True understanding of a business often comes only after owning it. Taking a small (e.g., 1%) starter position can initiate the research process and shift your perspective from a casual observer to a critical owner, revealing nuances and risks not apparent from the outside.
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To maintain an owner's mindset, the speaker asked his new employer not to tell him the total number of company shares. This counterintuitive move prevented him from being demotivated by a small percentage and signaled extreme commitment, which ultimately led to his stake increasing from 0.4% to 20%.
Instead of just buying a product, buy ownership in the company that makes it. This reframes consumption as investment, turning a one-time transaction into a potential lifetime of profit. It fundamentally changes one's relationship with money and brands from passive consumer to active owner.
Act as a strategic partner, not a vendor, by analyzing a prospect's annual reports, 10Ks, and shareholder letters. Use this research to inform them about strategic risks or business issues they haven't considered, immediately differentiating you from competitors who just ask basic discovery questions.
Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.
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.
To avoid confirmation bias and make disciplined capital allocation decisions, investors should treat every follow-on opportunity in a portfolio company as if it were a brand-new deal. This involves a full 're-underwriting' process, assessing the current state and future potential without prejudice from past involvement.
Frame your initial angel investments as a sunk cost, like business school tuition. Instead of optimizing for immediate financial returns, focus on building relationships, acquiring skills, and developing a strong reputation. This long-term mindset reduces pressure and leads to better, unforeseen opportunities down the line.
When a talented partner is too risk-averse, advice alone fails. The solution is to actively co-pilot their initial risky decisions, saying, 'We're going to invest in that company.' This 'teach by showing' approach gradually builds the courage and comfort level necessary to pursue asymmetric upside independently in the future.
Granting a full co-founder 50% equity is a massive, often regrettable, early decision. A better model is to bring on a 'partner' with a smaller, vested equity stake (e.g., 10%). This provides accountability and complementary skills without sacrificing majority ownership and control.
