Zak Kann - AI Automation for SMBs

04/07/2026

685 cold emails. Two replies.

One person said "take me off your list." The other was confused about how I got their name (I'd found their job posting for a content writer and pitched them an SEO tool for their new hire. In hindsight, that's a weird thing to receive from a stranger).

Nobody said yes. Nobody said no. Nobody asked a single question about the product.

I spent months building an email pipeline, researching companies, verifying contacts, writing sequences. All aimed at the wrong audience. Content managers at SaaS companies don't shop for SEO tools. That's like selling kitchen knives to restaurant owners. The chef picks the knives.

The people who actually buy content optimization tools are SEO freelancers. They pay for Clearscope or Surfer out of their own pocket. They feel the $129/mo. They switch when something better comes along.

So this week I'm doing something different. No more cold emails. Just conversations. Emailing every customer who left to ask why. DM-ing freelancers to understand how they pick tools. Asking my one loyal customer how he found me in the first place.

I'll share what I learn.

Anyone else ever built the whole machine before realizing it was pointed in the wrong direction?

04/06/2026

My morning:
"Can't do prospect enrichment; Claude Code is down. I guess I'll work on my taxes."
"Nope, I can't do that. Claude is down. I'll..."
[30 failed attempts later]

"My name is Zak, and I'm an AI-aholic. It's been 10 minutes since my last prompt."

03/24/2026

Opus 4.6 is a major gaslighter.

It loves to tell you issues are pre-existing, not caused by its work. "Oh that bug? That was already there before I touched it."

Every testing flow now needs a "verify pre-existing issues by running on the old code" step.

Trust but verify. Especially with AI.

03/23/2026

In 2022, AI struggled to multiply two-digit numbers.
In 2023, it outscored most law school graduates.
In 2024, it was shipping production code and breaking down PhD-level research.
By the end of 2025, elite developers were openly admitting AI handles the bulk of their engineering.
We're barely into 2026, and it already feels like the ground is shifting faster than ever.

03/20/2026

My workday in 2026: describe what I want built, watch 6 AI agents spin up in parallel worktrees, each doing deep research before writing a single line of code.

I went from managing engineers to spawning an unstoppable army of transient wizards.

03/05/2026

I track one number every Monday morning. It's not revenue.

For the longest time I was checking my Stripe dashboard first thing every morning. Revenue up? Good day. Revenue down? Bad day.

Turns out that's a terrible way to run a business.

Revenue is a lagging indicator. By the time it drops, the damage happened 3 weeks ago. By the time it spikes, you made the right call a month back. You're always reacting to old news.

The number I actually track now: activated users in the last 7 days. Not signups — people who signed up AND did the thing my product exists for.

Here's why this one metric runs my entire week:

If activations are up, growth is coming — even if revenue hasn't moved yet. If activations are flat, something is broken in onboarding and I need to fix it before it shows up as churn in 3 weeks. If activations drop, I don't panic about revenue. I go find where people are falling off.

Revenue is the scoreboard. Activations are the game. You can't change the scoreboard, but you can change how you play.

What's the one number you check first every week?

03/04/2026

5 years later, I think this is the most prescient article I ever wrote.

There are no safe jobs, but lifelong learning can make you safer

03/04/2026

The micro SaaS market is projected to hit $60B by 2030.

Everyone's reading that number and thinking scale. I read it and think: calm.

The founders pulling ahead aren't the ones raising Series A. They're the ones running $30k/month businesses with zero employees. 70%+ profit margins. No board meetings. No runway conversations.

I've watched this shift happen in real time. The indie hackers winning in 2026 all have the same playbook:

They picked a niche so specific it sounds boring. They ship alone (or with AI). And they optimized for margin, not growth rate.

Meanwhile the VC-backed competitor is burning $200k/month trying to be everything for everyone.

I'm not anti-ambition. I'm anti-complexity-for-its-own-sake.

The best business I ever built was the one where I woke up on Monday and didn't dread opening Slack. That's not a lifestyle business. That's a competitive advantage.

Chase calm. The money follows.

03/04/2026

Stop building AI wrappers. Start building AI workflows.

I keep seeing the same startup pitch: "We built a UI on top of GPT-4."
Cool. So did 10,000 other people last weekend.

Here's the thing though — the winners in AI aren't building chatbot interfaces. They're embedding AI into workflows that already exist.

Nobody wakes up wanting "an AI tool." They wake up wanting their job to suck less.

The real opportunity?
→ Take a painful, repetitive process someone already does
→ Plug AI into the middle of it
→ Save them 10 hours a week

A wrapper gets replaced the moment OpenAI ships a better playground. A workflow becomes the thing people can't live without.

Build the thing that's hard to rip out, not hard to replicate.

02/18/2026

How long before LLMs are programmed with near real-time data?