1460: Knowing When It's Time to Move On by Ryan Hoover on Entrepreneurship

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[00:00:30] [SPEAKER_01]: This is Optimal Work Daily.

[00:00:32] [SPEAKER_01]: Knowing When It's Time to Move On by Ryan Hoover of Ryanhoover.me

[00:00:38] [SPEAKER_01]: Next week I will be leaving my full-time role at Playhaven in one of the most expensive cities in the world, by choice.

[00:00:46] [SPEAKER_01]: I'm paid well, the company is growing and I work with an amazing team of friends.

[00:00:51] [SPEAKER_01]: I still ask myself, what the f*** am I doing?

[00:00:54] [SPEAKER_01]: Here's my story.

[00:00:55] [SPEAKER_01]: I moved to San Francisco to join Playhaven as number 10 nearly three years ago.

[00:01:01] [SPEAKER_01]: 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.

[00:01:11] [SPEAKER_01]: But honestly, I had no idea what I was doing and soon I found out the team didn't either.

[00:01:16] [SPEAKER_01]: We had a product with traction but revenue and adoption were nearly stagnant.

[00:01:21] [SPEAKER_01]: We needed to change something.

[00:01:22] [SPEAKER_01]: 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.

[00:01:30] [SPEAKER_01]: Layoffs were imminent.

[00:01:32] [SPEAKER_01]: I had a conversation with Andy over beers shortly before the layoffs.

[00:01:36] [SPEAKER_01]: He told me what was coming and that I might be out of a job in a few weeks.

[00:01:39] [SPEAKER_01]: What had I done?

[00:01:41] [SPEAKER_01]: I moved from my comfortable hometown to this unfamiliar city to join a dying start-up.

[00:01:46] [SPEAKER_01]: I guess I'll just ride this out and move back home, I thought.

[00:01:49] [SPEAKER_01]: But I survived.

[00:01:51] [SPEAKER_01]: The company downsized a few weeks later and I sadly said goodbye to my friends and coworkers as they packed their belongings.

[00:01:58] [SPEAKER_01]: And then there were six of us.

[00:02:00] [SPEAKER_01]: Fast forward three months, things begin to pick up.

[00:02:03] [SPEAKER_01]: We set out on a new inspiring vision.

[00:02:06] [SPEAKER_01]: The team was excited.

[00:02:07] [SPEAKER_01]: We put our heads down, scrapping nearly all existing code to rebuild the product.

[00:02:12] [SPEAKER_01]: As the sole product manager, I worked with a small team of five engineers.

[00:02:16] [SPEAKER_01]: It was largely a collaborative effort.

[00:02:18] [SPEAKER_01]: It had to be.

[00:02:19] [SPEAKER_01]: In between answering support requests, sending the occasional marketing email and other miscellaneous obligations,

[00:02:25] [SPEAKER_01]: I was responsible for defining the user experience, creating wireframes for the new dashboard.

[00:02:30] [SPEAKER_01]: I had done similar work but nothing at this scale.

[00:02:33] [SPEAKER_01]: I had to learn on the job and fast.

[00:02:36] [SPEAKER_01]: We made great progress thanks to an exceptional, hungry engineering team.

[00:02:40] [SPEAKER_01]: But still, the revenue was almost non-existent as the clock continued to tick.

[00:02:44] [SPEAKER_01]: We set a goal to do a private launch at Casual Connect in July of 2011.

[00:02:49] [SPEAKER_01]: The preceding month was hectic and thrilling.

[00:02:52] [SPEAKER_01]: There were long nights of excruciating pain, but passion is a powerful drug that can get you through hard times.

[00:02:58] [SPEAKER_01]: Rushed to bring the product into a usable state, strapped with few resources,

[00:03:03] [SPEAKER_01]: I, a mostly non-technical person, set up a local environment of the dashboard we were building and began squashing bugs.

[00:03:09] [SPEAKER_01]: Each GitHub commit delivered a rush of dopamine and satisfaction of progress.

