Goodbye, Giant Thinkwell

I just sent my final email as a tentacle of the Squid to the community in which I've been able to start my life as an entrepreneur.

Giant Thinkwell has been one of the biggest puzzle pieces of my life and it's been an incredible ride with a handful of really fun stories created along the way. Some of my favorites are the scantily clad Seattle Met recap, being voted Seattle's Best Startup Designer over the people I look up to, the larger than life War Rooms and getting to do a commercial with Sir Mix-A-Lot… oh right, can't forget about the stairway battles!

I have felt fortunate every single day to be a part of the Founders/TechStars family in Seattle and have enjoyed learning, growing, creating and being inspired in a way that I have never experienced before. That community is truly unique and special and I hope to find other ways to be a part of it.

If I could leave behind two things from this experience, they would be that you should be proactive in creating an environment and culture in which you thrive, and also the importance and value of brand, design and storytelling. I would argue that it is equally as important as a technology that functions, sometimes more valuable if you want to test assertions or even raise money without having the fully functioning technology, traction or data points.

What does leaving Giant Thinkwell mean for you and me?
I'm not sure if you've ever seen Lost, but in that show, there is a electromagnetic anomaly that builds up and must be released every 108 minutes or the entire world ends. That electromagnetic anomoly they are referring to is actually the creative energy that runs through my veins. I need to find projects to apply it to, so please, for the sake of all that exists, reach out and let me know what you're working on and where I can make it fun, colorful and loud!

So much to learn from this experience and bring to bigger and better things!




Had a pretty emotional moment yesterday when Andy Sack, Director of Founders Co-Op/TechStars made the announcement to the 2 dozen startups hacking away on this floor.

Trying to grasp the impact of Jobs's influence on not only EVERY single one of our desks but being largely responsible for creating the opportunity for all of us to be sitting in this room together following the dreams we have. 
Steve Jobs has definitely made his ding.


DeathMath - T.A. McCann

Huge thanks to T.A. for his insight and time given to the DeathMath team during Startup Weekend Edu! Over the course of TechStars and various startup events, I've heard hundreds of talks with incredible brain dollops of wisdom, yet am still inspired and educated when people like T.A. just continue to dish the good stuff. You can't be around these people and not understand why they are successful in life.

Oh yeah, watch this and get inspired! (Shot by the one and only Mike Folden)



This weekend was my 9th Startup Weekend and it never fails to re-energize! I was invited to mentor teams in helping them get the most out of the weekend, which can only be learned from experience. (It is indeed where Giant Thinkwell was birthed!)

Shortly after coming in on Saturday, I sat down to hear a pitch and was instantly visualizing its potential. Getting kids to learn through compelling gameplay. They called their app "DeathMath", where you go head to head with another player, represented as figures of history, and you kick each others asses through quickly solving math equations. The idea was intended to reach the kids that would rather engage in fun video games and not through boring academic content. 

The story and aesthetic wrapper that was told around the initial prototype was one of battle and violence. It was clear that this was an idea that would make some people uneasy, which I happen to favor myself. They had a super talented team too that understood mobile, gaming, fun and education (what more could you ask for?!) A great designer from Ubermind, working on mobile experiences for large brands, as well as a developer from the Microsoft X-Box team, another developer from Teachstreet and of course the man with the idea and business guy, also from Teachstreet. The only thing I felt they were lacking was some flavorful avatars to represent the historical figures and especially in their brutalized state. I saw an opportunity to help them out and make some noise.

Check out the weekend demo at - we'll definitely polish it up and get it native to the iPad with more avatars, more violence, and more academic development. 

Oh, did I mention it was posted to Reddit, and within a couple of hours made the front page with almost 2,000 upvotes and 200 comments? Tons of great feedback and tons of great hating! (told you there'd be uneasiness...)

Here are some screenshots: (Design is Joe Shoop / Avatars by me)

Here was our awesome team:

And lastly, this is an extra little something to say thanks to Mike Arrington for not only coming out to support and judge Startup Weekend EDU, which meant a lot to the Seattle community, but also a thank-you from team DeathMath for showing enthusiasm and support during the demo. Thanks Mike!



Mix 'n Match Assets




I recently picked up a Wacom Cintiq 21UX, which came just in time to crank out a handful of assets for Giant Thinkwell's latest game with Sir Mix-A-Lot. It consisted of about 4 dozen topical rounds where you get a chance to get to know Sir Mix-A-Lot and your friends a little bit better. The content was hilarious and needed a suitable visual to capture each round. I've used a Cintiq a bit in the past, but having this tool has easily increased my productivity by a good 300%, not to mention is faaarrr more enjoyable and awesome than even a normal Wacom Intuos tablet. If you are a digital artist or run a shop of creatives, do yourselves all a favor and invest. The productivity, quality and quality of life is worth a few extra pennies.

Seattle 2.0 - Best Startup Designer


(This is my recap of the last year and of the event.  I want to speak more to Design in my next post)

May 5th was one of the most defining and incredible nights in my existence to date. A few major things all came together in a split second for a poetic explosion of awesome. It started exactly one year earlier...

