I never worked pretty much any job until I was 20; it was the first paid professional thing I'd done (which I know isn't crazy, yet is still something to appreciate). The reason I mention it is for the context that I had no benchmark for what work really was, only what other people had to say about it.
The job was at a small proprietary trading firm of about 20 people, that was pretty much an extremely well capitalised startup. It actually started off pretty chill with some training, and I wasn't actually allowed to talk to anyone on the trading floor in the few hours I was allowed to shadow them during the day. But by the time I got into the thick of it, my threshold for hard work/intensity got completely recalibrated. I remember somebody giving me a heads up before I started that "it's going to be baptism by fire."
I won't get into the details, but it was an incredibly unique place to be: the first intern at the overlap between a crazy startup and a high intensity finance job. I actually had no qualms with the intensity, or the reward (as far as things go, trading is a pretty equitable career to be in).
But I recognised that I liked living at that speed, and no matter what it was I was doing, a challenging environment was something I was going to have to get used to. Whether it was being glued to a trading desk, or building a startup, the challenge will be there regardless.
The question then becomes: how much equity do you have in your hardship?
The rest of this works off the assumption you are onboard with working hard.
This is my own way of putting some numbers behind it and thinking about it my way. The best pieces I've come across and remember about why startups make sense (but note none of these I actually read or found before starting!):
- Naval on how to make money
- Ben Horowitz Hard Thing About Hard Things
- Graham Weaver
- Marc Andreessen why not to startup
Capital Allocation
In big orgs, the relationship between effort and reward is relatively linear. One's contribution, while potentially substantial, ultimately feeds into a larger system where value is distributed across many stakeholders.
Building something presents a different capital structure entirely. Initial resources are typically more constrained, but the allocation of returns is fundamentally different. Each improvement, each solution, and each innovation flows back more directly into the venture's value.
Compound by Motivation
Once you're onboard with the fact that you structurally benefit from building, there's an additional crucial sometimes overlooked advantage too: your capacity for getting things done increases dramatically -- leading to even more aggressive compounding in your favour.
This hinges on the fact you believe in what you are doing and what it could become and you are genuinely interested or passionate about the thing itself.
When it's your own thing, everything intensifies. You dig deeper into problems because the solutions directly impact your success. You learn faster because every insight translates to immediate advantage. The satisfaction of progress fuels longer hours and harder work. And perhaps most importantly, there's no ceiling on the potential return - your upside grows with every improvement you make.
AI as a Multiplier
Current technology doesn't reduce the fundamental challenges of building. Instead, it amplifies potential outcomes. AI, no-code tools, and cloud infrastructure don't make the path easier - they expand what's possible with the same input of effort and resources.
This creates an interesting dynamic: while barriers to entry are lower, the potential scope of what can be built is vastly larger. The challenge has shifted from access to tools to the ability to deploy them effectively.
Time Multipliers
Trading taught me something applicable here: While perfect timing is impossible, time in the market matters more than timing the market. Each day spent building compounds, regardless of market conditions.
This applies doubly to building in technology, where learning compounds and initial advantages often strengthen over time through network effects and accumulated knowledge.
Soft Multipliers
When you do hard things:
- You build resilience
- You develop rare skills
- You create unique insights
- You attract like-minded people
And when you do this for yourself rather than an employer, these benefits compound exponentially.
Risk Profiles
The risk profile of traditional roles is well understood: steady progression with predictable milestones. The entrepreneurial path presents a wider distribution of outcomes, but with notably different tail risks and opportunities.
As Alok Sama observed in his study of Masayoshi Son and SoftBank, the greatest risk often isn't in failure but in never attempting. The choice isn't between comfort and difficulty - it's in how that difficulty is applied.
Everything is on the other side of worse first.
The Calculation
The calculation is straightforward: If the path will be challenging regardless, the expected value depends largely on where the returns flow. Modern tools don't make things easier, they simply increase the potential scope of what can be built.
This creates an interesting optimisation problem: how to maximise the expected value of one's effort given the available paths. The answer isn't universal, but depends heavily on individual circumstances, risk tolerance, and the specific opportunities at hand.