What if the reason so many startups fail has less to do with bad ideas and more to do with skipping the hard but necessary stages of building? In this episode of Startup Builders & Backers, I’m joined by Gregory Shepard, founder of Startup Science and author of The Startup Lifecycle, a book grounded in five years of research and 5,800 pages of data on why startups win or don’t.

Gregory breaks down a new way of thinking about startup growth, one that goes far beyond the usual "idea to IPO" narrative. He introduces his seven-stage startup lifecycle and explains why standardization and optimization, two stages many founders overlook are essential for building something scalable and resilient. Instead of rushing from product to growth, Gregory encourages founders to take time to strengthen operations and margins first.

We also explore the common missteps that lead to early failure, from premature scaling and hiring flashy executives too soon to misunderstanding capital needs and overinflating valuations. Gregory’s guidance is blunt but clear: get the fundamentals right early, or risk building something unsustainable.

Beyond the book, Gregory has created the Startup Science platform, designed as a single entry point for founders to access everything from mentors and grants to classes and investor connections. It's a full-stack resource for entrepreneurs who want to go beyond theory and embed startup best practices into real workflows.

Gregory also shares his take on the current funding environment, why downturns are often the best time to start something new, and how resilience when engineered through structure, not just grit can turn tough times into defining moments.

Whether you’re building your first product or wrestling with scale, this is an episode that strips away the noise and offers a blueprint for what actually works.

Explore more at GregoryShepard.com and StartupScience.io.

What does it take to turn a bold idea into a billion-dollar company during one of the most unpredictable periods in recent history? In this episode of Startup Builders and Backers, we meet Avery Pennarun, Co-founder and CEO of Tailscale, who shares how a lean networking startup found its stride in the middle of a global pandemic and reshaped expectations for what secure connectivity can look like.

Before founding Tailscale in 2019, Avery had already built and sold a company to IBM, worked closely with senior leadership at Alphabet, and led engineering efforts at Google Fiber. His experience spans both massive tech enterprises and nimble, founder-led ventures. But Tailscale may be his most ambitious project yet. Designed to simplify secure networking, Tailscale removes the complexity and frustration that usually accompany corporate VPN setups, making it easier for teams of all sizes to connect devices across locations—without expensive infrastructure or weeks of onboarding.

As remote work surged and companies scrambled to secure distributed teams, Tailscale quietly gained traction. By delivering speed, usability, and compatibility with existing tools, the startup found its audience. In 2023, VentureBeat named it one of the top zero-trust startups to watch, and earlier this year, the team launched an enterprise-ready zero-trust VPN that’s already drawing attention from major customers.

In this conversation, Avery opens up about the personal and strategic decisions behind Tailscale’s rise. He reflects on product-market fit, the importance of saying no to unnecessary complexity, and how the team remained focused under pressure. For anyone building in the infrastructure or security space, this is a rare look behind the curtain.

We also zoom out to examine the growing interest in zero-trust security models. While the term often gets thrown around in sales decks and funding pitches, Avery provides clarity on what it really means, how Tailscale approaches it, and why simplicity is often the most powerful form of security.

From scaling smart to staying grounded, Avery’s story is one that early-stage founders and first-time builders will find relatable and energizing. It’s proof that you don’t need a huge team or deep pockets to build something impactful—you just need to solve a real problem better than anyone else.

If you're building in public, navigating investor conversations, or sketching out your MVP, this episode offers both perspective and encouragement. Where could simplicity take your startup?

What does it mean to truly invest in a tech startup? In this episode, we explore that question with Frederic Joye, co-founder of Arcanys and partner at Arcanys Ventures. With a career that took him from the Swiss finance sector to the beaches of the Philippines, Frederic shares a philosophy that reshapes how we think about startup funding. For him, capital is only part of the equation. Real investment means giving startups access to seasoned engineers, technical mentorship, and operational insight.

We unpack Frederic’s unique journey into entrepreneurship—leaving a conventional career behind for the chaotic thrill of building tech companies in emerging markets. He discusses how Arcanys has become a launchpad for early-stage SaaS businesses, offering more than cash by embedding engineering talent directly into the startup's development process.

You'll hear Frederic’s perspective on what makes a startup truly investable: strong, experienced teams, early traction, and smart use of limited funds. He also reflects on the evolution of distributed software development, revealing how startups can tap into global talent while maintaining cohesion and speed.

Whether you're a founder looking for smart capital or a tech leader navigating distributed teams, this episode is packed with candid insights on sustainable growth, building resilient teams, and staying agile in a fast-changing tech environment.

What role should investors play beyond the wire transfer? And how can tech leaders use distributed talent to outpace competitors? Let’s find out.

As climate risks escalate and wildfires grow more frequent and destructive, how can startups help the insurance industry adapt and evolve? In this episode of Startup Founders and Backers, we spotlight how Firebreak Risk uses artificial intelligence to change how insurers assess and underwrite wildfire risk, while empowering homeowners to protect their properties.

Seetal Chohan joins us from Firebreak Risk to explore how the company’s AI-driven platform transforms user-submitted images and video into actionable data for insurers. Their goal? To close the gap between homeowners’ mitigation efforts and insurance eligibility and pricing. With Firebreak, homeowners can actively reduce their risk, and insurers gain a more thoughtful, more dynamic way to evaluate and price policies. According to Seetal, homes mitigated using Firebreak’s guidance are 40% more likely to survive a wildfire.

