Someone once said: “the road to success is paved with mistakes well-handled.” Mistakes come in all shapes and sizes. Most are small bumps — easy to overcome — but sometimes they are giant potholes that would’ve been nice to swerve.
I call these expensive mistakes. They seem like trivial decisions in the moment, but have outsized impact on our time and money. One decision saved me 10+ years, another mistake cost me $700K and counting.
I’m here to expose the biggest offenders to hopefully save you some trouble.
Waiting on green lights
Three years into college, I abandoned my plan to become a doctor. At the time, it felt like the sky was collapsing on me. I couldn’t stop thinking about all the sacrifices I already made — the boring classes, the missed parties — what a waste!
It was too late to change my major. I didn’t have any internships lined up. Every sign pointed to staying the course. Thankfully, a counselor coaxed me out of my nervous breakdown.
I was so focused on the blockers that I was missing the bigger point: if you know what you want, there is no better time to start than right now. Making a hard decision when I was 20 years old saved me at least a decade of being on the wrong path.
The absolute hardest decisions are the ones that don’t have such a clear deadline. In these cases, it’s tempting to wait for green lights: once I have XYZ, then I’ll do this… You’re not ready yet, says the voice in the back of your head.
Some prerequisites are real. But everyday, more of these old guards come down. Nowadays, the question is often: have you done this before? This means doing the work, even if unofficially, outweighs collecting paper credentials.
Waiting for everything to align is like waiting for all the traffic lights to turn green before going on your trip. You might never leave.
Saying “I don’t know”
There’s a world of difference between getting the job and doing the job well.
Getting the job favors people who convince us they know what they’re doing. Doing the job well, especially in the early days, favors people who are comfortable with saying “I don’t have all the context. I’m still learning. What can I do to make things better?”
You can land a job based on perceived competency, but you can’t do it well unless you build trust. Close with confidence, open with humility.
As a first-time manager, I was nervous and awkward. I was the same age, if not younger, than the people I was suddenly managing. Looking back on it now, I should’ve addressed the elephant in the room: “I’m doing this for the first time. I’m learning as much as I can. How can I be more helpful?” “If you ever feel like things can be better, come to me anytime and we’ll address it.” I can’t tell you how many faux pas this could’ve saved me.
Money you make vs. money you keep
When I got my first real paycheck, I was stunned: where did the rest of my money go? Taxes, my friend, will always get you. They also have the honor of being an incredibly boring and lucrative topic.
All the focus on TC (total compensation) makes it easy to forget that dollars are not all equal. Some are taxed through the roof (bonuses, salaries). Some are taxed favorably (long-term capital gains). And some are not taxed at all if you’re smart (early-stage stock options). Some have insanely high upside (the right kind of equity), while others are very much what you see is what you get.
These details used to put me to sleep — and cost me at least $700K. If you join a startup, there are two acronyms that can save you hundreds of thousands, if not millions of dollars: QSBS and 83B election. There are many boxes you have to tick to qualify — most of it comes down to some form of pay a little now to save big later.
Similarly, there’s a big difference between single-trigger vs. double-trigger RSUs. I’m no tax guru, but what I’ve learned the hard way is that anytime you’re dealing with potentially big / unknown upside, it’s worth finding an expert who can point you in the right direction. It will be the highest ROI conversation you have.
Why products fail
After launching hundreds of products, I’ve found one persistent truth — most launches do absolutely nothing for the business. They fail in predictable and preventable ways. Common culprits:
- Solution looking for a problem: the tech is slick and elegant, but nobody will care if it doesn’t solve a real problem, or one that is high-priority enough to get people to adopt / pay. A warning sign you’re heading this way is too much fixation on “what” and “how”, not enough on “why”
- Solution in a competitive space: no matter what you build, it will always be easier to convert a customer who does not have a solution than to get an unhappy customer to switch. Habits are invisible chains — expensive to take off. This is why a fast-growing market (plenty of new customers to convert), and differentiation customers care about (that other players can’t easily copy) are so crucial
- Bloated solution: when you do many things just ok → you don’t stand for anything special → customers won’t spread the word → you stay in obscurity. For breakout traction, you need “love” not “like”. This is why it’s useful to focus on a niche because it’s easier to make something a small group loves than a large group with varying needs. Riches in the niches!
There’s a world of work to be done before the first line of code. The usual argument is that engineering time is too expensive to waste. While true, our psychology is even more expensive. Once we start noodling on designs and code, the clock starts. The more time we spend polishing our solution, the more attached we become, making it harder to pivot or sunset, even after lackluster results.
By doing customer interviews and de-risking the work upfront, we are not just getting smarter about the market. We are also nudging ourselves to stay focused on the problem, flexible on the solution.
Reward without risk
I’ve met two types of people at startups who are getting screwed but don’t know it:
- The person who has little to no equity relative to their comp band
- The person who joined a billion-dollar startup hoping for the upside of a rocketship with the stability of Big Tech
In the first case, this person can feel like they came out ahead. If the startup goes nowhere (statistically likely), they at least got guaranteed cash via salary. But that same person probably could’ve made more at a public company with fully liquid compensation. They carried the job risk of a startup without the lucrative career rewards. Limited skin in the game also dilutes the need to think like an owner which holds people back all-around.
In the second case, this person has a shot at winning the IPO lottery, but more likely than not, they’ll be disappointed. Why?
- Private markets have been flooded with cash, leading to increasingly bloated valuations that get beaten up in public markets, if they even make it there
- Investors and employees who get in early can make a killing while the later ones are left holding the bag
- $B+ startups have usually gone through a hiring spree, which means there are team redundancies that are ripe for layoffs if there’s a market downturn
- This means the job risk at a $B+ startup can be similar to an earlier-stage startup. It’s obvious when a startup is circling the drain; layoffs can be more unpredictable
All this to say, the risk-adjusted returns for $B+ startups are lower than most expect. The point isn’t to avoid them altogether. The point is to understand that there’s no such thing as a great opportunity without risk.
If you want that great opportunity, you’re bearing the risk somewhere. Know the risk before you take the deal.
- You don’t wait for all the traffic lights to turn green before starting your trip. So why wait for all the stars to align before doing what you really want?
- Some version of “I don’t have all the context. I’m still learning. What can I do to make things better?” can earn you trust in a new place
- Money you make ≠ money you keep. Know your taxes / find someone who does
- Failed products fail to answer: “why does this need to exist?”, “in what way is this obviously the best?”
- Avoid taking on hidden job risks without major equity upside