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Chloe Samaha told the crew in the green room that your calendar predicts your future better than your ambition does. Brennan opened the episode with it. She's 22, co-founder and CEO of BOND, and she got into Y Combinator at 21 off a reply to a single tweet. Before that she cold emailed hundreds of private equity partners as a freshman, learned that sales was the one thing she could prove on an application with no resume behind it, and built the first version of BOND out of a founders house in San Francisco. Then there's the part that explains the rest of it. At 19, on her second solo skydive, her first parachute didn't open. She spent that night journaling and came out obsessed with where every hour goes. In this episode: • How a reply to one tweet turned into a YC acceptance at 21 • What YC screens for in a founding team, and why most companies die from the co-founder relationship • The founder debt meeting she runs with her co-founders every week • Why she cuts every goal's timeline in half • What 2,000 CEOs told her about their own companies • Why she's bullish on Gen Z, and the 19-year-old hire who proved it • The jump where the parachute failed, and the 40 minutes of drills that saved her New episodes of Not Another Podcast every week. Watch on YouTube, listen on Spotify and Apple Podcasts. Timestamps: 00:00 Intro 00:34 Your calendar predicts your future, not your ambition 04:34 The reply to one tweet 07:59 Auditing where the hours actually go 09:57 Cutting every timeline in half 14:19 How she got good at sales by 21 19:40 Getting into Y Combinator 22:54 Why she's bullish on Gen Z 23:56 Hiring young, and the 19-year-old who ran distribution 26:52 Getting 2,000 CEOs on the phone 30:43 Breaking down the Product Hunt launch 32:21 Collecting people more exceptional than her 34:09 Why she builds in San Francisco 36:18 What Beirut and Paris gave her as a founder 41:51 Being a millionaire on paper at 22 47:51 Why she's max on AI when her peers aren't 52:16 What 2,000 CEOs don't know about their own companies 59:05 The skydive, and what it made her decide 1:00:12 The billboard

Brennan Pothetes builds companies out of New York, and in this episode he says San Francisco is a B tier place to start one. No guest this time. Just the arguments he has with founder friends over drinks, settled out loud with letter grades. Brennan ranks the six things founders fight about most: where to build, how to fund it, what to read, how to lead, how to work, and what to do with your twenties. Profitable businesses take S tier for funding, while venture, the path he has raised on for years, lands at B. Deep work blocks beat 996. Europe gets an F, and he knows his European investors are watching. Radical candor tops the management list, with fear-based hero mode at the bottom next to LinkedIn slop. For founders tired of consensus takes, the grades are the point. In this episode: • Why New York is S tier for applied AI, and what San Francisco's flood of talent actually costs you • The funding source Brennan puts above venture, debt, and private equity • The one way to fund a company he says you should never use • Why deep work blocks outrank the 996 schedule taking over AI • The book he made required reading at his own company, and the one he rates F tier • The leadership style he built his companies on, and the one that quietly wears teams down • What he tells 22-year-olds to do instead of firing off AI-written resumes Subscribe for more unfiltered founder conversations on Not Another Podcast. Watch on YouTube, listen on Spotify and Apple Podcasts. Follow Brennan and Infinity for what's next. Timestamps: 00:00 Intro 00:41 Welcome to the tier list 00:58 Founder work philosophies 01:45 Why 996 lands at C 02:23 LinkedIn slop, F tier 02:38 The best city to found in 03:45 San Francisco at B 04:05 Anywhere in Europe, F tier 04:25 New York at S 05:03 Fundraising sources 05:54 The one way he says never to fund a company 06:12 Books for founders 07:17 Your professor's textbook, F tier 07:41 Management and leadership styles 09:21 Fear-based hero mode 09:45 Radical candor at S 10:04 What to do in your 20s 10:19 Travel, and the Octopus card in Hong Kong 11:28 The S tier career move 12:21 AI-written resumes, F tier

