Podcast
Inside the Network
Hosted by Inside the Network Pod · EN
Welcome to the inside track of cybersecurity entrepreneurship. We bring you the best founders, operators, and investors building the future of cybersecurity.
14episodes
Episodes
Newest firstAll episodes
Mark McClain: Winning as an incumbent at SailPoint in the age of AI
5d ago00:52:22Tap to summarizeThis episode of Inside the Network is unique because it is our very first show recorded live on the RSAC 2026 stage in front of security leaders, startup founders, and identity experts. For this episode, we had the privilege of sitting down with one of the most accomplished founders in cybersecurity, founder and CEO of SailPoint, Mark McClain.Cybersecurity is not an easy market to take a company public, and only the most successful founders have the opportunity to take a company public just once. Mark on the other hand has taken the same company public twice. He created the identity governance category from scratch, grew the company into a global identity security leader with more than $1 billion in ARR, over 3,000 employees, and customers across nearly half of the Fortune 500, took it public in 2017, private again with Thoma Bravo in a multi-billion-dollar transaction, and then back to the public markets in 2025.This episode explores one of the biggest questions in cybersecurity today: how do incumbents survive and win in the age of AI? Mark shares how large cybersecurity companies think about innovation, disruption, and adaptation in a world that’s changing faster than ever before. We discuss whether incumbents can turn scale, distribution, and customer trust into long-term advantages, or whether AI creates the perfect opening for a new generation of startups to challenge established leaders. Throughout the conversation, Mark reflects on the evolution of identity security from compliance tooling into one of the most critical security control planes in the enterprise. We dive into the rise of non-human and agentic identities, why traditional governance models are breaking under the speed of AI, and how companies like SailPoint are adapting to a world where identities can be ephemeral, autonomous, and operating at machine speed.We also talk about building startups in Austin versus Silicon Valley, lessons from taking the same company public twice, the realities of operating as both a public-company CEO and a founder, and what early-stage founders continue to underestimate about enterprise cybersecurity markets. In closing, Mark shares candid advice for founders building in cybersecurity today: where startups still have a real edge, what markets are ripe for disruption, and why listening to customers remains the ultimate competitive advantage.You can watch the full video recording of this conversation on-stage at the RSAC 2026 Conference here: Inside the Network Live: Winning as an Incumbent in the Age of AI.
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Christina Cacioppo: From Y Combinator to redefining trust in cybersecurity with Vanta
Apr 800:52:05Tap to summarizeIn this episode of Inside the Network, we sit down with Christina Cacioppo, Co-Founder and CEO of Vanta, the company that defined what is now known as trust management. What began as a scrappy effort to make SOC 2 less painful, has grown into one of the most important platforms in security and compliance. Christina’s path into cybersecurity was anything but conventional. She started her career in venture capital, and then worked as a product manager at Dropbox, where a frustrating encounter with compliance requirements revealed just how broken security audits were for fast-moving product teams. In our conversation, Christina shares how that painful Dropbox experience led to Vanta, why the company’s earliest product was essentially a spreadsheet rather than software, and how doing things manually helped her team find product-market fit faster. She talks about her process of ideation before landing on the idea, the decision to let word of mouth drive the business forward, what Vanta got out of joining Y Combinator, and why it intentionally avoided raising large rounds of venture capital in the early years. Christina offers a refreshingly honest look at leadership and scale. She discusses the hard lessons of hiring executives, the importance of defining company principles through real mistakes rather than corporate platitudes, and the challenge of moving upmarket without abandoning the startups that made Vanta successful in the first place. Christina explains how competition changed her perspective on storytelling, why founders cannot let others define their narrative, and how much of company-building is really about learning on real people in real time. This episode is full of hard-earned lessons on conviction, clarity, and the long game of building a multi-billion-dollar company.
