Daniel Vassallo

Daniel Vassallo quotes on career advice

Building a portfolio of small bets. Quarter-time with Gumroad. Building userbase.com. Creator on dvassallo.gumroad.com. Ask me anything at daniel@hey.com.

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Instead of studying how Bezos made his billions, it's much more useful to learn how someone like you is making $10K/mo.


My advice to first-time info product creators: 1. Start with a very small product. 2. Choose a topic you know well that will almost write itself. Avoid doing research. 3. Timebox production to 2 weeks. 4. Charge $10. 5. Promote it. All the lessons are in #5. Best of luck


Imagine enduring a miserable 30yr career (counting the days until your retirement), only to find retirement even more boring than your career. We like to think this is the low risk path, but that sounds pretty risky to me. You won't get a 2nd chance.


Everyone I know who worked in big tech for 15+ years is wealthy (multi-million net worth). If you want guaranteed wealth, learn to code and go work at one of the big five. But if you want to spend time with your kids without asking for permission, do what I'm doing.


If you want to break free from the clutches of full-time employment, you just need to find a way of making $275/day. - No need to change the world. - No need to conquer the competition. - No need to dominate the market. - No need to disrupt anything. Just make $275/day.


Career success in big tech is mostly attributable to timing. Being on the right project at the right time. And the most important skill is probably the ability to recognize a lucky situation and take advantage of it.


Thinking about working for yourself? Forget about failing fast. Go for the low hanging fruit first. Then take more aggressive risks once your independence is sustainable. Why? Because this approach almost never fails.


If you're pursuing income maximization, it's hard to beat the expected value of a career at a big co — trading your time for $200/hr, 40hrs/wk, 52wks/yr, for 30yrs. But an alternative is to only pursue satisfactory income, and then maximize your time doing whatever you want.


You can tell that your employer is an abusive coward when your employment contract restricts you from working wherever you want after you leave your job. The wealthiest person on earth is one such wimp.


The biggest risk of a career as a corporate employee isn’t getting fired (most people can find another job quickly). It’s the risk of becoming unemployable if your boss becomes unwilling to give you a good reference. Your career becomes dependent on the opinion of one person.


Unpopular career advice: Insulate yourself from other people’s judgment. Do the best work you can, but do it for its own sake, not to woo others. Look for feedback, but don’t ask for opinions about your work. And most importantly, don’t ask for a promotion.


Enduring a boring existence is an opportunity cost too. If your high-paying job is preventing you from designing a lifestyle that better matches your preferences, it is costing you a huge opportunity. The alternative doesn’t need to pay as much to be worth taking.


Showing up is important. Maybe it’s a requirement. But it’s definitely not enough. Lots of people showed up consistently, and still failed. The universe also needs to align with you.


You can approach your career 1. by continuously trying to prove yourself to your peers, employers, customers 2. or by doing the best work you can & whatever happens, happens The 1st tends to lead to more success. The 2nd to more happiness. And sometimes you get success anyway.


To reduce the risk of failure you have to understand who you really are (versus who you wish you are). Your preferences, not the preferences of others. Your strengths, not those you wish you had. Things become a lot easier once you're genuinely real with yourself.


To be a pragmatic programmer you have to avoid falling in love with the modern just because it is new. That infatuation will cloud your judgment about what's applicable.


Probably the best way to build resiliency right now is to imagine ways you can get an income while locked inside for a year or two. Ideally not from a single point of failure (one employer).


Overoptimism is a delusion that makes you believe life will automatically take a better course if only you manage to grab that promotion, or that new prestigious job, or that big yearly bonus. You forget that the last time you got those things you had the exact same expectations.


Next time you change jobs, take a 2 month break in between. No need to have anything planned. Just get a taste of 60 days not having to report to anyone. Many people never had a chance to experience this level of freedom since leaving school.


People often go into retirement unprepared, and their life goes downhill fast. Take a small loan from your savings and retire a little bit *right now*. Get a taste of how you'd approach freedom, uncertainty, and ample free time. Dealing with uncertainty is a muscle. Stress it.


It's much harder to leave a good job than a terrible job. Having something to lose is a real impediment to freedom. You either need to have literally nothing to lose, or you have to somehow get into that state of mind. Otherwise you'll remain chained to your status quo.


My barbell attitude to risk taking: On one hand, extreme risk aversion with things that can jeopardize my ability to stay self-employed. On the other hand, highly speculative bets with my business, which expose me to unlimited upside. No middle.

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