Adam Delehanty has been a Knicks fan since he was zero years old. What struck him about last season's run was that when OG tips the ball in, there is no debate about what just happened. Then he goes back to his own work, and the work of most of the people watching, and it's Google Docs and strategy decks and products nobody may ever see. Brennan sits down with him as the founder and CEO of Ghost, a content agency that writes books and culture documents for some of the biggest names in tech. His argument to founders is uncomfortable: stop writing about your company. Your job is to build something so extraordinary that other people write about it anyway, and then spend your own words on everything else. They get into the parts nobody says out loud. Why the agency model of a charismatic CEO winning the business and handing the work to a 23-year-old feels icky in every sense. Why he shrank his own company on purpose. The executive coach he turned down after one AI-written proposal. And why he thinks the internet makes tech look further to the right than it actually is. In this episode: • The Knicks scoreboard problem: how a knowledge worker knows whether anything they did mattered • His four steps to original output: unusual inputs, an unusual life, leaning into your weird, and authenticity • Going to primary sources, and the friend posting Eisenhower footage his generation has never seen • Borrowed audience versus bought audience, and the third category he calls squad media • Why attaching your company to something bigger than itself is the whole game • The party test: how long you'd last talking to someone who only riffs about their product • Why he shrank his agency instead of scaling it, and what talent plus AI replaces • Human, Claude, human: where he actually uses AI and where he refuses to • Proof of work for creatives, and wanting to see the sweat coming off the saxophone • Why he thinks centrist and center-left voices in tech stay quiet Subscribe for new episodes every week. Watch on YouTube, listen on Spotify and Apple Podcasts. Find Adam Delehanty on LinkedIn and X.

Sarah Perl had fewer than 150 followers when a tarot video she posted as a college sophomore went viral overnight. Three years later she'd made over a million dollars in courses, paid off the student debt she took on for a teaching degree everyone told her not to get, and left Brooklyn for LA. This year she shipped Stella, an AI app she designed the front end of herself using Claude Code, on no venture funding. Brennan sits down with her not as the internet's manifestation girl, but as what she actually is: a distribution-first, bootstrapped, AI-native operator with 4.5 million followers and a very specific theory of why founders win. Her framing for this audience is blunt. Manifesting is the For You page. Where you put your attention is where your life ends up going, and belief is the highest-leverage, lowest-effort thing you can work on. They get into the parts she almost never gets asked about: why she'd only hire neurodivergent people, what her ADHD has actually cost her, the Twitter thread full of guys planning to build her app that pushed her to ship, and the launch week when her own users turned on her pricing. In this episode: Why she optimizes for obsession instead of strategy, and how that shapes what gets builtThe exact origin of "I get paid to exist," said years before it was remotely trueHow she reframes ADHD and anxiety as an operating system rather than a defectWhat building the front end of a real app with Claude Code on her phone actually looked likeThe Twitter thread that made her stop planning and shipWhy lottery winners lose the money, and what that has to do with your revenue ceilingThe biggest regret of her life, and why she still wouldn't change it Subscribe for new episodes every week.Watch on YouTube, listen on Spotify and Apple Podcasts.Find Sarah at @hothighpriestess and download Stella on the App Store.

Afsheen Afshar has one of the strangest résumés in tech: an MD and a PhD who built brain-machine interfaces that helped paralyzed patients type using only their thoughts, then walked away from medicine to become Wall Street's first Chief Data Science Officer at J.P. Morgan. So when he says most of the AI being sold today is "theater," he has the standing to mean it. In this conversation with Brennan Pothetes, Afsheen (Founder Managing Partner of Pilot Wave Holdings) draws a hard line between what's real about AI and what's a very expensive branding exercise. He explains why LLMs are just "the most multidimensional autocomplete ever devised," why AI projects fail on culture and never on the math, and why he's quietly buying boring Main Street companies while everyone else chases the next San Francisco demo. It gets spicy: the pair debate whether trading your data for "free" services is capitalism working or a rigged barter, why the foundational-model labs are losing the public, and what a brain scientist thinks machines still can't copy. Highlights: How to tell real AI from "theater" in under a minuteThe prompt trick a doctor uses to get expert-level answers from any modelWhy "data is the new oil" is a warning about who owns your futureWhat Wall Street's first AI chief saw inside the big banksThe VC line about small business that sent a chill down his spineWhy he says AI is "plenty dangerous" without ever being consciousThe one thing the human brain does that no model comes close to Subscribe to Not Another Podcast for unfiltered conversations with the founders and operators actually building the future. Watch on YouTube. Listen on Spotify and Apple Podcasts.

