LessMoney Conference Inspires, Influences With Ideas, Lessons Learned

Shawn Berg can't complain that his Tampa-based web design company, iTistic, is doing well enough to employ four people, but being the founder isn't a breeze. When the 32-year-old New Jersey native got married recently, he felt the tension between running a small business and having a life.
"Just going on a honeymoon for a week-and-a-half was stressful,'' Berg says of temporarily abandoning iTistic.
Sound familiar?
Last week, Florida-based entrepreneurs Allan Branch, 31, and Steven Bristol, 38, rolled into town to deliver their LessMoney Conference -- a two-day event that promised to help other small business owners move closer to answering the question: How can I run my business more profitably, more efficiently and with less trouble sleeping at night? Thirty-six tech geeks -- including Berg -- from as far away as Singapore and the Middle East as well as Tampa Bay joined them at the Courtyard Marriott in downtown St. Pete at $300 a ticket for some very candid advice.
Since 2007, Branch and Bristol, who live in Panama City and Jacksonville, respectively, have made a name for themselves as LessEverything. Their most profitable web app, LessAccounting, has won thousands of paid subscribers as a streamlined alternative to Quickbooks and other bookkeeping software; Branch and Bristol market it with the irreverent tag line, "We make accounting suck less.'' Today they employ around 14 people, including support staff for the conferences they host two-to-three times a year. 
Each conference has an open source format. In addition to the "Less guys,'' as Branch and Bristol call themselves, a handful of their colleague-friends dispense guidance as informal speakers -- in last week's case, Geoff DiMasi of Philly-based firm P'unk Avenue, Carl Smith of nGen Works in Jacksonville and Chad Pytel of Boston-based Thoughtbot -- all founders of successful web development companies. Attendees like Berg were encouraged to tell their own stories and task the room with collectively answering specific questions about how to grow a small business on less, from less money to less stress.
Answers were unreserved -- from Bristol's admonition to be "stupidly fearless'' while promoting your business, but never use the F-word in the title of a blog post (he speaks from experience), to group discussions about health and liability insurance costs and options.
Here are some highlights:

On Marketing

Sales is anything you do to obtain a check from a client, Bristol says, and everything else you do is marketing. Show your personality. In addition to blogging and tweeting about products and services, Bristol advises brainstorming ways to attract positive attention by using a principle he calls, "Wouldn't it be cool...,'' as in "Wouldn't it be cool if LessEverything bought cupcakes for everyone at this conference?'' The answer is yes -- and probably worth as much buzz as a conventional sponsorship at lower cost.
Don't fear being irreverent. Branch and Bristol once promoted LessAccounting at a start-up pitch contest by suggesting that Quickbooks was a leading cause of suicide among adult Americans during their three-minute spiel. (They won the contest.) Smith's company, nGen Works, generated attention with the Happy Webbies, tongue-in-cheek portraits of prominent web developers -- nGen's heros and competitors -- that went viral within the industry.

On Selling / Sales
The LessMoney speakers cautioned against wasting unpaid time on elaborate proposals for prospective clients. Smith advised pitching a "paid discovery'' period. His company charges clients for a thorough get-to-know-you session that can last up to one week and results in a detailed outline of the project and scope-of-work as well as a sense of mutual compatibility. (If a client declines to continue after the discovery phase, they're left with a proposal they can use to hire a different company. More advice from Smith can be found on the nGen Works blog.)
Branch and Bristol urge two practices that newer business owners struggle with: screening clients to select projects that will showcase your best work and your values (rather than just bringing in a paycheck) and declining to work for a fixed bid. An hourly rate ensures that the client gets what he pays for -- not an over-inflated bid -- and protects you. "In the history of man, there's never been a software project that ended with the same scope it started with,'' Bristol says. 

On Hiring

The question of when to hire a first employee preoccupied many attendees, including Philip Zaengle, 27, a web developer based in Naples. "For me, the problem is just biting the bullet,'' he says. Speakers advise Zaengle not to wait too long. Once signed projects will yield the cash, hire someone before you start turning down additional work. And hire the right person -- preferably someone with not only the technical skillset you require but strong communication skills including writing, speaking and not being a jerk.  
DiMasi and Pytel speak in favor of providing benefits including health insurance and unlimited vacation. Vacation is only "unlimited'' on the condition projects are complete, but the reward inspires loyalty. DiMasi looks back on his decision to provide health insurance for P'unk Avenue employees, despite the considerable expense, as a moment that strengthened his commitment to his business's success and shaped his future choices. "That was the day the company became real,'' he says. 

Megan Voeller of Tampa is a contributing writer to 83 Degrees Media and the visual art critic for Creative Loafing. Comments? Contact 83 Degrees.
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