Replacing Oneself as CEO

I am very happy to announce that Fred McIntyre has joined awe.sm, the company I founded and have led for the last 4 years, as CEO (read more about it on TechCrunch). My new role is Head of Product Development in which I will continue to lead product, strategy, and engineering.

This is at once one of the hardest and best things I’ve ever done.

There’s a lot of great writing out there on hiring non-founder CEOs from a business perspective: if you don’t want to have to do it, do these things (I definitely didn’t do enough of them); if you think you might need to do it, think about these things; and if you’re going to do it, try to do it like this. So what I really want to talk about is the personal side of this process from my perspective as the founding CEO.

I wish I could say this was my idea, but frankly I wasn’t self-aware enough to come up with it. To be an entrepreneur I believe one must have a somewhat irrational belief in your own capabilities, otherwise you’d never be dumb enough to start a company. Regardless of any perceived glamor, most entrepreneurs I know will tell you that starting and running a company is fucking hard and there’s often more misery than joy. But there’s just something broken in us that makes the prospect of doing anything else seem even worse. For those of us with this particular defect, I think the Peace Corps slogan sums it up: entrepreneurship is “the toughest job you’ll ever love.” The thing in me that drove me to quit my job, move in with my parents, and start awe.sm is the same thing that kept me going through incredible stress and the lowest of lows to make it to our Series A and it’s the same thing that kept me from asking for the help it was clear to everyone around me that I needed.

I put hiring a CEO in the same category as taking an acqui-hire or just closing up shop and moving on — things I would think about at 4am in the office on those darkest nights when I’d have a bout of sobriety about the insanity I’d turned my life into. And ultimately, things that represented the one unacceptable option motivating me to push even further beyond my limits I’d long surpassed: failure. In the early days, the only way for me to keep awe.sm from failing was to tie my fate with the company’s. If awe.sm failed, I failed. But as we switched from lean startup to growth company, I didn’t fully realize how making my ego a shareholder went from being necessary for survival to being a limitation on what we could achieve.

Fortunately, I have an amazing Board that cares about me as a person as well as an investment. Mark, Ian, and Ryan took the time to help me see why something needed to change, and, to their great credit, gave me the decision of what to do. I will never forget the emotional tornado (roller-coaster doesn’t do it justice) of that day. After 3 and a half years of fusing my self-worth with the success of the company in the crucible of startup survival, it was impossible to tear them apart without pain. But while my first reaction was disappointment and failure, it was almost immediately washed away by a wave of relief. I knew everything they were saying was true, arguably better than they did, and I knew change was inevitable, but I had no idea how stressful and exhausting maintaining my internal reality distortion field had been until they gave me permission to turn it off.

The basic choice we had in front of us was to sell the company or hire a CEO. We had plenty of money in the bank, a great engineering team in an impossible hiring market, and real valuable hard-to-build technology, so we were in a better position for a sale than many acqui-hires. Personally, I still owned 30% of the company outright and selling would have kept me from having to give up the CEO role. On the flip-side, we would be starting from scratch on the CEO search and it would ultimately mean signing up for a Series B (i.e. more dilution) and several more years of awe.sm. The Board said they would support either decision, but only I could make it. Talk about a gut-check!

Guess which one I picked :-). It was far from an easy decision, I agonized over it for weeks and got advice from a lot of smart and experienced people (thanks everyone!). I made the choice and told the Board; they asked me if I was sure and I told them I was; I had second thoughts and talked about it with a bunch more people; the Board asked me again if I was sure, I said I wasn’t but I was committed. And all this was before we even started recruiting a CEO! I ran the search process, screened all the candidates, and ultimately had the final say on who we hired.

I chose not to sell because I believe the opportunity for awe.sm is too big to ignore, and I chose Fred because he shares that belief. When Fred accepted his offer, Mark Suster said that he thought this would be the best year of my career. I hope he’s right, but I’m at least certain it will be the best year of my life since starting the company.

