Hard Mode FirstChatGPT Saved My Life (No, Seriously, I’m Writing this from the ER)
How using AI as a bridge when doctors aren't available can improve patient-to-doctor communications in real time emergencies
Hard Mode FirstHow to Plan an Annual Family Summit
Simple strategies for setting goals and Priorities with Your Partner for the year ahead
Hard Mode FirstHow I Used AI to Save My Life in 77 Prompts: A Debrief
Reflecting on best practices, lessons learned, and opportunities to improve AI-assisted medical triage
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Lessons learned from a lifetime of doing things the hard way, the first time
January should have been a pivotal month for my business. After one year of striking out alone, it was the first time I cleared enough in bookings to pay myself the salary I’d been holding out on for the past year.
But there was just one problem: Every single client paid me late. On paper I was sitting on $30k of corporate bookings, but the reality was much bleaker.
I got a blowout and showed up anyway to 30 Years in Silicon Alley, a party celebrating every founder, VC, and operator who’d made NYC tech work for them.
I walked past all of them, straight to the open bar and then, onto the dance floor, where I ran into a friend.
“Bethany!” she greeted me warmly. “How are you? You’re killing it on LinkedIn!”
One drink in, I stopped performing. “You want the truth?” I ask.
“Of course!”
I lean over and whisper in her ear. “The truth is that I have $37 in my business checking account right now.”
The irony wasn’t lost on me: I teach people to use the great equalizer, and I still can’t pay myself.
January should have been a pivotal month for my business. After one year of striking out alone, it was the first time I cleared enough in bookings to pay myself the salary I’d been holding out on for the past year.
But there was just one problem: Every single client paid me late. On paper I was sitting on $30k of corporate bookings, but the reality was much bleaker.
I got a blowout and showed up anyway to 30 Years in Silicon Alley, a party celebrating every founder, VC, and operator who’d made NYC tech work for them.
I walked past all of them, straight to the open bar and then, onto the dance floor, where I ran into a friend.
“Bethany!” she greeted me warmly. “How are you? You’re killing it on LinkedIn!”
One drink in, I stopped performing. “You want the truth?” I ask.
“Of course!”
I lean over and whisper in her ear. “The truth is that I have $37 in my business checking account right now.”
The irony wasn’t lost on me: I teach people to use the great equalizer, and I still can’t pay myself.
Hard Mode FirstChatGPT Saved My Life (No, Seriously, I’m Writing this from the ER)
How using AI as a bridge when doctors aren't available can improve patient-to-doctor communications in real time emergencies
Hard Mode FirstHow to Plan an Annual Family Summit
Simple strategies for setting goals and Priorities with Your Partner for the year ahead
Hard Mode FirstHow I Used AI to Save My Life in 77 Prompts: A Debrief
Reflecting on best practices, lessons learned, and opportunities to improve AI-assisted medical triage
When ChatGPT first emerged in 2022, some of us saw this as technology’s opportunity for AI to be the great equalizer. The tool that would finally make credentials matter less, not more.
You didn’t need to be a developer to build a working app. You didn’t need a degree from Stanford or Sand Hill Road connections to build something real and get it in front of the right people.
I believed it, too. And last year, along with many others, I got to work and started down a path of building an imaginative AI-powered learning companion for my kids. But about six months in, reality hit: I ran out of money, which meant really that I ran out of time to keep poking at this problem for long enough to make it work.
Rather than scrap it all for full-time employment, I pivoted. I recognized that even though I couldn’t take my own ideas across the finish line, I could help other people like me get theirs there, too. So I started offering to teach back what I’d learned.
Like a lot of people, I learned pretty quickly that there’s a lot more money in corporate workshops than in one-off individual sessions where you have to fight to earn every new recruit.
From the outside, I look like I’ve already made it. But the reality is that I’ve never felt more cash-constrained in my entire career. And I’m not alone. Over the past 18 months I’ve watched dozens of smart, capable friends opt out entirely. Not because they failed, but because waiting has a cost that eventually becomes too high.
The landscape is falling into place as naturally as ever before. Corporate training programs with five-figure price tags. Enterprise licenses sold to companies who were already winning. Bootcamps priced at $3,000. Not exactly the actualization of that idealistic “AI for anyone” dream. What we’re seeing instead is a mirroring effect from what we saw during the last digital revolution: The people who already have the resources and the runway to experiment get there first. Larger firms are investing more than smaller shops. So the money (and the resources, and the talent) follows suit. Nobody is incentivized to build for everyone else.
The person nobody built for isn’t hard to describe. She’s making $60k and trying to go independent but can’t afford to stop her salary long enough to find out if it works. He’s been in the industry for fifteen years but his resume doesn’t have the right logos on it so the warm intros don’t come. She’s already running her own business, found out about AI on her own, taught herself the basics on YouTube, but then got stuck. She knows she could be building something real with it. But she has no room, no cohort, no one standing in front of her saying, “Here. Click this now. Try it this way instead.”
