Canyon Coffee's founder advocates a strict financial principle: salaries must be funded by revenue, not loans or investment. New hires are "earned" when business growth can support them, often starting fractionally, to ensure sustainable team expansion and avoid excessive cash burn.

For a bootstrapped company needing inventory financing, the terms offered by platforms like Shopify Capital can serve as a credible, market-validated starting point for negotiating with friends and family investors. This provides clear, data-driven structure for an otherwise informal fundraising process.

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.

The best time to raise money is when your company doesn't desperately need it. Approaching investors from a position of strength gives you leverage. If you wait until you're desperate, you will be forced to accept expensive, highly dilutive capital.

CoreWeave’s project debt is structured with a "box" system for maximum lender security. Customer payments flow into a controlled account where a waterfall automatically pays for operating expenses and lender debt (principal and interest) before CoreWeave itself receives any profit, minimizing lender risk.

For asset-heavy hard tech companies, debt is most effective not as a bridge to the next equity round, but to finance long-lived assets (e.g., machinery) that are directly tied to contracted revenue. This approach de-risks the loan and supports scalable growth without excessive equity dilution, a sharp contrast to SaaS venture debt norms.

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.

When considering debt, the most critical due diligence is not on deal terms but on the lender's character. Investigate how they have treated portfolio companies during challenging times. Partnering with a lender who will "blow you up" at the first sign of trouble is a catastrophic risk.

When asked about a hypothetical $50M (10x ARR) acquisition offer, the founder of enterprise SaaS company Spresso called it 'a bit frothy.' He provides a grounded perspective on current valuations, suggesting a multiple in the 6-7x ARR range is more realistic for his type of business.