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Phil Gordon started Seattle-based Chatbox in 2014. (Chatbox Photo)

After his first startup, Phil Gordon spent about 10 years as a professional poker player. Four more startups later, it’s clear that the tech veteran is not done gambling on his entrepreneurial chops.

Gordon is now the founder and CEO of Chatbox, an integrated messaging ecosystem where businesses and customers seamlessly exchange real-time information to achieve instant results.

“I lead a small, but extremely talented team building a technology that gives businesses everything they need to create, automate, and integrate hyper-personalized customer experiences at scale,” said Gordon, who is GeekWire’s latest Geek of the Week. “Although my background lies in computer science, at my core, I’m an entrepreneur.”

During his time playing poker, Gordon achieved celebrity status as a World Poker Tour champion, the author of four books, the host of Bravo’s “Celebrity Poker Showdown,” and as an ESPN poker analyst.

“To the outside world, being a professional poker player seems exciting, glamorous and full of huge cash payoffs,” he said. “The startup world can seem very similar.  One might think any college kid in a hoodie could launch the next unicorn from their parent’s basement, but the truth couldn’t be further from that. Just like being a professional poker player, running a startup takes a tremendous amount of hard work, observation, selective aggression, resilience and plain old luck.”

The former CEO and founder of Seattle-based Jawfish Games, Gordon said that in his early years not a day went by where he wasn’t committing code. But nowadays, his engineering team locks him out of the code base.

“Most of my time is spent with customers, potential hires and focused on product vision,” Gordon said. “I really miss my integrated development environment days. Over the years, it’s become crystal clear to me how important it is to surround yourself with the right people. Your teammates, partners, advisors, customers, investors and even your vendors dramatically influence the world you are shaping. Choose carefully and intentionally, and your course will be infinitely easier to navigate.”

In his free time, Gordon is an avid golfer, tennis enthusiast and the family chef.

“I’m easy money in ping pong and pool, and I’m a proud father of two amazing boys and am fortunate to work side-by-side with my wife, who serves as our VP of operations,” he said.

Learn more about this week’s Geek of the Week, Phil Gordon:

What do you do, and why do you do it? “As a computer scientist and entrepreneur, it’s in my DNA to generate ideas and strategically solve problems that improve how businesses work. Today, we’re living in an on-demand world with standards set by Amazon, Netflix and others, and I started to notice a gap in consumer expectations and the delivery of personalized messaging from businesses. Businesses collect all this data about their customers but then don’t seem to do much with it, often acting as if they don’t even have it. Anyone who has ever dealt with customer service knows what I’m talking about. Companies struggle to deliver that ‘personal touch’ at scale because historically automation has meant sacrificing personalization. I believe that trade-off no longer holds true — you now CAN have the best of both worlds. I am passionate about what we are creating with Chatbox. We are setting a new standard for enterprises and medium-sized businesses to deliver on-demand, personalized customer experiences at scale across texting, chat and social channels.”

What’s the single most important thing people should know about your field? “There is a gale-force wind blowing at the back of the ‘messaging ecosystem.’ Eighty percent of Fortune 1000 CIOs intend to deploy messaging-based applications to their customers by 2020, and very few of them already have. The other 20 percent will as well to meet consumer demand. Despite the chatbot ‘hype,’ messaging isn’t really about conversations, it’s about results.”

Where do you find your inspiration? “My inspiration stems from a few places. It comes from clients that are constantly searching for better ways to service customers and looking for a technology to evolve with consumer demands. I obsess over creating things that work the way they should and get energized by exploring big ideas with smart people. Not to mention, I’m super competitive and get just as tilted over losing $2 in a friendly wager as I would over losing $2,000. Lastly, I’m a big fan of Jason Lemkin. If I’m ever looking for a shift in perspective, I head over to the SaaStr blog or visit his Twitter feed. He’s my go-to.”

What’s the one piece of technology you couldn’t live without, and why? “My iPad. There is no better mechanism for quelling discord or motivating good behavior among my two young boys.”

Phil Gordon desk
Is Chatbox the next tech unicorn? Phil Gordon believes in the power of positive visualization around his workspace. (Photo courtesy of Phil Gordon)

What’s your workspace like, and why does it work for you? “I love and need lots of screen real estate. Three monitors at a minimum, please. I also believe in the power of positive visualization, which is why you might see a few unicorns.”

Your best tip or trick for managing everyday work and life. (Help us out, we need it.) “Startup life can be ‘weedy’ so, each day, I try to spend at least a little time in the clouds. Learn how to manage yourself and remind yourself of the larger vision instead of weed-eating.”

Mac, Windows or Linux? “Mac.”

Kirk, Picard, or Janeway? “Kirk.”

Transporter, Time Machine or Cloak of Invisibility? “Transporter.”

If someone gave me $1 million to launch a startup, I would … “First, make sure I was the best person possible to run it — and, if not, help them find the right person.”

I once waited in line for … “BBQ. True Texas BBQ. Anywhere, anytime. Nothing compares.”

Your role models: “Bill and Melinda Gates. They’ve changed the lives of billions of people multiple times — first through software, then through philanthropy. Thomas Kurian (president, Oracle) also immediately comes to mind. He’s the heart and soul of the Oracle software engine — insightful, strong-willed, and a keen eye for the important things that drive innovation.”

Greatest game in history: “Bridge (I’m a two-time national champion) — and yes, people are always surprised that I answer bridge instead of poker.”

Best gadget ever: “The iPhone.”

First computer: “Timex Sinclair 1000, tape-drive not included.”

Current phone: “iPhone 8.”

Favorite app: “BridgeBase for fun, Twitter for punishment.”

Favorite cause: “Prevent Cancer Foundation.”

Most important technology of 2016: “Facebook Messenger ‘Bot’ platform, and Amazon’s Alexa. Finally, someone my kids can boss around.”

Most important technology of 2018: “Blockchain.”

Final words of advice for your fellow geeks: “Be patient and observant — identify a profitable opportunity. Then, be courageous and tremendously aggressive — get your chips in the pot. Be resilient when things inevitably go sideways. And always be looking for ways to improve.”

Website: Chatbox

Twitter: @PhilNoLimits

LinkedIn: Phil Gordon

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