Issue #44: Life in Startup Land

Bean bags.

Kombucha.

Cold brew on tap.

Ping pong tables.

A kegerator with an IPA.

In-office yoga instructors.

Patagonia vests with our logo.

All the things you would expect at a startup. We’ve got none of those things. Well, actually, there might be kombucha at the Industrious we use in Chicago, and I really wish we had cold brew on tap, but we don’t have any of that other stuff.

There are two questions I get asked consistently when interviewing candidates to join Cargado. I answered the first one last week (Forager vs Cargado), and the other topic that comes up is, what’s our culture like?

I interpret that question to actually be this one: what’s it like to work at a startup like Cargado?

Here’s the honest answer: it’s challenging, exciting, sometimes chaotic, and always rewarding. It’s not about bean bags and kombucha (though I wouldn’t mind the cold brew). It’s about the people, the mission, and the work we’re doing together to build something that matters.

At Cargado, culture isn’t defined by perks or a shiny office space. It’s shaped by our values, the way we solve problems, and how we treat each other. Here’s what it’s like to work here:

1. Ownership Over Everything

When you’re part of a startup, you own your work. There’s no waiting around for someone else to hand you a perfectly tied bow. If something’s broken, you’re the person fixing it. If there’s a better way to get something done, you’re the one building it. At Cargado, “not my job” isn’t part of the vocabulary (though “not enough coffee” might be).

Think of it like being a Swiss Army knife – you might have been hired for the corkscrew, but one day you’re also the screwdriver and scissors. It’s not always glamorous, but it’s what makes building a startup exciting and rewarding.

2. A Relentless Focus on the Customer

Everything we do ties back to the people who pay the bills: our customers. They’re the reason we get up in the morning and sometimes stay up late at night. We’re solving a single, high-impact problem for logistics companies, and we take that responsibility seriously.

That’s why we don’t just slap features together and call it innovation. We listen. We test. We improve. And when a customer says, “Wow, this made my life easier,” we high-five (virtually or in person, depending on proximity). Because at the end of the day, it’s not about how fancy our code is or how slick the UI looks—it’s about delivering real results.

Pro tip: we don’t just ship software; we help people ship freight successfully! (Okay, that was cheesy, but it works, right?)

3. A Team That’s in It Together

Startups are not for lone wolves or glory seekers. At Cargado, we’re more of a pack – an incredibly talented, complementary, and highly motivated pack. When one of us stumbles, the rest of us help them get back up. And when one of us wins, we all celebrate like we just won the freight tech World Series.

Yes, there are moments when the pressure’s on, and things feel overwhelming. But knowing your team has your back makes it easier to handle. Plus, someone’s always got a dad joke or random trivia fact ready to lighten the mood. For instance: Did you know kombucha was invented in 221 BC? Neither did we. And now it’s in our shared fridge at Industrious. Progress.

4. A Chance to Make an Impact

At a big company, you’re often a cog in the machine. At a startup, you are the machine – or at least a crucial part of it. Here, you’re not just doing a job; you’re helping shape the company. The work you do today might be the reason we scale to the next level tomorrow.

It’s a front-row seat to the action. And yes, sometimes it feels like being on a roller coaster in the dark – you’re not totally sure what’s coming next, but you know it’s going to be thrilling. The best part? You’re not just along for the ride; you’re building the track.

5. A Lot of Learning (and Unlearning)

If you think you’ve got it all figured out, a startup will prove you wrong faster than a bad presentation riddled with transitions at an investor meeting. At Cargado, learning isn’t just encouraged—it’s required. Whether it’s mastering new tools, rethinking old habits, or figuring out why the printer is suddenly in Spanish, there’s always something to learn.

We don’t expect perfection, but we do expect growth. And that’s not just for new hires. I’m a second-time founder, and I’m still learning every day. Success isn’t about knowing everything – it’s about having the humility to admit when you don’t. (Though knowing where to find cold brew helps too.)

So, what’s it like to work at Cargado? It’s hard work, but it’s meaningful work. It’s fast-paced, but it’s built on a foundation of trust, collaboration, and a shared sense of humor. We don’t have Patagonia vests with our logo, but we’re tackling really challenging and rewarding problems.

If that sounds like your kind of culture, maybe you should join us. We’re hiring – and we promise no kombucha brewing skills are required.

P.S.: A few bits of advice around applying & interviewing:

• Read the job description and requirements! We are extremely picky about what’s needed to perform in these roles. If you don’t have the experience, it likely won’t be a fit.

• Constant DMs on LinkedIn don’t work well, I get blown up. Nail your application and you will get a shot!

• Typos are brutal - don’t make them. Triple check your work. If grammar isn’t your strong suit, get Grammarly. Invest in improving your written grammar. And don’t leave spaces between the last word and the punctuation mark! (it shouldn’t look like this ! 🤮)

• Show up on time (if not early) to your interviews and don’t talk the entire time. My dad used to give me this really simple advice for sales calls that I think translates to interviews: shut up and listen.

Apply here if you’re interested! Cargado Job Board