Stefan Lindstrom has spent years studying entrepreneurs. Not the mythology but the actual behavior. He’s givens of thousands of tests and had thousands of conversations. And what he came back with is not inspiring.

It’s repetitive.

Same people succeed over and over. Same people stall over and over. He sees the same habits. The same reactions. The same blind spots.

But who succeeds and who fails? Lindstrom has an answer.

He keeps coming back to the same thing. Self-awareness. Not journaling, not vibes. Just noticing what you do when things go wrong, and being honest about why you keep doing it.

Most founders can’t do that.

They’re built to act. They see a problem, they move. That’s the whole game. But they also get attached. The idea becomes theirs. And once that happens, they stop listening.

He said it in a way that stuck. “Ideas are like children. Everyone thinks theirs is special.”

That’s where things break.

The market doesn’t care. Customers don’t care. You either adjust or you don’t. And if you don’t, you repeat the same pattern until you run out of time or money.

There’s another piece to it.

A lot of founders don’t know how to sell.

They build something real, something that works, and then they freeze when they have to explain it. Especially outside the U.S. You don’t grow up pitching. You don’t grow up selling yourself.

So you get stuck with a good product and no way to move it.

Meanwhile the market right now is a mess. Frozen in places. Nobody really knows what’s next.

That’s not a bad thing.

That’s the only time entrepreneurship works.

If everything is stable, nothing new gets built. When things shift, when the ground feels off, that’s when someone steps in and figures something out.

Entrepreneurs don’t wait for clarity. They move into the confusion and try to shape it.

That’s it.

Not vision. Not passion. Not some founder story you can package.

You notice what you’re doing. You fix what you can. You keep moving even when it feels wrong.

And sometimes, that’s enough.

I’ve been thinking a lot about who belongs on Keep Going. I’m reworking the show and am looking for a fresh crop of guests.

Keep Going has always been about what happens after things break. Not the clean version people tell later, but the moment itself, when the plan fails, when the identity you built starts to slip, when you have to decide whether to keep moving or step away.

So I’m looking for guests who can tell stories like that. For a long time I’ve worked with PR people and other folks to get folks with some sort of story. I’d like to expand into people who work as psychologists, writers, journalists, and artists. I want to expand Keep Going to contain the scope of human endeavor.

I want people with stories that still feel raw. I was founders who lost something real. I want operators who made a call that didn’t work. I want writers who hit a wall and had to rethink the work. I want anyone who has been through a stretch where things did not go the way they were supposed to, and is willing to talk about it without sanding it down.

I’m also interested in people who study or work inside these moments. Psychologists, clinicians, counselors, researchers, people trying to understand how we deal with pressure, failure, work, and change. Not abstract theory, but work that connects to how people actually live.

The format stays simple. A conversation, about a half hour, recorded remotely. No performance. No need to package the story into a lesson. Just a chance to walk through what happened, what it felt like, and what came next.

If that sounds like you, or if someone comes to mind as you read this, reach out. You can pick a spot below or respond to this email with your pitch. Hope to hear from you soon.

Book at Slot

Silverstein, CEO, describes the company as an operating system for healthcare, something employers and patients can use to manage care the way a computer runs apps. The product started in what most people think of as telemedicine, then expanded into areas like mental health, virtual primary care, ortho support, navigation, and care coordination, all packaged as a subscription so the user is not paying a new fee every time they need help.

Where Amaze is trying to draw a line is how it uses AI. Silverstein says the company has its own medical team and a national medical practice, with providers as full time employees. That setup lets them use AI mostly behind the scenes, not as a chatbot trying to replace a clinician, but as software that makes clinicians faster and better.

He gave a simple example. If a patient messages in about a rash, Amaze can prompt for a photo while the call is ringing, and he says they answer most calls in 15 or 20 seconds. Once the photo is captured, the AI can do visual pattern recognition and flag a likely match, poison ivy was his example. The patient can still wait for the clinician, ask for more info, or hang up if they already know what to do. In parallel, the clinician sees the photo and a probability score on their screen.

A second example gets at why this is not only about convenience. Silverstein described a scenario where a parent calls about a child vomiting overnight. While the clinician is asking the normal questions, the AI is transcribing, taking notes, and running a rolling diagnosis. He said the system could call out to CDC data through an open API, spot that there have been recent E. coli cases near the caller, and surface that context to the clinician in real time.

The line he kept coming back to was “meeting patients where they are.” Some people want a human every time. Some people want a fast answer and a safety net. Silverstein’s view is that a hybrid system can let the patient choose the pace, while still keeping a real clinician in the loop.

He also talked about public health signal. Amaze is not trying to train new medical models from scratch. He says the company is still relatively small in data terms, with a little over 100,000 patients, and he does not think it would be responsible to claim they are “improving medicine” through training at that scale. But he does think they can spot patterns faster than traditional reporting loops. He described seeing COVID flare ups in near real time because of concentrated employer use in Phoenix, then checking later and seeing the same spikes reflected in CDC reporting after a delay.

On the product side, he says they already use AI to generate provider notes and to evaluate patient sentiment, including whether a patient sounds receptive to instructions. He also mentioned using AI to score a “patient activation measure,” a way to estimate a patient’s knowledge, skill, and confidence in managing their own care, and then use that to tailor how clinicians communicate on future calls.

Silverstein’s bet is that healthcare will get more technical under the hood and more relationship driven on the surface. In his view, AI will keep getting better at complex diagnosis, but patients will still need a trusted partner to help them decide what to do next, where to go, and how to pay for it as the system gets more confusing.

I’ll be holding an in-person mixer at Red Lion in Manhattan on Wednesday, May 6 at 7pm. This will be a getting-to-know-you meetup without a formal agenda, just a few drinks and lots of chats. If you’re interested in AI, AI video, AI video ethics, or AI video production, I think this will be a great way to get up to speed and start some interesting conversations.

RSVP

You can RSVP here on Meetup and please consider joining our group so we can grow and network.

From the outside, it looks clean. Comedy group, Sundance film, books, writing for TV. A straight line. But it isn’t.

“Our life is composed of days,” he told me. “And this is one of them.”

That’s the job. Not the career. The day.

Because most of the time, it’s not the dream. It’s the gap between dreams.

DC spent the last year working in social media advertising. Not because he wanted to pivot. Because the work slowed down. Because strikes happened. Because the industry does what it always does, it dries up and then floods again.

“It was challenging to my identity as a creative person,” he said. “But then it was also cool… and I was grateful for it because it’s a job and it allows you to be alive.”

That’s the truth nobody puts in the highlight reel.

You don’t “make it.” You stitch it together.

You jump from one thing to the next. You write jokes for someone else all day, then try to find enough energy at night to write something for yourself. You take the corporate gig, then try not to let it eat the part of you that wanted this life in the first place.

And most of the time, it almost does.

The only thing that saved him was simple. Another person.

Someone else in the same situation. Same background. Same problem.

“We would kind of be accountability partners… I’d say I’m gonna write this thing this weekend… and then I’d come back and say, I did it.”

Not a system. Not a course. Not a master plan.

Just two people refusing to let the work die.

That theme came up again when we talked about how he started. It wasn’t strategy. It was proximity.

Five people. One group. Each doing a different thing well enough to make something real.

“We had… the ability… to go and make sketches that looked better than a lot of stuff that was out there at the time.”

Not because they were perfect. Because they were there.

This is the part people miss now. Especially with AI sitting there, ready to do everything faster.

You can generate the thing. You can fake the output. You can make something that looks right.

But you lose the reason you started.

“I would rather come up with ten dumb toilet puns… that nobody’s ever going to notice… and be like, I did every single one of those.”

It’s the quiet satisfaction that you made the thing yourself, even if no one sees it.

We talked about AI, and he didn’t panic. He didn’t celebrate it either.

He just called it what it is.

“Plausible.”

It looks right. It feels right. It passes at a glance.

But it doesn’t hold up.

And more importantly, it doesn’t carry the weight of a real life behind it.

“A server farm can’t do that,” he said, talking about the weird, difficult experiences people put into their work.

That’s the bet now.

Not that AI disappears. It won’t.

But that the connection between a person and the thing they made still matters.

Even if it gets harder to make money. Even if the pipeline gets worse. Even if everything gets noisier.

Because the alternative is easy.

Too easy.

And easy work rarely means anything.

At the end, I asked him where this is all going. Where media goes. Where attention goes.

He didn’t pretend to know.

But he said something I keep thinking about.

“There are things fomenting that we don’t even know what they are… it’s probably already happening, and the algorithm is not picking up on it.”

That’s where the next thing is.

Not in the feed. Not in the obvious place.

Somewhere small. Somewhere ignored. Somewhere real.

And if you’re paying attention, you’ll find it.

Or better, you’ll build it.

Thier is a writer, director, and the founding director of the Independent Film School, which now has something like 65,000 members. The strange part is how it began. She could not get a job. She applied for a dog-walking job and did not get that either. So she did what a lot of people do when the normal routes close up. She made her own opening. She announced that she was starting a screenwriting class. Two people signed up. One of them wanted a discount. So she made the first class free, twenty people showed up, eight stayed for the full course, and the thing took on a life of its own.

That story sounds neat when you tell it fast, but what I liked about her version is that she does not pretend she had some polished strategy from the start. She was trying things. She was paying attention. She was making changes. Now people would call it a lead magnet and act like it was all part of a system, but back then it was just common sense. Let people see what you can do. Let them decide if they want more.

There is a lesson in that which has nothing to do with film school and everything to do with work. A lot of people wait for permission, or for the market to confirm them before they begin. Thier did the opposite. She put something in the world, saw what happened, and kept moving. That is a better way to build almost anything.

The phrase she kept coming back to was “follow the fun,” which could sound soft if it came from somebody less serious. From her it did not. She meant it as a discipline. She meant that when the work stops feeling alive, you should pay attention, even if the safer move is to keep grinding in the same format. She said she has changed things at the school in ways that cost her students and forced her to rebuild. The biggest break came when she moved from in-person teaching to online teaching. Most of the old students vanished. She had to start over. But the move let the school grow in a way it never could have otherwise.

That is the hard part of following what feels alive. It is not comfort. It is risk. Adults forget that. Kids do not need to be taught how to enjoy making things. They do it by default. Then school, work, status, and all the usual junk come in and flatten that instinct into a set of measurements. Thier’s point was that the chase for success and fear of failure can pull you away from the work that actually matters to you. For artists that is deadly. It is probably bad for everyone else too.

She was also blunt about money, which I appreciated. When I asked how an artist makes enough to survive, she did not romanticize it. She said you get a job. That was her answer. Being an artist, in her telling, is a labor of love, not a reliable business model. If some money comes from the art, good. But counting on that is like building your life around a winning lottery ticket. Better to separate the two goals. One is keeping the lights on. The other is making the work you need to make. Once you jam those together, you often fail at both.

