Two Years After Leaving Google: The Truth About Entrepreneurship

What nobody tells you about leaving your dream job ...and if it's worth it.

👋 Hey, it’s Andrew.

This is one of the last articles I’ll publish this year, and probably the most honest one I’ve written. I put everything into this because I think people rarely share the lows - they only share the wins, which makes entrepreneurship seem easier than it actually is.

If you’re earlier in this journey than me and this helps you feel less alone, then writing this was worth it.

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Two years ago, I left my dream job at Google. Today, I’m more fulfilled than ever - and more uncertain than I’ve ever been.

I’ve hosted over 200 events, written hundreds of articles, and invested over $100,000 of my own money into projects. Some days I feel unstoppable. Other days I don’t want to leave the house.

My first year was messy. I was constantly uncertain and directionless - I’m the first person in my family to start a business, the first to work in America, and one of the few in my graduating class to take this path.

On Sunday, I sat down at a restaurant alone and wrote down the truths nobody tells you about entrepreneurship:

I had no clue what I was doing.

At first, I had no idea what I was doing. I felt this way for the first year. What is this business I was building? Am I a creator? An event planner? A media entrepreneur? Who’s someone who’s had success doing it this way before?

Some days I’d wake up and genuinely have no idea what to do. No manager to tell me. No roadmap to follow.

But over time I realized I needed three types of people around me:

• Believers - people who believe in you, even when you don’t. They’re the types of people who make you feel like you can run through walls after spending time with them.

• Guides - people who teach you specific skills and show you the way. They give you the map when you’re lost.

• Proof - people who inspire you with their grit and perseverance. They make you believe that because they did it, you can too.

I wish I’d figured this out in month one instead of month twelve.

I became delusionally ambitious.

Because I’ve had a little success, I stopped seeing the world through constraints, but instead through opportunity. Once you prove to yourself that you have the capacity to do things that you once thought were impossible, you start to believe you can do anything.

Most of us are conditioned to think through limitations because when you work for someone else, there are so many things you are told you can’t do. But when you work for yourself, you only see possibilities - especially if you are young and new to the world of entrepreneurship.

I constantly found myself wondering if I could take on bigger risks, take a bigger swing. This felt dangerous, but liberating at the same time.

I couldn’t turn work off.

Work took over completely. There’s that Jensen Huang (CEO of NVIDIA) line where someone asks how many hours he works a day. He says, “All of them.”

Most entrepreneurs I know don’t have hobbies. And for the ones who do, the hobbies tend to be some sort of achievement or competition, like long-distance running or heavy lifting.

Sometimes I catch myself at a party, mid-conversation, and all I can think about is getting home to my computer to solve the problem that’s been on my mind. It became an obsession I couldn’t escape, and I started to lose interest in the stuff I used to love, like playing basketball, going to concerts, and reading books that aren’t about business. Eventually, friends started to notice and stopped inviting me to stuff. It becomes an endless loop.

I learned the love language of business.

I met more people over the last two years than in the 10 years before it because of our shared love of business. When you meet another entrepreneur, the conversation immediately jumps to ideas and opportunities. You know exactly what incentivizes each other and how to help each other. It’s easy to find your community and connect with them because you’re all marching toward the same goal - building something impactful.

But this also meant I started judging people by their ambition level. My tolerance for small talk disappeared. I became that person who turns every conversation into “what are you building?” Working on correcting this.

My relationship with money changed.

Corporate life trains you to never talk about money. Nobody discusses their salary, their savings strategy, or how they invest. I believe that this lack of transparency benefits employers - the ones who run the game - not employees. You could be getting underpaid for years without knowing it, lacking the information you need to make decisions that could change your life.

When you work for yourself, money becomes the primary language. Entrepreneurs openly discuss revenue, profit margins, tax strategies - not to show off, but to genuinely help each other. Once you accept that businesses exist to generate profit, the world starts making a lot more sense.

Last month, a founder I’d just met told me he was doing $2M ARR but only taking home $80K because of runway concerns. Nobody would’ve ever shared that at Google.

I tried optimizing everything in my life.

Nothing else mattered once I had complete clarity on my goal, and I started optimizing to maximize surface area, energy, and performance toward it.

I wanted to be healthier because more energy meant more capacity. I learned productivity systems to work smarter, not harder. I invested money to buy back time. I joined communities where I could meet people who’d accelerate my impact.

Everything that didn’t serve the mission started to feel trivial. I stopped caring about things I once obsessed over - things that, in hindsight, were completely pointless.

It’s been financially rewarding.

In corporate life, I could predict my comp 1, 3, 5 years out. I could estimate my lifetime earnings with a spreadsheet and predict the exact net worth number I was going to hit. Some people like that security, but I only saw the ceiling. It’s like playing a game where you know how it ends.

Entrepreneurship removes the ceiling. If you’re lucky and things go well, it can change your life. Your relationship with money will change completely, and every dollar spent becomes an investment with clear ROI. Your income becomes a function of your decisions.

But let me be clear, there were months when I had no idea when the next paycheck was coming from. Months where I’d check my bank account every single day to calculate how long it could last. I saw every deal as an opportunity for more time to keep playing this game of “entrepreneurship.”

My relationships became more transactional.

This is the part I’m least proud of. There are times when I’ve been the person who mentally calculates ROI while someone is still introducing themselves. ‘Can this person help me? Should I take this coffee?’ It’s disgusting, and I hate that I do it.

New York amplifies this. Everyone’s assessing everyone. But that doesn’t make it okay. Again, I’m actively trying to fix this, but the pull is so strong that sometimes I wonder if I’ve fundamentally changed as a person - and not in a good way. It takes extraordinary effort to break this pattern of thinking. Every single morning, I remind myself: ‘Remember to be kind.’ Some days it works. Some days it doesn’t.