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Sanjay Beri: Playing the long game and building Netskope into a public cybersecurity powerhouse
Mar 200:53:09Tap to summarizeIn this episode of Inside the Network, we sit down with Sanjay Beri, Founder and CEO of Netskope, a company that sits at the intersection of AI, data security, and global edge networking. Over thirteen years, Sanjay scaled Netskope to 4,000+ customers (including 30% of the Fortune 100), 3,000+ employees across 30 countries, and ultimately took the company public in September 2025 in one of the year’s standout cybersecurity IPOs.Sanjay’s journey is a masterclass in playing the long game. From growing up in Canada selling door-to-door with his mom, where he learned grit and resilience, to working at Microsoft during the early internet era, to becoming one of Juniper’s youngest VPs running a large business, Sanjay built the rare blend of product, go-to-market, and leadership muscle it takes to build at scale.We talk about the origins of Netskope, why it was never “just a CASB,” how Sanjay recruited world-class early engineers and built a high-trust culture, and what product-market fit looked like in the first chapter of the company. He also breaks down some of Netskope’s biggest bets, including building its own edge cloud instead of relying on public cloud networks, and launching AI Labs years before today’s GenAI wave.Whether you’re building a cyber startup, scaling into the enterprise, or studying what it takes to go from zero to IPO, this episode is packed with hard-earned lessons on conviction, the importance of building a winning culture, and endurance.
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Dino Boukouris & Sam Bronstein: How AI, identity, and cloud security defined 2025 and what 2026 holds for founders
Jan 1401:02:42Tap to summarizeIn this special year-end episode of Inside the Network, we’re joined by two of the most trusted strategic advisors in cybersecurity - Dino Boukouris, Managing Partner at Altitude Cyber, and Sam Bronstein, Partner at AXOM Partners. Between them, they’ve worked on billions of dollars in cybersecurity M&A, helped founders navigate exits to the world’s largest tech companies, and advised the CEOs behind some of the biggest public and private deals in the industry. In this episode, which also happens to be the 20th episode of Inside the Network, we break down what really happened across the cybersecurity landscape in 2025, from customer buying patterns and budget constraints to the $96B in M&A deal volume. Dino and Sam share insights on what’s driving consolidation, how buyers think about valuation and timing, and what defines a hot company in 2026 (hint: it’s not just growth). We talk about how mega-deals like Wiz and CyberArk are reshaping competitive dynamics in the industry, why SASE, identity, and security for AI have been the most active M&A themes, and what founders need to understand about building relationships with buyers long before they’re ready to exit. Sam and Dino explain that founders who achieve the best outcomes usually build relationships with potential acquirers over many years, and break down why many late-stage founders are likely to choose acquisition over IPO in the coming cycle.We close with tactical advice for founders heading into 2026: how to think about your board and investors, what metrics you’ll be judged on, and how to align your capital strategy with your long-term goals. And yes, we also talk about race cars, zero interest rates, outcome-based pricing, and what Palo Alto Networks might buy next.
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Dean Sysman: Betting on a boring problem and scaling Axonius past $100M ARR
Nov 2701:16:22Tap to summarizeIn this episode of Inside the Network, we sit down with Dean Sysman, co-founder and CEO of Axonius, one of the fastest-growing cybersecurity companies in the world. From struggling with his first startup to building a category-defining unicorn valued at $2.6 billion, Dean’s journey is a raw, insightful, and unfiltered look into what it really takes to build in security.Before founding Axonius, Dean co-founded Cymmetria, a Y Combinator-backed deception startup that despite all the efforts, didn’t end up leading to a successful outcome. That experience didn’t stop him; it made him more grounded, more strategic, and more deliberate. Dean 2.0 didn’t enter a hot market. Instead, he went after a boring but foundational problem everyone had, but no one wanted to touch - cyber asset visibility. In just under five years, Axonius surpassed $100M in ARR and raised over $600 million to fund growth and acquisitions.Dean’s path has been unconventional from the start. He taught himself to code at 12, won an international robotics competition at 15, and led a team in Unit 8200 by 21. In the military, he learned responsibility the hard way: “If you fail, no one else is coming to help.” That mindset became the core of his entrepreneurial approach. In this conversation, Dean opens up about what most people get wrong about Unit 8200, why the army’s bureaucracy actually helped him understand enterprise sales, and how he turned a failed venture into the insight that led to Axonius.We talk about the early days of building Axonius, the decision to go deep into a “Toyota Camry” problem, and how he convinced two close friends from Unit 8200 to bet on a boring idea that became a unicorn. Dean breaks down the evolution of cyber asset management, what it took to define a new category, and why timing and value communication matter more than tech novelty. He also shares lessons from Axonius’ first acquisition, Cynerio, and what founders need to understand about getting M&A right: culture, timing, and strategic alignment matter far more than valuation spreadsheets.
