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
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More of my friends than ever before are choosing to go independent in their careers. Maybe you’re fed up with corporate culture and are officially splintering off from the 9-5. Maybe you were recently laid off but you’ve decided to consult vs. jump into the next full-time job. Or maybe you’ve tasted what’s possible with AI no-code building, an now you’re opting to make something from scratch yourself.
This is undeniably my favorite thing happening amidst this time of serious political, economic, and social upheaval. But even with these mass movement indicators on our side, it still doesn’t change the reality: It’s hard to start things.
I’ve been watching and helping people start things for most of my career. But I didn’t fully commit to the bit myself until a few years back – first, with fractional work, then with community work, and now with entrepreneurship.
Since I started making (and sunsetting) apps last year, then building a brand ethos around Build First, I’ve learned a lot of things from the ground floor of season one of founder mode. I hope many more people go down this path, as it’s what I believe will contribute toward a changing texture of leadership that the world desperately needs right now. So today I wanted to take the time to share a few reflections in case you’re considering going this route, too.
Here are ten things I wish I knew about starting things.
There’s a moment as a parent where you move your kid from the fully contained “crib mode” (ie: 4 walls up, no exit or escape without help) to “big kid bed mode.” In big kid bed mode, your kid has full domain over their bed and their room, which means they can get out of bed and then return back to it independently. But there’s a period of time — and it’s different for every kid — when suddenly a light bulb moment goes on and the kid realizes,
More of my friends than ever before are choosing to go independent in their careers. Maybe you’re fed up with corporate culture and are officially splintering off from the 9-5. Maybe you were recently laid off but you’ve decided to consult vs. jump into the next full-time job. Or maybe you’ve tasted what’s possible with AI no-code building, an now you’re opting to make something from scratch yourself.
This is undeniably my favorite thing happening amidst this time of serious political, economic, and social upheaval. But even with these mass movement indicators on our side, it still doesn’t change the reality: It’s hard to start things.
I’ve been watching and helping people start things for most of my career. But I didn’t fully commit to the bit myself until a few years back – first, with fractional work, then with community work, and now with entrepreneurship.
Since I started making (and sunsetting) apps last year, then building a brand ethos around Build First, I’ve learned a lot of things from the ground floor of season one of founder mode. I hope many more people go down this path, as it’s what I believe will contribute toward a changing texture of leadership that the world desperately needs right now. So today I wanted to take the time to share a few reflections in case you’re considering going this route, too.
Here are ten things I wish I knew about starting things.
There’s a moment as a parent where you move your kid from the fully contained “crib mode” (ie: 4 walls up, no exit or escape without help) to “big kid bed mode.” In big kid bed mode, your kid has full domain over their bed and their room, which means they can get out of bed and then return back to it independently. But there’s a period of time — and it’s different for every kid — when suddenly a light bulb moment goes on and the kid realizes,
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
Share Dialog
You Can Just Start Things Ten reflections from the ground floor of Season One of "founder mode" https://hardmodefirst.xyz/you-can-just-start-things
Depending how deeply ingrained your prior work culture had been, this powerful paradigm shift takes time to fully internalize. But it’s a critical first step toward feeling enough agency and confidence to actually succeed.
The first thing I decided to start (and name, which is important to do for a lot of reasons) was The Manhattan 75 block association. This was confusing to a lot of people. (“It’s not a company, it’s not a business, it’s not tech. What’s the point?”) But the truth is that I knew I needed to feel grounded in a community that outlived whatever transience existed at work. Doing the startup process in another community first also gave me a very helpful blueprint for how to read and interpret signals in other contexts. As it turns out, starting an AI-first company isn’t straightforward, either, so this was a great practice round for me.
I wish I could give you more advice on how to decide what thing doesn’t make sense (for real) vs. what thing just doesn’t make sense (for now). But I think the only thing to do is ask yourself, “Does this make sense to me?” And if it truly and honestly does (and you’re not lying to yourself about it), that’s good enough to start.