Corporate boards are pushing AI upskilling through every department. Individual coaching clients with the financial means to take learning into their own hands are inviting me into their home offices once a week to work through the basics of ChatGPT, Gemini, and Claude.
It feels good to have enough in the bank to afford my own life. But I can’t stop noticing who I’m not serving.
My clients today aren’t people whose entire financial arc could change because of AI. These are the people who already have the funding, the resources, and the runway to treat learning as an investment. They were going to be fine before I showed up. They’ll be fine after.
Meanwhile the people who actually need this — the ones standing on a dance floor with $37 in their account, the ones one bad month away from stepping back entirely — still can’t afford to hire me.
At my current pace, I’m on track to 5-6x my revenue from last year. But I’ve already rebuilt the exact hamster wheel I was trying to escape. Different clients, same problem. The people with budgets get the room. Everyone else gets a YouTube video.
Which leaves me with one question: What about everyone else?
I don’t have a clean solution yet. I know what needs to exist. A room that isn't priced for people who already have the runway. A place where the person with $37 in their account and fifteen years of experience and a real idea can come and learn to build their way into a different situation. Not a YouTube channel. Not a bootcamp. A room with someone in it who has been in both places and knows the difference.
I’m building that room. If you want to be inside of it, I want to hear from you.
When ChatGPT first emerged in 2022, some of us saw this as technology’s opportunity for AI to be the great equalizer. The tool that would finally make credentials matter less, not more.
You didn’t need to be a developer to build a working app. You didn’t need a degree from Stanford or Sand Hill Road connections to build something real and get it in front of the right people.
I believed it, too. And last year, along with many others, I got to work and started down a path of building an imaginative AI-powered learning companion for my kids. But about six months in, reality hit: I ran out of money, which meant really that I ran out of time to keep poking at this problem for long enough to make it work.
Rather than scrap it all for full-time employment, I pivoted. I recognized that even though I couldn’t take my own ideas across the finish line, I could help other people like me get theirs there, too. So I started offering to teach back what I’d learned.
Like a lot of people, I learned pretty quickly that there’s a lot more money in corporate workshops than in one-off individual sessions where you have to fight to earn every new recruit.
From the outside, I look like I’ve already made it. But the reality is that I’ve never felt more cash-constrained in my entire career. And I’m not alone. Over the past 18 months I’ve watched dozens of smart, capable friends opt out entirely. Not because they failed, but because waiting has a cost that eventually becomes too high.
The landscape is falling into place as naturally as ever before. Corporate training programs with five-figure price tags. Enterprise licenses sold to companies who were already winning. Bootcamps priced at $3,000. Not exactly the actualization of that idealistic “AI for anyone” dream. What we’re seeing instead is a mirroring effect from what we saw during the last digital revolution: The people who already have the resources and the runway to experiment get there first. Larger firms are investing more than smaller shops. So the money (and the resources, and the talent) follows suit. Nobody is incentivized to build for everyone else.
The person nobody built for isn’t hard to describe. She’s making $60k and trying to go independent but can’t afford to stop her salary long enough to find out if it works. He’s been in the industry for fifteen years but his resume doesn’t have the right logos on it so the warm intros don’t come. She’s already running her own business, found out about AI on her own, taught herself the basics on YouTube, but then got stuck. She knows she could be building something real with it. But she has no room, no cohort, no one standing in front of her saying, “Here. Click this now. Try it this way instead.”
Corporate boards are pushing AI upskilling through every department. Individual coaching clients with the financial means to take learning into their own hands are inviting me into their home offices once a week to work through the basics of ChatGPT, Gemini, and Claude.
It feels good to have enough in the bank to afford my own life. But I can’t stop noticing who I’m not serving.
My clients today aren’t people whose entire financial arc could change because of AI. These are the people who already have the funding, the resources, and the runway to treat learning as an investment. They were going to be fine before I showed up. They’ll be fine after.
Meanwhile the people who actually need this — the ones standing on a dance floor with $37 in their account, the ones one bad month away from stepping back entirely — still can’t afford to hire me.
At my current pace, I’m on track to 5-6x my revenue from last year. But I’ve already rebuilt the exact hamster wheel I was trying to escape. Different clients, same problem. The people with budgets get the room. Everyone else gets a YouTube video.
Which leaves me with one question: What about everyone else?
I don’t have a clean solution yet. I know what needs to exist. A room that isn't priced for people who already have the runway. A place where the person with $37 in their account and fifteen years of experience and a real idea can come and learn to build their way into a different situation. Not a YouTube channel. Not a bootcamp. A room with someone in it who has been in both places and knows the difference.
I’m building that room. If you want to be inside of it, I want to hear from you.
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