What happens when you throw out the GTM playbook
That investor was wrong. Gamma is now worth $2B, with 50M users and more than half their growth driven by word of mouth.
They're one of 6 AI-native startups in HubSpot for Startups' free Bold Bets Playbook. Replit grew revenue 50x after half the team pushed back on the strategy. Ramp generated 100M+ views from a single stunt. Clay's co-founder wouldn't hang up a sales call until the prospect DMed him in Slack.
Each one took a GTM risk most founders would never greenlight. Each one paid off.
CAREER STRATEGY NEWSLETTER
I recently posted something that landed differently than I expected.
I asked whether one person can build a billion-dollar company. The honest answer is I don't know yet. I'm running the experiment in real time. But the responses told me something.
The question people actually care about isn't can it be done. It's what does it feel like to try.
Let’s dive in
What’s happening right now
For most of corporate history, scale meant people. You grew revenue by growing headcount. More accounts, more reps. More complexity, more managers. The org chart was the company.
That link is breaking.
Not slowly. The tooling now exists for one person to run functions that needed a team of ten 3 years ago. Research, drafting, analysis, outreach, ops. I'm doing it across the business with a stack of AI agents handling the work.
The same force is hitting your world from the other side.
When a company can get more done with fewer people, the middle of the org chart is where the compression is currently taking place and not at entry level only as everybody seems to be focused on. The Director and senior manager layer is hit hardest.
The exact group I write this newsletter for.
You're not imagining the squeeze. The structure that used to reward a 15-year climb is flattening.
~50% of all observed layoffs hitting manager level or above in 2023 and the trend has increased in the last 3 years and Manager headcount fell 6.1% from May 2022 to May 2025.
Why people are reading this wrong
The common reaction is to treat it as a capacity story. AI does more, so we need fewer humans. True, but it misses the real constraint.
I learned this the hard way over the last few months.
Running solo on a stack of agents feels like leverage but in practice, each agent sits in silo. None of them knows what the others are doing.
So you become the messenger, copy-pasting context between tools all day.
And the memory lags. One agent thinks you closed a deal you haven't. Another quotes a cost that changed weeks ago. You end up being the only thing holding the truth together, across a dozen open tabs.
The bottleneck was never how much the machines could produce.
It was whether I could trust what they told me without checking it myself.
That distinction matters far beyond my situation because it's the same problem facing every senior professional right now. The market is flooded with tools that promise to do your thinking. The difficult bit is to know which answers to trust enough to act on if you even bother checking outputs in the first place which less and less people are doing!
The reframe
So I stopped trying to make the agents talk to each other. I built a different thing.
A single brain that holds the entire’s business information (think of it as a Chief of Staff). Scheduled agents (various Departments) keep it fresh, but here's the rule that makes it work: they only write when they can verify a fact against a live source. If they can't, they flag me (the CEO) instead of guessing.
Every agent (Team members) reads that document before doing anything else. No re-briefing. No stale numbers. One source of truth that updates only when the facts check out.
Here's why I'm telling you this in a career newsletter.
The principle scales down to a single career just as well as it scales up to a company.
Most people in transition do the opposite of what I just described. They collect inputs from everywhere, a recruiter's comment, a LinkedIn post, a friend's opinion, a salary figure, and they hold it all loosely in their head.
A career operating system does the same job as my Chief of Staff. It holds one verified picture of where you actually stand. Your real market value, not the number you assume. Your transferable authority, not the job title you're attached to. The options genuinely open to you…
That's a sliver of what I'm building with Zelova with senior professionals in mind. The same discipline I'm using to run a business, turned into a structured system for running the most important transitions and milestones of your career.
One last thing
This lands for me right now because I spent years scaling commercial teams, adding headcount to add capacity. And I'm now running this next venture in a way that questions the perennity of these more traditional models.
None have the answers yet. But I'm convinced the next decade belongs to people who can pair human judgment with systems they can actually build and trust. At every level. The founder running a company of one. The Director deciding what comes next.
If any of this is live for you right now, I'd like to hear your version. The squeeze, the tooling, the question of what to build on. Reply to this email or message me directly.
And if you want to be early to what I'm building, the waitlist is open at zelova.ai.
David