[00:03:15] [SPEAKER_01]: It was 2 am the night before an important demo with a large client.

[00:03:19] [SPEAKER_01]: Without a QA team or even a single QA person, I hammered on the product late into the night,

[00:03:25] [SPEAKER_01]: uncovering and sometimes fixing more bugs.

[00:03:28] [SPEAKER_01]: It was incredibly unscientific, but we didn't have time for process.

[00:03:32] [SPEAKER_01]: We just had to get done.

[00:03:34] [SPEAKER_01]: Eventually, the product was delivered in a usable state and we landed our first big client.

[00:03:39] [SPEAKER_01]: This was huge and we celebrated our first major win.

[00:03:43] [SPEAKER_01]: Since our humble beginnings, the team has grown to 85.

[00:03:47] [SPEAKER_01]: We've acquired several thousand customers generating multi-million dollar revenues.

[00:03:51] [SPEAKER_01]: We're operating in a growing market with an amazing vision that I strongly believe in to this day.

[00:03:56] [SPEAKER_01]: Things are going well.

[00:03:57] [SPEAKER_01]: So why leave a good thing?

[00:04:00] [SPEAKER_01]: As I've shared before, my priority is to learn.

[00:04:03] [SPEAKER_01]: I've grown a ton in the past three years, especially during times of discomfort when I am challenged the most.

[00:04:10] [SPEAKER_01]: My time at Playhaven has taught me so much.

[00:04:13] [SPEAKER_01]: Methodologies for discovering what people really want.

[00:04:16] [SPEAKER_01]: The importance of building the right, minimal features.

[00:04:19] [SPEAKER_01]: Processes for bringing an idea to market.

[00:04:22] [SPEAKER_01]: How to scale a company.

[00:04:23] [SPEAKER_01]: The criticality of hiring the right people and building an aligned culture.

[00:04:28] [SPEAKER_01]: And more.

[00:04:29] [SPEAKER_01]: But I'm ready for my next challenge, eager to accelerate my learning.

[00:04:32] [SPEAKER_01]: My friend Nathan Bashaw recently told me, quote,

[00:04:36] [SPEAKER_01]: When you look back at yourself six months from today and don't feel embarrassed by your naivete, there's a problem.

[00:04:42] [SPEAKER_01]: That means you're not learning, growing, end quote.

[00:04:46] [SPEAKER_01]: As the company has grown, my role has transitioned into more specific areas of focus.

[00:04:51] [SPEAKER_01]: We've also hired a UX designer to relieve many of the responsibilities and fun challenges that I used to tackle.

[00:04:57] [SPEAKER_01]: In short, my role has become more specialized from my generalist roots.

[00:05:02] [SPEAKER_01]: But if I am to be honest with myself, I've lost passion for the market and the industry we're in.

[00:05:07] [SPEAKER_01]: I attempted to remedy this taking a long overdue two-week vacation three months ago, but the passion didn't return.

[00:05:14] [SPEAKER_01]: Over the years, my interest in video games has dwindled.

[00:05:17] [SPEAKER_01]: I grew up obsessed, microing marines in Starcraft hours at a time,

[00:05:22] [SPEAKER_01]: throwing profanities after getting disconnected in the middle of a heated Team Fortress Classic match,

[00:05:27] [SPEAKER_01]: and blasting grunts on Halo into the AM.

[00:05:30] [SPEAKER_01]: Today I rarely play even casual two-minute distractions on my iPhone.

[00:05:35] [SPEAKER_01]: Instead, I invest in myself, reading, writing, and working on side projects and experiments.

[00:05:40] [SPEAKER_01]: Today I have strong ambitions to build a product that I am the consumer of.

[00:05:44] [SPEAKER_01]: If you follow my writing, you may have noticed I never write about the industry I work in, gaming.

[00:05:49] [SPEAKER_01]: This is very telling.

[00:05:51] [SPEAKER_01]: Additionally, I am not a game developer nor do I have the motivation to become one.

[00:05:55] [SPEAKER_01]: People that build products for themselves have a tremendous advantage because they are their own user.