The Ringers Rocking LA

The Ringers are an LA band fronted by Joe Hursley (aka White Gold). I first caught them opening for Fool’s Gold at one of Little Radio‘s Summercamps in August (see 3rd video below) and they stole the show. The music has started to grow on me, but the performance is pure LA punk and cannot be ignored. If you like to rock, don’t miss a chance to see them live.

“Beaver Fever” and “Keepin’ Your Head Up” at The Viper Room on October 16, 2009 (Joe takes my camera on stage about 2min in):

“Scene You See” at The Viper Room on October 16, 2009:

“Scene You See” at Little Radio Summercamp on August 30, 2009:

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It’s a way small world after all!

This struck me as so weirdly incestuous/small-worldly I had to post it. I just came upon a song featuring vocals by Sandra Possing, who happened to be the bartender at Delaney’s when I first met with Todd to discuss what is now awe.sm (she even tweeted about it!). Not only that, but I found the track through friend and former co-worker Lucas Gonze, and it’s being hosted on a site built by another former co-worker, Ethan Diamond.

The social media singularity is officially upon us people! Enjoy the music:
<a href="http://gavroche.bandcamp.com/track/hopefully-ile-st-louis">Hopefully, Ile St. Louis by Gavroche</a>

Mas Edward Sharpe

First of all, my life does not suck. Last night I was hanging at TechStars (and having my company mistaken for one of theirs 😉 ), this afternoon I was having lunch with the Gnip team in beautiful Boulder, and tonight I was filming a concert by one of my favorite new bands.

I’ve now seen Edward Sharpe and the Magnetic Zeros 5 times in the month since Ty and I first saw them at La Cita. And thanks to Dave at LittleRadio, I was invited to be part of the crew that filmed their three show residency at the Regent which ended tonight. That footage is in the capable hands of the Artificial Army crew, but here’s some stuff I shot at last week’s show with my G7. I’m primarily putting this up for Ryan, who has been at every one of the 5 shows I’ve attended 🙂

Edward Sharpe Rawks My F*%$ing Socks!

My new favorite live band hands-down is Edward Sharpe and the Magnetic Zeros. I saw them twice in 5 days and would go see them again tonight (and tomorrow night, and the night after that) if I could. They’re apparently starting a ‘residency’ at the Regent Theater in downtown LA on April 30, and I’ve already asked Dave at LittleRadio if my cousin Ben and I can shoot a proper concert video one of the nights.

In the meantime, here’s some footage I shot of their show at The Echo on Monday night (YouTube HD doesn’t quite do the 1080p footage from Kelly’s Canon 5D Mark II, aka my dream camera, justice):

And here are the photos:

Kelly (and her camera) had to leave a couple of songs into the Edward Sharpe set (I had told her they went on at 10pm and they didn’t end up starting until 12:30am). So, what you see here is just them getting started — to give you a sense of where it ended up, Alex, the lead singer (formerly of IMA Robot), spent a good deal of the show shirtless in the audience. I’m actually kinda glad I didn’t have the option of documenting the rest of their set, because I got to go crazy with the rest of the crowd instead. But I’d gladly give up a night of rocking out in order to have the opportunity to properly document this incredible spectacle. Dave, call me! 😉

P.S. I first discovered Edward Sharpe and the Magnetic Zeros through the most excellent NPR All Songs Considered Live Concerts podcast (originally via Ian, of course).

Update: Here’s some video of the opener, Fool’s Gold:

I have 1 more Edward Sharpe video, but it’s just barely over YouTube’s 1GB upload cap. So, I guess I’m gonna keep it to myself for now.

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WTF is an (un)class? or On Diversified Living

I first heard the idea for (un)classes a little under 13 days ago when Rahmin pitched it to Todd, John, and me at the Lair on Presidents’ Day. So, what’s an (un)class? It’s exactly what it sounds like: a way to explore your interests without the formal structures of an educational organization; or what we have come to call casual learning. From the brand new (un)classes blog:

(Un)classes are to continuing education what BarCamps are to conferences — a lightweight, low-pressure, and most of all fun way to explore topics that interest you without having to make a big up-front commitment. 

