In this episode of Startup Builders & Backers, I speak with Connor McKenna, co-founder and CEO of Go Swag. His story begins in a Glasgow software agency, where he and co-founder Ben wanted to create a memorable first day for a new employee arriving from Italy.

The welcome gift made an immediate impression and was shared across social media. When Connor suggested creating the same experience for every new employee, colleagues explained how difficult the process would be to repeat across the company.

Connor and Ben searched for a corporate gifting provider capable of managing design, sourcing, branding, logistics, and international delivery from beginning to end. When they could not find one, they launched Go Swag with approximately £180.

Their lack of corporate gifting experience became an advantage because they approached the industry from a software background. Previous work involved building digital products for slow-moving sectors such as banking and pharmaceuticals. Go Swag applied the same thinking to an industry where administration traditionally increased alongside revenue.

Connor explains the company’s DRY principle, meaning “don’t repeat yourself.” Administration, quoting, and logistics should be handled by software, allowing employees to concentrate on customer relationships and creative decisions.

This approach helped Go Swag grow without increasing headcount at the same rate as revenue. Neil notes during the interview that the business has achieved five consecutive years of triple-digit growth with a team of approximately 30 people in Glasgow.

We also discuss why the founders decided to build globally from day one. Corporate gifts sent to employees in India or South America should provide the same experience as packages delivered to London or San Francisco. Scotland’s smaller domestic market also encouraged the team to think internationally earlier than many startups.

Operating globally introduced difficult questions involving customs, tariffs, taxation, warehousing, and logistics. Go Swag launched in 2019 and subsequently faced COVID, Brexit, the UK mini-budget, rising energy prices, and changing tariffs. Connor jokes that he began the company with hair, which provides an unofficial measure of the pressure involved.

For founders pursuing enterprise customers, Connor advises against entering meetings apologetically. Large companies care about consistency, ownership, problem resolution, and avoiding surprises. A startup’s smaller size can offer an advantage because its team can move faster and provide forms of support that larger competitors struggle to approve.

Connor also discusses the discipline required to reject revenue. Smaller contracts may feel attractive during the early stages, but they can consume the time needed to pursue enterprise opportunities. He applies the same thinking to warehouses, international offices, and other investments that might impress people without solving a customer problem.

The conversation closes with Go Swag’s use of generative AI. Connor describes the “blank canvas problem” facing buyers presented with thousands of products and finishing options. Go Swag is developing models that begin with the buyer’s intended outcome and recommend an appropriate gift rather than expecting the customer to become an expert in printing techniques.

Could your startup grow faster by automating repeatable work, rejecting distracting revenue, and approaching enterprise customers with greater confidence? Listen to the episode and share your thoughts with me.

In this episode of Startup Builders and Backers, I sit down with Daren Hornig, founder and CEO of CourtsApp, to discuss how he spotted a major gap in one of the world's fastest-growing sports sectors and decided to do something about it. Drawing on decades of experience in real estate development and sports infrastructure, Daren set out to build what he describes as the Expedia of racquet sports, a platform designed to make finding, booking, and enjoying courts as simple as booking a hotel room.

Daren shares the origin story behind CourtsApp, from acquiring and revitalizing the historic Port Washington Tennis Academy to helping expand pickleball facilities across the Northeast. Along the way, he discovered a fragmented industry filled with disconnected systems, unanswered phone calls, and missed opportunities for both players and operators.

We also explore how artificial intelligence is changing the experience for clubs and players alike. Daren explains the role of Courtney, CourtsApp's AI-powered assistant, and how AI can help facilities improve customer service, reduce operational costs, and create more seamless experiences without requiring expensive technology teams or infrastructure investments.

Beyond the technology, this conversation is packed with lessons for founders. Daren talks openly about building globally distributed teams, moving from physical real estate projects into software development, and why speed, adaptability, and a willingness to solve real-world problems continue to create opportunities in unexpected places.

Whether you're a startup founder, sports enthusiast, investor, or simply fascinated by how technology is modernizing traditional industries, this episode offers an insightful look at what happens when entrepreneurship meets a market ready for change.

Could racquet sports become the next industry transformed by digital platforms and AI? I'd love to hear your thoughts.

In this episode of Startup Builders & Backers, I sit down with Russell Attwood, CEO of Route 101, whose entrepreneurial journey spans multiple decades, technology shifts, and economic cycles. From launching a business in a cupboard room to building and selling a multi-million-pound company, Russell's story offers a candid look at resilience, leadership, and the realities of building companies when conditions are far from ideal.

