Let’s Talk About Failure, Shall We?

(The Kind That Makes You Want to Crawl Under a Rock) Failure gets romanticized a lot. People say things like, “Fail fast! Failure is just feedback!” And sure, that sounds great on a t-shirt or a LinkedIn post. But when you’re the one who just heard “no” (again) from a lender, an investor, or a […]

Business GrowthMay 13, 2025By Intrepid Finance Team
Alex Perry with Practically Speaking

(The Kind That Makes You Want to Crawl Under a Rock)

Failure gets romanticized a lot. People say things like, “Fail fast! Failure is just feedback!” And sure, that sounds great on a t-shirt or a LinkedIn post. But when you’re the one who just heard “no” (again) from a lender, an investor, or a pitch panel, you don’t want a bumper sticker. You want a nap, a donut, and maybe someone to remind you you’re not crazy for trying.

Here’s the truth: Failure can make you stronger—but only if you don’t shove it down or pretend it didn’t hurt. You’ve got to feel it, name it, and then ask: “What’s this teaching me?” (Not in a toxic-positivity way, but in a ‘How do I not step in that same pothole again?’ way.)

Let me put it this way:
Failure is like getting stuck in the mud wearing your cutest shoes. You’re standing there, knee-deep, mad at the puddle, mad at the shoes, mad at yourself for thinking this path might be the one. But if you slow down long enough to look around, you’ll notice two things:

  1. You’re not the only one who’s been through this mess. There are many Louis Boutins left scattered on the path to success. 
  2. The road doesn’t end here, but you may need new shoes and a better map.

Chances are, you’re a person who constantly has to prove your worth and work twice as hard for half the access. That means it’s not just about failing well. It’s about navigating systems that weren’t built for you in the first place. Which means that sometimes, you put on your boots, jump over the muddy puddles, and learn to thrive in a system that wasn’t built for you.

Your ability to do so isn’t just resilience, it’s your superpower. 

So here’s what I want you to remember:

  • Failing doesn’t mean you’re failing forever. It means you’re in process.
  • You don’t have to bounce back alone. Find your people (hi, I’m one of them).
  • And when someone else trips and falls? Don’t offer a pep talk—offer your presence.

This journey is hard. But you’re not crazy for dreaming big. You’re not wrong for trying again. And you are absolutely not alone.

I’m cheering for you always—through the wins, the rejections, and the why-is-this-so-dang-hard moments.

Your Front Row Fan, Alex 

Related Blogs

12 Fundraising Myths That Are Quietly Costing Pre-Series A Founders Their Raise, a joint resource from Intrepid and RevTech Labs
05 min readOctober 6, 2026

12 Fundraising Myths That Are Quietly Costing Pre-Series A Founders Their Raise

A joint resource from Intrepid and RevTech Labs By Steve Iskander, Intrepid, and Dan Roselli, RevTech Labs Founders don’t usually lose out on funding because their business is weak. More often, it’s because they believed something false, waited too long, over-explained the wrong thing, or walked into a pitch unprepared for a question they should […]

Read More
A layered foundation of structured glowing data blocks, headline 'The moat is the pipeline' - lending data infrastructure as the durable moat.
05 min readSeptember 15, 2026

The Underwriting Moat: Why Data Infrastructure, Not Model Choice, Decides the Next Decade of Private Credit

By Steve Iskander, Founder and CEO, Intrepid In this article Why the model cannot be the moat The four properties of a defensible data layer Compounding is the whole point What this means in practice I have spent six weeks making one argument about lending data infrastructure from six directions. Here it is in one […]

Read More
A data pipeline moving from a slow tangle into a bright green fast lane, headline 'Speed is a data problem' - improving loan underwriting speed.
05 min readSeptember 1, 2026

Faster Underwriting Is a Pipeline Decision, Not a Headcount Decision

By Steve Iskander, Founder and CEO, Intrepid In this article Two clocks, one gap Why hiring scales the wrong thing The measurement that changes the conversation Where to start Every lender I talk to who wants better loan underwriting speed starts in the same place. We need to hire. I understand the instinct. I ran […]

Read More

Start Growing Today

Faster underwriting. Smarter matching. Cleaner deal flow. Built for the way capital actually moves.