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"Fireside MSP" is a warm, engaging podcast brought to you by the Managed Service experts at XenTegra, where technology meets conversation around the virtual fireside. Each episode dives deep into the world of managed services, exploring the latest trends, solutions, and innovations that are shaping the future of technology. Hosted by seasoned professionals from XenTegra and featuring occasional guest appearances from our industry partners, "Fireside MSP" aims to demystify the complex world o ...
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Think Big, Buy Small

Harvard Business School

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Are you looking for an alternative to a career path at a big firm? Does founding your own startup seem too risky? There's another compelling path open to you: acquiring a small business and running it as CEO. Co-hosted by Harvard Business School Professors Richard Ruback and Royce Yudkoff, the show is an extension of their courses on small firms, including Entrepreneurship Through Acquisition, which has been taken by thousands of MBA students, and their highly-regarded book, HBR Guide To Buy ...
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In this episode of Talking Cloud, Yair Herling and I discuss the evolving landscape of cybersecurity, focusing on exposure management and the importance of remediation strategies. We explore the challenges of cyber war, the balance between fear and hope in security, and the role of AI in enhancing cybersecurity measures. The conversation emphasizes…
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In this episode of Talking Cloud, my guest is Amy Chaney, a transformation artist with extensive experience in technology and risk control. We discuss the evolving landscape of cloud technology, the impact of AI on workforce dynamics, and the importance of identity management in cybersecurity. Amy shares insights on navigating organizational change…
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In this episode of Talking Cloud, I catch up with Boaz Barzel, the field CTO at Ox Security. We discuss the complexities of application security, the evolution of security practices in the age of AI, and the challenges organizations face with alert fatigue. We explore the importance of integrating security into the development process and the role …
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In this episode I sit down with Clay Sharman, founder of Krateo AI, discussing the challenges of understanding consumer intent in e-commerce. We explore the high percentage of anonymous web traffic and how Krateo AI aims to identify potential customers through data analysis. Clay shares insights into the creative process behind Krateo AI, the value…
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In this episode, I speak with Oded Vanunu, Check Point's Chief Technologist. We delve into the evolving landscape of cybersecurity, discussing the shift from traditional warfare to cyber warfare, the rise of organized cybercrime, and the role of AI and blockchain in enhancing security measures. We explore the implications of these changes for digit…
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In this episode of Talking Cloud, I sit down with Daniel Wiley to discuss the evolution of cybersecurity, the founding of LogSeam, and the challenges faced in security operations. Dan shares his extensive experience in the field, including his role in building incident response teams at Checkpoint and the innovative approaches LogSeam is taking to …
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In this episode of Talking Cloud, I speak with Adi Golan, Vice President of Skyhawk Security, discussing the evolution of cloud security, the challenges faced in the industry, and the innovative solutions being developed to enhance security measures. We explore the role of AI and machine learning in cybersecurity, the complexities of CNAPP, and the…
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In this engaging conversation, Vikram Phatak and I explore the rapid evolution of AI and cloud technology, discussing its profound impact on daily life and the cybersecurity industry. We delve into the significance of trust in technology leadership and the challenges of maintaining integrity in a market filled with hype and misinformation. Our disc…
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In this episode of Talking Cloud, I engage with Craig Calder to explore the evolving landscape of AI and its implications for business and society. We discuss the importance of curiosity in tech, the shift towards outcome-based pricing models, and the challenges of implementing AI in organizations. The conversation also touches on the future of ide…
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In this episode of Talking Cloud, I interview Kirsten Bay, CEO and co-founder of Cysurance, discussing her journey from supply chain operations to the world of cybersecurity and insurance. We explore the evolution of data valuation, the complexities of cyber insurance, and the importance of understanding risk management in today's digital landscape…
