August 8, 2013

Knowing When It's Time to Move On

Next week I will be leaving my full-time role at PlayHaven in one of the most expensive cities in the world - by choice. I’m paid well, the company is growing, and I work with an amazing team of friends. I still ask myself, “What the fuck am I doing?”

Here’s my story…

I moved to San Francisco to join PlayHaven as #10 nearly three years ago. Silicon Valley has always attracted this native Oregonian and the opportunity to join the visionary Andy Yang in the booming mobile gaming space made my decision a no-brainer. But honestly, I had no idea what I was doing. And soon I found out, the team didn’t either.

We had a product with traction but revenue and adoption were nearly stagnant. We needed to change something. Those first five months were some of the most exciting yet scary times in my life, debating what to do next as our cash reserves dwindled. Layoffs were imminent.

I had a conversation with Andy over beers shortly before the layoffs. He told me what was coming and that I might be out of a job in a few weeks. What had I done? I moved from my comfortable hometown to this unfamiliar city to join a dying startup? “I guess I’ll just ride this out and move back home,” I thought.

But I survived. The company downsized a few weeks later, and I sadly said goodbye to my friends and coworkers as they packed their belongings. And then there were six of us.

Fast-forward three months, things began to pick up. We set out on a new, inspiring vision. The team was excited.

We put our heads down, scrapping nearly all existing code to rebuild the product. As the sole product manager, I worked with a small team of five engineers. It was largely a collaborative effort. It had to be. In between answering support requests, sending the occasional marketing email, and other miscellaneous obligations, I was responsible for defining the user experience, creating wireframes for the new dashboard. I had done similar work but nothing at this scale. I had to learn on the job and fast. We made great progress thanks to an exceptional, hungry engineering team, but still, revenue was almost non-existent as the clock continued to tick. We set a goal to do a private launch at Casual Connect in July of 2011.

The preceding month was hectic and thrilling. There were long nights of excruciating pain but passion is a powerful drug that can get you through hard times. Rushed to bring the product into a usable state, strapped with few resources, I (a mostly non-technical person) setup a local environment of the dashboard we were building and began squashing bugs. Each GitHub commit delivered a rush of dopamine and satisfaction of progress.

It was 2 A.M., the night before an important demo with a large client. Without a QA team (or even a single QA person), I hammered on the product late into the night, uncovering and sometimes, fixing more bugs. It was incredibly unscientific but we didn’t have time for “process”. We just had to Get Shit Done. Eventually, the product was delivered in a usable state, and we landed our first big client. This was huge, and we celebrated our first major win.

Since our humble beginnings, the team has grown to 85. We’ve acquired several thousand customers, generating multi-million dollar revenues. We’re operating in a booming market with an amazing vision (that I strongly believe in to this day). Things are going well.

So why leave a good thing?

As I’ve shared before, my #1 priority is to learn. I’ve grown a ton in the past three years, especially during times of discomfort when I am challenged the most.

My time at PlayHaven has taught me so much. Methodologies for discovering what people really want. The importance of building the right (minimal) features. Processes for bringing an idea to market. How to scale a company. The criticality of hiring the right people and building an aligned culture. And more.

But I’m ready for my next challenge, eager to accelerate my learning. My friend, Nathan Bashaw recently told me:

When you look back at yourself six months from today and don’t feel embarrassed by your naiveté, there’s a problem. That means you’re not learning, growing.

As the company has grown, my role has transitioned into more specific areas of focus. We’ve also hired a UX designer to relieve many of the responsibilities and (fun) challenges I used to tackle. In short, my role has become more specialized from my generalist roots.

But if I am to be honest with myself, I’ve lost passion for the market and industry we’re in. I attempted to remedy this, taking a (long overdue) two week vacation three months ago but the passion didn’t return. Over the years, my interest in video games has dwindled. I grew up obsessed, micro’ing marines in Starcraft hours at a time, throwing profanities after getting disconnected in the middle of a heated Team Fortress Classic match, and blasting grunts on Halo into the A.M. Today, I rarely play even casual, 2 minute distractions on my iPhone. Instead, I invest in myself, reading, writing, and working on side projects/experiments.

Today, I have strong ambitions to build a product that I am the consumer of. If you follow my writing, you may have noticed I never write about the industry I work in: gaming. This is very telling.

Additionally, I am not a game developer nor do I have the motivation to become one. People that build products for themselves have a tremendous advantage because they are their own user. They don’t have to “get inside the user’s head” to understand the problem. Their ability to persevere is strengthened by a motivation to solve their own problems.

Despite these feelings, the decision was far from easy and difficult to tell my friend and boss. I could barely utter the words, “I’m leaving.” I cried. It’s still hard to swallow but deep down, I know it’s the right move for me.

I’m grateful for the opportunities I’ve been given, the support from my friends, and mentorship from those in the entrepreneurial community (you know who you are). I have many to thank.

As I spend my final days at PlayHaven and think about my next adventure, I refer to these questions as I evaluate new opportunities:

  • Is this really what I want to do?
  • Am I (strongly) passionate about the product, market, and vision?
  • Will I be challenged, learn, and grow to my full potential?

I hope others can learn from my experience and feel encouraged to take a chance themselves and reflect on their own personal goals.

If you’ve gone through similar challenges, I’d love to hear from you. Email me at

You can also follow my journey on Twitter (@rrhoover) or subscribe to my email list

Read more of my writing here. Or subscribe to follow along:
More Writing by Ryan