It was the 2010 Seattle 2.0 Awards and I was running around with Kevin Leneway and our baby Uncle Jesse on my iPad, still fresh to the Startup world just a few weeks after Startup Weekend. When we sat down for the ceremony, I listened in awe as Jonathan Sposato gave an incredible speech, followed by hearing nominees and names of people and companies I had never heard of before. Kevin was sitting next to me, pointing out each person, giving me a nutshell overview as he called out his speculation for who was taking home which award.. he only missed one! About half way through, the nominees for Best Startup Designer were read, and I instantly thought to myself, "holy s*#@, an awards show where Designers are recognized??" Before Jenny Lam's name was read to be the winner, I had a split second fantasy of my name being called and accepting the award. It was a silly fantasy that didn't last long for a few reasons. One, nobody knew who I was or had seen my work. Two, I wasn't a nominee and lastly, I fancied myself more of an Illustrator than a Designer. The night went on and I met a ton of great people that had all this buzz and excitement about them with being a part of this community.

It was at last year's event that Kevin and I spoke to Greg Gottesman of Madrona Venture Group and Andy Sack of the upcoming Seattle TechStars program and they convinced us to apply. Over the course of this last year, I got to collaborate and brand a number of organizations for Seattle's community, including Tech Cafe, Seattle TNT, Startup Weekend, a handful of TechStars teams, Brad Feld, Untitled Startup (now Simply Measured), DotORG, Geekwire and a few others.. it was with these projects that people got to know who I was and were excited to help me in my endeavors with Giant Thinkwell. 

Fast forward to a month ago or so when nominations were open for Best Startup Designer 2011. My Co-Founders, being some of my biggest supporters, spread the word and tried to get me voted in. Shortly after nominations closed, the 5 selected nominees were named and I was blown away that I was amongst the other 4! Matt Shobe, Tony Wright, Aviel Ginzburg and Jay Dokken are super heavyweight hitters with the Designer's label and it felt really great to even be considered in the bunch. From knowing these guys, I quickly conceded and just looked forward to the event, especially because Giant Thinkwell was given a table to present our demo for our upcoming game, Mix 'n Match.

Kevin and I worked around the clock, cranking out a game that only existed on paper, as well as all of the design and production for the physical booth. I don't know if you've ever seen an installation or booth from me before, but it'll never just be a table and computer or white tent. I find myself obsessing over the tiniest details and cram in as much as humanly possible to create the best experience I can. This time it included a fully animated game, banners, a Wheel-of-Awesome where winners got to spin for extra swag, including plush squids, squid neck-ties, toys I made at Funko, silkscreened posters, art prints, cut vinyl decals of our new brand and "Think Ink - Squid brain juice". I branded my iMac, decked the crew out w/ custom ties and to top it all off, Colleen, the girlfriend of our newest hire Kav brainstormed with me and built an 8 foot squid mascot of the Giant Thinkwell squid! 

The game got finished at 4:30pm, then we drove down to the space to set up at 5pm. The squid was getting the final hot glued pieces done in the back and I hadn't seen it since it was in armature phase.. When it came time for Danielle Morill of Twilio to present Best Startup Designer, she gave a fantastic and vital speech on the value of design in startups, which is only now starting to become a widely accepted practice amongst developers and business founders. She was opening the envelope and as my girlfriend Danielle was gripping my arm and then I heard it. It was this eery echoing call - "Kyle Kesterson!" ... My brain went cold and my eyes grew wide. I thought to myself, "ooooh man, I wish I planned on something to say..." It was a looong walk up to the front but nothing was coming to mind! I get about 2/3 the way up and I see thse creepy yellow glowing eyes start to sway to the front of the room. It was the squid! It was such an overwhelming moment trying to grasp that not only had I somehow achieved what I fantasized about a year earlier, but how every single piece of the puzzle all came together the second that I had seen the glowing eyes. I burst out and ran up to hug the squid! That was a moment of completeness. 

If you were to ask me after the acceptance what I had said, I couldn't tell you. I was numb. I remember walking on stage and hearing a faint whisper of my voice echoing into a sea of dimly lit faces. Videos of the speeches were posted the next day, so I got to go back and relive it and see just what DID come out of my mouth. I'm glad I managed to capture my gratitude to the startup community, Startup Weekend, TechStars and definitely the support of my lady, Danielle, but I completely blanked on a few very important people.

I really want to say that meeting Kevin Leneway has changed my life. He is one of the most brilliant, talented and genuine people I've ever met and I'm so blessed to be working by his side every day. Adam Tratt has also an incredible friend, supporter and balance to my creative craziness. Without those two, Giant Thinkwell would not exist today. Donald DeSantis, one of my best friends, introduced .. no, dragged me kicking and screaming to Startup Weekend, dragged me from Kirkland to Greenlake to move and delivered my ransom notes to Andy Sack to get into TechStars. He is extremely perserverant, influential and obsessed with getting better.. I'm stoked that he is now working full time at Giant Thinkwell. Marcelo Calbucci, Andy Sack, all the TechStars teams, Greg Gottesman, Scott Jacobson, Mike Folden, Adam Doppelt and the other Spoons, Jason Hills and so many others! Also The Root 42 has been a decade of growth and without that community, would probably not be making stuff, let alone doing it for a living.

