I wanted remind you that I’m working with founders, CEOs, and industry experts to turn what they know into an audience and, more importantly, real influence.

I’ve been doing this with a handful of founders already, mostly through informal coaching. The setup is simple. We talk once a week for about 30 minutes, figure out what you should be saying and where you should be saying it, and then work on making it happen.

That can include Substack, blog posts, press releases, media training, SEO/GEO, social media, media outreach, and general marketing. The point isn’t to throw content onto the Internet. It’s to make sure the right people know who you are and why your work matters.

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So far, I’ve helped people build newsletters with 25,000 readers, grow Twitter accounts to more than 500,000 followers, create huge Discord communities, land international press, and host dinners with journalists at major industry events.

I’m not trying to become your PR agency or your full-time CMO. Think of me as a coach and an extra set of experienced eyes. I’ll help you figure out what works, what doesn’t, and what you should be doing next.

The introductory package is $1,500 per month in which we do a 30 minute consult and build you an Substack and media strategy with one post per week. Given what most marketing and PR firms charge, I think that’s pretty reasonable. More importantly, I want this to be useful for founders who are still building.

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That option is for founders who know they need to be publishing regularly but simply don’t have the time to do it themselves.

The bottom line is pretty simple. I want to use what I’ve learned over the years to help smart people get noticed, while also making a living as a freelancer.

If either package sounds useful, email me at john@biggs.cc. I’d be happy to talk.

On this episode of Keep Going, I spoke with Dorothy Belshaw, CEO and co-founder of Rockview Management Group, which recently acquired NY NOW, the New York gift and home furnishings trade show.

At its peak, the show occupied more than 500,000 square feet of exhibition space at the Javits Center. But years of ownership changes, shifting strategies and the COVID pandemic took their toll. When Belshaw acquired the show, attendance had been declining for years and the event was a fraction of its former size.

Rather than starting a new event, Belshaw saw value in the existing business, including its brand, buyer and exhibitor relationships and established place in the industry’s buying calendar. She also saw an opportunity to run it differently, with a small team that could make decisions quickly and work directly with customers.

The early results are encouraging. After just three months under the new ownership, the August show grew slightly in size and attendance increased 5%, reversing years of decline.

We talked about what it takes to rebuild a struggling business, why physical trade shows still matter in a digital world and how small brands can decide when they’re ready to move from direct-to-consumer sales into wholesale.

It’s a conversation about taking an established business, treating it like a startup and finding out whether personal relationships and faster decisions can bring it back.

On this episode of Keep Going, I spoke with Argueta, co-founder and CMO of Bailey’s CBD for Pets, about what happens when your payment processors stop working, your competitors have millions of dollars and you spend your days visiting pet stores that have absolutely no interest in what you’re selling.

The story actually begins with music. Argueta and Jay met while touring in bands in 2013. Both had experience with California’s cannabis industry, and Jay had begun experimenting with CBD extracts at a time when the market was still developing. Customers occasionally asked whether he had something similar for their dogs, so he put together a product with his pug Bailey’s face on the label.

The first batch consisted of just 50 bottles made in Jay’s kitchen. The response convinced them that there might be a real business there, and the two eventually reunited to launch Bailey’s CBD for Pets.

Then things got difficult.

When the money stopped coming in

The period between 2018 and 2020 was particularly brutal for Bailey’s. Following the passage of the 2018 Farm Bill, CBD businesses were entering the market rapidly, but financial services companies remained reluctant to work with them.

Argueta described how one payment processor, Elavon, abruptly stopped servicing smaller CBD businesses in 2019. Bailey’s lost its ability to process conventional credit card payments and relied on PayPal, which subsequently shut down its account as well.

The company suddenly had a serious problem. It could make products and find customers, but collecting payments online had become extremely difficult. Worse, payment providers could hold funds for months, leaving the founders without working capital.

At roughly the same time, California dispensaries began dropping hemp-derived CBD products because of regulatory restrictions. The company was losing sales channels just as competition was becoming more intense.

And this wasn’t a market filled exclusively with small startups. Argueta recalled competing against CBD brands associated with Martha Stewart, Willie Nelson and other famous names with considerably more money to spend.

For a business that had started with a few hundred dollars, those were difficult odds.

Twenty-five stores and not a single sale

Argueta’s response was to sell the old-fashioned way. He drove around Los Angeles and Orange County visiting pet stores, pitching products and trying to persuade owners to carry Bailey’s.

Some days he visited 20 or 25 stores without securing a single account. Retailers were already overwhelmed with competing CBD products, and many were skeptical about the category altogether.

Weekends weren’t much easier. Argueta and Jay attended farmers markets, dog events and retail pop-ups, selling products directly and explaining what CBD was supposed to do. Sometimes they would spend hours at a store that already carried their products without generating much interest.

