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.

That’s the challenge Will Rubin is trying to solve with WorkClaw, a new product from Workmate Labs that turns AI agents into something closer to digital employees.

Rubin describ…

Read more

Reid is the CEO of Claer AI. The product is an AI-driven supplement regimen builder that asks for your health profile, matches it against a large library of peer-reviewed studies, then turns the recommendations into a practical plan, starting with sachets you can mix, and aiming later at a single personalised powder. He describes it as using AI like a nutritionist, then following that logic through a supply chain he already knows well.

His origin story is straightforward. Reid says he built and sold a social media analytics company to Comscore, then later ended up running one of the world’s largest supplement companies as part of a small executive team. That role changed his view of supplements, not as gym culture products, but as widely applicable compounds with strong safety profiles and real evidence behind them. He uses his own experience as the hook, after adding basic products like protein and creatine, he says he saw a clear change in strength and mobility as he aged.

The gap he wants to fix is trust and confusion. Reid calls the industry large but fragmented, and he points to consumer confusion as a driver. His claim is that people do not stick with one brand because the space feels like a Wild West, and they worry about doing something wrong or wasting money. Claer’s AI is meant to create a long-term relationship that adapts over time, including using biometrics from wearables and adjusting the regimen so users do not have to think about it constantly.

The most concrete feature he described is interaction checking. A common fear is that a supplement will clash with a medication or another intervention. Reid says Claer uses a “currently updated” evidence base to flag these issues, and he thinks that capability has applications beyond supplements, especially anywhere medication regimens shift often.

On funding, Reid says the company started self-funded, went through the ERA accelerator in New York, and that the health tech environment is active enough that fundraising is not the core problem. He frames the business model as bundles with solid margins and higher cart values, plus better retention because of the personalised front end. He also splits the company into two stages, first prove the commerce and retention dynamics, then raise larger funding later to personalise the manufacturing itself and deliver the single powder vision.

Reid also made a broader point that fits the Innovators beat. He argues that AI lowers the cost of running an “antiquated” industry by replacing a stack of specialised SaaS tools across the whole value chain. He says that in his prior role he spent millions per year on specialised software, and he expects a large share of those tools to become unnecessary as teams build from basic AI primitives and open source components.

He described the early internet as directed. People knew what was missing. They wanted communities, comments, and places to post work, and they built them from scratch because the infrastructure did not exist yet. Now, he says, you can recreate 95 percent of those platforms in a weekend. The hard part is not building the tool, it is making it matter.

That is where his argument gets uncomfortable. Virality used to ride on something raw and human, and he thinks AI breaks the default assumption that what you are seeing is real. His view is that we are moving into a world where you should assume media is inauthentic until it is proven otherwise. That shift changes what spreads, what people trust, and how creators feel about putting work into the world.

Layer is his response. It is a hardware company, a digital art display built to treat generative and kinetic art like fine art, not like a TV on a wall. He told me the idea grew out of an identity crash after leaving DeviantArt, and a simple desire, he wanted the best digital art on his own wall, presented correctly. He went looking for a product that did it, and he says he could not find one, so he built it.

He also does not sugarcoat how hard hardware is. He told me getting a manufacturing partner is harder than raising venture capital, because the manufacturers that can actually deliver are not built for startups, and you have to earn your way into their calendar. That challenge is part of what pulled him back into building in the first place. He missed meeting people, the artists, the founders, the operators in labs, the whole human mess that comes with making something real.

The Keep Going part of this episode is not “follow your passion.” It is more specific. Angelo is making a bet that digital art is going mainstream, and that the people who will survive this AI wave are the ones who adapt their craft to what the medium is good at. He said still images should often be printed, because printing is already excellent. Displays should be used for work that moves, especially generative work that does not loop in a way your brain gets tired of. He thinks that kind of work will define the century.

He is not naïve about the cost. He said illustrators are suffering and that many jobs are gone, and he widened it to the broader creative class, designers and builders getting hit by tools that shrink teams overnight. Still, he ended with the only kind of optimism that counts, the practical kind. Creative people adapt. They always have.

