Introducing CriticallyIn

I’ve begun building a bunch of prototypes for ideas I have had over the last few years, each an experiment to see if my ideas have legs.  My goal is to turn one of these ideas into a business as soon as one is validated.  I’d like to tell you about the first of these experiments, CriticallyIn.

CriticallyIn let’s you create an event that requires a minimum RSVP in order for the event to take place.  There is a certain class of event that needs to hit critical mass in order for the experience to be enjoyable (think flash mobs, silent dance parties, protests, etc).  CriticallyIn was built to help plan and organize those such events.

I’m using CriticallyIn to plan my Bay to Breakers MC Hammer theme, along with gauge interest for a faux cycling celebration flash mob idea I have.

I’m not going to promote CriticallyIn that heavily, because at this point I’m solely interested in running an experiment and learning from the early users of the product.  If you plan an event or attend one, please let me know if you have any feedback or thoughts.  And while I’m here, feel free to fill out a survey for me here :).  Enjoy!

Mindfulness and Meditation Resources

I’ve received several requests for mindfulness and meditation resources.  I got into meditation several months ago, and it’s now a big part of my life.  Just like I look to running or cycling for physical training, mindfulness and meditation are great ways to relax and stretch our minds.

I spend most of my time listening to Dharma talks and following guided meditations.  Dharma talks are typically 60-minute talks that are about self, subjects ranging from fear to death to love and joy.

A huge repository of dharma talks are available here: dharmaseed.org.  Click on “talks” and either view the most recent talks (there’s an RSS feed, too), or search for things like “forgiveness” or “difficulty” or “love,” whatever you’re interested in hearing.  These are talks about life and self, and they’re very interesting perspectives.  They are not meditations.

There are good, free guided meditations at the UCLA Mindful Awareness Research Center.  Jack Kornfield has wonderful guided meditations for sale, too.  I very much enjoy meditations on loving kindness, forgiveness, breathing, awareness, joy, and working with difficulties.

What I tend to do is meditate 2-3 times per week, for anywhere from 5-45 minutes each.  I listen to a Dharma talks on the bus, car ride, or while working out.  The Dharma talks provide the perspective, and the meditations are like lifting mind weights that produce happiness instead of big muscles.

Finding Your Edge

I want to share a wonderful little story from Patricia Genoud-Feldman’s talk about learning from fear.  This story is about finding your edge:

There’s a story about a group of people climbing to the top of a mountain.  It turns out it’s pretty steep.  And as soon as they get to a certain height a couple of people look down, notice how far it is, and completely freeze.  They had come up against their edge and they couldn’t go beyond it.  Their fear was so great that they couldn’t move.

Other people tripped on ahead, laughing and talking.  But as the climb got steeper and more scary, more people became scared and froze, too.  All the way up this mountain there were places where people met their edge, froze, and couldn’t go any further.

The moral of the story is that it really doesn’t make any difference where you meet your edge.  Just meeting your edge is the point.  Life is a whole journey of meeting your edge again and again.  That’s where you’re challenged.  That’s where if you’re a person that wants to live, you start asking yourself questions, “Now, why am I so scared?”  ”What is it that I don’t want to see?”  ”Why can’t I go any further?”

The happy people who got to the top weren’t the heroes of the day.  They just weren’t afraid of heights.  They are going to meet their edge somewhere else.  The ones who froze at the bottom were not the losers.  They simply stopped first and so their lesson came earlier than the others.  However, sooner or later everybody meets his or her own edge.

It occurs to me that my love for adrenaline sports such as snowboarding, snowmobiling, skateboarding, and cycling is based on my desire to find my edge.  I love trying bigger, scarier things.  Even when I fall or get hurt, I love getting back up and trying again.

10 Facts About Working at a Startup vs. a Big Company

I’ve spent the last few weeks trying to recruit friends of mine to come work with me at my super early startup.  In doing so I’ve had to educate a lot of my friends on what it’s like to be at a startup, and why you might want to join one.  This blog post is a summary of all that advice.  Oddly enough, I wrote a similar blog post my senior year of college while interning at Redfin.  And since college I joined Cloudera before they were funded and left when the company closed its Series C, or third round of funding.  The advice below mostly comes from my experiences at Redfin and Cloudera.  I’ve also worked at Google and Northrop Grumman.

1) Responsibility, accountability, impact: at a startup it’s unavoidable to have lots of responsibility and accountability. There’s no doubt, too, that being at a startup will put you in a position to make a huge impact.  If you do amazing work the entire company and all of its customers will benefit from it.  And you’ll be loved for it.  You’ll get notes from the CEO and other leaders complimenting you on how awesome your work is.  On the flip side, if you make a big mistake, the whole company pays for it.  But keep in mind that most startup cultures prefer agility and speed to cautiousness.  It’s likely that your mistake won’t actually get you in trouble, as long as you were trying to do the right thing.

