After realizing their initial idea was wrong, the founder tried to return $200K to angel investors. The investors refused, stating their investment was in the founders, not the specific idea. They insisted the team take the money and pivot, demonstrating that early-stage bets are often on people's potential to find a solution.

A venture capitalist's career security directly impacts the founder relationship. VCs with a proven track record (like Sequoia's Andrew Reed) act as supportive partners. In contrast, junior or less successful VCs often transfer pressure from their own partnerships onto the founder, creating a stressful and counterproductive dynamic.

In today's founder-centric climate, many VCs avoid confrontation to protect their reputation (NPS) within the founder network. This fear of being blacklisted leads them to abdicate their fiduciary duty to shareholders, failing to intervene even when a company's performance is dire and hard decisions are needed.

For a seed investor, the most critical downside protection isn't a legal term in a document, but the implicit guarantee that the founder will never quit. This psychological commitment is the ultimate, unwritten liquidation preference.

Don't default to a 50/50 split on day one. Instead, agree to formally discuss equity only after reaching a predefined milestone, like $10,000 in revenue. This allows you to base the split on demonstrated contribution and commitment, avoiding the resentment from premature, misaligned agreements.

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.

Founders are warned against being manipulated by late-stage investors who pressure them to strip rights (like pro-rata) from early backers. This disloyalty breaks trust and signals to new investors that the founder can also be manipulated, setting a dangerous precedent for future governance.

The founder's partnership allowed him to build a company without shouldering the initial financial risk. This "halfsies on risk" structure meant he never had true control or ownership, ultimately capping his upside and leaving him with nothing. To get the full reward, you must take the full risk.

A frequent conflict arises between cautious VCs who advise raising excess capital and optimistic founders who underestimate their needs. This misalignment often leads to companies running out of money, a preventable failure mode that veteran VCs have seen repeat for decades, especially when capital is tight.