The Founder Warning Signs You Can’t Ignore: Lessons from the Trenches

This year, 2024, has been a whirlwind of pitch meetings, conferences, and countless interactions with founders, some inspiring—and others, let’s just say, memorable for all the wrong reasons. Throughout these conversations, a few behaviors have consistently stood out as deal-breakers to me. These aren’t just quirks or personality clashes—they’re giant red flags that signal deeper issues about character, capability, and, ultimately, the long-term viability of a business.

Let me walk you through some of the most striking examples I’ve encountered this year. Along the way, I’ll unpack the bigger issues they represent, and why they should matter to investors, co-founders, and anyone trying to build something that lasts.

The Passion Problem: Building for the Wrong Reasons

Passion is the engine of every great founder. It’s what gets you through the sleepless nights, the endless pitches, and the inevitable failures. But what happens when a founder is in it for the wrong reasons?

This year, I’ve met far too many founders chasing the title for ego, clout, or worse—a stepping stone to something they actually care about later. I’m talking about people who see their current startup as a placeholder—a way to gain recognition or secure funding so they can someday “pursue their real passion.”

Here’s the thing: if you’re not genuinely invested in solving the problem your business is addressing, it shows. Investors can sense it. Your team can sense it. Your customers can sense it. And when things inevitably get hard, you won’t have the fuel to push through.

I recently sat down with a founder who spent the entire pitch talking about his “future plans.” When I pressed him about his current company, he shrugged and said, “This is just a means to an end.” That was the end of the meeting.

Passion is the foundation of resilience. If you’re not excited about what you’re building now, why should anyone else be?

Flirtation in the Workplace: When Charm Becomes a Liability

Let’s talk about flirtation—a surprisingly frequent and increasingly frustrating behavior I’ve encountered this year. And no, it’s not just limited to men.

Some founders seem to think charm and flirtation are legitimate tools for networking and deal-making. Some can only sell to the opposite gender, using attraction as a substitute for competence. Others flirt their way into a connection only to fizzle out when substance is required to sustain it.

At TechCrunch this year, I found myself in a particularly bizarre situation. A man approached me and opened with, “Are you looking for your husband?” Without hesitation, I replied, “No, I’m looking for my next founder to interrogate.” I hoped that would shut him down, but he doubled down, suggesting I accompany him to a booth because “they’ll take you seriously with me on your arm.”

Moments like this are why I’ve perfected the art of the deadpan glare. He stumbled over an apology, and I walked away. But later, as I was weaving through the conference, he grabbed my hand. Yes, grabbed my hand—like he was about to kiss it.

I pulled my hand back, clenched my fist, and jabbed the air between us. His face went pale. Smiling sweetly, I said, “Fist bump, honey.” He nervously bumped my fist, and I added, “Now you have a great day,” before walking off.

Here’s the bottom line: professionalism matters. If your “networking strategy” involves unhinged flirtation, you’re undermining yourself and your business. Investors and partners won’t take you seriously, and neither will I.

Infidelity and Personal Chaos: A Breach of Trust

This is where things get messy. I’ve always maintained that I won’t do business with someone who cheats on their spouse. For me, it’s simple: if you’re willing to betray the person you’ve committed your life to, why wouldn’t you cheat on your co-founders, investors, or team?

It’s not just about morality—it’s about trust. Cheating is a behavior rooted in deception, and that deception doesn’t stay confined to personal relationships. I’ve seen founders whose chaotic personal lives bleed into their businesses, creating instability that derails everything. Affairs turn into workplace drama. Drama turns into bad decisions. And eventually, the business collapses under the weight of it all.

For investors, this is a conversation worth having upfront. I’ve even seen contracts that include “divorce clauses,” protecting the company from the fallout of personal scandals. It might sound extreme, but in a high-stakes world, trust is everything.

The Allure of Shortcuts: Cutting Corners Over Commitment

Another behavior I’ve noticed is an over-reliance on shortcuts—founders looking for the fastest, easiest way to scale, without putting in the foundational work. Whether it’s cutting corners in product development, relying on superficial connections, or launching with a half-baked idea, these shortcuts almost always backfire.

I once met a founder who bragged about outsourcing their entire product development to the cheapest agency they could find. When I asked about quality control, they waved it off, saying, “We’ll fix it after launch.” Spoiler alert: their launch was a disaster.

Shortcuts might save time in the moment, but they cost credibility, trust, and long-term success.

The Takeaway: Why These Behaviors Matter

Passionless founders lack the drive to persevere. Flirtatious founders undermine their credibility. Cheating founders compromise trust, and shortcutting founders cut corners on quality. These aren’t just bad habits—they’re symptoms of deeper issues that can sink a company.

As an investor or partner, you need to pay attention to these behaviors. They’re not just personal flaws; they’re professional liabilities. And as a founder, if any of this feels uncomfortably familiar, it’s time to take a hard look at your priorities.

At the end of the day, startups rise and fall on the shoulders of the people running them. And if those people can’t lead with integrity, professionalism, and passion, no amount of funding or strategy will save them.

Let’s raise the bar.