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.

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.

While you don't need to be a parent to start a family-focused business, you must compensate for this blind spot. An investor would scrutinize a non-parent founder's early hires to ensure parents are on the team and have direct access and influence over key decisions.

When lending money to friends, Emma Hernan operates under the assumption she may not be repaid. By mentally reframing the loan as a potential gift, she avoids resentment and preserves the friendship, regardless of the financial outcome. This protects her own well-being and relationships from financial strain.

Your personal circle signed up for a relationship, not to be your customer base. Relying on them for sales or engagement is unsustainable and emotionally draining. Focus instead on finding genuine fans and customers online.

The primary goal in a family-run business should be preserving relationships, as work provides meaningful time together. Choosing money or ego over family creates tension. Often, the real friction stems from a perceived lack of respect, not just financial disagreements, which can poison the dynamic.

Entrepreneurs often believe their biggest fear is judgment from anonymous internet users. However, the real psychological barrier is the anticipated criticism or misunderstanding from their close friends and family. These are people who are unlikely to ever be customers, yet their opinions are given disproportionate weight.

The opportunity cost of working in a family business can be enormous, limiting personal financial upside. However, the time and relationship built with a parent can be the most valuable and fulfilling experience of one's life, a trade-off that transcends monetary calculation.

The right time to raise capital isn't always for aggressive growth. For Boll & Branch's founders, it was when personal financial pressure from debt became overwhelming. Raising money to de-risk their personal lives allowed them to run the business with "clear heads."