Avatar photo

My Startup’s First Year – What I Learned

It’s been just over a year since Kyle, Ryan, and I showed up at TechStars Cloud in San Antonio for our first day. Just over a year since my first day in almost six years that I couldn’t tell people I worked at Salesforce. It was was our first day together as a real company. And it was the first day I realized that we were in way, way over our heads.

What’s amazing is that, despite our struggles along the way, the future looks very bright indeed for Keen IO. Our numbers are up and to the right, we’ve grown the team by adding the smartest people we can find, and our goals for 2013 are, well, aggressive, to say the least. So I’ve been thinking about what it took to get from there to here in the last year, and how that might help us in the future, and perhaps help others who are just beginning their startup’s adventure.

What surprises me most is how much I’ve learned. I’d like to share some of the things I’ve discovered. Some of it might be obvious to you, but I’m hoping you can find at least one interesting thing you didn’t know before. Without further ado:

Your Idea Doesn’t Matter That Much

The idea we applied to TechStars with is different from what Keen IO is doing today. Easily the hardest part of TechStars for me was wrestling with our idea. At first, that was convincing people that what we were doing was a good idea. Later, it was to convince myself (self-doubt is a strong poison). Eventually, we gave up and started talking about a different idea (in the same space).

No, Really, Your Idea Doesn’t Matter That Much

And that idea still didn’t get much love. So we hunkered down and came up with yet another idea (in the same space).

What Matters is Team

It took me a long time to understand that we were in TechStars not because of our brilliant idea, but because of qualities of our founding team. Our managing directors didn’t care if we started completely from scratch. They trusted that, based on our track record and experience, we’d be able to put something together given the structure of the program. Despite many moments of self-doubt, they were right.

People Care About You

I knew my family loved me, although they had no real idea what I was getting myself into. What I didn’t know was that there were non-family members people who genuinely cared about my success. And not necessarily for some monetary gain. It was an amazing experience to find these people and lean on them, in difficult and not so difficult times. It’s fair to say that the community we’ve surrounded ourselves in has been, easily, the biggest reason for our success.

You Don’t Have to be an Asshole

There’s this perception in the startup community that the best way to run a company is to be like a caricature of Steve Jobs. Emotionally volatile, secretive, prone to vitriolic outbursts, tyrannic, etc. That’s bullshit. Here’s the truth.

You DO have to deal with people saying that your idea sucks, that you (personally) suck, that you have to able to fire your best friend the minute they stop working out, that your only goal is to crush your enemies.

You have to be thick-skinned at times. But that doesn’t mean you shouldn’t share your feelings with your family, your friends, and yes, your co-workers. Being open and honest is miraculous. It’s sometimes harder, but the way it binds relationships together is second-to-none. Give it a shot. The worst thing that can happen is you can go back to being an asshole.

Be Transparent

This goes along with the previous point. There’s sometimes an unspoken assumption that the only way to succeed is to trick your early customers, partners, and investors. As if having people actually know what’s going on with your company, what you’re good at, and what you suck at can hurt you. I’ve found that’s not true.

You don’t have to lie to anybody. Almost everybody will understand that you’re a young entrepreneur with a young company. Be honest about where you’re at, what you’re struggling with, and what successes you’ve had. You’ll be surprised how people can tell whether or not you’re interacting with integrity. This goes for interacting both with team members and outsiders.

You Don’t Have to Work 120 Hours a Week

Another myth of the startup world is that, upon doing a startup, you’ll never do anything fun again until you exit. That if you’re not working yourself to death you’re not holding up your end of the entrepreneurial bargain. Bullshit. My guess is that we three co-founders are averaging around 60–70 hours of work a week, if you count evenings handling e-mail and the like.

Work as much as you want to work. If you find yourself working more, awesome. And if you find yourself working less, you’re probably not passionate about your job. Fix your interest. Don’t force yourself to overwork. Like I said above, your friends and family are hugely important to your success, so don’t ignore them!

Titles Matter

I thought titles were mostly for self-congratulations. That they were a relic of BigCo and had no place in startups. Our offer letters to our first three employees literally had titles of “Whatever You Want”. I thought this would differentiate us, that Michelle, Kirk, and Micah would find this to be impish and charming.

I was totally wrong. I still think titles can do damage internally in an organization. VP, SVP, EVP. What’s next? Mega VP? But they’re critical for two external reasons. First, they’re a mechanism for ensuring job security (i.e. on LinkedIn somebody can say COO instead of employee 1). Second, they’re important for establishing credibility with people outside of the company. Meeting somebody and saying, “Hi, I’m the COO of Keen IO” is very different than saying, “Hi, I work at Keen IO and I’m important, I SWEAR!”

Steal Good Ideas Liberally

I thought we’d have to come up with new ways to do everything. Turns out there have been a ton of smart people doing the entrepreneurial thing for years. Find some of them, turn them into mentors, and steal the ideas that make sense to you. I always knew that you shouldn’t reinvent the wheel when it comes to programming; somehow that wasn’t obvious to me on the non-technical side of the house.

Become a Storyteller

Nobody really cares about who you are, what you do, and what your company does (which is not to say that they don’t care about you) — at least not a first. So don’t bother coming up with the perfect way to communicate all the cool technical details behind your product. Just tell a story that people can emotionally connect with. All you need to do is make your audience viscerally feel what you want them to feel.

Figure Out How to Communicate Momentum

I’m following my own advice from above by shamelessly stealing this from Bart Lorang, CEO and founder of FullContact. He told us this in the context of raising money from investors, but it really works everywhere. If you can figure out how to craft a story of your momentum, you win. It could be users: “We had 500 signups last year and in this quarter alone we’ve got 2,000.” It could be dollars. Or it could be just a feeling: “Any time I introduce myself to somebody, they’ve heard of my company.” As I said above, tell a story. Make someone feel like they’re being swept up in a tidal wave of inevitable success.

Take Breaks and Enjoy It

I cannot believe it’s already been over a year since we started. It’s gone by amazingly fast. Fortunately, I’ve taken the time during the year to reflect on my experiences. By doing so I’ve been able to remember details that I’d probably forget otherwise.

I’m actually feeling kind of melancholic as I write this. I’m never again going to experience a year like this, even if I found a whole new company. There’s nothing like your first time through. So don’t move so fast that you forget to look backwards. And don’t be so forward thinking that you forget to celebrate past successes.

Give Back

Like I said before, you’re not alone in this business. People are going to help you. Reciprocate! Be available to give others advice. Share what you’re learning with Twitter, Facebook, or a blog. Go to events in your community and offer your time to those who could benefit from it. Share your code on GitHub or make your favorite open-source library better. Don’t isolate yourself!

Stay Connected

This community we’re all a part of is amazing. Take advantage of it. Offer your time and help with no promise or guarantee of payback. You’ll be amazed at how well it will work for you.

To that end, if I can be helpful in any way, please let me know. Follow me on Twitter. Ask anything. If I can help, I’ll try!