Inside My Brain

Thoughts about startups, tech, marketing, and life

CATEGORY: Careers

Guest blog post for CEA – How I Came to the Decision to Quit My Job and Become an Entrepreneur

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Hi All!

As I mentioned before, I am guest-blogging for the Consumer Electronics Association (CEA) about entrepreneurship and startups.

My first post highlighted my journey to entrepreneurship and how there’s no one path to becoming an entrepreneur.

My most recent post takes you through my decision process of quitting my job with the Washington Capitals and taking the leap to launch a startup.

I hope you enjoy!

Like this post? Then follow me on Twitter at @mikewchan, connect with me on LinkedIn, and add me to your Google+ circles for future updates.

My first guest blog post for CEA – My Path to Entrepreneurship

I’m proud to announce that I’ll be guest-blogging for the Consumer Electronics Association (CEA) about entrepreneurship and startups! I’ll write about my ups and downs, lessons learned, and any other experiences as an entrepreneur.

Check out my first post where I talk about my journey to entrepreneurship and how there’s no one path to becoming an entrepreneur. I hope you like this article, and stay tuned for the rest of the series!

I’d like to thank Sean Parker, Jamie Carracher, and Lindsay Bianco at CEA for this opportunity.

Enjoy!

Like this post? Then follow me on Twitter at @mikewchan, connect with me on LinkedIn, and add me to your Google+ circles for future updates.

My First Year of Entrepreneurship – What I Think and What I’ve Learned

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Just over a year ago, I left my job at the Washington Capitals to become an entrepreneur. It’s been a valuable learning experience and a great ride, but like any other job, there have been ups and downs. I wrote a post last August about what I learned after one month on my own, and this article augments those thoughts.

While I’ve learned a ton over the past year, I think I’ve broken even in terms of progress. In the corporate world, that’s unacceptable. In the entrepreneurship and startup worlds, depending on the situation, it may be a bit more common. Regardless, it’s kinda depressing.

Consulting

On one hand, the independent consulting work I’ve been doing has been going really well. I currently have three core, long-term clients for which I hope I’m doing a good job and we’re making solid progress toward our goals. I’ve also successfully executed two other short-term projects. Additionally, I have a couple of other potential clients in the pipeline. The best part is that all of these clients and projects have come through referrals, with no formal sales or business development processes. I can’t complain one bit about my consulting work.

Startup Stuff

But consulting is not why I became an entrepreneur. I want to build a technology startup, and on that front, I haven’t done much at all.

I wrote about what happened with my first startup, Dokkit. Since then, I’ve made only a little progress in my second at-bat. But a big takeaway I learned was that ideally, the startup team should come first, then the idea (for other opinions on this, see here and here). I am working with a couple of developers on a startup, and one of the team members is a consulting client of mine, so we know how each other functions and work really well together. We’ve thrown around a ton of ideas but haven’t been able to agree with one that we all want to execute. This process can be really frustrating, but I think the hardest part, assembling a founding team that you know you can work well with, is out of the way. We’re taking our time with developing the concept and being really diligent about pursuing an idea that we’re all passionate about and has the potential to be a real business. Though it’s moving slowly, I think we’re going about it the right way.

An exciting endeavor I’m involved in is volunteering as an Up Global (formerly Startup Weekend) DC Organizer, where I coordinate events and workshops that help entrepreneurs get their companies off the ground, learn about startup frameworks and resources, and connect with fellow entrepreneurs. I’ve only been doing this for a few months but it has allowed me to give back to the DC entrepreneurship community and meet many smart, talented, and driven entrepreneurs who may build the next great company.

Overall, there’s been a lot of activity but not so much progress. I’m working to change that.

The Struggle

Yeah, I’m going through ups and downs, but I’m not yet going through The Struggle. The Struggle sounds horrendous, but part of me wants to feel that stress and have that kind of responsibility. I am lucky to be in the situation I’m in – I have a really supportive wife, family, and friends and stable consulting work – but those blessings may be hiding the urgency that many startup entrepreneurs face that forces them to move at 100 miles per hour and really get shit done. Don’t get me wrong, I count my blessings everyday, but sometimes wonder about the other ways they impact my work.

