Burton Rast (left) and Harper Reed (right) at 1871 Fireside Chat

If you don’t hear that your idea is crazy, then you might not be trying hard enough

Harper Reed, the former CTO of both the 2012 ‘Obama for America’ campaign and Threadless, is one of the most influential, accomplished, and well-known members of the Chicago tech community. And – with his thick, black specs, long red hair and big beard – he’s also one of the most recognizable.

Now, after this week’s Fireside Chat, you can add ‘wisest’ to this already long list of titles. At 1871 on Monday, Reed was on-hand to share advice and stories with fellow Chicago entrepreneurs and discuss his new startup, Modest.

Below are our favorite ‘Life Lessons’ from one of the city’s best tech minds.

Forgetting Success:

“It’s very difficult to unlearn success,” said Reed. “But you need to if  you want to innovate.”

Entrepreneurs have the greatest freedom when success is still unattained. Ignorance allows startups to freely explore and to eschew norms rather than immediately jump into a particular model based on accepted benchmarks and guidelines. Granted, rules and success are comforting, but they can constrain innovation and endanger a group’s ability to stay relevant.

Reconsidering Practicality:

Reed acknowledged that, throughout his history as an entrepreneur, he’s been behind a number of successful though arguably “impractical” projects. But one of the major takeaways from his work has been that prioritizing practicality is rarely ideal.

“If you’re talking about practicality, then you’re talking about fear,” said Reed. “If you don’t hear that your idea is crazy, then you might not be trying hard enough.”

Yes, developers and groups should understand user needs, but, like reliving success, clinging to practicality may cripple innovation and development more often than not.

Dropping Hierarchy:

Successfully running a project or startup hinges on managing people and building a driven community. And the temptation may be to opt toward a rigid hierarchical power structure where everyone listens and follows the direction of one or a handful of people.

But Modest’s community is built on something better. Specifically, Reed has leveraged holacracy as the social technology behind his fledgling startup. Holacracy is an organizational system that distributes authority equally so that everyone in a group contributes. If optimizing communication is a concern, then holacracy may be the answer.

Building in Chicago:

Chicago’s innovation space is unique. It is not and will likely never be a carbon copy of Silicon Valley or New York, and that is a good thing. The question that startups have to ask is whether they can handle work in Chicago.

“I’m here because Chicago is the best. I want Chicago to continue being Chicago…[but startups] need to know what you’re fighting for,” said Reed.

Chicago’s innovation space is rapidly expanding, but startups need to understand how their particular vision leverages the power of the city.

Inside Modest:

Reed is currently applying these lessons to his new startup, Modest, Inc., which launched out of stealth mode this week.

Modest is a new platform for companies to create mobile commerce apps. Unlike platforms like Stripe, which process only one payment for a particular product, Modest allows retailers to sell larger store inventories to consumers via a simple and fast interface.

The concept is elegant. With a few simple taps, retailers can more easily sell electronically to consumers  and consumers can more conveniently purchase exactly what they want, when they want it. And Modest is a SaaS product, powering its clients from behind-the-scenes.

Finally, in a landscape where dev shops will charge thousands of dollars to build a transactional app, Modest is offering its services for free. (The startup also has a $200-a-month tier that provides additional features, like push notifications). Companies such as Chicago’s Intelligentsia Coffee have already started to use Modest to increase consumer sales.

Mobile commerce made easy? Sounds pretty practical.