Whether you’re standing on the street corner with your own lemonade stand with your kids or sending cold DM’s on LinkedIn from your shoebox office, you have to cross a lot of bridges on your own before you get your first high-five from another human who cares. While more than ever is possible for solopreneurs these days, it doesn’t shortcut the solitary work that happens in the early days of any new idea. If you don’t know how to get yourself back to the table even after things fall apart again and again, you’ll never make it to season two.
I have a lot of ways that I keep myself motivated without someone else sharing the same physical space as me, and every one of my founder friends has their own version of this. (Gym time, bath house visits, improv on the weekends, movie marathons, or socializing with friends.) We’ve all got different needs. It’s important to find your own formula that keeps you showing up.
They say, “If you can dream it, you can achieve it.” But they don’t tell you how long it really takes. Unfortunately, I live in a chronically delusional state of reality that makes it seem like the thing I want is just within reach. I don’t think this is an unusual feeling. I’ve noticed a lot of founders share this “just around the corner” mindset, only to wear themselves out just as things are getting started (or to give up just before they reach the precipice). While a little self-delusion is essential for anyone starting up for themselves, anchoring in reality (and other real human timelines) is the only way to sustain the pace.
One really good use of advice (either from an AI or a human) is to use it to manage expectations on both process and time horizons. I like to ask people, “How long did that take?” or even watch peers who started around the same time as me track their own benchmarks of progress. And if you struggle with knowing what steps 2-8 look like on a 10-step checklist to achieving your dreams, AI is a great first place to go to break down some of the milestones that need to happen in the middle.
I’ve worked in highly autonomous roles for most of my career, so I’m no stranger to self-directed projects. But the milestones you clear on your own are very quiet and rarely celebrated externally. Even working fractionally carries some degree of closure and acknowledgement (typically, at the end of a project). But as a founder, when you’re always looking ahead to what’s next, it’s easy to forget how far you’ve already come. Whether you practice this through peer group chatter, writing out loud, or even your own celebrations for one, it’s important to witness your own leveling up.
Most of my serious founder friends have a habit of either personal or semi-public reflecting to hold themselves accountable. I started sending monthly updates to my close network and peers. The truth is that it doesn’t matter how many of them actually read it; the habit of self-benchmarking is good enough for me to keep it up.
I personally find it impossible to listen deeply to the problems I actually care about when I invite too many other people into the process in the early days. It’s hard to sit down and ask yourself what you really want to build; it’s a lot easier to ask other people what they think you should do next. This part of why taking outside capital too early is a big problem for early stage founders (and why I resisted the urge to do so). If you don’t know your own “why,” then you’ll be stuck managing the expectations and desires of your early supporters or investors, rather than figure things out for yourself.
Consider artists who take retreats to write their books, or even musicians who go dark on social media during their “studio build” weeks when creating a new album. This is a signal of what it takes to carry intrinsic motivation during those early days of creation, where you keep your ideas quieter and in a smaller circle (starting with yourself) before you expand out again.
I’ve rebranded myself enough times to know how long it takes my network to “catch up” to my current work. What I’ve noticed is that there is a lag between what people see and what’s actually happening on the ground floor. Today I use the signal from my external network not as an “end all, be all” but more as one more data point in the tea leaves of reading the market (and my place in it). And just in case anyone out there needs to hear it – even if you’re “crushing it on LinkedIn” your bank account may still need time to catch up.
A few things that help me with the public signaling are to pay closer attention to how other signal. What are they LinkedIn posts that other founders, hustlers, and solo operators are doing today, and what might that mean for the place they want their network to see them tomorrow? How can you use the public commons to write your own narrative?
Tied to the previous point, I find that excessive availability and openness is only good to a certain point. As a hyper-connector, I find it quite natural to book up my weeks with well-meaning meetings of people who “just want to catch up.” But then I get from Monday to Friday without any demonstrated progress or next steps. I’ve gotten much more aggressive on my calendar blocking and I try to move past anything on the internet (the good or the bad) as fast as I can.
It can be tempting to listen to the nice things people tell you as validation of accomplishment. But I also find that (due to the lag), if you treat any positive external signal as an excuse to take your foot off the gas, you’ll be pretty upset a few months later when the leads dry up. And the reality is, nobody knows your business better than you. Inversely, if you treat any negative signal as an indication to give up (particularly if that negative signal comes from a person who is not part of your intended buyer audience), you may stop before you’ve given yourself permission to start. Overall, it’s just a giant distraction.
