Nationwide Expansion… Fuck me. Chapter 3

The Struggle Is Real

Hey there. Still grinding i see… Same here. Sorry for skipping last month, but I’ve been swamped. I’ll tell you why in a sec.

This month I want to talk about the struggle. Not failure. Failure is conclusive. The struggle is shapeshifting, perilous, stressful. Yet you can’t ‘win’ without overcoming hardship.

Bad news, roadblocks, missed opportunities, stupid mistakes… all part of startup life. A founders’ attitude toward these inevitabilities can make or break a startup. I know because I’ve seen both sides of this coin.

The easiest way to overcome hardship is to embrace it as inevitable. That hardship was all part of the plan, right? You knew this wasn’t going to be easy.

Optimism (and action) in the face of failure is the key to overcoming hardship. Embrace the idea that a problem is just an opportunity that has yet to present itself. Stay positive on the outside, even if you’re hurting inside.

If it CAN be done, YOU will do it.

What struggles are we facing right now? Let me tell you. You know that TV “Bazillion Dollar Club” I’ve been going on about? Well it got cancelled after the first fucking episode. All network TV shows that premiered that week bombed thanks to Netflix and the like. I can’t hate though ‘cause I love Netflix.

The producers are confident that the show will get picked up by a different network. I am too… the first episode was pretty damn great. Still, it could be a few months before our episode sees the light.

I took a pretty big hit mentally from the cancellation. I felt it more than anybody else on my team. I had spent a ton of time and effort working on the show. To be honest, I had high expectations. So high, we planned our expansion strategy around the premier of our episode. . I leveraged the show to raise funds, hire talent, and make partnerships… Whoops.

I heard the news the day before I left for a weekend kayaking/camping trip with my girlfriend. I used the time to get my head straight, have fun, and try to relax. My GF is super supportive, and I came back to work ready to rock. If I didn’t get out of town, I am not sure I would feel as good writing this.

My takeaway: If you are in crisis mode and can’t suck it up in front of your team, remove yourself for a hot minute. Get your head right. Talk about your feelings with people who love you. Put yourself in smile inducing situations. An overnight camping trip did the trick for me.

So what do we do now?

We were planning on expanding to NYC right after the show. Thats not happening anymore. We’ll cut our burn rate as much as possible and go back to building a business like a normal startup. A normal startup that didn’t have have a reality show fall into it’s lap. I gave everybody on my team the opportunity to trade in a salary cut for more equity. There are a few key tenants of this offer that make it possible, and not a negative signal.

  1. First and foremost, my team believes in what we are doing. If they were iffy on the whole thing, this would have backfired hard.
  2. I offered this opportunity to everybody. Nobody got singled out.
  3. We are not desperate for money. I have a mind only for reduced burn to buy time for growth and more fundraising. This makes number 4 possible.
  4. It is optional. I am not forcing anybody to take a pay cut.
  5. As a startup, most of my employees will receive pay bumps post series A financing. This plan is still intact. Thus, the pay cut is temporary, but the equity increase is forever.

As for our expansion plan, we had to shift it a bit. We were rushing like crazy to launch our new website and mobile app by the time the show aired. This would have led to bugginess due to lack of testing. So, we extended our deadline, but kept the sense of urgency. This way, our V2 can be great… not merely available. This will be our graduation from beta to beautiful.

We will open up our platform to be useable anywhere. No more ‘Kickstarter Expansion Method’. We will do little tests in various cities to find the lowest customer acquisition costs. We put everything we learned with our MVP into version 2. Every marketing move we make should be more effective with a kick-ass product to back it up.

So… its time to do the hustle! There are new territories to explore. Balls-out campaigns to create. Lessons to learn. Mistakes to make. Users to delight, revenue to generate. Oh yeah, and funds to raise.

I will be opening up a new funding round after the holidays. Fundraising is my strong suit, so I am pumped for the challenge. This past week was the single best week for revenue in Roost’s history. We more than doubled our run rate in the last month and a half.

You can feel the “fresh start” vibe in our office. Things are changing. There will be more struggles, but our team will overcome.

Like this post? Share it with an entrepreneur in your life who is in the trenches.

Stay tuned for Chapter 4: “Still Haven’t Thought of the Title Yet”.

New stories will be released monthly.

Oh, and if you have or need some space to rent, stroll on over to and be super rad.