👋 Hey, it’s Andrew.
I just got back from Austin, where I stayed up cheering Nicole on as she ran 50 consecutive miles through the night, from 6 pm to 5 am. She is the most inspiring person I know.
While I was there, I had a lot of time in solitude to think about life and career. Today’s post is more personal. It is a transparent reflection on where I am today and where I am heading next. If this resonates, I’d love to hear your thoughts.
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I remember a vivid conversation with my best friend, Simon, about a decade ago. We were living in Shanghai at the time, talking about how our dream was to live and work in New York City one day. It felt distant and unreal. America seemed like this magical place on the other side of the world. But I could picture us sitting on the ledge of some skyscraper in Manhattan one day, looking out and saying, “Wow, we did it.”
I also had this dream of working in a big multinational company, something with marble lobbies and forty floors. I think Suits got to me. I wanted the feeling of being part of a real institution.
Then I dreamed about working for a tech giant like Google or Facebook. I wanted to be inside one of those companies everyone talked about. To feel like I was part of something shaping the world. The perks and culture were just the cherry on top.
Each dream felt impossible at the time. But somehow, over the next decade, they all came true. I worked at the big companies. I spent time at Google and Facebook. I live in New York now.
And the strange thing about dreams is that once you achieve them, you think of new ones. Because when a dream ends, it leaves behind this quiet space where you have room to think again. And in that quiet, new questions show up. Questions you weren’t ready to ask before. What now? What else? What more is possible?
Along the way, I took an unexpected detour. I never imagined being an entrepreneur or running my own thing. Most people go into this path because they want freedom and autonomy. I never craved that. Not at first. But once I got a taste of it, something changed.
There is a lot that is rewarding about working for yourself. The financial upside, the flexibility, the sense that your life is fully yours. But there is also a different kind of pressure, like accountability, the uncertainty, the loneliness.
I’m 30 now. I’ve been working for about eight years. I think of this as my second career. The first one was the corporate chapter. I learned a lot, made a little money, and built some credibility. Now I’m in the early innings of entrepreneurship. I’m learning new things again.
If I work hard until I’m 60, that means I have around 30 years left. Which is about 80 percent of my career still ahead of me. And everything meaningful takes around 5 to 10 years to build. So realistically, I have about four careers left.
So the question becomes: what is my next dream?
How to Make Your Dreams Come True
When I ask myself this question, I try to remove all logical constraints. I try to remember what my younger self would have wanted before I learned about limitations.
I’ve always dreamed of building something big and cultural. Something that has a physical presence. A physical office filled with hundreds of people. A team. A company that plays a role in shaping culture. Something like Time Magazine, Disney, Starbucks, Lego, or Levi’s. A brand people feel connected to. Something that adds joy, meaning, or belonging to their everyday life. A company that becomes part of how people see themselves. An iconic brand everybody knows.
Obviously, that is insanely ambitious, but again, the whole point this is to dream.
So how do you actually make dreams like that come true?
This is the same framework I’ve used to make all of my past dreams come true, from New York to Google to building my own thing now.
1. Remove the logic.
When you start by asking what is realistic, you cut your imagination off at the knees. Dreams are supposed to feel too big at first. They are supposed to be a little embarrassing to say out loud. The dream comes first. The plan comes later.
2. Ask your 10-year-old self.
The younger version of you knew what lit you up before the world taught you to care about practicality, salaries, prestige, or what makes sense. Ask that version what would make him smile uncontrollably. That answer is usually closer to your truth than anything you can rationalize now.
3. Think in decades.
Everything meaningful takes time. Muscles take time. Companies take time. Reputation takes time. If the dream is big, it will feel slow at first, but that doesn’t mean you’re failing. The people who win are the ones who stay in the game long enough to let compound effects do their work.
4. Reverse engineer it.
Once you know the dream, work backwards from the future version of you.
What skills does that version of you have that you don’t yet?
Who are they surrounded by?
What rooms are they in?
What shaped them?
Create a list of requirements that close the gap between who you are now and who you want to become. Then execute every line on that list.
5. Say it out loud.
The moment you share your dream, the world starts reacting to it. When you declare who you want to become, people who recognize that version of you begin to find you.
And honestly, this might be the most important part.
Every dream I’ve ever had only started taking shape once I said it out loud.
Once you let the world know, it starts to rearrange itself in ways you couldn’t predict. People show up, doors open, and paths you never even knew existed begin to appear.
So let me ask you something:
What are you dreaming about right now?
I’d love to know.
👉 Hit reply and tell me.
If you’re bold enough, post it on LinkedIn and tag me!
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📌 Andrew’s Bookmarks
My favorite links to help you be wiser and more creative.
EYEBALL, A NEW KIND OF BOOKMARKS APP – A new tool I discovered recently for smart, curious people. It effortlessly saves your links, automatically adds summaries, and sends a hyper-personalized update every Sunday morning about what you saved. Created by a writer, used by thousands of people.
The AI Wildfire Is Coming. It’s Going to Be Very Painful and Incredibly Healthy by Dion Lim – Despite the title, a surprisingly grounded prediction on the upcoming 3–5 year AI cycle to answer the question, “Are we in an AI bubble?”
What’s next? by Jodie Cook – A helpful perspective on those searching for their next thing – whether it is a big career or personal decision. A quote that struck out to me, “Not all those who wander are lost.”
Better Than Free by Kevin Kelly – When things on the internet can be copied endlessly (and nearly free), the value shifts to qualities you can copy. Kevin talks about them here.
Austin Nasso: Impressionable Youth – My friend Austin Nasso is the funniest guy I know in tech. He launched his comedy special this week. Check it out here.
💼 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 Coordinator (Full-time + Part-time available), Fibe – reply here
Content Manager, Perplexity
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.
👉 Btw, if you want to be part of our partner talent network, next play, and get curated job opportunities in your inbox, please sign up here.
💃 Tech Community Plugs
Resources for entrepreneurs, investors, and tech professionals.
⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.
💸 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.
⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.
📺 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.
🖼️ Behind the Scenes
I still think Austin is one of the most underrated cities in the US.
Why:
Friendliest people I’ve met
But also smart people – a lot of retired/exited entrepreneurs and executives settle down here
Ubiquitous fitness culture – people here are healthy and happy
Lots of space and beautiful nature
Affordable housing
GREAT food (esp. if you love BBQ)
I recommend visiting.
I am a dreamer
Reverse engineering from your future self is basically manifestation for people who hate manifestation, and I'm here for it.