That answer matters because too much advice around creativity is built on fantasy. We tell people to monetize their passion, build their brand, scale their gifts, and all the rest of it. Most of the time that just means turning the thing you love into another machine for stress. Thier has a more useful view. Protect the work first. Protect your ability to do it. Get honest about the economics. Then keep going.

At the same time, she does not draw a hard line between art and business. She said that when she moved the school online and had to learn marketing, course-building, team management, and sales, she found that process deeply creative too. She treated it like making something, not like taking a day job away from her real work. That is probably why she got through it. She was not just doing admin. She was building a structure that could hold the rest of her life up.

Still, there was a cost. For a few years, she had to put filmmaking aside and put her energy into the school. That tradeoff was not theoretical. It took real time away from the work she most wanted to do. But the payoff came later. The school made it possible for her to direct another film, one starring J.K. Simmons, which she is releasing this year. That is the kind of delayed return most people hate because it takes too long and gives you no guarantee. It is also, very often, the only kind that counts.

One of the strongest parts of the conversation came when she talked about her film Tomorrow Ever After. By her account it did everything an independent filmmaker could ask once audiences actually saw it. It got standing ovations. It won awards. It had a perfect Rotten Tomatoes score during its run. And yet it still could not get proper distribution. She told me about meeting with an executive at Sony Pictures Classics who said they loved the film and could not buy it. It was not at Sundance. It had no known actors. They could not sell it.

That, she said, was when she became a grownup.

It is a hard line, but an honest one. She realized that if you want to beat the game, sometimes you have to pretend to play it. So the next films got built with financeable actors attached. That was not the death of her principles. It was an adjustment to reality. There is a difference. Artists hate that distinction because it feels like compromise, and sometimes it is. But there is also a point where refusing the rules just means nobody sees the work. That can become its own kind of vanity.

I asked her why she stays in New York when it is expensive and hard and increasingly absurd in all the normal ways. Her answer had nothing to do with career. It was about people. Family in Brooklyn. Her nephew. The relationships that make a life feel real. She said those are the safest investment we have. I think she is right. A lot of people make decisions about where to live or what to build based on some abstract idea of winning. Thier’s view is more grounded than that. Stay near the people who make you yourself.

By the end of the interview it was clear that her school is not some side project that got out of hand. It is part of the same body of work. She cares about her students. She would like to coach all of them herself, but the thing is too large now, so she coaches the coaches and keeps the system going that way. She also argues, correctly I think, that her students are better served when she keeps making films. If she stopped doing the work, her advice would go stale.

She has a book coming out in May called How to Fail as an Artist: My Best Tips, which is the exact kind of title I like because it does not pretend the road is clean. She described it as a memoir, but also as a pep talk for artists who have given up, or are about to, which probably means most artists at one point or another.

That is what this whole conversation was really about. Not failure as branding. Not failure as a cute origin story. Failure as the weather you work in if you care about making something real. Thier’s answer is not to deny that. It is to build a life sturdy enough to keep working anyway, keep teaching anyway, keep making films anyway, and keep some part of the whole thing joyful enough that you do not turn into a dead machine while doing it.

You get a message saying you missed an appointment. It points you to a booking page. The name looks normal, the flow looks normal. You click through, pick a time, go through the usual steps. Nothing stands out.

Then it asks you to get ready for the meeting.

There is a download for Windows, which is expected. Then there is a “download” for macOS. That is where things change. Instead of a file, you get a terminal command. A curl command. It tells you to paste it into your terminal. If you’re not technical, this step can inject so much malware into your system that you’ll probably be hacked for life.

That should stop you right there.

The command points to a domain that looks real at a glance but is not. The domain was created recently. Same with the app domain tied to the booking flow. Both showed up within the past month or so.

I started poking around. The site has all the usual pages: Pricing, About, Blog, Careers, Contact. Every single one is dead. Links go nowhere. Social links are junk. It is a full layout with no substance behind it.

I tried to pull the file without running it, just to see what it was doing. Even that failed. The endpoint is already gone. Whatever was there has been taken down or moved.

So what is the point?

The point is to get you to run a command you do not understand. If you paste that into your terminal and hit enter, you are giving it permission to do whatever it wants on your machine. Download code, run it, install something, pull data, anything.

Most people are not used to seeing terminal commands in a normal workflow, but the setup here is convincing enough that someone might go along with it. It looks like a meeting tool. It feels like onboarding. You are already halfway committed by the time you see the command.

That is the trick.

If you take one thing from this, it is simple: Do not paste random commands into your terminal. Ever. It does not matter how official the site looks or how normal the flow feels. If you do not know exactly what a command does, do not run it.

Also, we know that hackers are targeting the desperate. There are endless crypto scams out there, and this one targets job seekers who are already probably exhausted. Please be careful any time someone asks you to use anything outside of Zoom, Calendly, or Google Meet. Also, make sure you never, ever download weird apps to connect to any kind of video meeting.

This one is already dead, but there will be more.

Mascia came out of Wall Street and landed in the one place he never wanted to be, his family’s Dunkin’ Donuts and Baskin-Robbins business in New Jersey. After 9/11 and a series of health problems in his family, he stepped in because his parents needed help and because, in his words, family came first. Over nine years they grew the business from 20 locations to 40, which sounds like success until you look at the cost. He was underpaid, frustrated, and stuck inside a structure that ran on old rules, unclear expectations, and the kind of family tension that never stays in the office.

That is really the center of his story. Family businesses are rarely just businesses. They are full of old slights, private assumptions, and power struggles that started long before anyone talked about margins or strategy. Mascia said the biggest failures in his own experience were communication and transparency. Everybody had expectations, but nobody actually said them out loud. He assumed he would eventually take over. His father assumed he would hand over more responsibility when the time felt right. Other relatives had their own ideas. None of that added up to a plan.

What I liked about Bobby’s take is that he does not dress this up as some clean business lesson. He talks about resentment, confusion, and the weird emotional math of trying to be a son, an operator, and a future owner at the same time. He gave a good example during the interview about how family members in business often switch roles in the middle of an argument without even noticing it. One minute you are talking as CEO and CMO, then suddenly you are talking as siblings, then as equal owners, then as two people reliving something from twenty years ago. Once that happens, the actual issue is gone. You are no longer solving a business problem. You are fighting over identity.

That part felt useful well beyond family business. A lot of people build companies with friends, spouses, or long-time collaborators, and the same confusion creeps in. If you do not know what role each person is playing in a given conversation, then every disagreement becomes personal. Mascia’s answer is simple enough to sound obvious, but most people never do it. Name the role. Name the conversation. Stay inside it. If you need to have a different conversation, have it later.

The other part of his story that stayed with me was what happened when he finally left. He started over in finance, built Green Ridge Wealth Planning from scratch, and spent a year barely speaking to his father. That split sounds brutal, and it was, but it also gave him the space to figure out who he was without the family machine around him. He did not leave with a pile of money. He left with a wife who told him he looked miserable and needed to do something that felt like his own life. That may have been the smartest advice in the whole interview.

There is a common lie in family business, and probably in life in general, that staying is always the noble move. Sometimes staying is just fear with a respectable face. Sometimes leaving is the only honest act left. That does not mean leaving is clean or painless, and it certainly does not mean everyone will thank you for it. In Mascia’s case, success only changed the conversation later, once his father could see that walking away was not a tantrum or a mistake. It was a real choice.

We also talked about AI, which could have turned into the usual stale debate about which jobs are doomed, but Mascia had a more grounded answer than most. He thinks people who hide from AI are making a mistake, but he also thinks the businesses that will hold up best are the ones where human judgment still matters and where people still need to sit across from another person and work through hard decisions. In his world, wealth management is not just portfolio construction. It is helping people through conflict, grief, risk, inheritance, and fear. Those are not spreadsheet problems. Those are human problems.

That led into one of the better lines of the conversation, which was not really a line so much as a theme. Hard skills still matter because you need to know when the machine is wrong, but soft skills are going to matter more than people expect. Communication matters. Presence matters. Being able to understand what someone means when they are scared matters. If you cannot do that, then all the automation in the world is just faster confusion.

Mascia wrote a book called Unchained, and unlike a lot of business books, it came out of something real. He said he had no interest in writing the same recycled advice everybody has already heard a hundred times. What pushed him to write was not some urge to build a personal brand. It was the sense that his story might actually help somebody who was stuck in the same kind of trap, caught between loyalty and ambition, between what the family wants and what a life requires.

That is the part that makes this episode worth hearing. It is not really about succession planning, although that is in there. It is not just about entrepreneurship, either. It is about what happens when the thing you are supposed to inherit is also the thing that is holding you in place. It is about the cost of not saying what you want. It is about how many people spend years trying to be good sons or daughters when they should be trying to become themselves.

For all the talk about hustle and grit, this was a conversation about boundaries, and that feels a lot more useful right now. Not every good opportunity is your opportunity. Not every family duty has to become your whole identity. Sometimes the best thing you can do for the people you love is stop pretending you can live the life they picked for you.

Hi,

A quick reminder to the Keep Going community.

I’m trying to return to journalism full time, both here and at Resilience. That means I need paying readers. I have a family to support and a small dog named Nina who eats more than you’d think.

Here is the reality.

Startup journalism is collapsing. Reporters are leaving the field. Most coverage has turned i…

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A bearded man with a thick accent sits in a podcast studio. An earnest, British interviewer sits across from him. He asks a simple question: what will happen to AI in 2027?

The expert’s response? Based on “prediction markets” and comments by “tops of labs,” artificial general intelligence and robotics will combine to create 99% unemployment. Humans will …

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She came up in construction, which is not a forgiving place. Long hours, constant pressure, and a culture that rewards output above everything else. She learned to operate in that mode early. Work harder than everyone else. Push through anything. Do not stop to think about how you feel because that slows you down. That approach got her success in the way most people define it. Money, stability, control. But it also trained her to ignore anything that did not fit into that system.

Then her sister died, suddenly and without warning, and that kind of loss does not fit into a system built on control. It breaks it. What followed was not some dramatic collapse. It was something more common and more dangerous. She kept going, but she started numbing herself to get through it. Work during the day, drinking at night, and repeating that cycle until it became normal. Not chaos, just a steady flattening of everything that mattered.

She described it in a way that is hard to ignore. You are not living your life at that point, you are anesthetizing it. You remove the parts that hurt, but you also remove the parts that make anything feel real. The problem is that it works, at least for a while. That is why people stay there.

What changed for her was not some sudden moment of clarity. It was exhaustion with the pattern. She got to a place where she could not look at herself and feel any sense of pride. That is a low bar, but it is a real one. When you cross that line, something has to give.

She went to rehab. She doubled down on therapy. She started doing things that sound simple and are anything but simple when you are used to avoiding yourself. Writing things down. Sitting without distractions. Paying attention to where her time and energy were actually going. Not where she thought they were going, but where they really went when she looked at it honestly.

