My 2020-2026 entrepreneurial journey has been interesting. One of the hardest things for me to deal with is the ups and downs. Doubly so, if you were a salaryman like I was for so long. Getting paid every two weeks, regular promotions and salary increases, expense accounts etc. Your brain gets lulled to complacency. Then when you start your business you have massive energy and desperation to do whatever you need to do to start getting money in the door. My journey started in the height of the pandemic lockdowns which was brutal.
Yet I’ve realised the hardest thing for me to deal with was the variability of results. So to recap the last 6 years:
2020: Horrific for 9 months of the year but the last 3 months turned out to be incredibly lucrative due to some exits and capital gains. GREAT
2021: Built lots of income streams and financially was a top year. GREAT
2022: Despite the Russian invasion wrecking the Ukraine-Germany business I was involved in. MEH
2023: Was solid, albeit my Core business had some challenges from a cash flow perspective. GOOD
2024: Was actually solid financially overall. Lots of new initiatives. GOOD
2025: Started off good, but then due to lots of account receivables and painful real estate investment issues that led to massive negative cash flow in the 2nd half of the year. VERY BAD
2026: So far, it’s been brutal, big tax bill (my own miscalculation) and continuing real estate investment cashflow issues, the bulk of the year was pretty awful.
But I’m figuring it out. Building some new income streams & equity positions.
Not sure why, maybe it’s an industrial age thing or education thing. For some odd reason, we think things should go up in a straight line. Not the massive upswings and downswings of reality: REAL Instability. Yet when I watch the journey of many of my portfolio companies, it was never a direct up and to the right. I don’t think it ever was. Every book I read of the great entrepreneurs and investors, their journey was never one of unrelenting triumph. Why would any of us be different?
BowtiedBull aka BTB describe this perfectly:
“If you're actually trying your best to maximize life it kinda looks like this.
Every 4 years: 1) great year, 2) meh/okay but positive progress year, 3) one bad year.
Varying degrees but has been extremely consistent and explains why most can't survive long-term.”
I’ve come to believe that the hardest thing for entrepreneurs to conquer is their psychology and mindset. Dealing with the variability. Building our ability to resist the urge to quit even when everything is going to hell around you. Taking the pain and still moving forward, doing what you need to do. I’ve realized variability is a feature, NOT a bug. This is the game.
But why is this worth it? I've written many times on how dangerous it is to be an employee not just financially but psychologically in light of where the world is going. Especially in the USA. You literally can get laid off or fired out of the blue, even after being a top performer for a decade. It’s a capitalist “at will” society: you can leave at will, and they can fire you at will.
But there is a massive prize at the end of the tunnel if you do it well. While the downside is uncapped, so is the upside. Especially in America. BTB righty says:
"The top 1% now control a far larger share of net worth than they did 30–40 years ago. That concentration isn’t a talking point to “eat the rich”. It’s proof that the mechanisms of ownership (equity, businesses and outsized capital gains) are what create generational wealth.
The top 1% share of US net worth has climbed consistently. The only reason it goes down during recessions is because the rich simply HODL through downturns. Once the market comes back, they go back to taking more of the pie.
If you want a real way out, not just a better salary to “invest $10K more per year”, build something that creates recurring cashflow and a real equity stake.
Control pricing, systematize the business, and let compounding do the rest. The risk is real; the upside is structural — and the difference between owner and worker is not moral. It’s permanent.
The same politicians claiming to be for the people, are playing this same game. Year after year after year. The figure head changes, the incentives don’t."
Source: https://bowtiedbull.io/p/start-a-business-the-only-real-way
Business and equity ownership is THE only way to get ahead now. Your entrepreneurial journey can not just lead to great wealth but also help you deal with hardship and build the mindset to succeed in life overall. I’ve learned that entrepreneurship is really a personal development journey wrapped up in the cloak of a business opportunity.
As I have heard many times in Silicon Valley circles, pain tolerance is a moat.