{One of my all-time favorite board games is the super duper nerdy co-op
game by Wizards of the Coast called Betrayal at House on the Hill. Think
of it as a Choose Your Own Adventure RPG in a haunted house}
A little over a year ago, I started a board game club with some friends and coworkers. It was something we looked forward to once a week, to play a couple of classics while catching up. Through this I made a new friend, Jeff, who after a few weeks revealed to me that he used to be a pro poker player. In fact, he even made it to the Final Table in a World Series Event, walking away with a couple hundred thousand G's. Learning this, I felt pretty good about myself considering I had bested him several times in Settlers of Catan, but my jaw hit the floor when he explained that his World Series winnings were tiny.
All the pros, Jeff explained, use the WSOP as essentially a PR move to advertise their respective brands, events, and apparel {courtesy of ESPN's Live coverage}. The real money, Jeff told me, was in the private events, in which small circles of pros would compete for million-dollar pots regularly. In just a few hours you could be more than set for life - or lose everything you've got.
During one of those high-stake nights, Jeff's then-mentor, a decorated pro, received a tap on the shoulder from another legend. "Did I loan you three million or four million?" the one asked the other. "Gee, I don't know. I forget," his mentor replied. Jeff watched the two of them silently, and then the first answered, "I think it was three...yeah it was three...if it was four I would have written it down."
Hearing my friend recount this story of insanely high IOU's - about sleepless nights worrying if he'd ever make back the hundred thousand he'd lost hours earlier - about his painful, gradual struggle to become risk tolerant - I knew that these stories were important. It wasn't the amount of money these guys had, but their attitude. It wasn't a fearlessness, at least, not primarily. It was the idea that they were capable of winning in the long run - that a moment's defeat was temporary. They were all in - committed to the lifestyle, because they viewed success as attainable - and perhaps even inevitable - if they played out enough hands.
Jeff has since left the pro poker player lifestyle, working for a tech startup in Southern California, but I saw the same attitude in how he approached that work as he talked about his poker career.
I'm nowhere near as successful as Jeff, but talking with him and seeing his approach to risk has definitely left an impression on me. In part, it helped quell my anxieties about turning down a generous job offer in Austin - about firing my then-boss because I didn't love the work that filled my days - about starting my own freelance marketing business. It was terrifying for me to do those things. At least temporarily. I had plenty of my own sleepless nights at first, but slowly and surely I acclimated mentally to the changes. The first steps were the scariest. It only got easier. Because I had committed. I couldn't un-fire my boss from my life or un-reject the Austin offer. I had to make freelancing work.
I spent many a day and night huddled in a nook at the back of some odd Starbucks or Panera and dove head in to finding clients. It was a rush - because I was all in. Either get some work and get paid - or don't. Either get up earlier than I wanted to every morning - or stay up later to hit my quotas. Say no to a lot of fun opportunities - and say yes to nearly every copywriting offer than I could possibly handle. And pretty soon, I had a pretty good voice that was turning some heads, including the San Francisco-based e-commerce giant, Huckberry.
I had had my eye on Huck for almost two years, because of their stellar journal and its dedication to story, conversation, and quality products. So I wasn't surprised by the excellent discussions I had with their CEO and Managing Editor regarding brand identity, user experience, and the art of storytelling. When the offer to join the team came, there I was at another All In moment: to pick up and move once again, 3000 miles back to the West Coast - to a new city I'd never stepped foot in - to a house with roommates I'd never met {they're awesome} - to a company I didn't know, but admired from afar.
All the pros, Jeff explained, use the WSOP as essentially a PR move to advertise their respective brands, events, and apparel {courtesy of ESPN's Live coverage}. The real money, Jeff told me, was in the private events, in which small circles of pros would compete for million-dollar pots regularly. In just a few hours you could be more than set for life - or lose everything you've got.
During one of those high-stake nights, Jeff's then-mentor, a decorated pro, received a tap on the shoulder from another legend. "Did I loan you three million or four million?" the one asked the other. "Gee, I don't know. I forget," his mentor replied. Jeff watched the two of them silently, and then the first answered, "I think it was three...yeah it was three...if it was four I would have written it down."
