Tag: books

  • We Are Who We Choose To Be

    I recently read my book again, which has become an annual tradition. I do it as a barometer to see how far I’ve come—and how far I still have to go.

    What struck me most this year (outside of all the edits I’d make today) is how different a person I am now than the person I was when I wrote it just three years ago.

    For those who haven’t read the book, back in 2015 I was in a bad spot professionally and financially. So I hatched a plan and proceeded to manifest it. I joined an early-stage startup, effectively reinvented myself, and went on a run for the ages. At the end of it all, I had completely changed the trajectory of my career and reversed our financial fortunes.

    But the journey ended abruptly, and I was unceremoniously spit out the other side. It was an emotional gut punch that took me a while to process. I wrote the book during that period, which is why it feels like an emotional snapshot in time.

    The lessons I learned during those eight wonderful and terrible years absolutely hold up, but I am not the same person I was back then. That guy had tunnel vision born out of necessity, which led to an unbalanced life. The mountain I was climbing became my obsession, so I missed out on many wonderful things during the ascent.

    When I eventually reached the top, the air was thin, and there was no satisfaction or delight. I only felt emptiness for all the things I’d sacrificed along the way.

    I took a full year off from work under the guise of “early retirement.” After too much golf and a hip replacement surgery, I decided to get back in the game—but with a very different approach.

    I now make a conscious effort to enjoy the present, rather than always looking forward to the next thing. The good stuff in life is happening all around us every day. Choosing to enjoy it is simply a matter of perspective.

    This notion was reinforced with the birth of my first grandchild fourteen months ago (and I have another on the way!). Simple things can become core memories if you lean into the moment and embrace them fully.

    I suppose the lesson here is that we can change who we are at any point in time. It’s simply a matter of making the choice and controlling the internal dialogue in your head.

    Simply put: we are who we choose to be.

    Five months ago, I decided it was time to climb another mountain—this one even steeper than the last. I joined a pre-seed startup as the founding head of sales. Some think I’m crazy for taking this on at this point in my career. Early-stage building is brutal, and it can be a dark, lonely place without strong internal motivation. Plus, I already solved my financial crisis, so I should be professionally satisfied.

    Unfortunately, that couldn’t be further from the truth. I feel a strong desire to validate my past success with future success. I’ve also learned along the way that the best things in life are waiting on the other side of hard. So, I’m leaning in again.

    But this journey will be far different from the last.

    I will still apply a life-force effort to the success of the mission, but not at the expense of balance and harmony at home. Instead of always obsessing about reaching the peak, I’m going to find joy in the journey and embrace all the little victories along the way.

    I know now that I’m not nearly as important as I think I am. So instead of just playing the game, I’m choosing happiness—and I’ll let the chips fall where they may.

  • I’m Not Throwin’ Away My Shot

    I recently had a conversation with a former colleague. He was intrigued by my decision to join a seed stage start-up as the founding head of sales. Dude, do you know how much work that’s going to be?  Why not join a bigger, less risky company and coast it out? At this point in your career, don’t you think you’ve earned it? That would be the easy choice. I’m 52 years old and on the back nine of my career. Most people in my situation would indeed choose the comfortable path. I’m not most people. 

    The truth is I’ve been stuck in a rut professionally for the last few years now. I’ve done good work, but I haven’t felt satisfied. After a bit of soul searching it struck me. For the entirety of my career, I’ve been on someone else’s mission. I’ve mostly had a good seat on the bus and at times agency, but I’ve always had to play by someone else’s rules. That chapter of my career is now over. I’m no longer going to follow in someone else’s tracks. I’m going to make my own. It’s time to set out on my own mission where I control the outcome. 

    I’ve always believed if you’re not getting better, you’re getting worse. For the last few years I haven’t been getting any better. This role will force me to be better every single day. It is an exciting and somewhat daunting challenge to be the first one carrying the bag for a company with this kind of technical pedigree, but I’m all in. One of the lessons from my book is that true belief takes failure out of the equation. At Weilliptic, I truly believe we will forever change the world of AI. 

    If you’re wondering about the picture I chose for this post it is a rendering of Icarus from Greek mythology. His father, Daedalus, famously crafted two pairs of wings out of branches, string, and wax, so that they could escape imprisonment by King Minos in a tower on the island of Crete. Despite being warned by his father, Icarus flies too close to the sun, his wings melt, and he falls to his death in the ocean. Icarus is also the name of our fully aggregated AI chatbot, which is no coincidence. Our mission at Weilliptic is to enable our customers to take the capabilities of AI as close to the sun as possible, but without crashing and burning. We provide the missing trust layer so our customers can deploy AI safely, transparently, and cryptographically securely. 

    The mission is set. The tank is full. Now it’s all about the grind. LFG! 

  • Everyone Has A Story

    As I’ve gotten older I no longer have patience for small talk. It just feels like a waste of time. I want to know the real deep-down shit about people. What makes them tick? When were they most happy in their lives? What’s been their biggest disappointment or failure? How did they bounce back? Where do they want to be in ten years? Any bucket list items they’re eager to check off? If they could live anywhere in the world, where would it be? 1:1 dialogue is where it’s at. That’s where you learn the stuff about people that makes you feel something. It’s the same reason I love to read biographies. I want to know the essence of someone, not the superficial, surface-level bullshit (you the human > you the public persona). Over the past year I’ve read the following memoirs:

    The Light We Carry by Michelle Obama

    Friends, Lovers, and the Big Terrible Thing by Matthew Perry

    The Storyteller by Dave Grohl

    Oath and Honor by Liz Cheney

    Greenlights by Matthew McConaughey

    The Truths We Hold by Kamala Harris

    Be Useful by Arnold Schwarzenegger

    A Life in Parts by Bryan Cranston

    What I Know For Sure by Oprah Winfrey

    From Here to the Great Unknown by Lisa Marie Presley

    Born A Crime by Trevor Noah

    Kitchen Confidential by Anthony Bourdain

    A Very Punchable Face by Colin Jost

    It’s a Long Story by Willie Nelson

    Being Henry by Henry Winkler

    Yes Please by Amy Poehler

    I enjoyed them all for different reasons, and I intentionally chose a diverse range of people to learn about. Each of these authors is highly introspective and ultimately found success in their chosen field. But before they did, they all dealt with various setbacks and differing degrees of self doubt. Some were unable to overcome their demons (Matthew Perry, Lisa Marie Presley, Anthony Bourdain). Others became stronger as a result of their adversity. Each have led fascinating lives and all have left a lasting mark on the world in some way. Perhaps most importantly what they share in common is that they are all indelibly human. That’s why I want to learn someone’s real story, and have no time for the highlight reels they post on social media. The more I learn about other people the more I learn about myself, and the more I’m ultimately convinced that we’re all pretty much the same, except for Oprah – she’s the chosen one! 🙂 Bottom line how about we all cut the bullshit and start being real…