[00:06:01] [SPEAKER_01]: They don't have to get inside the user's head to understand the problem.

[00:06:04] [SPEAKER_01]: Their ability to persevere is strengthened by a motivation to solve their own problems.

[00:06:09] [SPEAKER_01]: Despite these feelings, the decision was far from easy and difficult to tell my friend and boss.

[00:06:14] [SPEAKER_01]: I could barely utter the words I'm leaving.

[00:06:16] [SPEAKER_01]: I cried. It's still hard to swallow.

[00:06:20] [SPEAKER_01]: But deep down, I know it's the right move for me.

[00:06:24] [SPEAKER_01]: I'm grateful for the opportunities I've been given, the support from my friends and mentorship from those in the entrepreneurial community.

[00:06:30] [SPEAKER_01]: You know who you are. I have many to thank.

[00:06:33] [SPEAKER_01]: As I spend my final days at Playhaven and think about my next adventure,

[00:06:37] [SPEAKER_01]: I refer to these questions as I evaluate new opportunities.

[00:06:41] [SPEAKER_01]: Is this really what I want to do?

[00:06:42] [SPEAKER_01]: Am I strongly passionate about the product, market and vision?

[00:06:47] [SPEAKER_01]: Will I be challenged, learn and grow to my full potential?

[00:06:51] [SPEAKER_01]: I hope others can learn from my experience and feel encouraged to find their passion,

[00:06:56] [SPEAKER_01]: reflect on their personal goals and take a chance on themselves.

[00:07:04] [SPEAKER_01]: You just listened to the post titled Knowing When It's Time to Move On by Ryan Hoover of ryanhoover.me

[00:07:10] [SPEAKER_01]: This show is sponsored by BetterHelp.

[00:07:13] [SPEAKER_01]: We're all marveled at how quickly kids learn and that sense of wonder meant they have while doing it.

[00:07:19] [SPEAKER_01]: But as adults, sometimes we lose that curiosity.

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[00:07:37] [SPEAKER_01]: therapy can be a great tool for setting boundaries, learning new skills,

[00:07:40] [SPEAKER_01]: and ultimately becoming the best version of yourself.

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[00:07:47] [SPEAKER_01]: It's entirely online, designed to be convenient, flexible and suited to your schedule.

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[00:08:02] [SPEAKER_01]: Visit betterhelp.com slash workdaily today to get 10% off your first month.

[00:08:07] [SPEAKER_01]: That's BetterHelp, H-E-L-P dot com slash workdaily.

[00:08:12] [SPEAKER_01]: And a big thanks to Ryan.

[00:08:14] [SPEAKER_01]: In addition to being the founder of Product Hunt,

[00:08:17] [SPEAKER_01]: he's also an investor at Weekend Fund.

[00:08:20] [SPEAKER_01]: The website is weekend dot fund.

[00:08:22] [SPEAKER_01]: Over there, he and his partner write checks from $75,000 to $200,000

[00:08:27] [SPEAKER_01]: for early stage startups around the world

[00:08:30] [SPEAKER_01]: and across consumer and business to business products and services.

[00:08:33] [SPEAKER_01]: They help founders with product, community building and more.

[00:08:37] [SPEAKER_01]: So if you're building something ambitious, they're the guys to talk to.

[00:08:41] [SPEAKER_01]: Again, you can check that out at weekend dot fund.

[00:08:44] [SPEAKER_01]: And Ryan is featured across a couple of our shows,

[00:08:47] [SPEAKER_01]: so if you like his style and this idea of blogs being narrated to you for free,

[00:08:51] [SPEAKER_01]: check out our other shows by searching for Optimal Living Daily, wherever you're hearing this.

[00:08:56] [SPEAKER_01]: And that should do it for today.

[00:08:58] [SPEAKER_01]: Thanks so much for being here and for listening all the way through.

[00:09:01] [SPEAKER_01]: And I'll be back with you tomorrow for the Monday show where your Optimal Life awaits.