One year in, it’s been an amazing ride so far. But I stress out everyday thinking that I’m not moving fast enough, learning enough, or making enough progress. Regardless, I wouldn’t change a thing. And when I write another post like this in a year, hopefully I’ll have a lot more to say about the technology company I’m building.

How Does Confidence Affect You?

confidenceIt affects me a lot, in a few parts of my life. For me, confidence is many times linked to motivation, and they both impact my performance. Here are a couple of examples.

Confidence in Sports

You hear the word “confidence” thrown around a lot when people talk about pro athletes and sports teams. Sportscasters and analysts will say things like, “He’s playing with a lot of confidence” and “They have a lot of momentum and confidence heading into the playoffs.” Confidence is a completely intangible aspect but an important one nonetheless.

I play basketball twice a week but I’m not very good. I’m short, not as quick as I used to be, and can’t jump. But I do have a decent jump shot. And if I make my first couple of shots in a game, my confidence rises and I tend to shoot (and hopefully score) a bit more often.

But when I miss those early shots badly, I sometimes get into my own head and lose confidence in my shooting ability. I become more hesitant to fire and pass up shots that I’d normally take. Then I look like a worse player than I already am, and it just gets worse from there. It’s ugly.

Confidence at Work

Confidence affects me a lot at work, too. In the last ten months that I’ve been an entrepreneur, my confidence has been riding a roller coaster.

When I resigned from the Caps last July, my confidence was really high. I had a good five-year run and I left the Caps/Monumental Sports marketing department in better shape than when I joined. I was leaving to work on my startup, Dokkit, and I was so motivated to change the world. I also secured a couple of consulting contracts that allowed me to take the leap.

Just a few months later, Dokkit was no more, and my confidence tumbled. Dokkit was the primary reason why I left my awesome job at the Caps, and a lot of thoughts ran through my mind – anger, regret, disappointment, self-doubt, and a little bit of fear. I was lost for a while, unmotivated, and felt like I didn’t have much of an identity in the startup world. I did have some wins, as I completed a consulting engagement and scored another, which gave me a little bump. But in the larger scheme of things, it didn’t help much, as I wasn’t trying to build a consulting firm; I was trying to create a startup.

Forming a partnership with Thorn Technologies in December has been a real positive for me. Not only do I get to use my marketing skills to help Jeff grow his software development business, but we’re working together on a startup as well. I have clear deliverables and timelines (my confidence increases when I execute discrete tasks well), and I have a newfound identity in startup land. It’s been a great partnership so far, and one that has definitely helped me increase my confidence and motivation on a daily basis.

Still, everyday there are highs and lows. Some days are tougher than others, but that’s all part of the struggle.

Getting Out of the Rut

Things are easy when your confidence is peaking. It just feels like you’re smarter, things move more quickly, and you worry less about the little things.

But what about when you’re in the valley? Everything seems to move too slowly, every task is a bit more difficult, and you tend to stress more about insignificant things. Motivation drops, which then lowers your confidence even more. It’s a vicious cycle. How do you get out of that rut?

I try to add value in other ways. In my basketball situation, I’ll pass the ball a bit more and play better defense. When an easy shot opens up, I’ll try to take advantage of that to build my shooting confidence. At work, I’ll delve into a task that doesn’t take too much brainpower. Maybe I’ll take care of administrative work or write a personal blog post to get some things off my chest (like I’m doing now). Sometimes even those tasks are difficult but it helps me make a little bit of progress when I’m not at my best.

Does confidence impact you as much as it impacts me? If so, how do you take advantage of the peaks and deal with the valleys?

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?

Fear and Paranoia in the Workplace – Good and Bad

Paranoia imageThe other day I was instant messaging with one of my childhood friends and we landed on the topic of jobs. He’s good at what he does and has worked up to be a Director of Marketing at a major media company, yet he stated that that he was “completely paranoid that he wouldn’t be employable in 10 years” and that’s why he works harder than anyone at his company to ensure that this doesn’t happen.

I actually think this is a great frame of mind, if not taken too far. A little bit of self-inflicted fear and paranoia is a great motivator, and looking both over your shoulder and forward allows you to stay ahead of the pack. A bit of “I’m not/won’t be good enough” can motivate one to work harder and smarter to improve areas where he’s lacking.

