Hi, I'm Derek

An Entrepreneurial Revolution

It really is incredible how commonplace new business mindsets are becoming. I think a jaded young population and relatively unattractive traditional investment market are hugely impacting the way Americans think about capitalism.

I believe that we will look back at this decade as the beginning of an economic revolution as important as the scientific revolution in the 16th century and the industrial revolution in the 18th century. We’re standing at the beginning of the entrepreneurial revolution. This doesn’t mean just more technology stuff, though we’ll get that. This is a revolution that will permanently reshape business as we know it and more importantly, change the quality of life across the entire planet for all who come after us.

via When It’s Darkest Men See the Stars « Steve Blank.

Written by dshan on December 1, 2010

This Monday As A Monday

Sleep at two am because I still can’t breath 100% and sleeping when you’re breathing out of a straw isn’t even really sleeping and it definitely doesn’t come easy.

Wake up at seven in a deep sweat and almost no idea what day it might be or what time it is or what that goddamn blaring, oh…my alarm. Time for today.  Feeling robbed of some post-sickness sleeping.

Strategy meeting first thing, maybe push it back…got a pitch prep session at nine thirty…every day this week.

No time for a shower, out the door hoping I’d get a minute at some point to sneak up to the fitness center I joined for the winter. I rounded corner to a bus pulling away. Oddly another rolled up a minute later and I sat in the back where this woman carefully applied her makeup as we rolled into downtown and for a moment I remember thinking I was pretty happy to not be worried about some things.

As I write it’s around eight pm and I’m headed to North Vancouver in an hour to pick up a generously donated dresser from Maura and Danny.

Home by ten or so?

Yeah no workout.

Investor pitches coming together alongside a day full of annoying delays on a video I needed done today and literally just finished. Early afternoon conference call about a nationwide social media campaign we got involved in through the end of the year. Explained the value of twitter, outlined strategies.  Missed lunch.

Every spare moment in the office is about tomorrow and our company and its people and its impact and its dream.

Took a walk around the block mid afternoon so I wouldn’t throw my laptop through a window, wouldn’t overanalyze things, wouldn’t starve…wouldn’t someday look back on this day and this time and wonder where the hell it all went.

Wishing I’d showered at the moment, honestly.

How was your day?

Tell me good things.

Written by dshan on October 18, 2010

Work On Something Cool

You find yourself in the middle of a day that’s a month after the one you last remember.

You want to have written every minute of it, but instead you look around and wonder what you might do to further the cause you’ve jumped on board with.

That’s the best part of working on something you care about.  It’s also bad for your personal blog.

No, that isn’t an apology.

I spent a lot of time in the years after I graduated from college wondering what real people did with their lives.  I looked at the routes society mandates as advisable and found most of them completely foreign to the way I operate.

So I tried a few things.

I tried working for a lawyer doing deals in Hollywood and pondered the potential of a life as an intellectual property attorney.  Flights to LA for movie set duty and daily check ups on the industry news in Variety.

I took the LSAT twice and that second time I killed it like oil killed the Gulf of Mexico.

Before I got my scores back I heard the sing song everyone in the industry offered as advice: we hate this work.  I worked for people I saw gripping smoke and coffee breaks like their day would explode without them.  I saw the promise that going postal would provide wickedly smart people locked up in the depression afforded to the unfortunate and well-meaning people who settle for the restrictions of a typical career in a typical industry that pay a typically great salary for being typical.

Out I went, chasing the promise of an entrepreneurial environment in an identically typical industry.

Where I learned the hardest lesson I’ve learned: working for yourself isn’t the promised land.

Working for yourself isn’t the same as working on something you love working on.

So I failed at a long term and scalable business effort in a field that didn’t make me happy.

Big surprise there.

Today I’m in the office at the heart of a truly gorgeous city pretty damn late on a Friday night, and I feel like working.

I feel like working.

Hours and hours after I’d ever have imagined working on anything remotely related to work at any point in the years that came before 2010.

It ain’t easy.  I’ve told a lot of you that.

Take it from me though; life’s work and work’s life.  You are both.

Make ’em jive.

Work on something cool. Do it in the morning or night or lunchbreaks or whatever.  Just do it.

Then tell everyone about it.

What are you doing that’s cool?  I truly want to know.

Written by dshan on May 28, 2010

Stop And Take It In

I spend a significant amount of time in coffee shops.

Usually at least one day a weekend is spent in a window seat at one shop or another keypunching out blog posts or some project involved with foodtree or 20SB.  Weekends feel like borrowed time even though they really aren’t in this world.