Hearing my friend recount this story of insanely high IOU's - about sleepless nights worrying if he'd ever make back the hundred thousand he'd lost hours earlier - about his painful, gradual struggle to become risk tolerant - I knew that these stories were important. It wasn't the amount of money these guys had, but their attitude. It wasn't a fearlessness, at least, not primarily. It was the idea that they were capable of winning in the long run - that a moment's defeat was temporary. They were all in - committed to the lifestyle, because they viewed success as attainable - and perhaps even inevitable - if they played out enough hands.
Jeff has since left the pro poker player lifestyle, working for a tech startup in Southern California, but I saw the same attitude in how he approached that work as he talked about his poker career.
I'm nowhere near as successful as Jeff, but talking with him and seeing his approach to risk has definitely left an impression on me. In part, it helped quell my anxieties about turning down a generous job offer in Austin - about firing my then-boss because I didn't love the work that filled my days - about starting my own freelance marketing business. It was terrifying for me to do those things. At least temporarily. I had plenty of my own sleepless nights at first, but slowly and surely I acclimated mentally to the changes. The first steps were the scariest. It only got easier. Because I had committed. I couldn't un-fire my boss from my life or un-reject the Austin offer. I had to make freelancing work.
I spent many a day and night huddled in a nook at the back of some odd Starbucks or Panera and dove head in to finding clients. It was a rush - because I was all in. Either get some work and get paid - or don't. Either get up earlier than I wanted to every morning - or stay up later to hit my quotas. Say no to a lot of fun opportunities - and say yes to nearly every copywriting offer than I could possibly handle. And pretty soon, I had a pretty good voice that was turning some heads, including the San Francisco-based e-commerce giant, Huckberry.
I had had my eye on Huck for almost two years, because of their stellar journal and its dedication to story, conversation, and quality products. So I wasn't surprised by the excellent discussions I had with their CEO and Managing Editor regarding brand identity, user experience, and the art of storytelling. When the offer to join the team came, there I was at another All In moment: to pick up and move once again, 3000 miles back to the West Coast - to a new city I'd never stepped foot in - to a house with roommates I'd never met {they're awesome} - to a company I didn't know, but admired from afar.
{Leather Satchel I had purchased from Huckberry last summer. Works perfect for
afternoons of writing and treks through Horsetooth Reservoir in Fort Collins, CO}
I had just moved across country six months prior. The nature of freelance work is that you can do it anywhere, so I moved back to my hometown to be closer to my family. My younger brother had just gotten out of the marines and I hadn't seen much of him in five years. My littlest brother was making his exit from High School to the college world.
{View from my morning walks in West Chester, PA. Thankfully
Bam Margera and the rest of the Jackass crew weren't around.}
But there was this new opportunity in front of me now - an ability to tell stories, to work with a young and hungry team, to learn a lot about business. So I said "yes" and packed my bags for SF. I was All In all over again.
I'm not writing this to pat myself on the back - I'm writing it because of something that a friend told me when I told him that I was going to take the job. He said, "That takes a lot of guts to do that." I thought about that for a while afterwards. Was he right? Am I just a gutsy guy who is comfortable taking big risks and making big changes? Or was it something else?
Was it that the alternative - of not taking the job - of not jumping on the chance to hone my craft of storytelling - of not going All In - was that actually the thing that takes a lot of guts? To sit on your hands and watch your time and energy and money and chances at more of those things fly by?
I think it is.
That's the real gamble - because it's a losing hand every time. { J }
I'm not writing this to pat myself on the back - I'm writing it because of something that a friend told me when I told him that I was going to take the job. He said, "That takes a lot of guts to do that." I thought about that for a while afterwards. Was he right? Am I just a gutsy guy who is comfortable taking big risks and making big changes? Or was it something else?
Was it that the alternative - of not taking the job - of not jumping on the chance to hone my craft of storytelling - of not going All In - was that actually the thing that takes a lot of guts? To sit on your hands and watch your time and energy and money and chances at more of those things fly by?
I think it is.
That's the real gamble - because it's a losing hand every time. { J }
{Some Huckberry swag gifted to me on my first day in
the office. I don't feel cool enough to wear it quite yet.}