But what I don’t condone is the use of fear and paranoia by managers and executives with their subordinates. It creates an unenjoyable workplace where employees become afraid to mess up with fear that they’ll suffer harsh consequences. I came across this article about how Scott Pioli, GM of the Kansas City Chiefs, created a culture of fear, paranoia, and secrecy to the point where Chiefs employees were worried about their phones being tapped. Check it out, it’s an interesting read.

I’m all for accountability, attention to detail, and integrity, but I think there are better ways to foster that culture. You can still be very results-oriented without scaring it into your employees. If you choose to use fear, chances are you won’t get the results you want. Just look at the Chiefs.

The Importance of Consistency

You could be a smart QB with a rocket arm who throws for 4000 yards and 40 TDs over the course of a season, but if you alternate between games of 350 yards/3 TDs and 150 yards/0 TDs, you’re likely not taking your team to the Super Bowl.

A TV show can be entertaining and deliver great ratings in a season, but if the show can’t replicate that success season after season, it’s going to lose viewers and won’t be on the air for long.

You could be a great marketer and run a great campaign for your product and service but if you’re not continually communicating with your customers and delivering value, you’ll likely lose them to your competitors.

Being good or smart once or twice isn’t enough to win. You have to deliver at a high level, all the time. Consistency is really, really important.

I hope that my blog posts are somewhat interesting and provoke some thoughts, but if I posted more often than once a month, I might have more than 30 readers. I’ll try to be more consistent. 🙂

My first blog post – kinda

Hey everyone! So this is kind of my first blog post.  I wrote one blog post a few years ago, but it was about absolutely nothing and I quit after that. I’m a different man with different interests now, and I think I am going to dedicate myself to blogging more than I did back then. Hopefully.

The main reason why I am starting this blog is because it’s a great outlet for self-expression. I work for the Washington Capitals, so my big boss is Ted Leonsis. If you didn’t know already, he wrote a book called The Business of Happiness (http://www.businessofhappinessbook.com/), and one of his tenets for being truly happy is having a method to express yourself.  For those of you who know me know that I have a lot to say, and this blog is going to be one of the channels I use to express myself. This blog will be similar to Ted’s and will be about a broad range of subjects. I consider Ted a role model and hope to be at least 1/10000 as successful as he is.

I think I am a man of many interesting interests and this blog is going to address them all. Here’s a little organized synopsis of myself:

Marketing, in sports and any industry

As I mentioned, I work for the Washington Capitals, and I am Director of Strategic Marketing there. I love my job, and in many ways, my job defines me. I like to think deeply about marketing, primarily in sports but across all industries, and am interested in CRM, social media, mobile marketing, advertising, sponsorship, research, and pretty much anything else that has to do with marketing. I also teach a course on Sports Digital Engagement at Georgetown University, which will fuel many of my thoughts on this topic. A lot of posts here will have to do with marketing and I hope we can get into some great discussions.

Sports in general

First and foremost I’m a sports fan.  This drove my journey into working in the sports industry. I am a big fan of the Yankees, Giants, Caps (not only because they pay me), and Georgia Tech. I also follow the NBA, tennis, action sports and poker (if you think that’s a sport), and a bunch of other sports I can’t think of right now. I hate the Boston Red Sox, by the way. The NCAA b-ball tourney is going on right now and I wish Gus Johnson called every game. He’s awesome. And I love fantasy sports, too. Except when my teams suck.

Poker

I like playing poker. I play online and wish I played live games with friends more. I make trips to Atlantic City and Vegas every now and then. I’ll eventually play in the World Series of Poker sometime during my life.

Food

Ask anyone – I am a great eater, in terms of volume and frequency. In my 3+ years in DC, I’ve eaten at more than 100 restaurants in the area. I’ve lived in NYC, San Francisco, Atlanta, spent some time in Phoenix, LA, and Boulder, CO, and have visited Chicago, Seattle, Philly, and a bunch of other cities, so  I’ve eaten at some great restaurants all over the country.  I like all food except for olives, for some strange reason. I’ll post some restaurant reviews here, and will probably start writing reviews on Yelp. Maybe. I’d love to hear more about your favorite restaurants.

I hope you enjoy my posts and that they provoke thoughts and dialogue.

On to the next one…