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?

Coastal Capital Advisors

We help people in tech maximize their wealth, optimize their equity compensation, and pursue their dreams.

We believe that investing now with the right plan in place will lead you to reach your dreams, whether that’s taking a year off work to travel the world or an earlier retirement.

Founder & Financial Planner

Procore Technologies

Account Executive I Mid Market

Inside Sales, Enterprise Account Executive

Business Development, Strategic Accounts

I work with large construction managers and general contractors to help their teams become more efficient, collaborative, and ultimately, more profitable

Enterprise Business Development

Procore is a cloud-based construction management software application built for the construction industry professional, striving to make project management effortless, one task at a time. With Procore’s easy-to-use and collaborative software, users can manage their projects at anytime, from anywhere, with any Internet-connected device. Since their founding in 2003, Procore has earned a spot on the Deloitte Technology Fast 500 list and named one of INC.’s 500/5000 Fastest Growing Companies for the third year. For more information about Procore Technologies, or for a free online demo, visit http://www.procore.com.

As a Business Development Representative at Procore, and an expert in the construction software industry, the services I provide are simple:

- Understanding your business, the challenges you face, and your company goals
- Assist prospective clients in gaining a clear understanding of the construction software industry as a whole
- Explain clearly both what Procore DOES, and DOES NOT, do
- Identify the optimal solution based on a company's needs

Business Development Representative

Travel

I traveled to Australia, Singapore, UAE, Turkey, Argentina, Chile, Peru, Ecuador, and various parts of the United States.

I learned how to adapt to unexpected circumstances and devise new plans due to intermittent travel mishaps and unforeseen events.

I refined language and communication abilities through dealings with people from around the world. I learned to use both non verbal and verbal communication to surmount communication and language barriers.

Traveler

Citi

•	Proactively execute integrated sales, service and relationship strategies to support growth and retention of business customers
•	Develop new business relationships, as well as fulfill client needs for existing clients, through segment-based sales plans and communication Citi’s value proposition to achieve revenue growth targets and maximize operating capabilities and profitability. 
•	Act as a trusted advisor to clients and direct them through financial matters by educating and counseling them in order to increase client satisfaction and product engagement
•	Solicit clients actively via telephone, mail, referrals, and high level networking
•	Maintain close contact with clients and provide full customer service, both proactively and on demand
•	Ensure compliance with all legal and regulatory requirements
•	Assist in training of new team members
•	Recognize early warning signs and monitor clients to anticipate changes in risk rating
•	Proactively identify issues and restructure relationships to mitigate potential future risk

Associate Relationship Manager

•	Successfully completed Citigroup’s highly selective 10-week formal Commercial Credit Training program orchestrated by Citi’s Independent Risk organization, consisting of advanced topics in accounting, financial analysis, credit underwriting, and the overall credit process from prospecting to deal structuring
•	 Execute sales, service and relationship strategies to support the Orange County Commercial Banking team’s portfolio growth and retention of business customers with annual revenues between $30 Million and $1 Billion
•	 Underwrite commercial mortgages, term loans, lines of credit and other credit products for middle-market clients
•	Analyze and evaluate the creditworthiness of companies through historical and forecast financial models to determine debt service capacity and financial condition

Business Analyst

AppFolio Inc.

•	Utilized computer knowledge to move client’s data to online format.
•	Daily telephone/e-mail contact with clients to assist them in transitioning to the new software
•	Rewrote and clarified the process for training new hires
•	As a result, this led to increased customer satisfaction by providing timely assistance to clients, as well as an improved training process for new hires.

Implementation Specialist

Meem Media

•	Started a social media management company working with organizations to improve communication through various social media applications
•	Duties include marketing, sales, program design and launch, and remote maintenance of social media programs
•	These efforts led to high customer satisfaction and increased market share for Meem Media

President

From 2016 - 2020, I worked in software sales for Procore, but I was burning out and I felt stuck.

So in 2020, I decided to walk away from my high-paying tech job.

But, before I did, I had a hunch.

I believed tech employees (and Procorians specifically) were ignored by the financial services industry. 

While the industry wanted to serve retirees who had already made it with big portfolios, there are a large number of high income tech professionals in my generation that want and need planning now, not in 20+ years.

So we launched Coastal Capital Advisors in early 2020, and now I build financial plans for Procore employees and their families so they can avoid the burnout and become work optional.

And the results have been pretty fantastic.