Argueta admitted that the constant rejection was disheartening. What helped was a community of other entrepreneurs facing similar problems, along with a determination to keep the business operating as cheaply as possible.

They reduced expenses, took modest salaries and reinvested what they could. In the early days, Argueta said, there were times when even finding money for lunch was a concern. The founders also took on side work to bring in extra cash.

Their strategy was relatively simple: survive long enough for the market to settle down.

And eventually, it did.

At the SuperZoo pet industry trade show in 2019, Argueta remembers seeing more than a hundred businesses offering CBD products. By 2022 and 2023, that number had declined considerably. At the most recent show, he estimated there were fewer than ten.

Many competitors had disappeared. Bailey’s was still there.

Finding a business beyond CBD

Survival alone wasn’t enough. The company also had to find new ways to grow in a crowded market.

One important change was moving away from generic CBD dog treats toward products marketed for specific purposes, including calming and hip and joint support. These formulations incorporated additional ingredients and gave customers a clearer understanding of their intended use.

Argueta believes they should have made that change earlier. Instead of expecting customers to understand CBD and determine why they might want it, the company could explain what each product was designed for.

Bailey’s also expanded beyond CBD into products such as probiotic chews and mushroom-based supplements. That opened sales channels that remained unavailable to CBD products, including certain wholesale marketplaces.

Another opportunity came from manufacturing products for other brands. Argueta recalled losing an early contract because Bailey’s wasn’t organised to handle it. Rather than ignore the opportunity, the founders spent years building a private-label and contract-manufacturing operation. Today, he said, the company works with about eight consistent clients.

It’s an interesting development for a business that once struggled to compete with other CBD brands. Now, some of its revenue comes from helping other companies make their own products.

The problems haven’t disappeared

Bailey’s still faces restrictions on advertising and distribution, and Argueta described the difficulties of competing for attention on Google when many major retail platforms don’t allow CBD products.

The company has consequently invested heavily in organic search, blogging and website development rather than depending entirely on paid advertising.

There have also been regulatory problems. Argueta said Bailey’s received an FDA warning letter roughly a year and a half before our conversation and has been working through the agency’s concerns. He described a slow process of submitting changes and waiting for responses, with the warning letter creating additional concerns among retailers and customers.

These are reminders that surviving the initial wave of competition doesn’t mean the business suddenly becomes easy.

But the company has also found opportunities. Argueta said sales grew significantly during the COVID-19 pandemic as more people adopted pets and sought products marketed for calming and wellness. More recently, Bailey’s has been expanding its affiliate relationships and looking for additional distribution channels.

Why keep going?

I asked Argueta why he and Jay were still building a CBD company when they could have moved into an entirely different business.

His answer was the pet industry itself. Both founders enjoy working with pet owners, and Argueta said the customer feedback they receive continues to motivate them. He also spoke about Bailey, the original pug who inspired the business and died in 2024.

The dog may be gone, but the company still carries his name.

What I found most interesting about Argueta’s story is how little of it involves a sudden breakthrough. There was no enormous investment that solved everything, no single marketing campaign that transformed the business and no moment when the founders could stop worrying about money.

Instead, they kept expenses low, found alternative ways to sell their products, built relationships with other operators and gradually expanded into new areas of the industry.

A lot of their competitors didn’t make it through the difficult years. Bailey’s did, and that gave the company an opportunity to keep growing.

Dyson, whose forthcoming book In Defense of Limits: Human Time and AI Scale examines the relationship between human life and technological growth, believes that American society has become increasingly focused on making money rather than creating value. People see enormous fortunes being made through cryptocurrency, financial speculation, and technology companies while ordinary workers struggle to get by. The result is a growing sense that the system is unfair and that individual effort no longer matters.

One of Dyson’s central concerns is what she calls “information diabetes.” Just as processed food can damage physical health, she argues that a constant stream of simplified, fragmented information can damage our ability to think critically. AI-generated summaries, social media feeds, and business presentations filled with impressive numbers but little context encourage people to consume information without understanding it.

She sees a similar problem in what she calls “money diabetes,” the accumulation of wealth through systems that extract money from other people’s activities without producing much value themselves. The problem isn’t capitalism itself, she argues, but a culture that increasingly treats financial success as proof that something is worthwhile.

That concern extends to artificial intelligence. Dyson is less worried about machines becoming powerful enough to destroy humanity than about companies using AI to keep people dependent on their products. “I’m not worried about predatory AI, I’m worried about parasitic AI,” she says. These systems don’t need to destroy their users. They simply need to keep collecting small amounts of money, time, and attention from them.

The conversation also turns to the growing loss of human agency. Dyson compares modern society to the social structure of medieval Europe, where a small ruling class held most of the power while ordinary people had little control over their lives. Today, she argues, many people feel similarly powerless in the face of governments, technology companies, and financial institutions.

