A massive purchase order from Trader Joe's created a $1M funding gap. Instead of selling equity at an early stage, the founders secured debt from friends and family, backed by the PO and personal guarantees. This preserved their ownership while fueling a pivotal 10x growth moment.

Counter to the 2021 venture climate of growth-at-all-costs, Sure operated with a private equity-like discipline. They raised a $100M Series C when they were already profitable and hadn't spent any of their Series B funds. This capital efficiency provided the freedom to control their own destiny and make long-term decisions.

To maintain product focus and avoid the 'raising money game,' the founders of Cues established a separate trading company. They used the profits from this successful venture to self-fund their AI startup, enabling them to build patiently without being beholden to VC timelines or expectations.

Flipsnack proves the model of using founder-owned profits to reach significant scale. Only after hitting $15M ARR did they take on non-dilutive debt capital for targeted acceleration, like opening international sales offices. This avoids early dilution and maintains 100% ownership while fueling growth.

Venture capital can create a "treadmill" of raising rounds based on specific metrics, not building a sustainable business. Avoiding VC funding allowed Donald Spann to maintain control, focus on long-term viability, and build a company he could sustain without external pressures or risks.

The use of SAFEs has expanded beyond pre-seed, becoming the dominant instrument for rounds up to $4M that were historically priced. This trend simplifies closing a round but creates significant downstream complexity when calculating ownership for employee stock option grants and future rounds.

Reflecting on raising $35M, Ergatta's founder suggests taking less capital might have been wiser. While tempting to raise as much as possible, large funding rounds lock the company into a specific financial trajectory and set of expectations. Raising less money can preserve crucial optionality and flexibility for the business's future.

For founders unable to get traditional loans, a viable alternative is offering high-interest (e.g., 15%) subordinated debt to angel investors. The best source for these investors can be existing, passionate B2B customers who believe in the product and want to be part of the success story.

To incentivize Clapp's founders, part of the deal included convertible bonds in Lemlist's parent company. This structure avoids the complex process of setting a formal valuation for Lemlist today, instead granting the founders the right to buy shares at a 20-30% discount during a future liquidity event.