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Q2 Feels Different When You’re Charging 4x More

Last Year: Simpler, But More Daunting

Last year around this time, life was simple. And by simple, I mean completely daunting. We were charging a ¼ of what we do now, had raised a grand total of zero dollars, and my days were mostly spent on 1:1 calls with families and individuals, trying to convince them that, yes, we actually knew what we were doing. Spoiler: we kinda did.

We were slowly gathering momentum. We had about 15 firms on our platform—some of which were absolutely crushing their intros. Our metrics were insane. 80% of our users met with 2-3 advisors, organically 25-50 new families per month were joining, nearly 90% of users were referring, and I was basically living on the phone with advisors and families. Life was good.

Except, you know, for the part where I was making zero dollars, our team was a quarter of the size it is now, and the future was just one big shrug emoji.

Fast Forward: Growth Brings New Problems

Fast forward to today: we do more in a single month than we did in the entirety of 1Q24. But now we have a different problem—our prices are up 3x-4x, and some of our longest-standing firms are feeling the squeeze. And look, I get it. No one loves a price increase.

But in my mind, you haven't hit the right price until 20% of your customers churn specifically because of it.

If everyone keeps buying, you're either leaving money on the table or undervaluing what you bring to the table.

The Churn Dilemma

But that churn question? It’s a tough one. Do we spend time trying to retain customers who are balking at the new pricing, or do we focus on the 300+ firms sitting in our pipeline, waiting for open slots? (Not exaggerating—100+ of them have followed up in just the last four weeks.)

• We average anywhere between 10-15 (new) demo requests each month

• 90% of these come through LinkedIn

• Each demo equals anywhere between $7k - $59k in annual revenue

And that backlog exists because, outside of product and engineering, our frontline team is basically five people. Sounds like a lot, right?

Except Veera (co-founder) is running product, engineering, ops, payroll, hiring, roadmaps, OKRs, standups—basically everything that makes the company function.

We’ve got two killer interns handling consumer facing stuff, Matt (our customer success guy) wearing 17 different hats between web dev, sales, and 1:1 consumer calls, and then there’s me, half the time not even sure what the hell I’m working on because it’s everything all at once.

Prioritizing Depth Over Breadth

So yeah, we’re not trying to work with everyone. We’d rather go deep with 50 firms—firms that see the long-term value, that want to own multiple subscriptions and integrate with our ecosystem for years. The firms that just want to pick up a few clients and bounce? That’s not the culture we’re building.

And that leads us back to the never-ending debate: focus on a few big wins with larger, newer firms, or keep everyone happy by renewing at a lower price?

The Reality: No Right Answer

Here’s the truth: there is no right answer. It’s all just one big experiment. Test, tweak, repeat. Things will break. Customers will get pissed. Some will say we’re moving too fast, others will say we’re moving too slow. And that’s fine.

Because one year ago, I was begging people to take my calls, pitching a Squarespace landing page, a fancy deck, a handful of viral TikToks, and a dream.

And now? Now we’re in the driver’s seat.

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What’s Coming Next?

It’s been a while since I’ve done this, but I believe it’s integral to share the side of me that not many see. And for some this will come at a shock.

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