The reality of entrepreneurship at scale is not strategic ideation but constant crisis management. Vaynerchuk describes his role as a relentless series of problems ("shit on shit on shit") punctuated by rare moments of joy, a sentiment he notes is deeply understood by mothers.

Related Insights

True entrepreneurship often stems from a 'compulsion' to solve a problem, rather than a conscious decision to adopt a job title. This internal drive is what fuels founders through the difficult decisions, particularly when forced to choose between short-term financial engineering and long-term adherence to a mission of creating real value.

Contrary to conventional wisdom about delegation, the best management style for a small business founder is to be "all over fucking everything all the time." This means maintaining granular involvement in every aspect of the company—from client happiness to legal spending—to relentlessly drive daily improvements and maintain operational control.

The CEO role is not a joyful or fun job; it's a high-pressure, problem-solving position. Founders who love their craft, like software engineering, often take the CEO title out of necessity to solve a larger problem and bring a vision to life, not because they desire the job itself.

Conventional advice about work-life balance to avoid burnout is counterproductive for founders with extreme ambitions. Building a massive, venture-scale company requires a level of obsessive focus and sacrifice that is inherently unbalanced. For this specific phase of life, prioritizing the company above all else is necessary for success.

The entrepreneurial journey is mentally taxing due to constant high and low swings. The founder's coping mechanism is to anchor himself to what's controllable: delighting the customer. Focusing on product and user feedback cuts through the noise of fundraising, competition, and existential dread, providing a stable focal point.

Many people start companies seeking control over their schedule or finances. Bianca Gates warns this is a fallacy. Entrepreneurship is a 24/7 commitment where you're the "last person on the ship." Unlike a regular job, you can't just give notice and quit, especially after taking on investors.

A founder's role is constantly changing—from individual contributor to manager to culture builder. Success requires being self-aware enough to recognize you're always in a new, unfamiliar role you're not yet good at. Sticking to the old job you mastered is a primary cause of failure to scale.

The title "CEO" is misleading. A founder's real job is to be a firefighter, constantly on call to handle unexpected crises, from employee emergencies to losing major clients. This mindset shift from strategic leader to crisis manager better reflects the reality of entrepreneurship and its inherent volatility.

In a Joe Rogan interview, the multi-trillion-dollar company's CEO revealed a constant state of anxiety. This insight shows that for some hyper-successful entrepreneurs, the intense pressure and memory of near-disasters are more potent motivators than the abstract goal of success, creating an insanely lonely experience.

Borrowing a quote from Shopify's CEO, Mike Cannon-Brookes emphasizes that a founder's key responsibility is to counteract the natural decline in ambition that occurs as a company grows. They must constantly push the organization to remain bold and hungry.