This episode also examines the role of the Lloyd’s Lab Accelerator, part of the world-renowned Lloyd’s of London insurance marketplace. Seetal shares how the accelerator’s unique program connects insurtech startups with mentors and domain experts to co-create solutions that address emerging challenges. With 85% of startups forming commercial relationships through the program, the Lab is a launchpad for meaningful change in insurance innovation.

Key discussion points include:

• How Firebreak Risk leverages AI to turn homeowner data into underwriting intelligence
• Why startups like Firebreak are helping insurers move faster on climate risks
• The importance of linking individual mitigation actions to tangible insurance outcomes
• How Lloyd’s Lab is building bridges between cutting-edge startups and industry stakeholders
• Opportunities for other founders to join the next Lloyd’s Lab cohort

From climate adaptation to AI-powered underwriting, this episode offers a clear view of how new ideas are reshaping one of the world’s oldest industries. Whether you're building a startup or backing the next wave of innovation, this conversation shows what's possible when tech meets tradition with purpose.

What does it really take to scale a startup from an idea to a thriving business generating over $100M in ARR? In this episode of Startup Builders & Backers, we explore that journey with Luke Diaz, founder of DBT Ventures, an angel investment fund focused on supporting underrepresented founders. Drawing on his extensive background leading customer success teams and scaling early-stage companies, Luke shares powerful lessons on driving product adoption, boosting retention, and practicing conscious leadership.

Our conversation uncovers practical strategies that founders can apply immediately, from structuring effective onboarding programs to understanding churn before it becomes a problem. Luke emphasizes that customer success is not just a department but a foundational philosophy that impacts every area of a startup’s growth trajectory. His advice on creating a transparent culture of continuous improvement offers a refreshing look at how leadership style directly influences business outcomes.

Beyond operational tactics, Luke offers a candid view of the funding landscape, sharing tips on how startups can better quantify their potential, attract the right investors, and overcome the biases that still exist within traditional venture capital ecosystems. His commitment to supporting diverse founders highlights an important shift happening across the industry.

We also discuss emerging technologies and the importance of focusing on business outcomes rather than getting caught up in the latest hype. Luke’s insights on integrating tools like ChatGPT into business operations offer a grounded perspective on how startups can use AI to enhance decision-making without losing sight of the fundamentals.

Whether you're an aspiring entrepreneur, an investor seeking promising ventures, or a startup operator focused on scaling sustainably, this episode offers practical, real-world insights that go beyond the headlines. Tune in to discover how conscious leadership and strategic customer success can help unlock the true potential of your venture—and why a focus on people, not just products, might be the key to long-term success.

What should tech startups know before expanding beyond their home market?

In this episode of Startup Founders and Backers, we explore that very question with Dr. Shan Nair, president of Nucleus and a pioneer in international expansion services. With a background that began in nuclear physics at Oxford and led to advising globally recognized names like Tesla and FaceTime, Shan brings a rare blend of analytical precision and hands-on business experience to cross-border growth.

Our conversation covers the full spectrum of what startups must consider when scaling internationally. Shan outlines the most common expansion scenarios, including companies hiring their first overseas employee or those already present in multiple countries struggling to manage operations effectively. He explains how Nucleus provides a single point of contact across legal, financial, and compliance services, helping avoid the confusion and risk of using separate vendors in different regions.

We also examine how legal requirements and regulatory expectations differ across regions. Shan shares specific insights into employment law exposure in Europe and Latin America, the changing rulebooks in Asia-Pacific, and the intricate compliance landscape in India. He underscores the importance of working with finance leaders who understand international complexity and why a realistic budget is just as important as the product itself.

Looking toward the near future, Shan offers his thoughts on the role that technologies such as cryptocurrencies and modular nuclear energy might play in reshaping international operations. He also reflects on how protectionist policies may influence where companies manufacture and how they hire.

Whether preparing for your first overseas hire or rethinking your entire expansion strategy, this episode offers clear, experience-backed insights for founders who want to make smarter decisions when taking their startup global.

What would you consider the biggest challenge in going international? Let us know, we'd love to hear your perspective.

How is AI changing the rules of intellectual property, and what should founders be doing about it? In this debut episode of Startup Builders & Backers, we tackle one of the most pressing and under-discussed areas in the startup space: the legal impact of AI.

I’m joined by Alex Watt, commercial IP lawyer at Howard Kennedy and leader of the firm’s startup programme, Ignite. With deep expertise across licensing, branding, advertising, and digital rights, Alex offers a practical perspective on how emerging technologies are testing the limits of today’s IP frameworks.

We explore the growing debate around copyright exemptions for AI training, the risks of unclear ownership in AI-generated content, and why startups must revisit their licensing agreements as AI becomes part of the product stack. The conversation also covers how legal teams are preparing for AI-generated influencers, how the metaverse might bring IP into uncharted territory, and what it really takes to futureproof your startup’s rights in an increasingly automated world.

If you’re building something new and wondering how to safeguard it—this episode offers clarity. Alex also shares advice on early-stage IP protection, from trademarks to SEIS/EIS structuring, and why getting this right at the outset saves significant pain down the line.

As AI accelerates innovation across industries, how can startups strike the right balance between moving fast and staying protected? And what new rules are likely to emerge in the years ahead? Tune in and join the conversation. I’d love to hear your take.