One possible response is what Dyson calls universal basic service. Rather than simply giving people money, she proposes a period of paid public service for young adults. Participants could work in parks, schools, public facilities, or other community settings, gaining experience while working alongside people from different backgrounds. The goal would be to restore a sense of shared responsibility and remind people that their time and attention have real value.

Dyson also questions the modern obsession with eliminating friction from everyday life. Technology companies promise to make everything faster, easier, and more efficient, but not every difficult experience needs to be removed. Building relationships, raising children, learning new skills, and helping other people all require effort. That effort is often what makes those experiences meaningful.

Despite her concerns, Dyson remains hopeful. She believes people are beginning to recognize the costs of systems that put growth and profit ahead of human well-being. Parents are questioning the effects of social media on their children, communities are demanding more control over decisions that affect them, and governments are slowly responding.

When asked why people should still have hope, Dyson offers a simple answer: “because we’re still fighting.”

For Dyson, progress isn’t about reaching a perfect future where every problem has been solved. It’s about doing useful work, making things better for other people, and passing that work along to the next generation. No individual can fix everything, but everyone can contribute to something worthwhile.

In this episode of Keep Going, we talk about AI, cryptocurrency, inequality, public service, the value of human connection, and why the effort to improve the world matters more than any promise of a perfect future.

On this week’s Keep Going, I talk with Alan Wexelblat, a longtime software engineer, UX leader, startup veteran, and MIT Media Lab alum who retired earlier this year. Instead of settling into retirement, Alan began volunteering full-time with organizations supporting immigrants and refugees.

We talk about why he made that choice, what decades of building software taught him about failure, and why he thinks the best time to get involved is when you see something broken and can no longer accept living with it.

We also get into AI and the future of work. Alan argues that AI is very good at producing output, but output isn’t the same thing as an outcome. Human judgment, experience, and an understanding of what people actually need still matter. For people starting careers right now, his advice is simple: stop worrying so much about preserving a job title and start asking where you can bring real value.

It’s a conversation about work, retirement, technology, responsibility, and what success looks like after the résumé stops mattering.

I went into my first mushroom session as a skeptic. I hated the culture around psychedelics, distrusted the idea of calling them “medicine,” and had no interest in spiritual revelations. I was also burned out, grieving my father, drinking too much, and struggling to feel much of anything. Six hours later, something had shifted. That night sent me lookin…

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I went into my first mushroom session as a skeptic. I hated the culture around psychedelics, distrusted the idea of calling them “medicine,” and had no interest in spiritual revelations. I was also burned out, grieving my father, drinking too much, and struggling to feel much of anything. Six hours later, something had shifted. That night sent me lookin…

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On this week’s Keep Going, I talk with Reid Robinson, founder of Robinson Exotech Corp. and creator of the X Leg, a wearable exoskeleton designed as a hands-free alternative to crutches. The idea came out of Robinson’s own recovery after a serious car crash in 2015 shattered his lower leg and ankle. Over the next two and a half years, he went through 13 surgeries while doctors tried to save his leg.

Between surgeries, Robinson started wondering why there wasn’t a better way to remain mobile without putting weight on an injured leg. He sketched an idea, searched for an existing product and, when he couldn’t find one, decided to build it himself. The first X Leg was made in his garage from cut-up crutches, Home Depot aluminum, leather belts and an IKEA cutting board. It looked rough, but it allowed Robinson to cross the street and play soccer with his kids while his injured leg still couldn’t support even five pounds.

That prototype turned into five years of research and development. Robinson tested five versions, worked with local patients and eventually secured patents in several countries. X Leg began selling in 2021, but Robinson continued working his IT job while running the company during evenings, weekends and lunch breaks. Until May of this year, he describes himself as effectively working three jobs: being a father, working in IT and building X Leg.

This is the part of entrepreneurship that we don’t talk about enough. There is a popular idea that persistence is automatically admirable, but sometimes continuing with a company that isn’t working is simply wasting another year. I’ve talked to thousands of entrepreneurs, and after a decade of slow progress I would normally tell someone to seriously consider whether it is time to stop.

Robinson’s story is different because there are signs that the underlying product works for at least some customers. People actively search it out after other mobility devices haven’t worked for them, and Robinson says customer messages about what they were able to do while using X Leg have kept him going during difficult periods. One customer told him the device allowed him to attend his daughter’s wedding in Europe.

The problem is getting the product into the existing medical system. X Leg is still relatively expensive, isn’t automatically covered by insurance and needs more clinical evidence before Robinson can pursue the kind of dedicated insurance coverage that could make it easier for patients to obtain. Studies are underway or being planned in the US, Chile and Canada, and Robinson hopes those results will eventually help move X Leg toward standard care.

