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 investors, what real customer acquisition looks like, and how to prove you can grow beyond the “first five customers.”Drawing from his experience evaluating hundreds of startups across retail, commerce, and AI, Kayon reveals what actually moves an investment forward—and what quietly kills a deal. From solo-founder risks to unrealistic projections, he lays out the patterns investors pay attention to long before founders do.Here’s what’s covered:• The red flag that instantly weakens your pitch• Why first customers don’t equal repeatable traction• What scalable growth looks like (and what it doesn’t)• The founder traits that build investor confidence• When “working harder” becomes a liability• How to avoid fundraising too late• Why ownership, team composition, and accountability matter• What today’s macro environment means for early-stage foundersIf you’ve ever wondered why investors aren’t buying in—even when you think you’re ready—this conversation shows you the blind spots that matter most.
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 responsibility.
In this episode, David shares how his life experiences, from banking to impact investing, inspired Fairbridge’s mission to fund startups solving real-world problems. He opens up about the challenges of launching a first-time fund, why empathy is a founder’s superpower, and what makes the best investor-founder relationships thrive.
From investing in labor innovation to rethinking access, fairness, and technology’s role in social progress, David brings clarity to the intersection of purpose and performance.
Here’s what’s covered:
• The story behind capital with character and why it matters
• Building a fund that bridges health, wealth, and the planet
• Four core criteria Fairbridge uses to evaluate startups
• What founders misunderstand about fundraising
• The “wide discrepancy” test for meaningful innovation
• How empathy drives better products—and better investors
• The difference between momentum and lasting product-market fit
• Rethinking AI as a tool, not a strategy
• The future of impact investing and emerging managers
• Why building a startup is both a privilege and a responsibility
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 business models.
Now, as co-founder of The Companion, Lawrence is reimagining fandom not just as entertainment, but as connection, community, and even mental health support. His journey spans the early YouTube era, partnerships with studios like MGM, and a pandemic-era rebuild that placed purpose and people at the center.
In this episode, Lawrence shares lessons from scaling startups, why distribution always beats production, the “tattoo test” for brand loyalty, and how fandom can inspire both belonging and business.
This is a conversation about resilience, reinvention, and the power of community-driven strategy.
Here’s what’s covered:
The “Tattoo Test”: what it reveals about true brand devotion
Why distribution > production in digital media
How to build healthier communities (and avoid “poo in the pool”)
Lessons from YouTube’s early growth days and Copa90
40 pitches in 40 nights: saving a company under pressure
The MGM/Stargate project and the risks of relying on one client
Rebuilding The Companion during the pandemic
Using fandom to combat loneliness and support mental health
How founders can validate ideas with revenue, not just hype
Staying close to customers, making hard calls, and finding the right mentors
Learn more about The Companion and Lawrence’s work to turn fandom into community (link here).
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, accelerator, and seed fund back B2B founders from day zero—and why brutal idea-killing, customer pull, and willingness to pay are the real green lights.
Here’s what’s covered:
Forum’s 3-track model: concept-led studio, rolling pre-seed accelerator, and pre-seed/seed fund
The “kill ideas fast” playbook—finding real problems and real WTP before code
Why Forum won’t launch a studio company without signed customer contracts
What platform actually means in VC—and how it drives sourcing, GTM, and fundraising
Coaching technical founders on sales: discovery calls, enterprise motion, and common pitfalls
Founder-market fit, execution signals, and how to avoid “false positives” in validation
A studio case: partnering into IBM and hiring the founding engineer to unlock scale
The Forum Foundry: a 4-week validation sprint with capital for the winners
Learn more about Forum Ventures and Olivia’s work helping founders go from concept to customers (link here).
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 Diligence at Tech Coast Angels and Director at the Taiwan Global Eastbound Association, Min-Yi bridges worlds: technology and business, Asia and the U.S., investors and founders. His story is about staying curious, building resilient teams, and finding joy in the process of innovation.
In this episode, we talk about what investors really look for at the earliest stages, why pitch decks often miss the point, and how international collaboration creates opportunities far beyond capital. Min-Yi also shares his philosophy on curiosity as a lifelong strategy, the realities of global expansion, and what it means to balance optimism with practicality.
This is a conversation about mindset, markets, and the bridges that make startup ecosystems stronger.
Here’s what’s covered:
• Why founders—not just business models—determine startup outcomes
• The most overlooked element of a pitch deck (and why business plans still matter)
• Product-market fit vs. hype: what actually attracts investment
• How curiosity and joy fuel resilience in the startup world
• Lessons from reviewing dozens of startups each month at TCA
• Why cross-border collaboration between Asia and the U.S. is a growth multiplier
• Advice for international founders entering the U.S. market
• How to stay adaptable in a world of constant change
Learn more about Tech Coast Angels and Min-Yi’s work supporting global founders (link here).
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. Express Ventures focuses on logistics and industrial startups, but Monika’s story is about more than sectors—it’s about signal.
In this episode, we talk about what makes a founder stand out, why story matters more than polish in a pitch deck, and how venture can be both strategic and socially conscious. Monika also shares her thoughts on Europe’s startup evolution, the realities of being a woman in tech, and what she’s watching in robotics, AI, and the future of fueling.
This is a conversation about strategy, bias, and the decisions that shape tomorrow’s market leaders.
