#9 — When Your Startup Dies, Who Are You?

#9 — When Your Startup Dies, Who Are You?

Somya Gupta didn't come to New York to build a startup ecosystem. He came to go to class, pass his exams, and live a comfortable life. Two and a half years later, he's thrown 75+ founder events, shut down his own company in the most painful way possible, and somehow walked away calling it the best thing that ever happened to him. In this episode, Somya and I unpack the full arc — from co-founding an AI-powered edtech platform at NYU, growing it to 3,500 users, pivoting to B2B, landing university pilots, striking what looked like a game-changing partnership… and watching it all collapse in a single phone call. We also get into what it actually feels like when your company becomes your identity — and then disappears overnight. But this episode isn't really about failure. It's about what you do with the version of yourself that comes out the other side. In this episode: * Why Somya says "delusion" is a competitive advantage * The Washington Square Park customer interview mistake (don't do it) * Why VCs hate EdTech — and why he gets it * The Georgian restaurant conversation that ended Context * What's next: IRL experiences, hackathons, and making NYC #1 Timestamps * 00:00 — Intro & small talk (pickleball, NYC spots) * 07:09 — Welcome + who is Somya Gupta? * 08:52 — From India to NYU: the mindset shift * 14:16 — How Context was born * 17:53 — The problem they were solving (and why it was personal) * 21:53 — B2C to B2B pivot: the hard conversation * 25:53 — 3,500 users, zero revenue — now what? * 31:24 — The moment it felt like it might fall apart * 38:29 — Fundraising, EdTech's VC problem, and $15K from NYU * 42:08 — University pilots and the California partnership * 45:24 — The phone call that ended everything * 48:17 — Identity crisis on the Brooklyn Promenade * 50:14 — What came next * 54:47 — Building NYC's founder ecosystem Find Somya:LinkedIn: https://www.linkedin.com/in/somya-gupta-sg/ Instagram: Coming soon 👀

#8 He Survived the UFC. Starting a Business Almost Broke Him

Most people wait until they have time to start a business. Mike and Jimmy never had time. Full-time police officers, fathers, husbands — and somehow, owners of a thriving martial arts franchise in Short Hills, NJ. In this episode of The Friday Sponge, Jack sits down with Chief of Police Mike and UFC fighter-turned-instructor Jimmy to talk about what building a business actually looks like when you're already stretched thin. They cover the real cost of passion projects, what a shareholders agreement protects you from (hint: it's not just strangers), why giving away a membership can be worth more than selling one, and the brutal truth about going into business with your friends. No MBA. No safety net. Just two guys who found something they loved — and refused to let time be the excuse. [00:00] — Why college kids need to think like entrepreneurs[01:11] — "We don't have extra time" — how passion creates time[03:38] — From getting picked on at school to owning a franchise at 22[06:21] — Getting punched in the face (literally and in business)[07:22] — The real rules of running a franchise[09:40] — Why giving away memberships builds a better business[13:03] — How to retain great employees without just throwing money at them[14:43] — Structuring a business so partners can exit cleanly[20:29] — The Liquid Death lesson every entrepreneur needs to hear[22:25] — Should you even go to college?[24:01] — Going into business with friends — the honest truth Company Information: Tiger Schulman Martial Arts Short Hills Instagram @tsma_of_shorthills [https://www.instagram.com/tsma_of_shorthills/#] Website: https://tsk.com/ Jimmie Rivera Instagram @jimmierivera [https://www.instagram.com/jimmierivera/#]

#7 She Left Everything to Fix the One Thing Nobody Talks About in Healthcare

She moved from Belarus, got a computer science degree in her second language, and watched doctors get crushed by insurance chaos from the inside. So she built an AI company to fix it. Stefaniya Barabanava is the co-founder of Sphere — a startup rebuilding how healthcare providers handle insurance communication. "Many of the times they really don't know whether they're getting paid for the work they do." 00:00 Introduction to Financial Literacy and AI in Healthcare02:45 Stefaniya's Journey from Belarus to Healthcare Innovation05:45 The Challenges of the US Healthcare System09:02 Founding Sphere: Addressing Pain Points in Healthcare12:02 Navigating the Startup Landscape: Lessons Learned15:01 The Weight of Responsibility in Healthcare18:06 The Importance of Mentorship and Collaboration21:12 Finding Purpose Beyond Profit24:00 Future Aspirations for Sphere26:51 Fundraising Insights and Storytelling for Startups Follow The Friday Sponge for more stories like this.thefridaysponge.com Connect with StefaniyaLinkedIn: https://www.linkedin.com/in/stefaniyab/Sphere: https://sphereint.net/

#6 - Whipdd - Akshay Kalekar (Co-Founder)

What started as a dinner party conversation is now one of Canada’s fastest-growing butter brands. Akshay, co-founder of Whipdd Butter out of Toronto, joins us this week to share how a single evening with his co-founder and their spouses sparked a business that would go from zero to over 100 retail locations in under two years — including a landmark deal with Whole Foods Toronto and nearly $500K in annual revenue. Born and raised in India, Akshay didn’t come from the food industry — he came from the school of knocking on doors and hearing “no.” And it turns out, that’s exactly the skill set you need when you’re trying to break into one of the most competitive shelves in grocery retail. In this episode, we get into the gritty origin story behind Whipdd — the hustle, the rejections, the wins, and why Costco and Walmart should probably start paying attention. This week we talk about: • Navigating rejection and turning “no” into momentum • Breaking into major retailers from scratch • Pursuing a bold vision in an oversaturated market  Tune in and soak it all up — it’s Friday, and this one’s worth your time. Company: https://www.whipdd.com/ Instagram: @whipdd.to LinkedIn: https://www.linkedin.com/in/akshaykalekar

#5 Miles Square Theater - 23 Years of Defying the Odds

Most arts organizations with their funding model would have closed by year five. Mile Square Theater just hit year 23. This week, we sit down with Elizabeth DiCandillo and Chris Cragin-Day — two leaders who could have taken the corporate path and didn’t. Instead, they built something Hoboken didn’t know it needed: an award-winning theater running on operational brilliance, deep community roots, and a stubborn refusal to quit. But this conversation goes beyond the stage. Elizabeth makes a case that the loneliness epidemic and the collapse of real relationships didn’t start with social media — it accelerated the moment we convinced ourselves a Zoom call was a substitute for showing up. She argues that the antidote isn’t an app. It’s a room full of people watching something they can’t rewind. If you’ve ever wondered what 23 years in the trenches of live performance teaches you about leadership, community, and human connection — this one’s for you.  Real stories. Real business. Every Friday. Company Websites: https://www.milesquaretheatre.org/ Instagram: @milesquaretheaterTikTok: @milesquaretheater