How We Made Our First $1 Million

It wasn't pretty, but it worked.

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In a way, Text Request is the startup that never should have made it. We did have a lot going for us in the early days, like low costs and repeat entrepreneurs leading the charge. But we also had a lot going against us—no funding, no existing demand, based outside a tech hub, etc.

In the early days of a bootstrapped startup, those headwinds can feel nearly impossible to overcome.

And yet, somehow, we crossed the $1,000,000 annual recurring revenue mark 3.5 years after launch. That’s something only 4% of tech startups at the time ever achieved.

Not bad!

We did lots of things that, when combined, probably had a material impact—trade shows, top tier customer service, building features customers told us to, social media marketing, digital advertising once we had some money.

But in hindsight there were really 3 things that took us from $0 to $1 million:

  • Finding product market fit

  • Cold calling and outbound email

  • Inbound marketing via SEO

Here’s the story.

1. Finding Product Market Fit

Text Request launched as an inbound customer service tool for hospitality. The idea was that guests would be able to text a hotel concierge for room service, or a restaurant hostess for reservations.

The problem is those buyers didn’t care about it.


Then we tried college admissions departments. They loved it for reaching applicants and getting them to complete all their paperwork, but the budget approval process took a literal eternity and we needed revenue fast.

We tried other industries and eventually found a few plumbers and moving companies who had the same problem:

All their leads came in during the evening and weekends. When the business opened back up at 8am and tried to call, no one answered. They lost the lead.

But if the company texted those leads, they got a quick response and booked the service. That meant businesses could directly make more money by texting leads for sales and scheduling services.


We tailored Text Request to that use case and looked for more businesses with the same problem. Thank heavens for franchises.

Franchise owners are individual business owners, but every owner in the same brand goes through the same struggles and usually has the same processes.

And they all talk.

If we could get in with one home service franchise owner and prove our value, then we could get in with multiple in the same brand. So that’s what we did.

2. Cold Calling and Outbound Email

It’s usually the boring, unsexy stuff that works really well.

Franchise brands all have to submit a Franchise Disclosure Document that lists every location, owner, and phone number (and other details we didn’t care about). You can get these for cheap—I think we paid less than $100/yr for unlimited lists.

We picked an industry like cleaning services, chose a few franchise brands in that industry, got their details, and started calling.

It was a grind, but it worked well enough for us to get demos booked, then sales, then referrals. We weren’t swimming in cash—most of our sales were for $25/mo—but it was enough to keep the lights on.

Then our sales team left.

Our CEO/co-founder became our only sales person, and we started emailing first instead of calling just so we could reach enough people to matter.

Except email addresses weren’t included in the FDD.

So we’d pick an industry, then a state, run a Google search for “[Industry] services in [City, State],” and go through each website on the first 20 pages or so of search results.

We’d use a tool like to pull known email addresses from that website, and repeat the process for every industry we served (a growing list), in every city with more than 50,000 people, in all 50 states.

Then we’d send emails like:

Subject: Text from your business phone number

Hi First Name, did you know you can text customers from your business phone number with Text Request? You can use that to follow up with leads, schedule more appointments, and increase sales while opening up more time for you and employees to do other work.

Do you want to see how it works? Just grab a time for a short demo, or let me know what questions you have.

- Signature

Maybe 1 in 200 people booked a demo. Not efficient, but it was effective. And cheap.

Once we knew how to scale it, we went to Fiverr, found people to create lists for us, and then we’d send the emails.

3. Inbound Marketing via SEO

The market was non-existent when we launched—no one was searching for business texting. Us and a few other players changed that, but it took time.

It was 6 months in before we started blogging, and those first posts were poorly disguised sales pitches with bad writing (I was the writer).

I’d publish them to our website, post them across social media and any bookmarking site or relevant forum I could find, and include them in our emails as applicable.

It took about 6 months to see anything, but traffic started growing. We even got a few demos and sales from it.

Eventually I started publishing 3 blogs a week. Texting for This, Why No One Answers Phone Calls, How Many People Text Every Day, etc. A lot of it was garbage, some of it was good, and the rate at which we were creating new pages sent positive signals to Google.

We started earning backlinks and ranking higher. A presidential campaign shared one of our articles. The FCC used another as a source in a ruling. People interested in texting their customers started finding us and booking demos on our site.

It was working!

Lots of other things had to go right—the product had to get continually better, customers needed to talk about us to other customers, our website as a whole (not just the blog) needed constant attention and improvement.

But that all happened, and one day we looked up and saw the magical number that every SaaS startup dreams about: $83,333.33 in monthly recurring revenue—$1,000,000 annually.

We’d done it.

Fun with numbers: It took us 3.5 years to go from $0 to $1m, and 3.5 months to go from $10m to $11m. Good work really does compound.

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