Road to 1M ARR - September Update
Monthly update: Our numbers, newsletters and enterprise sales
👋 Hi, I’m Iron from Simple Analytics, and welcome to my newsletter, The Road to 1 Million ARR. Sign up for weekly insights, growth strategies, and playbooks on how we are growing our business to 1 Million ARR. Fully transparent.
Welcome to our September update. This newsletter is called “Road to 1M ARR” (1 million dollars in yearly revenue), so every month, I provide an update on where we at. It’s a monthly review of growth numbers and stuff we did.
Most of you subscribed after reading the “How to grow your business” article. It kinda went viral. Expect more of those as well!
The goal of the monthly update is twofold. First, it helps me keep track of our progress. Second, I hope you pick up something interesting—maybe a thought, an idea, or a growth tactic we implemented.
It’s a look behind the scenes of a two-person, 35K MRR bootstrapped startup.
Stick around and let me know what you think!
So where are we now?
We’re doing around 34.5K MRR (up 5%), which translates to around 415K ARR (almost halfway to our goal!). Our numbers are automatically updated on this page.
Main growth driver this month: Adriaan fixed our pricing.
We’ve changed our pricing strategy from from subscription to pay-per-usage. However, we ran into some issues and didn’t fully implement it. This meant that some users were not charged properly for their growing traffic. This is fixed now. Hence the bump in MRR.
Growth has been slow the last couple of months. The 12-month average is 3.5%, and the goal is 5%.
If it stays at 3.5%, we’ll reach 1M ARR in November 2026.
What happened last month?
Well, not much on my end for the first two weeks. I took some time off. Went to Greece with my girlfriend. Just chilling and overeating - while Adriaan was holding the fort.
It was great. Two weeks is the perfect amount of time—I can fully disconnect, but by the end, I’m also ready to dive back into work. Greece was no different.
Newsletters
On holiday, I concluded that we should restructure our newsletter. At Simple Analytics, we run “The Privacy Newsletter” with 1500 subscribers.
We use it to communicate privacy-related news facts, sometimes a new feature or a monthly update like this. However, for the past year, it’s been lying around. No ownership and no clear structure.
Time for a change.
Instead of repurposing the old newsletter, I created two new newsletters. This one you’re reading is about our journey to 1M ARR, including monthly updates on how we grow and run our business. The other one will focus on privacy. Carlo (our giga privacy nerd) re-started “The Privacy Newsletter.”
A well-run newsletter can be a great asset for your business:
You can inform, engage, and activate your customers/subscribers
Build relationships
It forces you to write content - which can be repurposed to other socials.
There is so much AI bullshit content going around now. You need to create unique and genuinely interesting content to stand out from the crowd.
People are lazy. They’ll let AI do the work. If everyone follows that route, being different becomes more valuable and helps build your brand.
It’s also easy to write - just talk about what you’ve done for the past month.
I’d find it interesting to hear what other founders did last month to grow their businesses. (Please actually let me know if you did something interesting!)
Enterprise Customers
Adriaan (my co-founder and engineering legend) has been balls-deep in improving our analytics infrastructure for Simple Analytics. Why? We are getting more interest from really, really big (prospective) clients with really big websites.
After five years in business, the scale is tipping in our favor. I don’t know why, but that's just a feeling, and we want to be ready for it.
Getting enterprise customers is hard and takes a loooooong time. At some point, every startup wants to go after the big money contracts, but it is so much harder and takes so much longer than you think.
Here is how it goes for most companies (based on this spot-on article by Ben):
You start a company and build a product that sells to startups/SMBs. After that, enterprises should start using it as well. Bottom-up adoption. Easy peasy. Great strategy.
You create an Enterprise plan and pop the “Contact Us” button on your pricing page. Add SSO and priority support. Wait for big companies to come along (spoiler: they won’t, yet).
After a while, you get in touch with enterprises but never close deals. Your pipeline is full of conversations that will never turn into contracts.
Then, you close a smaller-than-expected deal with a public company and call it a win. Make a case study about it. Still waiting for the enterprise cavalry.
Two years in, still no real enterprise deal. Security teams and procurement become your worst enemies.
Your pitch finally lands with real decision-makers. They love your product...but don’t see enough big-name customers to buy it. See you in three years, maybe.
Slog through long enough, and eventually, some enterprises start showing up. But it takes way longer than you ever thought, and the journey is full of false starts and wasted energy.
This is exactly how it went at Simple Analytics.
After five years of slogging along, we’re finally hitting some of the promised enterprise land.
Enterprises are a completely different beast. Custom contracts, SLAs, procurement, DPAs. I messed up my first enterprise deals because I did not know their needs and wants.
Here is what I learned:
Don't say yes to everything. Say no to things and end with the sentence: “Is this a dealbreaker for you?”
What your product is worth to an enterprise client differs per organization. It is key to figure out this number—don’t be scared to mention a number that makes you feel slightly uncomfortable at first.
Use developers to sell to their managers. They are your way in. They can help you convince management to buy your product.
Don’t ever offer SSO for free.
Add expiry date to offer. Otherwise, deals tend to take forever.
Dodge discounts, but give something in return like quarterly payments instead of yearly.
When you offer a discount, ask for something in return, such as a case study.
Add clear “starting from” price to enterprise on the pricing page. It sets the stage.
If they really need a custom contract, charge at least 10K per year.
Final Thoughts
There you have it. Our September update.
To round it off, I’ll be writing my next update from Bali. I’ll be there with my co-founder, Adriaan, in November. If you happen to be around, just ping me!
Definitely hit us up if you’re looking to do some shirtless coding:
See ya next week! (and thanks again for reading. It's all quite new to me, but I hope you enjoy it. If you have any feedback, that’d be super appreciated!)
Cheers,
Iron
I admire your persistence and strategy. You’re not just building a business; you’re laying the foundation for long-term growth. The focus on corporate clients, SSO, and smart pricing is a powerful lever for scaling.