Russell shares how the 2008 financial crisis forced difficult decisions, including restructuring a successful business to ensure its survival, and how those experiences shaped his approach to leadership, cash flow management, and long-term growth. Rather than viewing entrepreneurship through the lens of overnight success, he offers a refreshing perspective on navigating uncertainty, backing yourself when others doubt you, and building teams that can weather challenging times together.

We also explore the story behind Route 101, a company name inspired by a family road trip down America's famous Highway 101, and how Russell spotted the shift from traditional technology projects to recurring cloud-based services long before many competitors. That insight helped shape Route 101 into a fast-growing customer experience and contact center specialist serving organizations across the public and private sectors.

The conversation naturally turns to one of the biggest topics facing businesses today: artificial intelligence. Russell explains why so many organizations are rushing headlong into AI without first putting the right foundations in place. He discusses the importance of customer knowledge, governance, and practical use cases that deliver immediate value, from agent assistance and call summarization to quality assurance and conversational AI.

Throughout our discussion, Russell brings a balanced perspective to customer experience, reminding us that while technology continues to evolve, customers still want the same thing they have always wanted: a simple, frictionless experience that solves their problems quickly and effectively.

Whether you're building your first company, scaling an existing business, or trying to separate genuine innovation from industry hype, this episode offers valuable lessons from someone who has successfully navigated multiple waves of change while keeping customers at the center of every decision.

What can today's founders learn from someone who has already survived the storms, rebuilt stronger, and chosen to start all over again?

In this episode of Startup Builders and Backers, I spoke with David Amsellem, founder of luxury concierge company John Paul and now Chief Distribution Officer at HBX Group, about entrepreneurship, innovation, and why the next generation of founders will win by orchestrating ecosystems rather than simply building standalone products.

David’s story is particularly fascinating because it spans two very different startup eras. He launched his first company at a time when entrepreneurs still had to justify why they weren’t pursuing traditional careers. Today, he sees a completely different environment where speed, agility, AI, and access to capital are changing how startups compete against much larger organizations. But despite all the technology shifts, he believes the entrepreneurial mindset itself remains remarkably unchanged. Founders still need resilience, conviction, adaptability, and the willingness to keep moving when nobody else believes in the vision yet.

A major theme throughout our conversation was how AI is reshaping entire industries faster than many business leaders realize. David explained how travel is moving away from the traditional “search, compare, book” model and toward conversational, agentic experiences powered by AI assistants. But rather than seeing this as a threat, he believes the biggest opportunity for founders lies in combining AI efficiency with deeply human experiences that technology alone cannot replicate.

For startup founders, there are valuable lessons here about positioning, timing, and differentiation. David argued that modern startups increasingly succeed by connecting fragmented ecosystems and reducing friction rather than inventing entirely new categories from scratch. In his view, the companies most likely to win in the AI economy will be those capable of simplifying complexity behind the scenes while creating highly personalized customer experiences at the front end.

We also explored the realities of balancing startup agility inside larger organizations. David spoke candidly about joining HBX Group as an entrepreneur entering a global corporate environment and the tensions that naturally emerge between operational consistency and rapid experimentation. His perspective on how founders and enterprises can work together without suffocating innovation offers some particularly useful insight for anyone navigating partnerships, acquisitions, or scale-up growth phases.

One of the strongest moments in the conversation came when David discussed failure, risk, and founder psychology. He believes too many investors and corporations publicly celebrate innovation while privately punishing failure. Real innovation, he argues, requires giving people room to experiment, fail fast, adapt quickly, and learn without fear. It is a mindset he compares to raising children: creating structure and support while still allowing enough freedom for creativity and growth.

David also shared a piece of advice many early-stage founders need to hear. Looking back, he believes startups often try to scale internationally far too early before securing a dominant position in their home market. The temptation to chase rapid expansion can distract founders from building operational strength, focus, and sustainable foundations.

This episode is packed with practical insight for founders, operators, investors, and anyone building businesses in rapidly evolving industries. From AI disruption and ecosystem thinking to founder resilience and scaling strategy, David offers a refreshingly honest perspective on what it really takes to build companies in an era defined by acceleration and constant change.