Here’s what’s covered:
Why agility is a startup’s biggest advantage
What VCs really look for at the pre-seed stage
The one thing every founder should do in a pitch meeting (but rarely does)
What makes Berlin a unique tech ecosystem—and why you shouldn’t write it off
How CVCs can offer more than capital
The power of founder-investor alignment
Why VC is an asset class, not a moral compass—but still shapes the world
The troubling truth behind VC’s gender funding gap—and what might actually change it
Learn more about Express Ventures and Monika’s work to bring more builder-mindsets into venture (link here).
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 founders.
In this episode, we talk about how Alex moved from edtech founder to ecosystem architect, why access (not ambition) is the biggest startup divide, and what it really takes to build programs that empower communities instead of checking boxes.
This is a conversation about the systems behind startups, and the humans who make them work.
Here’s what’s covered:
Why Alex left startup building to become a startup builder
The difference between inviting founders to the table and setting a seat for them
What makes a program truly inclusive (hint: it’s not just good intentions)
Challenges underrepresented founders face that others often don’t see
What the U.S. startup narrative gets wrong about failure
Lessons from building San Diego’s first business accelerator for diverse founders
Learn more about The Program Labs and their work to make innovation infrastructure more equitable (link here).
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 shaping one of the UK’s most influential university entrepreneurship programs. We dive into what makes a great founder, how to build support systems around early-stage innovation, and what it really takes to turn research and raw ideas into real companies.
With experience across startups, accelerators, policy, and academia, Ahmed offers a 360° view on entrepreneurship that’s as honest as it is energizing.
Here’s what’s covered:
How Ahmed’s first venture failed—but sparked a career in entrepreneurship
What working across government, coworking spaces, and academia taught him about startup needs
Why supporting early-stage founders requires empathy and structure
The goals and impact of the Oxford Venture Builder program
Lessons from helping students, scientists, and engineers become entrepreneurs
What makes a university startup ecosystem thrive (or fall short)
How to connect research with real-world value
Building an inclusive path for deep tech and mission-driven ventures
Learn more about the Oxford Said Entrepreneurship Centre (here) and the Oxford Venture Builder Programme (here)
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 power of self-awareness in founder-investor fit, and why venture capital should be a canvas, and not a cookie-cutter playbook.
This is an episode about thoughtful investing, founder empowerment, and rewriting the rules of venture.
Here’s what’s covered:
The philosophy behind Crescent Ridge VC and its “health, people, planet” pillars
Why capital efficiency is a strategic advantage, not a constraint
The pros and pitfalls of AI-powered startups in today’s venture landscape
What Maria looks for—and avoids—in early-stage investments
Advice for founders navigating today’s macro environment and investor dynamics
Why VC should be more art than science—and what that means for building companies with soul
Learn more about Crescent Ridge VC: https://www.crescentridge.vc
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-founding wrkspace, Stephen was figuring things out one step at a time—from moonlighting as a boarding school teacher to making 1,000 cold calls a day at a pre-IPO startup, to working at Apple during the iPhone 4 launch (and, yes, emailing Steve Jobs).
Through it all, Stephen learned how to navigate ambiguity, stay mission-aligned, and build community—and wrkspace is the product of those lessons.
Here’s what’s covered:
Learn more about wrkspace: https://www.wrkspace.app/
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 for law firms before scaling it globally and selling to Thomson Reuters. Then came Chrome River Technologies, a venture into enterprise expense reporting that served clients like Toyota and Exxon. Today, Alan is back in the arena—this time with his two sons—leading Y Meadows, a company using AI to automate customer service and operations.
Through these ventures, Alan has navigated evolving industries, scaling challenges, and the emotional cycles of starting (and restarting) companies. This conversation reveals how he’s kept the passion alive, the lessons he brings into each new venture, and why the sales engine—more than the tech—is the ultimate startup differentiator.
Here’s what’s covered:
Learn more about Y Meadows here: https://ymeadows.com
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 experience and rural agricultural insights, Lily and her team set out to build a product that reimagines access to male reproductive healthcare.
Fertility is often framed as a “women’s issue,” despite research showing that male factor infertility accounts for over half of all cases—and in many of those, the issues are preventable or reversible. Yet testing has remained inaccessible, awkward, and stigmatized. Lily breaks down why that’s a systemic problem, how it affects IVF outcomes, and what Jack Fertility is doing to close the gender health gap.
She also discusses the biological realities of sperm health—how it regenerates every 74 days and how lifestyle changes can make a measurable impact—while highlighting why men, just like women, deserve proactive tools for understanding and managing their reproductive future.
This is a conversation about science, stigma, and startup resilience.
Here’s what’s covered:
Learn more about Jack Fertility here: https://www.jackfertility.co.uk/
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 means, and how he’s stayed ahead of shifts in the creator economy, PR, and digital marketing.
Here’s what’s covered:
Learn more about Agency Guacamole here: https://www.agencyguacamole.com
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, Elianne’s story is a testament to resourcefulness, grit, and the belief that startup knowledge should be accessible to all. This episode explores her journey, the mission behind LEEAF, and what it really means to center equity in entrepreneurship.
Here’s what’s covered:
Growing up in a side-hustle-driven immigrant household
Finding her way into the startup world without traditional access
Launching a tech incubator to demystify venture building
How LEEAF supports founders from underserved communities
Why language, location, and lived experience matter in program design
Learn more about LEEAF: https://www.calstatela.edu/leeaf
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 ideas to life. This conversation dives into the gaps in the VC status quo, the value of founder empathy, and why endurance—not just intellect—drives success.
Here’s what’s covered:
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, raised minimal VC funding, and still scaled Meowtel to eight-figure annual revenues—all while navigating a fundraising landscape dominated by dog people.
In this episode we explore:
Learn more about Meowtel at www.meowtel.com