One of the sharper points she made is that energy is the only resource that really matters. Everyone talks about time, but time is not the issue. Energy is. You can spend hours doing something and feel fine, or you can spend twenty minutes on something that drains you completely. Most people never track that. They just move from one habit to another and assume it is all the same.

She started treating energy like something that had to be accounted for. What gives it back. What takes it away. What is neutral. Once you see that clearly, you start to realize how much of your life is built around habits that do nothing for you. Endless scrolling. Drinking. Overworking. All of it framed as necessary, but none of it actually helping.

There is a hard part here that she did not soften. You have to be honest about what you are doing. Not in a vague way, but in a direct way. If you spend three hours a day on your phone, you write that down. If you drink every night, you admit what that is doing, not what you tell yourself it is doing. Most people avoid that step because it is uncomfortable, but without it nothing changes.

She also pushed back on the idea that people do not have time to fix any of this. That excuse falls apart the second you look at how your day is actually spent. There is time, it is just not being used well. That is not a moral judgment, it is just a fact.

What I found interesting is that she did not replace one extreme with another. She still works. She still builds things. The difference is that it is not coming from the same place. Before, work was part of the numbing. Now it is something she chooses with intent. That sounds small, but it changes everything.

There is also a broader point here about how people define success. She followed the standard path for decades. The house, the cars, the outward signs that you have made it. When she got there, it did not deliver what it promised. That is not a new story, but it is one that people keep ignoring because the alternative requires more thought and more responsibility.

The question she kept coming back to is simple and uncomfortable. What are you using to avoid your own life. Not what are you doing to relax, not what are you doing to unwind, but what are you using to not feel what is actually going on. If you answer that honestly, you start to see the structure you are living in.

Most people sense that something is off at some point. They have that moment where they think there has to be more than this. The usual move is to ignore it and keep going. What Anne did was stop and follow that thought instead of pushing it away.

There is nothing clean or easy about that process. It is slow and it forces you to deal with things you have been avoiding for years. But the alternative is to stay in a loop that never changes.

The takeaway is not some neat system or set of rules. It is more basic than that. Pay attention to what you are doing. Be honest about why you are doing it. Then start making changes, even small ones, based on what you see. Most people never get past the first step.

She did, and that is the whole difference.

He is the CEO of Grail, a company building AI tools for scientists, but the real story is not the tool. It is the problem he thinks science has become.

Kejriwal trained as a computer scientist, earned his PhD at UT Austin, and went on to teach at USC. He stayed in academia long enough to see a pattern that bothered him. Scientists were spending too much time writing, formatting, and packaging their work, and not enough time thinking. The tools were not helping. The incentives were not helping either.

So he left and built something himself.

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That was one of the clearest lessons from my conversation with Melissa Hanna, the co-founder and CEO of Mahmee, a company that provides prenatal and postpartum support through doulas, lactation consultants, nurses, mental health providers, and nutritionists. The services are bundled together and, in many cases, covered by insurance. The support begins during pregnancy and continues through a child’s first year.

At first glance, Mahmee sounds like a healthcare startup built around coordination. In one sense it is. But Hanna’s story is really about something harder. She started with the belief, common in startups, that a broken system could be fixed by better software. Over time she found that software mattered, but it was not the thing standing in the way.

The original problem that pulled her in was simple and disturbing. The United States has some of the worst maternal and infant health outcomes in the developed world. For Black women, the numbers are far worse. Hanna said Black women face maternal mortality rates three to four times higher than peers with similar clinical and economic profiles who are not Black. Native American and Indigenous women also face sharply elevated risks. These are not small gaps at the margins. They are structural failures.

Hanna began by treating the issue as a data and communications problem. Why were patients falling through the cracks. Why were providers not sharing information. Why were systems not talking to one another. Those are reasonable questions, especially in American healthcare, where fragmentation is a defining feature. Patients move between doctors’ offices, hospitals, insurers, specialists, and community providers, often with little continuity between them.

So Mahmee’s first life was as a software company. For roughly five years, the company built tools to connect providers and surface information that was not being captured elsewhere. Hanna and her team focused on the providers who often sit outside the formal medical stack, doulas, lactation consultants, nutritionists, nurses, and mental health professionals working in communities, private practices, or local nonprofits.

Those providers often knew a great deal about what was happening with a patient. A doula might hear details a patient never shares with an OB-GYN. A lactation consultant might see warning signs that never make it into a medical record. A mental health provider might understand a patient’s risk in ways that do not show up in a standard clinical workflow. But much of that information was effectively invisible to the larger system.

Mahmee built software to change that. The company created electronic health record tools, care management systems, communications features, and scheduling and billing software aimed at these community based providers. In doing so, it found real demand. Thousands of providers signed up across 44 states. The footprint was broad. The product was useful.

But scale did not follow.

That was the hard part. Each provider might only serve dozens, or perhaps a hundred, clients a year. The software worked, but the market around it was too small and too fragmented to produce the kind of reach Hanna believed was necessary. She used an analogy from The Founder, the film about Ray Kroc and McDonald’s. You can have a very good milkshake machine, but if the burger stands are too small to use it at scale, the machine alone does not solve the problem.

That was the pivot.

Hanna realized the real barrier was not simply that community based maternal health providers lacked software. It was that they lacked a place inside the formal healthcare economy. Insurance often did not cover their services. Payment models were broken. The people who were often best positioned to support mothers before, during, and after birth were sitting outside the system that paid for care.

At that point Mahmee stopped being a pure software company. It became a tech-enabled healthcare services provider. Instead of just selling tools to doulas and lactation consultants, the company employed them and built a coordinated care organization around them. The software remained important, but it became infrastructure for a services model rather than the product itself.

This is a more interesting kind of startup story because it runs against a habit in tech. Founders often want the clean answer. There is a messy industry, and software will organize it. Hanna found that the mess was deeper than that. The system was fragmented not just technically, but financially and institutionally. Data could not solve a funding problem. A dashboard could not make insurers reimburse the people who were doing essential work.

That matters because maternal care is not a niche. Hanna put maternal and infant healthcare in the United States at roughly a $200 billion market. Yet for something that large and consequential, the experience is often poor, costly, and isolating. Many women move through pregnancy and birth without enough support, without clear information, and without much sense of agency over what is happening to them.

One of the strongest parts of our conversation came when Hanna described a patient story that made this concrete. The woman was in her early twenties, already had one child, and lived in a rural area with limited hospital and doctor access. During her first pregnancy, she felt judged throughout the process. She was young, a woman of color, and she came away from the experience feeling that she had no control. Labor was difficult. The care felt harsh. She was in pain, asked for help, and felt talked down to rather than supported.

When she became pregnant again, she was afraid. She wanted the baby, but did not want to relive the first experience.

Through Mahmee, she learned something basic that had been missing the first time. She had choices. She could ask questions. She could slow a conversation down. She could say no. She could ask about pain management options beyond the narrow set that had been presented to her before. She could participate in the process rather than just endure it.

That may not sound radical, but in practice it often is. The modern medical system moves quickly, especially in high stress environments like labor and delivery. If a patient is not informed and supported, decisions get made around her rather than with her. Hanna’s point was not that doctors and nurses do not matter. Quite the opposite. In high risk pregnancies, they matter enormously. Her point was that support, education, and continuity of care change the experience and often the outcome.

This is also where her critique of the system is most useful. She does not reduce everything to one cause. Systemic racism and bias, she said, are real and they amplify disparities. But she also pointed to two other drivers, fragmentation and the chronic underfunding of preventive care. If support is only available at moments of crisis, then people will continue to arrive at those moments without the preparation, context, and trust they need.

Hanna also spoke frankly about the difficulty of funding a company in this area. Building in healthcare is hard. Building in women’s healthcare is harder. Raising venture money for maternal health can mean explaining the problem to investors who have never had to think about it in concrete terms. Part of the job, she said, was reframing the opportunity so people could understand it as both a human problem and a business one. Another part was finding investors for whom the issue already felt personal, because they or someone close to them had been through a birth experience that was worse than it should have been.

What stayed with me most was the shape of the lesson. The original thesis was not wrong. Technology does matter. Mahmee still builds software. It still uses connected tools and remote monitoring. It is now looking at how AI might fit into care delivery. But the mature version of the thesis is more grounded. Better care does not come from software alone. It comes from software plus people, software plus payment systems, software plus trust, software plus someone who is actually there when a patient needs help.

That is not as neat as a pure software story. It is more true.

There is a tendency in startups to assume that every broken institution is waiting for the right app. Sometimes what is actually missing is a workforce, a reimbursement model, and a way to bring overlooked people into the center of the system. Mahmee’s story is about discovering that the missing layer in maternal care was not just information. It was support that had been treated as optional, informal, or outside the reimbursable core of medicine.

Hanna’s company now tries to make that support part of the default package rather than a luxury add-on. The goal is not only to improve outcomes, though that is clearly part of it. It is also to change what pregnancy and postpartum care feel like for the person going through it.

That may be the real measure here. Not whether a startup found product-market fit in the usual sense, but whether it found a way to make a system less cold, less fragmented, and less likely to fail people at a moment when failure carries enormous cost.

—

Transcript

John Biggs (00:00.161)

Welcome back to Keep Going, podcast about success and failure. I’m John Biggs. Today on the show, we Melissa Hanna. She’s the CEO and co-founder of Mahmee M-A-H-M-E-E, which is a fascinating startup. You guys work with doulas and you work with care during birth, right? So why don’t you tell me about that? Welcome.

Melissa Hanna (00:30.561)

Thanks, yes. Well, Mahmee provides wrap-around prenatal and postpartum support. We do that with a team of doulas, lactation consultants, registered nurses, mental health providers, and nutritionists. And it’s all included in one bundle.

that’s actually covered by insurance. In most cases, we work with most major insurance companies and the services start during pregnancy, go all the way through labor and delivery and until baby’s first birthday. So it’s a pretty comprehensive package of support for new and expecting parents.

John Biggs (01:05.006)

So I mean, just tell me why you started this. What was the impetus?

Melissa Hanna (01:09.909)

Well, the business has been through a number of evolutions, but the impetus and the vision and mission have stayed true and consistent all the way through. We’re on a mission to make the US the best place in the world to give birth. Right now, the US is not close to having that title. So it’s a big, hairy, audacious goal, you could say, that we’ve taken on. We’re not doing it alone.

John Biggs (01:30.21)

Mm-hmm.

Melissa Hanna (01:36.705)

There are a of folks that are really passionate about this space. We work with a number of different health system and health plan partners and doctors, researchers across the country, and of course, a broad network of providers. But I started the business because I was hearing a lot about maternal and infant health statistics, the morbidity and the mortality rates in the United States.

And I kept hearing numbers that just felt very wrong, like they could not be correct. The US is in last place with the worst maternal mortality and also an egregiously high infant mortality rate compared with all other developed first world, wealthy nations, however you want to describe that. We have the best tech, the best know-how, the most passion for providing health care to a diverse population. If you look at

you know, just what the United States looks like and the resources we have to provide care to people and to hear that moms and babies are being failed every day across the country was really shocking to me. And I thought that just can’t be right. The more that I dug into it, the more I realized there was a real structural challenge in solving this. And it became more and more interesting to me. And I started pursuing it as a software problem, as a data problem.

