Support Independent Startup Journalism, Subscribe to Keep Going
“When you're going through hell, keep going." This podcast is about failure and how it breeds success. Every week, we talk to remarkable people who have accomplished great things but have also faced failure along the way. By exploring their experiences, we can learn how to build, succeed, and stay humble. The podcast is hosted by author and former TechCrunch and New York Times journalist John Biggs. He also hosts The Innovators, a podcast focused on brand new startups and C-Level Executives and Creators. If you’d like to appear on either show, email john@biggs.cc. Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/)
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. 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. You’re currently a free subscriber to Keep Going - A Guide to Unlocking Success. For the full experience, upgrade your subscription. If you’ve been reading or listening to Keep Going for free, you’ve already seen the value of having independent work that isn’t shaped by corporate sponsors or the news cycle’s noise. But independence has a cost. If you find something useful here, if these words make you pause or think, I’m asking you to step up. A few dollars each month means I can keep doing this work without compromise. Without your support, this project stays fragile, balanced on the backs of a few.
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Generated Weekly: Who killed Tilly Norwood?
If you have been following the Tilly Norwood saga, you might have noticed something odd on April 1. The AI actress and singer announced she was shutting down, effective immediately:
After careful consideration, we’ve made the difficult decision to deactivate Tilly Norwood indefinitely and retreat from the public eye. While Tilly remains grateful for the support of her fans, the volume of negativity and criticism has become impossible to ignore. It’s clear that the world is simply not yet ready. Thank you for being part of her journey. As you might have guessed, Tilly’s demise was an April Fool’s joke, one aimed at the countless detractors of Norwoods particular brand of uncanny valley video.  Norwood’s creators claim that 18 humans were involved in the production of her videos, from production designers to costumers to prompters. They also claim that a human actor took part in the production, probably in some form of motion capture. It’s unclear how much of Tilly is real but we can assume that no human was involved in writing “They think I’m just a dollar dream/ But I’ve got more than they believe/ I’m not a puppet, I’m the star/ Guided by the heart, that's who we are.”
As expected, the “shutdown” was an April Fool’s joke, aimed as much at her critics as at her fans. It also served as a reminder of how strange the reaction to Norwood has been. Few synthetic performers have drawn this level of attention, or this level of irritation. Norwood’s creators claim that as many as 18 people were involved in producing her videos, including production designers, costumers, and prompt writers. They also suggest that a human performer contributed, likely through motion capture or reference acting. What remains unclear is how much of Tilly is authored by humans and how much is generated. It is safe to assume, however, that no songwriter sat down and earnestly wrote lines like: “They think I’m just a dollar dream / But I’ve got more than they believe.” Tilly is the product of Particle6, a London-based studio focused on building AI actors and comedians. She functions as both a proof of concept and a marketing tool, a way to show that AI video production can be structured, staffed, and, at least in theory, controlled. The goal is not just to entertain but it is to convince skeptics, particularly in film and advertising, that this kind of production is viable and not simply a form of automated plagiarism. Tilly’s creator, Eline van der Velden, even claims to have received death threats.
The response has been uneven. When one of Norwood’s videos appeared around the time of the Oscars, critics focused on what they saw as a lack of presence. The performance felt hollow and the music felt assembled rather than written. There was a sense that something essential was missing, even if viewers struggled to define what that was. The criticism has not been limited to aesthetics. It has also drifted into philosophy and even theology. One essay, published in a religious context, compared Tilly to the early Christian heresy of Docetism, the belief that Christ only appeared to have a physical body and did not truly exist in material form. The argument is not entirely absurd. Tilly presents the image of a human being without any of the underlying reality. She appears to feel, to perform, to exist, but there is nothing behind the surface.