Rahmin is one of those guys with a million ideas, and there’s something to almost all of them, but this one struck a chord with me. It was a product *I* really wanted, which is always a good sign. So, I started to think about why I wanted it and I came up with two fundamental themes that I think are resonant with a growing number of people.

Diversified Living

When I left Yahoo! a little over a year ago, I had spent nearly 4 years as close to singularly focused on work as humanly possible. Over those four years, I invested all of my life capital (i.e. time) in my career, which I thought was a sure-fire investment that would have a much higher rate of return than conventional instruments like hobbies and relationships — those only paid incremental quotidian returns, this could pay exponential life-changing ones. But then I was hit by a Black Swan in the form of Yahoo!’s well-documented struggles. And all of a sudden, a good portion of the capital I had accrued from my investment was in the form of influence within a company at which I was no longer interested in working.

So when I left, I vowed not to make that mistake again. I was not going to put all my capital into one life investment vehicle that could unexpectedly lose its value, I was going to diversify. I realized that life experience (i.e. travel, hobbies, etc) may not have a sexy upside, but it’s safe and pays a solid dividend. Whatever was to come next career-wise would never be a singular focus at the absolute expense of life experience.

However, I’m more than a little OCD (in the annoying perfectionist way, not the need to lock the door 7 times and spin around way) and I throw myself fully into what I do because I don’t know any other way. So, this new goal of life diversification would have to take forms that didn’t require an abundance of free time. But, there aren’t too many meaningful things you can do with a relatively small amount of sporadic spare time beyond read a novel or paint. You definitely can’t learn a new skill or study a subject that interests you, at least not through any conventional educational offerings of which I’m aware. And that’s where (un)classes fills a market void for me, it’s micro-education (Rahmin’s term) — a learning format with smaller basic units that fit my crazy lifestyle.

Weaponization of Hobbies

(First of all, credit to Raza for the term.) If micro-education is a format, then casual learning is a category within that format. What sets casual learning apart from other potential categories of micro-education is the inherent lack of competition, which appeals to my desire for my extra-curricular activities to be enjoyable and stress-free.

Don’t get me wrong, I’m a competitive guy. But, I think it’s somewhat ridiculous that you can go pro and/or compete in pretty much anything nowadays. Stuff that was meant to be fun has now been turned competitive at the highest levels, and I would argue that has trickled down to permeate every level of a given hobby to some degree. There is a certain expectation that by taking classes you are (at least in theory) fully committed to one day becoming an expert in that subject. And by not pursuing the next level once you get there, you are quitting. This implicit expectation can be very daunting for novices or dabblers and serves to keep people from even trying. What if I just care enough to only ever be a beginner?

And then there are the other students. Haven’t we all been there in the beginners’ sailing class with the guy who brought his own life-vest and keeps trying to complete the instructor’s sentences or in the introductory rock-climbing class with the guy who keeps volunteering how he’s only trying to get back in the swing of things after taking a few years off? I don’t want to spend my precious free time dealing with these people! Like I said, I’m competitive. So even if I’m not there to compete, I’ll end up taking it seriously just to shut that douchebag up.

Casual Learning FTW!

I believe both these themes, diversified living and a rebellion against the weaponization of hobbies, appeal to a lot of people who may not even know it yet or are just beginning to realize it.

The current recession has made diversified living not just something the growing ranks of the white-collar unemployed may see as a silver-lining until they find their next job, but a core value that will stay with them for the rest of their lives. The macro-economic Black Swan of the credit crisis is trickling down to become millions of personal Black Swans just like mine. Our generation that was trained to sacrifice everything short-term for our careers and the long-term benefits of professional success is seeing the foundational assumptions of that philosophy spectacularly undermined before our eyes. If all of a sudden I don’t reasonably believe that I’ll be able to make $10M by the age of 40, is the way I’ve been living my life worth the opportunity costs?

