Inside the Network

Inside the Network Pod
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Welcome to the inside track of cybersecurity entrepreneurship. We bring you the best founders, operators, and investors building the future of cybersecurity.

  1. Dean Sysman: Betting on a boring problem and scaling Axonius past $100M ARR

    NOV 27

    Dean Sysman: Betting on a boring problem and scaling Axonius past $100M ARR

    In 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.

    1h 16m
  2. Tomer Weingarten: From cyber outsider to building SentinelOne into a $1B ARR category leader

    OCT 21

    Tomer Weingarten: From cyber outsider to building SentinelOne into a $1B ARR category leader

    In 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.

    1h 11m
  3. Sumit Dhawan: Leading Proofpoint’s AI evolution and building toward $5B in ARR

    SEP 15

    Sumit Dhawan: Leading Proofpoint’s AI evolution and building toward $5B in ARR

    In 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.

    54 min
  4. Jay Chaudhry: Betting on yourself and building a $40B+ Zero Trust giant in Zscaler

    AUG 26

    Jay Chaudhry: Betting on yourself and building a $40B+ Zero Trust giant in Zscaler

    In 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.

    54 min
  5. Michelle Zatlyn: Scaling Cloudflare to a $70B giant and building a better Internet

    JUL 31

    Michelle Zatlyn: Scaling Cloudflare to a $70B giant and building a better Internet

    In 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.

    1h 2m
  6. Joe Levy: Scaling Sophos to $1B+ revenue and defending the 350M overlooked businesses

    JUN 28

    Joe Levy: Scaling Sophos to $1B+ revenue and defending the 350M overlooked businesses

    In 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

    1h 5m
  7. Andy Cao and Hugh Thompson: Inside RSAC 2025’s biggest moments and boldest ideas

    MAY 21

    Andy Cao and Hugh Thompson: Inside RSAC 2025’s biggest moments and boldest ideas

    In this RSAC special episode of Inside the Network, we sit down not with one, but two remarkable guests from the center of the cybersecurity world. First, we’re joined by Andy Cao, COO of ProjectDiscovery, a company focused on open-source vulnerability management tools, which won the "Most Innovative Startup" award at the RSA Conference 2025 Innovation Sandbox. Andy shares how ProjectDiscovery is reimagining vulnerability management in an AI-driven world, what set their pitch apart in the Innovation Sandbox, and how their attacker-first mindset is reshaping how security teams discover and fix real-world exposures. With over 1 million users and thousands of Nuclei templates, ProjectDiscovery is aiming to make vulnerability detection radically faster, smarter, and more accessible. Then, we shift gears to talk with Dr. Hugh Thompson, Executive Chairman and Program Committee Chair of RSAC. A world-renowned security expert and longtime steward of the conference, Hugh takes us behind the curtain of what it takes to run the world’s largest cybersecurity gathering, including the bold moves that shaped this year’s Innovation Sandbox, the evolution of the RSAC brand, and the future of security thought leadership in the age of AI. And most intriguingly, Hugh gives us an exclusive answer to the question everyone’s been asking - is RSAC 2026 moving to Las Vegas? To close, Mahendra, Sid, and Ross share their favorite moments from the show floor - the trends that caught their attention, the buzz from founders and investors, and yes, even a surprise guest spotted at the expo (spoiler: it’s not a unicorn, but maybe the GOAT?). Whether you made it to RSAC this year or followed from afar, this episode brings you fresh insights from both the main stage and the show floor.

    53 min
  8. Dug Song: Values over valuation—reflections on building Duo Security and leading with purpose

    APR 6

    Dug Song: Values over valuation—reflections on building Duo Security and leading with purpose

    In this episode of Inside the Network, we sit down with Dug Song, the legendary co-founder and former CEO of Duo Security. Dug's journey is nothing short of iconic—he turned a side project into a cybersecurity powerhouse with over 50,000 customers and a $2.35 billion exit to Cisco. In a world obsessed with unicorn status and funding hype, Dug stands out as a founder who stayed grounded in values, culture, and customer empathy. We explore Dug’s early years—from doing data entry in his father’s liquor store in West Baltimore to cutting his teeth at Arbor Networks, leaving security, and coming back to change how security is delivered. Dug was also part of the hacker collective w00w00, alongside future tech luminaries like Jan Koum (WhatsApp) and Shawn Fanning (Napster), where he honed the ethos of solving hard problems and building in community. These experiences laid the foundation for Duo, which Dug and co-founder Jon Oberheide started not with a grand business plan but a desire to democratize security and make strong authentication simple and usable for all organizations—not just the Fortune 500. This conversation is packed with actionable lessons for founders: how to build a billion-dollar business with capital efficiency and discipline; how to prioritize user experience in security, not just infrastructure; and how to lead with integrity and build a “learning organization” that continuously improves across every function—engineering, sales, marketing, and customer success. Dug also gives an inside look at the decision to sell Duo to Cisco versus going public and what that choice meant for the company, team, and customers. We then dive into Dug’s post-Duo chapter, where he and his wife Linh are reshaping philanthropy and backing the next generation of founders in Michigan, Detroit, and beyond. From punk rock to planetary-scale startups, Dug brings a rare mix of grit, humility, and wisdom, making this episode a must-listen for any entrepreneur.

    1h 26m
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About

Welcome to the inside track of cybersecurity entrepreneurship. We bring you the best founders, operators, and investors building the future of cybersecurity.

Information

  • Creator
    Inside the Network Pod
  • Years Active
    2024 - 2025
  • Episodes
    19
  • Rating
    Clean
  • Copyright
    © Inside the Network Pod
  • Show Website
    Inside the Network

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