On this episode of Innovators, I spoke with the SingFit co-founder and CEO about how her company is using therapeutic music to help people with dementia, traumatic brain injuries, and speech loss. The idea sounds almost deceptively simple. People who lose the ability to speak can often still sing. Music activates multiple regions of the brain at the same time, creating pathways that normal speech sometimes cannot access.

SingFit turns that principle into software.

The platform recreates part of what music therapists do in clinical settings. Songs include lyric prompts, guided vocal tracks, and structured timing designed to encourage participation and cognitive engagement. The result is something that can be used not just by trained therapists, but by caregivers, nursing assistants, and families at home.

Francine said the company now operates in more than 10,000 skilled nursing and senior living centers across the United States. The company recently launched a caregiver-focused version with AARP aimed at helping families support loved ones at home.

One of the more interesting parts of the conversation was how deeply personal the company’s origin story is. The original idea came from Francine’s father, an inventor and former opera student who was fascinated by the role of lyric prompters in live performance. He imagined a system that could feed people lyrics in real time long before the technology existed to build it.

Years later, Francine’s brother became a music therapist after seeing a friend recover from a traumatic brain injury and emerge from a coma mouthing the words to “Wish You Were Here.”

That combination of therapy, family history, and technology became the foundation for SingFit.

Francine also made an important point about startups in healthcare and assistive technology. Too many founders start with technology instead of problems. Her advice was direct. Find a real problem first, then build the system around solving it.

In SingFit’s case, the company focused on one issue inside dementia care: social isolation. Patients often begin withdrawing socially as their condition progresses, which can accelerate decline and increase care costs. The platform was designed to create engagement, connection, and routine through music.

The broader issue she kept returning to was aging. Dementia care, caregiver support, and cognitive decline remain massively underserved compared to other parts of healthcare. Francine pointed out that only a handful of dementia drugs have been approved over the past century while cancer treatments continue advancing rapidly.

Music may not solve dementia. But the company is betting that engagement, memory, rhythm, and emotional connection can improve quality of life in ways that medicine alone often cannot.

And honestly, there is something refreshing about hearing a founder talk about care instead of scale for once.

Success is rarely a clean break. It is usually a slow crawl out of fear.

On this week’s episode of Keep Going, Melissa talks about leaving abuse, learning how to speak up again, and building an event planning business after losing everything.

“I believed that I was nothing,” she said. “I believed that someone else had to control my mind because that was what I was told for over 17 years.”

That damage does not disappear overnight. Melissa described the strange process of learning how to trust herself again. First she decorated rooms for family and friends. Then she started charging for it. Then she had to learn something even harder, valuing her own work.

“Doing it for free was the easy part,” she said. “When you was trying to charge for it, it became a bit of a challenge.”

What stood out in the conversation was how practical her advice became. There was no fantasy about instant success. She talked about systems. Contracts. Pricing. Schedules. Learning skills properly instead of pretending you already know everything.

When she started her decorating company, she signed up for classes because she wanted to understand the work deeply. “Don’t just wing it,” she said. “Learn the industry.”

Then the pandemic arrived and destroyed the in-person event business almost overnight. Instead of treating it as the end, she pivoted into virtual events, books, speaking, and media work. That shift became another lesson. The thing that feels like collapse is sometimes just a forced change in direction.

One of the strongest parts of the interview came when Melissa described being a single mother with no place to live. She talked about asking for help, finding an apartment she did not want but turning it into a home, and writing down what she wanted her future to look like even when nothing around her matched it yet.

That mattered because her story is not really about motivation. It is about momentum.

She believes people wait too long for confidence before they act. Her argument is almost the reverse. You move first. Confidence follows later.

“Don’t wait for everything to be perfect for you to take that step,” she said. “You will stumble. Forgive yourself for stumbling. And keep going.”