Since then, I've helped Procorians:

→ make decisions around their Procore equity
→ navigate their Procore benefits
→ optimize their cash flow 
→ maximize their 401(k)
→ buy houses 

If you want to learn more about how we work with Procore employees, there's 3 ways I can help you.

1) THE TECH FINANCIAL PLANNING NEWSLETTER

Join 1,100+ tech professionals getting a 5-minute (or less) email on the 1st and 3rd Saturdays of each month about financial planning, taxes, investments, and company stock

→ GO HERE: https://mailchi.mp/fd781696f237/tfp-landing-page

2) THE FINANCIAL PLANNING FOR PROCORE EMPLOYEES WHITEPAPER

Many of our clients are current and former Procore employees.

As a result of this experience, we've attempted to point out the unique financial circumstances and opportunities that Procore employees face.

→ GO HERE: https://mailchi.mp/751de6c609df/procore-whitepaper

3) WORK WITH ME 1:1

You'll need 4 things to build your successful and secure financial plan

▪️ 𝐄𝐪𝐮𝐢𝐭𝐲 𝐂𝐨𝐦𝐩 𝐏𝐥𝐚𝐧𝐧𝐢𝐧𝐠 - Make the most of your company stock
▪️ 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 𝐏𝐥𝐚𝐧 - Make sure you are saving the right amount and using the right accounts
▪️ 𝐈𝐧𝐯𝐞𝐬𝐭𝐦𝐞𝐧𝐭 𝐏𝐥𝐚𝐧 - make sure you're set up in a way that fits your larger goals
▪️ 𝐓𝐚𝐱 𝐒𝐭𝐫𝐚𝐭𝐞𝐠𝐲 - Pay the least amount of tax over your lifetime

Want to get started?

→ GO HERE: https://calendly.com/joe-marshall-cca/get-to-know-meeting

Joe Marshall

Since September, I’ve met with 59 tech professionals. Here are the 5 biggest “tax thieves” I keep seeing - the ones quietly stealing money from people, and they don't even know they've been robbed. 

1) Only thinking about AMT when you exercise stock options
Most people only consider AMT at exercise (if they consider it at all). But AMT affects both exercising and selling.

Here’s the issue:
- Selling stock options triggers two tax calculations: regular tax and AMT
- Most people only think about the first
- If you ignore AMT, you could overpay, and you might miss out on using AMT credit

AMT is a full-journey tax. It matters from exercise to sale.

2) High-income earners incorrectly contributing to IRAs or Roth IRAs. This one is sneaky.

When your income is above IRS limits, direct IRA or Roth IRA contributions get tricky, and you have to follow the rules / steps correctly, otherwise you're creating a big mess.

Plus, you might pay tax twice on the same money, or you might have to unwind the contributions.

3) Inefficient investments - most people have no idea this is happening.

Typically I see this with a big, actively managed mutual fund. Typically something a grandparent told them about, or an old advisor. The problem is that these funds can kick off large capital gains distributions every year, no matter how the fund did that year (up or down).

So you're being forced to pay taxes, even if you didn't do anything. 
 
And most of the time these funds are also more expensive than simpler alternatives.

4) Not reporting cost basis correctly on company stock

RSUs, ISOs, NQSOs all have different basis rules. If basis is reported incorrectly (and it often is), you end up paying tax on income you already paid tax on.

I see this constantly: someone sells their RSUs, they report the wrong basis, and suddenly the IRS thinks they made a huge gain.

Fix the basis.
Report it correctly.
Save yourself the unnecessary tax bill.

5) Selling company stock randomly. Most people just… sell whatever shares they feel like. Or show up first. Or whatever advice they heard on slack. 

A better approach is actually planning for your sale than reacting to the stock price. 
- typically, prioritize lots with the smallest gains
- but when selling ISO shares and factoring in AMT credit, more strategy is required.

---
Tax planning isn’t always the “secret strategy” you saw on TikTok (that might also be fraud, or at the very least, a terrible fit).

Most of the real savings come from ruthlessly executing the basics correctly and making sure you’re reporting everything properly, in tandem with a good tax preparer. Especially when equity compensation is involved.

These aren’t theoretical ideas.

They’ve saved clients tens of thousands of dollars, and in one case, more than $200,000.

If you work in tech and have equity, this stuff matters.
A few small mistakes add up.
One big mistake can send you sideways.
A few smart moves can pay for themselves many times over.

I exist so tech professionals don’t have to stress about money. I plan for them. I Founder @Coastal Capital Advisors I Girl Dad

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Joe Marshall

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