Could we connect the dots together to figure out why people are falling through the cracks of the system? Why systems aren’t talking to each other? Why providers aren’t talking to each other? Is this a communications issue? What kind of software tool set could help provide a better experience both for the patients and the providers working in this space? And then learned over time that that was not actually going to be the answer. And therein lies the story of a pivot.

John Biggs (03:22.892)

Mm-hmm.

John Biggs (03:26.284)

Okay. And so, and this is especially egregious here in the States for the people of color as well, right? I think I interviewed someone years ago about women’s health and she pointed out that that was just abysmal.

Melissa Hanna (03:32.491)

Yeah.

Melissa Hanna (03:40.223)

Yeah, it is, it’s true. Black women have an on average rate of three to four times a higher rate of maternal mortality of death during or shortly after childbirth. this, and that’s just the average. There are some communities where it is much higher than that compared with peers with similar clinical profiles, similar economic profiles that are not black.

And so, and that’s the case also for Native American and indigenous women as well. So these two populations really are off the charts in terms of mortality rates and morbidity rates, which is the rate of injury where there could be a near death situation or sort of a near miss where something could have gone wrong and luckily didn’t happen, but there still was an injury that occurred. In all of these cases, it’s really hard to talk about

these stats without talking about systemic racism and bias in healthcare. That is a root cause of these disparities in care. What I found in doing this research over several years as I was building the tech company that Mahmee started as was that there were a number of different contributing factors and that systemic racism and bias was an amplifier. ultimately, high fragmentation, excuse me,

high fragmentation and really a lack of proactive care, just like the dollars not being allocated to preventative care, the way that we need them to be, were two of the other major drivers of this. So I started looking at this from the standpoint of, how do you solve for fragmentation? You start to think about information superhighways and information exchanges and connecting.

systems together, even if you can’t necessarily connect the institutions together. And then when it comes to dollars being allocated toward more effective solutions, you think about payment innovation in healthcare and how do you actually redirect funding toward the solutions that have the greatest impact on the community.

John Biggs (05:54.19)

So I think this is a really interesting point. mean, what you said, and I want to hear about this pivot very specifically. The language that you used before for the first iteration was kind of the language that I hear all the time from like entrepreneur who wants to do something in like, don’t know, STEM toys or education. And it’s very much like, can do this. It’s a software problem, right? And it sounds like you quickly discovered it wasn’t a software problem. So tell me about that pivot.

Melissa Hanna (06:21.759)

Yeah, I wish I could say that I quickly discovered that because it’s a little bit more painful than that. But I will say that this business being in the healthcare industry has had a different sort of profile and different time horizon than businesses and other verticals that are VC backed and sort of, you you come to an idea, you put it in the market, maybe the first version doesn’t work, you test it again, and then all of a sudden you’re like, this is actually taking off.

John Biggs (06:25.174)

Okay.

Melissa Hanna (06:51.553)

We actually, we did have that experience with our software solution. And I can talk about that in a second, but suffice to say that we saw growth within the software play that we originally developed. But what was happening behind the scenes is we started to understand that the market wasn’t actually mature enough. The market wasn’t established for scale. So even though we launched something and we did have that moment of like, this is going to be big. When we started to see the development of that business,

the signs were there and they were small and they were sort of early because the market wasn’t developed yet to say, this might not get as big as we want it to get. And that was the critical insight. So I said, I wish it would have happened sooner, but it took years really to understand first what the software problem was in the market. And I talk about the fragmentation and sort of like the payment challenge.

I’ve got emojis there, I don’t know. But I have to avoid talking with my hands too much. The software challenge was much more apparent because the United States has so many different kinds of healthcare institutions and so many different ways that healthcare is paid for.

John Biggs (07:54.126)

Yeah, that’s done. It’s a bad one. Yeah, okay, great.

Melissa Hanna (08:18.145)

That means there’s a lot of different kinds of providers that can provide that care, whether those are retail providers taking cash pay, whether those are integrated delivery networks in large systems like the Kizers and Geisingers of the world that have a much more integrated set of hospitals and doctors’ offices and urgent care facilities and all of that, and plans associated with their brands.

And then you have sort of your freestanding medical facilities of all different types and you take your commercial insurance or you take your Medicaid insurance to these organizations and you hope that insurance is going to pay for most of the care you receive. So there’s like so many different ways that people get health care in the United States that we first had to figure out, could you build software that could connect these systems together? So we did that actually for the first five years of this company’s life.

And what we realized was that in order to find the missing data that would tell a different story and provide an opportunity to actually improve clinical outcomes within this population, we had to distribute software to a number of independent providers that really didn’t have those tools yet. So we’re talking about those doulas, those lactation consultants, mental health providers, nutritionists, nurses that are working in the communities. Often they’re working in private practice or maybe even a

local community center, a nonprofit with some grant funding and providing those in between moments of support between going to your OBGYN and your pediatrician’s office for clinical care from your doctor, maybe your baby’s doctor. There’s all these other people you’re talking to along the way. And a lot of those people had really important insights, but that data wasn’t actually manifesting. wasn’t surfacing in the system. And so that was the key. That was the first insight was, okay, we to get them online. We have to actually

create tools for these kinds of providers. And we did. We created an electronic health record. We created a care management system, a communications tool set, a number of different features that allowed for these providers to provide care in the community. And as sort of part and parcel of that, we realized, OK, now I to figure out how to actually create more of that market, because a lot of the rich and valuable data was actually coming from these folks. You kind of tell your dual in your life story. You tell your Latish consultant,

Melissa Hanna (10:37.067)

you know, the aspects of, you know, your experience that you might not feel comfortable talking about with your OB-GYN. Even though we want you to feel comfortable talking with your OB-GYN, it might not be happening. And so someone else might be getting that story. What can we do to empower that person with that key information about your health and wellbeing to be able to participate in improving your care? And so we had to find a way to actually fund these providers getting into the healthcare stack is what I call it. Really getting them to be able to

John Biggs (11:05.88)

Mm-hmm.

Melissa Hanna (11:06.987)

participate fully as players on that patient’s team. So we had the tech for them. We had to figure out how to actually finance this. When we realized that the payments model for these types of providers was severely broken, that became a major blocker. said, wait a minute. OK, there’s all these people out here that can provide this care and have this really valuable insight and this really powerful way that they can have an impact in the industry. But they’re not participating in the health care stack. And we can’t seem to figure out how to get

payments flowing to them because insurance wasn’t covering a lot of these services. So the tough realization here was that being a pure software play was not going to maximize the impact, the ability to achieve the mission of the company, the valuation of the business, right? Because there was this blocker in terms of how these services are actually funded to allow for greater participation.

in healthcare. Otherwise, you’ve got, you know, all these doctors, hospitals, all these folks that care about you and are providing care to you, but they’re missing a piece of the pie over here. And these folks are just out of the system. We ultimately became a tech enabled healthcare services provider. We took the tech that we had built initially and we started to employ those providers and actually build the scalable healthcare organization that had all of those independent and slurry wraparound service providers in house. Because without that,

John Biggs (12:14.36)

Mm-hmm.

Melissa Hanna (12:34.123)

We just had a market that wasn’t scaling on its own. We had to become the scalable player. And now we have become that.

John Biggs (12:41.806)

Did it ever get so frustrating that you just didn’t want to just didn’t want to continue?

Melissa Hanna (12:48.363)

There certainly have been moments. Yes. The mission is, it’s sort of like a well to drink from, to restore yourself because as long as this continues to be an issue in the United States, for myself and for many others, certainly the folks in our company and I think a lot of our peers across the industry, this is just something that people can’t stand, they can’t live with.

And so yeah, it’s hard. It’s hard building a startup, right? It’s hard to build a startup in healthcare. It’s hard to build a startup for women’s healthcare. All of those things are true. But you look at the stats, you look at the economics of the industry, we’re talking about a trillion dollar market that is healthcare in the United States. Maternal and infant healthcare is approaching a $200 billion market. It’s tracking to be on par with the size of the global video games industry.

John Biggs (13:44.413)

Okay.

Melissa Hanna (13:45.57)

to an investor, it’s like, you could back video games or you could back maternal health care. And a lot of people are like, I hadn’t thought of it that way. That’s part of the problem. And I feel like as long as I’m sitting in the seat, I get to sit in and seeing the big opportunity from a clinical impact and also from a financial impact perspective, like, this is where I want to work, this is where I want to build. But yeah, definitely there are hard days where I think, gosh, when is this going to change and mask across?

across the country, especially because there are opportunities globally to take these insights elsewhere too. But there’s a lot of work to do here and as such there’s a lot of value built here.

John Biggs (14:25.196)

What about investment? mean, I’ve heard historically it’s been difficult as a female founder to get investment and then specifically talking about maternity, some dude in a vest on Sand Hill Road probably doesn’t know a lot about that. So what did you have to do?

Melissa Hanna (14:43.285)

Well, I think it’s a lot of reframing the opportunity so that people can find an access point into it. It seems big and far away. Someone else is having a not great healthcare experience in some other city, some other state, some other community that you’re not a part of, and that can make it difficult for the value proposition to resonate with investors. Ultimately, I both had to learn how to

reframe it for accessibility for those investors and also find the investors who it did immediately resonate with that knew someone who had gone through an experience that could have been better and wondered why it wasn’t and find investors who had had their own personal experience that was not what they expected it to be and started asking their own questions about like, why does it suck to have a baby in the United States right now? Like this should not be happening.

John Biggs (15:37.912)

Mm-hmm.

Melissa Hanna (15:39.682)

It shouldn’t cost this much. It shouldn’t feel this isolating and it shouldn’t be this medically difficult. You know, there’s so much risk associated with the care, lots of medical intervention that is not necessarily appropriate in every case. But in other cases, you you’re glad that there are people with, know, specialty, specialties that can save your life if that’s what it comes to, but not

every birth should be a life-saving instance of care. And so, you know, a lot of people that I met along the way were asking those questions because they had experienced it or they knew someone who had experienced it themselves. I’d say that’s a good portion of our cap table. Ultimately, though, we were able to bring in really strong investors from Sand Hill Road and from Wall Street and bring folks across the country to this work.

as the business was growing and demonstrating what it was capable of doing.

John Biggs (16:46.594)

When you were building this, did you expect to be able to ship some software and then just have the business? Did you expect this along a thing? mean, sounds like when you, it’s like trying to rebuild a, rehab a house or whatever. And then all of a sudden you find a bunch of like broken wood somewhere that you have to fix, right? So it sounds like you started digging and hit some rough spots.

Melissa Hanna (16:55.585)

Yeah.

