3 Things I Learned Bootstrapping In 2016

As I’m sure it’s been for everyone, 2016 has been a helluva year. I’ve learned a lot working on my startup, Handstand, and thought I’d highlight three learnings that might be helpful for others building companies of their own.

In 2016 I took a leap. After the very first week of the year, one in which I learned I was being laid off along with the rest of my company, I spent the majority of the year working on my own bootstrapped startup.

I’ve learned a lot, failed many times, and realized how much I love the craziness of building a business.

What started as a fun side project has turned into my career (for better or worse!). At Handstand, we build adventure events for the public and custom team building events for companies. This year set the foundation for a big 2017 with successful events in San Francisco, Seattle, DC, and Boston.

I wanted to share three specific learnings from this first full “all-in” year in case others may be having parallel experiences or thinking of starting something.


1. This Shit Is Hard

There’s just no way around it. This was both the most rewarding and most frustrating year of my professional life.

I’ve had days this year where it felt like I couldn’t do anything right. Sponsors rejecting me, people not being flexible with gameday venues, zero signups. Days with that trifecta and more 100% happened this year.

But the most important thing is to just keep going. Pick back up, keep pounding, and give it another shot.

No one has the answers. It’s up to us to solve these problems. How do we get the right sponsors excited, involved, and paying us for that value? How do we find the absolute best places to start and end the day to delight our players? And how in the world do we get players in the first place? Woof. Breathe. Try not to freak out, but these three questions basically incapsulate the larger question of “How do we build a successful event?”

We ended up finding sponsors, getting venues to host us, and attracting an amazing community of people to play. The difficulty makes solving these problems (and like a million others) taste so sweet. And it’s why when they get solved, I believe in the answer with a degree of certainty that can’t be matched when someone else tells me how to do things (and gives me the answer).

But the persistence of things being hard is something that I’ve come to realize is inevitable and omnipresent. There will never be a time where I’ll think this is easy. And that’s okay. I don’t think I’d enjoy it any other way.

2. Always Be A Beginner

One of the things I’ve realized I like the most in my work is finding things I either a) have never tried or b) am knowingly not good at and trying them.

Growing up, I feel like I was always encouraged to try things. Music, sports, acting. Every kid gets involved in things and then figures out what they enjoy and what they’re good at and gets naturally pushed or pulled into those activities.

Doing that with new software programs, marketing strategies, and sales techniques feels very similar. Except this time, I’m embracing the experience of being a newbie (didn’t enjoy being bad at art class nearly as much).

Part of this has been a mindset of mine. In the last few months, we’ve turned a good amount of our focus to working with companies to do custom scavenger hunts for them for team building and as a part of their onboarding of new hires (speaking of, reach out if you want to chat about this for your company :).

At this point, my role is sales. Find opportunities for us and close the ones where there is a good fit. I’ve always had sales be a part of my job at Davidson, Curious, and Lovely, but this is the first time I’ve explicitly been responsible for making a sale and exchanging services for dollars.

Of course when I started out I thought I’d just crush it no problem and everyone would want what we have to offer. Not so much. After a few attempts, I realized I could just humble myself and help myself a lot. I’ve read Traction, Predictable Revenue, Getting to Yes, and started having meetings with friends who are fully in sales to understand best practices better. Not only is choosing to be a beginner at sales intellectually stimulating, I’m actually getting better at it.

Part of this initial uptick in learning and success has just been embracing failures as learnings and iterating, building, and trying new things. I think this is an attribute I want to keep with me throughout the entirety of my professional career and even in my personal life: never be comfortable with what I know. There’s always more to learn and new levels to get to. Being bad at something or being a beginner is just the start to what could be a long journey to being an expert.

3. Nothing Replaces Sweat / No Days Off

There are no shortcuts in this. One of the quotes I really like that has stuck with me is “If you work hard for long enough, you might be lucky enough for someone to call you an overnight success.”

Just putting in hustle and effort every day keeps us on a path to do better tomorrow than we did today. There is simply no technique, hack, or easy way to replicate what comes with just purely consistent application. It’s nice when there’s clear examples of hard work paying off, but I’ve realized that working on Handstand is similar to the mindset of the training I used to do for soccer. There’s so much time put in, that you have to enjoy the hard work and the process.

This learning does not mean that I don’t take any days off. What I mean by No Days Off is it feels like I can’t have an “off” work day. Maybe it should be No Off Days instead. If I’m not sharp, I’m actively holding the company as a whole back. Those days that used to happen where you hang a little longer at the water cooler (or whatever most startups have now — pool table?) just can’t happen anymore. I literally installed an app on my desktop called Self Control that lets me block certain websites from my own browser for a period of time I choose. Gotta shut Facebook out sometimes.

Sustained pure and constant hustle and incessant focus every day are impossible. But holding them as the standard and striving for that perfection is what gets me as close as I can to achieving my potential.


Who knows what 2017 will hold. I just know I’ll carry these three learnings with me and hopefully be better next year than I was this. After all, if I just get better every year, then eventually, I might be good at this!