The Cold Calling Billionaire: What I Learned from an HRTech Giant

Last week, I found myself sitting across from someone who carries the weight of 2100+ employees on his shoulders. Not metaphorically speaking here; this HRTech entrepreneur literally has that many people depending on him for their livelihoods. And you know what struck me most? He started exactly where I did: cold calling.

When I asked him about his path to success, his answer was refreshingly simple: "Just do the reps."

No fancy growth hacks. No secret sauce. Just picking up the phone, dialing numbers, and hearing "no" more times than most people could stomach. Sure, he admitted luck played a role (it always does), but the foundation was pure repetition. Day after day, call after call, rejection after rejection, until eventually, the yeses started stacking up.

I know exactly what those early days feel like. I remember this one call that would've broken most people. The guy didn't just reject my pitch; he went nuclear. Started cursing at me, then somehow pivoted to cursing at my mother too. I'm talking full verbal assault mode over a simple sales call. I sat there, phone pressed to my ear, absolutely shocked.

But you know what? That moment was a gift. Because after someone goes that hard at you and your family over a cold call, every other rejection feels like a gentle breeze. That guy unknowingly gave me the thick skin I needed to succeed in this game. He taught me the ultimate lesson: other people's reactions are about them, not you. Their anger, their frustration, their need to lash out? That's their problem. Your job is to hang up, dial the next number, and keep moving.

But here's where the conversation with this HRTech giant took an interesting turn. I asked him about decision making at scale, expecting some complex framework or mental model. Instead, he dropped this truth bomb: "Making decisions at the 70th hour of your work week isn't going anywhere."

Think about that for a second. Most founders I know (myself included) wear those 80 hour weeks like a badge of honor. But this guy, managing billions in enterprise value, is telling me that after 70 hours, your brain is basically running on fumes. Your judgment gets cloudy. Your decisions get sloppy. You're not being productive; you're just being present.

His solution? Balance isn't optional; it's strategic. Whether it's hitting the gym, meditating, or whatever helps you reset, these aren't luxuries you earn after success. They're the tools that make success sustainable. For me, it's BJJ classes. For him, it might be something else. The activity doesn't matter as much as the consistency.

What really resonated with me was his emphasis on mindset resilience. Building something meaningful isn't just about having the skills or the network or even the capital. It's about having the mental fortitude to keep showing up when everything feels like it's falling apart. Because it will feel that way. Multiple times.

The path from cold calling to commanding a 2100 person organization isn't linear. It's messy, exhausting, and filled with moments where giving up seems like the rational choice. But that's exactly why most people don't make it. They stop doing the reps. They burn out at hour 71. They forget to invest in their own sustainability.

Here's what I'm taking away from this conversation: Success at scale isn't about working harder than everyone else. It's about working consistently, maintaining your judgment by protecting your energy, and developing the kind of unshakeable mindset that turns "just doing the reps" into building an empire.

Whether you're on your first cold call or your thousandth, remember that even the giants started exactly where you are. The only difference? They never stopped doing the reps. And yeah, some of them probably got cursed at too. The winners just didn't care.