I typically even spend a weekday in the coffee shop just below our office hammering away at my t0-do list; I think a room full of chatting strangers inspires productivity in me, in a lot of the same ways that an audience inspires me to keep blogging.

The coffee shop culture is completely unique, with only slight variations across different shops.

The employee’s play a big role in that, alongside plugs and refill deals and food quality.  In the right kind of shop, I can easily do a ten hour stint.  In those kinds of shops, I’m often not alone in those marathons.

Today I spent the first half of the day downstairs seated at the window as the weather moved from grey to grey-yellow and the rain made a half-hearted appearance.  The shop was full almost all morning; more conversation than laptop dates, and across the street the park revealed today’s importance to a particular subculture as kids strolled around sporting pot leaf necklaces and tie-dyed shirts.

An old man sat down next to me with a medium coffee cup and the newspaper.  At the window there are only tall stools and a high bench-like counter, where I had my laptop and he set his paper.

A few minutes later I felt the presence of stillness all of a sudden.

In the way that in a room full of caffeine, music, and conversation one could easily blend in to the fabric of a room, this otherwise unremarkable man was impossible not to stop and notice.

He sat there, hand on his coffee cup, staring out the window with a smile on his face.

He remained that way, just a foot or two from me, as I stole one glance after another.  Never moving and never breaking his gaze.

His smile wasn’t absent-minded and it wasn’t deliberate.  Sometimes we smile to hide.  And sometimes we smile because we can’t help it.

The genuine pleasure in his eyes painted a clear picture of content.

He had nowhere to be.

He sat there for nearly twenty minutes, quietly sipping his coffee and gazing out the window into a world moving all around him, fully bright and calm.

All I could think was, man…that’s what you want.

Written by dshan on April 20, 2010

Startup Social Life, Missing

When you make a decision to leave the world you’ve been in for any significant amount of time, you’re making a whole slew of decisions at once.

The purely locational decision is one.

Assuming there’s a professional component, that’s another.

The hardest one is realized in retrospect, when you find yourself at the tail end of all the large and little stuff that needs to happen to get you to your new location and your new life and new responsbilities.

That one’s the social one.

If you’ve been in the town you’re sitting in for a while, I’m talking to you from the other side.  I’m offering some feedback from the other side where the grass might be greener.

The friends you have are more than their roles as players in the experience you have every day.  They are more than who showed up at the bar or house party and who didn’t.  They are more than their love life drama and obvious shortcomings when it comes to showing up on time or really listening when you bitch about your boss.

They are more than the shared meals and concerts and shoulder to cry on…they’re more than the good and the bad stuff all added up.

They are the driving force in the web of life that’s making you who you are, where you are.

Those people are everything that goes into your sense of support and well-being, and their role is as integral to your happiness as the things you think you do for yourself which might be reproduced no matter where in the world you found yourself.

Your solo bike rides and Saturday morning coffee and dedicated Sex In The City rerun marathons all happen in the context of the access you have to the people who make up your immediate world, which quite frankly does not include anyone who isn’t there.

Proximity is an amazing thing because we tend to underweight it as motivated worldly citizens who want as much out of life as we can wrap our head and hearts around.  I’m not here telling you that I regret moving to Vancouver and I’m certainly not telling you to forgo your dreams, but I am telling you that before you go you should notice something; the proximity you have right now to your people is inherent to the pace at which your heart beats.

I left my home, and I did so to recognize something I decided to trust; my potential was closely linked to the person I am around people who are smarter than me and in situations that make me slightly uncomfortable.  Having felt underutilized and headed towards a mediocre version of myself, I followed an opportunity that I knew would put me in those two circumstances.

That’s a longer conversation, but it’s hugely based on my perception of the best decisions I’ve made in my life.  Each one was a decision to play with better players for stakes I didn’t consider easily attainable.

To uproot a life on those merits inherently under-weights the role your heartfelt relationships deserve in most of your major decisions.  I was an hour from my parents and a walk from my best friends. I was awash in a sea of wonderful people doing incredible things…make no mistake.  Some of the smartest people I know were the ones I spent my free time with each weekend in Chicago.

But my shot at big things happened a different way, and it forced me to sacrifice something dear to the person I think everyone reading this probably knows (or can tell) that I am.

And all I can offer is that it’s very, very hard sometimes.

It’s something you should look around and appreciate, because you have so much more than you realize.

Even when you’re alone.

Written by dshan on April 13, 2010

What Love Taught You About Work

I just dug up this post from my unfinished drafts, nearly a year ago.  I may have posted it; I honestly have no idea.  Either way, I chopped out 500 words, and thought I’d share.

Every day you work, you’re learning to be a better lover.

