Success brings knowledge, but it also creates a bias against trying unconventional ideas. Early-stage entrepreneurs are "too dumb to know it was dumb," allowing them to take random shots with high upside. Experienced founders often filter these out, potentially missing breakthroughs, fun, and valuable memories.

The essence of the entrepreneurial journey is the ability to tolerate immense uncertainty and fear over long periods. It involves working for months or years with little visible progress, making high-stakes decisions with limited information, and shouldering the responsibility for others' livelihoods. This psychological endurance is the ultimate differentiator.

Contrary to popular belief, successful entrepreneurs are not reckless risk-takers. They are experts at systematically eliminating risk. They validate demand before building, structure deals to minimize capital outlay (e.g., leasing planes), and enter markets with weak competition. Their goal is to win with the least possible exposure.

The best time to launch a company is at the bottom of a recession. Key inputs like talent and real estate are cheap, which enforces extreme financial discipline. If a business can survive this environment, it emerges as a lean, resilient "fighting machine" perfectly positioned to capture upside when the market recovers.

Founders often start scrappy out of necessity and dream of lavish resources. However, once successful, many realize that small, lean, and scrappy teams are more effective. This creates a paradox where the most successful entrepreneurs intentionally revert to the resource-constrained mindset they once tried to escape.

When competing against a resourceful incumbent, a startup's key advantage is speed. Bizzabo outmaneuvered its rival during the pandemic by launching a virtual solution in weeks, not months. This agility allows challenger brands to seize market shifts that larger players are too slow to address.

Many self-proclaimed capitalists embrace the system only when it benefits them. True entrepreneurship involves accepting the risk of being outcompeted without complaint. Crying foul or seeking protection when a bigger competitor emerges reveals a hypocritical stance on free-market principles.

Companies like Instagram that succeed early become risk-averse because they lack experience in navigating failure. In contrast, enduring early struggles builds resilience and a willingness to experiment, which is critical for long-term innovation.