As for the weaponization of hobbies, everyone hates douchebags. ‘Nuff said. 🙂

Casual learning is unique in that it is purely learning for fun. By its very nature it can’t help you with professional training or becoming an expert at anything. And so, you end up with a self-selecting group of participants who are all there for the same reasons. What makes casual learning special is the community of intellectually curious individuals who want to pursue the joy of learning without having to make a substantive commitment to do so. (Un)classes fill the gap between nothing and full commitment to a subject matter and do so within a supportive and non-competitive group of like-minded individuals. 

(un)classes.com

We’re trying to launch the first version of (un)classes.com in time for LaidOffCamp this Tuesday. Rahmin and I are working on product and marketing, Marcus is helping out with design, the fantastic guys at Cloudspace — CoreyMichael, and Tim (who also happen to be the guys behind awe.sm) — are doing the development heavy lifting, and Todd has even offered to chip in on some CSS work. It’s a side-project for everyone involved that basically kicked off Thursday night, and it will be nothing short of a miracle if we pull it off (and I promise to write about the process if we do). But we’re all really passionate about the possibilities of the idea and the community it can create, and we want to start using this product ourselves. 😀

If you made it this far, there’s a high likelihood you’re digging on the idea of (un)classes as much as we are, and you’re wishing there was a way to get involved right now. Well, today is your lucky day! Even though the site isn’t up yet, Rahmin setup a way for you to submit ideas for things you wanna learn and things you wanna teach. When the site goes live, your submissions will be the first classes in there and you will get an email with your account info. Of course, you can also follow (un)classes on Twitter and/or subscribe to the (un)classes blog.

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Everything Must Go! – The Great Strauss Virtual Garage Sale

I moved to Palo Alto on June 13, 2004 — my 24th birthday and the day before I started at Yahoo!. I’ve been living in San Francisco since June 2005, first in Russian Hill with Damon and Eugene and on my own in the Marina since June 2006. And, now I’m moving back to LA (more on that later).

It took me 2.5 years of living on a mattress on the floor before I actually got any furniture up here. And now, I’m selling it all on Craigslist:

It’s interesting to see the bulk of one’s material possessions all listed like that (and, yes, the bulk of my material possessions come from IKEA). I look forward to owning a lot less crap very soon.

And if you’re in San Francisco, come kiss my ass goodbye on December 6! 😉

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All is right with the universe.

I woke up this morning to find out several pieces of important news. First, the Large Hadron collider was switched on and didn’t destroy the earth (yet). So, that’s good.

And in other news, my friend Joel WON $100,000 FOR WRITING A SONG ABOUT A KLONDIKE BAR!!!!!!!!!!!!!

Happyjoel Wins $100k Klondike Contest!!!!

This news cut through my hangover (from ruining Andrew 😀 ) like a hot knife through butter. Not only am I unbelievably proud of Joel for succeeding at his lifelong dreams of becoming a professional contest winner (even with his raging coke problem, $100k should hold him over for a while — well, after taxes…hrm, maybe not), but I also feel a little bit of pride in whatever small help my mercilous shilling to my social network may have contributed to this mighty achievement.

(And yes mom, that last parenthetical was a joke. Joel doesn’t have a cocaine problem. He’s just a sex addict. However, his primary interest is sex with marine mammals.)

Joel also happens to be the first client of my new company (more on that soon). And even though I said before we’d do the work for free, we might have to start charging a little bit now 😉 .

Way to go Joel!!!!!!!!!!!!!!!

Congratulations to the Yahoo! TV Widgets team!

Last week, my former team at Yahoo! launched Yahoo! TV Widgets to some great press coverage. This is a project that was underway before I left, and drew heavily on the work and people of the Konfabulator/Y! Widgets team. It goes all the way back to the original Konfabulator team of Arlo Rose, Perry Clarke, and Ed Voas, who first popularized the term “Widget” for consumers as “whatever you want it to be” (much to the chagrin of Marketing & PR folks and proud mothers of people who work on Widgets everywhere 😉 ). They pioneered the concepts of open developer platforms and mash-ups that are all the Web 2.0 rage today, they just did it on the desktop. By the time I joined the team nearly a year after Konfabulator was acquired by Yahoo!, they had built a thriving ecosystem (yes, it was a real ecosystem, so I can say that without being buzzword compliant) of thousands of independent developers and millions of users worldwide.

