The Zero to $10M Newsletter

What would you guess it takes to get your first 50 paying customers when you have 50,000 email subscribers, 53K LinkedIn followers, and a decade-long reputation in your industry?

Most founders would say a few months, maybe six at most.

When I launched Groove twelve years ago, we hit the top of Hacker News, got 500 signups in 24 hours, and TechCrunch coverage actually moved the needle.

So when I started building Helply, I expected something similar.

Instead, it took me 15 months of grinding, pivoting, and unlearning everything I thought I knew about SaaS growth.

Today, I’m sharing the brutal timeline of how we actually got to 50 paying beta customers, and why the old playbook is completely dead.

Let’s walk through what really happened.

The moment reality hit a little harder than expected.

Fifteen months ago, I fired off an email to our Groove users about a new AI tool I was building.

Hundreds of responses flooded in, all saying the same thing:

“We need an AI Customer Support Agent.”

It felt like hitting oil on the first strike. The market was practically screaming for Helply.

But here’s what I learned:

Even with an existing audience of 50,000 subscribers and proven credibility in customer support, getting people to actually pay was brutal.

The channels that worked in 2013 didn’t work in 2024 (or 2025). Press doesn’t move the needle. Blog virality isn’t even a thing anymore. Product launches rarely explode overnight.

The 15-month grind that you don’t hear founders talks about.

Here’s the real timeline from idea to 50 paying customers in 2024:

• July 2023: Started 500+ customer interviews (this took over a year, not weeks - last interview was Sept 2024)
• April 17, 2024: Email validation to Groove users - hundreds wanted it
• June 15, 2024: Built our first bare-bones widget prototype
• July 2024: Turned on pricing and reality check began
• September 30, 2024: Our first accidental demo success (we forgot to remove the widget from a demo page during a client call - they loved it)
• October 1, 2024: Hit our first 5-for-5 demo streak
• October 30, 2024: Finally reached 50 paying customers

Every single customer came with sweat, follow-ups, and ridiculous persistence. No magic bullets. No viral moments. Just grinding through the messy middle where most founders give up.

The ICP pivot I had to make.

Somewhere around month 8, we realized we were chasing the wrong customers.

Our initial interviews pointed us toward small businesses, but they couldn’t afford what we were building. We had to completely pivot our ideal customer profile toward the upper end of SMB and mid-market companies with dedicated support teams.

That meant throwing out months of positioning work and starting over.

But it’s also what unlocked everything that followed. Sometimes you have to kill your assumptions to find your market.

The “unscalable” thing that actually scaled us.

Everyone told me our VIP program was ridiculous.

We gave every new customer a private Slack channel with our team. Direct access to me, our developers, and immediate support. Most advisors called it “completely unscalable.”

They were right. It was also the best decision we ever made.

Those Slack conversations helped us build trust, guarantee results, and get much needed case studies.

We started with maybe 10 VIP customers, grew to 75 over time, and when we turned on pricing, we kept the ones who were serious and let the tire-kickers go.

It’s why people now rave about Helply. We’ll keep doing it forever because it works.

What I had to completely unlearn.

Building SaaS in 2025 is nothing like it was in 2013.

The market is crowded. AI has changed the pace. Competition is everywhere.

But here’s what hasn’t changed:

It still takes time, grit, and consistency.

As Paul Graham said:

“If you can get 10 customers, you can get 100. If you can get 100, you can get 500.”

That’s the mindset I had to relearn. There’s no rocket ship. Just doing the hard, boring, unscalable work - one customer at a time.

The real learning happens after people start using your product, when you see what works, what breaks, and what truly adds value.

Why this actually gives me more confidence.

If I could go back to day one, I’d tell myself:

“It’s going to be harder than you imagine, but more rewarding than you expect.”

We’re about to launch Helply and InstantDocs publicly in the next 30-60 days.

And while we already have 50 customers, it still feels like day one. Because in SaaS, it kind of always is.

But now I know the playbook that actually works in 2024:

Keep building.

Keep showing up.

Keep doing what doesn’t scale - until it does.

Until next time,

Alex Turnbull

Founder of OptimizeCX, the company behind

Helply, InstantDocs, Groove, and Zero to $10M