The AI Question Gets More Real (at Least for Some Entrepreneurs)
Entrepreneur Office Hours - Issue #291
Depending how deep you are in the creator world, you might have heard that YouTube announced a big update to its monetization policies: starting July 15, 2025, creators can’t earn ad revenue from mass-produced, low-effort videos (i.e. videos created with AI) unless they bring “real originality and added value.” Think of it as a crackdown on “AI slop.”
I’m bringing this up because it signals something interesting — and important — about how we create, communicate, and share value in our increasingly AI-driven world. Notice how YouTube's move isn’t about banning artificial intelligence outright (AI-driven creativity can be incredible). Think of it more like a reminder that real, sustainable value isn’t about the technology you use, but how you use it.
If you've spent any time building a business (or anything else) you already know that tools don't define the outcome; they amplify what you bring to the table. In that sense, AI can be a phenomenal tool, speeding up repetitive tasks, streamlining your workflow, and even inspiring new directions. But relying on AI alone, without human creativity, vision, and judgment, quickly leads to meaningless noise. YouTube, in other words, has recognized something entrepreneurs should never forget: real value demands authenticity and humanity.
I, for one, am excited about the policy. As YouTube goes, so will a lot of the other platforms. But I realize it also raises some difficult questions we'll all need to grapple with.
How much AI is too much?
How will we differentiate between genuinely creative AI-assisted content and lazy, mass-produced spam?
Will audiences become more discerning — or more confused?
And who, ultimately, gets to make the argument for what is and issn’t “allowed.”
Simply put, as creators, entrepreneurs, and innovators, our biggest challenge in this new era is going to be figuring out how to harness AI in a way that highlights our uniqueness rather than obscuring it. After all, at the end of the day, real connection and meaningful value still come from people, not algorithms.
At least, they do for now. I guess we’ll all have to see if that’s still true in the future…
-Aaron
This week’s new articles…
The 7 Red Flags You’re Talking to a Toxic Entrepreneur
How well can you recognize the warning signs of entrepreneurs you need to stay far away from?
You’ll Never Be a Great Entrepreneur if You’re Still Trying to Get an A
What if you accidentally learned your worst entrepreneurial habits by trying to get great grades in school?
Office Hours Q&A
QUESTION:
Hey Aaron,
I’m in this awkward spot where I’m working a full-time job while trying to build my startup on the side. It’s producing a small amount of revenue, and I’m getting good feedback, but it’s definitely slow growth, and I’m running out of motivation. How do I know when it’s time to go all in or, I guess, alternatively, when it might be time to give up on it?
Truly,
Mateo
Welcome to entrepreneurial purgatory! You’ve got one foot in, one foot out, and everything feels like it’s taking forever. And yeah, it’s exhausting.
Part of what makes this stage so brutal is that both options — going all-in or walking away — feel like some kind of failure. If you quit the job, you might crash and burn. If you quit the startup, you’ll feel like you didn’t give it a real shot. And so you stay stuck in the middle, dragging both around like two carry-ons that won’t fit in the overhead bin.
The truth is, there’s no perfect signal. No entrepreneur ever hits a milestone that magically says, “Yep, now’s the moment.” Going full-time on your startup will give it more oxygen, yes. But it also puts more pressure on every decision. You’ll have to grow faster. Monetize faster. Win faster. That’s not necessarily a bad thing — pressure can sharpen a founder — but it also changes the entire tone of the business.
Conversely, giving up means you’ll never know what could’ve been. And that can sting. But sometimes, holding on to a slow burn for too long becomes its own kind of anchor.
Here’s a thought experiment I sometimes give my students: If you shut the startup down tomorrow, how would you feel the next day? Relieved? Regretful? Restless? Free? Be honest with yourself. Your answer won’t make the decision for you, but it’ll help reveal which direction your gut is already leaning.
And if you do decide to keep going — even part time — then make that decision deliberately. Don’t limp forward. Design a version of the startup that fits your life right now. Shrink the scope. Set small goals. Run experiments. Don’t try to “win,” just try to learn. Remember, while you think you’re building a startup, you’re really building yourself as a founder. And that matters more than whether this one hits.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.