Melissa’s upcoming memoir, The Life I Designed, comes out in October. The title fits the conversation perfectly. Her life was not handed to her in a finished form. She had to build it piece by piece, often while exhausted, scared, and unsure of what would happen next.

A lot of people think reinvention belongs to younger people. Melissa’s story argues the opposite. Reinvention belongs to anybody willing to keep moving after the world tells them to stop.

You can check out all of Melissa’s work on her jam-packed website and book some time with her here.

Before he built six companies, before the bestselling books and the keynote stages, he was teaching biology and physics. He had an idea for an airplane design and wanted to turn it into a business. The problem was simple. He had never taken a business class in his life. He was scared of failing.

But he realized something else scared him more. He did not want to become an old man who never tried. The fear of regret outweighed the fear of failure.

That idea sits underneath almost everything he talks about now. Most people think entrepreneurs are fearless. They are not. They are just more afraid of standing still than moving forward.

Burrus also said something I had never heard framed quite this way before. He said entrepreneurs usually have success metrics but almost never have failure metrics.

He gave the example of hiring someone you know is not right for the role. Deep down you know it after a week, but you spend months trying to fix it before finally letting them go. You already saw the failure coming. You just delayed acting on it.

That applies to almost everything. Businesses. Projects. Careers. Relationships. We hold onto broken things because motion feels harder than denial.

A lot of the conversation focused on AI, which Burrus sees less as a replacement for people and more as an amplifier. He argued that companies are making a mistake by focusing only on the tools. First comes mindset, then skillset, then toolset. Most firms skip directly to the software and never rethink how they actually work.

He also pushed back on the panic around AI replacing everyone. His point was simple. Jobs have always changed. The danger is not the technology itself. The danger is pretending your current role will stay frozen forever.

One line stuck with me. “You can only coast downhill.”

That feels true right now. A lot of people are waiting for stability to return before they adapt. But the stable version of the world they remember is probably not coming back. The people who do well over the next decade will likely be the ones willing to relearn things while everyone else argues online about whether change should exist at all.

Burrus is relentlessly optimistic, sometimes almost aggressively so. Normally that kind of thing annoys me. But his optimism is grounded in systems and patterns, not motivational slogans. He studies technology, demographics, and behavior and asks what becomes inevitable once those things start moving together.

His broader point was that most people underestimate the future because they spend too much time staring at the present. Burrus is a unique thinker in that he sees where the puck has gone and where it is going… years and years into the future.

You can check out his books here and hire him at his website.

On this episode of Innovators, I spoke with Judickas, VP of Strategic Alliances at IPXO, a company building what is essentially a marketplace for internet infrastructure. IPXO leases IPv4 addresses from companies that have large unused reserves to startups, hosting firms, telecoms, and AI companies that need them to operate. It sounds obscure at first, but the deeper we got into the conversation, the more it started to resemble real estate.

Back in the early days of the internet, engineers assumed 4.3 billion IPv4 addresses would be more than enough. Instead, the modern internet burned through them. Companies that arrived early, IBM, Apple, major telecoms, ended up sitting on massive blocks of addresses, while newer firms often struggle to get even a few hundred.

Judickas explained how IPXO emerged from that imbalance. The founders originally ran a hosting company and began leasing their own unused IP addresses to customers. Demand exploded almost immediately. That experiment eventually became a global marketplace that now manages millions of addresses.

What makes the story interesting is that the business is not really about software alone. It is about trust. Judickas described the challenge of convincing large enterprises that the IP addresses sitting idle on their books could become a revenue stream. In many cases, companies did not even realize those assets had value.

We also talked about the strange half-finished migration from IPv4 to IPv6. For decades, the industry has talked about replacing IPv4 entirely, yet much of the internet still depends on it. Judickas sees a world where both systems coexist for years to come, especially as AI systems and connected devices increase demand for network infrastructure.

The conversation eventually turned toward AI. Every AI endpoint needs connectivity. Every distributed system needs addresses. Judickas believes the next wave of infrastructure demand will come not from traditional hosting companies but from AI firms gathering data, training systems, and deploying agents across the web.