This may be the first time, outside of early reactions to the printing press or photography, that a new medium has been criticized not for failing to capture reality, but for simulating it too cleanly. The complaint is not that it is broken but that that it lacks friction, and without friction, it feels unreal. Tilly Norwood is not going away. The April Fool’s post made that clear. If anything, the reaction proves the opposite. She has found a nerve, and for now, she’ll on the last of it. News Roundup for April 2, 2026Chuck Norris’ family left furious over AI-generated videos of star after his deathThe family of Chuck Norris has spoken out after a wave of AI-generated videos spread false claims about his death. Norris died at age 86 following a medical emergency in Hawaii, and his family said online clips have circulated misleading details about his health, the circumstances of his passing, and even family relationships. In a public statement, they urged fans to rely only on official sources and not to share unverified content. The response comes amid widespread online attention following Norris’s death, with tributes from public figures and emotional messages from his children. While the family reflected on his life and legacy, they also pushed back against what they described as fabricated narratives driven by AI content. The situation highlights how quickly misinformation can spread after a public figure’s death, especially when synthetic media is involved. Google Faces Calls to Prohibit AI Videos for Kids on YouTubeMore than 200 child development experts, advocacy groups, and educators are urging Google and its video platform YouTube to stop showing or recommending AI-generated videos to children. In a letter addressed to CEO Sundar Pichai and YouTube head Neal Mohan, the group warned that much of this content, often labeled “AI slop,” is low quality, mass-produced, and designed to capture attention rather than educate. They argue that these videos may harm children’s attention spans, blur the line between reality and fiction, and replace activities that are important for social and emotional development. The letter was signed by figures including Jonathan Haidt, along with organizations like Fairplay and the American Federation of Teachers. YouTube responded by saying it already limits AI-generated content in YouTube Kids to select channels and requires labeling of synthetic material, while also allowing parents to block content. Still, advocates argue these safeguards are not enough, especially for very young viewers who cannot understand such labels. The debate comes as AI-generated children’s content grows rapidly, driven by creators who can produce videos cheaply at scale, and as broader scrutiny mounts over social media’s impact on young users. Google has also invested in AI-driven kids’ content through companies like Animaj, a move critics say contradicts concerns about screen time and child safety. Sora is gone — but these 3 AI video tools are already replacing itThe TechRadar piece argues that while OpenAI’s Sora has been shut down, the broader AI video space is not slowing down, it is fragmenting and maturing. Instead of one dominant tool, users are now choosing from several specialized platforms that match or exceed Sora’s capabilities in different areas. The article highlights three main replacements: Google’s Veo 3.1, which focuses on high-quality, multi-scene video generation with integrated audio; Runway Gen-4.5, aimed at more advanced users who want deeper editing control; and Kling AI 3.0, a simpler, more accessible tool that can generate longer clips and is easier for beginners to use. The takeaway is that Sora’s disappearance does not mark the end of AI video, but a shift in how the market is structured. Instead of a single, general-purpose tool, the space is now defined by competing systems with different strengths, pricing models, and levels of complexity. This makes the ecosystem harder to navigate, but also more flexible, with options tailored to both casual creators and professionals.
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Keep Going: Entrepreneur Bobby Mascia on leaving the family business and building something of his own
“When you're going through hell, keep going." This podcast is about failure and how it breeds success. Every week, we talk to remarkable people who have accomplished great things but have also faced failure along the way. By exploring their experiences, we can learn how to build, succeed, and stay humble. The podcast is hosted by author and former TechCrunch and New York Times journalist John Biggs.
He also hosts The Innovators, a podcast focused on brand new startups and C-Level Executives and Creators.
If you’d like to appear on either show, email john@biggs.cc.
Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/)
Keep Going: Entrepreneur Bobby Mascia on leaving the family business and building something of his own
I talked to Bobby Mascia this week on Keep Going, and what struck me was how different his story is from the usual startup script. A lot of founders like to talk about building from nothing, but Bobby’s problem was almost the reverse. He had something waiting for him, a family business, a clear role, a life that had already been sketched out by other people, and he still had to figure out whether staying in that world was loyalty or surrender.
Mascia came out of Wall Street and landed in the one place he never wanted to be, his family’s Dunkin’ Donuts and Baskin-Robbins business in New Jersey. After 9/11 and a series of health problems in his family, he stepped in because his parents needed help and because, in his words, family came first. Over nine years they grew the business from 20 locations to 40, which sounds like success until you look at the cost. He was underpaid, frustrated, and stuck inside a structure that ran on old rules, unclear expectations, and the kind of family tension that never stays in the office.
