Inside the Network

Our guest in this episode is Mike Fey, co-founder and CEO of Island, one of the fastest-growing cybersecurity companies. Founded just five years ago, Island has raised over $700 million in funding, crossed $5 billion valuation, and helped create an entirely new category: the Enterprise Browser.Mike has scaled massive cybersecurity businesses. Over the course of his career, he has served as CTO of Intel Security and President of both Blue Coat and Symantec. Mike played a key role in some of the largest transactions in cybersecurity history, including Intel's $7.7 billion acquisition of McAfee, Symantec's $4.7 billion acquisition of Blue Coat, and Broadcom's $10.7 billion acquisition of Symantec's enterprise business.After decades of leading some of the industry's largest security companies, Mike could have easily become an investor, advisor, or board member. Instead, he decided to start over from scratch. Together with co-founder Dan Amiga, he set out to challenge one of the most entrenched pieces of enterprise software: the browser. At first glance, building a browser company sounded like a terrible startup idea: enterprises already had Chrome, Edge, Safari, and countless security products protecting them. Yet Mike and the Island team believed that the browser was evolving into the primary workspace for modern employees and that whoever controlled the browser could fundamentally rethink security, productivity, and the future of work.On Inside the Network, Mike shares the story behind Island's creation, why he initially rejected the idea before becoming convinced it could become a generational company, and how the team navigated the challenge of convincing enterprises to replace one of the most widely used pieces of software in the world.We discuss category creation, the Innovator's Dilemma, building go-to-market organizations from scratch, fundraising strategy, and the lessons Mike learned from scaling businesses through more than $20 billion worth of acquisitions. He explains why founders often underestimate sales and go-to-market execution, how startups can use incumbents' strengths against them, and why market timing matters more than many entrepreneurs realize. We also dive into the impact of AI on enterprise software and cybersecurity, how AI is reshaping the role of the browser, and why Mike believes the browser will become the front door through which enterprises adopt and operationalize AI.

In 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.

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.

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.

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

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.

Shlomo Kramer, CEO and co-founder of Cato Networks is a rare bird in the cybersecurity industry, having built three unicorns in his career. For many in the cybersecurity industry, Shlomo needs no introduction. One of the early pioneers in Israel’s cybersecurity startup ecosystem, what makes Shlomo remarkable is his ability to repeatedly build category-defining companies. He first co-founded Check Point, which pioneered the firewall category and today commands a $20 billion market cap. Then, seeing the shift to the cloud, he launched Imperva, focusing on web application security (WAF). That was his second IPO. Now with Cato Networks, he's created an entirely new category called SASE – Secure Access Service Edge – and Cato has already reached over $200 million in annual recurring revenue.But Shlomo isn't just a builder – he's also a remarkably successful investor with an eye for transformative companies. His portfolio includes Trusteer, which IBM acquired for $1 billion, and Palo Alto Networks, in which he wrote the first angel check and sat on its board - a company now valued well over $100 billion dollars.In this episode, we get inside the mind of the only entrepreneur we know who's on track to potentially take his third cybersecurity company public. Many founders are satisfied with one IPO, some rarely go to two and Shlomo is on track for his third IPO - a hat trick if he pulls it off. In the cybersecurity hall of fame, very few could equal what Shlomo has accomplished.We discuss building cybersecurity companies, the evolution of the security market over the past three decades, why founders should focus on their customers instead of competitors, how building startups has changed from when Shlomo started Check Point, and many other aspects of the founder's journey.

In this episode, we sit down with Kumar Saurabh, CEO and co-founder of AirMDR, which provides a new approach to managed detection and response with an AI-powered virtual security analyst. A serial entrepreneur, Kumar has been at it for two decades. Before AirMDR, he co-founded Sumo Logic, the first cloud-based SIEM, and LogicHub, one of the pioneers of SOAR.Kumar’s journey as an immigrant founder offers a unique perspective on why immigrants often succeed as entrepreneurs and how institutions like the Indian Institutes of Technology (IIT) have produced some of the world’s most successful tech leaders. Drawing on his experience, Kumar explores why large companies struggle to innovate, the competitive edge startups hold over established players, and how founders can identify opportunities in markets that may appear crowded. He also shares actionable insights for founders on hiring top talent from leading companies and scaling a startup with the right team. Having collaborated with premier venture capital firms like Greylock, Sutter Hill, Sequoia, and Accel, Kumar provides invaluable advice on selecting the right VC partners, what to look for, and common mistakes to avoid. Kumar’s story is a testament to resilience, innovation, and the power of identifying opportunities in enterprise tech, making him a leading voice in the startup ecosystem.

