Thirty Three

Unlike Drake when he was ten years younger, I’m wondering if I’m really too old to be feeling this young. I’ve never felt more confident about, and excited for, the future work I’ll be doing.

I spent my birthday back in the office, planning with my team as we spin up a new organization at Audible dedicated to building products that support creators. Our team went out to happy hour after, and it was great to run into colleagues I hadn’t seen in person in years, or ever. I never plan to go back to the office full time, but there is something to the serendipitous interactions that you miss out on from home.

After getting home from happy hour and eating a fabulous dinner cooked by my fiancĂ©e, I continued prepping for the last few classes of the semester at Baruch and edited some onboarding documents for an angel investing syndicate I’m getting started.

My goal for the next year of my life is to continue surrounding myself with new opportunities and energetic, talented people. Building new organizations at Audible, teaching undergraduates in the final semester before graduation, and helping new companies get off the ground are a few of the ways I’ll be doing this.

The phrase “old and jaded” is making less and less sense to me, as every year I get older I only get more excited and optimistic about the future. We have some incredibly difficult challenges facing the world that we can’t ignore, but just as constraints breed creativity, the challenges we’re facing will bring out the best in us. I’m thirty three, and feeling younger than I ever have.

Global Media & Entertainment at Amazon

For a lecture in the Business Strategy undergraduate capstone course at Baruch in July 2021, I wrote the below 1 page case study. In the Amazon fashion, I had all of the students read the case during our class, we walked through it answering questions from the students, and then we continued to the discussion questions. I was very impressed with the students, and sharing in case it helps create more great discussions.

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My Personal Productivity System – Getting Sh*t Done in 2021

I was stuck inside for a rainy Memorial Day Weekend in NJ, thinking a lot about how I could make the most of my time. This inevitably comes down to the tools and systems I use to prioritize my work and get shit done. I wanted to document how I’m working right now, as it is always a work in progress. The best productivity system is simply what works for you – none of this should be proscriptive, but this is what works for me right now.

I’ve spent a lot of time thinking about how to manage myself and my work, since reading Merlin Mann’s 43 Folders and thinking too much about GTD in undergrad. I’ve used everything from a Hipster PDA to Omnifocus to text files. Still, updating my tools and systems is typically on my “not a priority” list these days. Despite the popularity of thoughtbois, working on your personal productivity system has extreme diminishing returns.

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Newsletters – May, 2021

About a year ago, I shared the newsletters I subscribe to. I still think newsletters, in addition to a properly curated Twitter feed, are the best way to both stay up to date on relevant news. They are also a great mechanism to support a continuous growth mindset.

There have never been more high quality newsletters as there are right now. Still, as part of how I put Inbox Zero into practice, I avoid subscribing to any newsletter I won’t be reading thoroughly. I am quick to unsubscribe if I find a newsletter is not providing the right ROI for the time invested to read it. With that bar, the newsletters I’m currently reading are all highly recommended if they line up with your interests or career.

New to the list are Not Boring and Lenny’s Newsletter (the latter I was trying out in June 2020). Anything I should be reading not on the list? Let me know.

Optimistic Notes Heading Into 2021

Generally, I am not optimistic about the short term future of the US or the world. I’m not writing songs about it, but there are large problems I don’t see a clear path to resolving. Still, as we head into 2021, there are a few areas where I am cautiously optimistic.


Unlike most FinTech companies that are creating a better UX for the same services of old, companies like Stripe, Affirm, and Pipe are building creative, new solutions. These companies will enable new opportunities for entrepreneurs and consumers. When everything is online, everything is data. Internet-native financial engineers are just getting started making use of this data, and I’m excited for what it could mean. Pipe looks like it could be capital-as-a-service at scale, helping companies grow and founders maintain equity, and Affirm is making it easier for both sides of large transactions. Stripe truly seems to just be getting started building the financial rails of the internet. As similar product offerings mature to become more accessible, I’m optimistic the global impact, especially from supporting or enabling small businesses, will be significant. Stripe’s continued global focus alone is responsible for much of this optimism.

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