In this episode of Startup Builders and Backers, I sit down with Robin Saluoks, CEO and Co-Founder of eAgronom, to explore how a childhood connection to farming evolved into one of Europe’s fastest-growing climate-tech platforms. Robin shares how building a simple tool for his family farm at just 17 laid the foundation for a business now supporting more than 3,500 farms across 14 countries, helping them improve soil health, reduce emissions, and unlock new revenue streams through carbon credits.

We spend time unpacking why agriculture has remained one of the least digitized industries for so long, and what is finally changing. From AI and satellite monitoring to real-time data collection, Robin explains how technology is beginning to fit into the realities of farm life without adding friction. He also brings clarity to one of the toughest challenges in climate tech today, measuring soil carbon accurately, and why poor data can undermine even the most advanced models.

The conversation also explores the growing role of carbon markets and how farmers can participate without taking on unnecessary complexity or risk. Robin offers a practical view of how regenerative practices can improve profitability over time, why starting small matters, and how trust, local partnerships, and real-world results play a role in driving adoption.

As farming becomes more data-driven, we also touch on the implications for data ownership, control, and the shifting balance of power across the agricultural ecosystem. So as technology reshapes how food is produced and how carbon is managed, are we building systems that truly work for farmers, or simply adding another layer of complexity to an already demanding industry?

In this episode of Startup Builders and Backers, I sat down with Fran Loftus, Chief Experience Officer at EliseAI, to talk about a hiring philosophy that goes against the grain. At a time when so many companies are chasing the same technical talent, EliseAI is betting on people with founder DNA, generalists who can move fast, solve problems across functions, and take ownership from day one.

Fran brings a rare perspective to that conversation. She has lived both sides of it, first as a PropTech founder and now as an executive helping scale one of the most interesting vertical AI companies in the market. EliseAI supports operations for one in six U.S. apartments and is also automating workflows in healthcare, so this is not theory. It is a real-world look at how AI companies are being built, staffed, and scaled right now.

We talked about why generalist founders can often outperform narrow specialists in fast-moving AI environments, and how EliseAI structures teams more like micro-companies than traditional departments. Fran explained why engineers need to stay close to customers, why speed means very little if you are heading in the wrong direction, and how shorter feedback loops can lead to better products and better outcomes.

We also got into the bigger picture around leadership, org charts, and what happens as AI starts flattening layers of management. Fran shared why she believes strategy and execution are increasingly being owned by the same people, and why companies should stop fearing entrepreneurial employees who may one day leave to build something of their own. In her view, that mindset does not weaken a business, it makes it stronger.

If you are building, funding, or scaling an AI company, this conversation offers a refreshing perspective on what talent really looks like in 2026. It is about flexibility, customer obsession, and giving ambitious people the room to build inside your business before they build something of their own. What kind of team do you think will win in the AI era, and do you agree with Fran’s view that founder-minded talent is one of the biggest advantages a company can have? Share your thoughts.

We also explore how to balance urgency with long-term fit. Darren makes a strong case for clarity before speed. Know exactly what you are hiring for. Separate cultural alignment from core competency. And resist the temptation to drag out decisions when the fundamentals are not working. His perspective is grounded in experience, including lessons learned from hires that did not close deals or deliver results.

Another standout theme in this episode is partnership. Darren explains how Vader-Rey positions itself beyond transactional recruiting. From executive succession planning to long-term workforce strategy, he describes what it really means to be trusted by leadership teams from the warehouse floor to the boardroom. For founders who want to build companies that last, long-term thinking is worth listening to.

We also dig into modern workforce models. Darren discusses his approach to building distributed teams using virtual professionals, many based in the Philippines, and how treating them as valued team members rather than outsourced support changes performance and loyalty. There is also a practical conversation around using AI for contracts, process design, and operational efficiency, something many early-stage founders will find immediately actionable.

And because no Startup Builders episode is complete without a little personality, we also touch on the story behind the Vader-Rey name, pro wrestling, hot sauce, Rocky movie montages, and the creative balance required to build a business without losing yourself in the process.

If you are a first-time founder about to make your first three hires, or a startup leader wrestling with scale, culture, and delegation, this episode offers grounded advice from someone who has built the plane while flying it.

As always, I would love to hear your thoughts. What was the most expensive hiring mistake you have seen, or made, and what did it teach you?

In this episode of Startup Builders and Backers, I’m joined by Danielle Vogel, Assistant Director of the Veloric Center for Entrepreneurship at American University, where she works at the intersection of sustainability, entrepreneurship, and education. Danielle brings a rare perspective to the conversation, shaped by experience as a founder, an investor, and an educator supporting the next wave of builders long before they pitch a deck or incorporate a company.

