After raising capital and forming multiple legal entities, the founder made the mistake of paying all bills from the parent C-Corp's account. This co-mingling of funds created a significant accounting mess, highlighting the non-negotiable need for separate finances for each entity.
Related Insights
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.
The Profit First methodology flips the traditional 'Sales - Expenses = Profit' formula. By creating separate bank accounts for profit, owner's pay, taxes, and operations, businesses ensure profitability from day one, forcing more disciplined spending as a built-in habit.
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.
Most new entrepreneurs wait for revenue before formalizing their business with an LLC or hiring an accountant. The savvier approach is to establish this legal and financial foundation from day one, even before profitability. This professionalizes the venture immediately, forces a serious mindset, and builds a solid base for future growth.
Founders can become fixated on achieving a good burn multiple, which is a theoretical measure of fundability. However, they sometimes forget the practical reality: a great burn multiple is useless if the company runs out of cash. Cash in the bank is a material construct, not a theoretical one.
Founder failure is often attributed to running out of money, but the real issue is a lack of financial awareness. They don't track cash flow closely enough to see the impending crisis. Financial discipline is as critical as product, team, and market, a lesson learned from WeWork's high-profile collapse despite raising billions.
Early founders resist basic financial or HR controls as 'big company stuff.' However, these systems prevent avoidable, costly mistakes, much like car brakes don't just slow it down but enable it to safely travel at higher speeds, as illustrated by a former CFO.
Emma Hernan, who bootstrapped her company, observed funded competitors fail by spending investor money carelessly. Her advice to funded founders is to adopt a bootstrapped mentality, treating every external dollar with the same discipline as if it were their last personal dollar to ensure prudent capital allocation.
Tax attorney Brayden Drake admits he formed his S-Corp two years too early. Inconsistent revenue made it difficult to pay himself a required salary, leaving insufficient profit distributions to generate significant tax savings. This premature move added complexity without the financial benefit.
Relying on a single bank is a major vulnerability. Maintaining accounts with at least three banks—one primary and two backups—provides critical redundancy. This strategy protects against institutional failure, account lockouts, poor customer service, and provides leverage in disputes.
