of the building and do something great.

Move Fast, Move Slow

I think there are situations in work and life where you should move fast and others where you should take it slow (or “quickly” and “slowly” if you want to be grammatically correct). My sometimes conflicting thoughts are below.

Things to do fast:

  1. Workout / run – fast, meaning “high intensity” – it’s more effective and you get it over with quickly. Double win!
  2. Things that aren’t imperative to your goal – you should consider outsourcing or not doing these things at all.
  3. Think – Malcolm Gladwell has some things to say about this.
  4. Address a problem – nip it in the bud and move on.
  5. Live life – you only live once (#YOLO!), make it worth it, no regrets.

Things to do slow:

  1. Eat – enjoy your food. I am terrible at this.
  2. Write a note to someone important to you – be thoughtful and check your speling 🙂
  3. Think (when it comes to analysis and numbers) – you can get lost quickly, and a decimal point in the wrong spot can be disastrous!
  4. Hire – my shortcomings on this here. Take it slow and make sure the fit is right.
  5. Find your soulmate – again, take it slow and make sure the fit is right. Don’t settle. It took me eight (!) years to realize who my soulmate is and I couldn’t be happier.
  6. Live life – it takes time to find happiness and/or satisfaction. Enjoy the ride.

What else can you add to these lists?

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.