Startups

The year is 2025. I’m turning 40 soon, sitting in a cramped 450-square-foot apartment with thin walls, $50,000 in credit card debt, and a credit score of 646. My financial worth: $100 in liquid assets. My net worth: deeply negative. Five years ago, I was worth over $7 million. This isn’t a story about market crashes or economic downturns. This is a story about human fallibility—specifically, mine. If you’re looking for a cautionary tale about greed, overconfidence, and the psychological pitfalls of sudden wealth, welcome. I’ve lived it all so you don’t have to.

Two Paths to Achievement # There’s a profound difference between what I call growth and grind mindsets that shapes how we approach challenges and pursue success. Growth represents an organic process of continuous learning, skill development, and personal evolution that naturally tends toward expansion and improvement. Grind, conversely, focuses on sheer effort expenditure—often pushing beyond sustainable limits into exhaustion or burnout territory. While growth feels expansive and energizing, grind typically feels constrictive and depleting.

A fascinating pattern has emerged among startups—particularly in financial technology and adjacent sectors—where leaders increasingly explore cultural propagation through memes as a potential growth strategy. This approach parallels the “viral” focus that characterized the early 2010s startup landscape, when numerous companies secured substantial venture funding based primarily on rapid user acquisition through novel applications. The Yo app stands as a particularly interesting historical example of this phenomenon.

A recent discussion on Reddit about entrepreneurship prompted me to reflect on a fundamental question: What motivates entrepreneurial pursuits despite their significant inherent challenges? This question becomes particularly relevant for those with limited initial resources or established networks. Personal Motivations for Entrepreneurship # My perspective on entrepreneurship centers on two core aspirations: applying valuable skills to work I find meaningful, while creating sufficient economic stability to live comfortably without financial anxiety. This framework prioritizes purpose and sustainability over wealth maximization.

One of the fascinating realities in the startup ecosystem, particularly within venture-funded companies, is how perception can sometimes outweigh immediate fundamentals in determining valuations. Many founders successfully secure substantial funding at impressive valuations based largely on the promise and potential of future business growth rather than current financial metrics. The Venture Capital Incentive Structure # The venture capital model operates with a distinctive incentive structure. VC firms typically earn revenue through management fees calculated as a percentage of assets under management, with additional performance incentives when investments appreciate in value. This structure naturally encourages pursuit of companies that can rapidly increase in valuation and attract subsequent funding rounds at higher prices.

I’ve long aspired to build a sustainable, successful startup—one that generates sufficient revenue to support itself and provide meaningful compensation to its team members. However, I’ve reached a point where honest self-assessment has led me to pivot toward employment opportunities rather than continuing down the founder path for now. This journey has offered valuable insights worth sharing, particularly about the gap between startup mythology and actual entrepreneurial reality.

The Chemistry of Reward # Dopamine is a chemical in our brains associated with pleasure and reward. Rather than explaining it myself, I’ll share a quote from the book “The Righteous Mind: Why Good People Are Divided by Politics and Religion”, (pp. 102-103):

While I typically maintain caution around predictions, I believe we’re witnessing the early stages of a significant business model evolution. An emerging category of ventures—what I call “incentive-aligned businesses”—appears positioned for substantial growth and impact in coming years. The Principle of Mutual Risk and Reward # The concept of “skin in the game” describes arrangements where participants share both risk and potential returns with their counterparties. This principle already operates in certain investment contexts—angel investors provide capital to founders, accepting significant risk in exchange for equity that may grow substantially in value if the venture succeeds. This structure creates natural alignment between parties as their outcomes become interdependent.

Make something people want Y Combinator’s guiding philosophy—captured in their motto “make something people want”—has influenced countless entrepreneurs since its first appearance in Paul Graham’s blog post on startup fundamentals.