Robinson has spent ten years trying to turn something he built for himself into something other people can use. There is still no guarantee that X Leg becomes a large company, and Robinson is very clear that the device doesn’t work for every injury. But there is an important distinction between blindly refusing to quit and continuing because customers keep giving you evidence that the thing you built solves a real problem.

That’s what makes Robinson’s story interesting. Perseverance only pays when there is something worth persevering for.

Joe Spector came to America from the Soviet Union at ten years old. His family arrived with $100 each. Joe had a red suitcase.

He studied his way into Berkeley, finished in three years, and landed a job at JP Morgan. It was the kind of secure, prestigious career his younger self thought meant he had made it.

Then he realized he didn’t care about it.

Joe left finance, moved into startups, and eventually helped build Hims, taking an idea around hair loss and sexual health and turning it into a public company.

Then he left again.

During COVID, a $2,000 emergency vet bill for his dog made him start asking questions about veterinary care. He took what he had learned building Hims and started Dutch, a pet telehealth company aimed at making veterinary care easier and less expensive.

But one of Joe’s first lessons at Dutch was that past success does not give you a perfect playbook for the next company. He initially tried to copy the Hims model. It didn’t work. Pet care was different. So he changed the model and kept building.

Joe’s story is about more than startups. It’s about refusing to confuse security with purpose. Sometimes the thing you worked years to reach turns out to be a place you need to leave.

On this episode of Keep Going, Joe and I talk about immigration, Wall Street, building Hims, starting over with Dutch, getting things wrong, and why being an outsider can make taking risks a little easier.

And we return to that ten-year-old boy carrying a red suitcase into a new country.

What would Joe tell him today?

Give yourself the freedom to look beyond what you think you need right now. There may be a much bigger life outside the path you can currently see.

In February 2006, Steve Jobs took the stage at Apple and announced that the company was about to reinvent the home stereo.

During his presentation, he talked about the iPod. By 2006, iPods were a huge business. Apple was making $8 billion a year on the devices, and it was selling millions a quarter. This meant they were everywhere. People were carrying t…

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What does success look like after 25 years in business?

On this episode of Keep Going, I talk with Scott Jordan, founder of SCOTTeVEST and self-described “Chief Pocket Scientist,” about building a clothing company around a simple idea: people carrying a growing pile of technology needed somewhere to put it. Long before the iPhone, Scott was making vests for people hauling around Palm Pilots, Discmen, phones, and other gadgets.

But the past 25 years haven’t been a straight line up. Scott talks about watching sales grind to a halt after September 11, betting heavily on publicity that failed to produce sales, losing millions during a bad stretch of television advertising, fighting legal battles, and facing moments when financing nearly disappeared. Through all of it, he kept returning to one basic rule: the company had to make money. Instead of chasing investors, he focused on profitability and built from there.

Today, SCOTTeVEST is a multimillion-dollar company that Scott says operates with zero traditional employees. He and his wife Laura have moved much of the company’s work to contractors and outside specialists, creating a very different business from the one he started 25 years ago.

We also talk about why starting a company may be harder today. Scott once built SCOTTeVEST through personal relationships, press coverage, word of mouth, and some wonderfully shameless PR. Now the company can spend around $2,500 a day on Facebook advertising just to generate roughly the same amount in immediate sales.

Most important, Scott talks about giving up the idea that every founder needs to build the next billion-dollar company. After years of thinking about patents, investors, exits, and massive growth, he came to value something simpler: build a profitable company, do the work well, treat customers well, and create a life you actually want to live.

As Scott puts it, sometimes success really is changing the world one pocket at a time.

Ron is the author of an upcoming book, Shop Different, which is in pre-orders now. We got to talk to him before the book launch and I can’t begin to describe how cool it was to talk to someone like him for the pod.

Back to his story. The Apple story turns on one conversation with Steve Jobs. Jobs thought stores could double Apple’s market share from five to ten percent. Johnson told him that was the wrong target. He pointed to the bigger opening, the half of Americans who had never bought a computer, and the fear of technology that kept them out of the category. That changed the entire store strategy. Put the stores where people already shop, in malls, make them big enough to feel like a major brand, and use the space for experiences, not shelves. The front half introduces people to technology, the back half deepens the relationship with support and learning. No commissions, because you cannot teach someone while you are trying to pick their pocket.

Johnson also shares what it looked like when Apple was close to the bottom. In 2002, he says the company hit a point where it was trading at cash value, and Jobs was carrying the weight of a risky transition to Intel, OS X, new apps, and the early store rollout, all at once. He tells a scene from the morning the Soho store opened, when Jobs saw a small line and thought nobody cared anymore. A few hours later the store filled, and Jobs stayed for seven hours, talking to customers and watching the place work. Johnson describes it as a turning point, a moment where the “green shoots” mattered more than the quarterly numbers, and where Jobs doubled down on the stores as a core product, not just a sales channel.

