Too many entrepreneurs and their investors waste their time looking around at what everyone else is doing. But nobody around you understands what you're going through. Neither do you know what problems other companies struggle to solve. You’re not going to learn much from the outside looking in. Just focus on where you're headed and why--and where you are right now on that path.
Affirm your vision weekly, then plan around it.
Every week I write down the one sentence that describes the problem we're solving at OpenSky and our plan for the company.
The problem: the Internet is too damn hard and time-consuming to use for emerging businesses because it rarely drives sales--and for consumers, shopping is impersonal and dominated by search.
The solution: OpenSky will empower businesses by building the simplest tools and community for them to grow and engage with followers. We will bring Main Street back.
This never changes. By writing it down, usually late on a Sunday night, I remind myself to spend the week focusing only on the high-impact projects that make that sentence a reality.
I've stopped advertising campaigns that advertised for growth but didn't drive small and midsize (SMB) business, I've shut down product releases for features that are extraneous, and I've made it clear to our team that this is what I care about and this is what we're doing. Nothing else. We're helping small businesses connect to consumers and grow.
Don't be such a hustler that you buy your own hype.
You have to be able to confront business challenges head on, listen to feedback, and, when necessary, to figure out what isn't working and then change it.
A good example of this is the role of celebrity users on OpenSky. When we launched OpenSky.com, we had tremendous industry reaction and momentum around all the famous people who were actively using and merchandising on the platform. It was exciting to see Bobby Flay and Martha Stewart using OpenSky to share their favorite emerging brands with their followers, and generally answering questions and engaging. But despite impressive results and great press, it was clear that our opportunities could be even greater.
Consumers wanted to interact with business owners directly, but we would never have enough manpower on our team to handle all of the brands that wanted to use OpenSky (literally thousands). We needed to enable small businesses to engage directly on our platform without the friction of retail buyers--no more purchase orders, no warehouses, no costly advertising campaigns.
When we became a platform and released our tools for small businesses, we offered up a bolder way to connect customers and sellers. We stepped out of the way and empowered the thousands of brands who wanted to be a part of the OpenSky community in order to grow their businesses.
Now, after nine months of intense development, merchants and member community (including celebrities) all engage on the platform. We’re more like Vine or Instagram than Nordstrom’s or Gilt.com. We’re a technology that connects buyers and sellers--it’s a much more scalable business.
Collaborate with your team with respect, openness, and honesty.
We have all-company key performance indictor (KPI) discussions every Tuesday at 5:30 pm and then again on Thursday at 5:30 pm. Why? Because you have to look at the numbers with your entire team so that everyone understands the priorities and why their work is crucial to the team’s success. We then have an open forum during which anyone can share anything we like. The best work happens as a result of us listening to one another. People have shared personal stories, others have voiced concerns, and most importantly, we collaborate on the mission.
By having a wide-open conversation centered on specific numbers, we can address the opportunities and challenges head on. Sometimes it has been a forum for my frustration, and I’ve let people know. Other times, my colleagues and I conceived of bold new programs. I've also rallied the team to do the impossible--and they’ve done it. No one is ever in the dark. In time, these conversations and regular forums create organizational harmony. We have a kind of group flow, and out of that come results.
Know your mission, your timing, and your place in the world.
People frequently ask me about Fab.com, Wanelo, or eBay. All of these are impressive companies led by serious innovators on serious missions. The mission at Fab is to create the world's best design store. They're well on their way. Wanelo is building a sharing platform for teenagers that isn't a store (no cart for checkout, etc.), but which is more of a crowd-sourced magazine such as Lucky. And eBay is the original social commerce company, full of the vitality of humanity and personal interactions.
None of these companies is the slightest bit like OpenSky. So when people ask, I remind them that I don't know what they're doing, but I know what we're doing.
The point is this: Investors invest in management teams they believe in. They also spend a lot of time looking at what the industry and market is doing and thinking about (and questioning) their own decisions. That’s their job. It’s your job to make sure they understand what you're building and why. Make sure they and your team see the opportunity. Never surprise either with bad news. If something is working, share it. If something isn't, share that too and make a plan to fix it.
Know yourself and your employees.
When I interview candidates, the first thing I say is always: "Tell me your life story." I'm looking for people who have created something: a company, a not-for-profit, a painting, a new market. Those are the people who inspire me and who understand the power and potential of true entrepreneurship. They have the emotional courage to invent.
Entrepreneurship is thrilling, so make sure you surround yourself with imaginative people. The employees at OpenSky were once college linebackers, lemonade stand builders, governor's aids, Peace Corps volunteers, book editors, hackers, anarchists, and theater geeks. Together, their unique perspectives help build the best tools we can offer. They make our platform possible.
Celebrate success (and failures, too).
We celebrate success with tequila shots and failures with ice-cream parties. And when we win, the Patron tastes sweet.