Before stepping into academia, Danielle founded and operated Glen's Garden Market, a climate-motivated grocery store in Washington, DC, that became a launchpad for local food entrepreneurs. Through that venture, she helped support more than 90 local businesses, with a strong emphasis on women founders and founders of color. That lived experience informs how she now thinks about access, capital, and what it really takes to build something sustainable, both financially and socially.

We talk about her journey from founder to investor, including her direct investments, support for founders through the AccelerateHERdc grant program, and involvement with SoGal Ventures. Danielle shares how her approach to investing is shaped by values as much as returns, and why early belief, mentorship, and community can matter just as much as capital in the earliest stages of a startup’s life.

The conversation also dives into her work at the Veloric Center for Entrepreneurship, where she supports students across undergraduate and graduate programs, including sustainable entrepreneurship courses, incubators, competitions, and speaker series. We explore how young people are redefining what it means to be entrepreneurial today, and why the mindset itself is becoming just as important as founding a company.

This episode is not only about startups, funding, or accelerators. It is about expanding the definition of entrepreneurship, lowering the barriers to entry, and helping first-time builders take that initial step with clarity and confidence. As more young founders look for purpose alongside opportunity, how should we rethink what entrepreneurship really means, and who it is actually for?

Useful Links

• The Veloric Center for Entrepreneurship's LinkedIn:
• Follow Danielle Vogel on LinkedIn:
• Follow the Kogod School of Business on LinkedIn
• Kogod School of Business entrepreneurship website

Thanks to our sponsors, Alcor, for supporting the show.

In this episode of Startup Builders & Backers, I’m joined by Steven Woods, Founder of Stirlingshire Investments, for a conversation that goes far beyond balance sheets and buzzwords. Steve’s journey is anything but predictable. From leaving high school early to advising on Wall Street, earning credentials from Harvard and Oxford, and ultimately building a firm that questions how modern asset management should actually work, his path challenges many of the assumptions we still take for granted in finance.

We talked about why the traditional broker-dealer model feels increasingly out of step with today’s founders, operators, and investors. Steve shared how transparency, ethics, and genuinely personalized service can coexist with modern technology, and why large firms often struggle to deliver any of those at scale. Rather than chasing complexity, he argues that clarity and alignment are becoming the real differentiators in wealth management, especially for builders who want their capital to work in ways that reflect their values as well as their goals.

What I appreciated most was how practical this conversation became. Whether you are a seasoned investor, a startup founder thinking about long-term financial strategy, or simply finance-curious, Steve offers grounded advice shaped by lived experience rather than theory. We also touched on life outside the boardroom, from growing up in Kansas City to the contrast between Manhattan and Missouri, along with football, fishing, and why good barbecue still matters when building relationships.

If you are building something new or backing others who are, this episode offers a candid look at how personal reinvention and industry change often go hand in hand. As capital, technology, and trust continue to shift, what kind of financial partners will founders and investors really need in the next decade, and are we brave enough to move away from models that no longer serve us?

Useful Links

• Connect with Steven Woods
• Learn more about Stirlingshire Investments,

Thanks to our sponsors, Alcor, for supporting the show.

Emanuel reflects on how he built Stratodesk into a global player in Linux-based endpoint technology and the lessons learned along the way about scaling, product focus, and resilience. His advice for founders is refreshingly practical: stay obsessed with solving real problems, move fast when you fail, and never build technology for its own sake. We also talk about how IGEL’s acquisition of Stratodesk became a story of alignment rather than loss, showing how founders can successfully transition into leadership roles within larger organizations without losing their entrepreneurial drive.

We also dive into how his leadership philosophy has evolved. Emanuel explains how letting go of control after the acquisition gave him the freedom to focus on what matters most: innovation and people. He describes how creativity thrives when leaders balance listening with action, and how this mindset now shapes his work bridging customer insights with product development at IGEL. It’s a story that reminds any founder that scaling isn’t just about growth—it’s about adapting how you lead.

From AI-powered voice tools improving human connection to IGEL’s preventative security model, Emanuel illustrates how technology can both simplify and humanize work. His enthusiasm for building purposeful, people-first innovation remains undiminished after decades in tech. For startup founders, his journey is a reminder that reinvention never ends—it just takes new forms.