Then it gets harder. Johnson does not dodge JCPenney. He calls it his failure. He explains the vision, a “mall within a mall” with smaller branded shops, a town square feel, and simpler pricing. The mistake, he says, was speed and process. They changed pricing almost immediately, without time to communicate it or bring employees into the build. He contrasts that with Apple, where he could hire the team, shape the culture, and let the model mature. At JCPenney, he never had the internal support needed to make the change stick, and eighteen months later it was over.

This episode is a clean reminder that “great strategy” is not enough. Execution is people, timing, and trust. You can be right about the idea and still lose if the team is not with you and the change moves faster than the organisation can absorb.

This one is personal.

I started working on Shroomies in 2018, after my dad died and I entered one of the darkest periods of my life. I was depressed. I was taking SSRIs. I was very close to self-harm. I didn’t feel like myself, and I didn’t know how to get back.

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Then a friend invited me to a psychedelic mushroom session.

I thought it sounded ridiculous. I’m not a Burning Man guy. I’m not a hippie. I don’t like the Grateful Dead. I definitely don’t like Phish.

But I went.

What happened over the next six hours started a much longer process of figuring out what was happening inside my own head. I eventually had a few more experiences. Things changed. Some changes were good. Some were difficult. But I came out of that period knowing myself better.

Most importantly, I’m still here.

Book Party Fun!

Are you in New York? I’ll be holding a book party in Brooklyn on September 24 and I need a rough headcount so please RSVP here!

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That experience also made me curious. What were these substances actually doing? Why were people using them for depression, PTSD, end of life care, relationships, and creativity? Why had something dismissed for decades suddenly become the subject of serious medical research?

So I started reporting.

The result is Shroomies, a book about psychedelic mushrooms, the people using them, the people studying them, and the strange cultural shift happening around them.

It isn’t an argument that everyone should take mushrooms. Psychedelics carry real risks, and I would never recommend experimenting with them alone. It’s a book about what happens when people who have run out of answers start looking somewhere else.

That feels very close to what Keep Going has always been about. Failure doesn’t always arrive as a failed company or a lost job. Sometimes it is much more subtle. Sometimes is that the status quo stops working for you, that your biggest enemy becomes yourself. Then you have to figure out what comes next. You don’t have to try mushrooms but please try my book.

Shroomies is out today, September 8, in hardcover and on Kindle. If you’re a journalist or simply review books anywhere, I’m happy to send you a copy. Just drop me a line at john@biggs.cc.

I hope you read it.

As always, thank you for listening and supporting me. It means the world.

Buy it now on Amazon

Mohr studied animal science in college. She expected to spend her career working with horses. Instead, she ended up helping solve some of the strange problems that come with trying to change how millions of people shop and live.

On Keep Going, Mohr talked about what she learned along the way. Much of it came down to a simple idea: careers are built as much from the things that go wrong as the things that go right.

You Don’t Need to Know Everything Before You Start

When Mohr joined Amazon’s Alexa smart home team, she had no professional background in smart home technology.

In fact, she didn’t have any smart home devices in her own house.

“I knew nothing about smart home,” she said.

She joined anyway.

She would spend roughly nine years working on Alexa, moving from the early days of asking Alexa to turn lights on and off toward much deeper home automation and personalization.

Her career is a useful answer to one of the questions that stops people from making a move: Am I qualified enough?

Sometimes you aren’t.

The better question may be whether you can become qualified.

Mohr credits part of her success at Amazon to the company’s willingness to put smart people into unfamiliar problems and allow them to figure things out. But that freedom came with responsibility. She had to understand the business, understand its numbers, understand the customer, and learn enough about each new field to make good decisions.

The lesson isn’t to fake expertise. It’s almost the opposite.

Know what you don’t know, then start learning.

Progress Can Be Very Small

Amazon Grocery presented a completely different problem.

Selling books and toys online was one thing. Selling groceries meant dealing with expiration dates, shipping costs, inventory rotation, customer habits, and products that could become worthless before Amazon managed to sell them.

There wasn’t one great idea that fixed everything.

Mohr’s team tested somewhere around 20 or 30 user experience designs. Some worked. Plenty didn’t. Instead of waiting for a single major breakthrough, the team learned to pay attention to small signs that something was getting better.

“Small progress” became something worth building on.

That’s a useful way to think about almost any difficult project.

We tend to want a clear win because wins are easy to understand. You launch the company. You get the job. You sell the product. You hit the number.

Most meaningful work doesn’t happen that cleanly.

You try something. It works a little better. You try again.

