Hey Wranglers,
I started my first company during the financial crisis. Not ideal timing, but in some ways it was clarifying. The market was broken, but the rules were still the rules.
You knew what a good hire looked like. You knew roughly how long it would take to build something. You could map out an ROI case for a customer and expect it to hold.
I don't think that's true anymore.
Key Takeaways
The metrics that guided smart startup decisions for 20 years are no longer reliable. Headcount, build timelines, sales cycles, ROI projections: all of them are moving targets right now.
The noise is louder than it has ever been. A competitor can look like they're winning based entirely on LinkedIn posts and a big raise. Most of the time they're not.
AI hasn't just changed what you can build. It's changed how you prioritize. When everything feels suddenly possible, figuring out what not to do is the harder problem.
The fundamentals haven't disappeared. They've just gotten harder to see through the noise. Customers still buy from people they trust. Products still have to work. That hasn't changed.
The Big Picture: The rules changed (but not all of them)
When we started StatSheet in 2007 and grew into Automated Insights around 2011, how you built and grew a company was pretty stable.
The last five years don't feel like that.
Since we started Wrangle in 2021, there have been a ton of changes. From Covid, and remote work becoming the default overnight. To a SaaS "correction.” To ChatGPT arriving and changing the game. To non stop geopolitical changes. Then Claude once again reshapes what customers expected from every product on the market. Every few months, the ground shifts.
What's interesting is that each shift opens something up:
How fast you can build has changed dramatically.
How many people you need to do serious work has changed. The ability to test an idea that would have taken six months and real headcount to validate, you can do that in a week now. For a small team with conviction, that's actually a huge advantage.
How much you know today won't be how much you know tomorrow. The learning curve has never been easier to overcome, with advice personalized to you.
The challenge isn't that the rules changed, but that the old metrics for making good decisions haven't caught up yet:
How long should it take to ship a feature?
What's a reasonable sales cycle for an enterprise deal?
How do you build an ROI case when the customer's own costs are shifting as fast as yours?
Those questions don't have the same clean answers they used to.
But what I keep coming back to is that the fundamentals haven't disappeared. Customers still buy from people they trust. Products still have to actually work. Teams still need clarity on what they're building and why. None of that changed.
And the window to move fast and figure things out just got a lot wider for the people willing to stay close to the problem.
What I'm Noticing: What is worth building now that you can build everything?
When something that used to take three months now takes three weeks, the prioritization problem gets a lot harder.
I also keep seeing the same thing play out in the market. A lot of the companies making the most noise right now are raising the kind of money that was common in the early 2000s, with promises that sound familiar too.
The internet was going to change everything. It did. But pets.com didn't work, and Chewy came along fifteen years later and figured it out.
We're probably in a similar moment. Some of the loudest voices in this space right now won't be around in five years. Some of the quietest ones will be the companies that actually mattered.
The ones I'm betting on are the ones building with a real understanding of how humans actually behave inside the products they're selling, not just what the technology can theoretically do.
The Setup: Building a business case for a new tool
If you're an IT or ops lead trying to build a business case for a new tool in this environment, here's what's actually working:
1. Stop trying to calculate exact ROI.
The classic approach, map current cost, project future savings, present the delta, doesn't hold as well when the baseline keeps shifting. Your headcount assumptions from six months ago might already be wrong.
Build the case around the problem instead: What breaks when this doesn't exist? What does your team stop being able to do?
2. Start with one team and one request type.
The instinct is to make the case for the whole organization. That's also the case that's easiest to say no to. One team, one category of requests, two weeks of data. That's a story people can evaluate and a decision they can actually make.
3. Make the invisible visible before you ask for anything.
The most effective thing you can do before any budget conversation is show what's currently happening:
Support volume that nobody knew existed
Response times that nobody was tracking
Work that was disappearing into DMs and never getting counted
Data changes the conversation faster than any pitch will.
Thanks for reading. As always, reply if something here resonated or if there's a question worth digging into in a future issue.
Adam Smith
CEO & Founder, Wrangle
PS — What's the one assumption about your business that felt solid two years ago and doesn't anymore?