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In this episode of Talking Cloud, Grant Asplund interviews Paul Chang, CEO of Brand Engagement Network (BEN), discussing the evolution of AI technologies, particularly large language models, and their applications in business. Paul shares insights from his extensive experience at IBM and how BEN is leveraging AI to create tailored solutions for var…
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At the end of each episode, Rick and Royce ask listeners to reach out with any questions they may have related to entrepreneurship through acquisition. In response, we’ve heard from people at all stages of their entrepreneurship through acquisition journeys, along with other stakeholders in search. Now, in the final episode of Season Two, our hosts…
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Episode #74 features a great discussion with Steve Winterfeld, Advisor, and Fractional CISO with Cyber Vigilance Advice (CVA) LLC. Steve is passionate about cybersecurity. He served as CISO for Nordstrom Bank, Director of Cybersecurity for Nordstrom, and Director of Incident Response and Threat Intelligence at Charles Schwab. Steve also published a…
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A few years ago, Logan Leslie began his search with the goal of rolling up smaller, same-industry enterprises under the umbrella of one company. Fast forward to today and Logan is CEO of Main Street Auto, which is the parent company to over ninety auto repair shops around the country. In this engaging conversation, Logan shares why he believes the …
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In the last three years, Adriana Garcia Ceja graduated from Harvard Business School, became a mother and, after a funded search, acquired an aging life care management business called ElderTree. Many would-be CEOs set out on their searches primarily wanting to experience the joys of operating a small business, while being more agnostic about what t…
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This week, my guest is Matt Stamper, CEO | CISO & Executive Advisor. Matt is a multi-time CISO with extensive experience in cybersecurity, information security, cloud security, IT audit, risk management, privacy, AI security, and governance. Matt is a former research director and security analyst at Gartner (NYSE: IT) and has extensive experience i…
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Kent Weaver was an early participant in the world of search, completing a self-funded search that led to his acquisition of a healthcare company in 2002 and then, four years later, putting on his investor hat to make his first investment in search. Today, he’s one of the most experienced and highly regarded funding partners in the space, having inv…
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Connor McCarthy and Caroline Matthews are not only a married couple and new parents, but they’re also funded searchers turned co-CEOs at Canyonlands Camps. The outdoor recreation industry is little explored in the world of search and their ETA journey is also distinct in that, through the acquisition of summer camps and travel programs, they’ve tak…
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I was so excited to post this episode, I forgot to write an introduction!! In this program I sit down with Paul Nguyen, Co-Founder and Co-CEO at Permiso. Paul has a long history of success in the cybersecurity. He's an invovator and entrepreneur and a fantastic guest! I hope you enjoy it!!!By talkingcloud
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William Young became CEO of Aerowave Technologies in January of 2021. While he has no regrets about his pursuit of the ETA path, his journey to the company’s helm was a difficult one. His story is distinct in that he started out in a partnered, brokered search but ended up as a solo searcher, focusing on proprietary outreach in Dallas-Fort Worth an…
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Sam Rosati is a former searcher turned active equity investor in self-funded searches and, given his experiences, an important focus of this conversation is on the evolution of the self-funded market. It used to be the case that self-funded searchers had to create their investor base from scratch, out of pure networking. Now, however, a path is eme…
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Betsy Harbison, CEO at Softrip, successfully completed a funded search in 2021. Her story, however, is rather unique in that the business she acquired is a remote, vertical software company that was also a carve out, meaning that a crucial part of Betsy’s journey involved the daunting task of untangling Softrip from its parent company. In this epis…
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I first met my episode 68 guest in 2002. I recently completed the reacquisition of MetaInfo from Check Point. While Check Point retained 20%, my employees and I owned 80%. Chris, the CEO of Nominum, reached out to me to discuss a possible merger between our companies. The short story is we never merged. Chris led Nominum until they were acquired by…
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In May of 2024, after a self-funded search, Brian Seeling became CEO of PGM Service, a Florida-based company that focuses on maintenance, service, and repair of commercial food equipment. His journey to become an acquisition entrepreneur is distinct in that he first worked as a software engineer, was then involved in startup life for a number of ye…
