How I Got the First Paying Customers for My Startup in 10 Days

7 min readDec 22, 2014

I launched HelpFlow on Saturday December 6th. I revamped a few things in the first few days, so the “official” launch would probably be considered Tuesday December 9th.

By the following Friday December 19th, I had my first 3 paying customers. For a young startup, that’s a solid small win quickly.

Here’s how it happened.

(This post first appeared on HelpFlow.net)

At First, Keep the Business SIMPLE

HelpFlow provides a website chat service for businesses. At the core, businesses get value by having us be available to their website visitors as they browse the website to answer their questions.

There’s more to the business than that, but that’s the core value.

At launch, validate by providing the core value to customers — even if it’s not in a scalable way. (Tweet This)

Here’s what I did not do before launching:

I didn’t consider how I would get a team to manage website chat systems. I knew it could be done, because even I was somewhat new to it and it was working. But I also knew that getting a team member to do the chats was step #3 or #4, not step #1. Step #1 was to get a basic service designed (i.e. thought through enough in my head to explain it to a customer and execute it) and Step #2 was to get a paying customer. I was going to manage the chats myself for now.
I didn’t worry too much about the look and feel of the website. The first website was through Weebly, and something I hacked together in just 2 hours. After sleeping on it, I decided to rebuild in WordPress because (1) it looks so much better (2) and it sets the foundation for all the marketing I wanted to do later (i.e. Weebly would have to be turned into WordPress soon anyway, so I should have done it right off the bat).

Here’s the first version of the site, via Weebly day 1

I didn’t stress about pricing or profitability. In short, I wanted to have the price as close to $97/mo since that felt like a no brainer for businesses to try. Competitors were closer to $700/mo, which felt crazy for the customers I was targeting and for the way I wanted to sell this — (i.e. sell like a SaaS business, not a consulting / marketing services business with presentations and pitches).

I’ll do another post about how I came to our profitable pricing model, as it’s important to focus on that at some point — but it shouldn’t be the first step you do. Let paying customers help you figure out pricing (Thanks Alex!).

At this point, I had a nice but basic website, an idea of how I’d do the chat for customers, and an idea of the basic price point.

Leverage Relationships

One of the first things I did was email 2 past clients that I thought this would be perfect for:

The wedding photo booth company from my wedding in 2012, who I also did some marketing for at the time
And an e-commerce company in the machining / manufacturing business, who I did web design work for in 2007.

It would have been smarter to call these guys directly, but I was itching to make progress and it was late at night, so I sent an introduction email instead. I was also probably nervous to just cold call them out of the blue, but more on that below.

You’ll see later that they were interested, but funny enough, they didn’t pick up the phone first thing in the morning and call me to buy the service the next day. “WOW!”, right?

I was excited about the service, but of course people aren’t going to move as quickly as my excitement does.

Hustle HARD for the First Customers

I hustled hard for both paying customers, but the photo booth company is probably a good example to share.

I followed up with the photo booth company:

I sent another email 2 days later (again, I should have just called the first time)
He came onto the website and chatted with me through our website chat system
We got on a phone call and talked about using it for his website (some validation of website chat as a service by the way, since the conversation started on the website chat)

This is where the “do things that don’t scale”, “hustle”, “grind”, and every other cliche startup term shows up:

He liked the idea and though it could work well for their site
He thought the pricing was fair
And he wanted to check it out, but needed to talk to his wife / business partner first

That’s all a good sign, right?

Maybe — or maybe he didn’t quite see the value and didn’t want to say “no”.

If someone says “Sounds great, I need to think about it”, that might mean “I’m not interested…” (Tweet This)

Prove It — Do Whatever You Need to Do

I wanted to prove the value to him, and keep him moving forward toward becoming a paying customer.

I offered to run it on his website now, at no cost, so that he can see it in action while sharing with his wife. Then, he could signup for a paid account after talking with his wife about it
We literally powered up a Go To Meeting and I got the code added to his website right there.

He had his first lead come through that evening, and another one the next day.

When It Works, Push for the Payment

I agree with others in startupland that recommend getting someone to pay up front before starting the service for them, as a vote with money is really the only true vote. But doing a no cost trial just felt like the right thing to do on the first call with this customer and it ended up working out.

Once we proved the concept, I had to followup a few times with calls and emails to turn them into a paying customer (they’re pretty busy with running the business, taking care of their young kids, etc.), but he signed up for a paying account.

Lesson: “Do things that don’t scale”, as Paul Graham would say.

I would rephrase this a bit to be a bit for this stage of the company — “Do whatever it takes to get your first paying customer even if it eats the profit of the first 3 months to get them on board — this will prove people will pay for your service”.

We’re at $341/month Business — Yay?

I come from a service based business background, where the norm is $3,000-$5,000 per month clients that are pretty darn profitable.

At this point, I had 3 paying customers totaling $341/mo, but $341/month probably isn’t that exciting from a raw dollars perspective, right?

But in just 1 week, I proved a few things to myself:

There’s value in this service (i.e. it was producing leads for the paying customers and for the websites I was trailing it on at no cost to get data)
Businesses are willing to pay for it (i.e. even though I had a relationship with these customers, the photo booth in particular was a pretty good sample customer since my relationship wasn’t that deep, we hadn’t talked in years, and they are a pretty small business — the relationship just got me into the first conversation, it didn’t get me the money).
And I knew that I had a model that could scale pretty well and profitability, as I’d taken some time to run real numbers now that I had real data re: the efforts needed to do chats for customers (full post coming soon).

What’s Next?

As of writing this post, I have 3 paying customers at $341/month in total revenue which is an annual run rate of $4,092/ year. That isn’t much to write home about, but the absolute revenue figures don’t matter yet. The trends and initial insights do.

Next, I’m focused on:

Getting a rough process together of how I’m managing the chats so that I can understand how I’ll offload that to a team member after the holidays (this week is Christmas). I’m not going to get ahead of myself and staff up and focus too much on operations, but I do need to start thinking ahead for this so it’s a seamless transition for customers as we get more.
Cold emailing websites that could use the website chat system. I have a pretty advanced way that I built this prospect list, which I may share on a future blog post. I have a target of emailing 50 of them this week, and I’m at 42 as of now.
Responding to journalist for PR opportunities. This is one of a few efforts I’m using to get initial exposure, which may or may not work out well. I’ll do a post about it once I have a bit more data.
Finish segmenting my marketing agency / personal email lists to share the project with contacts that could use the service and others that I want to make aware of it so they can share with their network (i.e. other web marketing consultants in my network, etc.).

Follow Along on the Startup Adventure

If you’re reading this post, comment below. I’m putting these posts out there as a personal journal of the adventure and a way to share lessons and failures with you that you may be able to use this in launching your own projects.

Let me know what I can add to future posts to leave you feeling like “holy sh*t, that was an awesome post”.

You can follow along on Medium or through the Help Flow Startup Blog.