Two Years After Leaving Google: The Truth About Entrepreneurship
What nobody tells you about leaving your dream job ...and if it's worth it.
š Hey, itās Andrew.
This is one of the last articles Iāll publish this year, and probably the most honest one Iāve 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 youāre earlier in this journey than me and this helps you feel less alone, then writing this was worth it.
š
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Two years ago, I left my dream job at Google. Today, Iām more fulfilled than ever - and more uncertain than Iāve ever been.
Iāve 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 donāt want to leave the house.
My first year was messy. I was constantly uncertain and directionless - Iām 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? Whoās someone whoās had success doing it this way before?
Some days Iād 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 donāt. Theyāre 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 youāre 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 Iād figured this out in month one instead of month twelve.
I became delusionally ambitious.
Because Iāve 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 canāt 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 couldnāt turn work off.
Work took over completely. Thereās that Jensen Huang (CEO of NVIDIA) line where someone asks how many hours he works a day. He says, āAll of them.ā
Most entrepreneurs I know donāt 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 thatās been on my mind. It became an obsession I couldnāt escape, and I started to lose interest in the stuff I used to love, like playing basketball, going to concerts, and reading books that arenāt 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. Itās easy to find your community and connect with them because youāre 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 āwhat are you building?ā 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 Iād just met told me he was doing $2M ARR but only taking home $80K because of runway concerns. Nobody wouldāve 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 whoād accelerate my impact.
Everything that didnāt serve the mission started to feel trivial. I stopped caring about things I once obsessed over - things that, in hindsight, were completely pointless.
Itās 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. Itās like playing a game where you know how it ends.
Entrepreneurship removes the ceiling. If youāre 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 Iād 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 āentrepreneurship.ā
My relationships became more transactional.
This is the part Iām least proud of. There are times when Iāve been the person who mentally calculates ROI while someone is still introducing themselves. āCan this person help me? Should I take this coffee?ā Itās disgusting, and I hate that I do it.
New York amplifies this. Everyoneās assessing everyone. But that doesnāt make it okay. Again, Iām actively trying to fix this, but the pull is so strong that sometimes I wonder if Iāve 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: āRemember to be kind.ā Some days it works. Some days it doesnāt.
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 donāt go well, I feel like the entire world is laughing at me. Some of these periods last months. Sometimes I donāt want to leave the house.
When things go well, I feel validated. When they donāt, I wonder if I have any value beyond what Iāve built. Every failed project feels like proof Iām a fraud. You take business setbacks personally in a way you never did as an employee. As an employee, a bad month didnāt mean you were worthless. As an entrepreneur with a personal brand, every failure feels existential. Every win feels like proof you deserve to exist.
Itās tough to live on that pendulum.
My perception of time changed dramatically.
I wake up excited and optimisticā¦ 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 didnāt 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 whoāve 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 Iām playing a video game where Iāve unlocked all the levels, maps, and quests instead of being stuck in one part of the world that is rigged against me.
The thing Iām 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, itās 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 hereās what I donāt miss: asking for permission. Having a ceiling. Building someone elseās dream.
Two years in, and I finally understand what they mean when they say entrepreneurship isnāt for everyone. Itās not because itās hard. Itās 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 canāt go back to anything else.
š Andrewās Bookmarks
My favorite links to help you be wiser and more creative.
How to Actually Look for a Job (Without Wasting Everyoneās Time) ā Auren Hoffman is the rare type of person who is always honest and direct. The best guide Iāve seen online on how to find a job.
How to Sound Like an Expert in Any AI Bubble Debate ā A grounded, neutral perspective on navigating the āAI bubbleā conversations that we all canāt seem to avoid.
The AntiāAI Bet: Why Live Sports Will Become More Valuable As Everything Else Gets Cheaper ā Why the next decade isnāt going to be all about AIā¦ but in fact, quite the opposite!
āTake Control of Your Desk,ā And Other Career Tips for ICs, Managers & Founders ā 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 ā Die Workwear is the anonymous fashion guru whoās recently blown up on X for critiquing style and fashion (including one of my posts). Worth a read if youāre into style.
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Product Manager, Cloaked
Data Scientist / Engineer / Founding Designer, Windmill ā Working with the former co-founder of Yext
Events Associate / Marketing & Events Roles, Manifest Law
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Head of Growth, Taxwire
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š¼ļø Behind the Scenes
āBurn Rateā by Andy Dunn. Read it. One of the most impactful books Iāve ever touched. Iāve 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 Iāve 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.
Thanks for sharing. Itās nice to see we tend to feel the same ways but donāt always have the community to share.
vulnerability breeds connection. inspired by this! thanks for sharing.