👋 Hey, it’s Andrew.
Our team just got back from Leesburg, Virginia, where we took over a private resort for three days with a few hundred founders, investors, and operators. We played pickleball and board games, told stories around the campfire, and founders even had the chance to pitch for $1m.
Little did I know that Loudoun County (where the resort is located) is the wealthiest county in North America, with a median household income of ~$179,000.
Why: federal contracts and employees from DC, demographics – it has the highest rate of college-educated adults in the US, and there are a TON of tech and data centers. >70% of global internet traffic is estimated to route through this area, with Amazon, Google, Meta, and Microsoft having data centers there. Fun fact.
Speaking of wealth… keep reading.
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Nov 13 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series for Seed–Series B founders & CEOs.
Nov 14 | ☕️ Founder Breakfast (NYC) – A curated breakfast for 30 early-stage founders and investors (venue TBD)
Nov 19 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series for Seed–Series B founders & CEOs.
Dec 10 | 🍽️ Junto Founder Dinner (NYC) – Our curated dinner series for Seed–Series B founders & CEOs.
Dec 12 | ☕️ Founder Breakfast (NYC) – A curated breakfast for 30 early-stage founders and investors (venue TBD)
In my last article, The Paths to Building Wealth (Part 1), I talked about the most common paths (I’ve seen) to building wealth.
Finding a stable, high-paying W-2 job in tech, consulting, finance or law
Being a corporate athlete with a side hustle
Building an equity or cash business
Becoming a creator
You’re probably familiar with most (if not all) of these paths and might know someone pursuing these paths.
One of my obsessions has always been finding the most unconventional ways to make money, build a career, and ultimately, create a life on my own terms.
Today, I want to share the less common ones I’ve found.
These are the careers that make people say, “Wait… you can do that for a living?”
The ones most people from my old corporate life have never even heard of.
So let’s get into it – starting from the most common to the least common. Starting with number 6.
6. Riding a Rocketship
Some people get rich by joining the right startup and getting equity that converts at a liquidation event. They manage to place themselves in the right place at the right time. I wrote about it in my past blog post, The Startup Path to Success.
If you can land in the sweet spot of a rocketship – a fast-growing tech company, usually between the Series B and D stages – you can get enough equity for it to be worth a lot of money when the company exits.
A role at a company like this usually also comes with faster career progression, more responsibility, frequent pay raises, and a bunch of other cool benefits.
But the trickiest part is picking the right company.
Honestly, beyond that, you don’t have much control. You have to believe in the leadership team and product, and you might be dedicating many years of your life to a bet that might not even pay off.
Luck plays a massive role, and this path has one of the largest outcome variations here – if you knew how to predict the winners with perfect accuracy, you would be the richest person in the world.
But if you’re fortunate, this path can be life-changing. Not just financially, but professionally. The early employees at unicorns gain access to capital, networks, and knowledge that set them up for the rest of their careers, and many will go on to join other successful startups, launch their own companies, or build strong personal brands that keep opening doors.
7. Indie Hacking
Then we have the indie hackers – the scrappy solo entrepreneurs who build mobile apps, digital products, courses, eCommerce companies, and other short-term projects.
The key phrase here is short-term.
Indie hackers are typically focused on building small, profitable projects instead of longer-term businesses. They aim for base hits, not home runs. Most run multiple income streams, don’t raise venture capital, and try to be profitable from day one – often with 80%+ gross margins.
Levelsio is the poster child of indie hacking. He publicly shares all his projects, and right now he has 7+ projects that collectively generate $600K+ a month in revenue. That’s over $7m a year!
Levelsio is obviously in the top 1% of indie hackers, but I know several other people who are doing fairly well and love this career path. It’s fun, creative, and stress-free, BUT I’ve heard many of them are unfulfilled.
Why? Because they lack a larger purpose beyond making money.
When your work is just selling apps and courses, eventually you hit a wall and ask, “What’s my mission here?”
That said, I think indie hacking is the best entry point for new entrepreneurs. It’s a single-player game. You don’t need a team, funding, or permission. You just start building. And if something doesn’t work, you move on to the next idea.
