Jack's February 2024 Recap: I Got a Job

Employment update, + book and content recs

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Welcome back to my monthly update! As a reminder, at the end of each month, I’ll send a few brief updates about what I’ve been working on/thinking about, as well as links to any interesting books/content I’ve read, watched, or listened to over the last month. Let’s get started.

General Update

February flew by, didn’t it? I swear New Year’s Eve was just a week ago, and here we are in March. They say that our perception of time accelerates as we age. It certainly feels that way.

Anyway, on to the updates.

A few weeks ago, I accepted a full-time job offer to join Sherwood Media (announced here in Semafor) as an editor and columnist. I start on Monday, and I couldn’t be more excited. Some details about the work and how I reached this point.

Sherwood is a new media venture being launched by fintech company and investing platform Robinhood. A few years ago, Robinhood acquired a finance/markets newsletter, MarketSnacks, and Snacks has since become one of the largest newsletters on the web. Last year, Robinhood hired Josh Topolsky (my new boss), to build an independent media company on top of their newsletter’s existing audience, launching new verticals and editorial products. I’m joining to help with this expansion.

So why this job? A few reasons:

First, I love writing about finance and markets, and I occasionally cover financial topics on Young Money, but at the end of the day, my blog is really a collection of my thoughts on a variety of topics. Sherwood is a financial media company, so I will be able to double down on writing detailed financial content and publishing my thoughts on the biggest stories in finance and business. I’ve wanted an outlet to really nerd out on all things finance for a while, and I’m happy to finally have one.

Second, the resources and access that come with working for a media company (as opposed to writing a blog) are night and day. I love writing. I’ve always loved writing. But I haven’t loved all of the admin tasks that come with writing as a freelancer, from ad sales to troubleshooting tech to invoicing sponsors, and independent writers are resource-constrained on both the operational and research fronts. Working for Sherwood allows me to do what I do best: write.

Third, this is an incredible opportunity to learn. For the last two years, I’ve built my blog to 50,000 readers and helped grow Exec Sum to 270,000 readers, but both of these have been relatively small-scale operations. I’m pumped to work with a team of really, really talented editors and writers in a larger organization. I have so much to learn about journalism and media, and now I’ll be right in the middle of it. Early in your career, it’s crazy not to surround yourself with ambitious people, and I’m pumped to have an opportunity to do just that with a company and industry that I’m excited about.

Fourth, I want as many people as possible to read my writing. Sherwood’s audience is exponentially larger than mine, and they can devote far more resources to growth than I ever could independently. Every writer, myself included, wants millions of people to read their work.

Fifth, the peace of mind that comes with a job is criminally underrated. Living invoice to invoice as a freelancer, especially in New York City, is a chaotic lifestyle. The stress of making a living that way created a lot of mental overhead that distracted me from my writing itself. I want to write, and I want to write well. It will be much, much easier for me to focus on the quality of my content over everything now.

My thoughts on career paths have changed a lot since I started writing this blog in 2021. 2.5 years ago, I thought of “work” as a prison to be escaped. It was a zero-sum game where you had to sacrifice ____ hours for $X income. In some circumstances, I do still think that’s true, but just because some jobs are zero-sum doesn’t mean all jobs are. Maybe this is a sign of maturity, or maybe it’s the difference between being 24 and almost-27. If you find an enjoyable opportunity that lets you hone your skills, a job can be positive sum. I was fortunate to find one such opportunity.

Once we go live with Sherwood, I’ll make sure to share my content with you all, and don’t worry, I’ll still be blogging regularly. For the first time in a long time, I can write my blog for fun instead of finances.

On to the book and content recs.

Books I Liked

1) Liar’s Poker by Michael Lewis

I know, I know. “How are you just now reading Liar’s Poker?” I have no idea, but I understand why this book is GOATed. Michael Lewis is as hysterical as he is intelligent, and his portrayal of the bond-trading world of the 1980s is outrageous. Liar’s Poker is a page-turner that I couldn’t put down. Check it out on Amazon.

2) Wanting by Luke Burgis

Before reading Luke’s book, I had never heard of “mimetic desire.” After reading Wanting, I see it everywhere. Building off research from the late French polymath René Girard, Burgis’s book explains the foundations of desire, and how so much of what we want is simply influenced by the wants of those around us. Check it out on Amazon.

3) Do Travel Writers Go to Hell? by Thomas Kohnstamm

Okay, this is a niche recommendation that some of you will love and others will hate, but I thought this book was hysterical. Do Travel Writers Go to Hell is Thomas Kohnstamm’s journey from working on Wall Street to a travel bug-induced “job” working for Lonely Planet in Brazil. Maybe I only relate because of my travels a few years ago, but I thought this book was fantastic. It had everything you could wish for in a travel book: absurd acquaintances, questionable sexcapades, financial troubles, and more. Check it out on Amazon.

Other Content

  • A few weeks ago, I found this old Tim Ferriss podcast with Michael Lewis (this podcast is actually what led me to reading Liar’s Poker). This episode was filled with excellent insights into Michael’s time selling bonds for Salomon Brothers, as well as his earliest writing experiences.

  • The Atlantic’s Derek Thompson published a thought-provoking piece on the decline of “hanging out” in the United States. More screen time + less in-person hang time hasn’t been good for the kids, it seems.

  • I loved this piece on “Creator Search Funds” by Anu Atluru. We’re seeing more and more A-list creators partner with operators (James Clear partnering with Andrew Wilkinson to build his Habits app, Marques Brownlee joining Ridge as Chief Creative Partner), as both sides realize these partnerships can be 1+1=3 positive sum games. I expect this trend to continue.


  • One of the toughest things about being a freelancer (or anyone with their own LLC, really) is separating your business finances from your personal finances. Last year, I set up a Mercury account for my business finances, and I couldn’t be happier. Mercury has a sleek, user-friendly interface, and you can easily track and move your money from account to account. If you need to set up a business account, check out Mercury here.*

  • Writing online has been, without a doubt, my most valuable pursuit over the last two years, and 1 question that I often receive from aspiring writers is, “How do I get started?” My friend David Perell runs a writing school called Write of Passage that teaches people to create a range of opportunities for themselves by sharing ideas on the internet. Many of his alumni have landed book deals, job offers, and more after graduating from his program. David's writing school is hosting a free workshop that allows you to experience their writing Bootcamp. If you’re interested, you can sign up for the workshop using my affiliate link.

*Occasionally, I will include various affiliate links in my newsletter. I only link products and services that either I have personally used or several of my friends have personally recommended. Affiliate deals help keep this blog free for everyone.

As always, thanks for reading! If you want to send any interesting content or book links my way, please drop the link(s) here.

- Jack

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