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Tomer Weingarten: From cyber outsider to building SentinelOne into a $1B ARR category leader
Oct 2101:11:08Tap to summarizeIn this episode of Inside the Network, we sit down with Tomer Weingarten, Co-Founder and CEO of SentinelOne, one of the fastest-growing cybersecurity companies. From writing code and designing the company’s first UI himself, to taking SentinelOne public and crossing $1 billion ARR, Tomer’s journey is a rare combination of technical excellence, grit, and long-term conviction.Tomer didn’t grow up surrounded by startup founders or Silicon Valley mentors. He was raised in a small Israeli town with few resources and found computers as a creative escape. He met his SentinelOne co-founder, Almog Cohen, in second grade, began hacking games as a teenager, and exited his first startup at just 24 making millions of dollars. Then, in an unusual move, he spent all the money to reset, stay grounded and hungry to build something big. That big ambition would become SentinelOne.When SentinelOne launched in 2013, most endpoint vendors were still focusing on signature-based antivirus, and the idea of autonomous, behavior-based prevention powered by AI sounded like science fiction. Tomer wanted to reimagine cyber defense from the ground up. The company’s early traction didn’t come easy, and it took several years of heads-down engineering effort to get to the point when the company signed its first customer and investors stopped being skeptical. Tomer believed the problem wasn’t being solved deeply enough, and he stayed patient while the market caught up.Tomer shares how he navigated the “wartime CEO” moments like fighting off rivals with 10 times the budget, managing internal politics, and surviving near-death moments during fundraising. He reflects on how leadership styles evolve under pressure, and how the discipline of writing down decisions helped him become a better CEO. He also breaks down how founders confuse early ARR with true product-market fit, and why most security companies today are in his opinion workflow wrappers, not tech companies.We also explore Tomer’s views on the LLM hype cycle and why he believes most of the AI noise in cybersecurity today is more marketing than the actual deep tech. Tomer believes that true moat lies in foundational models trained on real, curated telemetry, and in solving hard tech problems, not just ChatGPT integration. This episode is a deeply personal look at what it takes to build enduring companies in cybersecurity. This is one of our most honest, unfiltered founder conversations, and if you care about the art of company-building, you won’t want to miss it.
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Sumit Dhawan: Leading Proofpoint’s AI evolution and building toward $5B in ARR
Sep 1500:53:58Tap to summarizeIn this episode of Inside the Network, we sit down with Sumit Dhawan, CEO of Proofpoint, one of the largest private cybersecurity companies in the world. With over $2 billion in ARR, Proofpoint protects 85 of the Fortune 100 and is on a bold path toward $5 billion in revenue by 2030.Sumit’s journey is a masterclass in modern leadership. Having graduated with degrees in engineering and business from IIT Roorkee, the University of Minnesota, and the University of Florida, Sumit led major business lines at Citrix and VMware, including overseeing VMware’s $70 billion divestiture to Broadcom, before making the leap to cybersecurity. In 2023, he joined Proofpoint as CEO and began executing an ambitious strategy: consolidate the sprawl of human-centric security, go deep instead of broad, and prepare the company for its next chapter of growth.In our conversation, Sumit shares why he believes empathy is the most underrated CEO trait, how acting like a founder, even inside large enterprises, shaped his leadership, and what it means to have “Apple Watch governance” under Thoma Bravo. He explains how Proofpoint has evolved from email security leader to a broader platform for human and data protection, including its acquisitions of Tessian (AI-native email protection), Hornetsecurity (MSP-focused email security), and Normalyze (DSPM).Sumit also pulls back the curtain on the AI threat landscape, including how prompt injection attacks are already targeting copilots and agents, why AI is both supercharging attackers and empowering defenders, and how Proofpoint built intent-based detection models to defend against sophisticated zero-link phishing. Finally, he lays out three categories of viable cybersecurity startups today: gap-fillers, AI defenders, and category disruptors, and why the last two are more likely to be successful.Whether you’re scaling a cyber startup, selling into the enterprise, or navigating PE-backed growth, this episode is full of hard-earned wisdom from a leader who’s operated at every level of the stack.
