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?

Jacob Kantor

Education Technology Leader - GTM/Sales - Helping Ed Tech Companies reach more students & connect with district leaders nationwide

If you want to learn more about me, take a look at my recommendations – they come from former co workers, bosses & competitors in the Ed tech space 🤓

I’m Jacob (Chief DODO—the District Office Door Opener) who has spent 18+ years unlocking meaningful collaborations between EdTech innovators and school district leaders. 

Who I help:
I guide EdTech companies—new ventures or established names like Stride K12, aiEDU, Outlier (now Savvas), Gladeo, and more—to break through cold outreach fatigue and connect with decision-makers in a constructive, human-centered way.

What I solve:
Most vendors fall short because they lead with product pitches. I flip that approach—starting with empathy, preparation, and curiosity—to build trust and tailor solutions to district pressures and needs. It’s strategic outreach that becomes authentic partnership.

Why it matters:
I’ve personally delivered about $50M in sales across giants like McGraw Hill, C2 Education, Revolution Prep, Collegewise, Varsity Tutors, and Spark Education—earning a reputation as a top EdTech sales leader. 

Recent wins include:
🔹 National grant partnerships for aiEDU + Google to impact rural students across the US
🔹 Facilitating meetings with 80+ superintendents for Virtu.Academy
🔹 Building GTM strategies for Physics Wallah, TRUCE Software, and more (You can see them all in my profile)

📩 thejacobkantor@gmail.com | 📍 Based in LA | 🤝 Always happy to connect

Venture Partner

Interlock Capital is a community-driven angel syndicate and VC fund.

Once a month, we take our talents to Home Depot… and build something together. 🔨🧡

If you haven’t done one of these workshops with your little one — you’re missing out.

They’re FREE, fun, hands-on, and honestly one of the easiest “dad wins” out there.

A hammer, some wood, a little paint…
And boom — confidence, smiles, and a project they’ll talk about all day.

Highly recommend. ✔️

Chief DODO 🦤 District Office Door Opener | $50M+ in School Sales | District Partnerships & GTM Strategy | CEO, JK K12 Co |

Chiefdodo.com website update.
37 companies have submitted "work with me" info...
80/20 rule - those of you who know - you know

Open article: Jacob Kantor by chiefdodo.com

FTC Takes Action Against Education Technology Provider for Failing to Secure Students’ Personal Data

The Federal Trade Commission will require education technology provider Illuminate Education, Inc. (Illuminate) to implement a data security program and delete unnecessary data to settle allegations that the company’s data security failures led to a major data breach, which allowed hackers to access the personal data of more than 10 million students.

In a complaint, the FTC alleged that Wisconsin-based Illuminate claimed to protect the privacy and security of the data it maintains but failed to deploy reasonable security measures to protect student data stored in cloud-based databases. These failures led to a major data breach.

“Illuminate pledged to secure and protect personal information about children and failed to do so,” said Christopher Mufarrige, Director of the FTC’s Bureau of Consumer Protection. “Today’s action is an important reminder to companies that the FTC will hold them accountable if they fail to keep their privacy promises to consumers, particularly when it involves children’s medical diagnoses and other personal data.”

Fun fact for your weekend: 
LA County (10M people) → larger than 40 states in the U.S. 

Read that again. Forty. States. The more you know. ✨ 

Fun EDU fact. 80 districts in LA county 1.3-1.4m students.

When I grow up I want to be like Robert Dickson 
Check out the work in Wichita Public Schools - USD259 

I may or may not be on the treadmill listening to Brett Roer  , Rebecca Bultsma , Aaron Cuny on AmpED to 11 Podcast while reading this article 😂

Reimagining California’s Education Governance System

History of Governance Reform in California

1849–1970: Repeated Attempts to Resolve California’s “Double-Headed System”
1849 The first constitution of California established the elected superintendent of public instruction (SPI).
1852 and 1912 The State Board of Education (SBE) was created; a 1912 amendment to the state constitution gave the governor the power to appoint SBE members, splitting authority between the SPI and the SBE.
1920 The Jones Report warned that the “double-headed system” of an elected SPI and governor-appointed SBE causes conflict and recommended unifying leadership under an appointed commissioner.
1921 The California Department of Education (CDE) was formed to centralize administration under the SPI, with policy authority retained by the SBE.
1928–1968 Multiple ballot measures to eliminate the elected SPI and resolve governance conflicts were put before voters but failed.
1944–1945 The Mills and Strayer reports identified confusion, weak capacity, and unclear authority in California’s education governance and called for a single appointed SPI and stronger SBE oversight.
1963–1967 The Little Reports and Attorney General opinion reaffirmed governance incoherence and urged that the SPI be accountable to the SBE.

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