Every day you love, you’re equipping yourself professionally.

The two are quite common experiences.  It might be useful to consider them in harmony.

Actions and Words

Love is undoubtedly proven through the things that you do, as opposed to the things you might say.

Empty words and broken promises leave an enormous impact on lovers, co-workers, customers and clients.

People will always prioritize their most reliable relationships; we date the most attentive and trustworthy, and we’re loyal to affectionate professional relationships.

Ideas aren’t enough these days.  Execute.

Are you talking about what you’ll do with your life, or are you doing something to make it happen?

The First Date

A first impression portrays possibility.

Trust is a product of transparency, connection, and honesty.  Your quirks, nuances, oddities, and uniqueness fuel the strength of your strongest relationships.  Embrace them with friends and lovers.  Leverage them in your professional life.

At work, you should be repeatedly seeking second dates.  Although, if a relationship is toxic, inappropriate, or simply not going anywhere, it’s time to break up.

Do you treat your pursuit of purpose as if you want a second date?

Time In The Trenches

Falling in love is a product of perseverance and commitment.  Your approach to love changes drastically as you mature.  Your personal relationships mature through a process of learning and patience.

When it comes to love, you never skip the part where you learn your way around someone.

As we work, our ambition can preempt that diligence.

You’re likely surrounded by resources and experience.  Your career will stand on your ability to absorb wisdom, insight and feedback.

Are you in touch with your inexperience?  Do you seek out guidance and expertise?

Community Matters

The community around your love life is vast, and has a significant impact on friendships and romance.

We’ve learned to be hyper-conscious of our social circles.  The rewards it offers are endless; community, support, friendship, and fun.

The perils it can deliver in the face of dishonesty or selfishness are hard-learned, never forgotten.

Your pursuit of purpose involves a similar community.  In many cases, this community is significantly larger than your social circle.

You are being interpreted and assessed by that group nearly constantly these days, so stand tall, take the higher ground, and offer value.  Distribute respect and support.

Lead by example, because people are looking to be lead.

Better Yourself

The strongest relationships are between people who make one another better versions of themselves.  Great relationships value individuality as opposed to over-dependence.

Produce something valuable to your field.  Engage thought leaders.

Take on projects that interest you.  Create.

You don’t have to be at a startup to invent, launch, or develop new and exciting ideas.

Just trying will usually spice up your relationships.

You Don’t Know Everything

Take what you do know, and apply it to what you don’t.

We typically learn about love a lot earlier than we learn about work.

Love is work.

Work is about relationships.

You may not know everything, but between the two you know quite a bit.

Written by dshan on March 31, 2010

Generation BlahBlah

I’m not holier than thou, or anyone for that matter.  I haven’t made it, by any measure, as a writer or a professional.*  I was really good at soccer a long time ago…that’s totally irrelevant to this post, but I will be honest when I think I have a measure of authority.

This was deliberately written before I’d caught up on any of your blogs, going back months.  It’s not directed at anyone in particular, at all. It’s loosely influenced by conversations at SXSWi, but also in the way that I everyone I met there (and in reflection, everyone I have met from the net in general) to be such inspiring and smart people.

I’m probably wrong about all this, honestly.  I don’t consider myself to be “in the audience” of the content that I’m addressing, which is probably enough to just write this off and go have a cup of tea.

But my gut is telling me that there are a lot of people out there focused on describing, quantifying, and motivating Generation Y, and they’re misplacing their talent and time.

Gen Y Is Bored With Gen Y

Maybe it’s just that I’m 30, but this talk around Generation Y was not around while I was in my early and mid-twenties, and that was fine.

I wouldn’t have read it then anyway, and if I had I think once I’d made it to 30 or so I’d have wondered whether “live the dream or bust” or “respect our uniqueness” or “the new work/life balance or lack thereof” really made much of a difference as to where I ended up.

More and more Gen Y’ers are getting comfortable with their post-college lives and I think we can all move on now.  It feels as if our collective voice is just repeating “blah blah blah blah“.

We’re Really Not That Different

Sure, we’re a bit** more agile with technology, but everyone else is catching up fast.  Sure, that’s given us a bit of a unique profile when it comes to brands that want to sell us things and employers who want to keep us happy, but that’s their rat race.

You’re still buying things, and you probably work for someone.

Age Is Irrelevant

For the few years while young adults aren’t ready to take life by the balls and make it their own, some “we’re all in this together” stewardship can be helpful.

Then we all grow up and have real problems, and require real thought leadership that tackles the challenges that life indefinitely keeps throwing at you.  You are all the people who need to start thinking about this stuff and doing so without considering age.