2) Risk: working at a startup is riskier.  The startup likely isn’t profitable, and probably only has at most 12-18 months worth of money in the bank (this is called the startup’s runway).  If the company does very well, the CEO will raise more money and extend the runway.  You’ll still have a job and each round you’ll get a salary closer and closer to market rate (more about this later).  If the startup doesn’t do well, you’ll be out of a job when the startup runs out of money.  But you’ll be forewarned if the CEO is transparent — most of them are in earlier stages.  A startup is risky because you’re building something from nothing.  You’re doing something ridiculously hard because you believe in it and want nothing more than to see it succeed.  You’re not failing even when all the odds are against you.  You’re the underdog in many ways.

And by the way, if you’re a good engineer you’ll have zero issue finding another job.  Zero.  Every company in software, big and small, needs more good people.  This trend won’t change for a long, long time, either.

3) Opportunities for generalists: generalists don’t do well at big companies.  Big companies want you to be really, really good at that little thing you spend all your time on.  Not at a startup.  Although specialization is still important at most startups, there are far more opportunities at startups for generalists.  I’m defining generalists as people that have interests in one field or many fields.  For example, if you want to be an engineer and work on the website, the data infrastructure, and the mobile app, you’ll love a startup.  Similarly, if you’re an engineer and want to get your hands dirty in marketing or recruiting or whatever, a startup is also a great place for you to learn and grow.  To be totally clear, I’m not saying specialists don’t do well at startups — they do incredibly well.  Generalists, however, don’t do well at large companies.

4) Ownership and leadership: at a big company you need to wait years and years to become a true leader with big ownership.  Not at a startup.  If you’re awesome you’ll be able to grow and move up in your career far faster.  Mark Zuckerberg would have never been given a CEO role at a big company he started working for after college.  The only way he could find himself at the top of an organization is by starting it, or in the general case by joining a super small team.  Your career will be accelerated in a major way by joining a startup.

5) Transparency: startups usually have far more transparency than big companies.  You’ll know why the CEO decided to raise a new round of funding, or why a VP of marketing was hired, or why the company decided to open a new arm of business, or how the CEO did the recent round of investment.  There will always be information that isn’t shared, though, for example salaries and equity compensation, certain board meeting information, and certain sensitive investor information.  But in general every other decision made about the company will be transparent.  You’ll get to see how the company grows, why certain decisions were made, and how the company reacts to competitors and business plan changes.  All of this will teach you about business and prepare you to do your own startup one day.

6) Company culture: you get to help define it.  A company will be, for the most part, an extension of the founders’ personalities.  But especially in the early stages you’ll have a huge impact on the culture of the company as well.  You’ll be in a position to define company-wide celebratory goals, or traditions that the team rallies behind.  At the end of the day a startup is just a few people in a room.  If you’re one of those people your personality will rub off on everyone else and you’ll help create a company that is as much a part of you as you are of the company.

7) Hiring: you’ll do a lot of interviews, and you’ll be part of the decision to hire or not hire someone.  You’ll interview engineers, marketers, sales people, anyone.  You name the position, and you’ll probably interview any potential candidate.  Even if you’re right out of school you’ll still be asked to interview.  Of course, if you don’t like interviewing, you’ll only need interview potential team mates.  Read: if you’re an engineer you’ll only interview other potential engineers.

8) Financial incentive: in general your salary will be lower than at a big company, but your equity, or ownership in the company, will be significantly bigger.  Depending on the stage of the company you join, you’ll be granted anywhere from a few percentage points to a micro fraction of a point.  If the company is bigger, you’ll get fewer shares and your salary will be more inline with the market rate.  If the company is smaller, your salary will be smaller and your equity will be far greater.  Equity has a long, long tail, meaning the first 5-10 employees get significantly more equity than all other employees that follow, with certain exceptions for executives.  This is especially true for the first and second hires, though.

A little more about stock: if you join a company that is already doing incredibly well, you probably won’t get enough stock to retire unless the company turns into the next Facebook or Google.  In most cases, you’ll only get retirement money if you’re one of the first five employees.  Otherwise you’ll get a large down payment on a nice house, assuming the startup does well of course :).  Let me say that all again: except in very rare occasions like Facebook or Google, you can’t expect to join a company that is already killing it and hope that you’ll retire on the money your equity brings.

9) Politics: I’ve never heard of a company with more than 50 people that didn’t have politics.  Politics are a necessary evil whenever a company reaches a certain size.  The point of no return is when the first middle manager is hired — or when the first job opens up that is about controlling people and nothing more.  Small startups can have politics, too, but in the early days there’s generally too much camaraderie and too much daily work to worry about power or any other bullshit like that.  Oh yeah, and while I’m here, unless the leaders of a startup are lame, there won’t be any bullshit.  Everything is pragmatic at a startup, or at least should be.

10) Be a part of something bigger than you: at a startup you’re a part of something much bigger than just what your job asks of you.  Sure, you need to write code, publish blog posts, whatever, but you’re doing much more than that.  You’re building a company.  It’s hard to describe what that feeling is like, though.  Being a part of a small company is somewhat like creating a community or finding new best friends.  You’re making something from nothing, with people who are in it for the same reasons you are.  You’re at the apex of what might become something big, something meaningful and different.  And the excitement is amazingly powerful.