I never used to understand why people said it was helpful to put up paywalls and start charging for products early on. Now I do. As it turns out, adding price tags to things is a clear way to weed out the true believers from the fair-weather fans. I wish I did this earlier, in basically every single instance. After all, if you want to start a business, you need to know what people will pay for, how much you need, and what kind of people and institutions might want to support it.
One of the biggest ways that I have changed my perception around this is to just talk about money a lot more with my peers. While initially this felt like a deeply uncomfortable discourse, I’ve notice that the people who operate at the upper echelons of economic prosperity talk about money matters all the time. So the truth is that if you do not talk about it, you are getting in your own way. Today I have a pretty good sense of what the hourly rates are for people with my level of domain expertise, what people will pay for AI trainings and small batch software today, and also how much money it takes to actually lift something off the ground.
It takes a long time to get to the starting line. Really long. But as I learned, all of that it still just season one. Season two is where the game play actually gets started. And I’m finding this year, I’m less focused on hitting a certain unrealistic threshold and more focused on staying in the game for long enough to maximize the surface area of my luck. You can’t get lucky if you don’t stick around long enough to throw out longshots. So this year for me is all about holding the line while I lob out the next set of experiments to see which one will carry me into season three. That’s how you go from starting something to sticking with it.
Depending how deeply ingrained your prior work culture had been, this powerful paradigm shift takes time to fully internalize. But it’s a critical first step toward feeling enough agency and confidence to actually succeed.
The first thing I decided to start (and name, which is important to do for a lot of reasons) was The Manhattan 75 block association. This was confusing to a lot of people. (“It’s not a company, it’s not a business, it’s not tech. What’s the point?”) But the truth is that I knew I needed to feel grounded in a community that outlived whatever transience existed at work. Doing the startup process in another community first also gave me a very helpful blueprint for how to read and interpret signals in other contexts. As it turns out, starting an AI-first company isn’t straightforward, either, so this was a great practice round for me.
I wish I could give you more advice on how to decide what thing doesn’t make sense (for real) vs. what thing just doesn’t make sense (for now). But I think the only thing to do is ask yourself, “Does this make sense to me?” And if it truly and honestly does (and you’re not lying to yourself about it), that’s good enough to start.
Whether you’re standing on the street corner with your own lemonade stand with your kids or sending cold DM’s on LinkedIn from your shoebox office, you have to cross a lot of bridges on your own before you get your first high-five from another human who cares. While more than ever is possible for solopreneurs these days, it doesn’t shortcut the solitary work that happens in the early days of any new idea. If you don’t know how to get yourself back to the table even after things fall apart again and again, you’ll never make it to season two.
I have a lot of ways that I keep myself motivated without someone else sharing the same physical space as me, and every one of my founder friends has their own version of this. (Gym time, bath house visits, improv on the weekends, movie marathons, or socializing with friends.) We’ve all got different needs. It’s important to find your own formula that keeps you showing up.
They say, “If you can dream it, you can achieve it.” But they don’t tell you how long it really takes. Unfortunately, I live in a chronically delusional state of reality that makes it seem like the thing I want is just within reach. I don’t think this is an unusual feeling. I’ve noticed a lot of founders share this “just around the corner” mindset, only to wear themselves out just as things are getting started (or to give up just before they reach the precipice). While a little self-delusion is essential for anyone starting up for themselves, anchoring in reality (and other real human timelines) is the only way to sustain the pace.
One really good use of advice (either from an AI or a human) is to use it to manage expectations on both process and time horizons. I like to ask people, “How long did that take?” or even watch peers who started around the same time as me track their own benchmarks of progress. And if you struggle with knowing what steps 2-8 look like on a 10-step checklist to achieving your dreams, AI is a great first place to go to break down some of the milestones that need to happen in the middle.