Then you keep going.

AI Is Changing Jobs, But That Doesn’t Mean You Stop Learning

Mohr also has a useful view of the current fear around AI and employment.

She doesn’t think AI simply replaces an entire employee in most cases. Instead, she sees it removing parts of jobs.

Maybe 30 percent of someone’s work consists of tasks that aren’t particularly strategic. AI can take some of that work. That lets employees move faster, but it can also allow a company to accomplish the same amount of work with fewer people.

That part shouldn’t be ignored.

Mohr’s response, however, isn’t to resist the technology. It’s to learn how to use it.

Her product teams can now turn an idea into an early app prototype in hours. She looks for job candidates who have experimented with AI and figured out how it can improve their work.

The danger of refusing to experiment with AI, in her view, goes beyond AI itself.

If someone refuses to try a new tool because they don’t like it or don’t understand it, what happens when the next major change arrives?

Technology keeps moving. Careers have to move with it.

You don’t have to believe every claim about AI. You don’t have to use it for everything. But you probably do have to understand it.

Your Passion Might Not Be What You Think

Mohr’s undergraduate degree was in animal science. She expected to become an equine vet.

She also worked in thoroughbred racing after college.

Then she learned something surprising.

Turning something she loved personally into her profession wasn’t necessarily what made work satisfying.

What actually interested her professionally was solving hard problems.

“I think it’s finding something that you’re passionate about, but realizing that passion might not be a personal interest,” she said.

That’s an important distinction.

We’re often told to find the thing we love and make it our job. But loving horses doesn’t mean you have to work with horses. Loving hiking doesn’t mean you need to work for an outdoor company.

You may love solving logistical problems. Or building products. Or fixing organizations. Or working with customers.

Sometimes the subject changes while the kind of work that keeps you interested remains remarkably consistent.

Ask Yourself Where You Failed

One of Mohr’s habits is particularly relevant to Keep Going.

Every year, she conducts a serious review of her own performance.

What did she do well?

Where did she fail her team?

Where did she fail herself?

Where did she fall short of what leadership expected from her?

Then she asks why.

Mohr has brought the same practice into her product teams. Even after a highly successful product launch, she wants a postmortem. Something could have been done better.

This kind of review only works if failure isn’t treated as a verdict.

A mistake gives you information.

Use it.

The Question Mark Email

During her Amazon years, Mohr occasionally received one of Jeff Bezos’s infamous question mark emails.

A customer complaint or some other problem would reach Bezos. He would forward it down the company with a single character:

?

That was enough.

The email would work its way through management. Suddenly everyone knew there was a problem.

Mohr remembers them as terrifying.

She also remembers something else.

Bezos was usually right.

“There was always a bigger gap underneath the question mark email,” she said. The frustrating part was realizing that Bezos had spotted something her team had missed.
Those weren’t the comfortable moments of her career.

Neither were the meetings where she got torn apart. Or the managers she disliked. Or the mistakes she made.

Yet years later, those are often the experiences she values.

“The worst meetings of my life, they’re very memorable to me,” Mohr said.

When everything goes well, she argues, you often don’t improve very much.

She sees the same thing when competing with horses. Winning feels good. Falling off or getting eliminated teaches her more.

That doesn’t mean failure magically becomes pleasant. Mohr is careful about that too. Sometimes it takes a year or two before you can look back at a terrible experience and understand what it gave you.

You don’t need to enjoy the bad meeting.

You don’t need to pretend getting fired, losing, failing, or making a terrible decision feels good.

Give yourself some time.

Then ask what it taught you.

In the mid-2000s, MIT professor Nicholas Negroponte had a wild idea: what if every child in the developing world had a computer? And this wasn’t some smoky gaming cafe or a school computer. It was a machine that the child owned and could use every day. I twas connected to the nascent internet, had a simple operating system, and was rugged enough to surv…

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Hi, again. I took the month off from the podcast but I wanted remind you that I’m working with founders, CEOs, and industry experts to turn what they know into an audience and, more importantly, real influence.

I’ve been doing this with a handful of founders already, mostly through informal coaching. The setup is simple. We talk once a week for about 30 minutes, figure out what you should be saying and where you should be saying it, and then work on making it happen.

That can include Substack, blog posts, press releases, media training, SEO/GEO, social media, media outreach, and general marketing. The point isn’t to throw content onto the Internet. It’s to make sure the right people know who you are and why your work matters.

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I’m doing this with my friend Neeraj Bansal, who handles the operations side. Between us, we have more than 60 years of experience in startups, media, and entrepreneurship.

So far, I’ve helped people build newsletters with 25,000 readers, grow Twitter accounts to more than 500,000 followers, create huge Discord communities, land international press, and host dinners with journalists at major industry events.

