Magnificent failures, hand made video game cheat books and the absurdity of startups: An interview with Ryan Hoover

Talking shop

Ryan Hoover is one of the most inspiring (and relentless!) writers in the world of startup. He’s published over 150 essays on startups and digital product design, and he’s been a real inspiration for our team at Makeshift over the past year.

We thought it would be fun to turn the tables on him and ask him some questions about his experience building startups out in San Francisco.

Hi Ryan, thanks so much for taking the time to chat with us. You're clearly incredibly passionate about startups, and starting up. What led you to the startup space, and why do you get so excited about early stage companies?

I’ve always been interested in entrepreneurship, largely influenced by my father who has been a successfully self-employed business owner since his mid-20's.  Early on, I started several small entrepreneurial side-jobs.  When I was 10, I managed candy vending machines and sold hand-made video game cheat books at my father's retail video game store.  Later, I learned front-end web development and built a (hideous and $10 profitable) joke website called Operation Laugh.  While in high school I bought and sold over $150,000 of electronics on eBay, pocketing the margin.

But my first real startup experience started during my senior year in college when I interned at an IAC-backed company called InstantAction.  After graduation I joined as a marketer and quickly moved into product management.  The startup was a magnificent failure and fantastic learning experience. Three years ago, I moved to San Francisco to join PlayHaven and have since decided to move on to something new.

“The startup was a magnificent failure and fantastic learning experience.”

I can't see myself working at a larger company.  I enjoy the absurdity of startups -- the (almost irrational) hope of directly impacting a big change in peoples' lives.  I'd much rather have "high-high's" and "low-low's" than the "medium-medium's" of big businesses.  Ultimately my goal is to learn while building something I'm passionate about and startups are the best place for me to do that.

I love the idea of a 'magnificent failure.' Thinking about the time you spent at InstantAction, what would you say were the top two or three dangerous signals or behaviours you've learned to watch out for subsequently? Have you seen these issues crop up again in your work since then? And what advice do you have for our readers to try and avoid them?

Sometimes failure is the best vehicle for learning.  InstantAction was one of the best experiences I could have had as a green college grad.

Our critical misstep was a lack of focus. We tried to do too much, effectively building three businesses in one. We had a game engine (Torque), developed games in-house (InstantJam and other titles we never publicly announced), and built a gaming distribution platform.  Super ambitious but unrealistic to execute well all at once.  This also resulted in a misaligned company vision, leading to cross-team tensions as dependencies arose.

“We tried to do too much, effectively building three businesses in one.”

We failed to release products quickly to gather user feedback.  Customer interviews, usability studies, and other feedback mechanisms are incredibly valuable but nothing beats the learnings gathered from actual user behavior. 

Similarly, we over-engineered products.  It's very easy to build "cool" features that don't necessarily help your product grow, especially as a company gets fatter with resources.  Andy Johns had an excellent quote at the most recent Growth Hackers Conference, "More features does not necessarily mean more growth."  Saying "no" and killing features that don't work out should be expected.

Hmm. Interesting. There's probably a lot we could learn from that at Makeshift. We love building stuff, and it's often more fun to be shipping code than anything else.

So let's talk about some of your personal projects now. Tell us a bit about Startup Edition - why did you set it up, and what have been some of the best posts?

Startup Edition started with a tweet from my buddy Nathan Bashaw.  He pointed out a few tech bloggers that serendipitously wrote about the same topic on the same day.  

As an avid reader of startup-related content, I thought this would be a good way to encourage bloggers to write more, sharing their advice and stories collaboratively.  So we recruited a few people we respect and published the first edition with the name, Question Club, before changing it to the more fitting name, Startup Edition.

Above: The Startup Edition office. AKA Ryan’s apartment.

We've published over 25 editions and 150 essays since it began about six months ago.  A few of my personal favorite essays are:

That's a great list. Speaking of lists, one thing I have to ask is around tools - as you know we make tools for startups at Makeshift, and we're always looking for new inspiration and ideas. 

As someone who's regularly talking with all kinds of people in early stage companies what do you see as some of the most interesting and emerging new tools or types of tools? What stuff do you think is giving companies in your neck of the woods an edge?

I’m personally most interested in tools that address inefficiencies and improve team communication. A few of my personal favorites are:

  • Sqwiggle - There are several enterprise communication tools like Hipchat and Flowdock that create a better chat experience for businesses but Sqwiggle takes an innovative approach to team communication.  If Skype and Campfire had a baby, it would look like Sqwiggle.  The web or desktop app shows a video feed of each team member, 24/7.  Simply tap on a teammate to instantly start communicating with more fidelity and efficiency than traditional text chat.
  • Rapportive - To my surprise, some people still don't know about Rapportive.  This browser extension provides useful information within one's email inbox, including their profile picture, social profiles, past email conversations, and other contextual information.
  • Buffer - I'm a Buffer fanboy.  I use it daily to tweet links to interesting articles to maintain an active Twitter feed.  Every 1-2 hours, a tweet is sent from my "buffer," to continually engage with my audience.  It's dead simple. Just recently, they released a Business edition to provide more advanced features for enterprise customers.
  • PlayHaven - Ok, this one is self-promotional.  Soon after I joined PlayHaven three years ago, we relaunched the company and product as a "business engine for mobile games."  Marketers use our web dashboard to create and run campaigns in real-time inside their game without engineering resources or app updates.  We now have thousands of developers using our toolset to cross-promote their portfolio of games, reward players with virtual currency, sell purchasable content in-game, and more.  While we've focused on mobile games, Intercom provides similar promotion and CRM-type functionality for web apps.

Sqwiggle sounds intriguing, although a bit intense. Blend that with Peak for a full P2P panopticon! To conclude, and keeping with the future theme, I see you're leaving PlayHaven soon. What's next on a practical level, and what do you feel you still have to learn about starting up? 

My decision to leave PlayHaven wasn't easy.  I learned a ton at the successful startup as we've grown from 10 to 100 since I joined three years ago.  But ultimately, I'm optimizing for learning and feel now is the time to challenge myself with something new.  Fortunately, I'm in a position where I can take the time to find the right fit.  I have a lot more to learn about startups and have set a course to learn from other amazing entrepreneurs.

“I’m optimizing for learning”

In the meantime, I am investing more time in my blog, advising startups, and working on an exciting, unannounced project (subscribe to my email list to get the inside scoop).

Awesome. Thanks Ryan, and good luck with your next venture. From what we’ve heard on the down-low it’s going to be brilliant.

Ryan Hoover is Director of Product at PlayHaven, and his personal projects include Startup Edition, a network of founders and creative people from the world of startup and Product Hunt, an invite only group of product people on the hunt for inspiration. You can follow him on twitter @rrhoover or email him at