My self-worth became tied to the business.

There are moments when I feel unstoppable - on top of the world, believing I can do anything. This happens when you speak on stage in front of a thousand people.

But these highs are always followed by extreme lows. Because I built my business around my personal brand, whenever I stop moving, I feel like a failure. When things don’t go well, I feel like the entire world is laughing at me. Some of these periods last months. Sometimes I don’t want to leave the house.

When things go well, I feel validated. When they don’t, I wonder if I have any value beyond what I’ve built. Every failed project feels like proof I’m a fraud. You take business setbacks personally in a way you never did as an employee. As an employee, a bad month didn’t mean you were worthless. As an entrepreneur with a personal brand, every failure feels existential. Every win feels like proof you deserve to exist.

It’s tough to live on that pendulum.

My perception of time changed dramatically.

I wake up excited and optimistic… Every Single Day. But the last two years felt like they went by in months. When you have tunnel vision, you lose track of how long the tunnel is. I wish I could slow time down, and the idea of killing time now feels like such a privilege.

I opened doors I didn’t know existed.

When I was in corporate, I was surrounded by people like me. The only variation in the people I met was in seniority or the types of work we did. But for the most part, we all had a similar worldview.

When I dove into the world of entrepreneurship, I started meeting all kinds of people I never knew existed.

• 20-year-old entrepreneurs who sold their companies for tens of millions of dollars.

• Olympic athletes at the top of their discipline.

• Media personalities who had mastered influence.

• Investors who make decisions every day on how to allocate their hundreds of millions of dollars.

We connected because of our shared objective - we just wanted to make it. And after a while, I realized that everybody, no matter how accomplished they are, is still trying to figure it out. Even those who’ve successfully done it before. Nobody has the answer.

I feel more alive than ever.

I used to feel stuck in a box. Now I feel like I’m playing a video game where I’ve unlocked all the levels, maps, and quests instead of being stuck in one part of the world that is rigged against me.

The thing I’m most grateful for every day is the capacity to feel an extraordinary sense of boundlessness and freedom. For the most part, I can answer to no one but myself. I can choose how I spend my time, energy, and money. At the end of the day, if I succeed or fail, it’s all up to me.

Do I miss anything about Google? Honestly, yes. I miss the instant credibility of saying where I work. I miss having a team to brainstorm with. I miss someone else handling payroll, taxes, and healthcare. I miss free lunch. But here’s what I don’t miss: asking for permission. Having a ceiling. Building someone else’s dream.

Two years in, and I finally understand what they mean when they say entrepreneurship isn’t for everyone. It’s not because it’s hard. It’s because once you taste this kind of freedom - even with all the uncertainty, the transactional relationships, the ego swings, the months where you question everything - you can’t go back to anything else.

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📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

How to Actually Look for a Job (Without Wasting Everyone’s Time) – Auren Hoffman is the rare type of person who is always honest and direct. The best guide I’ve seen online on how to find a job.

How to Sound Like an Expert in Any AI Bubble Debate – A grounded, neutral perspective on navigating the “AI bubble” conversations that we all can’t seem to avoid.

The Anti‑AI Bet: Why Live Sports Will Become More Valuable As Everything Else Gets Cheaper – Why the next decade isn’t going to be all about AI… but in fact, quite the opposite!

“Take Control of Your Desk,” And Other Career Tips for ICs, Managers & Founders – Taking control of your career means more than just doing hard work. It means picking the right environment and finding the right people to surround yourself with.

How To Develop Good Taste, Pt. 1 – Die Workwear is the anonymous fashion guru who’s recently blown up on X for critiquing style and fashion (including one of my posts). Worth a read if you’re into style.

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💼 Job Board

All the job opportunities in my network.

👉 STARTUP JOB OPPORTUNITIES: I’m creating something new to help match you with great startup job opportunities. Fill out this form to learn more (everything is completely anonymous, and your info will not be shared).

• Marketing & Events Intern, Fibe – reply here

• GTM Generalist, Antimetal

• Content Manager, Perplexity

• Chapter Lead, Hampton

• Founding Engineer, Icon

• Investor, Eniac Ventures

• Chief of Staff, Knoetic

• Growth Manager - IRL, Basic Capital

• Head of Engineering, Superpower

• Growth Marketing Manager, Baselayer

• Product Manager, Cloaked

• Data Scientist / Engineer / Founding Designer, Windmill – Working with the former co-founder of Yext

• Events Associate / Marketing & Events Roles, Manifest Law

• Marketing Manager, Vylit – Working directly with the former CEO of OnlyFans.

• Head of Growth, Taxwire

• Account Executive, V7

• Head of GTM, Elloe

• Content Creator & Social Media Marketing Lead, Escargot

• 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.

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💃 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.

• 🚀 Building in the next year? Spend 6 weeks with the Forum Ventures’ Venture Studio team to validate your concept and get the opportunity to Pitch us for $250k and a full build team. Apply here.

• 🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.

• 💸 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.

• 🏦 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.

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🖼️ Behind the Scenes

“Burn Rate” by Andy Dunn. Read it. One of the most impactful books I’ve ever touched. I’ve spent the last two years working with Andy, investing in his company, getting to know him. We just sat down in New York to record a podcast. I shared stuff I’ve never talked about publicly. My starting story. My vulnerabilities. All of it. His book did that to me. Watching him talk openly about bipolar disorder while building Bonobos gave me permission to stop hiding. The podcast drops soon. Get his book here.