The CEO Freedom Experiment

The CEO Freedom Experiment

My work life totally changed as of last Friday. This was not unexpected… in fact, in some ways, I’ve been preparing for this since the day I started my company SCOTTeVEST about 15 years ago. I am still the CEO, but with the help of my team, I dismantled and totally rebuilt what it means to be CEO.  It was not unlike taking apart a classic car and rebuilding it into a leaner, louder muscle car. In my old role as CEO, I was a control-freak, a micro-manager, a hands-in-every-project style of leader.  It was natural to me, and it worked.  But it also made every project MY project. In my NEW role as CEO, I will still provide the vision, but not the operations.  The evangelism without the execution.  The approvals, not the details. It’s a 180 degree turn, and it’s scary.  But it’s also liberating. The idea of redefining my role as CEO has been in the works for some time, but now that it has arrived I was hit with a rush of emotions ranging from sheer happiness to confusion to nervousness to excitement, and a whirlwind of thoughts about new beginnings. This is why I did it. They Were Ready I use the word “they” with intent: a company CAN’T be ready.  Computers and boxes of products can’t be ready or unready.  But the people that make up the company need to be capable of not only sustaining what has already been built, but growing it, expanding it and evolving it without the Founder/CEO being involved in every decision. The people need to be ready...
Be the Squeaky Wheel and F.U.

Be the Squeaky Wheel and F.U.

How many times have you heard the phrase, “the squeaky wheel gets the grease?” While I usually take a counterpoint on conventional wisdom by encouraging people to bite off more than they can chew and leap before you look, I actually think being the squeaky wheel can get most people what they want out of business and life. As a car and motorcycle guy who likes to drive really fast, you better believe I take this phrase seriously.  The last thing you want at 100+ MPH is a $10 part blowing out under high pressure, and a new squeak from a performance vehicle is never a good sign. Squeaky wheels have their place in business, too… and they can cut both ways. Squeaky Wheel Employees To paraphrase Tony Robbins, if you want better answers, ask better questions. When an employee asks me good questions… that’s a good squeak.  When they’re 5 minutes late for every meeting, that’s a bad squeak. The most eager, hardworking, intelligent, thoughtful employee can still be stuck doing entry-level tasks if they don’t make their employer aware of their contributions.  Tooting your horn in this way is a good squeak, and can create huge results for the employee. 15Five has essentially created a tool to help people do this, and the key is that it’s not bragging if it’s true.  Wins should be celebrated, and it’s a true win if the employee accomplishes it on behalf of the company. Tell your boss what you’re doing, and you’ll excel if what you are doing is worthwhile and valuable.  If you are ineffective, ask for help.  Employers have...
Tech on Deck Recap

Tech on Deck Recap

Like many entrepreneurs, I thrive on accomplishing the impossible.  Perhaps you can relate. About one month ago, I had an idea to meet with my friend Robert Scoble (Futurist at Rackspace) during the Allen & Company Sun Valley Conference.  I live about a mile from the site of the annual, famed and secretive “billionaire conference,” and we thought it would be fun to hang out and see who we could run into around town. Of course, like all entrepreneurs and creative people, Robert and I couldn’t just leave well enough alone, and we started one-upping each other with ideas until the concept grew to become a major media event: Tech on Deck. This is Tech on Deck in a Nutshell Tech on Deck wasn’t a pipe-dream.  We actually pulled it together in about 2 weeks, secured sponsorships and assistance from Cisco, NewTek and UStream (in addition to our companies Rackspace and SCOTTeVEST), and fully fleshed out the concept. It started as two tech-oriented friends discussing the future of media and technology while riding on the coattails of a much bigger conference across town, and it essentially became the pilot for a TV show and proof-of-concept for a new media brand.  We had tons of viewers, had some phenomenal guests and even crashed a Mark Zuckerberg karaoke party…. We interviewed Guy Kawasaki, Hap Klopp (founder of The North Face), Gary Shapiro (CEO of CES) and close to a dozen other major tech influencers on topics that helped to dissect their vision of the future of tech.  While it’s fun to imagine the far-flung future, we were most curious about their...
Pocket Life #1: Grateful Dead and Tech on Deck… on deck