Brennan Pothetes built eight companies in a single year and just closed a $24M raise for Infinity Constellation. So when listeners flooded him with questions, he did what most founders won't: he answered them straight, including the ones that expose his own contradictions. In this solo AMA, Brennan breaks down the exact first move Infinity makes before anyone writes a line of code, why he no longer believes in tech moats, and what selling his last company (Butter) taught him about ignoring external validation. Then it gets honest. Asked which part of the "toxic" Silicon Valley playbook he still runs, he admits he grinds harder than anyone he knows, emails at all hours, and chases being the fastest to reply, before conceding, one layer deeper, that the whole ethos is a pipe dream. For founders drowning in hustle-culture advice from people who never cop to the cost, Brennan's candor is the point. In this episode: The one-page memo Infinity writes before building anything, and why it beats a business planWhat selling Butter taught Brennan that a win never couldWhy he stopped believing tech moats are durable, and what he trusts insteadWhether his AI bill is really cheaper than headcount (and the exact math)His advice to 22-year-olds deciding between a job and going all-inHow to run a side company without handing your employer the IPThe hustle habit he genuinely can't quit, and the moment he admits it's a pipe dreamSubscribe for more unfiltered founder conversations on Not Another Podcast.Watch on YouTube, listen on Spotify and Apple Podcasts.Follow Brennan and Infinity for what's next.

Silicon Valley says move fast and break things. Shensi Ding built Merge by doing the opposite: nine months of building with zero users, obsessing over margins while everyone else chased growth at any cost. Today the fastest-moving AI companies in the world, including Mistral and Perplexity, run on the infrastructure she refused to rush. Brennan sits down with the co-founder and CEO of Merge ($75M from Accel, NEA, and Addition) to talk about the unfashionable choices behind the connective layer of production AI. Shensi gets candid about the post-Series B hiring spree that felt like "an organ getting rejected," why she studies competitors like Sherlock Holmes, the stigma around Chinese open-source models, and the fertility numbers that made her rethink founder stress. Highlights: Why building for nine months with zero users meant launching with zero bugsThe over-hiring mistake, and the "fewer, better people" rule that came out of itHow one rogue AI agent can delete your entire Salesforce, and how to stop itChinese open-source models, and how American routers put a "surface" on top of themWhy model access based on citizenship is coming to your company"You can't fake margins forever": her case against AI financial engineering20 eggs, one embryo: the honest math of founder stress and fertility Subscribe to Not Another Podcast for more unfiltered conversations with founders building through the hype.Watch on YouTube, listen on Spotify and Apple Podcasts.Find Shensi on LinkedIn and X (@shensi) · merge.dev

For 25 years, you have been renting. Your photos, your files, your audience, your work… all of it lives on someone else's servers, in formats you can't touch, monetized by a handful of companies that can evict you anytime. Ben Guo thinks that's the great unspoken scam of the modern internet, and he left a nearly nine-year career at Stripe to do something about it. Ben was an early employee at Venmo and the founding engineer on Stripe Terminal. Now he's the co-founder of Zo Computer, a personal cloud computer he describes as "your home on the internet" and pitches, only half-joking, as "AWS for my mom." In this conversation with Brennan Pothetes, he makes the case that the next giant consumer wave isn't AI taking your job, it's AI finally letting ordinary people own a piece of the internet. It gets spicy. Ben argues SaaS needs to die, explains why he spent $9,000 on AI coding in a single month, breaks down "velocity coding" versus vibe coding, and tells the story behind the name Zo and his Pegasus logo. If you're tired of the same recycled AI-future takes, this one cuts in a different direction. In this episode: Why Ben says we've "never owned real property on the internet" and what that actually costs youThe "AWS for my mom" test, and how building for a biologist with no coding background shaped the productWhy he believes SaaS has to die and individuals become their own software providers"Velocity coding, not vibe coding": how he writes 500K lines in two months and barely reads codeThe $9,000 Cursor bill, and how he decides whether AI spend is actually workingWhy he built personal agents before OpenAI made them cool, and how OpenClaw became a tailwindWhere the name Zo comes from and why his logo is a Pegasus Subscribe for new episodes of Not Another Podcast with Brennan Pothetes.Watch on YouTube, listen on Spotify and Apple Podcasts.