Lastly, I have gotten incalcuable love, support and inspiration from my parents, Steve and Tamera. My mother's story is one that'll leave you in tears, followed by inspiration to take ANY leap. My dad's work ethic, dependability and kind heart is of an era that many of us can learn from. I love my parents more than anything and I most definitely would not be doing at all what I am doing or be who I am if they hadn't taken the incredible risks they took to get my brother and I out of our old lives. 

I feel overwhelmed with the blessings that I have received and aim to be a part of paying it forward. Thanks everyone!

Here are some more links about the event:

Xconomy: "Striptease Threats, Aggressive Shushing, Mascot Mania: Memorable Moments from from Seattle 2.0 Awards"

GeekWire: "A night at the Seattle 2.0 Awards: Watch the speeches of the 10 winners"

And finally, pictures!





Squid illustration by Ryan Tatum


Seattle Met feature


Really fun article written by James Ross Gardner about Giant Thinkwell in March's edition of the Seattle Met.

Photos by Michael Clinard (it was his idea to make me lose the pants...)

Read the full article here: This Product Will Change Your Life


Also featured in the magazine is Matthew Inman, the talented guy behind a little site known as Great interview here: Mr. Inappropriate

The Daily 11

Banner by Adam Laurie

A resolution for 2011 was to doodle every single day. It turns out that 4 of my friends had that same resolution, so we decided to put together a blog called 'The Daily 11'.

In the past, it's been known that us creatives claim that we will do a daily contribution and keep up with it, but alas life gets in the way and we fail.

We need some accountability, harassment & encouragement!

That's why Dan Savage, Adam Laurie, Mihai Cernusca, Bryan Perozo and myself have made a blood oath that we will indeed do at least one doodle, zombie or take one new picture and post it here each day. 3 strikes and we fail. Last man standing gets everlasting life.

Please feel free to harass, encourage and crit to give us the juices to follow through to the end of the year!


I will post all of my week's submissions at the end of each week here, but you can see all of ours posted daily on the other blog.

Check it out at

Here was my Jan 1st doodle of the 4 of them haunting me to DRAW!

K9 Rescue & Rehabilitation

My mom is awesome. Last September she turned her passion for dogs and her house into a full blown dog rescue. I've been there with as many as 33 dogs all housed at once! It's insane and takes a special set of parents to take on such energy, but they are doing amazing things for these "Green Mile" dogs that have days, or sometimes only hours left before getting euthenized.

Since September, she has rescued, rehabilitated and housed 116 dogs!

For Christmas, I spent some time to brand her and make her some business cards and a new website. I'm terrible at coding, so I used to help, which is just plain rad.

Please check out the new site,, and share via Facebook and Twitter. Sharing can save a life! :)

Giant Thinkwell goes to Hollywood!


I don't normally chat about Giant Thinkwell related things on my blog, but life after TechStars has been a freakin' blast! If you don't know by now, Kevin and I co-founded a company called Giant Thinkwell. Our first product is called 'Raising Hollywood' and deals with celebrity-endorsed social gaming. We just got back from a trip to Hollywood where we sat down with Soleil Moon Frye (Punky Brewster), Ashton Kutcher, JibJab's CEO Gregg Spiridellis and a handful more of really awesome people. It is way too damn exciting being an entrepreneur and there is just no way I could ever find myself clocking back in for somebody else. Oh and to answer the #1 received question that I've gotten since working on our first prototype game 'Raising Uncle Jesse', yes, we finally broke through and got to chat with John Stamos. (Thanks Nate!)


Kevin Leneway and I have been busting our asses on our new startup 'Giant Thinkwell' since March. It has been such an incredible journey up to this point and it's only gaining momentum. We've been blessed with the energy and support of our spouses, families, friends and the tech/investor communities in Seattle, LA and San Francisco. We truly appreciate each meeting, insight, introduction, investment, and support that each of them has given. Without it, Giant Thinkwell would not be doing close to what we're doing today. We have huge things on the horizon and are cranking away until our ideas are fully realized!

Thanks again for all of the love and support! Happy Thanksgiving.

Brad Felds Amazing Deals!

Today a caricature of Brad Feld that I did ended up on the front page of Tech Crunch. I recently gave about an hour of my time to the amazing Techstars duo of Deal Co-Op to help with some branding and another hour to caricature the legendary Brad Feld. It's been fun watching these guys explode over the last 2 months, can't wait to see what next year looks like for them!

More info:

Deal Co-Op

Brad Feld's Deal Co-Op

Tech Crunch article