There is something almost invisible about this market. Most people never think about the plumbing underneath the internet until it starts running short. But scarcity changes behavior. IPXO is betting that IP addresses will increasingly behave less like technical resources and more like financial assets, leased, managed, and traded much like commercial property.

It sounds harsh at first. But the more he talked, the more it made sense.

Gillen’s life did not begin in anything close to stability. He described being abandoned as a child in Ireland during the violence of the Troubles before being moved to London’s East End, where he was eventually pulled into organized crime at a young age. He spent years in prison, including long stretches in solitary confinement.

Today he runs companies, advises brands, works in television and film, and moves through circles that would have seemed impossible from the position he started in.

What interested me most was not the redemption arc. Everybody loves a redemption story because it makes life feel orderly. The thing that interested me was how practical his thinking is now. He talks less like a motivational speaker and more like somebody who learned survival the hard way and simply translated it into business.

At one point he described entrepreneurship as the most powerful form of personal growth he knows. Not because business is glamorous, but because it forces you to confront yourself constantly. Your habits matter. Your discipline matters. Your ability to finish things matters.

That word kept coming up. Finish.

He said many people are not finishers. They get excited at the beginning, panic during the middle, and disappear before the hard part is over. Gillen’s view is that finishing is not really about talent. It is about deciding there is no acceptable path backward.

He also had a line that felt brutally accurate. “Challenge is only growth trying to happen.”

Most people interpret resistance as a sign to stop. A failed deal, a bad quarter, rejection, debt, embarrassment. His argument is almost the opposite. Resistance is often proof that you are finally pushing against something real.

There was also something interesting in the way he talked about criminal life. He did not romanticize it at all. In fact he sounded exhausted by it. He described it as people searching for survival, belonging, and identity in the wrong place. The money and status look attractive from the outside, especially when you are young and broke, but he was clear that it only leads to bad endings.

The strangest part of the conversation was hearing him move seamlessly between stories about prison and stories about working with Sean Bean and Orlando Bloom on television projects. But maybe that is the point. People are rarely one thing forever. A life can split hard in another direction if somebody decides to keep moving long enough.

And honestly, that may be the real theme of Keep Going anyway.

Not perfection. Not reinvention. Just motion.

Some people stop where they started. Others refuse to.

Next week I’ll be helping to host the Generated Awards, the first AI video awards show on the planet. It’s going to be an amazing time with AI video creators, marketers, and artists who will join together to celebrate a brand-new medium of expression. I’d like you to attend. There are two options. Feel free to RSVP to both.

Read more

Lu is the co-founder and COO of Memoket, a startup building what she describes as a “context layer” between the physical world and AI. The company’s product combines a wearable recording device with software that tracks conversations and projects across time. Instead of generating isolated meeting summaries, Memoket tries to reconstruct relationships, decisions, and discussions as they evolve.

“The core idea is not just summarizing one meeting after another,” Lu said on The Innovators podcast. “What we want to provide is the full picture.”

The system works by recording conversations throughout the day, then using AI to organize and connect information over weeks or months. If a salesperson meets a client multiple times, the AI can track changes in requirements and priorities. If a founder interviews ten customers, the software can compare responses automatically instead of forcing someone to read ten separate reports.

Lu said the idea came from frustration with current AI note-taking tools, which often treat every conversation as a separate event.

“In the past, the AI note takers would give me ten reports,” she said. “I had to read through them and piece everything together myself.”

The company also sits in the middle of a growing debate over AI, privacy, and always-on recording. Lu argues that AI systems need better access to real-world context if they are going to become more useful over the long term. At the same time, she acknowledged the sensitivity of recording personal information and said users control whether data is uploaded or analyzed.

One use case Lu described involved helping her mother keep track of conversations with doctors.

“My mom is not able to repeat all that information to me word by word,” she said. “So I have her record the conversation.”