Pocket Life #1: Grateful Dead and Tech on Deck… on deck

Some of my fondest memories were from going to Grateful Dead concerts, and this weekend I attended one of the final ones… ever.  Almost 20 year ago to the day, I proposed to my wife Laura before a GD concert, so they’ve been a big part of our story. As with most concerts, no bags allowed, so I loaded up my SCOTTeVEST pockets with everything I needed for the show. It was everything you would expect!  From the “thank you for pot smoking” sign to the skywriter screwing up the peace sign, the air hung heavy with smoke and great music.  I even ran into my good friend Jim Louderback and had the opportunity to grab a photo with him in true Pocket Man style: Jim will be joining our Tech on Deck broadcast this week to discuss the present and future of publishing. Of course, being in San Francisco during the Gay Pride parade immediately after the historical marriage equality ruling was also a once in a lifetime treat.  I got to tag along with Thomas Hawk since he had special access to get close to the action.  I even got to see a poodle… which made me miss my girls at home: …ok, I actually saw two poodles. Another benefit of getting out to SF is that I was able to pick up my Pocket Rocket, a Polaris Slingshot and drive it home to Idaho.  It’s been months since I’ve been able to drive it, and it always gets attention… which you might be able to guess I love!  I even crowdsourced some advice on the best...
Best Advice for Entrepreneurs: F-U! Follow-Up (or Fail)

Best Advice for Entrepreneurs: F-U! Follow-Up (or Fail)

When you are first starting out in business, the people around you can have a profound influence on your direction, approach and even your happiness. If you’re lucky, you’ll be steered in the right direction by a good mentor, but sometimes even the best advice from a mentor doesn’t feel like it at the time. In my case, it turns out the best advice I ever received became one of the major keys to my success once I consistently followed it… but it took me years to realize how powerful that piece of advice was. F-U Lawyers Imagine this: I’m in my early 20s and just graduated law school. My future is ahead of me. I’m excited to start living an “L.A. Law” existence… fat paycheck, nice apartment, and a Porsche. I knew I wanted to buy a Porsche. After all, that’s what lawyers do, right? And I worked hard through law school so I could get a job at a great firm. And I did… but I never imagined how much WORK it would be. Enter my first law office mentor: Don Shindler. Don was a partner in the firm, and like Mr. Miyagi, he believed that the best way to get on track was to start “going through the motions” until the lesson finally sunk in. At first, I thought he just didn’t like me. He constantly reminded me about tasks, perpetually beat me to the punch (not literally) with follow-ups, and he insisted that I always CC him on all communications. Not important communications, not certain communications, ALL communications. This didn’t feel like the life of...
SkyMall Will Fly Again. Get Ready for a New Pilot.

SkyMall Will Fly Again. Get Ready for a New Pilot.

New developments in SCOTTeVEST’s bid to resurrect the bankrupt seat-back pocket catalog company A few weeks ago, the news broke that SkyMall was bankrupt. You know SkyMall – everyone knows SkyMall – that ubiquitous catalog found in the seat-back pockets of every commercial airplane in the US. Even if you didn’t love SkyMall, everyone knows what it is. I know it better than most: I sold my multi-pocket travel clothing line SCOTTeVEST inside for years. At first, it seemed like a shame that SkyMall was going away. What else would people read while flying cross-country after their devices ran out of power? Then, it seemed like an opportunity. Then opportunity turned into a plan. CNBC,CNN, NBC News, Reuters, TechCrunch, Engadget and even the Hollywood Reporter agreed with me: I am going to get SkyMall back into the air. But the media outlets are all missing something, and I’m going to tell you right here, right now, the rest of the story. The Plan for SkyMall: A LinkedIn Exclusive While I am playing much of our strategy close to the (SCOTTe)vest – and keeping a few aces in my pockets (since I am Pocket Man) – I just have to tease some of our favorite developments in our bid to rescue SkyMall. More than just a catalog. Sure, it looks like a catalog. But SkyMall has always been entertainment first, and shopping second. That’s the secret sauce that made it so compelling. While the “social sharing” of SkyMall’s content was limited to just exposing your travelling companion yet another outrageous product, the content was always entertaining. We will dial up...