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Not only is Zach Duprey a highly experienced commercial lender to those seeking to acquire a small business but, in helping to create a national market for these loans, he has been instrumental in dramatically changing the landscape of small business lending, revolutionizing the market for search. In this episode, Zach describes the “three legs of …
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In this episode, I sit with the Head of Cloud Security Engineering at Check Point Software. Brian McHenry joined Check Point after over a decade and a half at F5 focused on WAF. Brian has been a practitioner, a Sales Engineer, and a Product Manager. Hear why Brian left F5 and joined Check Point and what he started in NY in 2016.…
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After a brokered search, Jenn Braus became CEO at Systems Design West, a company that provides customized ambulance billing, emergency medical services billing, and accounting services to fire and rescue organizations, and one that Rick and Royce believe is “the perfect recurring revenue business.” In this episode, we learn about the beauty of recu…
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In May of 2021, after a self-funded search, Nick Vandam became CEO of MCI, a telecommunications infrastructure company based in St. Paul, Minnesota. In this episode, he shares his distinct journey, including his days at West Point; competing in triathlons on the U.S. National Team; deployment in Afghanistan; work experience at a large financial ser…
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Starting in early February, we’ll begin releasing new episodes of Think Big, Buy Small, season two. Rick and Royce are looking forward to sharing some fantastic conversations with you! Ahead of these new releases, however, we've built a bridge, of sorts, between the two seasons by checking in with season one guest, Geoff Duckworth, who was featured…
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Episode 65 features Marina Segal, a friend, former colleague, and now co-founder and CEO of her VC-backed start-up, Tamnoon (www.tamnoon.io). I first met and worked with Marina Segal at Dome9 and, subsequently, Check Point Software. Marina is a shrewd and highly experienced executive with a strong background in Security Governance, Risk, and Compli…
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Happy 2025! In this two-part episode, my guest is the founder of North Labs, Collin Graves. We discuss a variety of topics, including, of all things, the similarities between Higher Education and manufacturing! I'll never think of a 'bow-tie' in the same way again! Collin was an early pioneer in cloud computing and was one of the very first certifi…
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Happy 2025! In this two-part episode, my guest is the founder of North Labs, Collin Graves. We discuss a variety of topics, including, of all things, the similarities between Higher Education and manufacturing! I'll never think of a 'bow-tie' in the same way again! Collin was an early pioneer in cloud computing and was one of the very first certifi…
  continue reading
 
In another two-part episode, I sit down with a long-time cybersecurity professional and personal friend, Cal Jeffrey. We first met in 1998 when we were both at Check Point Software. We've remained great friends and have collaborated multiple times. I affectionately call him my personal SMEE—subject matter expert on everything! Joking aside, Cal is …
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In another two-part episode, I sit down with a long-time cybersecurity professional and personal friend, Cal Jeffrey. We first met in 1998 when we were both at Check Point Software. We've remained great friends and have collaborated multiple times. I affectionately call him my personal SMEE—subject matter expert on everything! Joking aside, Cal is …
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Part 2 My special guest on episode 62 (in two parts) is a long-time Information Security Executive, entrepreneur, and investor. Todd Beebe cut his teeth in the industry attempting to find his way into other people's systems and networks but turned those skills into a long and successful career bolstering and protecting systems and networks. It was …
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Part 1 My special guest on episode 62 (in two parts) is a long-time Information Security Executive, entrepreneur, and investor. Todd Beebe cut his teeth in the industry attempting to find his way into other people's systems and networks but turned those skills into a long and successful career bolstering and protecting systems and networks. It was …
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I'm finally back with a new video format. Thanks for sticking with me. I've decided to run solo in this episode and show one of the most popular presentations I've delivered in the last few years. It's not just a bunch of slides; I show a number of very cool sites too! (links below) I hope you enjoy it! (Special thanks to Jason Prost for the initia…
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