How to make your first sale

Nick Gatens was a photographer in Louisville, Kentucky. He'd been working on a project for a while and was getting close, or so he thought. When we talked, he told me, "I'm not sure I've got the right site design, or the right message for visitors."

I asked for the URL. He paused.

"Well, I don't actually have the site up yet."

That's where Nick was stuck. Not on the site design. Not on the code errors he kept mentioning. On fear. The technical problems were real, sure, but they weren't the actual barrier. Fear was the barrier. Everything else was a convenient excuse to avoid putting his work in front of strangers.

A few weeks later, Nick had an update. An excited one. "I got the site up, and I made a sale!" A total stranger had followed a link and paid $50 for one of his prints. Fifty bucks. From a person he'd never met.

Nick told me later: "That conversation made me think about why the site wasn't up yet. In my head, it was all technical: I had to tweak the design and fix some errors in the code. But being honest with myself, I realized my fear was still holding me back; the technical stuff was just an excuse."

This is the pattern I've seen over and over. People have something to sell. They know it's good. They spend weeks or months perfecting things that don't need perfecting, because the alternative is putting it out there and finding out whether anyone will pay for it. That's the scary part. And it's also the only part that matters.

The first $1.26 is the hardest

I know this from personal experience. I made my first $1.26 with a new project while on a layover in Brussels. Couldn't even afford a Belgian waffle on the day's take. But I had a good feeling about the future.

And that feeling turned out to be right. Growing an existing business is usually easier than starting it. "It took a while to find something that worked, but once we were rolling, we gained traction and quickly took off."

This is something I heard again and again from the people I studied for the book. Once that first sale comes in, something shifts. One person put it this way: "Once the first sale came in, I knew I'd succeed. It may not have been completely rational, but that single sale motivated me to take the business much more seriously."

That $50 print for Nick. My $1.26 in Brussels. Your first sale, whatever it turns out to be. The number almost doesn't matter. What matters is the proof that someone, somewhere, will pay you for what you've made. Everything before that moment is theoretical. Everything after it is real. If you've already got a one-page business plan and you've tested your idea, you're closer than you think.

Be a hustler, not a martyr

There's a poster by Joey Roth that I think about constantly. It shows three icons representing three types of people.

The charlatan is all talk, with nothing to back up their claims. The martyr is all action with plenty of good work, but remains unable or unwilling to promote it. The hustler is the ideal combination: work and talk fused together.

Here's another way to think about it. Style without substance is flash. Nobody respects these people. Substance without style is unknown. Everyone who knows them respects them, but not many people know them. Style with substance is impact. That's the goal.

If you build it, they might come... but you'll probably have to tell them about it.

Most people starting a business err heavily on the martyr side. They do great work. They put everything into the product, the service, the experience. And then they sit back and wait for customers to find them. That doesn't work. You need to spend roughly 50% of your time creating and 50% connecting. Half making the thing, half telling people about it.

In my own work, the "hustler" image is pretty much what I try to do every day: lots of creating and lots of connecting.

The template that actually works

So how do you tell people about what you're doing without being annoying about it? Start with this template from the book:

"Hi [name], I wanted to quickly let you know about a new project I'm working on. It's called [name of business or project], and the goal is to [main benefit]. We hope to [big goal, improvement, or idea]. Don't worry, I haven't added you to any lists and I won't be spamming you — but if you like the idea and would like to help out, here's what you can do: [Action Point #1] [Action Point #2] Thanks again for your time."

Notice what that message isn't. It isn't a hard sell. It isn't a mass email blast. It's a personal note from one person to another. You're not "selling." You're letting them know and inviting them to participate.

Here's the method. Make a list of at least fifty people. Divide them into categories: colleagues, college friends, acquaintances. As soon as the project is ready, touch base by sending a quick note. Each message is personal, even though the content is largely the same.

Fifty sounds like a lot. It isn't. Think about everyone you've worked with, gone to school with, met at events, connected with online. The most powerful channel for your first sale starts with people you already know. Not strangers. Not paid traffic. People who already trust you enough to open an email from you.

Strategic giving beats traditional marketing

Megan Hunt designs and sells dresses. Her marketing strategy? She calls it "Strategic Giving."

"When I launch a new line of dresses each year, I contact two or three influential bloggers and create a custom dress for them, which always brings in tons of new customers when they write about it. But most importantly, I turn my attention toward my clients. Often, I upgrade someone's shipping to overnight for free, or double someone's order, or include a copy of my favorite book with a handwritten note. I like to package my products for shipping like a gift to my best friend."

