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?

Aussie writer with 1B+ content views in 10 years | I teach people to use writing online to create career opportunities | Let's connect: tim@timdenning.com

I quit my eCommerce startup with 100+ employees. Then got depressed, developed an eating disorder, and got a minimum-wage job in a bank. I now work for myself and make 7-figures writing.

I'm not that smart and have no college education. The way I used the internet made the difference.

And going to a Tony Robbins event changed my mindset. He taught me to go from being a victim to be in control.

This led to:

• 1B+ content views
• Financial freedom
• Book deal with a major publisher
• Meeting my heroes (like Tony Robbins)
• Quitting my banking career forever in 2021
• Multiple successful businesses fuelled by obsession

My mission: Help 100,000 people start online businesses. 

My beliefs that drive everything I do:

- Anything is possible
- Positivity above all
- Ego is the enemy
- Challenge the status quo
- Chase obsession, not passion
- Always be kind, grateful, and a good person

How can I help you?

• Social media audience building
• Starting or growing an online business

Join my email list with 200,000+ other high performers for more helpful insights:
https://timdenning.com/start-social-hustle-linkedin-bio/

Tim Denning

I interviewed 50 people who quit their jobs in 2024.

Here's what nobody tells you.

━━━━━

They didn't quit for more money

38 of them took pay cuts. Some massive ones

The software engineer who went from $180K to doing one-off writing gigs. The CMO who became a pottery teacher. The investment banker selling surfboards

Everyone said the same thing: "I'd do it again tomorrow"

━━━━━

The pattern that shocked me:

**The 3-month mark**
Everyone hits it. Pure terror. Bank account screaming. Partner questioning. Parents "concerned."

There's a twist: The ones who made it past month 3? They never looked back.

The ones who returned to corporate? All quit before day 90.

━━━━━

What they actually quit:

• Sunday night anxiety (47/50 mentioned this)
• Asking permission to live their lives
• Meetings about meetings about nothing
• Pretending to care about Q3 targets
• The soul-crushing commute
• Being "on" from 9-5 regardless of actual work

Not jobs. They quit the entire system.

━━━━━

The money truth nobody admits:

Month 1-3: Hemorrhaging cash
Month 4-6: Ramen profitable
Month 7-9: Matching old salary
Month 10-12: "Why didn't I do this sooner?"

But 23 of them said something that stopped me cold:

"Even if I never matched my salary, the freedom is worth more."

━━━━━

The unexpected side effects they reported:

• Marriage improved (32/50)
• Lost weight without trying (28/50)
• Stopped needing anxiety meds (19/50)
• Kids said they're "different" (better) (41/50)
• Sunday became just another day (50/50)

One guy: "I didn't quit my job. I quit dying slowly."

━━━━━

Their biggest regret?

Not the money lost
Not the security abandoned
Not the benefits forfeited

49 out of 50 said the same thing:

"I wish I'd done it sooner."

The 50th? She wished she'd been bolder

━━━━━

What made them pull the trigger:

• Health scare (12)
• Kid asking "why are you always tired?" (8)
• Passed over for promotion (7)
• Random Tuesday breakdown (11)
• Watching someone die with regrets (6)
• Just... done (6)

Not grand epiphanies. Just moments of clarity.

━━━━━

The skill they all developed:

Comfort with uncertainty.

Corporate trains you to fear the unknown. Quarterly forecasts. 5-year plans. Predictable misery.

These 50 learned something better: How to surf chaos.

━━━━━

The advice they'd give their past selves:

"Your backup plan is a prison"
"Start the side thing NOW"
"The fear never goes away, jump anyway"
"Corporate security is an illusion"
"Your kids need you present, not rich"

My favorite: "Stop asking for permission to live your own life"

━━━━━

None of them had it figured out
None of them were "ready."

All of them are more alive than when they had "secure" jobs.

━━━━━

To anyone reading this from a cubicle:

That feeling in your chest? It's not anxiety.

It's your life asking for permission to begin.

What's stopping you from escaping the rat race? 👇
♻️ Repost if you know someone who needs to read this

Join my Substack: https://lnkd.in/gMkRFmj9

Most people grind 40 years at a job they hate.

So they can retire at 67 and finally "start living."

If they make it that long.

━━━━━

Met a guy last week. 66 years old. One year from retirement.

Stage 3 cancer diagnosis.

"I was so close," he said. "One more year and I could've traveled."

40 years of waiting. For nothing.

━━━━━

The retirement lie we all bought:

• Suffer now, enjoy later
• Trade your best years for a pension
• Postpone happiness until 67
• Work yourself sick for "security"

Meanwhile, your knees give out. Your energy tanks. Your spouse becomes a stranger.

You saved all that money to enjoy a life your body can't live anymore.

━━━━━

I watch 30-year-olds planning for retirement like it's the f*cking promised land.

Contributing to 401ks while skipping their kid's soccer game.
Working weekends to boost that pension.
"Just 35 more years," they say.

35 years of Sunday night dread. 35 years of "not now, I'm working." 35 years of waiting to live.

For what? To be the richest person in the nursing home?

━━━━━

The people who get it do this instead:

Mini-retirements throughout life. Not one big one at the end.

Take 3 months off at 30. Travel for 6 months at 40. Start that business at 50.

Use your energy while you have it. See the world while you can walk it. Play with your kids while they still want you around.

━━━━━

"But I need job security!"

Your job isn't secure. Ask anyone laid off after 20 years.

Your health isn't guaranteed. Ask anyone with an unexpected diagnosis.

Your retirement isn't promised. Ask the 66-year-old with cancer.

The only thing guaranteed? Right now. Today.

━━━━━

Stop banking on someday.

Someday you'll travel. Someday you'll write that book. Someday you'll learn guitar. Someday you'll actually live.

Someday is a scam sold by companies that need you to believe happiness can wait.

It can't.

━━━━━

To everyone killing themselves for a retirement they might never see:

Take the trip now. Start the side project now. Have the experience now.

Your 67-year-old self doesn't want your money.

They want your memories.

What are you postponing until retirement that you could start today? 👇
♻️ Repost to share this idea with your network.

If you want to level up your career faster, then join my unconventional Substack newsletter with 162K others: https://lnkd.in/gMkRFmj9

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Jack Raines

Tim Denning

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The Battle

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