Penguin Random House

Working on my first book with Penguin's imprint, Portfolio. Stay tuned!

Author

Sherwood Media

I cover business and markets stories for Sherwood News, Robinhood's new media subsidiary. I write a biweekly opinion column, "Weird Money," as well as occasional feature stories.

Columnist

Young Money Newsletter

Since August 2021, I've been sharing my thoughts on money, work, the complexities of life, and more introspective musings in my weekly newsletter, Young Money. As of September 2024, I have ~64,000 email subscribers, and my articles attract millions of page views each year. Check out my newsletter in the link below.

I also occasionally speak on the above-mentioned topics for conferences, companies, and other audiences. Message me here or email me at jack@youngmoney.co for inquiries.

Writer

Litquidity Media

I was the Editor-in-Chief of Exec Sum, a daily financial newsletter created by the popular finance meme page, Litquidity.

In my time with Exec Sum, we grew our subscriber base from ~90,000 subscribers to ~270,000, I was responsible for editing each day's newsletter, communicating with advertising partners, and creating long-form sponsored content.

Day-to-day operations included:

Curating all relevant deals across M&A, VC, PE, SPACs, etc.
Identifying the most relevant headline news stories from the previous day's news cycle
Providing recaps of the most important earnings reports from the previous day
Assisting with ad copy and maintaining communication with sponsors

Editor in Chief, Exec Sum

Backpacking Travel Blog

Before moving to New York City for business school, I spent the better part of a year traveling around Europe, with a two-month stint in Argentina, and writing. A lot. I wanted to see the world while I was still young enough to pursue my wanderlust, and I decided to document the whole journey. Both of which were, in hindsight, wise decisions.

I visited more than 20 countries in total, recording the journey across 50+ blog posts. Highlights include seeing the northern lights in Tromsø, Norway, driving a Fiat 500 around the Amalfi Coast, visiting my ancestral roots in Edinburgh, fighting for my life to improve my Spanish in Buenos Aires, and, of course, making a dozen lifelong friends along the way.

If you're young, go see the world for a bit. Future you will be glad you did.

Travel Blogger

My first job out of college, which, unfortunately, coincided with the start of the Covid-19 pandemic. However, I quickly learned how different macroeconomic shifts (like pandemics and negative oil prices!) impact the logistics of distribution networks, as my team adjusted UPS's North America profit plans in the wake of the pandemic.

As with most entry-level finance jobs, I also quickly learned to master Excel and PowerPoint.

Domestic Finance Specialist

U.S. House of Representatives

Legislative Intern

Writer, among other things.

Blog: I've been writing my blog, Young Money, weekly since August 2021, and as of September 2024, I have ~64,000 subscribers. Topics range from behavioral finance to existential introspection.

Book: I'm working on my first book with Penguin Random House's imprint Portfolio.

Day job: columnist for Sherwood Media, Robinhood's media subsidiary. I cover business, markets, and more, and I write a twice-weekly column, "Weird Money."

Jack Raines

X, the everything app, now shows "country of origin" of everyone's accounts. Turns out that 90% of anonymous MAGA influencers live in India, Bangledesh, and various sub-Saharan African nations.

The LinkedIn version of this would be exposing everyone who puts "Harvard Business School" in their education after taking an online course, or showing that the "fractional growth leader" with 200k+ followers runs an agency making $3,421 a month running Meta ads.

Forward Deployed Personality Hire @ Slow Ventures

The "open to work" banner on LinkedIn is like the Hinge rose of looking for a new job. It reeks of desperation. The only people who will take you seriously are those who are equally desperate.

I instead propose that you should cold DM your ideal employers and say, "I'm not interested in working for you." It sparks intrigue. Mystery. They'll think, "Hmmm, why would Jack go out of his way to 'not want to work for me'? What does he know? What is he hiding?"

Next thing you know: $500k base + equity.

Work smarter, not harder. Don't be an NPC.

There's a viral Substack post claiming that $140k is the new "poverty line" in 2025.

I can't believe we're really arguing whether or not $140k represents a new poverty line. Of course it does. Take the typical after-tax monthly budget: housing $2k, food $1.5k, and token usage on Cursor / Claude Code $6k.

How are you supposed to invest for the long-term?

graphical user interface, text, application, chat or text message

Today I’m thankful for VCs creating the term “operator” to describe what everyone else calls “a normal job.”

Angèle Sahraoui on our team at Slow Ventures put together a 10/10 deck on the history of the maritime infrastructure and which new threats and opportunities are emerging thanks to recent tech shifts.

If you're into deep tech, or you're an avid ocean enjoyer who's curious about what's going on under the sea, check it out. Also, if your startup is trying to find Atlantis, shoot her a DM.