George Kurdin spent years as a professional poker player before online poker was shut down overnight. The skill he carried into building a company wasn't the one you'd expect. It had nothing to do with reading faces across a table and everything to do with expected value, risk, and the discipline to iterate before you get crushed. Now George is co-founder and CEO of Monk, an AI-native accounts receivable platform automating the whole contract-to-cash lifecycle. He sat down with Brennan Pothetes to make the case for building in the least glamorous corner of AI, why "touching money" earns you the right to build something big, and why he's genuinely worried about the foundation model labs even as he builds in their blast radius. This one gets into the real mechanics of building an AI company in 2026: hiring 1 in 700, running on one meeting a week, what an "agent harness" actually is, and where defensibility still lives once the models are a commodity. Inside the episode: Why George says poker teaches risk and EV, not reading people, and how that maps to foundingThe principles he used to pick his market, including "don't get nuked by Satya and Sam"Why he believes you "earn the right to build a big business if you touch money"His spicy take on the labs, valuations, and the shift toward Chinese and open modelsWhat an "agent harness" is, explained through L4 self-driving cars and human-in-the-loopHow he hires (1 in 700) and runs the team with one weekly all-hands and no standupsWhere moats still exist in the AI app layer when the tech is no longer the advantage Subscribe for more conversations with the founders building what's next.Watch on YouTube, listen on Spotify and Apple.Follow George and Monk for more on AI-native finance.

Americans spent roughly a trillion dollars on property and casualty insurance last year. Only about 60% of it came back as claims, and that number has been falling for decades. Rashmi Melgiri wants to know where the other $400 billion went, and why nobody seems to be measuring whether the industry is getting any better. Rashmi started as an antitrust economist at 21, modeling DOJ and FTC cases, before spending years in telecom and co-founding CoverWallet, which she raised $35M for and sold to Aon. Now she's the founder and CEO of Functional Finance, building the financial rails underneath insurance. Along the way she's developed a framework she calls "infrastructure of life," the idea that insurance, telecom, energy, and healthcare are a different class of industry, and that the only people left with the energy to reform them are founders, funded by a system that routes them right back to the incumbents they set out to beat. She and Brennan get into it: free markets versus regulation, why she went back to build a second company in the same industry she'd already exited, and what it actually felt like to sell to Aon. In this episode: Why only 60 cents of every insurance dollar reaches a claim, and where the rest goesThe "infrastructure of life" thesis: which industries we've stopped protecting, and whyHow selling to Aon showed her the reform path that ends inside the incumbentWhy she thinks founders, not government, are the last reform mechanism leftThe bankruptcy double standard between corporations and peopleWhat an antitrust economist sees in insurance that founders missWhy she started a second company partly to test if she could be the CEONew episodes of Not Another Podcast every week. Subscribe on YouTube and follow on Spotify and Apple Podcasts so you don't miss one.

Anastasia Leng's first company got everything a founder is supposed to want. Time named it a top 10 startup to watch. The press loved it. She still couldn't raise a dollar, and it died a slow, public death. What she built next, CreativeX, now works with Unilever, Heineken, and Google. This conversation with Brennan Pothetes is about the psychology that made the second time different: paranoia she repurposed as preparation, a hard refusal to chase validation, and the lesson that taught her to speak an investor's language without burning down the only company she has. She moved through five countries before she was 13 and learned English at 12. She talks about the fear that nearly kept her at Google, the investors who told her to quit, why she refused to wipe out her early angels, and the emotional game of building that almost no founder discusses honestly. In this episode: Why she trained herself to imagine the worst, and how it makes everything else feel steadyHow a "top 10 startup" with great press still couldn't raise, and what she learned from itThe difference between how a first-time and second-time founder talk to investorsWhy she refused the "clean cap table" every VC demanded, and how it paid off What she did when respected investors told her to shut the company downWhy being profitable is the only real leverage a founder hasWhat AI is quietly doing to judgment on her teamNew episodes of Not Another Podcast every week. Subscribe on YouTube, Spotify, and Apple Podcasts.

Jenny Fielding has returned three funds' worth of capital and backed two 2015 unicorns she's still holding 11 years later. So when she posted that early-stage VC's entire model might not survive the disruption cycles it's funding, founders listened… and almost no VCs commented. In this conversation with Brennan Pothetes, Everywhere Ventures' Managing Partner says the quiet part out loud: AI is collapsing tech innovation cycles faster than a 10-to-15-year fund can underwrite, the "tech moat" is mostly dead, and a founder just handed her back a Series A because he could see his own ceiling. They get into what's actually defensible now, why she runs 60-70 bets instead of 20, and why DPI is the only number that matters. It's a fast, spicy, no-spin look at where venture and company-building are headed from someone willing to bet her own portfolio on the answer. • Why the 10-year fund model is in an "existential crisis" no one will name• The real story behind the founder who returned a Series A check• The four things still defensible after AI: brand, data, integrations, distribution• Why she takes 60-70 bets when most early funds take 20-30• How small funds quietly out-earn the billion-dollar mega-funds on DPI• The "why then" slide every founder is missing in their pitch• Why she sat out Web3 and frothy AI rounds New episodes of Not Another Podcast drop every week. Subscribe so you don't miss the conversations other founders and VCs are too careful to have.

