Two Reasons for the Question

"For two main reasons," he explained. "First, by the time I ask something like 'When was the last time you took a vacation?', it typically indicates that the entrepreneurs have effectively articulated their business ideas. It suggests that I don't need to probe into growth metrics or customer acquisition strategies because those aspects are already clear."

"That makes sense," I agreed. "You're not dismissing those topics; you simply prefer not to revisit them."

"Exactly," he affirmed. "It shows that I'm engaging with entrepreneurs who have a solid grasp of what to highlight in their pitches—an encouraging sign for potential investment."

"But how does your vacation question provide additional insight?" I inquired.

"That's the second reason it intrigues me," he continued. "Inquiring about their vacation habits reveals a lot about the type of entrepreneur they are."

A Deeper Dive into Entrepreneurial Mindsets

A student interjected, "Are you assessing their dedication to their work?"

"Not quite," he clarified. "While that might be the initial interpretation, that's not the real aim of the question. It influences the nature of the responses I receive."

"Can you elaborate?" I asked.

"Typically, there are three types of answers I encounter," he explained. "The first group proudly claims they haven't taken a vacation in years. The second group admits they haven't taken one, but they express a degree of embarrassment about it. The third group can readily recall their last vacation and describe the experience."

"Interesting," I chuckled, impressed by his thoughtful analysis. "Which response are you looking for, and why?"

"I prefer to invest in entrepreneurs who take regular breaks," he stated. "Thus, I'm pleased when someone can easily describe their recent vacation. These entrepreneurs recognize the importance of stepping away from their businesses from time to time."

Challenging the Notion of Dedication

"But why would you shy away from investing in someone who doesn't take vacations? Aren't those the most committed founders?" a student asked.

"Not necessarily," he countered. "It may sound counterintuitive, but those who can't detach themselves from their work are often at risk of burnout and narrow-minded problem-solving. Every founder needs to take a break to recharge and gain fresh perspectives. Moreover, a business must be able to function independently of its founder. Therefore, when I hear entrepreneurs boast about their lack of vacations, it raises red flags for me. They either don't grasp the necessity of distancing themselves from their companies or they're being less than honest with me."

"What about those who seem embarrassed by their lack of vacations?" I probed further.

"Those are my ideal entrepreneurs to back," he revealed. "They recognize the need for breaks but have struggled to take them. In such cases, I know my investment will help provide them with the resources to delegate responsibilities. Once I offer that support, I prioritize encouraging them to take time off. I've even funded trips for some founders to ensure they take those necessary breaks."

"Really?" I exclaimed. "I've never heard of a VC financing a vacation."

"Why not?" he replied. "An investor's role is to equip a company with the resources it requires to thrive. Given that a company's success hinges on its founders being able to step back occasionally, I see it as part of my job to facilitate that. If sponsoring a vacation for my founders means making their companies more successful, then I'm more than happy to send them to a place like Disney World for a week!"

Want to delve deeper into the world of startups and entrepreneurship? Sign up for a (FREE) mini-course with me today!