Why The Person I Was Couldn’t Build the Company I Wanted

Announcement

Our October 1.1 cohort is now open.

If you’re a venture-backed SaaS founder looking to validate your MVP, or you’re already seeing early traction, this sprint helps you know if you’re truly ready to flesh out a repeatable GTM.

We’ll pressure-test your product in front of the right buyers, run repeatable sales motions, and capture the feedback you need to refine your positioning, roadmap, and playbook.

This is hands-on execution: live reps, proven processes, and real market signals, not theory.

If you’re ready to know with confidence whether your MVP will land, book a call, and I’ll walk you through how we turn early wins into repeatable revenue.

Title: Why The Person I Was Couldn’t Build the Company I Wanted

Read time: 3 min

Today I want to share what helped me break through to the next level in my career, and what I’ve seen unlock growth for other founders too.

When I stepped into entrepreneurship, I thought I had a head start. I had a solid career behind me. I’d earned the titles, the recognition, the compensation. I felt confident. I was the GSD (get shit done) guy.

But candidly, so much of my confidence was still rooted in how other people saw me. I didn’t realize how tightly I’d tied my self-worth to those external markers.

I’ve always had a chip on my shoulder. I’ve always wanted to win. And when you find something that works, it’s easy to convince yourself that the same playbook will work again, but entrepreneurship doesn’t work like that. It humbles you, and if you let it, it will crush you.

It’s forced me to confront the parts of myself I’ve been avoiding. The doubt, the fear, the need to be seen a certain way. It exposed all of my blind spots. And it won’t stop pushing until you let go of the identity that’s no longer serving you.

I didn’t see that at first. I thought I could just outwork the challenges, prove myself again, and get the same outcome, but for me I was still carrying baggage from the old game, and trying to win a new one.

Eventually, I realized: what got me here, wasn’t going to get me there. The path ahead required different muscles. It required a deeper level of honesty with myself. It required me to stop hiding behind the old story, and start writing a new one.

Being a founder means stepping into the fire again and again, and you either let that fire burn away the ego, the insecurity, the fear… or you let it burn you out.

For me, that meant letting go of the identity I had worked so hard to build.

Every day being an Entrepreneur feels like you’re either going to win the world, or lose everything.

~Parker Conrad



I didn’t come from a world of privilege. I wasn’t surrounded by tech pedigree or investors on speed dial. I didn’t have the Stanford network. I didn’t wear Allbirds or Patagonia vests to meetings. I didn’t feel like I belonged in the rooms I was trying to get into.

For me, imposter syndrome didn’t whisper, it screamed. Every meeting, every pitch, every call carried this undercurrent of fear, that maybe I wasn’t enough. That maybe I wasn’t the real deal. That sooner or later, someone would see through me.

And it wasn’t just business pressure. It was personal too.

I felt the weight of wanting to prove myself to my family. To not let down the people who believed in me. To provide for my kids, to make my wife proud, to not be seen as the guy who left a good career and blew it chasing a dream.

None of that pressure was going to build my company for me. I had to learn to channel it. The real shift didn’t come from getting a win.

It came from making a decision. I was going to build this thing even if no one clapped for me, and oftentimes they won’t, they’ll pretend to.

Even if I had to eat shit for two years. If I had to become someone I hadn’t met yet, (and you will), I was all in.

Once a made a total commitment to put all my chips in, things started to change.

I got quiet, I really just disappeared. I stopped trying to impress. I started listening. I started studying. I stopped chasing tactics and started mastering fundamentals.

Especially in sales. Sales is the great equalizer. You don’t need a resume or a fancy degree to sell. You just need to care more, prepare more, and listen better.

Sales taught me how to hold space. How to ask better questions. How to find the real pain beneath the surface and connect with people like a human. That’s where I got my edge. Not from being the most technical, but from being the most human. Actually caring and genuinely wanting to help people.

Clients ask me all the time, “What’s the one thing I should master first?”

Sales. Every time.

Sales isn’t just about revenue. It’s about learning, and proving you can walk into the chaos and turn it into clarity. It’s about trusting your voice when you pitch a room full of people with more experience, more money, and more power than you.

It’s about believing that you know the customer’s pain better than they do, and helping them feel understood in a way no one else has. That’s what moves markets.

From my own experience, none of it happens if you’re still wrapped up in trying to protect an identity that’s already expired.

I had to learn to kill that version of me. The version that needed to be liked, that used fancy words to sound smart, that chased praise instead of progress.

I replaced it with something simpler:

Show up. Stay present. Deliver value.

I built new habits. I changed who I spent time with. I stopped trying to be the loudest in the room and became the one who actually listened. I found my confidence again, but this time it wasn’t built on titles or past roles. It was built on reps. Resilience. On staying in the game long enough to earn the truth.

If you’re feeling the friction. You’re trying to grow, but the weight of your old self is holding you back.

Let it go. You don’t need to have all the answers. You don’t need to be the most polished or pedigreed. You just need to show up real. Get your hands dirty, and keep going when it’s hard.

That’s the real game. That’s what separates founders who build movements from those who burn out.

It’s not about being impressive. It’s about being undeniable. 💪

See you all next week!

Darren

P.S. If you’re a venture-backed company interested in coaching, book a call here.