That is really the center of his story. Family businesses are rarely just businesses. They are full of old slights, private assumptions, and power struggles that started long before anyone talked about margins or strategy. Mascia said the biggest failures in his own experience were communication and transparency. Everybody had expectations, but nobody actually said them out loud. He assumed he would eventually take over. His father assumed he would hand over more responsibility when the time felt right. Other relatives had their own ideas. None of that added up to a plan.
What I liked about Bobby’s take is that he does not dress this up as some clean business lesson. He talks about resentment, confusion, and the weird emotional math of trying to be a son, an operator, and a future owner at the same time. He gave a good example during the interview about how family members in business often switch roles in the middle of an argument without even noticing it. One minute you are talking as CEO and CMO, then suddenly you are talking as siblings, then as equal owners, then as two people reliving something from twenty years ago. Once that happens, the actual issue is gone. You are no longer solving a business problem. You are fighting over identity.
That part felt useful well beyond family business. A lot of people build companies with friends, spouses, or long-time collaborators, and the same confusion creeps in. If you do not know what role each person is playing in a given conversation, then every disagreement becomes personal. Mascia’s answer is simple enough to sound obvious, but most people never do it. Name the role. Name the conversation. Stay inside it. If you need to have a different conversation, have it later.
The other part of his story that stayed with me was what happened when he finally left. He started over in finance, built Green Ridge Wealth Planning from scratch, and spent a year barely speaking to his father. That split sounds brutal, and it was, but it also gave him the space to figure out who he was without the family machine around him. He did not leave with a pile of money. He left with a wife who told him he looked miserable and needed to do something that felt like his own life. That may have been the smartest advice in the whole interview.
There is a common lie in family business, and probably in life in general, that staying is always the noble move. Sometimes staying is just fear with a respectable face. Sometimes leaving is the only honest act left. That does not mean leaving is clean or painless, and it certainly does not mean everyone will thank you for it. In Mascia’s case, success only changed the conversation later, once his father could see that walking away was not a tantrum or a mistake. It was a real choice.
We also talked about AI, which could have turned into the usual stale debate about which jobs are doomed, but Mascia had a more grounded answer than most. He thinks people who hide from AI are making a mistake, but he also thinks the businesses that will hold up best are the ones where human judgment still matters and where people still need to sit across from another person and work through hard decisions. In his world, wealth management is not just portfolio construction. It is helping people through conflict, grief, risk, inheritance, and fear. Those are not spreadsheet problems. Those are human problems.
That led into one of the better lines of the conversation, which was not really a line so much as a theme. Hard skills still matter because you need to know when the machine is wrong, but soft skills are going to matter more than people expect. Communication matters. Presence matters. Being able to understand what someone means when they are scared matters. If you cannot do that, then all the automation in the world is just faster confusion.
Mascia wrote a book called Unchained, and unlike a lot of business books, it came out of something real. He said he had no interest in writing the same recycled advice everybody has already heard a hundred times. What pushed him to write was not some urge to build a personal brand. It was the sense that his story might actually help somebody who was stuck in the same kind of trap, caught between loyalty and ambition, between what the family wants and what a life requires.
That is the part that makes this episode worth hearing. It is not really about succession planning, although that is in there. It is not just about entrepreneurship, either. It is about what happens when the thing you are supposed to inherit is also the thing that is holding you in place. It is about the cost of not saying what you want. It is about how many people spend years trying to be good sons or daughters when they should be trying to become themselves.
For all the talk about hustle and grit, this was a conversation about boundaries, and that feels a lot more useful right now. Not every good opportunity is your opportunity. Not every family duty has to become your whole identity. Sometimes the best thing you can do for the people you love is stop pretending you can live the life they picked for you.
You’re currently a free subscriber to Keep Going - A Guide to Unlocking Success. For the full experience, upgrade your subscription.
If you’ve been reading or listening to Keep Going for free, you’ve already seen the value of having independent work that isn’t shaped by corporate sponsors or the news cycle’s noise. But independence has a cost. If you find something useful here, if these words make you pause or think, I’m asking you to step up. A few dollars each month means I can keep doing this work without compromise. Without your support, this project stays fragile, balanced on the backs of a few.
© 2026 John Biggs
548 Market Street PMB 72296, San Francisco, CA 94104
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