Six CEO roles turn failure into a management playbook
Failure Is an Option: Lessons from 6 Venture-Funded CEO Roles - Mike Grossman
Mike Grossman’s account shows how leaders can respond to failed plans, board conflict, diluted focus, and capital pressure without losing strategic discipline.
- 1Leaders control decision quality, effort, and process, but must accept that outcomes remain unpredictable.
- 2Persistence becomes costly when a failing path consumes attention, destroys opportunity cost, or no longer fits the company’s strategy.
- 3Venture capital accelerates promising ideas only when spending discipline, measurable performance, and strong people keep growth aligned.
Don't miss
Grossman explains why selling a business can be the disciplined choice when legislation eliminates its model and continuing destroys opportunity cost.
The brief
Mike Grossman, author of Failure Is an Option and a six-time venture-backed CEO, traces lessons from failed IPO plans, acquisitions, pivots, and board disagreements.
His central discipline is separating controllable inputs from uncontrollable outcomes: leaders can improve decisions, effort, and process without pretending success is guaranteed.
Grossman argues that giving up can be rational when legislation destroys a business model or a troubled venture drains attention from stronger opportunities.
A failed expansion into insurance illustrates the cost of over-diversification, while a vanity billboard becomes a warning about spending freely after raising capital.
The conversation closes on a broader claim: companies are made by people and relationships, and leadership means carrying gratitude forward after the deal ends.
Books & mentions
Some links are affiliate links — PodLume may earn a commission if you buy.
Weekly email
State of the Pod, every Monday
The week's most-discussed names and stories from podcasts, with the moments behind them. Free, five minutes, unsubscribe in one click.