Melissa Hanna (17:11.231)

Yeah, that’s fair. I don’t think that I ever imagined it to be an overnight success. I did feel very confident, and I still do, that technology is a very critical component in solving this problem. And that’s why we’re ultimately a heavily tech-enabled health care service provider. We develop software every day. There are things every day that we’re doing to...

refine the operation and ask questions about how we provide a better patient experience, how we provide a better provider experience through technology itself and through even connected devices that we use for real patient monitoring. So there’s a number of different components to this that just continue to persist because the core thesis was right, but the market wasn’t ready for it. Actually, you use the analogy of sort of a house you buy in.

Yeah, you find some things wrong with it. The analogy that resonates for me, the movie, The Founder, and sort of the Ray Kroc, McDonald’s story, like trying to sell milkshake machines and being like, this could be huge. This is a really great piece of tech and everyone should have it for their burger stand. And then, you know, going out to try and sell to burger stands and realizing that none of them had the scale to need this like.

John Biggs (18:09.742)

Mm-hmm.

Melissa Hanna (18:35.349)

you know, this great piece of equipment. It was just like not where their heads were at to buy that equipment. And then, you know, him coming across the McDonald’s, you know, stand and being like, wow, okay, they’ve got something here. Like this could actually scale. Realizing that, you know, you couldn’t sell the piece of technology until you could find the business that could scale and use it and really, you know, realize the value of it. That resonated when I watched that movie because...

John Biggs (18:57.357)

Mm-hmm.

Melissa Hanna (19:03.391)

That’s kind of how I felt going out there trying to convince your sort 1Z, 2Z, doula, lactation consultant outfits, like, you guys need to get online. You need to have a complete set of medical software tools to book and schedule and communicate. Have you guys heard of HIPAA compliance? And they’re like, what? And I’m like, you guys, you’re going to be subject to state and federal regulation soon enough. And I got laughed out of so many rooms because people were like, no, this is not.

John Biggs (19:26.926)

Mmm.

Melissa Hanna (19:30.057)

where we’re at, we’re not going to need this. We fly under the radar of the rest of the healthcare industry. And I was like, but do you want to? Like, is that where you want to be? Because the care that wraparound service providers offer is so essential to the broader experience that noon expecting parents are having as consumers. I was like, that’s going to be like really valuable. And a lot of people were just like, yeah, no, I don’t need your app. And

And what’s interesting is I did find a lot of people who did, and we ended up having thousands and thousands of providers sign up across the country. We were in 44 states with providers using our software to provide care in their communities. And from a footprint, we were like, okay, geographically, like this is great. But from an actual like scale capacity standpoint, like each provider was taking care of like dozens, maybe a hundred patients a year.

Right? So like each person kind of could only do so much on their own, even with a great piece of tech. And we were getting that feedback like, yeah, okay, I see what you’re doing here. Yeah, it is right. It is nice to have these kinds of tools and the ability to book and schedule and pay, you know, charge people and track my patients care longitudinally over the course of their maternity episode. Oh, this sounds nice. And I’m loving using it for my 50 clients. And I’m like 50 clients. There’s like

you know, almost 4 million babies born in the country every year. How are we going to actually get to scale? And we ultimately, this vertical integration, bringing people together and saying, well, maybe on an individual basis, y’all are doing the most. You’re doing what you can and it feels impactful. But what if we joined forces and created a team-based model of care? Then what happens? And the amplifier of that really is

John Biggs (20:59.63)

Mm-hmm.

Melissa Hanna (21:27.499)

people are doing 10x what they were doing before. Each provider is able to do so much more. And the data is living this out. We’re taking care of thousands and thousands of people a year because of this shift in operations. Ultimately, that’s what we did.

John Biggs (21:45.486)

Tell me a story about somebody whose life you changed because of this.

Melissa Hanna (21:49.062)

There’s we get letters every day. We get emails. We get cards in the mail with baby photos There’s so many There there’s there was a mom recently that it was this was a Unique one in that we get a lot of like first time, you know, I couldn’t have done this without you. This was amazing Thank you so much first time parents, but

It really strikes me and it strikes the team when we get a message from someone who is not a first time parent, who has been through this before and is already carrying the burden of their previous experiences. And this was a young woman, early 20s with a toddler who became pregnant in a

again in a very rural part of the state. There’s like one hospital there, one doctor’s office. And she found out about Mahmee being available through her insurance plan. And she didn’t know what it was, but she told us that based on what happened to her the first time around and how difficult of a medical experience it was for her.

The pregnancy was otherwise pretty smooth and she was very healthy and very excited to be pregnant. But once she started to get into care, she felt so judged many times over. This was a woman of color who had said, I just didn’t even know what to expect, but I had doctors asking, are you ready for this baby? You’re really young. She was still in school and she was just...

She said she had no agency in her initial pregnancy experience. And the labor and delivery was very difficult and she was in pain and everyone was like, well, this is what happens when you get pregnant. Like, what did you think? Labor and delivery is not easy. She wanted medication. There was just a lot of bias that was creeping into this experience in a story that was an otherwise medically well patient. And this is not to say that anyone around her wanted to make her feel bad, but

Melissa Hanna (24:13.587)

In these high stress moments and when patients are going through their own emotional and physiologic birth experience, it can be a lot. And then people start saying stuff and they don’t even realize sometimes what they’re saying to you. I’m not going to defend her medical care team from her first pregnancy, but hearing this woman’s story, it just sounded like people didn’t know how to control themselves as she’s screaming in pain there and being like, my God, the baby’s coming in. like.

Okay, yeah, well, we’ll go get the doctor for you. And just this attitude around it. The second time around, she wrote in was to tell us that she didn’t know how many places along the way between her pregnancy experience and her labor and delivery experience, and even in postpartum, she had agency. She didn’t know that there were moments where she could say, hey, this is how I want it to go. Like, can we try this? Can we slow down here? Can you give me a second to do some deep breathing?

what are my options for pain medication versus, you know, sort of haranguing her for asking for any at all. She didn’t even know necessarily what the different choices are. And it isn’t just epidural or bust, right? There’s a lot of different ways to manage pain. There’s a lot of different junctures where a medical decision needs to be made. And if the patient isn’t fully empowered and educated in what those decisions might be, the doctors and the nursing team will very quickly start to step in and sort of direct you toward those decisions. And so,

John Biggs (25:14.478)

Mm-hmm.

Melissa Hanna (25:39.296)

She wrote in and her message was, I didn’t know that there were moments where I could say no. I didn’t know there were moments where I could just take a beat and participate in it and direct others around me. And this one was very powerful because it speaks to how outcomes actually do change because there are people who have clinical risk. We take care of a very high risk population, patients that come in with a history of diabetes.

A history of hypertension, cardiac concerns, multiple high risk pregnancies, right? These are stories where there’s already going to be like a whole medical team around this patient. But we’re talking about a young woman who has no other history, no other concern, but said, I was so terrified to get pregnant the second time. I thought to myself, my gosh, like I want this baby, but I don’t want to have to go through what I did before. Ultimately, that narrative is one that we love hearing because it talks about sort of the silent majority.

of what women are going through in this country, which is to say that if you don’t have access to education, support, a provider or a team of providers like you get at Mahmee who can empower you to be able to say no, to be able to know what your choices are and how to direct and participate in your own pregnancy and labor experience, there’s a whole other storyline that may happen that may lead someone to say later, my gosh, that pregnancy was so difficult, or I really didn’t enjoy.

labor and delivery when it should be a wonderful and empowering and you know, Exciting experience to meet your baby So that’s that’s one where someone said you changed my life and what she meant when she said that was was very clear that it wasn’t just about that Eternity experience it was that someone for the first time in her life said, you know, you have the power you actually have the agency here and and you’re in control of you and

John Biggs (27:16.418)

Yeah.

Melissa Hanna (27:36.637)

you have a right to speak up for yourself. And it was, my gosh, we were all moved by that.

John Biggs (27:42.84)

Well, that’s beautiful. Yeah. thank you for this. has been a, like, it’s fascinating to see a move from like, I don’t know, pure software play. I’m going to solve this thing. And then all of a sudden you realize there’s so much to solve and comes down to just people, right?

Melissa Hanna (27:55.809)

Yeah, that’s it. It ultimately comes down to how we care for each other. There are many different ways that people are addressing health care issues across the United States. I’m really excited about all of the ways that people are now imagining AI as a component of these solutions. We’re doing that work as well. What we found is that it’s always been and it’s always needed to be the combination of people and tech.

And so whatever that combination looks like as we go forward, it’s that blend of the two because caring for each other really is where you have transformative experiences where someone says like, it only took one person. It only took one person being by my side to help transform the narrative for me. And everyone deserves that. And it shouldn’t be something that’s a luxury. It shouldn’t be something you have to pay through the nose to get. And that’s why I’m excited about what we’re doing because

it’s possible now to give this experience, to make this experience available to a lot more people.

John Biggs (29:01.326)

The service is called MAHMEE.com. Melissa, thank you for joining us. been great. All right. This has been Keep Going. I’m John Biggs. We’ll see you next week.

Melissa Hanna (29:09.409)

Thank you so much.

It’s a real estate debt platform, but not in the way people usually think about it. They’re not funding big speculative builds. They’re financing existing properties that already generate cash or can be fixed up quickly.

A lot of what they do is tied to a simple problem in Europe. It takes too long to build anything new. Permits drag on. Projects stall. Costs stack up. By the time something is finished, it’s more expensive than it should be.

So they skip that entire process. They focus on renovation. Old buildings. Misused space. Things that can be turned around in under a year and put back into circulation.

Read more

An agent is just a chatbot with access. It can reach into your files, your email, your servers, and your tools.

In this video I show a live setup. We ran OpenClaw on a Raspberry Pi, connected it to Telegram, and used it to make real changes. It edited a website header, sent emails, created a simple site, and monitored inputs, all from short prompts.

Gradient Ascendant

How to OpenClaw your Raspberry Pi

The tech world has gone gaga for OpenClaw, a project that lets you run an always-on AI agent; give it “skills” such as deploying code, searching the web, or summarizing your emails; and communicate with it via Slack or Telegram. Is this fun and interesting? I think yes! Are people doing fun and interesting things…

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2 months ago · 9 likes · Jon Evans

I also spent time on the risks. Giving a system this level of access is not trivial. It can write code, trigger actions, and touch production systems. It is useful, but it demands caution.

The goal was simple: I wanted to strip away the hype and show what this looks like up close and how it works. As a fan of exploring new tech, I hope you enjoy this quick video and I’ll probably do another one in a few weeks.

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I spoke with psychologist and author Guy Winch about his new book Mind Over Grind, which looks at a familiar but poorly understood problem: the slow psychological takeover that happens when work becomes the dominant force in a person’s life. Many of us think we are simply tired or busy. Winch argues that something more corrosive is happening, a kind of sustained dread that alters how we think, how we behave at home, and how we relate to the people around us.

