Things I Didn't Think About Before Starting a Small Business

Before starting a business, I spent all my time thinking about the fun, creative parts: coffee quality, branding, sourcing, hospitality, community, and building something meaningful.

What I didn’t think about?

Phone systems. Dumpster logistics. Shipping dimensions. Software integrations. Human emotions. And the fascinating underbelly of "Best Of" lists.

Turns out, building a small business is equal parts passion, problem-solving, therapy session, and adult scavenger hunt.

So, here are a few things I genuinely did not think about before starting out.

1. How Do I Get a Landline?

Honestly, this one completely stumped me. And if I’m being honest… it still kind of does.

Having customers call your personal cell phone is not ideal — especially if you have dreams of growth. Eventually, your phone starts feeling less like a communication tool and more like an anxiety device.

So naturally, you think: "I’ll get a business phone line!" Simple, right?

Wrong.

First, you realize you forgot to specify cordless. Suddenly, your café looks less like a modern coffee company and more like an episode of The Office. Then come the voicemail trees, routing systems, extensions, hold music, forwarding rules, and mysterious settings that nobody fully understands.

At this point, if anyone has a PhD in phone systems, please contact us immediately.

2. Which Software Systems Actually Play Nice Together?

I came from a fintech and Wall Street background, so I thought this part would be straightforward. My dream was simple: software systems that integrate beautifully so humans can spend their brain power doing creative, meaningful human things.

Instead? Chaos.

Why can’t my POS system also book tours? Why do gift cards work online but not perfectly in-store? Why does every platform almost integrate with the next but require three plugins, two workarounds, and a prayer?

Frankly, whoever figures out how to seamlessly integrate the entire small business tech stack is going to make an absurd amount of money. Until then, we continue cobbling the pieces together. But one hard rule remains: No spreadsheets. There has to be software for that.

3. Wait… How Do We Get Rid of the Trash?

When you move into a house, someone tells you what day trash pickup is. You even get a free trash can.

With a business? Congratulations. That’s now your problem.

There was a phase where we were literally making constant runs to the dump ourselves. One of our employees cried tears of joy the day we finally got big enough to justify an actual dumpster with scheduled weekly pickup.

It felt like a major business milestone. Forget revenue targets — we had achieved commercial trash infrastructure.

4. How Much Is Shipping?!

Shipping is one of those things you completely underestimate until you actually start doing it at scale. We interviewed providers, asked seasoned operators for advice, tested systems, and we are still learning the nuances constantly.

For example: Did you know a 12x8x4 inch box might cost around $23 to ship via FedEx… but if you put that exact same box into a FedEx Pak envelope, somehow it magically becomes $13? Who makes these rules?

These tiny shipping nuances matter enormously because shipping is a massive expense for growing businesses. We don’t have Amazon or Walmart negotiating rates for us behind the scenes. Every inch, ounce, and packaging decision matters.

5. Wait… "Best Of" Lists Are Bought?

Besides the landline debacle, this may have been the biggest shock to me. We set out thinking, "Let’s get our award-winning coffee featured on some ‘Best Of’ lists!" And guess what? We absolutely could… for the low, low price of a $15,000 full-page ad.

Or we’d hear: "We’d love to evaluate your company after you speak with our advertising department." Disheartening? Sure. But honestly, it made us focus even harder on earning real, organic support — Google reviews, word of mouth, and genuine customer enthusiasm.

Ironically, some international magazines were the complete opposite. They simply reached out and said: "Hey, we love your brand and coffee and want to feature you." No ad package. No sales pitch. Just pure appreciation. That meant a lot.

6. Humans

We knew from day one that our team would be our greatest asset — and also the most complicated part of the business. But the level of complexity was more than we ever imagined. Because… humans.

We made a conscious decision early on that we wanted as many full-time employees as possible, rather than building entirely around part-time labor. We wanted proper HR support, healthcare, benefits, fair wages, and real opportunities for growth. Most importantly, we wanted to build a place that genuinely felt like a great place to work.

That is complicated, always challenging, and always worth striving for.

We love our team like family. What we may not always be able to provide in terms of "big company" perks, we try to make up for in kindness, flexibility, respect, and genuine care. Of course, we’ve heard the horror stories about employees — and yes, we have a few stories ourselves — but at the end of the day, our team is amazing, and prioritizing them feels essential.

Not just because it’s the right thing to do, but because study after study shows that businesses investing in employee wellbeing see lower turnover, stronger workplace culture, and happier teams. Turns out people tend to do better work when they feel valued as human beings. Wild concept.

7. The Best Part Wasn’t Just the Coffee

This is something we knew we would love, but we didn’t realize just how much it would mean to us: The community. All the things that the business of coffee has allowed us to be part of in the communities we touch have been incredibly humbling. Through our Team Tradition program, we’ve been able to help sports teams and youth organizations fundraise for their goals and dreams. We’ve donated countless tours and tastings to organizations for auctions, raffles, and community events.

We’ve also been honored to provide coffee for military families experiencing profound loss through organizations like the Marine Reconnaissance Foundation. Honestly, many of these organizations have touched us more than we ever expected. We are constantly humbled that they asked us — little ol' us — to be part of the meaningful work they’re doing in the world. Knowing that our small business gets to contribute, even in a small way, makes it clear that it's never "just coffee."

Watching people pull up chairs in our space to laugh, talk, and connect is the ultimate reward. We realized early on that roasting coffee was just the vehicle; the real work is gathering people. Even as a tiny speck in a big world, a neighborhood business can create a massive ripple of real connection and community.