Nationwide Expansion…Fuck me.


This is a look under the skirt of a recently funded, totally badass startup as we try to scale across America.

I’m having an adrenaline rush and anxiety attack at the same time…

Roost is only available in San Francisco right now (which was a major feat on its own). Limiting ourselves to SF makes it easier to control our marketplace. If an issue arises, we can be there to put out the fire in person. We know who our users are, and they know us… but this won’t scale. To scale this thing, we need to send our baby into the wild. The thought of this makes me all kinds of nervous, but to grow a company the bird must ‘leave the roost,’ so to speak.

My name is Jon Gillon, and I am the Co-Founder and CEO of Roost (think Airbnb for storage space). I must lead my team along the pot-holed path to success. I should be able to navigate through fires and flash floods, with neither map nor compass. I have my gut instincts, I understand my business and my customers, and I’ve surrounded myself with a talented team of problem-solvers. That should be enough… right? Right?!?

There is a phrase I find myself using more and more…

Educated Recklessness.

This phrase will be a theme in this multi-part expose on scaling a promising startup from the eyes of an untested CEO.

Educated Recklessness means the decisions we make are rarely derived from conclusive data. I wish this wasn’t the case. But, we can’t analyze data when there is no data yet to analyze.

So, we must take risks. Educated risks, we hope. But when speed is crucial, and you are trying to build something brand new, decisions can feel reckless.

My super power is making quick decisions. I trust my gut and my team. I learn from my mistakes and never make the same mistake twice. I’ve made a ton of mistakes, though. I failed 5 businesses in college. But the more mistakes I have made, the less I will make down the oh-so-bumpy road.

This series is my attempt to be helpful to others, as so many others have been helpful to me.

I want you to join us as we attempt to scale up our peer-to-peer marketplace. It is now late July, 2015. Roost will be on SyFy’s new documentary series, “The Bazillion Dollar Club” in late October. TV cameras have been following us around for the last 6 months. They filmed us as we navigated through 500 Startups Accelerator program and beyond.

Our plan is to sync our hour long episode with our nationwide expansion and app launch. If we properly capitalize on this exposure, Roost will blast off.

I will do my best to be as honest and transparent as I can be as we explore these new lands. The goal is for you to derive as much value as possible from our successes and failures. Please use these ‘learned-the-hard-way’ lessons as you build and expand your own ventures.

Topics I’ll cover:

1) Fundraising and use of funds,

2) Recruiting and use of recruits,

3) Balancing supply and demand in new cities,

4) Thought processes (or lack thereof) behind major strategic decisions,

5) Execution, execution, execution.

Stay tuned for Chapter 2: “Getting Our Sh*t Together”.

New stories will be released monthly. To follow along on this adventure, do ALL OF THESE THINGS:

  1. Follow me here on Medium

2. Share this post on every social media channel you know.

3. Follow me on twitter @gonjillon

4. Follow Roost on twitter @roost

5. Grab a tasty beverage and watch us bumble and stumble our way to the unicorn club.