The timing is not accidental. The workplace is changing in ways that make people uneasy. The pandemic briefly pushed companies to talk about emotional health and work life balance, but the underlying pressure never really went away. Burnout continued to rise. Now a new layer of uncertainty has appeared in the form of AI, automation, and the constant sense that entire professions may shift under our feet.

That uncertainty produces a specific emotional state. Winch calls it dread. It is not simple stress or boredom. It is the heavy anticipation of something bad that may happen but cannot be clearly defined.

Psychologists have studied this kind of anticipation in laboratory settings. In one set of experiments people were given a choice between receiving a mild electrical shock later or a stronger one immediately. Many participants chose the stronger shock simply to avoid waiting for the mild one. The anticipation itself was so unpleasant that people preferred to get the pain over with.

Work can produce the same effect. When people wake up already dreading the day ahead, the stress does not remain confined to office hours. It bleeds into everything else.

A common pattern looks like this. Someone finishes work but cannot mentally leave it behind. They replay conversations with colleagues, worry about tomorrow’s meetings, and anticipate problems that have not yet happened. These thoughts arrive uninvited. They intrude during dinner, while watching television, while trying to fall asleep. The result is hours of unpaid emotional overtime.

The damage compounds quickly. Poor sleep makes people more reactive the next day. Emotional withdrawal leads to tension with partners and family members. Hobbies, friendships, and personal interests slowly fall away because the person feels too drained to engage with them. Over time the individual begins to lose parts of themselves that once had nothing to do with work.

Winch has seen this pattern repeatedly. He also admits that he has experienced it himself. That admission is important, because the problem is not limited to employees trapped inside rigid corporate structures. It often appears even more strongly among founders, freelancers, and people who run their own businesses.

Self employed workers do not have a boss setting limits on how much they can push themselves. If you are ambitious and motivated, there is always more to do. A new client to chase. Another product to ship. Another email to send. The boundary between effort and obsession can disappear without anyone noticing.

Technology complicates the picture further. AI systems can now perform many of the small tasks that once filled the workday. Drafting emails, organizing schedules, producing summaries, even generating reports can be handled automatically.

In theory this should reduce pressure. In practice it often does the opposite.

People rarely use saved time to step away from work. Instead they fill the space with more tasks. At the same time the presence of automation introduces a deeper anxiety. If a machine can handle part of your job today, it may handle the rest tomorrow. Entire professions now operate under that shadow.

Even psychologists are not immune. Winch mentioned that some of his clients already consult large language models when he is unavailable. Others bring AI generated advice into therapy sessions and ask whether it matches his recommendations. The implication is obvious. If a machine can simulate the voice of expertise, what happens to the human expert?

These questions are still unfolding. Researchers have only begun to examine the psychological consequences of widespread AI interaction. One emerging concern involves emotional attachment to digital agents. Some people now describe their AI assistants as companions or collaborators.

Winch views that development cautiously. Emotional attachment to software may signal that other relationships have weakened. When work dominates a person’s attention and energy, connections with family, friends, and communities can erode. In that context it is not surprising that people begin forming attachments in strange places.

None of this means that work itself is the enemy. Winch argues that work occupies a central place in human life for understandable reasons.

Most people spend more waking hours working than doing anything else. Work provides income, which satisfies basic needs like shelter and food. It also offers social structure, status, identity, and a sense of accomplishment. Much of Maslow’s hierarchy of needs, from security to self esteem, flows through employment.

Because of that, threats to work feel existential. Losing a job does not only mean losing income. It can mean losing status, routine, social networks, and a sense of purpose. The unconscious mind interprets those risks as serious dangers, which helps explain why dread becomes such a powerful emotion.

The real question is how to prevent work from overwhelming everything else.

Winch’s approach is pragmatic rather than philosophical. He focuses on specific behaviors that interrupt the cycle of rumination and anxiety.

One of the most common traps involves replaying workplace conflicts or uncertainties long after the workday ends. The brain returns to the same problem repeatedly because it has not identified a resolution. The solution is to convert the worry into a concrete plan.

If you are stewing about an argument with a colleague, the task becomes identifying what outcome you want and how you might achieve it. Do you need a conversation to clear the air. Do you need to set boundaries. Do you need to escalate the issue or simply move on. Spending fifteen minutes outlining a response can quiet the brain because the uncertainty has been reduced.

In cases where the problem cannot be solved immediately, scheduling time to address it later can have a similar effect. Writing “handle client issue tomorrow at 8:45 a.m.” into a calendar signals to the mind that the concern has not been ignored. The worry is parked for later rather than allowed to circulate endlessly.

Another element involves the structure of the workday itself. Many people respond to overwhelming workloads by pushing forward without pause. They move from meeting to meeting, task to task, trying to survive the day.

Ironically this behavior reduces productivity. Cognitive performance declines as fatigue accumulates. Creativity, judgment, and executive functioning all deteriorate when the brain remains under continuous strain.

Short restorative breaks can interrupt that decline. A few minutes of physical movement, a brief walk outside, or a supportive conversation with a colleague can reset mental resources. What matters is that the break genuinely restores energy rather than adding more stimulation. Doomscrolling through social media or reading the news rarely qualifies.

These techniques are modest but practical. They require attention rather than radical lifestyle changes. Most people already spend hours each evening mentally revisiting work problems. Redirecting a fraction of that time toward structured reflection can produce a noticeable difference.

The deeper question that emerged during our conversation concerns the future of work itself. If automation eventually provides widespread basic income and eliminates many traditional jobs, what replaces the psychological role of employment?

Winch does not pretend to know the answer. Work provides purpose, competition, creativity, and social structure. If those elements disappear, people will almost certainly invent new forms of aspiration to fill the gap. Humans rarely remain idle for long.

The shape of those aspirations remains unclear. They might emerge in artistic communities, local organizations, scientific exploration, or forms of competition that do not yet exist. What matters is that the underlying psychological drive toward goals and progress will remain.

For now the immediate challenge is simpler. Work has always demanded effort and attention. What has changed is the degree to which it invades the rest of life. Phones keep us connected to the office at all hours. Global competition raises expectations. AI adds uncertainty about what the future holds.

The result is a quiet epidemic of dread that many people treat as normal.

It is not normal. It is a signal that the balance between effort and recovery has collapsed.

Rebuilding that balance does not require abandoning ambition or disengaging from work. It requires noticing how the mind responds to pressure and intervening before the grind becomes the only thing left.

Ahoy!

I’m hosting a short Zoom session for the Keep Going community on March 16, 2026 at 1:00 PM EST where we’ll walk through installing and trying out OpenClaw.

RSVP

OpenClaw is an open source tool that lets you run and manage AI agents locally. A lot of readers have asked how it works and whether it’s difficult to set up. The answer is that it’s not impossib…

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Hi,

A quick reminder to the Keep Going community.

I’m trying to return to journalism full time, both here and at Resilience. That means I need paying readers. I have a family to support and a small dog named Nina who eats more than you’d think.

Here is the reality.

Startup journalism is collapsing. Reporters are leaving the field. Most coverage has turned into lightly edited press releases written to please investors and founders. The hard questions rarely get asked.

I’m trying to do the opposite.

At Keep Going I want to publish original reporting, real founder interviews, sober analysis, and clear takeaways you can actually use. No pay-to-play. No sponsored nonsense. Just reporting.

But that only works if readers pay for it.

So here is the ask.

Subscribe now and I’ll give you 20% off for life. That’s $40 a year to help support real entrepreneurial conversations with real CEOs and researchers.

Get 20% RIGHT NOW

If you read Keep Going and it helps you think about startups, technology, or the future of this industry, please support the work. Paid subscriptions let me stay independent, cover difficult stories, and keep writing without answering to advertisers or investors.

This is a one-man newsroom. I’m doing everything I can to make it worth your time. I’m interviewing fascinating people like Patricia Martin (whose insights made me cry), Kevin Gaskell who turned around Porsche, and thinkers like Dr. Rod Berger.

But independent journalism only survives if readers decide it should.

I love startups and I love honest conversations. I think you do, too. I will share this reminder about once a month. If Keep Going has helped you think, build, or avoid a mistake, please help me keep it going. Thank you.

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On this week’s episode of Keep Going, I spoke with Patricia Martin, writer, researcher, and author of Will the Future Like You? She has spent a decade studying what happens when failure is not just professional but personal. The kind that makes you wake up and ask, who am I now?

Patricia calls it identity-threatening failure. Not every setback qualifies. Missing a target or losing a client stings. But when your business is your baby, when your persona is fused to your public presence, when your work becomes your self, a collapse can feel like rejection at the level of love. The brain codes it that way. Cortisol rises. Adrenaline spikes. Dopamine drops. Executive function weakens. You feel empty, hypervigilant, unmoored.

Entrepreneurs are especially vulnerable. We are taught to invest identity in what we build. In the attention economy, we perform ourselves across platforms, post after post, video after video. The persona gets muscular. The inner self gets quiet. Patricia calls the result “persona fog.” We externalize the self so thoroughly that when something breaks, we do not know what remains.

What struck me was how physical this all is. This is not motivational poster talk. There is a somatic reaction to identity collapse. A rewiring. Some people pivot sharply. A tech founder goes back to the family farm. A software executive returns to the factory floor. Not because they failed, but because they need ground again.

So what do you do if you cannot escape to a dairy farm?

Patricia argues there is no hack. There is practice.

First, discernment. Identity failure scrambles executive function. You lose clarity. You must relearn how to hear yourself.

Second, reflection. We have lost the muscle of self-reflection. There is no app for the inner world. You have to sit with the question: what is this doing to me?

Third, confirmation and witness. Own what is happening. Say it out loud. Find someone who can remind you who you were before the fog rolled in.

As we talked, the conversation turned to AI, to coders who fear obsolescence, to journalists wondering what work remains. Patricia’s answer was not comfort. It was responsibility. You must know who you are. You must identify what you bring that cannot be replicated. Creativity. Imagination. Sentience. The ability to feel and transmit meaning.

Machines can perform. They can flatter. They can automate. They cannot enact being.

We are entering what she calls an age of hyper reinvention. Pivots will not be rare events. They will be routine. That means resilience can no longer be grit alone. It has to include an active relationship with the unconscious, with creativity, with reflection.

There is a line Patricia shared that I keep returning to. Every defeat of the ego is a victory for the unconscious.

In a culture built on dominance and performance, that feels radical.

The question is not whether the future will like you. The question is whether you can hear yourself clearly enough to survive it.

Transcript

Welcome back to Keep Going, a podcast about success and failure. I’m John Biggs. Today we have Patricia Martin. She’s a writer, she’s a podcaster, she’s a researcher, and she’s recently wrote a book. It’s coming out soon, Will the Future Like You? Which I’m afraid to hear the answer for, so welcome, Patricia.

Patricia (01:26.852)

It’s a pleasure to be here, John.