We’re tackling these challenges lot later than our previous generations, and don’t think for a second that the world’s going to reward us for it.

Thought Leadership Is Action

This is more a message for the brilliant writers I think are wasting their talent writing about Generation Y; color commentating our segment of the population is and could continue to be a great way to build an audience and make a life of it.  If that’s your goal, I step back.  I hope to say I knew the Voice of Generation Y when I’m 80 and looking back.

My concern is that I think a lot of you have bigger plans…you want to make real-life differences for people…you want to tangibly lead people and companies into an exciting future; I think you should start doing that.

Aligning yourself with a generation makes you a Narrator.  You’re talented enough to be a Novelist.

It’s The Same Amount Of Work

In my mind, there’s a reason that leaders like Gary Vaynerchuk, Seth Godin, Chris Guillebeau, Gwen Bell, Tim Ferris, Brian Solis, or whomever else floats your boat seem so innovative and sharp. They’re trying to push an envelope that’s not tied to an age group.

It’s interesting because if you’re in their wagon, they’re trying to push that wagon up a mountain.  They’re tackling a piece of life…not the process of life.

Both endeavors take lots of work. Being a leader, thought leader, author, blogger…it’s all a lot of goddamn work.  All of those people work really, really hard.  (They party hard too, by the way.)

A note as well; I mention these big wigs because I very honestly think a number of you guys could join them.  I think you are incredibly talented and smart people. I wouldn’t have wasted nearly a thousand words on this if I didn’t.

Stop The BlahBlah

I think the rhetoric has reached a bit of a stand-still and thoughts are being regurgitated.  The Generation Y Writing Movement has plateaued. Call me wrong…I very well could be.

My feeling, for what it’s worth, is that the buck needs to stop.  If what you’re saying or doing needs to be qualified with a Gen Label than rework it.  Think about it differently. Take it out of the age context and find what’s really interesting.

Stop the BlahBlah and get to the meat of the issues. You can see the meat, and that’s what makes you different.

That’s your edge.

Soon the everyone else will figure it out.  Soon, they’ll see the same world you see.

And they won’t give a rat’s rear end who you are anymore.


Image by Mike Baird.

I hope that my respect for all of you, anyone who’s blogging in fact, is obvious in this post and elsewhere around the web.  If we’ve met or meet, I hope that’s clear in person.  If I’ve offended anyone at all, please don’t hesitate to email me and tell me, because I will attempt to rectify it.

*You show me a 50 year old who’s never heard of twitter and I’ll show you a 28 year old who doesn’t know how to use it.

**I work for “myself”, which some might offer up as evidence of success.  What that really means is that I have very little money and hope to heaven that what I’m working on works out.  I’m writing this having spent a pretty sizable nest egg to end up with almost nothing a few months ago.  I’m writing this with almost nothing to point at to say, “Hey, I know what I’m talking about.”  You might suggest that my experience with 20 Something Bloggers gives me a measure of credibility, but I’d argue that I didn’t make it was it is…I just try to make it better.

Written by dshan on March 23, 2010

We’re All Idiots

I came to Vancouver without a place to live.

The time leading up to the decision to pursue an uncertain life, in another country no less, was not a lot of time.  It didn’t leave much wiggle room.

In fact, it basically wasn’t enough time to make any real decisions.  It meant saying goodbye to my closest friends, my family, and the massive network I’d built up around Chicago could barely even happen.   It wasn’t the kind of thing most people would probably accept as a phase in their adult experience.

I’m fairly confident means that that I’m crazy, and I’ll look back on the whole experience and wonder what lead to my being the kind of guy who would move to a foreign country without a work permit, a place to live, or enough time to really say goodbye to friends and family.

I’ll wonder, but I won’t really doubt the decision.

I don’t say that because I’m sure that things will work out.  I just say that because I know that even if I decide that I could have done things differently, it won’t be because I made the decision I made; to come here and take a shot at doing something really significant.

Yeah…you do things like that because you think you’re right.

You think you’ll look back on it and look like an idiot savant.

And failure means the ‘savant’ part gets tossed.

So you work hard, and hope that a savant you remain.

It’s as good a reason to work as any, I suppose.

What are you working for?

Written by dshan on February 17, 2010

On An Island

There’s something about the kinds of changes I’ve been through lately that make me feel as if I’m on an island.

I want to assure you that this isn’t some emo blog post about being lonely, and I’m pretty sure it won’t even contain a Lost reference.*

Back in about June, I had lunch with Anthony and we subsequently started spending time with an idea that became foodtree.

