Hi, I'm Derek

Why Google Can’t Build Instagram

The startup will always have a place in the ecosystem.

The exec I was talking with said Google Wave had more than 30 people on the team. He had done his own startup and knew the man-month myth. For every person you add to a team, he said, iteration speed goes down. He told me a story of how Larry Ellison actually got efficiencies from teams. If a team wasn’t productive, he’d come every couple of weeks and say “let me help you out.” What did he do? He took away another person until the team started shipping and stopped having unproductive meetings.

via Why Google can’t build Instagram — Scobleizer.

Written by dshan on November 12, 2010

Scale Goodness

But the best thing you can do for the green effort is to scale. If your business is essentially different from your competitors' because you have an element of green in it, that's good. But what would be great is if you figured out how to scale green.

In business, the greatest challenge is to scale without diluting too much the very essence of your core idea. Walmart scaled cheap value for suburbia. McDonald's scaled consistent quality fast food. Starbucks scaled expensive coffee in a luxury environment. By scaling, these organizations spread their ideas all over the place and changed the world.

If you can't figure out how to scale, you can't bring your core idea to the masses.

The greatest challenge today for aspiring green entrepreneurs is to scale.

via SAMBA Blog.

I’m extremely fortunate to witness the first batch of scalable businesses devoted to social good. I hope we’re one of them.

Written by dshan on September 16, 2010

A Day In The Life

My bus rolled lazily down the hill towards downtown with a crest of sunshine peeking over the city’s leering mountains gathering an unusually light crowd of early commuters and the usual mix of destitutes making their way to the intersection of Main and Hastings, effectively an open air flea market of drugs and addiction in full swing day and night.

The intersection is, quite frankly, total mayhem…no matter it be eight in morning or ten at night, and it serves as as stark reminder that the bottom is quite a lot further down the rabbit hole than anything I’ll ever experience.

It’s a useful reminder, actually.

The bus opened its doors at that corner and the addicts jumped off eagerly, as always. I gazed out at a decrepedly thin Asian man crouched against the building facing me, happily handing single cigarettes to two young men and a woman huddled around him. The two young men moved off and the women, in a loose yellow v-neck, torn jeans, and supported by one of those four-legged walkers, swayed back and forth while chatting and stashing her smoke in a back pocket.  She was war-torn, to the point at which you could almost believe that the walker wasn’t even medically related; it was simply that balance is a luxury no longer afforded to someone who has run that many chemicals through themselves.

When you see this section of town, you’ll understand that I thought very little of the scene.

My day was hectic, as a meeting-filled day tends to be.  When building a web product it’s hard to feel productive unless you’re nestled up to your computer.  For good or for bad I feel a deep sense of urgency about our website and product right now so my senses are probably heightened a bit, and I get tense when I’m not feeling as if I’m getting shit done.

As I moved from coffee with an exciting new prospective hire to strategy planning with Anthony  I felt as if the productive part of my day was rapidly escaping me.

It’s ludicrous, really, as we’re moving a lot of people and pieces towards our goals and improved product, but hey, it’s how I felt. I think anyone who’s faced important deadlines can relate to the way a priority list can loom in the corner pointing at you like the Evil Monkey in Chris’ closet.

I settled into the early evening catching up on email and Foodtree code development, hesitant to leave because it felt as if the day had just gotten started.  A poker game was beginning in the conference room next to our kitchen and entrepreneurs wandered the floor looking for a few more last minute players.  The sun, now setting, crawled at length across the floor, and a team building an application for the hockey community gathered around a whiteboard discussing revenue models.

This is the stuff of ideas in motion.

My focus was off and it was getting late, and I knew I should reengage my priority list at home.

I boarded my bus and sat with a blank stare out the window, mentally reshuffling work stuff with my jaw clenched tight.  Zoned, but still mentally locked into things that need doing.

Three busstops later I snapped into focus as a yellow streak caught my eye, and there she was.

The woman from twelve hours earlier was hobbling across the street out my window, a few blocks from where I’d noticed her before.  She was just moving down the sidewalk…her walker, then a step…deliberate.  Awkward and slow. She hunched forward and to the side…

The struggle of it…of a block-long stretch of sidewalk, seemed almost unfair.

What must her day have been like?

I imagined a day of detachment and pain, craving and confusion. Alleys and sidewalks. Bartering and hustling and a never-ending quest for self-destruction.

A city block transformed into a mile long  journey.

A day that seemed to have ended before it began suddenly became endless, right before my very eyes.

Written by dshan on August 13, 2010

Lemonade Stand Founders

Kids who start lemonade stands aren’t all that different than the guy who started Zynga or Google, although one could argue that a lemonade stand is a deliberate attempt to make a margin and starting something that’s useful for people before you even have a revenue model is deeper.