Olowo-n'djo Tchala grew up sharing an 8x10 room with his mother and seven siblings in Togo (a family of 41 brothers and sisters, one of the world's poorest countries) and left school after the sixth grade. In 1996, a Peace Corps volunteer named Prairie Rose came to his village. They fell in love and moved to California. Later on with 17 women in West Africa, a shea nut tree, and student loans, he built Alaffia: a fair-trade beauty company that would reach $100M in sales, 250,000 lives touched in West Africa, and shelf space in Whole Foods nationwide. No outside investors. For twenty years. Then the investors arrived. Four months later, Olo resigned. He couldn't look the West African women in the eyes and tell them their wages were being cut. He watched Alaffia deteriorate from the outside. He built Ayeya from scratch… no capital, a changed market, everything to prove again. Then, in late 2025, he bought Alaffia back. What Brennan and Olo get into in this episode goes beyond any founder story NAP has told: Why Olo went 20 years without outside investors and what happened within 4 months of taking the moneyThe specific moment "optimization" crossed from business decision to personal betrayal "I see all these women as my mother" and why that made the investor conversation impossibleThe community programs that can't be measured in EBITDA, including a woman who named her baby after the brand because it saved her lifeWhat two years of depression looked like after leaving a company woven into every wall of his homeHow he launched Ayeya with no capital, in a market that had changed, and decided to go all out because he had nothing left to loseWhy buying Alaffia back felt like life and death, not a transactionHis vision: West Africa needs to stop being a raw material producerHis answer to the question he's always wanted to be asked: "What does healing look like in business?"His billboard: "Don't compromise the fire that you have in you."Subscribe to Not Another Podcast on YouTube, Spotify, and Apple Podcasts. Follow Infinity @infinityvc. Find Alaffia at alaffia.com, available at Whole Foods stores nationwide.

Shamir Karkal co-founded Simple in 2009, one of the first real digital-first banks in the US. When he sold it to BBVA for $117M in 2014, he and his co-founder fought their board to distribute $14.6M of the proceeds to roughly 100 employees, excluding the founders. He's applied that same principle at every company since, including his current AI fund, where every employee owns a stake in the fund itself. In the hedge fund world, that's almost unheard of. Today he's Co-founder and President of Aleph Invariance, an AI fund based in Portland with an intentionally low public footprint. He's also Co-founder and Chief Strategy Officer of Sila, the programmable money API platform that has raised $20M+. Before Sila, he built BBVA's Open Platform after the Simple acquisition, creating the API infrastructure that helped power a generation of embedded-finance startups in the US. In this episode: Why first movers do the hard work and second movers capture the upsideHow employees get screwed on options at acquisition, and how Shamir did it differentlyThe $14.6M employee payout from Simple and the board fight behind itWhy every Aleph Invariance employee owns a stake in the fundWhat PNC destroyed when they shut Simple downHow to build a de novo AI fund when you've never worked in financeWhy humanities majors are about to become more valuable than engineers If you know a founder who's ever wondered whether it's possible to build something great without leaving your team behind, send them this one. Subscribe for more episodes of Not Another Podcast every week!

Jared Kleinert is the Founder and CEO of Offsite, the company that handles end-to-end retreat and offsite planning for hundreds of companies, including Perplexity, HubSpot, Walmart, and Remote. Before building Offsite, he became one of the most connected people in the startup world, was named USA Today's "Millennial Influencer of the Year," and wrote books about building relationships and building companies. In this episode, Brennan and Jared get into why the bar to stand out as a job applicant is shockingly low (and what to actually do about it), Dan Martell's 10-80-10 rule for using AI without losing your voice, what actually builds remote work culture and what doesn't, why fundraising might be creating more risk than you think, and why the founders who do the service manually before they build the tech are almost always the ones who win. If you're hiring, building, or just trying to figure out how to use AI without becoming a copy-paste machine, this one's for you. Subscribe to Not Another Podcast wherever you get your shows.