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Written by Elliott Hauser, Co-Founder of Trinket and Winner of Startup Weekend Education Raleigh. 

Trinket was formed with the intention of putting educators at the center of open education. By providing teachers the technology to disrupt and innovate education – the Trinket team has discovered two things:

The Trinket team has been working towards this vision since 2013. After winning Startup Weekend Education Raleigh, we’ve grown, pivoted and brought on new team members including our former SWEDU event judge. Together we’re building the tools to make a difference in your classroom. A year ago, I wrote an article detailing four lessons from Trinket’s first four months – now I’m ready to share another nine lessons we’ve learned on our journey from a Startup Weekend into classrooms around the country.

Startup Weekend group photo

Our Next Nine Lessons

13 months into a startup we’ve been through ups and downs, hiring and firing, coding, blogging, traveling, and pitching.  Here are nine lessons that I’ve learned along the way.

1) Not later. Now.

As founders and early team members, you’re the ones who must filter through the mountain of tasks that might be a good idea and find the tasks that will be crucial to your success. I’m a big believer in not sweating the medium stuff. This system is quite simple. You can not afford to push off the big things; do them now. You can easily knock out the little things; knock them out when you can. You can push off the medium things; push them off until they become big. Whatever system works for you, make sure you’re finishing the most critical things first.

2) Lead with a question

This is a phrase we live by at Trinket and it means two things.  First, lead your team by seeking to understand them and their ideas. Looking back, the majority of disagreements on the team were because someone – often me – had not taken the time to hear out and understand someone else’s insights.

Secondly and more broadly – your default move should be to ask questions.  Dive deep into your users, the tools you use in your business, and your investors. Living in a fantasy land that doesn’t match the real world is one of the most omnipresent dangers for any startup, and asking questions is your best defense against this. For Trinket, asking our users why they were using our product helped us to realize the importance of our interactive technology so that we could focus our development and marketing on it.

3) Make your users your partners

We talk with Trinket users and potential users several times a week. We use Intercom to target users who’ve talked with us before and ask them if they’d like to be interviewed. These interviews help inform our product design, messaging, and make up a cool series of user  interviews we publish on our blog. By turning our users into the superstars, we can treat them as partners rather than prospects. This collaborative relationship bears fruit for us every day in the form of referrals, social media mentions, and even helpful bug reports.

4) Make your competitors your distribution channel

Partnerships with competitors can be just powerful. Until just a few weeks ago, we were a teaching platform. We quickly realized that by making our interactive technology embeddable on any page like a YouTube video is, we turned each of our competitors into a distribution channel. We’re now in talks for deeper integrations. This isn’t possible for every business, but if you can do it, do.  It will pay off for years to come.

5) Give your team a rhythm

Startups lend themselves to a lack of structure.  Be it writing code or blog posts, much of what we do requires stretches of uninterrupted time. And, with crazy travel schedules and nightly events, it can be hard to keep regular appointments. In the midst of this chaos, it’s important to set and maintain a weekly rhythm. If you miss a beat, fine. Just make sure you sync up regularly and keep some continuity so you can hit your most important targets.

6) You cannot over-communicate your company’s vision

This is something one of our investors once said and I’ve taken it to heart. As a keeper of the vision, it’s your job to communicate it loud, clear, and often. In fact, my sign that I’m not doing this well is when our users, our team, or our investors get confused. The word communicate is important here too: it’s a two way street. Every time you communicate the vision you’re giving those users, team, and investors a chance to make it better or share a perspective you hadn’t thought about.

7) Your advisors and investors are your posse

If you’re doing a good job building support for your idea, you’ll attract some talented entrepreneurs to work with and maybe invest in your idea. Initially, I made the mistake of treating our investors like scorekeepers I wanted to impress. This prevented us from getting their hands-on help with the challenges we were facing. Your investors want you to succeed and have valuable skills. Treat them like your posse and call them in when things get tough instead of trying to impress them by going it alone.

8) It’s all in your head

“It isn’t the mountains ahead to climb that wear you out; it’s the pebble in your shoe.”
-Muhammad Ali

Startups are freaking hard. I believe that most startup founders are physically and psychologically capable of succeeding, but yet many don’t. Why not? In short, they psych themselves out. This is why legendary investor Paul Graham focuses so much on teaching startups how to not die.

  • Step One: don’t run out of money.
  • Step Two: don’t give up.

Step One is quite difficult, but Step Two is what does most companies in. Giving up isn’t a one-time event that happens on the day a company shuts down. It’s your motivation’s death by a thousand cuts from a secret belief that survival isn’t possible. The Mental Toughness that sports coaches talk about is the only thing that will save you from this. Don’t succumb to the fate of the weak minded. As Ben Horowitz writes in The Struggle,

“like playing three-dimensional chess on Star Trek, there is always a move…remember that this is what separates the women from the girls. If you want to be great, this is the challenge. If you don’t want to be great, then you never should have started a company.”

9) It’s a rafting trip, not a roller coaster ride

Unlike a roller coaster, which was designed by an engineer to thrill you and keep you safe, rapids are there simply because gravity is pushing large amounts of water over some huge, hard rocks. Like the wild, untamed markets we’re going after – the combination of the flowing inertia of the water and the unyielding hardness of the rocks combine to make a path that few, if any have traveled before. Like traveling to a remote river, no one forced you onto your startup journey; you chose it. If you make it though the glory of your achievement will come from the difficulty of the course you charted and whether and how often others have achieved the same thing before.

Rafting isn’t all exhilaration either.  There can be long, slow stretches of weak current where you exhaust yourself trying to build momentum or risk running out of supplies.  Do your homework, know the maps by heart, and do your best.  With luck, planning, and skill, you’ll make it through.

If you find that you don’t have the stomach for the journey, there are plenty of safe, seat-belted seats on the roller coasters closer to home.