AI Pivots: How to Test Fast and Scale Smarter

Welcome back to Founder Mode!

One of the hardest choices for any founder is knowing when to pivot. Sometimes, the data leaves no room for choice. You must let go of your “favorite” ideas and head in a new direction.

Recently, we ran a campaign that looked great at first glance. We were pulling in leads for $25 per conversion. On paper, that’s a win. After weeks of chasing leads, I realized that getting a $200/month client wasn't worth it.

The real lesson? Low-ticket, high-churn customers can be a death trap.

We're focusing on higher-value customers. We're targeting deals worth a min $50K in ACV. This may lead to a longer sales cycle, but it's worth it.

By the way, last week on the pod, we flipped the script with Bobby Evans to talk about how not to run a startup. From over-hiring and bonus wars to wasted features and vanity metrics, we dug into the mistakes that quietly kill momentum. This episode is a blueprint in reverse—showing founders what to avoid so they can move faster, stay lean, and protect their time.

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Going back, let's discuss our plan for this pivot, what we’ve learned, and how you can test your changes safely.

Kill Your Darlings

The first step is emotional: you have to let go of ideas that feel good but don’t scale.

I said to the team, “Sometimes the data tells you to kill your darlings.” And this was one of those times.

It stings to walk away from a funnel that looks healthy on the surface. If the economics don’t make sense, cut it quickly. This way, you can chase better chances faster.

Find Your Niche and Go All In

Being a generalist might get you started, but it rarely gets you paid.

We identified a $16B market that’s non-tech-savvy and feeling a very real pain point. We're moving away from a "generic AI" pitch. Now, we will focus on being the top choice for one specific area.

The bet is clear: specialists shout credibility, while generalists get lost in noise.

Test Without Burning Bridges

A pivot doesn’t mean you erase everything you’ve done before. It’s about layering, not nuking.

Our approach:

• Move the old homepage to a sub-page (like /voice-agents).
• Set the new niche-focused message as the main landing page.

This lets us focus on the new vertical while keeping our old leads intact.

This allows us to test the pivot in real time. It also protects the foundation we’ve built.

Speed Over Perfection

Validation isn’t about six months of overthinking. It’s about getting an early signal as fast as possible.

Our plan:

• Launch a targeted landing page in one week.
• Run a few hundred dollars in ads.
• Aim for 5 calls booked.

If those calls happen, we know we’re onto something. If not, we pivot again. Speed is the weapon.

Old-School Markets Need Old-School Tactics

Here’s something you don’t hear often in AI circles: LinkedIn and email aren’t enough.

Our new ICP isn’t hanging out in Slack communities or on Twitter threads. They will attend trade shows, read mail, and answer phone calls.

So we’re testing:

• Cold calling key accounts.
• Direct mail campaigns (yes, envelopes and stamps).
• Attendee lists from low-tech industry conferences.
• Walking into offices - a new meaning of 'return-to-office'

If you want to win in traditional industries, you can’t be afraid to use traditional tactics.

5 Key Takeaways

1. Kill your darlings. Don’t chase funnels that don’t scale.
2. Pick a niche. Specialists cut through noise; generalists get ignored.
3. Test smart. Layer pivots without wiping out your current business.
4. Move fast. Validation should take weeks, not months.
5. Match your market. Old-school customers need old-school outreach.

Final Thoughts

Pivots aren’t signs of failure. They’re signs of learning. Every founder I know has had times when the market rejected one idea and embraced another.

The key is to listen fast, test fast, and move fast.

I’ve found that going after low-ticket, high-churn customers is the real nightmare. The better path is harder: go upmarket, specialize, and meet your customer where they already are.

As founders, we don’t get to choose when the market forces us to pivot. But we do get to choose how quickly we respond.

See you on Friday,

-kevin

Recent Social Posts

Kevin Henrikson @KevinHenrikson Most founders talk about what worked. @bobthewizard23 came to break down what didn’t. → Overhiring, fast → Vanity metrics, louder → Shipping late, overpolished → Missing the moment by trying to be perfect → Forgetting that your face is your brand Founder Mode – Episode 26 7:36 AM • Sep 25, 2025 16 Retweets 30 Likes Read 2 replies

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