I’m not trying to become your PR agency or your full-time CMO. Think of me as a coach and an extra set of experienced eyes. I’ll help you figure out what works, what doesn’t, and what you should be doing next.

The introductory package is $1,000 per month in which we do a 30 minute consult and build you an Substack and media strategy with one post per week. Given what most marketing and PR firms charge, I think that’s pretty reasonable. More importantly, I want this to be useful for founders who are still building.

There’s also a more complete option for people who want us to handle much more of the actual content production and posting. That includes roughly 22 pieces of content each month, including newsletter articles, LinkedIn posts, and short videos for TikTok, Instagram, and LinkedIn.

The introductory rate for that package is $1,500 per month.

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That option is for founders who know they need to be publishing regularly but simply don’t have the time to do it themselves.

The bottom line is pretty simple. I want to use what I’ve learned over the years to help smart people get noticed, while also making a living as a freelancer.

If either package sounds useful, email me at john@biggs.cc. I’d be happy to talk.

Bloop! Bloop!

You remember the sound. It was a cross between a bubble popping and a robot burping, a noise that meant you were about to watch The Daily Show, even if it had aired the night before. It wasn’t live, but it didn’t matter. You had a TiVo.

Today, that seems almost ordinary. Every streaming service remembers where you stopped watching. Every pho…

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Before he was building fintech software for contractors, he was a contractor himself. He started his first business in 2003, spent 15 years working in the field, and grew that business from nothing into an eight-figure company. That is where he saw the pain around checks, credit cards, receivables, and all the little financial tasks that slow down home service businesses.

Kolchin describes iWallet as a new way for contractors to take payments, saving time and money on check processing and credit card processing. But the company is now growing into something bigger: a financial operating system for the home service industry, serving contractors, distributors, and manufacturers.

That matters because home service businesses are still full of old payment workflows. Contractors mail checks, wait on lockboxes, process card payments, chase invoices, and deal with back-office systems that were not really built for the way field service companies operate. iWallet is trying to pull those pieces together in a way that fits how contractors actually work.

Kolchin’s path into software was not straight. He came to the United States in 2002 and started with odd jobs: selling ice cream, washing cars, sweeping the boardwalk in New Jersey, and saving enough money to move to California. A year later, he started his first business.

He liked contracting, but he eventually saw the limits. A contractor can build a good business, but labour does not scale like software. He had already learned that lesson through another startup, a hardware company that built an automated knife-sharpening machine and was later sold. Before that, he had tried a mailbox sensor, manufactured 100 units, launched a Kickstarter, and discovered that having a clever invention was not the same thing as having a market.
That failure taught him one of the oldest startup lessons, but one that still has to be learned the hard way: make something people want.

Kolchin said he originally thought like an inventor. If you had a patent, he believed, people would come looking for it. That was not how it worked. Over time, he learned that the customer matters more than the idea, and that the only way to know what people want is to talk to them directly. Surveys and gated forms are not enough. Real conversations are what count.

For iWallet, that has meant trade shows. Kolchin said trade shows are one of the best places to meet contractors, talk to customers, test messaging, and understand whether the product is solving a real problem. But it only works if you work the room. You cannot sit behind the table and wait. You have to get up, talk to people, explain what you do, and push through the awkward first half hour until the conversations start to flow.

That kind of direct selling is also how you find product-market fit. Kolchin pointed to the idea of the “unaffiliated dollar,” a dollar paid by someone who did not know you six months earlier and bought the product because you convinced them it solved a problem. For him, that was the real test. One unaffiliated customer can become another, and that is where momentum begins.

After years of trying different ideas, Kolchin said iWallet found product-market fit about three years ago, became profitable, and began growing quickly.

The company is now expanding beyond payments. Kolchin said iWallet is working on Repair AI, which he described as something like Harvey for legal or OpenEvidence for medical, but built for the home service space. The company has filed several patents around the idea and sees it as a major opportunity.

At the same time, iWallet is building out more traditional financial products. Accounts receivable is core today, but the roadmap includes accounts payable, checking accounts, credit, and extended warranties. The goal is to give contractors a financial layer that understands their business instead of forcing them to stitch together tools built for everyone else.

There is a simple founder lesson in Kolchin’s story. The first idea may not work. The second may work better. The third may reveal the market. What matters is learning fast enough to stop building only what interests you and start building what people will pay for.

That is what iWallet is doing now. It began with contractor payments. It is becoming a larger financial system for an industry that still runs on too much paper, too many checks, and too many disconnected workflows.

Kolchin built iWallet because he lived the problem. That is often where the best companies start.

Angie Elita Newell does not write easy books.

Her novel, All I See Is Violence, is not a fantasy escape, which she joked about after finding herself surrounded by “sexy fairy” books at BookCon. It is a historical novel built from trauma, archival research, Indigenous memory, and the long shadow of state violence.

