Entrepreneurship can be a rocky path, and it certainly doesn't come with a handbook. While each speaker originated from entirely different industries with entirely different goals, each spoke to the importance of longevity, balance, and community.  

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Jason Fried Talks to Scott Heiferman

Photo: MACKME.COM

Founder & CEO of Basecamp // Co-founder & CEO of Meetup

The founder of Basecamp (previously 37Signals), Jason Fried is an entrepreneur committed to creating simple, elegant products that endure, while working and living in a balanced way. His close friend and interviewer Scott Heiferman not only created a company and millions of personal connections around the world, he also added the word "meetup" to our lexicon. Heiferman interviewed Fried about an often ignored issue in the startup world: making startups and products that endure.

• "Starting something new is sexy, but maintaining it is the harder part, and that's what's interesting." Entrepreneurs are so focused on starting, on the next, big "new" thing. But Fried wants to "be in a long walk, instead of always sprinting everywhere." He's more inspired by those who figure out how not to go out of business than those who got big overnight. We can often learn more from industries that are considered less notable ("like lawncare") where companies are often still around for more than 25 years.
• Don't screw over your customers. In order for companies to endure, it sometimes means cutting back on projects that only did so-so. That doesn't mean you should kill products entirely and ruin it for those customers who loved them. Fried, and Basecamp, believe in treating those like babies — once born you should always support and maintain it, even if it's no longer your foremost-focus. This means no longer innovating or putting in the extra effort (full disclosure: treat your startups like babies, but please don't treat your babies like startups), and thus not alienating existing consumers. For Basecamp, that meant changing their name from 37Signals and cutting ties to several of their smaller, but demanding, side projects in order to focus all their energy on taking Basecamp to the next level. For Fried, it was as no-brainer: "Quality was going down across the board as we stretched too thin... But what we were known for above all was Basecamp."
• "Chaos is man-made, which means it can be man-prevented too." If your company is always frantically in reaction mode, that's on you. Paying too much attention to what you can't control, like other competitors or copycats, only breeds more chaos and anxiety amid your team.

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Joanne Wilson

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Angel Investor & Founder // GothamGal

Joanne Wilson went from a buyer at Macy's, to running a company, eventually leading to spearheading sales for a start-up magazine/e-zine/events company called Silicon Alley Reporter. She's since been an adviser and investor in the start-up community, and has run her own popular blog, GothamGal, since 1994. As living proof of non-linear paths, Wilson shared her top lessons from a life of entrepreneurship.

• "Career is no longer a word." There is no set career path anymore, and in the same vein there is no "traditional" entrepreneur either. You don't need to live the stereotypical Silicon Valley lifestyle to be successful. Make work and life separation a priority.
• Figure out your endgame. Build your business through the lens of the lifestyle that you want to have later. If your desired end goal involves having a lot of free time to work on other projects, build the infrastructure for that from day one.
• Make your passion your livelihood. Your creative talents are what allow opportunities to emerge; embrace it. As Wilson said, "The most successful artists & entrepreneurs believe that it's something they MUST do, not just what they should do."

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Susan Gregg-Koger

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Co-Founder & Chief Creative Officer // ModCloth

By focusing on customer engagement and great curation, Gregg-Koger turned a love of vintage clothing into a $100 million mobile-first, e-commerce business. An authentic voice and perspective creates genuine bonds between your products and your customers, because as Gregg-Koger explained, "We are our customers, too."

• "If you don't look back at old work and cringe, it means you're not getting better." Even if your first version is successful, still look for feedback on how to push it further. 
• It's OK to be a rookie. Don't be afraid to start simply because you aren't already an expert. Approaching a project with a clean slate enables you to innovate without even realizing. When you're a newbie, you won't be boxed into the traditional approach or standards. Once you're past rookie phase, it's always helpful to keep a few close by for that fresh perspective (even if it means asking your mom).
• Fake it 'til you make it (appropriately). It's okay to ask questions. Don't worry about looking uninformed or naive, as it's often questions that might seem "dumb" to you that help others see practices in a new light or perspective.
• "Put your brand in the hands of your community." Your community is your greatest asset. They provide instant, unbiased feedback and you help to empower them through the process. The exchange creates strong emotional ties, not only of your customers to your brand, but of your team to the work as well. At Modcloth, they've allowed their customers to have real impact from start to finish: customers vote on what products they want to come to the store, they leave feedback and vote for better iterations of stock, and share their own photos of how they wore their purchases.

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More 2014 Conference Recaps:

Part One: What Are Your Creative Values?
Part Two: Rethinking the Way We Work
Part Three: Rethinking the Way We Lead
Part Four: The Best Way to Complain Is to Make Things
Part Five: Creating a Business That Withstands the Test of Time
Part Six: Innovation Lessons from the Trenches