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/)
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 |





From photojournalist to AI director: Inside a modern videographer's workflow
Ever wonder how real videographers are using AI video? Check out this workflow with my friend Ali Powell.
From photojournalist to AI director: Inside a modern videographer's workflow
If you’ve ever wondered how AI-generated content goes from concept to screen, buckle up—here’s a wild example of an idea moving from script to finished video in just a couple of days
Two weeks ago, Ali Powell, an AI video producer based in Tokyo, was tasked with creating a two-minute video for a company called iWallet. The brief was straightforward: produce a short, engaging video that highlighted iWallet’s latest product—a service that allows users to pay for home repairs quickly and effortlessly.
The video itself was fairly simple in structure, but the challenge was to make it lively, visually appealing, and informative all within a 90 second clip. The process started with the script, which laid out the key points about the product. It wasn’t Citizen Kane, but it could lend itself to something interesting.
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Here’s a snippet of that script:
Powell started out the old way, shooting and cutting video for newsrooms like CoinDesk and TechCrunch. He knew how to build a story from raw footage, how to pace it, how to make it watchable and even viral. That part did not change. What changed was the ground under him. As AI tools crept into production, the market for that kind of hands-on work began to thin out. Some jobs vanished, others shrank, and the path forward stopped looking stable. He didn’t have to carry a camera and gear anymore and he felt lost for a while, wondering what his skills and background were good for.
So he shifted. The skills he already had like story sense, timing, and visual instinct, turned out to map well onto prompting. Instead of directing a crew, he began directing AI. Instead of waiting on budgets and schedules, he could move fast, testing ideas in hours that once would have taken weeks.
That is when things started to get strange, in a good way. Powell had always been deep into comics. With AI, he could finally build them. He began sketching out scenes that would never get greenlit in a studio system. Robin Williams as the Riddler, not as a joke but as a fully realized take on the character. William Katt, remembered by many as the lead in The Greatest American Hero, he recast as the Flash.
Powell was no longer limited by access or budget. He was limited only by taste and patience, which is how storytelling used to work before the machinery of production grew so large. This video hit 1 million watch hours just because it was so wild: a 1970s romp that mimics the visual style of old superhero shows almost perfectly.
With those skills in tow, Powell got to work.
“First, I generate stills with Nano Banana which set the scene and create the characters. For example, if I’m doing something with home repair I’ll generate a home owner and a contractor and maybe some kids. Just characters I’ll use over and over.”
Here’s the HVAC guy he made:
He’s careful to prompt properly.
“If you just give it junk, you get junk out,” he said. “You have to prompt very carefully.”
He sent this as evidence. Check out the dialogue:
The process continues with more and more detailed prompts. For example, he asked the AI to produce scenes with the HVAC repair person and the homeowner. The interactions are still a bit stilted but they get the point across. For this prompt he basically asked for his generated HVAC guy to meet the homeowner at their home.
And then wrote “The HVAC repair guy fixes the leak and replaces the unit, the female home owner happily pays him.”
Not all of the footage works on its own. There is always a trace of something off. Faces hold a fraction too long. Movements feel slightly delayed. A lot of it sits in that uneasy space where the image is close enough to feel real, but not close enough to forget how it was made.
That is where Powell’s background starts to matter. He writes dialogue to give the scenes shape. He cuts aggressively, trimming anything that drags or breaks the rhythm. What begins as something loose or even comedic starts to take on structure.
He works the way a traditional shooter would. He gathers more than he needs, then builds from it. He prompts for extra angles, small inserts, connective shots, the kind of B-roll that carries a story forward Then he weaves those pieces in between narration, letting the sequence breathe in a way that feels intentional rather than accidental. The result is not perfect, but it is coherent, and that still counts for a lot.
He could not share the final cut yet, but we will post it once it is ready. What he built, in practical terms, is a complete two minute commercial delivered in both portrait and landscape formats, finished in under two days. Not long ago, that kind of turnaround would have required a crew, a schedule, a location, and weeks of post production.
Now the work moves at a different pace. Powell can sketch, test, discard, and rebuild without waiting on anyone else. He can generate scenes, revise them, and slot them into place almost in real time. The process is faster, but it is also more fluid, closer to editing in the mind than coordinating a set.
He is not blind to what has been lost. There is a texture to traditional video, a physicality, a sense of presence that comes from real light, real movement, real people in a room. That does not fully carry over. He misses that. At the same time, he recognizes what he has gained. The range of ideas he can try has expanded. The cost of failure has dropped and he can follow an impulse all the way through to a finished piece, and that kind of creative freedom is hard to ignore.
“These tools give me superpowers,” he said.
Generated is a newsletter about the craft behind AI-powered video. Edited by John Biggs, it looks at what happens when video production and AI tools start to merge. The focus is on the people, tools, and techniques we are using in the fascinating medium.
© 2026 John Biggs
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