Operator mode
Back when I was raising money for my company, I grouped investors into two groups: realists and dreamers. Realists made our idea smaller by finding all the reasons it would fail. Dreamers made our idea bigger by imagining category-bending ways to apply it.
In time, I grew to appreciate both personas. But as a dreamer myself, I'll admit that I was more drawn to the dreamers. Especially early on when our ideas were new and fragile.
I've spent the last few years working as an operator inside a big company and coaching other founders on their businesses rather than building my own. In both of these chairs, I am paid to be a realist, not a dreamer. The job is to see around corners and find a way to achieve the dream despite tough constraints.
Recently, I asked myself: Do I still know how to dream?
Just crazy enough to work is not very crazy
In traditional B2B, nearly every AI company is fighting over a small number of well-understood spaces. I don't know how many recruiting, sales, and marketing agents there are on the market, but at least thousands. Finance AI promises to build your financial models better and faster. HR AI will supervise your employees and coach them and answer their questions about benefits. You can choose your favorite AI personal assistant and it will glue all the rest together.
Truth be told, it is hard to tell these solutions apart. Some products work slightly better than others, usually when they are well fit to your workflow. Some are built with interesting proprietary data. A few have more or less prominent security and privacy issues. But they are all built on the same foundation models and they all make the same promise: they will optimize the way your company (already) works.
These efforts come from the minds of excellent (excellent!) operators, not product visionaries. Increasingly, there is no line between internal AI transformation work (done by operators, always) and productizing that work for external customers. If you can cut through the noise and secure some kind of distribution advantage, you may even make some money.
I would never diminish the efforts of any founder, but these aren't dreamer companies. Rather, they aim to address very specific operational hangovers that are holdovers from the SaaS era.
In other words, these efforts are led by realists and operators, not dreamers.
If dreaming were easy, everyone would do it
Don't get me wrong, realist endeavors can be massively successful. Many of the best companies of the SaaS era were realist companies. Box, Zoom, and Workday are all great examples of companies that won big by methodically and rigorously applying modern technology to well-understood operational problems. They built better mousetraps. Often much better.
But building a better mousetrap is not the same as creating a category. New categories essentially represent dreams of new ways to live and work. Slack turned workplace chat into the primary layer of work. Figma turned design into a team sport. HubSpot recognized that inbound marketing was the only way that small businesses could afford to grow, and they built software and a content juggernaut around this premise.
These are dreamer companies that created new categories. Along the way, they've employed many outstanding operators. But they all started with a dream.
Not every aspiring category creator wins big (ask me how I know). To make a dreamer company successful, it is not enough just to have a compelling dream. You have to pair the dream with the methodical and rigorous execution of any more linear company. For dreamers to succeed, they need operators and realists around the table too.
Life is but a dream
Last year, a random stranger on LinkedIn asked a question that has stuck with me since. She asked: What problem are you most passionate about solving?
This is a dreamer question. It is different from the analogous operator question:, which is: "What problem can you solve better than the status quo?"
If solving the problem you're most passionate about perfectly aligns with the work you get paid to do, you are in a fortunate minority. For most people, their day job is simply the thing that pays the bills; a few lucky people enjoy it. But it is rare that the problem someone most passionately wants to solve is also the problem they get paid to solve.
But more than any other question, "What problem are you most passionate about solving" is what unlocks our ability to dream.
Give it a try.
Kieran
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