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?

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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?

Robin

Taking Robin from pre-revenue to lots of revenue.

Robin is an SMS-based communication tool built for event organizers who need to reach people fast.

Designed to solve common headaches like last-minute changes, unanswered emails, and fragmented comms, Robin gives organizers a simple way to keep attendees in the loop through automated text messaging. Think schedules, reminders, safety updates, menus, and more - delivered straight to phones.

Robin is already working with events across Canada, including Nuit Blanche and the North Forge Founders Program. Organizers can set up in minutes, personalize their messaging style, and monitor responses in real time. It’s fast, friendly, and helps teams do more with less.

Go-to-Market

Afters

Founder

Various Companies

Companies I've helped go from initial product/service to market exposure & new clients since October 2024:

MyAreaa
A community banking & socializing platform. Targeting niche communities to raise product awareness to increase user adoption. Also supporting by arranging events for community leaders to organically raise awareness.

Kokoro Energy
A wellsite geology & technical advisory shop. Initial clients were gained by the founder, I've now built and executed on a growth strategy to gain more clients and diversify revenue streams. Activities included building a geologist community, attending industry events, and doing extensive cold outreach.

BITCAP
A geosteering software solution built by a brilliant geologist duo. They're building out their MVP and I'm helping them reach their ideal target market. I do this by namedropping them at industry events, and building relationships with their ideal customers and asking them to test the software before distribution efforts are made.

Afters
This is my personal project. Afters is a company that specializes in throwing afterparties for corporate affairs. Our first event was for a Tech Thursday biotech panel. Next one coming up is an Inventures afterparty. 

Stealth - Dental Technology
Currently developing a MVP. I found a firmware engineer to develop the initial product for the founder, and will be deeply involved with market validation and finding initial clients once it's developed.

Maria J Yoga 
A yoga company that goes into corporate offices during lunch hour to do specialized desk work yoga. I helped the founder take it from an idea to finding her her first client. I'm now helping her find more clients and also helping her understand how to go from working "in" the business, to working "on" the business.

Consultant

Kokoro Energy

My role is make sure people know Kokoro Energy exists, and establish how it differentiates itself. Some of the things I've done:

• Identified creative ways to reach Kokoro's ideal clients without spending money (community building, content creation, social selling)
• Created a value-driven geologist community (GeoSocial) to establish brand presence to a targeted market.
• Launched a technical advisory vertical to meet market demand and utilize existing skills within the org.
• Enter the industry with none to little brand presence, and slowly established Kokoro's position as a high-end, boutique service provider for complex wells.

Growth

Grid Group

Fortunate enough to have worked with an incredible team to headhunt talent for top firms.

Headhunter

Morgan Stanley

Learnt about, and administered, equity compensation plans for companies.

Client Success Manager

Analyst for the Client Engagement team, focused on building strong relationships with brokers and clients while driving business growth and retention.

Analyst

Apple

People don't like when their iPhones break. My job was to make sure they left our store satisfied.

Technical Specialist

CIBC

Worked as a bank teller in a diverse community. Had to work on my Punjabi so I could communicate with our clients.

Customer Service Representative

I throw afterparties. I support the ecosystem through thoughtful introductions, targeted relationship building & niche community development. 

In my spare time I play squash, read dystopian science fiction, backpack, and help my friends launch businesses.

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Jack Raines

Shaharyar Ahmad

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The Battle

Jack Raines

Shaharyar Ahmad

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Engagements

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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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