I have no clue as to whether any of my old colleagues are reading this, but I want to make sure it’s clear that that doesn’t mean I’d started checking out of the financial industry.  Last Summer and this past Fall, I worked extremely hard to push my practice forward.  I’ve always been a project guy, and 20 Something Bloggers is testament to that; I spend a lot of my free time getting involved in things.

Anyway, it’s almost impossible to illustrate how quickly things changed at the end of last year, and I think that’s partly because it was often in ways that made writing about it here inappropriate.

Hell, making any claim as to what might happen in the context of something like foodtree would have been (and still would be) outright irresponsible.  We’re a startup, and every day’s a blessing even now.

As a blogger, though, I’ve spent a lot of my written words pushing for a few common endeavors within the community.  One of them is transparency; I think blogging is at it’s best when we try to be concise and honest.  The other is confidence; I think personal bloggers write themselves towards a voice that represents them, and the more they write the closer we all get to the good stuff.

Yet for months now I’ve left a lot out, and I’ve quite obviously written far less than at any point in recent memory.  If you know me in person, I’ve probably complained about this more than once over a beer.   The most uncomfortable thing I think I’ve dealt with through this process is censorship.  Initiated by me, no less.

(The second most uncomfortable thing I’ve dealt with would be an overdrafted bank account.  Sidenote.)

I feel as if I find myself on an island.

I feel that way because I can’t think of anyone in my life who could honestly answer this question:

“So…how the f*ck did you get where you are right now?”

Which makes for quite a lot of filling in, I suppose.

*Don’t get me started on Lost.  Don’t get me started on being on the West Coast where things happen later, and Lost.  Don’t get me started on Canada, and Lost.

Written by dshan on February 10, 2010

Oh, Canada

I was beginning to doubt my odds of getting a work visa in Canada.

My two week provisional visitor’s visa was almost up.  I’d spent all week locking down my very digital and very public life, and reassuring most of my friends and family at home that I was not, in fact, totally insane.  I felt as if the whole bureaucratic ineptitude of a nation had decided to throw a tea party at my expense.  I was in Canada, but I wasn’t allowed to work…much less build a company from scratch.

It was Friday, and I was cellbound come Monday.

Quick decisions are a part of life, and as daylight ticked away late Friday afternoon I decided to make the best of the situation and snap up an inappropriately inexpensive flight from Vancouver to Chicago the following morning.  Bust out of town…come back three days later and try a novel approach.

So yeah, I bought a plane ticket at about 7pm, and got on a 7am flight to Chicago.

I arrived in Chicago at about 7pm last Saturday.

Recently I gave a Best Man speech (posted here) at the wedding of one of my oldest and best friends.  The move to Vancouver injected a lot of emotion into that wedding weekend, and into the few weeks that followed. Murph and I always seemed to end up in the same place, so my leaving was a big deal.

So when I arrived in Chicago that evening, with the help of Braden and my sister I made my way to the bar downtown in which I knew that Murph’s wife, Ash, had planned on throwing him a surprise 30th birthday party.

Have you ever seen a surprise party get surprised?

It was maybe an hour after his friend’s and family had yelled, “Surprise!” in this private funky room in the basement of this place, and just one of them (his lovely wife, of course), knew that there was more to come.  I remember nearly buzzing as I ran down the stairs and walked into the room; our friends, his family, and then he turned and nearly sh#t his pants.  It was magic.

As I’m sure you can imagine, the party was really great, and the chance to catch people so quickly after I’d run out of town in the midst of my first (and somewhat frantic) move was refreshing.  I hadn’t been gone long, no doubt, but to really get another goodbye was heartwarming.

I spent most of the weekend with my family, and headed back to Vancouver Tuesday, with no clue as to where I’d actually end up.

This time around I had an application for a work visa and a bunch of supporting documents, including my original diploma from Stanford and a job offer letter from our CEO (snap!).

I was entirely unsure as to what I’d face when I walked up to the same customs line and told them I intended to work.  I had no idea if they’d pull up a record of my first experience, and begin the conversation from Skeptic Island.

I had no idea if they were following me on Twitter; I sure wasn’t risking it, though.

Approaching the customs area, though, had quickly become a very friendly place, with the city putting on a smile for its influx of Olympic attendees.

I was politely instructed that New Workers had their own line, and I proceeded to a back room (I’ve now seen all the back rooms in that airport, I’d imagine) where I came upon a very, very cute customs agent who is now also responsible for making my life infinitely easier.

Two or three questions and bam: a year-long work visa.  Thank you very much.

No…I didn’t ask her out.

I got the hell out of there.

Photo by me; that’s Rafe, Anthony‘s son.

Written by dshan on February 8, 2010