Thinking Machines' custom-branded gym, revealed amidst executive turmoil, is seen as a red flag. It contrasts with the "garage startup" ethos and suggests premature spending on non-essentials before achieving significant revenue, a potential sign of misplaced priorities.
More capital isn't always better. An excess of funding can lead to a lack of focus, wasteful spending, and a reluctance to make tough choices—a form of moral hazard. It's crucial to match the amount of capital to a founder's ability to deploy it effectively without losing discipline.
The initial period of struggle and repeated failures, while painful, is what forges a resilient team and a strong, frugal company culture. These early hardships create shared experiences that define the company's DNA for years to come.
While 8% of founders pay themselves nothing to maximize reinvestment for a future exit, this strategy is often regretted. Even among founders who achieved a multi-million dollar exit, many later wished they had paid themselves at least a small salary to improve their quality of life during the building phase.
Believing the business would one day be his, the founder paid for hotels, tools, and other company expenses from his own pocket. This personal financial over-investment, without any formal ownership, is a red flag that you are acting like an owner without being compensated like one.
Beyond product-market fit, there is "Founder-Capital Fit." Some founders thrive with infinite capital, while for others it creates a moral hazard, leading to a loss of focus and an inability to make hard choices. An investor's job is to discern which type of founder they're backing before deploying capital that could inadvertently ruin the company.
Despite having the funds, a majority of founders regret making large 'trophy' purchases right after selling. The sentiment that 'the things you own end up owning you' holds true, as these assets add new responsibilities and stress during a major life adjustment.
Many founders run "too lean," maximizing short-term profit at the expense of long-term growth. Strategically investing in a team, even if it lowers margins temporarily, frees the founder to focus on scaling, leading to greater overall profitability and less burnout.
A cautionary tale for founders who gain early liquidity. Lavish spending on items like Ferraris signals a shift in focus away from the company and customers, creating employee resentment and signaling risk to investors. It's a form of "toxic wealth" that distracts from the mission.
Beyond salary, many founders use the business to cover personal expenses, effectively increasing their compensation. Founders reported expensing 50% of their rent, Wi-Fi, and gym memberships, while others leverage business credit card points for thousands in monthly cash back—value not reflected on pay stubs.
Perks like 37signals' six-week sabbaticals are not a widespread trend but a luxury afforded by their specific business model: highly profitable, stable, with no investors. This allows them to prioritize employee retention and a unique culture over the hyper-growth demanded by VCs.