The Founder's Financial Playbook for Scaling Without "Flying Blind"

William Lieberman on Financial Frameworks, Founder Hubris, and the "One Horse" Mistake

In this "Freeing the Founder" episode, serial entrepreneur William Lieberman, founder of The CEO's Right Hand, details the financial and operational frameworks necessary for scaling a professional service firm. Drawing from a career that includes building a FinTech company from a $195/month service to a $100,000/month enterprise deal and a subsequent 10-year journey with his current firm, Lieberman outlines the critical lessons learned from both profound success and near-failure.

The conversation provides a blueprint for founders to move from "flying blind" to making data-driven, confident decisions.

Key Insights from the Conversation

1. The Core Problem: Founders Are "Flying Blind" Lieberman identifies the most common pain point for founders: a lack of financial foresight. Many leaders come to him unable to answer fundamental questions like, "Can I afford this new hire?" or "Can I sustain this new ad spend?".

He compares this to "flying a plane without the knobs and dials." Most founders have a bookkeeper, which acts as a rearview mirror (showing what happened last month), but they lack a financial forecast, which is the windshield (showing where the business is headed). The primary consequence is an inability to make effective decisions quickly, leaving the business vulnerable to market disruptions, sales slumps, or supply chain issues.

2. The Solution: The "Break the Glass" Emergency Plan To solve this, Lieberman implements a strategic framework built on scenario planning:

Forecast: First, a realistic financial forecast is created.

Scenarios: This forecast is then modeled into three scenarios: Best Case, Base Case, and Worst Case.

Guardrails: Clear "guardrails" are established. For example, the team agrees that if sales miss projections for two consecutive months or cash reserves dip below a pre-determined level, specific actions will be triggered.

The Plan: This becomes the "break the glass in case of emergency" plan. Its purpose is to remove emotion from critical decisions. When a guardrail is breached, the leadership team doesn't panic; they execute the difficult, pre-agreed-upon plan (e.g., cutting specific expenses, freezing hiring), allowing them to react with speed and decisiveness.

3. The Human Obstacle: Founder Hubris When founders resist this financial guidance, Lieberman notes the problem is rarely a lack of intelligence. The most significant impediment is hubris.

He describes the "hardheaded" founder as one who is arrogant, operating with "rose-colored glasses," or driven by a chip on their shoulder. They ignore data and tell their team, "Trust me, I got it." This is the most dangerous personality trait in a CEO.

The countermeasure is firmness and leveraging the wider team. By presenting the black-and-white data and aligning with other executives or board members, the founder is forced to confront the reality that "those companies [who ignore the data] don't exist today".

4. The Operational Parallel: The Founder Bottleneck This financial chaos is often a symptom of the "Founder Bottleneck". Lieberman, who has experienced this himself, notes that founders often fail to delegate or hire the right team because they don't trust anyone to do the job as well as they can.

The solution is to hire people who are better than the founder at a specific function (sales, finance, operations). The CEO's job is not to be the best at everything; it is to provide the vision, the resources, and then "let them go get 'em".

5. A Career-Defining Lesson: The "One Horse" Mistake Lieberman shares the most critical lesson of his career, learned during a capital raise at his first company. His advisory team convinced him to "run one horse"—to pursue a single strategic investor. The deal dragged on, and the company’s cash reserves dwindled. Lieberman was within two weeks of having to lay off half his staff before the deal finally closed.

His guiding principle ever since is to always have options. "Even having two options is better than only having one". This philosophy of building in strategic options applies to sales pipelines, financial plans, and overall business strategy, creating the resilience needed to navigate the inevitable hurdles of entrepreneurship.