How has increased wealth affected your fulfillment, and what are the pros and cons of success from a personal psychological perspective?
More wealth makes it hard to tell if people like you for yourself or just your money; you test with stupid jokes to see their reaction. Many cozy up for the flashy bling, even if you're not flashy yourself. You're not more fulfilled than when you were sleeping in garages and making no money—fulfillment comes from working on stuff you care about, which you did then and do now. Your impact has grown, but your personal fulfillment hasn't, leaving you to wonder what that means for your craving for impact. When broke you could follow curiosity freely; now you constantly weigh financial effectiveness, which can lead to hard days.
I do make a significant amount of money—around $300,000 per month—mainly from the school games (third-party revenue) and another community. I earn far more talking about the stuff than actually doing it, which is typical for an information product: leverage comes from teaching others, allowing them to achieve 100x results while I earn proportionally. What do I do with the money? I don't have guilty pleasures like cars; I invest it. I have friends aiming for tens or hundreds of millions in the S&P 500, but that's never been my primary motivator. When I was broke, an extra $10,000 a year would have dramatically improved my quality of life; now, extra millions don't materially affect it unless you have extreme comfort needs. I'm thankful my family immigrated from Eastern Europe around the fall of communism; they lived frugally, teaching me that a fulfilling life doesn't require a lot of money. Though I now make what most would consider a lot of money, I still find life enjoyable and fulfilling without needing wealth.
Life is great, but success brings downsides: family loves it, yet many people now see me only as a money source and want me for boards or deals. I dislike talking about wealth constantly, but it’s needed for social proof. My goal isn’t happiness—it’s fulfillment, the deeper sense of welfare the ancient Greeks called eudaimonia. I avoid frivolous spending and focus on meaningful work rather than fleeting pleasures.
Yes—I faced intense pressure to make money, including multiple eviction threats, living in a converted garage, and surviving on rice and beans for months. That experience taught me resilience, but it also reminded me that financial pressure is a constant in entrepreneurship; the key is to keep moving forward, leverage opportunities, and remember that hardship can fuel growth when you stay focused on delivering value.
I love that we're moving to more meaning-based questions — it looks like a lot of people here who've had success following the business and automation content are now at the point of asking 'what the hell is all this for?' The fact that I've helped people get to that point is basically the answer to the question for me. I want to be remembered as the sort of person who helped catalyze people's best selves. The monetization is nice, and yeah, the $500K/month goal is part flashy because it gets clicks — people go 'whoa, isn't that half a million a month' — so it is in my interest, but it doesn't meaningfully impact my life at this point. What meaningfully impacts my life is the meaning of what I'm pursuing; the things I do day to day aren't necessarily financially related. I want to be remembered as somebody who gave far more than they consumed, as a net positive impact on the world, and also as a good partner and a good man — somebody who stood up for the right thing.