Full deck: https://lnkd.in/e2sbt6Yw

After a 3 month break I’m firing my newsletter back up post-book writing. Highlights include self-gaslighting and thoughts on Robinhood x prediction markets.

https://lnkd.in/eXrK_8Ae

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Thanks to popular demand, we decided to take Slow Ventures’ “Etiquette School” a step further and write an etiquette book.

If you missed out on the IRL lessons and need help with your eye contact, snag a copy here and come to one of our live events in 2026.

Link: https://a.co/d/9K8tZzE

Unfortunately I couldn’t afford a real fireplace this year, so I had to build one in the metaverse instead.

#HappyHolidays #Web3Fire #Chimney

Horizontal AI this, vertical AI that. Is anyone building Diagonal B2B AI SaaS?

Ryan Sager

The Newsletter Conference

Bringing together the newsletter industry.

Co-Founder

Who Sponsors Stuff

Founding Partner

The Expedition

Montague Street Media

Provide digital media and editorial consulting services to private clients looking to grow audiences, improve newsroom performance, and/or stand up scalable new editorial operations. Consultation includes development of editorial products, growth strategy, analytics, hiring, implementation, and on a case-by-case basis continuing oversight.

Founder

Ladders

Directed editorial & digital product for news site covering the future of work — encompassing all aspects of product, from newsletters to site development to ad sales and revenue generation.

- Grew traffic from 0 to 6 million monthly unique visitors using a variety of owned and distributed channels, including newsletters, Flipboard, SmartNews, and Apple News

- Started daily editorial newsletter reaching 2.5 million people a day, selling 7-days-a-week to direct advertising clients and generating millions a year in revenue

- Created specialized newsletter products that drove additional hundreds of thousands of dollars in ad sales per year

- Implemented registration wall on Ladders editorial, driving lead generation and upgrades onsite

VP of Content

Conceptualized, launched, managed site with 15 employees across editorial, design, social media, and sales covering all aspects of the future of work & the office.

Editorial Director

Time Magazine

Expanded TIME’s Ideas vertical into a thought-leading powerhouse across digital and print:

- Grew traffic by 18x, to 9 million unique visitors per month, driven by Facebook, Twitter, and greatly increased pick-up of news-making essays and op-eds

- Introduced major new features and columnists, including pieces by Camille Paglia, Martha Stewart, and Kareem Abdul-Jabbar

- Produced 7 cover packages, including the Ideas Issue featuring Key & Peele, as well as Tyler Cowen’s essay on ‘Why Texas Is Our Future’ and TIME’s reported feature ‘Help! My Parents Are Millennials!’

Editorial Director, TIME Ideas

The Wall Street Journal

Founded WSJ Weekend’s influential Review section:

- Prototyped and launched Review, WSJ's influential books & ideas weekend section

- Generated cover essays, including the buzzy ‘Tiger Mom’ and ‘French Mom’ essays, that became 2011's & 2012's most-read WSJ.com stories

- Created and ran the national Ideas Market event series, featuring A-list speakers including Henry Kissinger, P.J. O’Rourke, and Amy Chua, with sponsorship from major national brands, including Dell, United Airlines, and Amazon

Founding Editor, Review

The New York Sun

Started politics-focused Web site for the Sun, managed contributing writers and deputy online editor. Coordinated Web design team.

Web Editor, political columnist, and blogger

New York Post

Reported, wrote op-eds and editorials on local and national political issues.

Editorial Board Member / Columnist

Ran editorial page. Wrote editorials, commissioned op-eds, and managed columnists and staff.

Editorial Page Editor

Building: WhoSponsorsStuff.com... We help media brands grow revenue.

Hi, I'm Ryan. I've launched and grown major print, web, and email products for The Wall Street Journal, TIME, and other brands. I'm also the co-founder of Who Sponsors Stuff, which helps newsletter publishers power their ad sales, as well as The Newsletter Conference, May 2, 2025 in New York City.

Newsletter enthusiasts! This week's Email Intelligence newsletter is out...

Stories by or about: Emily Sundberg and Feed Me, Substack, Puck, Nieman Journalism Lab, beehiiv, Digiday, Sara Guaglione, Jacob Cohen Donnelly, A Media Operator, Matt Brown, DNNR // River.

Advice by: Dylan Redekop, Chenell Basilio, The Media Stack.

Jobs from: Patch.com, Condé Nast.

Sponsorships in: 6AM City, The Business of Fashion, Visual Capitalist, and more!

💌

Building: Who Sponsors Stuff & The Newsletter Conference... We help media brands grow revenue.

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The Battle

Jack Raines

Ryan Sager

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The Battle

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Ryan Sager

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jack Raines's LinkedIn Performance

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