In this episode, we sit down with Slavik Markovich, CEO and co-founder of Descope, a low-code/no-code Customer Identity Access Management (CIAM) platform. A serial entrepreneur, Slavik has been at it for two decades and over this time built three companies.Before Descope, he was co-founder and CEO at Demisto, a leader in the SOAR industry that was acquired by Palo Alto Networks for $560 million. Before co-founding Demisto, Slavik was VP & CTO of database technologies at McAfee (Intel Security). He joined McAfee via the acquisition of Sentrigo, a database security startup, where he was a co-founder and CTO. Slavik also served in the Israel Defense Forces (IDF) for 5 years as a team leader. He graduated with a degree in computer science from The Technion (Israel’s MIT).We speak with Slavik about his childhood and what got him hooked on cybersecurity. We cover Slavik’s learnings on how to identify early product-market fit and define a category like what he did with SOAR (Security Orchestration, Automation, and Response). We discuss the art of negotiating a VC fundraise and M&A exit. And of course, we touch on how Slavik’s love for good coffee has played a key part in building friendships including with one of his co-founders Rishi Bhargava.

Our guest in this episode is Jon Gelsey. Jon was the first CEO of Auth0, a leading identity-as-a-service platform, which grew from 5 to 300 employees during his four years at the helm. Auth0 was acquired by Okta in February 2021 for $6.5B. After Auth0, Jon served as CEO of Xnor, a computer vision and machine learning spinoff of the Allen Institute. The company was acquired by Apple for ~$200M in January 2020. When Auth0 first started in 2013, there were already several authentication vendors in the market. Okta, ForgeRock, and OneLogin had all built considerable scale by the time Auth0 launched its product. Not only did Jon and the team build a successful company in a very crowded space, but they also did it their way. While all of Auth0’s competitors were running a top-down GTM motion, Jon made a critical decision to adopt a bottom-up, product-led growth (PLG) strategy. Instead of relying on traditional marketing tactics for demand generation, Auth0 built an extensive content rollout plan to help drive inbound interest in the product. To date, Auth0 is the only PLG company in cybersecurity to achieve a multi-billion dollar exit. On Inside the Network, Jon talks about building go-to-market strategies, identifying the right buyer personas, and establishing success metrics for customer acquisition. In addition to his experience as a serial entrepreneur, Jon worked on the M&A and strategy team at Microsoft from 2007 to 2014 where he led several acquisitions for the company. Jon shares the tips and tricks founders need to know to plan, negotiate, and successfully close acquisitions with potential buyers.

Few cybersecurity companies have been able to bootstrap their way to success – Tenable stands above the rest in this category. The company raised its first round of funding after 10 years of operations. It had $90M of revenue at the time. In the venture world, “Tenable was the best cybersecurity business that nobody had ever heard of.” Today, it is the leading cyber exposure and vulnerability management company with $800M in revenue and over 44,000 customers globally.In our second episode of ‘Inside the Network’ we sit down with Ron Gula, co-founder and former CEO of Tenable. We learn about his early beginnings and love for fighter jets and UFOs. We dive into his three successful startup journeys, including his most recent run building Tenable over 14 years. And we talk about lessons learned from his investing career at Gula Tech Adventures with over $100M invested in 50+ startups.After their successful entrepreneurial journey, Ron and his wife Cyndi’s work has continued with Gula Tech Foundation, working to make the cybersecurity sector more diverse and inclusive. Finally, we touch on Ron’s new-found passion as a YouTube influencer – the Joe Rogan of cybersecurity has now garnered over 150K subscribers!