Archive for July, 2021

Syncing Curves

Posted on July 28, 2021. Filed under: Uncategorized |

Tonight when I was putting my two year old to bed, I realized that he’s now at an age from which I have actual memories. It was like he was touching the first plotted point on the curve of my conscious life…and with that realization came a very different type of empathy and envy for him. Empathy was for the depth of his current experience. A weekend is no longer just time to move through, but perhaps something so significant that it will be with him forever. And envy, for the volume of experience that is the product of that depth times the time that he will walk the earth. I think about the volume of my own life over the past (cough) 39 years, and suddenly I see this forward movie of his playing that is so rich and full of everything it is to be human, come of age, love, learn, feel, and so forth…He’s in for such an epic fucking ride…and as he moves through the years and stages that I have already experienced and loved, I will be experiencing something that is probably going to be great also, but without the kick of self-actualization. You only get to go through that once, and it’s ahead of him and behind me.

I look at his little butt, squirming in the sheets as he searches for a comfortable position to sleep, and I think about his physical growth as a form of timepiece, measuring his progression through this voluminous ocean. It doesn’t reflect but a fraction of the experience ahead, and yet it progresses at that same rate as all the more etherial and metaphysical elements of his existence.

I can’t help but fear for him in the decades ahead. Climate, intolerance, inequity, pandemic, and so forth…all constraints that will make his version of growing up different than mine. What if his entire existence is in the same state of stress that feels an aberration to us at this moment? But that fear is tempered by an equal or greater optimism. I see the problems he’s facing, but can’t yet see the solutions and inventions and revolutions that will make his life as rich and “good” as mine has been. My sense is that they will come. I had lunch last week with my friend Nick Chirls. I was in a particularly glum mood, contemplating the potential demise of humanity and the planet, and he looked at me deadpan and said “I think we are going to figure it out.” I think he’s right, and I think the solutions don’t come until a generation of people, like my sons, are born with these stressors baked into their earliest sentient experience. And while it’s painful to internalize the harm that truth presents to my kids, it’s reassuring to know that the ingenuity and ability of our species, when trained on a given context over a long period of time, can change that context. My hope is that my sons will participate in that endeavor.

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The Times They Are a Changing

Posted on July 26, 2021. Filed under: Uncategorized |

I took a walk around Washington Square Park last week with someone I’ve known for a long time in the startup ecosystem. We’re not super close, but I read his writing, and he mine…which I suppose is a different type of closeness. He mentioned on the walk that he’s noticed I am writing less frequently and asked why. The first, knee jerk answer I had was that I used to write more when I had nothing to lose. Whether I was fighting to establish myself as a VC in my 20s or fighting to get a company off the ground…in both scenarios I had little to lose…so I wrote pretty much everything that was on my mind. I look back at that writing, and some of it was excellent…to the point where I’m in disbelief that it actually came out of me. Some of it is also totally cringe, or embarrassing, or not representative of who I feel I am. Either way, it was unfiltered (as I think the best writing is). Today, I probably have more thoughts or feelings that I just let marinate…sometimes I’ll take the time to write them down, but often I ask myself “does the public need or want to read this?” I used to not care about that question…I’m still not sure I care if I really think about it, but it does come up and it does get in the way of publishing posts.

Overall, I don’t think that’s actually the main reason. The main reason is because I have less of a dialogue with myself than I used to. I am an introvert. I need and value quiet time and reflection. And most of my writing is just documenting the conversation I am having with myself in that quiet time. My life at the moment is more execution and less reflection. I now have a 2 year old named Odysseus, which zapped about 90% of my independent reflection time, and a month ago I had a second child named Atlas which zapped 9 of the last 10%. I think I write less now because I “talk” to myself less. I miss that dialogue but it’s an obvious trade to make so I can be present with my family.

I’ve managed to carve out quiet “deep work” time at Pace, where I’m able to advance my professional thinking in a more focussed and applied way, but the meandering walk around Washington Square Park, or the hours spent sitting on a bench and watching New York City go by…that stuff is gone (for now). I guess this is nothing novel…the story of every young New Yorker turned parent of two…I guess it just means I’ll have to get more creative about finding a 25th hour in my days…

P.S. Look at these little dudes. Totally worth it 😜

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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