The Founder's Gambit
The Founder's Gambit is a podcast where host Gabriel interviews real founders about their entrepreneurial journeys. Each episode digs into how they got started, the big risks they took, and the failures they encountered along the way. Guests share honest stories and hard lessons rather than polished success narratives. The goal is to offer practical insights for anyone building or thinking about building a real business.
Episodes
How I Raised $10.5M From a16z With a Boring Startup
Oskar Block made $1M ARR at 18 building sports-betting models, walked away because it didn't feel meaningful, joined McKinsey to hunt for a real problem, and left the week before Christmas to build AI agents for patent litigation. Six months later, Stilta had gone from $18K to $102K ARR in two weeks during YC and raised $10.5M from Andreessen Horowitz. In this episode, he breaks down exactly h
How I'm Building a Billion Dollar Company
A girl cancelled their dinner reservation the day of. Rather than eat the $100 cancellation fee, Jeff Wulkan built an app to find a replacement, then quit a 20-year aviation career and put $250,000 of his own money into it. Today Plus One is adding roughly 7,000 users a month on a lean budget, 60% of them organic, while marketing in exactly one state.What we cover:- The cancelled date that started
How My App Launch Made $65K in 3 Days (No Ads, No Funding)
Deven walked away from Amazon to build his own thing. Two years later, his product Supergrow serves 1,000+ customers across 53 countries, and one lifetime deal launch brought in $65K in just a couple of days. In this episode, he breaks down how he escaped big tech, found his first paying customers, and built a team of 7 without losing the freedom he quit for.What we cover:- Why he traded an Amazon
I Built 5 SaaS Apps to $1 Million MRR: Here’s My Playbook
Tibo Maker sold two companies for $8M, then did the opposite of what everyone expected. Today he makes $1M+/month from five small SaaS products, fully bootstrapped, with zero outside funding. In this episode, he reveals exactly how he builds, validates, and scales products without ever raising a dollar.What we cover:- Why two startups failed before anything worked (and the ego trap that killed the
Why Developers Don't Write Code Anymore
Senior developer Ilija reveals he writes ZERO lines of code anymore and ships 4x faster than before. In this episode, he breaks down exactly how AI transformed his entire development workflow and what it means for the industry.What we cover:- How his team went "full AI" and stopped manual coding completely- The meta-workspace setup that manages multiple codebases- Why token costs hit $200 in 4 day
How I Built a $14,000/Month SaaS with 0 Employees
Andris Reinman makes $14,000/month with zero employees selling software he gives away for free. In this episode, he reveals exactly how he turned his open source email library into a profitable solo business.What we cover:• How he monetized 10milion+ weekly NodeMailer downloads• The license key pivot that changed everything• Why he rejected VC money and whale customers• His "download, don't host"
I Turned My Procrastination Problem Into a Business
Taylor Jacobson (10-year CEO of Focusmate, 12M+ sessions across 175 countries) reveals why procrastination isn't laziness, it's your nervous system protecting you, and how he turned this insight into a virtual co-working platform that's changing how millions work.What we cover:• Why procrastination is actually your body being smart• The nervous system science behind focus vs. fight/fli
OpenClaw: AI Agent That Made me Fire My Intern
Paul Chiappetta (2-time exited founder, Fractional CTO) reveals how OpenClaw transformed his business operations and shares a conspiracy theory about Claude that might explain why security breaches are increasing across the internet.What we cover:- Why it's the worst time ever to build a startup- The exact OpenClaw workflow that replaced my intern- From 4% to 19% reply rate: the complete break
How to Go From Idea to Product in Days | Dan Mindru
Dan Mindru has shipped 15+ products and found a way to build them in days, not months. In this episode, he breaks down his exact AI workflow that lets him go from idea to deployed product overnight.What we cover:- How he codes products while sleeping (AI night shift method)- Why most developers fail at shipping (and how to fix it)- The wedding app he built in 1 week between our calls- Docker sandb
25 Years of Startups Taught Me This | Dennis R. Mortensen
In this episode of The Founder's Gambit, I sit down with Dennis Mortensen - a serial entrepreneur with 25 years, 5 ventures, and 4 acquisitions under his belt.Dennis breaks down:• Why he thinks of entrepreneurship as a "50-year fund"• The mindset that eliminates fear of failure completely• How founders "live in the future but document the past"• Why having kids early is a &
She Left Her Dream Job at Discord to Build an AI Startup (Here's What Happened)
After 15 years climbing the ladder at Microsoft, Meta, and Discord, Apurva had everything - a dream job, resources, and a title. Then she left it all to build an AI startup from scratch.In this episode, Apurva breaks down:- Why she left her "dream job" at Discord to become a solo founder- How AI removed her biggest excuse: "I have an idea but can't build it"- The brutal rea
