It’s been a few weeks since my last update on building Marked Closed Won, and yeah… a lot has happened.
Last time I wrote, we hit a milestone that sounds like the part where you cue the movie montage: six figures in annual recurring revenue in less than 2 months.
And to be clear, it is great. I’m proud of it. I’m grateful for it. I’m still kind of shocked by it some days.
But here’s the part people don’t always talk about: right after that milestone, sales tapered off. Not crashed and burned. Not “panic stations.” Just… slowed. The pipeline didn’t feel as spicy. The momentum didn’t feel as automatic.
And if you’ve ever built anything from scratch, you know that’s when your brain starts doing what brains do best: making up worst-case scenarios at 2:17 AM.
Why Sales Slowed Down (No Dramatic Plot Twist… Just Reality)
The truth is, there wasn’t one single “this is why” moment. It was a mix of situational stuff… and a classic business issue that I’m learning is basically universal:
Our focus got divided.
My business partner was pushing hard on new leads. My wife was deep in operations and onboarding (aka the part that determines whether customers stay happy or quietly churn later). And I was in the weeds on the day-to-day while also building out the podcast.
None of that is bad. In fact, it’s all necessary.
But it does create this weird tension where you’re growing… and also trying not to drop the plates that growth adds to your hands.
The Good News: We Didn’t Abandon Lead Gen
One thing I’m proud of is we kept with the lead gen.
A lot of businesses get a big influx of clients and then immediately go heads-down on fulfillment. Totally understandable. The problem is: lead gen becomes anemic, and then a few weeks later you look up and realize you’re running on fumes.
We didn’t let that happen.
That said… we still hit a several-week dry spell.
The Dry Spell Was Real
Even with lead gen still running, we hit a stretch where the opportunities were there, the conversations were happening… and the deals were not closing.
That’s the maddening part, right? Because it’s not like you can point to one broken lever and go, “Ah yes, the ‘close more deals’ switch is set to OFF.”
We had several sales opportunities, but for one reason or another, they just didn’t convert.
So we did what you do when you don’t have a magic wand: we kept showing up. We kept following up. We stayed in motion.
And then, like it always seems to happen in sales, several deals closed at once.
Not because we suddenly became geniuses overnight. More like the timing finally caught up to the work. Sales is funny that way. You can feel like you’re losing for weeks and then win three times in a row on a random Tuesday.
Meanwhile… The Podcast Got Built (For Real This Time)
At the same time, we were building out the podcast side of the business, and there were a few key pieces that needed to get buttoned up if we wanted this to be consistent and not chaotic.
We built the calendar flow for both the pre-recording meeting and the actual recording session. That sounds simple, but it’s the kind of structure that stops something from being “a fun idea” and turns it into “a real machine that runs even when life gets busy.”
As of right now, we’ve got momentum:
- 4 podcast episodes posted
- Another episode recorded and scheduled for next week’s drop
- A social media plan being formulated and actively executed
And honestly? Watching it come together has been energizing.
It’s been fun to see the marketing material go out, to get views and interactions, and to feel like we’re building something that has a voice, not just a product.
What I’m Learning in This Season
If I had to sum up the last few weeks, it’d be this:
Milestones don’t remove the need for fundamentals.
Hitting six figures in ARR didn’t mean the sales train just keeps rolling forever. It meant we hit a checkpoint, and then immediately had to figure out how to keep the engine running while also expanding the track.
It’s not always glamorous. Some days it’s exciting. Some days it’s annoying. Some days it’s both within an hour.
But it’s real. And it’s moving.
More to come soon.