I’ve worked in highly autonomous roles for most of my career, so I’m no stranger to self-directed projects. But the milestones you clear on your own are very quiet and rarely celebrated externally. Even working fractionally carries some degree of closure and acknowledgement (typically, at the end of a project). But as a founder, when you’re always looking ahead to what’s next, it’s easy to forget how far you’ve already come. Whether you practice this through peer group chatter, writing out loud, or even your own celebrations for one, it’s important to witness your own leveling up.
Most of my serious founder friends have a habit of either personal or semi-public reflecting to hold themselves accountable. I started sending monthly updates to my close network and peers. The truth is that it doesn’t matter how many of them actually read it; the habit of self-benchmarking is good enough for me to keep it up.
I personally find it impossible to listen deeply to the problems I actually care about when I invite too many other people into the process in the early days. It’s hard to sit down and ask yourself what you really want to build; it’s a lot easier to ask other people what they think you should do next. This part of why taking outside capital too early is a big problem for early stage founders (and why I resisted the urge to do so). If you don’t know your own “why,” then you’ll be stuck managing the expectations and desires of your early supporters or investors, rather than figure things out for yourself.
Consider artists who take retreats to write their books, or even musicians who go dark on social media during their “studio build” weeks when creating a new album. This is a signal of what it takes to carry intrinsic motivation during those early days of creation, where you keep your ideas quieter and in a smaller circle (starting with yourself) before you expand out again.
I’ve rebranded myself enough times to know how long it takes my network to “catch up” to my current work. What I’ve noticed is that there is a lag between what people see and what’s actually happening on the ground floor. Today I use the signal from my external network not as an “end all, be all” but more as one more data point in the tea leaves of reading the market (and my place in it). And just in case anyone out there needs to hear it – even if you’re “crushing it on LinkedIn” your bank account may still need time to catch up.
A few things that help me with the public signaling are to pay closer attention to how other signal. What are they LinkedIn posts that other founders, hustlers, and solo operators are doing today, and what might that mean for the place they want their network to see them tomorrow? How can you use the public commons to write your own narrative?
Tied to the previous point, I find that excessive availability and openness is only good to a certain point. As a hyper-connector, I find it quite natural to book up my weeks with well-meaning meetings of people who “just want to catch up.” But then I get from Monday to Friday without any demonstrated progress or next steps. I’ve gotten much more aggressive on my calendar blocking and I try to move past anything on the internet (the good or the bad) as fast as I can.
It can be tempting to listen to the nice things people tell you as validation of accomplishment. But I also find that (due to the lag), if you treat any positive external signal as an excuse to take your foot off the gas, you’ll be pretty upset a few months later when the leads dry up. And the reality is, nobody knows your business better than you. Inversely, if you treat any negative signal as an indication to give up (particularly if that negative signal comes from a person who is not part of your intended buyer audience), you may stop before you’ve given yourself permission to start. Overall, it’s just a giant distraction.
I never used to understand why people said it was helpful to put up paywalls and start charging for products early on. Now I do. As it turns out, adding price tags to things is a clear way to weed out the true believers from the fair-weather fans. I wish I did this earlier, in basically every single instance. After all, if you want to start a business, you need to know what people will pay for, how much you need, and what kind of people and institutions might want to support it.
One of the biggest ways that I have changed my perception around this is to just talk about money a lot more with my peers. While initially this felt like a deeply uncomfortable discourse, I’ve notice that the people who operate at the upper echelons of economic prosperity talk about money matters all the time. So the truth is that if you do not talk about it, you are getting in your own way. Today I have a pretty good sense of what the hourly rates are for people with my level of domain expertise, what people will pay for AI trainings and small batch software today, and also how much money it takes to actually lift something off the ground.
It takes a long time to get to the starting line. Really long. But as I learned, all of that it still just season one. Season two is where the game play actually gets started. And I’m finding this year, I’m less focused on hitting a certain unrealistic threshold and more focused on staying in the game for long enough to maximize the surface area of my luck. You can’t get lucky if you don’t stick around long enough to throw out longshots. So this year for me is all about holding the line while I lob out the next set of experiments to see which one will carry me into season three. That’s how you go from starting something to sticking with it.
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You Can Just Start Things Ten reflections from the ground floor of Season One of "founder mode" https://hardmodefirst.xyz/you-can-just-start-things