John Biggs (01:28.942)

So you’re an old hat at podcasting. You’ve been doing this for quite a while. A million views on your stuff. I want you to welcome to mine. And I’m actually really happy you’re here because this book sounds fascinating. Why don’t you just give us a quick recap about what you wrote.

Patricia (01:45.167)

So I researched this material in the book for 10 years. And I entered into the research originally to understand the impact of the digital age on the human psyche. And I encountered not only a variety of people and their stories, and then also, you know, as an entrepreneur myself.

I underwent a massive change in my life and in my business. And I woke up one morning asking the age old question, who am I? And that is when my research took a fresh direction. And I began focusing on what it means to lose and rebuild identity in the digital age.

John Biggs (02:34.144)

Mm-hmm. So you were talking earlier about the identity destroying failure. I guess reducing failure, right? A failure so poignant that it changes essentially your entire life. So tell me about that.

Patricia (02:49.378)

So not every failure that we have affects us at an identity level. What tends to happen though with entrepreneurs, and I would say this is generally a cultural issue for Americans, is that we invest a lot of identity in what we do. Entrepreneurs more so because it’s your baby, it’s your creation. You’re doing something, usually it can be out of a passion or you’re addressing a need in the marketplace.

But it is something that you have spotted and you internalize as part of yourself. So what happens when we fail at an identity level, especially in the attention economy, is that we begin to recruit differently from the interior world of ourselves. So let’s say, for instance, you have somebody who has built an online business and they’re an influencer.

That is persona heavy identity. And the persona is the weakest part of the psyche. It has never been, it was never designed to undergo the garrulous rigors of online life, right? And yet we’re pounding it day after day, post after post, video after video. And so when something goes awry there, there are some specific things that start to happen.

when we tip that into an identity problem. So first of all, it’s a social neural pain. We treat that failure as a rejection, just like we would treat it as a love rejection. And that’s how the brain codes it and the body feels it. The other thing that happens is it’s probably not a surprise that we get a cortisol rush from that kind of failure, but it has a lingering effect.

Probably I think the most intriguing thing that came out of the neuroscience is the amount of adrenaline that courses through the body during a failure that is specific to the loss of identity. So it’s as if we are now hyper vigilant to find our sense of self again and we begin the search to recruit back the sense of who we are.

Patricia (05:10.536)

And so that has an effect that is, you know, and your dopamine goes low. So now you’re operating on cortisol, adrenaline, and low dopamine. So it’s kind of a perfect storm for feeling really empty, lost, stuck, disconnected. So, you know, you’ll talk to people who have had a failure like that. And it requires in the attention economy more than just grit.

Because it’s moving so fast, you’re not just, you know, pulling yourself back up by your bootstraps and standing back on your feet. Back on what? What ground? The territory is moving so fast. So this is where you find people tend to tumble out. You’ll also find people at this point sometimes will take a sharp pivot. I talked to people who went from

running software companies to working in their father’s box factory. One woman was in a tech startup that got really big. She sold it, and she went back to running the family dairy farm. So it was kind of like they needed an antidote to kind of clear themselves. some of these were success stories. But what was interesting is that some of them didn’t go back to the hurly burly and the grind of something that was as intense.

as an online business.

John Biggs (06:38.67)

So I love that you’re able to codify this and describe it in a very clear way. think a lot of people have that. I mean, first off, a lot of people have that fantasy, right? I think that every single Hallmark movie is about that, where you go back to the small town and you become a dairy farmer after having a hard business, like a hard charging business life. So I think the primary question is, you’re in that mode, once you end up failing out of it,

out of an entrepreneurial situation, you described the persona being destroyed to a degree. from a layperson’s point of view, the persona would be just, I don’t know, just my day to day happy-go-lucky whatever. But it sounds like you’re talking about something a lot deeper here. what happens when that identity is destroyed? And how do we get it back, aside from working at a dairy farm?

Patricia (07:30.989)

Well, here’s the thing. Yeah, because we can’t all do that, right? And some people genuinely like to learn and ladder up. Failure, success, failure, success. I think, though, what’s important to understand about the difference between a more linear type of set of milestones in one’s career and the matrix of what we’re experiencing now.

So pivots and turning points happen more frequently. I think we’re going to see with the rise of AI, that is going to become an annual event for people. I’m just putting a pin in that. We’re going to be pivoting more and more and more. And so I think the problem with the internet age is it has made us externalize the self.

So, you know, there’s no app for the inner world. We are always out there. We’re always on. We’re always pushing content. And we’re dividing our sense of self across multiple platforms and multiple personas. So when we’re externalized like this, we’re vulnerable. We’re vulnerable to the kind of change.

the kind of failure that we’re talking about that have real bodily consequences and psychological consequences. So I would say the plague of our time is something I identify in the book as persona fog. And what happens is that when this gap opens between the true self and the externalized self, we’re no longer in search for the self.

We’re performing a self. That’s a very different proposition. The self is at arm’s length to begin with, also making us vulnerable. And so when we take a loss and we’re in this fogged state already, first of all, it’s very hard to hear the signals from the self. I’m a Jungian, right? People fall into, are you?

John Biggs (09:53.484)

You don’t look it.

Patricia (09:54.222)

Are you a Freudian or a Jungian? And I’m a Jungian. And Carl Jung’s definition of the self is that it is actually an ever active resource in our lives and it will give us symptoms that are signals. And these signals will continue, they will persist.

plasticity in the self. And the trouble with persona fog is that when we identify so much with our external self, you know, we’re, there’s a noise floor we’re hitting so that we can’t hear the signals. So we prolong our pain and suffering. so, you know, part of what the mission of the book was is to help people understand how to hear those signals first and then what to do about them. So I think the

Antidote is like a three-part process and the first requires discernment and that is tough because another thing that goes offline when we have an identity failure, you know, when our failure is an identity failure is we lose, this has been proven, we lose loss of executive function. So some of what makes us feel competent and like you have a handle on this, this is lost to you and that

John Biggs (11:16.11)

Mm-hmm.

Patricia (11:23.507)

also means a loss of discernment. having to tune into yourself becomes a practice. It’s not a hack, it’s a practice. You have to get good at listening to the signals of the self so that you pull yourself up off the noise floor. The second thing you can do is, this is so simple and this sounds a little self-helpy, John, but we’re losing this ability to reflect. I mean, you could talk to anybody in psychotherapy.

And they will tell you what the one primary skill is, self-reflection. We’re so out there, we found it hard to get back in here. And the myth of the digital age is that what we put out there has no effect, right? About what’s going on inside. Like that is the biggest myth we need to shatter. So, know, reflection is like, okay, I failed.

How is this making me feel? What’s going on inside there right now? Just asking ourself a simple inventory of questions. And then I think the third thing is to confirm. Confirm with yourself. Own it. This is what’s happening to me. This is how I’m reacting to this psychologically and physically. And then to seek a witness. To seek.

someone to talk to, someone who can reflect with you and remind you, well, this is how I see you. This is how I’ve always seen you. You can’t, I can’t state this enough. And it’s part of what made me seek out psychology because as I was interviewing some of these entrepreneurs, they were kind of turning me into their therapist. And I thought it was in over my head, you know, like I’m a researcher and I’m a writer. I am, I’m really not qualified.

John Biggs (13:14.656)

Mm-hmm.

Patricia (13:20.436)

So that’s what kind of turned me into a Jungian.

John Biggs (13:24.898)

mean, that’s literally why I did this podcast, right? So I was a hard charging journalist weirdo for TechCrunch. I would get pitched at urinals. I had a million friends around the world, a million friends around the world, but if I was in a pinch, not a single one of them pick up the phone, right? So that was the depression aspect. And I also met so many entrepreneurs that were clinically depressed and some of them who died. I knew...

Patricia (13:34.225)

my God.

John Biggs (13:50.382)

quite a few folks who just couldn’t handle it. And I think this is so vital. mean, those three things that you just described are just the self-reflection, I think, is the other thing. I would also argue that in this day and age, those entrepreneurs are going to like mushroom retreats or whatever to get their self-reflection. Is that an alternative? Is that a way to go? Or should it just be sober reflection in a dark room?

Patricia (14:14.592)

Well, I think it’s interesting that people are trying to ingest consciousness.

John Biggs (14:20.736)

Mm Exactly. That’s I mean, that’s the answer, right? It’s like you said you said there’s no app for for self for the self. But to a degree, a couple of mushrooms are kind of like that. It’s like it’s like it’s like Matrix Neo in the Matrix.

Patricia (14:22.785)

Yep.

Patricia (14:34.6)

Right. And so, I mean, this is the danger of my work all the time. You’ve been asking me good, deep questions, but, you know, often people just want the set of 10 hacks, you know, the listicle. And that’s not what this is. I mean, I’m really asking people to take a hard look at what’s happening to them and how they’re losing their sense of self and what the costs are. And you’re right about the cost because, you know,

John Biggs (14:46.039)

Mm-hmm.

Patricia (15:01.458)

One of the people that I had in the research study attempted suicide. mean, the costs are very real. so what you’re really talking about though is rich because, you know, Carl Jung was a big believer that much of what makes us who we are lives in the unconscious. It’s not a fish, it’s a whale we’re riding on. And so to access that.

is vital in restoring your sense of self. And so it doesn’t surprise me that people are taking hallucinogenics and people are ketamine and people are trying to get there however they can. I have never done it myself. So I’ve looked at some of the science on it. I can’t poo poo it, but I certainly can’t proclaim it either. I think the more opportunities you have to

raise the unconscious and make it conscious, the better you’re going to be. So keep in mind the persona is attached to the ego. And Carl Jung said, every defeat of the ego is a victory for the unconscious. And so the more you confuse the two, the more you fuse the two, the more resilient you’re going to be. So this is like keeping just a simple dream notebook.

John Biggs (16:15.822)

Mm-hmm.

Yeah.

Patricia (16:28.574)

Next to your dream. mean, one of the things that I found is that some of the entrepreneurs I interviewed were so strung out, they weren’t dreaming anymore. And this is a, this is a signal. This is a signal from the self that you’re starting to lose your attachment to the unconscious. So anything you can do to tap into the unconscious meditation, walking, re embodying yourself.

I mean, we live such disembodied lives in the digital culture that even reconnecting to your senses by walking outdoors has a huge impact on your inner world.

John Biggs (17:14.958)

I like from a Jungian standpoint, we could argue that some of the self-medication and some of like raves and all that other good stuff, the group activities, et cetera, that these folks are Burning Man or whatever, they’re trying their damnedest to hit those notes and try to bring that unconscious up. What does it mean in a normal sense? Explain to me the idea of...

dissolving ego and connecting to the unconscious.

Patricia (17:48.748)

So the ego serves a function. That’s where your executive function emanates from. The ego plays a role. The ego is there for a reason. The ego will keep you safe. The problem is that the ego is hungry. And it will turn everything you do in your life into a project of the ego if you’re not attuned to that. And so this is where

You know, sometimes for an entrepreneur, the ego will be, will get, you know, you hear phrases like, you’re getting in your own way. That is typically the ego wanting to try to protect you from taking risks. So being able to monitor the ego is, valuable. especially for people who are reaching high strivers, entrepreneurs, but, but I would also say that we’re not trying to dissolve the ego.

