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

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...

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with cloud-native workflows and seamless collaboration, hardware engineers were drowning in disconnected spreadsheets, outdated desktop software, and six-month onboarding cyc...

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 Ge...

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...

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 acce...

Many founders obsess over product, pitch decks, and projections—yet overlook one of the biggest red flags investors catch immediately: your growth isn’t actually scalable. In this episode of Margin for Error, Plug and Play Ventures investor Kayon Moshiri breaks down the signals founders miss when trying to raise capital. Kayon shares why early traction built on personal networks doesn’t impress in...

David Tswamuno's path to venture capital wasn’t traditional, it was deeply personal. Shaped by early lessons from his father about business and service, David built Fairbridge VC around a simple but powerful idea: capital with character. As General Partner, he backs founders tackling the biggest socio-economic challenges across health, wealth, and the planet—where opportunity meets responsibil...

Lawrence Kao didn’t follow the straight path into entrepreneurship. A self-described “lost computer science student,” he blended technology, media, and community into a career building startups at the intersection of fandom, digital platforms, and e-commerce. From co-founding VC-backed ventures to leading creative studios, Lawrence has spent decades turning chaos into clarity—and passion into busi...

Olivia O’Sullivan didn’t take the classic VC path. A former marketer and product builder, she zig-zagged from McDonald’s to Dow Jones to venture—carrying a zero-to-one obsession the whole way. Now Partner & COO at Forum Ventures, Olivia helps founders validate fast, sell sooner, and raise smarter—often before there’s even a working prototype. In this episode, we get into how Forum’s studio, ac...

Min-Yi Shih didn’t follow a straight path into investing. He started in physics and engineering, moved through executive leadership roles, and only later pivoted into the startup ecosystem as an angel investor and advisor. That nonlinear journey—spanning hard tech, business operations, and global networks—now informs how he evaluates founders and helps startups grow. Today, as Chair of Due Diligen...

Monika Rodiqi didn’t take the traditional VC route. She didn’t start in finance or come from a long line of investors. Instead, she built her way into the venture world by doing the work—building products, managing teams, and scaling early-stage startups from the inside. Now, as an Investment Analyst at Berlin-based Express Ventures, Monika brings that builder’s lens to every investment decision....

Alex Waters isn’t your typical startup insider. He didn’t raise a mega round or exit a unicorn. But over the last 15 years, he’s built something arguably more transformative: pathways. As Executive Director of The Program Labs and a veteran of San Diego’s entrepreneurial community, Alex helps nonprofits and ecosystems design startup programs that work—especially for overlooked and underestimated f...

Ahmed Saad has worn many hats: founder, ecosystem builder, educator—and program manager at Oxford's Saïd Business School, where he helps idea-stage ventures become investment-ready startups. But before all that? He had a closet full of unsold Egyptian cotton t-shirts and a crash course in startup failure. In this episode, Ahmed shares his journey from launching a fashion brand in Egypt to shap...

In this episode, Maria Gonzalez-Blanch, Managing Partner at Crescent Ridge VC, unpacks a refreshingly honest take on building great companies without burning through capital. With a background spanning engineering, private equity, and startups, Maria brings a multidimensional lens to early-stage investing across a set of core pillars. This conversation also tackles AI as a founder equalizer, the p...

Stephen Hargett’s path into entrepreneurship wasn’t planned—it was earned through persistence, hustle, and a relentless openness to saying yes to what came next. In this episode, Stephen shares his deeply personal and refreshingly candid journey to founding wrkspace , a "workspace-as-a-service" platform offering fully managed space solutions for teams, events, and collaborators. But before co-foun...

Alan Rich has built and exited not one, not two—but three successful software ventures, including his latest startup, Y Meadows. In this episode, he shares a masterclass in long-haul entrepreneurship and what it takes to keep building, even when you've already crossed the finish line—twice. Alan’s journey begins with founding Elite Information Group alongside his father, building financial systems...

Lily Elsner, co-founder of Jack Fertility, shares how she’s helping reshape male reproductive healthcare—starting with the world’s first postal sperm testing kit. In this episode, Lily shares the origin story behind Jack Fertility, a startup pioneering the world’s first full semen analysis through the mail. Born out of a personal conversation during the pandemic and informed by both femtech experi...

Bilal Kaiser, founder and principal at Agency Guacamole, joins to share the journey of building a standout agency in a crowded industry—and why agility, creativity, and authenticity are key ingredients to long-term success. Starting from a solo venture to a 20-person agency serving national beauty and lifestyle brands, Bilal walks through the evolution of Agency Guacamole, what the name really mea...

Elianne Rodriguez, Executive Director of LEEAF (Los Angeles Economic Equity Accelerator & Fellowship), shares how a lifelong connection to small business—and a chance bus ride into downtown LA—sparked her mission to build more inclusive, community-rooted startup ecosystems. From selling Jordans and working multiple jobs, to launching a career in tech incubation and economic empowerment, Eliann...

Nassir Criss of Sixty8 Capital joins us to share how defying the traditional VC path—and logging time in the trenches as a startup operator—made him a sharper, more founder-focused investor. Before stepping into venture, Nassir had already helped build 15+ startups by age 22. That operational depth gives him a rare edge in early-stage investing: a real-world understanding of what it takes to bring...

In this episode, we talk with Sonya Petcavich, founder of Meowtel, to unpack how a deeply personal loss led to building the leading cat-sitting marketplace in the U.S. Sonya shares how her childhood cat, Miss Lily, inspired the founding of Meowtel—a platform born out of grief, guilt, and a bold desire to create a better life for cats everywhere. They dive into how Sonya bootstrapped the company, r...