Yahoo! TV Widgets As we continued to build the team and grow both the user and developer bases, we began to learn and build things that we realized had much broader applicability than just Widgets for your desktop. With the help of our marketing all-stars, Brady Wood and the awesome Shan-Lyn Ma, we started to create best practices and tools for building and cultivating a community of independent developers around an open platform and helping connect them to users. This work resulted in the relaunch of the Yahoo! Widget Gallery (which, for the sake of that douche over at VentureBeat, pre-dated the iPhone App Store) and a number of other improvements for the desktop Widgets product. But, it also became an essential part of the launch of Yahoo! Mobile Widgets at CES, the TV Widget launch at IDF last week, and some other stuff that’s still in the works down in Sunnyvale. It was also a great opportunity for us Konfabulistas, many of whom got to work on some of these fun projects and some of whom even moved on to these new teams.

So, in addition to being happy for my friends, who have been working on the TV Widgets project these last few months since I left, I’m proud to see the work we started (finally) coming to fruition. Way to go guys (and girls)!

The best cause on the Interwebs. Ever. Really!

Lonely Arctic Penguin       

Lonely Arctic Penguin, originally uploaded by happyjoelmoss.

Holy schnikes! My boy Happy Joel has made it to the finals of the What Would You Do for a Klondike Bar Contest!!! That means he has a 1/4 shot of winning $100k!!!!!! (Arguably, he should have better odds since it’s ostensibly a merit-based contest, and his video is definitely the awesomest.)

This is exciting to me on a number of levels. First of all, Joel has been a friend of mine since he moved out to LA about 5 years ago, and we share a mutual best friend (hi, Devra 😀 ). He’s someone who I truly admire for having the unabashed courage (and/or stupidity) to blindly pursue his goal of making a living amusing others. And, he’s the only person I can ever imagine even attempting the full-time occupation of professional contest winner, let alone succeeding at it (for more back-story, check out his blog). So, I want to see him succeed on that level as well, because I have a dream of a future in which “Professional Contest Winner” is a choice in the drop-down menu for the “Occupation” field on forms. I also have a (psuedo-)professional interest in seeing Joel succeed. I’ll post more on this in the near future, but I’ve been working with Joel over the last month or so on how to use the off-the-shelf tools the web has to offer (e.g. WordPress, Flickr, Twitter, Facebook, etc) to build and cultivate a fanbase to unleash at times like this. So, having him win something like this means I can actually start charging him for my pearls of wisdom 😉 . And finally, his shit really is pretty damned awesome. But, don’t take my word for it, see for yourself.

Here’s how to vote:

  1. Go to http://klondikecontest.com/finalist.aspx
  2. Register (or sign-in, if by some miracle you’ve already registered). Yes, registration is a pain in the ass and the ad agency behind this is a bunch of morons for requiring it, but we don’t have any control over that. Plus, you could win $25k from Klondike just for voting and Joel will totally make it worth your while if he wins.
  3. Watch happyjoel’s video, and rate it 5 bars (Klondike Bars, get it?). Also, leaving positive comments for Joel’s video (note that they don’t appear in realtime and must pass an editorial review before being posted, tools!) and/or rating other videos lower than Joel’s can’t hurt.
  4. (Optional) If you happen to know any of the Lonely Island guys, who will be judging the final outcome of the contest, put in a good word for Joel. (I’m looking at you, Hurwitz.)

And, please blog, Facebook, Twitter, Digg, or [insert social media nonsense of your choice] this to help spread the word.

P.S. The photo up top pretty much says everything you need to know about Joel: it was taken on a cruise to the Arctic (the same one on which he filmed the Polar Bear bits of the Klondike video), which he won in a Nature Valley Granola Bar contest, and he purchased and schlepped a giant penguin suit all the way up there just to stage a photo of him as the only penguin in the Arctic. I mean, how can you not love this guy?! (He also just pulled a similarly Ludacris stunt on his recent trip to Australia.)