How This Founder Turned Paranoia Into Her Superpower with Anastasia Leng

How This Founder Turned Paranoia Into Her Superpower with Anastasia Leng

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 steady How a "top 10 startup" with great press still couldn't raise, and what she learned from it The difference between how a first-time and second-time founder talk to investors Why 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 down Why being profitable is the only real leverage a founder has What AI is quietly doing to judgment on her team New episodes of Not Another Podcast every week. Subscribe on YouTube, Spotify, and Apple Podcasts.

Why This Investor Says the Whole VC Model Is in Crisis | Jenny Fielding

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.

How a 6th-Grade Dropout From Togo Built a $100M Fair Trade Brand With No VC

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 money The 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 impossible The community programs that can't be measured in EBITDA, including a woman who named her baby after the brand because it saved her life What two years of depression looked like after leaving a company woven into every wall of his home How he launched Ayeya with no capital, in a market that had changed, and decided to go all out because he had nothing left to lose Why buying Alaffia back felt like life and death, not a transaction His vision: West Africa needs to stop being a raw material producer His 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 [http://alaffia.com], available at Whole Foods stores nationwide.

The $500M Hedge Fund Where Every Single Employee Owns a Piece: Shamir Karkal

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 upside How employees get screwed on options at acquisition, and how Shamir did it differently The $14.6M employee payout from Simple and the board fight behind it Why every Aleph Invariance employee owns a stake in the fund What PNC destroyed when they shut Simple down How to build a de novo AI fund when you've never worked in finance Why 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!

The Founder Who Runs Offsites for 500+ Companies Says Most Remote Teams Get This Wrong | Jared Kleinert

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.