John Biggs (18:31.47)

Mm-hmm.

Patricia (18:47.295)

What we’re trying to do is raise what is in the unconscious to bolster the other parts of the self, right? The ego is only one part of the self. And so it gets very muscular, especially in American culture. And you’re seeing this play out in politics and business, right? And everything else gets atrophied. So you’re trying to bring things into balance.

John Biggs (19:09.688)

Sure, sure, sure.

John Biggs (19:16.846)

So the suggestion is that the ego doesn’t allow for, I don’t know, obviously reflection and obviously maybe kindness to a degree. mean, if we look at the current political state, it’s all ego, right? It’s all bluster. And it’s all just the assumption you being right constantly is what’s polarizing us. So the question I have, especially related to the book, is how do we survive these next?

this next decade, right? So I was speaking to a guy just now who is, literally he’s been a coder all his life. He’s probably one of the best coders I know. And he says he’s going to be obsolete in half a year, basically because of AI. he can, the bosses who are full of ego say to themselves, we can replace this guy with a couple Claude instances and we’ve saved $200,000 or whatever this guy wants for his contract.

How are we even not the hard chargers? How does mental management survive this? How do the folks who are eking out a living being journalists and media creators?

Patricia (20:25.429)

of what you have to answer is number one, who are you? And really understand that and know that. number two, what you bring to this that makes you unique that Claude or Chachi B.T. cannot replicate. So I think where...

John Biggs (20:44.482)

Mm-hmm.

Patricia (20:50.097)

human contribution is going to be most valuable is in some of the ways that we as humans connect to each other and in some of the ways that we are sentient beings so that we receive messages and send them out to other human beings. So one of the things that fascinates me, John, is just how much the new platforms for AI have learned from

you know, years and years and years of internet success. And one of the things I’m really tuned into is how my robot wants to love Bummy. Right? I’m a genius.

John Biggs (21:30.318)

Mm-hmm.

Patricia (21:32.971)

And I have to tell you, if you talk to my robot, you know, he would tell you all kinds of things about just how special I am. What is at the root of that? They are coded in these early phases of public engagement to build trust that then can be leveraged and...

John Biggs (21:33.432)

Yeah.

Patricia (21:56.554)

you know, the en-shitification is coming, but it will learn as much as it can about us by love bombing us. And so...

awareness that we’re in this moment. I mean, we’ve been here before, right? Especially people like you and you and me, we were there in the early days. If you were writing for TechCrunch, you’ve been around. So we’ve been here before and understanding that this is the moment we’re at and really digging in and doing some work to understand who we are.

John Biggs (22:17.582)

Mm-hmm.

Patricia (22:32.651)

There was a case study that I wrote about in the book, Janet. She was a coder at a very young age. She went to a STEM school. And she was great at online gaming, massive multiplayer games. She was great at blogging. She was on every single platform at the time that was available to her. And she was 17. And around.

18, she was getting ready to apply for colleges and she was like, said, this was her phrase to me, I felt empty. She didn’t know who she was. So she actually disciplined herself to write a paragraph in her notebook describing herself to herself.

John Biggs (23:10.382)

Mm-hmm.

Patricia (23:21.771)

And then she went out to every single one of those platforms where she had a persona that was active and she ignored how many clicks. She ignored how popular it was. She ignored the places where she was trolled. And she said, is that me? Does that align with this paragraph? And if it did, she kept that voice. And if it didn’t, she, she self-regulated. And it was 18 years old. And I thought, what a lesson.

John Biggs (23:35.278)

Mm-hmm.

John Biggs (23:40.28)

Wow.

John Biggs (23:47.694)

at 18 too, which is wild.

John Biggs (23:56.312)

So this is heartening, Usually these things end up as not being so chipper. But I’m trying to find a historical corollary for where we are right now. we’re talking about, I always think about this scene in American Splendor where Paul Giamatti is working in a hospital. And this is the 70s. He’s working in hospital where there’s paper files everywhere, all over the place.

like in a few years, those paper files would have been gone. But at that point, he was as Harvey Picar was like in a in a room full of paper. And he was perfectly fine. He was perfectly happy. He was he was the kind of guy who would who wanted to be alone in this room. But when all that went over to computer, when all that went automated, what changed, he no longer had a place. So who gets who loses that who loses that that that position who loses that their persona when we go from

essentially dumb machines to machines that are either constantly like complimenting us or are doing most of our work for us and we no longer have that thing. How do we rebuild that persona in this case?

Patricia (25:07.848)

Well, that’s a huge question, OK? And listen, I’m still figuring some of this out myself. I realize that I have stumbled on territory that a lot of neuroscientists are also still trying to figure out, and psychologists. And the other thing about this, this is interdisciplinary work. And science has gotten so specified.

John Biggs (25:12.056)

Mm-hmm.

John Biggs (25:17.239)

Mm-hmm.

Patricia (25:35.752)

that we’re starting to behave now more like humanities departments, where there’s a guy in history and a woman in sociology and somebody else in art and culture. And we’re now starting to have conversations about how do we get back to a humanity that is resilient, has something to offer, and what is core to the human identity that

cannot be replicated. And some of that is actually has to do with getting back to what is creative about us. Creativity, imagination, that cannot be replicated by a machine. What the machine can do, just like love bombing, is it can give the performance of that, but it can’t enact it. And so I wrote a book in 2008,

which was called the Ren Gen, the rise of the Renaissance generation. And it talked about that in every, what are the conditions that precede a Renaissance? And it is always the same through history. Death comes first. The civilization is wiped out. A seed bed is created and something new emerges and it emerges from human contribution of creativity. So I think what we’re seeing now,

John Biggs (26:40.611)

Mm-hmm.

Patricia (27:04.828)

is we’re seeing how bankrupt this dominance and aggression script is. And what it’s doing, it’s very good at destroying, but it’s not creating anything. And so there is going to be an equal and opposite drive that will be toward creativity. And I can see the wheels of this starting to crank up. And so...

John Biggs (27:12.238)

Mm-hmm.

Patricia (27:33.876)

The future is yet to be seen, but the people who can tie into that part of themselves have a future.

John Biggs (27:43.854)

That’s amazing. I’m glad you said that. I think that’s vital to hear. think there’s plenty of people who just aren’t hearing that, right?

Patricia (27:50.792)

Well, that’s the noise floor. They can’t hear it. It doesn’t resonate with them. And dominance, when you look at the dark emotions that rule dominance, they’re constrictive for a reason, because that’s how dominance stays dominant. So people who wriggle out from underneath that, like if you saw the halftime show.

John Biggs (27:53.39)

Mm-hmm.

Patricia (28:19.642)

at the Super Bowl. You know, you see how people wriggle out from underneath that. And it resonates with a massive amount of other people. This is what I mean by humans being sentient. We pick up the signals across the culture from each other. And this is what will save us.

John Biggs (28:19.758)

Mm-hmm.

John Biggs (28:44.834)

Patricia, thank you for this. This has been amazing. When is your book coming out?

Patricia (28:49.726)

March 5th, launches, it’s in pre-order now. It’s called, again, Will the Future Like You? And it’s about this age of hyper reinvention when we’re having to pivot and pivot and pivot and reinvent ourselves, what it’s doing to us and what we can do about it.

John Biggs (29:05.998)

We’ve made a lot of people like me happy because I have like, on my LinkedIn, I think it’s like two or three pages of just like doing different things almost every year, which I think is, that makes me an early adopter of this future, right? It’s scary, but it’s fun.

Patricia (29:17.704)

Yes. It’s scary, but it’s fun. And you’re going to figure out like what keeps you resilient. The recipe is a little different for everybody. But the fact that you’re asking questions and you’re curious, the self always knows what it’s doing.

John Biggs (29:39.316)

Wonderful. Well, thank you for this. It’s been amazing.

Patricia (29:41.546)

Thank you. Pleasure.

John Biggs (29:43.79)

This has been Keep Going. I’m John Biggs. We’ll see you next week.

Kevin Gaskell walked into a room expecting to be fired.

Instead, he was handed the keys to Porsche UK.

That moment says a lot about his career. He is an engineer by training. Then he added an MBA. Then accountancy. Blueprint and balance sheet. He joined Porsche in his twenties, rose through operations, and found himself in a company that was sliding. Three years of unsold inventory. Brutal headlines. Public jokes about pigeons and deposits.

He thought he was getting a ten minute exit interview.

He stayed for four hours. He told the owners exactly what he thought. What to cut. What to fix. Where to aim. He expected consequences. He got promoted.

Five years later, Porsche UK went from last to first.

That sounds like a clean arc. It was not. They cut costs by 50 percent. They simplified. They endured press attacks. They carried the weight of three years of unsold cars. That is not glamour. That is grit.

Then he did it again at BMW. Then he quit.

This is where the story turns.

He left one of the best jobs in European automotive to build Cars Direct Europe. Rented office. Desk. Phone. Two young kids at home. American backers. Big plan. Six months in, the investors pulled out.

Gone.

Now what?

No salary. No bank support. No track record as a founder. Just a business plan and three colleagues.

This is the part people skip. The terror. The mortgage. The silent nights staring at the ceiling.

They negotiated a sliver of funding. Raised money from friends and family. No safety net. Then they pivoted. Consumers were not ready to buy cars online. So they went after fleet operators. Boring. Back office. Massive inefficiency. Two hundred people on phones sourcing cars.

They built a platform. They became the backbone. They prepaid dealers with token systems, which quietly funded their growth. Five years later they sold for nine figures.

That does not happen because someone is lucky.

It happens because when the bottom falls out, you do not flinch.

Kevin talks about luck. He was in the right room at Porsche. That is true. But courage matters. When you think you are about to be fired, you can shrink. Or you can speak clearly.

He chose clarity.

There is another thread running through his story. He does not build fragile companies. He stays five to eight years. He builds teams that can run without him. He does not asset strip. He builds foundations.

Today he runs multiple companies in parallel. Fiber networks. Data platforms. Investments. He has rowed oceans. Walked to the poles. Climbed mountains.

That part is dramatic, but it is not the point.

The point is this: failure comes first. Success is the fight that follows.

When the press mocks you. When investors leave. When no bank will return your call. That is the test.

Do you believe in the thing?

If the answer is yes, you keep going.

That is the through line.

Not hype. Not trends. Not whatever the market is excited about this week. He is openly skeptical of herd behavior in investing. Dot com. AI. Railways. The pattern repeats. Tools matter. Products matter more. Service matters most.

Build something real. Tell the truth about where you stand. Simplify. Cut what does not work. Double down on what does.

And when you think you are about to be shown the door, speak up anyway.

You might walk out unemployed.

Or you might walk out in charge.