If you’re a founder looking for real-world startup lessons about scaling, acquisition, and staying inspired through change, this episode is for you. What do you think helps a founder thrive after their company is acquired? Share your thoughts and join the conversation.

Useful Links

• Connect with Emanuel Pirker on LinkedIn
  • Learn more about IGEL
  • Follow on LinkedIn, Twitter and YouTube

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Rather than giving up, Steve and his team made a bold pivot. They transformed LoopUp from a conferencing specialist into a global provider of cloud telephony for Microsoft Teams. Today, the company delivers enterprise voice services across 136 countries and proudly calls itself the world’s most multinational telco. Steve explains how this shift helps multinational businesses simplify operations by replacing dozens of regional telecom providers with a single unified system. With one contract, one support model, and one management portal, LoopUp allows companies to manage telephony the same way they already manage Teams globally.

We also talk about the wider transformation of the telecom industry. Legacy phone systems are being replaced by cloud infrastructure that integrates directly into the platforms people use every day. Steve shares what that change means for businesses seeking efficiency, scalability, and control.

Our conversation isn’t only about technology; it’s about leadership. Steve opens up about the lessons he’s learned through both highs and setbacks, from staying persistent during tough times to keeping honest communication flowing across the team. He also reflects on the strength of his long partnership with fellow co-founder Michael Hughes. For anyone building through uncertainty or leading through change, Steve’s journey is a powerful reminder that adaptability and openness are key to lasting success.

Paul shares lessons from his own entrepreneurial journey and explains how StartupOS helps founders refine their pitch decks, reach product-market fit, and assemble strong teams. We discuss how AI-powered tools can streamline investor readiness, surface strategic insights, and guide decision-making in ways that were previously out of reach for most startups.

The conversation also explores the importance of surrounding founders with the right ecosystem — one that blends mentorship, investor access, and collaborative networks — and how accelerators, enterprises, and even universities can plug into the StartupOS model. Paul offers his view on where the venture space is heading over the next year and what that means for early-stage founders looking to break through.

If you are building a startup and seeking practical, tech-driven ways to accelerate growth, this episode provides a blueprint for leveraging AI and community to drive success.

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Yael joins me from Israel in the middle of a war zone, where the urgency of her message becomes even more profound. Together, we explore what founders rarely talk about publicly: emotional fatigue, burnout, the silent strain on co-founder relationships, and the psychological toll of building a startup when your identity is wrapped up in its success or failure.

Drawing from her work with over 400 founders and leadership teams around the world, Yael breaks down:

• Why startup life often mimics survival mode and how to manage it
• The unconscious emotional drivers behind decision-making and leadership fatigue
• How dysfunctional co-founder dynamics quietly derail 65% of startups
• Why psychological contracts matter as much as shareholder agreements
• The overlooked link between childhood experience and startup behavior
• What founder burnout really looks like and how to recover from it holistically

As Yael puts it, “High-growth startups require high-growth founders.” This episode is an honest, moving reflection on what it really takes to survive and thrive as a startup leader, especially during times of extreme uncertainty.

We discuss the seismic shifts occurring across the tech landscape, particularly how AI is driving a new cycle of investment, innovation, and disruption. With $200 billion already invested in AI infrastructure and more to come, Rahul breaks down why this moment feels different from anything we've seen before—more accessible, more transformative, and, in many ways, more challenging.

We also talk about the slowdown in software growth, the short-term pressure on IT budgets, and how the most innovative companies are leveraging AI not just to survive, but to innovate faster and extend their competitive edge. Rahul also shared his views on the state of venture capital, the consolidation of VC firms, and why traditional players are regaining dominance.

For founders, this episode is packed with candid insights. Rahul pulls no punches when discussing what it takes to get funded today, what investors are looking for, and why financial discipline and real-world use cases are now non-negotiables. If you’re still clinging to a “raise at all costs” mindset, this is the wake-up call you didn’t know you needed.

🎧 In this conversation, we cover:

• How AI is reshaping the rules of the game for software and infrastructure
• Why 55,000 venture-backed companies is a sign of overinvestment, not progress
• What it now takes to go public and why the IPO bar is higher than ever
• Why the next generation of great startups will emerge from this tougher environment
• The impact of geopolitical tensions, rate shifts, and investor risk appetite on capital markets

If you're a founder, investor, or just trying to make sense of where tech is headed next, this one’s for you. You can find Rahul on LinkedIn, and as always, I’d love to hear your thoughts on the conversation.