Unlike many AI tools built entirely around smartphones or laptops, Memoket also includes custom hardware. The wearable device can be worn as a wristband, pendant, or clip and allows users to start recording with a single button press.

Lu said the hardware became necessary because many important conversations happen away from screens.

“Sometimes I’m driving and an investor calls,” she said. “I wish I could record that, but I’m not going to risk my life reaching out to the phone.”

Memoket is currently recruiting beta users ahead of launch and they just launched their ProductHunt where you can find more info.

Chen is the co founder and CEO of Verdi Agriculture, and he describes the company as “physical AI for farm infrastructure,” starting with irrigation. The pitch is not about tractors or drones. It is about the pipes, valves, pumps, and filter stations that farms rely on every day, and that most farms still run by hand. Chen says about 95 percent of farms still operate this stuff manually, with workers walking fields to check equipment and turn things on and off.

Verdi’s approach is retrofit. Instead of asking a farm to rip out infrastructure and install a bespoke automation system, Chen says Verdi builds modular devices that sit on top of what is already there and make it “smart.” The same core idea can be applied across equipment, from pipes and valves to filter stations and even sulfur burners. The benefit is not just efficiency. It is reducing repetitive field work that eats time and labor.

I asked what makes this hard, because the parts sound like commodity hardware. Chen’s answer was that the hardware is only half the story. The real complexity is in the software and firmware that lets devices act as a fleet. Irrigation is not as simple as flipping a valve. He pointed to hydraulic constraints, open a valve too early or too late and you can run out of water, or blow something up. Verdi’s system coordinates sequences so farms can automate without breaking infrastructure.

The reason he cares is personal. Chen said the founding team comes from farming families, and that the work is driven by what they have seen up close, rising labor costs, water scarcity, and extreme weather that makes farming less predictable. His view is that the point of better infrastructure is resilience, keeping food production stable even as conditions get worse.

Hardware is also a fundraising problem, so I asked how they raised. Chen framed the product as “digital labor,” a substitute for human labor on repetitive operational tasks. He said Verdi has shown enough adoption in a tough market to bring in investors, including hard tech and climate focused funds.

Verdi is working in a corner of agriculture that Chen says has been overlooked. John Deere and others are heavily digitized, but in mobile machinery. Irrigation infrastructure is still mostly analog, and even where automation exists it has tended to be expensive and custom, which is why adoption is low. Chen said there are a couple of companies building into this segment, but he sees the 95 percent of farms that are not automated as the real market.

A big part of the strategy is usability. Farmers and farm operators are not sitting in front of spreadsheets all day. They are dealing with immediate problems in the field. Chen said Verdi is built for the everyday operator, not the farm engineer. The product is meant to offload the constant equipment checking and troubleshooting so people can focus on the work that actually needs human judgment.

On go to market, Chen said agriculture is still relationship driven, but door to door selling and trade shows do not scale. Verdi uses outbound sales built around registries and databases to target the growers where they can have the most impact. He also said they use satellite data to enrich lead targeting and understand needs by region. At the same time, he said inbound demand matters because growers want agency, they want to choose tools, not be shoved into them.

When I asked what success looks like, Chen said he expects farms to look different in ten years. Not just irrigation, but every piece of infrastructure, processing buildings, power systems, and basic plumbing, will be smart in some way. He pointed to the size of the agricultural equipment market to make the case that infrastructure can support a very large company, and he wants Verdi to be that company on the infrastructure side.

He also has a second obsession, finance. Chen said agriculture lacks the kind of project finance and structured financing instruments that helped scale clean energy. He thinks there is room for fintech built specifically for agriculture, to finance the upgrade cycle that resilience requires.

Verdi is currently focused on the west coast of North America, the US and Canada, and is expanding across the continent, into Mexico, and into Latin America later this year. Chen said sales grew about 16x over the past year. He said the company is not raising right now and expects to raise a Series A in early 2027.

