India, Deep Work, and Some 2026 Goals

Brief weekly update between Christmas and New Years

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Winter Travel and Wedding in India

I hope everyone has been enjoying the holidays. This has been one of the more hectic travel periods of my life. From mid-December through next week, my travel schedule has looked like this: San Francisco to New York to Tampa to New York to New Delhi to New York to Atlanta to Tifton to Birmingham to New York to Geneva to New York. Safe to say I’m stacking up airline points during the holiday season.

A couple of weeks ago, I flew to India for a week for a friend’s wedding. It was, without a doubt, both the most fun, and most hectic wedding I’ve had the pleasure of attending, so I fired the travel blog back up to recap my week in South Asia. See below for a brief snippet from the blog, as well as the full post:

Tie comes off. Ben grabs me. “We need to go outside, now.” He seems serious. We head to the courtyard. A bunch of older Indian men are there.

“How much do you want to bet?”

“What?”

This 60-year-old Indian man stares at me, takes another hit of his cigarette, then repeats himself. “I arm wrestle your friend. Gamble on it. How much are you going to bet?”

Ah. Apparently, Ben had orchestrated an arm wrestling ring to take place the final night of the wedding.

I look in my wallet and see ~$120 and change.

I glance at this Indian dude. He definitely has old man strength, and, at 12:42 AM, there’s a healthy dose of nicotine and whiskey flowing through his veins. I glance at Ben. There’s more than a healthy dose of tequila flowing through his veins; we’ve been drinking non-stop for five days.

“$120, that’s all the cash I have.”

“$20?”

“No. One HUNDRED and twenty dollars.”

“How many rupees is that?”

“I don’t know, like 13,000?”

The Indian man grabs his wallet and yells “THIRTEEN THOUSAND RUPEES” and throws it on the table.“I guess I’m betting $120 on an arm wrestling match,” I think to myself. I throw my cash down too.

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What I’m Reading / Consuming:

• I didn’t read many books in 2025, largely due to much of my free time being subsumed by my own book. With that largely behind me, I plan on reading quite a bit more in 2026. As always, I’m open to any and all book recs that you find interesting / useful.

• Deep Work by Cal Newport. One of my biggest struggles over the last year (and I don’t think I’m alone in this struggle) is the ability to “lock in” and focus on mentally taxing tasks for extended periods of time. Working from the same device that houses iMessage, Instagram, Twitter, Reddit, etc. leaves your distractions just a click away from your work, meaning that the temptation to break concentration for “just a few minutes” is ever-present. I found Newport’s classic to be quite, quite helpful in 1) unpacking the value/importance of preserving “deep work” windows in your daily life (vs. spending the whole day triaging emails, jumping from low-leverage task to low-leverage task, etc.) and 2) structuring your life to preserve these deep work periods. Good read for any other white collar workers who feel that they spend their days just trying to stay on top of their days.

• Default: The Landmark Court Battle over Argentina’s $100 Billion Debt Restructuring. I did some research in the litigation finance space last fall, which send me down a rabbit hole of interesting Lit Finance cases. Elliott’s Management’s decade+ legal battle with Argentina over a series of bonds they bought in the midst of an Argentine debt restructuring remains one of the most fascinating stories in law/investing. I’m still working through this book as the writing is fairly dense, but the author paints an incredibly detailed picture of the multi-year legal battle between various claimants and the South American sovereign. For anyone interested in the space, it’s a quite interesting read.

• Greg Blotnick’s recent Twitter threads. Eventually, you come across a new Twitter follow churning out interesting post after interesting post. Greg is one of such posters. His story is pretty wild: a fellow CBS alum ~10 years older than me, he spent most of his career as a L/S hedge fund analyst/PM before launching his own fund. He went to prison for a couple of years in 2022 for PPP loan fraud (I believe he was investing funds raised from PPP loans), and he was released maybe a year ago? Anyway, he’s been churning out really interesting thoughts across both valuation frameworks / public equities investing and broader life philosophy. It looks like he wrote a book while in prison, too. Anyway, if you’re interested in markets, he’s a good follow.

• The Bitter Lesson: A six-year-old post from Canadian computer scientist Rich Sutton on the long-term trend of the only thing mattering for the sake of improving AI/ML research being the availability of more compute. Evergreen blog post given what we’re seeing with datacenter buildouts in 2025. “The bitter lesson is based on the historical observations that 1) AI researchers have often tried to build knowledge into their agents, 2) this always helps in the short term, and is personally satisfying to the researcher, but 3) in the long run it plateaus and even inhibits further progress, and 4) breakthrough progress eventually arrives by an opposing approach based on scaling computation by search and learning.”

• Bill Gurley on The Tim Ferriss Show. Bill Gurley is one of my favorite minds in the venture world, and I really enjoyed his discussion on the world of VC today, developments in China, and figuring out your career.

What I’m Interested In:

Building off my note on Cal Newport’s book, the number one priority for me in 2026 is being meticulous about creating and maintaining time for deep work during my day(s). There are exponential payouts to being able to hone in on a particular thing for hours at a time without interruption, and every time your attention deviates from the task at hand to check an email, scroll Instagram or Twitter, or text someone back, you blow up that focus. This has been a long-time struggle of mine, particularly when sites like Twitter are, at least loosely, “useful” for my job. But it’s a battle I want to address head-on and win this year.

Besides that, I have a couple of non-work-specific focuses to kick off the new year:

1. Going quite, quite deep on building more novel vibe-coded AI applications and refining my understanding of where these models are going at a technical level. Regardless of whether you’re an investor, entrepreneur, or employee, I think you’re doing yourself a massive disservice by not seeing what these tools are capable of, and, importantly, what they’re not capable of.

2. Tightening up my accounting / valuations / modeling frameworks / skills. I never went through the investment banking gauntlet common to a lot of investor/finance types from 22-24, and, while we largely invest in the earliest stages of companies, I think having a full toolkit as an investor where you can breakdown any business, from a $30 million startup to a $30 billion publicly-traded company, is just useful. I’m going to spend the next month or so working through McKinsey’s “Valuation” book, plus a few other resources for improving this area for me.

- Jack

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