From $8K to $35K/Month: He Rebuilt His Entire SaaS Alone
Brennan Dunn raised $500K, hired a team of six, and built the wrong product. His SaaS, RightMessage, went from $30K/month down to $8K as both co-founders checked out. Instead of shutting it down, Brennan bought his co-founder out, rebuilt the entire product from scratch by himself, and took it back up to $35K/month. No team, no new funding, just him.In this episode, Brennan breaks down:- Why raisi
He Quit His Job With No Plan, Now He Has 800+ Customers | Dmytro Krasun
Dmytro quit his engineering job with no product, no idea, and zero plan. He had savings, a wife with a job, and this nagging feeling that he'd regret it if he didn't try.Then... nothing happened. For two years. Almost no revenue. Money burning every month. He picked up freelancing on the side just to stay alive.Eventually, he built ScreenshotOne, a screenshot API now used by 800+ paying bu
He Built a $20K/Month SaaS From a Weekend Project (No BS Guide) | Lukas Hermann
Lukas Hermann built StageTimer as a weekend side project. Click start on one screen, a timer shows on another. That was it. No funding, no team, no marketing budget to start. Today it makes over $20,000 a month, runs at conferences and live events worldwide, and his logo even showed up on screen at a Trump event without him knowing.In this episode of The Founder’s Gambit, Lukas walks through the e
He Built 15 Failed Products, And Now Makes $17K/Month | Denis Yurchak
Denis Yurchak studied international relations, taught himself to code at 22, failed at 15 products, cloned a competitor's idea, and built Yadaphone, a Skype replacement that now makes $17,500 a month. All as a solo founder with no team and no funding.In this episode, Denis breaks down:→ How he went from a humanities degree to shipping products as a solo dev→ Why his first 15 ideas failed (incl
He Runs 7 AI Agents While We Talk - How AI Killed the Dev Team
Julian Wagner started building businesses at 16, from quiz websites and nightlife events in Frankfurt to scaling an online poker school to $5M in revenue in just 18 months. Now he's a technical co-founder running AI agents while he sleeps.In this episode, Julian breaks down:→ How he went from paying $30 for a poker hand review to building one of the biggest poker schools in the world→ The mark
Why Only 15% of People Finish Buying (And How Greg Got It to 60%)
Most creators obsess over getting more traffic. But what if the real problem is that 85% of people who reach your checkout… never finish buying?🔗 Check out Easy Tools: https://easy.tools🔗 Find Greg on X: @gregg.rogIn this episode, Greg, founder of Easy Tools (easy.tools), breaks down exactly why most checkouts are broken and how he built a platform that consistently hits 50-60% checkout conversion
How To Actually Get High‑Paying Clients On Upwork In 2026 | Nico Hessel Interview
Nico Hessel went from a college soccer goalkeeper with three surgeries, dropping out, getting kicked out by his parents, and sleeping in a 2014 Honda Civic… to scaling a marketing agency to $15,000/month in 4 months using only Upwork, then helping hundreds of freelancers and agencies turn Upwork into a real acquisition channel instead of a side hustle lottery ticket.In this episode we get into:- H
Why Founders Keep Getting Burned by Developers (A Senior Dev Explains the Truth)
Founders complain that developers overpromise, miss deadlines, and disappear.Developers complain that founders are unclear, unrealistic, and chaotic.So who’s actually right?In this episode of The Founder’s Gambit, I sit down with Ilija Vuk, one of the most reliable senior developers I’ve ever worked with. He’s helped rescue broken MVPs, push back on bad product decisions, and turn half-baked ideas
He Walked Away From Millions: Ex-Zendrop President Betting It All On His Startup
Ben Furtado walked away from millions as President of Zendrop, one of the fastest-growing ecommerce platforms in the US, after helping 10x revenue and complete a merger… to start from zero on a pre-revenue startup called Moonlite Money.In this episode we get into:Why he walked away from millions in salary, bonuses, and equityThe idea of “strategic luck” and how to actually increase your luck surfa
From 9-to-5 to Running Google Ads That Drove $100M for Clients
In this episode of The Founder’s Gambit, Gabriel sits down with John Martin, founder of Paid Ads, a Google Ads agency that has managed campaigns generating more than $100 million in client sales.John’s journey started in a traditional 9-to-5 marketing job in the UK, where he first discovered the power of digital advertising. After seeing one young digital marketer outperform an entire traditional
How Michael Gardiner Built a $2M Agency While Traveling the World
In the very first episode of The Founder’s Gambit, host Gabriel sits down with Michael Gardiner, founder of Done For You Meetings, a B2B lead generation agency he scaled to over $2 million in revenue while traveling to more than 60 countries.Michael started building online businesses as a teenager, accidentally launching his first influencer marketing agency at just 14. Over the years, he’s become
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