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Jay Chaudhry: Betting on yourself and building a $40B+ Zero Trust giant in Zscaler
Aug 2600:53:45Tap to summarizeIn this episode of Inside the Network, we sit down with Jay Chaudhry, founder and CEO of Zscaler, one of the most valuable cybersecurity companies in the world with a market cap of over $40 billion and $3 billion in ARR.Jay’s journey is unlike any other. Raised in a remote Indian village with no electricity, no running water, and a two-and-a-half-mile walk to school, he went on to build five companies and pioneer the modern Zero Trust cloud security model. Zscaler, his most iconic company, was launched in 2007 with $50 million of his own capital and no VC investment - a bold bet in the middle of a market downturn, at a time when few believed enterprise security could move to the cloud.This episode is packed with powerful lessons from a founder who’s played the long game. Jay talks about the mindset he carried from his early years farming with oxen, how working alongside his wife Jyoti gave him unmatched focus and alignment, and why startups should be “a foot wide and 20 feet deep.” He explains how Zscaler rewrote not just the playbook for go-to-market in security, but also the TCP/IP stack, and the early challenges of selling Zero Trust well before the term even existed. He also shares his wisdom on why most founders pivot too late when their sales motion fails. Jay provides his view of the future of cybersecurity and the Internet itself, from why the private corporate network is dying to why firewalls will eventually go the way of mainframes.Throughout it all, Jay shares a rare combination of conviction, humility, and self-discipline. Whether you’re a first-time founder or running a $10 billion company, this is an absolute masterclass in how to build enduring companies and stay grounded in the process.
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Michelle Zatlyn: Scaling Cloudflare to a $70B giant and building a better Internet
Jul 3101:01:48Tap to summarizeIn this episode of Inside the Network, we sit down with Michelle Zatlyn, Co-founder and President of Cloudflare, one of the most iconic Internet infrastructure companies in the world. From its launch during the depths of the 2009 financial crisis to today’s $70 billion market cap and 5 million+ customers, Cloudflare has become a cornerstone of global Internet security and performance.Michelle’s journey is remarkable. Raised in a small farming town in Saskatchewan, Canada, she left behind plans to become a doctor and instead teamed up with Matthew Prince and Lee Holloway to tackle an audacious question: “How can we build a better Internet?” Fifteen years later, Cloudflare is the third most valuable cybersecurity company in the world, protecting millions of businesses and powering the modern web.In our conversation, Michelle shares what it really took to build Cloudflare, why grit mattered more than expertise in the early days, how deep trust among co-founders carried them through the hardest moments, and why “just ship it” became a guiding principle that fueled rapid growth. She also reflects on how Cloudflare has avoided the innovator’s dilemma, continuing to reinvent itself even as a public company, and how AI is reshaping the web, including why she believes we need a new business model to create the right incentives for content creators in the age of large-scale AI crawlers.
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Joe Levy: Scaling Sophos to $1B+ revenue and defending the 350M overlooked businesses
Jun 2801:05:03Tap to summarizeIn this episode of Inside the Network, we sit down with Joe Levy, CEO of Sophos, a 40-year-old cybersecurity company that has quietly become one of the most important global players, serving over 600,000 organizations and generating over $1 billion in revenue. Throughout his career, Joe has operated with a founder's mindset: thinking in bets, building great teams, spotting technical and market inflection points, and executing with long-term discipline. A great example is Sophos’ recent $800+ million acquisition of Dell Secureworks, adding over 1,000 new team members and significantly expanding Sophos’ managed detection and response and extended detection and response (MDR/XDR) capabilities. Today’s session is an exciting masterclass on how a technically astute CEO navigates demanding customers, engages positively with Private Equity giants like Thoma Bravo, and partners with MSPs globally, while building a culture of "vulnerability-based trust”. One of the most insightful statistics Joe and his team at Sophos have highlighted is that while there are over 350 million businesses worldwide, fewer than 1 in 10,000 have a CISO. This episode is packed with practical lessons on founder transitions, managing through personal health crises, and building resilient security organizations. For any cybersecurity founder thinking about the long game, Joe’s story is one you’ll want to hear.As mentioned in the episode, Joe shared a curated list of books he’s been collecting over the years for his daughter, a shelf he calls “my daughter’s bookshelf.” These aren’t just bedtime stories; they’re books that have shaped Joe’s thinking about the world, passed along with personal inscriptions to provide context and reflection. Some were even introduced by his wife, Tracie, and read together as a family, like the James Herriot series, which took nearly a year to complete and left a lasting impression. This isn’t meant to be a definitive reading list - many classics, business books, and philosophical staples are intentionally left out. But it offers a deeply personal window into the stories that have mattered most to Joe as a parent, leader, and lifelong learner. He also shared a second resource: a living document of quotes, mental models, and hard-won career lessons, many of which have shaped his leadership journey and are referenced throughout the episode. You can explore both below."Joe's daughter’s bookshelf" Quotes & career notes
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