November 1, 2025
I just listened to Side Hustle Nation episode 700, where Tanya van Gastel talks about building Multiverse AI—an AI headshot generator that went from $9 sales to $350,000 in revenue before they sold it.
The story is impressive from a business execution standpoint, but it raises a question I keep coming back to: What do we owe large faceless corporations like Reddit and Google versus what do we owe our fellow humans using those platforms?
The tactics that built this business force us to confront that tension.
The Good Stuff: Actual Business Lessons
There are some legitimately smart moves here that any side hustler should pay attention to:
Optimize for Revenue First - They didn't try to build a billion-dollar company. They started at $9 per headshot, scaled to $29, and focused on actually making money.
You Don't Have to Win Everything - One of the best points Tanya made: most markets are not winner-take-all. You don't have to become the global hyperscaler in your niche. You can build a very nice lifestyle business that treats you well personally and generates real income.
Enterprise Pricing Matters - They figured out how to price for bulk/enterprise customers so larger organizations would take them seriously. This is a lesson I've learned the hard way—if you price too low, people assume you're not legit. Price for the customer you want.
Affiliate Marketing Works - They gave affiliates 30% commission and their best affiliate was making $10k/month (driving $30k in revenue to the business). Smart distribution is just as important as having a great product.
The Sketchy Stuff: Where It Gets Uncomfortable
Here's where my inner conflict kicks in:
The Reddit Spam Problem - They openly talked about posting on Reddit threads, commenting to sell their service, and getting banned constantly. They'd search for "headshot AI" threads and jump in to promote.
Now, from a pure business perspective, you could look at the internet as just a state machine you can poke at for results. But there are real humans on the other side.
When you spam communities, you're not inflicting harm exactly, but you're creating an additional intellectual tax. You're forcing people to spend brain cycles filtering out commerce from conversation. You're interrupting cognitive flow with promotional content—which is kind of what we do all the time in America, but still feels a little icky.
Paid Rankings = Enshittification - The affiliate program drove them to #1 rankings on "best AI headshot generator" listicles. But here's the thing: they're paying 30% for those recommendations.
This is basically what Cory Doctorow calls "enshittification" in action—you can't trust these rankings because they're bought. (He talks about this brilliantly on The Gray Area podcast with Sean Illing.)
The site converted well, sure, but how much of that was because they were actually the best vs. because they paid the most?
The Real Question: What Do We Owe?
Here's what I keep coming back to: What do we as individual entrepreneurs and small business owners owe the large aggregation sites like Reddit? Do we owe them civilized behavior? What about hyperscale platforms like Google? Do we owe them anything?
I think the answer is that we don't owe them anything. These platforms farm all the content their users create for revenue. They monetize our conversations, our questions, our answers. Reddit doesn't pay the people creating the value on their platform. Google doesn't compensate the websites it scrapes and ranks.
And that's actually the challenge, right? We don't owe these large faceless organizations any particular quality of behavior.
But what do we owe our fellow humans? That's the interesting question.
In the age of AI, the question isn't how do you automate things—it's how do you actually improve human-to-human communication.
When you spam Reddit, you're not hurting Reddit Inc. You're creating minor inconveniences for real people in that community who are trying to have a real conversation.
When you game affiliate rankings, you're not hurting Google's algorithm. You're adding an intellectual tax on real people trying to make informed decisions.
Current AI Headshot Generator Landscape
Speaking of which, here's what's actually out there in the AI headshot space right now. The market is crowded, which proves Tanya's point about timing the exit right.
Note: The descriptions below include marketing claims from each service (e.g., "professional-grade," "fast delivery," "exceptional realism"). These are marketing terms, not necessarily objective reality.
Premium Options:
- HeadshotPro - $29-$59, 40+ headshots, money-back guarantee
- Aragon.ai - Higher price point, claims photographer-quality results
- StudioShot - Markets itself as LinkedIn-ready with exceptional realism
- BetterPic - Highly customizable (clothes, backgrounds, human edits)
- ProPhotos.ai - Claims professional-grade results with quick turnaround
Mid-Range:
- BetterShot AI - $29 for 72 headshots
- Try It On AI - $21 for 100-200 headshots
- The Multiverse AI - The one from the podcast
- Profile Picture AI - $29 for custom headshots
- Headshot Generator - Multiple packages, claims fast delivery
Free/Budget:
- ChatGPT - 3-5 headshots per day on free plan
- Canva - Integrated AI headshots, under 1 minute
- InstaHeadshots - Claims 15-minute turnaround
- Fotor AI Headshot Generator - Free tier available
- PhotoAI - Free trial with limited headshots
This blog post was created in conjunction with AI (Claude Code), through 9 revisions.
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