A few weeks ago, I was in St. Louis, meeting the Gateway X venture studio team, when Jesse slacked us all a big idea:

What if Bootstrapped Giants focused on AI?

GX has been looking into acquiring AI companies. The more they dug into their businesses, the more excited they became about the future of AI.

So I started a series of conversations to help me understand what’s possible.

Today I want to share 2 eye-opening stories and ask for your help.

Story 1: Unbelievable story

I talked with a founder who vibe-coded apps that do $10 million a year.

He refused to let me reveal his name (yet), but I persuaded him to talk with me in private.

Background:

He previously raised money for a startup. But he burned out on things like leading big teams. (His current company has 0 employees. Just him, his fiancée and AI tools.)

He sold his VC-backed company.

While he's on his 3-year earn-out, he's spending weekends building apps.

What he’s building:

He's creating iPhone apps that solve problems that irritate the hell out of him.

One app he showed me makes total sense to any dad who needs his kids to quiet down before bed.

How he’s building

Cursor - apps creation

OneSignal - user communication

Firebase - backend databases hosting

Paddle - payments collection (5% commission vs Apple's 30%. And to avoid tax headaches.)

Intercom - AI-driven customer support

AppsFlyer - data attribution for paid ads (meta, TikTok, Google)

Adapty.io - revenue management for in-app purchases

FunnelFox - create funnels that convert visitors into paying users

My takeaway:

I wanted to leave this conversation being able to tell you that "AI makes it easy for anyone to build an app and earn $10M/year."

This founder thinks that's possible.

I’m not sure.

He's a full-stack developer, so Cursor seems easy for him. He can build a full app in a weekend using AI.

But to the average person, Cursor is still too techy.

Also, I went through his funnels. He has an intuitive understanding of user psychology.

He uses onboarding multiple-choice questions to get users to understand why they should pay for his apps.

Others’ response:

When I wrote about him on my LinkedIn, some people said this is the future of entrepreneurship. A single founder with a deep understanding of a problem can build a solution and profit from it.

But some readers thought this story wasn’t believable.

I feel confident about it. I met him through Pavel Doležal, a reader of this newsletter who founded Keboola. He confirmed the story and is shocked that anything in this story would be new to people. “It’s 2025,” he said.

I also ran my full conversation by Adam, Gateway X’s CTO, who confirmed that everything this founder did is possible — but he also showed me how he uses Cursor so I’d understand that it’s not quite consumer-friendly software.

Story 2: The tough beat

Google killed a company while he tried selling it to us.

One of the best parts about running a Gateway X-backed company is the access I get.

As soon as I expressed interest in moving Bootstrapped Giants into the AI space, Jesse and team invited me to their M&A meetings.

Background:

I sat in on a meeting about a Chrome plugin that took off incredibly fast.

Its’ based on a killer idea: a Chrome plugin that analyzes data on your screen.

It has 400,000 users. Thousands of them are paying.

Meeting:

In the meeting, Jesse asked, "What if Google builds that functionality into its software?"

We got a blank stare.

I jumped in and said, "Actually, I have early beta access from Google. Looks like they launched a Gemini tool that copies what you built."

"Where?" the seller asked.

I turned on screen share and showed him.

The meeting ended soon after.

My takeaway:

The opportunity in AI software is big, but so is the risk of getting Sherlocked.

But others disagreed:

I wrote it up on my LinkedIn to get feedback from people.

I got a lot of “that’s what you get for being small” responses.

But a few people said he shouldn’t give up. Go deeper and create a more useful tool than Google for a narrower market than Google cares about. They also said that Google has a history of screwing up user experience, like the way they incorporated Gemini into Google Meet.

I’m asking for your help

I’m looking to understand AI businesses better.

Do you have a business in AI?

Tell me what you’re up to.

Do you know of a business in AI that I should talk with?

Tell me about the company.

Is there something you want to know?

I have incredible access. I plan to do more interviews with founders in AI. What do you want to know?

Does this sound like BS?

I want your skepticism, too. None of the people who poked holes in these 2 stories hurt my feelings. They made me smarter. If you’re doubtful, hit reply and tell me your doubts.

Bottom line: Hit reply and tell me what you think/know. I’m in deep research mode.

~andrew