(Shameless plug for my friend Henrik’s new company, Audos, which helps people build what he calls a “donkeycorn” – a $1M business.
8. Brokering High Value Deals
This path is reserved for the top 1% of salespeople in the world – the hunters.
They find rare opportunities to sell expensive things and take a percentage of the deal for brokering the transaction.
The name of the game is to access more and more rare, expensive things. You start by selling a $1m condo and move your way to selling a $50m mansion. And if you sell that mansion, that’s a million bucks in your pocket. Also, you become known as the guy who has access to mansions, and more people will come to you. A flywheel effect begins.
It doesn’t just have to be mansions, though. It could be jets, cars, vacations, art, and investment opportunities. But you can’t sell everything – you need a niche.
If you spike high on charisma, are a bit of a socialite, and want to get rich by making introductions, this is the path for you. Go into sales where you can get a piece of the pie, then grow the size of the pie.
Real estate and software are great starting points – they’re accessible and teach you the fundamentals of selling. The downside is they’re commoditized markets. But if you can sell something commoditized, you can sell anything.
9. Selling Rare & Specific Knowledge
These are the one-of-a-kind technical specialists who become “experts for hire.”
Their titles usually include Advisor, Consultant, or Fractional Executive. They charge by the hour, per project, or on a monthly retainer. Some even take equity.
Example: Nikita Bier, who is known as the world’s most prolific app builder and virality expert, charges $60K a month for mentorship or ($15K for a 15-minute call). He constantly sells out.
He is the only person in the world who has his specific knowledge and skillset and was even recruited by Elon Musk to run product for X.
Conventional wisdom says you can’t build wealth by selling your time for money. That’s mostly true – unless you can charge a high enough rate or package your knowledge across multiple income streams.
The key is to develop rare, specific, and valuable knowledge in a niche few people understand. If you can become the go-to expert in something truly unique, you can charge $1,000 an hour (or more) and still have people lining up to work with you.
10. Hunting for Mispriced Assets
Finally, we have the investors – the people who seek arbitrage opportunities and make money by finding mispriced assets.
Public market investors work at hedge funds and mutual funds, trading equities, stocks, and bonds.
Private market investors operate at private equity firms, venture capital funds, or as angel investors, betting on companies before they go public.
And then there are alternative investors — the ones buying crypto, collectibles, or obscure financial instruments. (I still don’t fully get them.)
Across all of these, the game is the same: build a track record of profitable investments and manage more capital.
Then you take a percentage of the profits AND a fee for “managing” their money, usually around ~2%. This is how you make the big $$$.
I’ve seen “solo GPs” – individual fund managers who manage a $50m fund themselves, taking home $2m in fees every year… plus profits (usually 20%)!
But it’s really, really hard, and meant for the top 0.01%. You need to either be a brilliant investor or an amazing fundraiser.
Most of the people I’ve met who have done well in this field are either extremely analytical + insightful, well-connected, very lucky, or came from a lot of wealth.
Honestly, this seems like the coolest path to get rich, but maybe it’s because I understand it the least. It’s a bit of a black box, and nobody ever talks about their success strategy because why would you give it away if it’s working for you?
Choosing Your Game
Each path has tradeoffs. There’s no “better” one, only what fits you.
It depends on your zone of genius.
Some people thrive in structure and predictability, others crave risk and independence. The game you choose should match your personality, your strengths, and how much uncertainty you’re willing to tolerate.
Across every path, though, there are a baseline skills that will help:
Sales and people skills – learning how to persuade, influence, and build trust.
Organization and execution – getting things done consistently.
Network building – surrounding yourself with the right people.
Communication – being able to write and speak clearly.
These are the table stakes, and you should be proficient at all of them.
Beyond that:
If you want a steady, guaranteed path, take the W2 or corporate route.
If you crave risk and asymmetric outcomes, build a business – cash or equity – or hunt for mispriced assets.
If you’re a people and network person, broker deals or play in asset markets where trust and access matter most.
If you prefer single-player games and love to tinker, go the indie hacker, creator, or sell your expertise.
If you’re deeply analytical or an expert in a niche, a W2 role, indie hacking, or a selling expertise path can work well.
