Why I’ll Never Miss LessConf

How’d you spend your weekend? Did you mow your lawn? Do your laundry? Sleep late, watch TV, or catch a movie? Yeah? Well, I went to LessConf 2011 and got inspired, and now I’m on fire. Hope your lawn looks great.

Today’s artists and creative types have turned away from splashing watercolors on wetted paper, penning gloomy poems in battered notebooks, or recording songs that bemoan past loves. Instead, they’ve embraced a canvas meshing text editors with S corps to build web sites and start companies. The duo running Less Everything, Steve Bristol and Allan Branch, round up the best of them every year and hold a two-day inspiration-fest that leaves you determined to flush the sludge your life mires in and paint the world with your own genius.

Less Everything hyper-focuses on serving their customers, and both Branch and Bristol are social guys. They blog about reaching out to people, organize Bar Camps and lunches, and go to conferences not to learn but to catch up with friends and meet new people. You can see that Branch really likes people, but that Bristol breathes people like you breathe air, suffocating in even seconds of solitude. LessConf gives him an excuse to convene an audience to preen for, party with, and provoke with his opinions, probing questions posed to the speakers, and apparel, which this year included a kilt and then, in a shock-’em-with-sensibility move, a business suit and tie that must have been a gift. While he was wearing the kilt, though, I could only pray that he bucked tradition and donned BVDs, and I refused to look any time he twirled.

Here’s a summary of what I learned from the speaker panel:

Tom Rossi, Molehill

Tom Rossi from Molehill kicked off the show by admitting that he’s a quitter. He one day found himself making good money in a good job that made him miserable, so he quit to find his passions, which led him to found Molehill. His talk focused on introspection, imploring us to find our passions, realign our ideas for success, and determine how we measure good. He said to then stop talking about doing something and go execute: pick your idea, ignore the detractors and distractions, and build the best something you can.

Rhonda Kallman, New Century Brewing

The next speaker, Rhonda Kallman, cofounded Boston Beer Company in 1984 and helped launch Samuel Adams in 1985. My religion, Mormonism, proscribes alcohol, and the closest I’ve come to tasting alcohol in my entire life is an occasional capful of Nyquil to ensure a decongested night’s sleep and a one-time sip of the non-alcoholic O’Doul’s whose taste left me questioning beer’s popularity to this day. By the time Kallman finished speaking, however, I was ready to quaff Edison Light by the case. She was amazing. She left executive perks and an amazing salary when Boston Beer got bought and became too corporate to found New Century Brewing, which pioneered craft light beer with Edison Light, and then caffeinated beer with Moonshot. Her decade with New Century Brewing is a tale of right place, wrong time, and the doggedness she displayed through setback after setback boggles the mind. To get an idea of the magnitude of the setbacks, her battle with breast cancer merited only a sentence in her talk. Funding bloomed like mirages, only to disappear, and the FDA shut her down on speculation, not evidence. Her story, though, is that sometimes you can’t plan for things, and that reinvention must take place every day. A friend later said that her talk paid the price of the conference.

Sandwiching lunch were two musicians, Allison Weiss and Julia Nunes (rhymes with “tunes”), who strummed (guitar for Weiss, ukulele for Nunes) and crooned and sounded terrific. The musical interlude was a nice touch for both entertaining and inspiring from a different angle.

Jason Beaird, MailChimp

Jason Beaird, the author of one of my treasured design books, The Principles of Beautiful Web Design, spoke next on the importance of knowing the rules of design, and then knowingly breaking them. Following all the rules, as the 5-star recipes on allrecipes.com do, produces designs that appeal to everyone, offend no one, and are never extraordinary. “Piss on the principles,” he said, to produce inspiring designs. He reminded us that one beauty of design is that is has no right answers, meaning we can always improve a design, and then closed with the Gene Hackman Willy Wonka: “We are the music makers and we are the dreamers of dreams.” Great stuff.

Sarah Hatter, CoSupport

To close the day, Sarah Hatter, formerly of 37signals and founder of CoSupport, explained why our customers don’t like us enough. She made Ralph Nader sound like a corporate shill. She contrasted how the customer service staff at CVS treats their customers with how the staff at J. Crew treats theirs. CVS staff act annoyed, resentful, and sullen, while J. Crew staff stop what they’re doing, turn and face the customer, and engage. Customer support, Hatter says, is being intentional about the message you send. She talked about both the figurative message and the literal: the email messages sent to customers. She vilified empty words like “feedback,” “inconvenience,” and “appreciate,” and instead charged us to use full words like “thank you,” “this sucks,” and “you’re right.” In her estimation, technical people, who are usually introverts, shouldn’t be doing customer support. Instead, for your customer support staff, you want people who are a little bit overwhelming.

After a jog in Piedmont Park and a dinner that included my first steak tartare, my colleague Joshua Livermore and I dropped in for a little while on the LessConf party, catching up with some friends and meeting some new ones before the drive, run, and day caught up with us and we headed back to the hotel for much-needed sleep.