We explore how authenticity, trust, and relentless focus on value have been key to Cask’s success. Jeff reflects on lessons from the dot-com era, the power of genuine client relationships, and why every implementation is more about outcomes than technology alone.

From the rise of AI-enhanced platforms to growing demand for local partnerships, we cover emerging trends reshaping the ServiceNow ecosystem. Jeff also discusses the increasing role of automation, the future of implementation services, and why the best consultants push back instead of simply checking boxes.

If you're building in the enterprise tech space, thinking about platform partnerships, or just want to understand what it takes to lead with heart in a technical world, this episode is for you.

Carsten explains how witnessing devastating wildfires and his own daughter’s climate activism pushed him to found Dryad Networks, a company deploying solar-powered sensors and mesh networks deep into forests to detect wildfires before they spread. We dive into what it takes to build rugged IoT devices for some of the world’s harshest, most remote environments, how Dryad trains edge AI to sniff out the gas signatures of a forest fire, and why satellite partnerships are vital to keeping the network online when traditional connectivity vanishes.

He also shares hard-earned insights on scaling hardware startups, building trust with governments and forestry organisations worldwide, and balancing climate impact goals with commercial reality.

This episode is a masterclass for anyone interested in climate tech, IoT innovation, or the grit required to turn a fresh idea into a global venture that could prevent millions of hectares from going up in smoke.

Tune in and get inspired by a founder turning sensors, AI and satellite links into tools for fighting climate change—one forest at a time.

Rethinking Book Success

The math is compelling. While most self-published books won't sell millions of copies, even reaching 1,000-5,000 targeted readers can transform a business. Look at any major conference - roughly half the speakers include "author" in their bios, often listing it before achievements that took far longer to accomplish. Why? Because books build authority at scale.

Forget the image of the solitary author in a cabin. Today's most successful business authors work with teams, use structured processes, and leverage technology. As Jorgensen notes, "There's such thing as writer's block, but there's no such thing as talker's block." Modern book creation is about converting expertise into written content, often through conversation and collaboration.

Technology as the Game-Changer

While AI won't replace human authors, it's revolutionizing the process of creating books. From organizing content to generating ideas and processing existing materials (like podcasts and talks), technology is making book creation more accessible. The key is understanding that "options are now free, and the judgment to choose the options remains human."

The Audio Advantage

Audiobooks now generate up to one-third of book royalties for some authors. However, the format decision extends beyond financial considerations. For consultants, speakers, and experts, narrating your audiobook creates a powerful trust bridge. When prospects hear your voice for hours before meeting you, you've already built significant credibility.

Strategic Over Mass Market

Success isn't about maximizing hardcover sales. It's about reaching the right readers. One Scribe Media author who helps financial planners transition their businesses found that readers who connected with his book became clients. Another, a lawyer, converted readers into high-value customers. The book became their most effective sales tool.

The publishing world has changed. Success no longer means hitting bestseller lists or selling hundreds of thousands of copies. Instead, it's about strategically positioning your expertise and reaching the readers who can become your best clients, partners, and advocates.

A well-executed book isn't just another product, it's a business transformation tool that works while you sleep.

Want to get started? Begin by defining your ideal reader and the change you want to create. The technology and teams are in place to support everything else.

In this episode of Startup Builders & Backers, I sit down with David Hirschfeld, founder of Tekyz Inc., to explore a different way of thinking about early-stage success. With more than 35 years in software and experience across over 90 startups, David shares what he has learned from both the wins and the missteps.

At the heart of this conversation is the Launch First Method, a framework David created to help founders validate demand before investing in development. It is a strategy designed to reduce time, cost, and the need for outside funding, while dramatically increasing the odds of building something people actually want.

We also dig into:

• How AI is reshaping the way software gets built
• Where automation helps and where it still falls short
• The key traits that define high-performing development teams
• How detailed artifacts like status reports and estimation tracking improve outcomes
• Why successful founders fall in love with the problem, not the product

David’s story spans decades of building, selling, and supporting software companies. He brings sharp insight and practical advice to anyone navigating the unpredictable path of early-stage growth.

If you're starting a company or backing one, this episode will help you ask better questions and make smarter decisions from day one.

Are you building what customers need or just hoping they show up? Let’s dig into that.

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.

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?

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.

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.

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.

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.

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.