And if you don’t want to work for anyone else, Build a business, become a creator, indie hack, or hunt for mispriced assets.
In the end, building a career is more than making money; it’s about finding your harmony of strengths and passions. Find a game that you can play for the rest of your life. The wealth will come.
📌 Andrew’s Bookmarks
My favorite links to help you be wiser and more creative.
The Ultimate Guide for Founders: How to start a Lean, AI-Native Startup in 2025 by Henry Shi and Deedy Das – A step-by-step guide on how to build a lean startup by the founders of Super.com ($200m rev/year) and Glean.com ($7b company).
Here is how I approach starting a new job by Elena Verna – A 4-step framework on how to start a new job from the current head of growth at Lovable.
Observe, assert, and validate (OAV) by Wes Kao – Why you should go behind asking “How can I help?”
How to Build a CULT by Lulu Cheng Meservey – As the former CCO and EVP of Corporate Affairs at Activision Blizzard, Lulu is the top 1% at what she does (communications and public relations strategy). She has helped some of the best leaders through their hardest moments. Here she talks about how to build a trustworthy personal brand as a founder.
💼 Job Board
Sharing job opportunities that my friends are hiring for. If we know each other well, hit reply, and I can connect you directly.
Marketing & Events Intern (Part-time), Fibe – working for me in NYC (reply here)
Events Manager, Hampton
Founding Engineer, Icon
Investor, Eniac Ventures
Chief of Staff, Knoetic
Strategic Accounts & Founder Relations Lead, Basic Capital
Founding Designer / Founding Engineer / Social Media Lead, Astro AI – Working with the former Chief Product Officer of Hinge)
Head of Engineering, Superpower
Growth Marketing Manager, Baselayer
Data Scientist / Engineer / Founding Designer, Windmill – Working with the former co-founder of Yext
Hampton
Events Associate / Marketing & Events Roles, Manifest Law
Marketing Manager, Vylit – Working directly with the former CEO of OnlyFans.
Head of Growth, Taxwire
Head of GTM, Elloe
Lead Product Designer, EZ Newswire
Business Development Associate, ModernFi
Head of Product, Limitless AI
Have a job to share? Let me know by replying to this email.
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💃 Tech Community Plugs
Resources for entrepreneurs, investors, and tech professionals.
🏃♂️ NYC Marathon Volunteering Opportunity w/ Rho – Help cheer on runners, support logistics, and be part of an incredible community moment. Volunteers will receive exclusive perks for their time!
💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.
📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.
🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.
📺 Blindspot – the best way to run Digital out-of-home ads. Through their free tool, anyone can browse, book, and place ads on over 1.5 million digital billboards. Sign up here.
🏦 Fidelity Private Shares – the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.
🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.
🍽️ InKind – the ultimate dining app for foodies—earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.
🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.
🚴 Equinox – Reply here for a free trial and discounted membership.
What other perks should I include? Let me know.
🤖 Sharpen Your AI Edge (Presented by AWS)
Thanks to Amazon Web Services (AWS), this community now has free access to a series of live webinars and podcasts on the latest AI trends and tools. I’m sharing them here because I think they’re some of the most practical resources you can use.
(Live: Oct 30) Applying Generative AI in Healthcare with AWS and NVIDIA
🖼️ Behind the Scenes
Last week, my friends and I rented a cottage in the mountains of Breckenridge, Colorado.
We screwed up.
We didn’t realize that it was 10,000 feet above sea level, and on the first day, we could barely breathe. We had to spend the whole day chugging water and laying low just to conserve oxygen. Rookie mistake.
One thing I’ll never take for granted again: how easy it is to breathe in New York.
But America is stunning. One of my goals next year is to road trip across the country and see all the national parks that people talk about.
Also, we saw a real wild fox that looks AI-generated. Nicole even made a TikTok about it and got over 1 million views.
Couldn't agree more. Thank you, Andrew, for this insightful look into wealth. It's truly fascinating how tech infrastructure and an educated workforce drive such incredible economic prosperoty. Makes you wonder how these concentrated hubs will shape global economies.
#9 is a banger 🙌