Jeff Lawson, Twilio

Jeff Lawson from Twilio launched day two with a talk on what he dubbed “DOers,” who are people who get things done without waiting for instructions. He talked about how they interview people to find DOers by showing them a step-by-step graphic for drawing an owl that goes something like this:

1. (Shows two circles, one atop the other) Draw two circles.
2. (Shows a completed, intricate drawing of an owl) Draw the rest of the owl.

To work for Twilio, you must understand that no one will guide you on what comes between steps one and two; you must figure that out for yourselves.

Lawson spent his talk on the “mating calls” for DOers — the things that attract people who get things done. The mating calls for a DOer-centric website, for example, include a product tour, screenshots (which he called the porn of selling software), pricing information, a signup or other lead to action, and an API — things that let DOers dive in, understand the software, try it, and buy it. Contrast that with non-DOer, enterprise sites like Oracle, who don’t want you to dive in, understand, or type in your credit card number. They want you to call them, negotiate with them, and hire their experts to install and configure their software. One way he said to determine that a site sells enterprise software (besides the “how to buy” explanation in lieu of an actual way to buy the software) is the multi-cultural nature of the people in the pictures. Enterprise software tries to be all things to all people and offend no one, so they show all races and genders in their pictures. I’d never thought of that, but it’s true!

Hiten Shah, KISSmetrics, Crazy Egg

Hiten Shah from KISSmetrics and Crazy Egg began with a slide saying, “Your marketing is the product.” He talked about marketing and social media, telling us all to get more serious about Twitter in our marketing efforts. By focusing on people’s problems and finding your “earlyvangelists” — the early adopters who will evangelize your products — you can leverage social media to market what you’re selling. People on social networks spend money, and B2B early adopters are on Twitter. He talked about the importance of what you call things, explaining that “beta” means “buggy,” and that calling something “early access” increases conversion rates. He finished with a video from Derek Sivers called Leadership Lessons from Dancing Guy that talked about the importance of the first follower, who transforms the lone nut into a leader. Watch it — it’s powerful.

Josh Williams, Gowalla

Gowalla lets you tell your friends where you are and see where they are, focusing on sharing experiences through photos and comments. Josh Williams, cofounder and CEO of Gowalls, inherited a landscape company from his mother when he was 18, and though landscaping wasn’t his thing, he ran it for three years and learned a ton about running his business. His talk, though dubbed “When to Quit and Other Stories,” seemed more about learning by doing and building on what you’ve done. His advice included things like hiring great people, keeping your hands dirty, stop doing things when they’re no longer fun, work hard (and transitioning from a service company to a product company will be harder than you think), and don’t fear abandoning a great idea. He talked about getting out of BlinkSale, about the lessons learned from PackRat, and how having brilliant designers working on PackRat led them to the beautiful icons and graphics in Gowalla. He advised against VC money (VCs aren’t as important as you think, nor as important as they think), saying that if your idea requires investor money to bloom, it’s probably not that great of an idea. Always be humble, though, as you’re building on others’ work.

Micah Baldwin, Graphic.ly

The next speaker, Micah Baldwin from Graphic.ly, talked about business lessons learned from strip clubs. Too squeamish about the subject matter to take notes, I instead listened. Some of his analyses were brilliant, though I struggled to understand how someone could unabashedly discuss his past cocaine use and current proclivity for places where women shuck their clothes for money in front of a large audience. It was a little too weird for me, but had some good lessons.

Steven Walker, Groupon

Lead designer for Groupon, Steven Walker discussed how to handle rapid growth like what they’ve faced at Groupon. He employed syllogism to demonstrate the fallacy of frantically going about your work to try to be fast: slow = smooth, smooth = fast, therefore slow = fast. Since time will always be a luxury, you’ve got to really know your stuff so you spend your time implementing, not researching our debugging. Designers should be able to handle development tasks, at least simple ones, and developers should be able to handle design tasks (again, at least simple ones), so that you can decide and solve and move on without stopping and assigning tasks and waiting for others to do something you should have done yourself. He decried designers’ propensity for designing for themselves, calling preferential design a “poison” and that designers should instead design for everybody else. Moving fast and shipping often isn’t an excuse to settle for less than greatness, however, and we need to make sure our work is giving us goosebumps. We should risk being fired, go big or go home, and push something new.

One event from LessConf paints a picture both of the tone of the conference and the sense of adventure it raised in people. Bristol announced that they were giving away Manpacks to the first 10 people to vault on stage, so the stage quickly filled with folks wanting free stuff. Once onstage, they found out that they could double the amount of free Manpacks they received if they let Branch give them a wedgie. Now, Branch played O-line in college for a D1 school. He stands 6′ 4″ and must hover around three bills. He’s the last person I’d want near my underwear, but more than half the people went for the wedgie and more free stuff, even after seeing other hoisted off the ground by their Fruit of the Looms!

LessConf 2011 may be over, but the inspiration will carry me for another year — at least until LessConf 2012. I’m marking my calendar now, and setting a goal: to one day do something cool enough to get the invite to speak at LessConf. As all the speakers say and demonstrate, that could be any of us up there sharing inspiring stories of what we’ve accomplished, if we’d just set aside our fears and reach for the impossible!