Chapter 1: The Dilemma of Quitting

"I feel like I can't continue with this," Serge, the CEO of a faltering startup, confided in me. "I think I might just give up."

"What do you mean?" I was taken aback. Serge's willingness to surrender was incomprehensible to me. His company wasn't at a dead end; there was a viable route forward if he chose to pursue it.

I pressed on. "Why would you consider quitting now? Victory is within your grasp!"

"I'm exhausted," Serge admitted. "I'm tired of the struggle. I just want it to end."

Hearing that tone in Serge's voice was disheartening; it echoed a mindset I loathe. If a founder isn't prepared to confront challenges head-on, they simply can't thrive as a startup CEO.

Perhaps I'm being overly critical, but that tone screamed defeat, and I have little patience for defeatists! The thought of giving up is completely alien to my perspective.

You fight until there's no fight left in you. You discover solutions. Every successful startup CEO I've known embodies this fighting spirit, facing numerous pivotal moments that test their resolve.

As it stood, Serge had just two months of funding remaining. He was in the midst of fundraising and had potential investors who were expressing interest in his venture. Investors expect you to battle on.

"You mustn't reveal your fears to your investors," my mentor Dave told me one morning over coffee. "If they see your fear, they'll panic."

I nodded, fully aware of Dave's wisdom. His experience as both a VC and a startup CEO lent credibility to his words.

"Investors can manage a lot," he continued. "They understand that mistakes will happen and plans may falter.

"But when you communicate that you can't go on or that you're afraid, that’s when they start to worry. They’re placing their trust in you. If they sense you might give up, they'll reconsider their investment." If this seems harsh, perhaps you lack the inner fortitude required to be a startup CEO.

This may sound blunt, but it's the truth. The path of a startup CEO is fraught with challenges. Like I mentioned earlier, every successful founder I've encountered has faced multiple decisive moments.

Consider "Ray," for instance. His defining moment came when he sought to finalize his second round of funding, but one of his existing investors declined to sign the term sheet.

This scenario baffled everyone involved. The terms were favorable, and the company's valuation was set to soar.

Yet, the investor was unreachable, and time was of the essence. Ray's prospective new investor grew impatient, giving Ray until midnight to secure the signature.

Ray attempted to call the investor, but his efforts were in vain. He even reached out to the investor's lawyer, who admitted he had no control over his client.

In a last-ditch effort, Ray drove to the investor's office and insisted on speaking with him. Miraculously, the investor signed the term sheet at 11:30 PM.

Today, Ray's company boasts a valuation exceeding $1 billion and annual revenues above $100 million. However, it could have easily become just another failed Series A startup had Ray chosen to walk away.

Every day counts.

Just yesterday, I had a Zoom call with "Greg," who was in a situation reminiscent of Serge's. He also faced a two-month funding deadline.

One investor after another turned him down, and his options were dwindling. However, Greg is a fighter; I had seen him persist time and again until he achieved success.

Before I could even start our discussion, Greg beamed and announced, "I've found a lifeline. I proposed to one of my existing investors that they take the round, and they agreed."

Greg had discovered a way forward.

I must admit, the odds seemed stacked against Greg's company. While I lacked a crystal ball, I felt certain he would secure funding. My confidence stemmed from Greg's history of overcoming more dire circumstances. Each time, he had fought with relentless determination.

It was disheartening to see that Serge didn’t share this tenacity. This stark contrast between Serge and Greg was evident.

Investors possess an intuitive ability to sense your determination to fight.

Serge's company had a promising concept, but he wasn't willing to dig deep. I genuinely believe that investors picked up on this, contributing to their hesitation.

When a startup is faring well, someone like Serge may appear competent, but when challenges arise, the choice of words, tone of voice, and actions of individuals like Serge reveal their true selves.

In contrast, Greg's willingness to persevere was unmistakable. It shone through his demeanor and, more importantly, his actions.

For instance, it took Greg a considerable amount of time to reach product-market fit—longer than it should have. However, he never gave up. He kept pushing until he achieved that crucial milestone.

I felt disappointed for Serge. I tried to encourage him to see that he still had the potential to rescue his company, but my efforts were in vain. Serge was convinced that shutting down was his only option.

Perhaps, even if Serge had fought on, he still would have faced failure. There are no guarantees in the startup world, regardless of how hard you try. Nonetheless, if you battle until your last breath, you will never question whether you gave it your all.