Thing is, I don’t think kids post up lemonade stands to make money, so much as they throw up lemonade stands to have people take a few minutes out of their day to recognize what they’re up to.

I think most lemonade stands are exercises in business education handed down from up high.

Lemonade stands are lesson plans.

But if you started a lemonade stand where people got something more than lemonade, those kids would be sitting in their plastic chairs on the corner of the neighborhood cul-de-sac selling more than lemonade, in order to sell lemonade.

The lemonade stand might be a place where you got points towards your influence on community politics, for instance.

You stop by and grab a fresh drink and you got yourself ahead in the running for the neighborhood mayorship.

Your mayorship meant you might represent your neighborhood at County Hall when they were deciding on where to build family-friendly parks.  The Mayor with the most points was carrying a lot more votes, and maybe that Mayor’s votes represented the overall participation that their neighborhood had delivered in the previous couple of months.

They had their points, which made them Mayor, but they’d need their neighborhood’s points to really have influence.

The whole community could empower their leaders to have a say in local government.

They could do that on their way to their important jobs that let them afford to live in their neighborhood.  They could do that knowing that two bucks at the corner was a way to be at City Hall on Tuesday night while they were travelling on business.

A lot more lemonade would get sold, I think.

A lot more kids would see the value of thinking about the world in an entrepreneurial way.

Why is it that only outcasts find themselves motivated to build things that disrupt our experience?

Something is wrong if removing yourself from the mainstream is a prerequisite for trying to change the world.

Written by dshan on June 6, 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

I’m A Founder, I’m At Bootup

Today, one of the guys I met as a fellow cohort founder when I arrived at Bootup Labs wrote a blog post that has started a wider conversation on some of the developments recently here at the accelerator.  I won’t recount that; you can find the story at Techcrunch, gigaOM, ReadWriteWeb, and others.  You can read the Bootup Labs piece here.

Jamie was one of the co-founders at a company called Status.ly and one of the accelerator cohort members I definitely got along with best.  Jamie and Daniel from Zedmo were two people I considered among my first friends here, and both remain friends following some of the unfortunate realities that blew through here recently.

Some of the original Bootup cohort members are no longer with us here, leaving behind Compass Engine, Summify, and my team at Foodtree.  The details around that unfortunate development are intimately tied to the difficulties present in today’s early round investment community, and I think if you poke through those articles and specifically the Bootup Labs official blog post, they’re pretty well covered.

In the process of closing a funding round, some concessions were made and the roster had to be shortened.  Those of us who remain are in office, and trying to make use of the resources we have here.

I suppose I’m writing to to share a bit of the perspective I have as someone who was a part of this process, and yet remains in Bootup Labs.  This is my personal blog, and not our company’s official blog, mind you.

I think it’s important to note that everyone involved, both founders and Bootup, did their best to deal with the challenges that presented themselves and lead to what happened.  We were all frustrated when it looked as if the funding round was in jeopardy; having worked in finance and investments I wasn’t surprised that things like that could change quickly, but nevertheless I made the same sacrifices that Jamie made.

I sold my stuff.  I emptied my bank account. I came here with very little in my pocket and I have spent my bank account dry more than once since January.  I flew to Vancouver with two bags, and I am living out of them.

I did that knowing full well that the financing was contingent. That was a risk I was willing to take.

All of that aside, I had no expectations of an easy road, and I quickly dispelled any expectation of seed investment from Bootup.  Our team had (high) hopes that we’d be able to avoid Bootup’s capital component, the details of which have been a bit misconstrued around the web, but don’t add a whole lot to the discussion.  Even when Bootup’s capital line became our most attractive potential source of capital (after we already knew the funding round was in jeopardy), we worked under the assumption that chickens aren’t counted before they hatch.

I don’t mean to suggest that Jamie counted chickens, and I sure as heck don’t intend to undermine any of Jamie’s thoughts or opinions.  I mean, I moved here knowing three people, and the people I met at Bootup were my social circle; losing those four teams was painful.  It was devastating for all the companies – and the companies no longer here are dealing with the resulting challenges.  I don’t wish that on people I consider friends and have a huge amount of respect for.

The companies who are still here have our own challenges.  We’re all working day and night to build exciting products and traction.  We are learning more every day and we’re mindful of the experiences we’ve had so far.  Nothing is guaranteed.  We are fully responsible for making this work.

And there aren’t hard feelings around here…as I write this post there are members of Zedmo and Blastramp in our offices, plugging in and getting sh*t done.  I keep in touch with Jamie and hope to see him again.

If anyone out there has questions about this situation or even what it’s been like to launch a startup in a world that throws you curve balls, please feel free to reach out.  Comment here, hit me up on Twitter, or shoot me an email.  Speculation doesn’t carry any real value these days…I’m a firm believer that transparency is paramount.

Written by dshan on April 15, 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