Newell is a member of the Liidlii Kue Nation, part of the Dene linguistic group. Her mother was an Air Force pilot. Newell became a historian. Those facts sit close together in her life, but none of them came easily.

On Keep Going, she talked about the residential school system, the Sixties Scoop, and the Canadian government’s removal of Indigenous children from their families. Her mother attended one of those schools, and Newell was later placed in a non-Indigenous household through the assimilationist child welfare system that followed. She described the damage from these policies as “monumental,” and said the goal was to either “annihilate or assimilate.”

That is not abstract history to her. It is family history. It is community history. It is also the ground from which her work grows.

Newell said she became “a very sad child” and then “a very angry teenager.” She dropped out of high school, travelled to Europe, became absorbed in Tolkien and Impressionist art, and eventually made her way to university in the UK after writing short stories for admission. She did not enter academia through the normal door. She found another way in.

That route matters because her work is built around questions most institutions would rather avoid. Why were Indigenous children sent to residential schools? Why were reservations created? Why were treaties broken? Why are some histories documented and others buried? Newell said archival research kept pushing her back to the same question: “Why?”

The answer, for her, is not just to expose trauma. It is to transform it.

When I asked how someone turns pain into art, Newell said the first step is being able to digest it. Trauma can crush a person, she said, but when it can be integrated, it can be “transmute[d] to wisdom.” In its highest form, that wisdom can become art.

That line is the whole interview.

There is pain that breaks people, and there is pain that becomes a kind of knowledge. The difference is not neat. It is not easy. It is not a motivational poster. Newell worked with residential school survivors and Holocaust survivors, and she saw how survival required a capacity to integrate what had happened without being destroyed by it.

Her influences reflect that. She talked about Primo Levi, Hemingway, Picasso’s Guernica, Monet’s darker paintings, and the way art can carry suffering without turning away from it. Great art, in her telling, does not decorate pain. It gives pain a structure strong enough to hold it.

That is what she is doing in All I See Is Violence. The book moves through the Battle of Little Bighorn, Wounded Knee, the 1970s, the Vietnam War, Indigenous warriors, intergenerational trauma, and the violence that repeats itself across time. She said the novel is about 70% factual and that she spent two to three years doing archival research before another historian reviewed it.

The history itself is full of things we are not usually taught. Newell became especially interested after a Cheyenne elder asked her whether she knew there were female warriors. She did not, and that question sent her into the archives. She found evidence that women fought at Little Bighorn and that they fought differently to make up for differences in size and strength.

That is one of the gifts of the conversation. Newell is not interested in flattening history into heroes and villains. She is trained in archival research, but she is also a novelist, so she understands that history is not just dates and documents. It is motive, contradiction, greed, fear, faith, betrayal, survival, and the stories people tell afterward to make themselves feel clean.

She said she tries to approach history neutrally, not by declaring what is good or bad, but by presenting what happened. That does not mean the work is emotionally neutral. It means she respects the reader enough to let the facts carry weight.

What keeps her grounded is not social media or noise. She said she did not have Instagram until her book came out in 2024, and she had not really engaged with YouTube either. Instead, she reads, researches, walks in the woods, eats close to the earth, and stays connected to nature. Her daily life is built around attention.
That matters because attention is a form of survival. Newell’s life could have pushed her toward distraction, bitterness, or collapse. Instead, she built a practice around reading, research, art, elders, history, and language. She followed the thing that kept calling her.

“For me, it’s following your passion,” she said. “Everybody’s gonna have something that you’re really passionate about. And that’s probably a clue that that’s your life’s purpose.”

That may sound simple, but her version is not soft. Following your passion, for Newell, meant walking into some of the darkest archives in North American history and staying there long enough to make something true. It meant looking at the violence directly without letting it define the whole story.

Her next project is about Geronimo, Lozen, Nana, and the Apache resistance. Again, she is drawn to the places where official history has left people out, especially women, medicine people, warriors, and spiritual leaders whose lives were made smaller by the record.

There is a lot of talk now about storytelling, usually in the corporate sense. Tell your story. Own your story. Build your brand.

Newell is doing something older and harder. She is recovering stories that were damaged, hidden, misread, or ignored. She is taking inherited pain and turning it into art, not because art fixes the pain, but because art can keep it from disappearing.

The bottom line?

You take the thing that almost crushed you.

You digest it.

You transmute it.

Then you write.

As I get older, I’m starting to forget everything. Tell me I have a meeting next week? It better be on my calendar. Need me to pick up pickles? Put it in a text. Time to go to the doctor? They better make house calls.

That’s why I’ve been thinking a lot about productivity devices that can record my day and then hand me a punch list, a summary, and a litt…

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