Before he built six companies, before the bestselling books and the keynote stages, he was teaching biology and physics. He had an idea for an airplane design and wanted to turn it into a business. The problem was simple. He had never taken a business class in his life. He was scared of failing.

But he realized something else scared him more. He did not want to become an old man who never tried. The fear of regret outweighed the fear of failure.

That idea sits underneath almost everything he talks about now. Most people think entrepreneurs are fearless. They are not. They are just more afraid of standing still than moving forward.

Burrus also said something I had never heard framed quite this way before. He said entrepreneurs usually have success metrics but almost never have failure metrics.

He gave the example of hiring someone you know is not right for the role. Deep down you know it after a week, but you spend months trying to fix it before finally letting them go. You already saw the failure coming. You just delayed acting on it.

That applies to almost everything. Businesses. Projects. Careers. Relationships. We hold onto broken things because motion feels harder than denial.

A lot of the conversation focused on AI, which Burrus sees less as a replacement for people and more as an amplifier. He argued that companies are making a mistake by focusing only on the tools. First comes mindset, then skillset, then toolset. Most firms skip directly to the software and never rethink how they actually work.

He also pushed back on the panic around AI replacing everyone. His point was simple. Jobs have always changed. The danger is not the technology itself. The danger is pretending your current role will stay frozen forever.

One line stuck with me. “You can only coast downhill.”

That feels true right now. A lot of people are waiting for stability to return before they adapt. But the stable version of the world they remember is probably not coming back. The people who do well over the next decade will likely be the ones willing to relearn things while everyone else argues online about whether change should exist at all.

Burrus is relentlessly optimistic, sometimes almost aggressively so. Normally that kind of thing annoys me. But his optimism is grounded in systems and patterns, not motivational slogans. He studies technology, demographics, and behavior and asks what becomes inevitable once those things start moving together.

His broader point was that most people underestimate the future because they spend too much time staring at the present. Burrus is a unique thinker in that he sees where the puck has gone and where it is going… years and years into the future.

You can check out his books here and hire him at his website.

I spoke with Jae Lee, a founder on his eighth startup, and what stayed with me was not the wins. It was the pattern. He did not begin with some grand plan. He saw problems that were right in front of him. A school without a website. A publisher with a bad one. He built something. Then he did it again. And again.

That sounds clean when you say it fast. It is not clean when you live it.

Four of his companies failed. Not soft failures. Real ones. Money lost. Time gone. Teams broken. And the cause was not market timing or tech. It was people. Bad hires. Missed signals. Ignored warnings. The kind of mistakes that do not show up in pitch decks but end companies all the same.

He said something worth sitting with. Feedback is a gift. You do not have to like it. But you should ask who gave it and why. Most founders say they want honesty. Few actually take it when it costs them something.

There is also this idea that founders are always right. He believes that. I think he is half right. The founder makes the call. That is the job. But being right in that sense just means you own the outcome. It does not mean the call was good.

Then the world steps in.

He was building in the Gulf. Deals in motion. Meetings lined up. Real traction. Then conflict hit the region. Plans stopped. Movement slowed. Momentum broke. He was not even in the blast zone, but it did not matter. The system around him changed. That is the part people do not like to admit. You can do everything right and still get knocked sideways.

So what do you do when the ground shifts?

You adjust. Not in a dramatic way. Not with some heroic pivot story. You narrow the focus. You pick a tighter problem. In his case, from general building management to data centers. Same direction, smaller target. You keep moving.

That is the through line here. Not brilliance. Not luck. Endurance with small corrections.

I asked him why he keeps doing this. Why not take the safe route. He gave a simple answer. One life. One shot. He wants to leave something behind that shows he helped people move forward in their work. Not money. Not status. Influence in the practical sense.

You can agree with that or not. But it explains the behavior.

Most people want control. Founders learn, slowly, that control is thin. You do not control markets. You do not control timing. You barely control your own reactions some days. What you control is whether you keep going when the easy path is to stop.

That is the job.

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 ke…

Read more

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 conve…

Read more

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.