Margin For Error: The Story of Entrepreneurs, Investors and Platform Builders

EP 21 | They Raised $60M to Fix What Stripe Can't. Here's How | Jo Elias Phillips and Will Corbera, Payabli

Jo Elias Phillips and Will Corbera, co-founders of Payabli, are building the payments infrastructure that software companies have been waiting for. After meeting at a salsa club in Miami over 15 years ago and bonding over entrepreneurship, they set out to solve a problem they saw firsthand: vertical SaaS platforms were losing time, money, and customers trying to stitch together fragmented payment solutions that were never built for them. Will bootstrapped his first payments company for 17 years before a successful exit. Jo helped architect what became ServiceTitan's payments business, now processing $60 billion in annual volume. Together, they combined those experiences into Payabli, a unified pay-in, pay-out, and pay-ops platform that helps software companies embed and monetize payments without building everything from scratch. The company has raised $60 million in venture capital, serves close to 100 partners, and processes tens of billions of dollars in volume. This episode explores their origin story, the lessons they carried from previous startups, and why they believe the future of payments belongs to the platforms, not the legacy processors. Here's what's covered: * Why most SaaS companies underestimate what it takes to monetize payments after integration * How Payabli unified pay-ins, pay-outs, and pay-ops to eliminate vendor fragmentation * How AI is reshaping their product, operations, and long-term vision for scaling without headcount bloat If you've ever wondered why your payment integration isn't generating the revenue you expected, this conversation shows you what's missing.

EP 20 | VCs Said the Market Was Too Small. Every Product You Own Proved Them Wrong | Michael Corr, Duro

Michael Corr, founder and CEO of Duro, spent years designing circuits and manufacturing products before realizing the tools hardware teams relied on were stuck in the 1990s. While software teams were shipping faster than ever with cloud-native workflows and seamless collaboration, hardware engineers were drowning in disconnected spreadsheets, outdated desktop software, and six-month onboarding cycles. So he decided to change that. Duro is a product lifecycle management platform built for modern hardware teams. Think of it as GitHub for hardware: centralizing CAD files, supply chain data, and manufacturing workflows into one connected system that teams can be running on in days, not months. With a recent ground-up rebuild designed to be AI-native from the start, Duro is pushing hardware engineering into a new era.From bootstrapping when no VC would invest in hardware, to navigating COVID supply chain chaos, to rebuilding the entire product from scratch, Michael shares the full journey of bringing a decades-old industry into the modern age. Here's what's covered:  * Why hardware engineering tools are decades behind software and what's finally changing  * How Duro acts as the "GitHub for hardware" with centralized data and revision control  * The real reason Michael bootstrapped for years (hint: it wasn't by choice)  * Why the team rebuilt the entire product from scratch to be AI-native  * What COVID and tariffs exposed about supply chain fragility and how Duro helped teams adapt  If you've ever wondered what it takes to modernize an industry that hasn't changed in decades, this is the conversation.

EP 19 | She's Behind Nearly 50% of Funded Startups at Her Firm. Here's What Your Pitch Is Missing | Jasmine Ober, Pitch Genius

Jasmine Ober, founder and CEO of Pitch Genius, has spent nine years helping startups do what less than 1% ever pull off: actually get funded. With a close rate nearly 50x the industry average, her firm doesn't just design pitch decks. It builds the entire fundraising engine, from the first hook that gets an investor to keep clicking, to the data room that closes the deal. Before launching Pitch Genius, Jasmine sat in angel investor rooms watching founders botch their biggest moment. Not because they didn't care, but because nobody taught them what "prepared" actually looks like. That gap became her mission. In this episode, she breaks down her methodology for crafting pitches that stand out in crowded markets, why most founders rush into fundraising before they're ready, and how AI is reshaping the landscape without replacing the critical thinking investors still demand. Here's what's covered: • Why the hook of your pitch matters more than the overall story • How one AI startup closed most of its Series B extension within a week • The mindset shifts and time commitments founders underestimate about fundraising • How AI tools speed up research but still can't replace critical thinking • The one test every founder should run on their pitch deck this week If your competitor could have written your exact same pitch, you haven't differentiated enough. This episode shows you how to fix that.

EP18 | How PR Actually Works: Building Brand Credibility That Lasts | Lauren Banyar Reich, LBR/PR

Most founders think PR is about making one phone call or going viral overnight. Lauren Banyar Reich, founder of LBR/PR, has spent ten years proving otherwise. In this episode of Margin for Error, Lauren shares how her agency builds lasting brand credibility through deep storytelling, long-term client relationships, and a proactive approach to media strategy. Lauren opens up about why she left the traditional agency world to create a firm that does great work without burning people out. She breaks down the misconceptions that trip up founders, from expecting instant virality to underestimating the strategy behind a single pitch. She also shares standout client stories, including a construction company that landed a front-page feature leading directly to a new business meeting, and an inclusive fashion brand whose co-founder appeared on CBS News to discuss how Ozempic is reshaping the industry. The conversation also covers two newer initiatives: LBR/PR Women, which supports brands focused on making women's lives better across healthcare, finance, and beyond, and PR in a Box, a done-with-you toolkit that gives startups and small businesses the building blocks to pitch media on their own. Here's what's covered: * The PR misconceptions that keep costing founders time and money * What your brand needs to have in place before pursuing media coverage * Behind the scenes of client wins that turned earned media into real business * Two initiatives expanding access to PR for women-focused brands and startups * The one move you can make this week to start getting on the media's radar

EP 17 | He Reviews 1,000+ Startups a Year. Here's What Founders Get Wrong | Lucas Pols, 1752VC

Lucas Pols, managing partner at 1757VC (formerly Pegasus Angel Accelerator), has spent the last decade investing in and building alongside early-stage founders. He's not the type of investor who writes a check and walks away. With a 0.3% acceptance rate and hands-on involvement that includes helping hire, fire, and rethink go-to-market strategy from the ground up, 1757VC is redefining what an accelerator can do for startups at their inflection point. From his early days knocking on doors in sales to leading one of the nation's largest angel networks, Lucas brings operator-level empathy to the investor seat. In this episode, he breaks down how 1757VC drives outsized MRR growth, why AI is reshaping fundraising expectations overnight, and what separates the founders who break through from those who stall out. Here's what's covered: * What it really means to invest at a startup's inflection point * The growth hacking strategies behind 1,000%+ MRR portfolio results * How AI is completely rewriting the rules on startup growth timelines * Why most pitch decks lose investors before slide seven * The one exercise every founder should try this week If you've ever wondered what separates the startups that break through from those that plateau, this conversation lays out the playbook.