No ad budget. No complicated funnel. Just generosity directed at the right people, and an obsessive focus on making existing customers feel special.

Karen Starr took a different approach. She spent zero on advertising. Instead, she painted a 30-by-55-foot mural of a colorful tree on her building. "That speaks way louder than any ad."

Then there's John Morefield. He was an unemployed architect during a time when jobs were scarce. Instead of sending out resumes, he set up shop at a Seattle farmer's market with a sign: "5-cent architecture advice." For a nickel, he'd give advice on any problem. It was effectively a lead-generation program, though he probably didn't think of it that way at the time. As news spread, he got free advertising from CNN, NPR, the BBC, and numerous other media outlets. John is now a successful self-employed architect. That's a distinction worth noting. He didn't find a job at another firm. He built his own practice. (More stories like John's here.)

The $10,000 experiment

I wanted to test something. For my Travel Hacking Cartel service, I ran two campaigns side by side.

Campaign one: I spent $10,000 on carefully selected ads and sponsorships. Took about two hours to set up. Result: 78 new customers. Estimated value: $7,020.

Campaign two: I spent 10 hours hustling. Guest posts, joint ventures, reaching out to journalists. Zero dollars. Result: 84 new customers. Estimated value: $7,560.

The hustling won. More customers, more revenue, no money spent. That works out to roughly $756 per hour of hustle.

The point isn't that advertising never works. Sometimes it does. The point is that hustling can take you far, and you should think about it first and paid advertising later, if at all. Especially when you're making your first sale. You don't need a budget. You need effort, directed at the right people. If you're wondering what to do during a solo launch, start with hustle, not ads.

The one-page promotion plan

Here's a framework I put together for the book. The goal: to actively and effectively recruit new prospects without getting overwhelmed.

Daily: Maintain a social media presence. Post one to three helpful items and respond to questions. Monitor one or two metrics. No more than that. You'll drive yourself crazy checking stats all day.

Weekly: Ask for help or joint promotions from colleagues. Maintain regular communication with prospects and customers.

At least monthly: Connect with existing customers. Ask them: "Is there anything else I can do for you?" Prepare for an upcoming event, contest, or product launch.

Once in a while: Perform a business audit to find missing opportunities. Ensure you're working toward building something significant, not just treading water.

That's the whole plan. It fits on a single page. The daily tasks keep you visible. The weekly tasks keep you connected. The monthly tasks keep your customers close. And the occasional audit keeps you honest about whether you're heading somewhere worth going. (You can download this template along with other tools in the free resource library.)

Just get the site up

Back to Nick. The conversation that changed things for him wasn't about design, code, or marketing strategy. It was about honesty. He'd been telling himself a story about technical problems when the real issue was that he was afraid. Once he admitted that, he got the site up in days. And within weeks, a stranger paid him $50.

Your version of "the site isn't ready" might sound different. Maybe it's "I need to finish the course first" or "I'm still researching the market" or "I just need to tweak a few more things." Maybe some of that is true. But ask yourself what Nick asked himself: is the real reason fear?

If you've got a business idea and you've been sitting on it, the best thing you can do right now is stop perfecting and start selling. Make your list of fifty people. Send the message. Set up the system to close your first sale. The $1.26, the $50, whatever your number is. It's waiting on the other side of the fear.

Frequently asked questions

What if I don't have a website yet?

Get one up. Today. Nick Gatens spent weeks telling himself his site design wasn't right, his code had errors, the message wasn't clear. When he was honest with himself, none of that was the real problem. Fear was the problem. The technical stuff was an excuse. Put up something basic and start selling. You can fix the design later.

Should I spend money on advertising for my first sale?

Probably not. I ran a direct experiment: $10,000 on ads versus 10 hours of hustling. The hustling brought in more customers (84 vs. 78) and cost zero dollars. That's roughly $756 per hour of effort. Think about hustling first. Paid advertising can come later, if at all.

How do I promote my business without feeling sleazy?

You're not selling. You're letting people know about something you made and inviting them to participate. There's a difference. Make a list of fifty people, write each one a personal note about what you're working on, and include a clear action step. That's not spam. That's communication between humans.

How do I split my time between creating and marketing?

Fifty-fifty. Half creating, half connecting. Most people lean way too far toward one side. If you only create, you're a martyr with great work nobody knows about. If you only talk, you're a charlatan. The sweet spot is doing both, every single day.