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On Boards Podcast

On Boards Podcast

Written by: Joe Ayoub & Raza Shaikh
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 A company's Board of Directors or Advisors often has a pivotal role in the success or failure of a business, whether a company or organization lives or dies - - and whether the people who have invested time, money and emotional capital will succeed. On Boards Podcast: A Deep Dive at Driving Business Success, is about everything related to Boards of Directors and Boards of Advisors. Twice a month, in 30 minutes, hear and learn about all aspects of boards and business governance. 
In each episode co-hosts Raza Shaikh and Joe Ayoub interview a guest who has experience with boards - as a board member, a CEO, an investor or an advisor, among other roles, for a conversation on a wide range of topics including: What makes great boards great? What makes a board unsuccessful? How to be a good board member? How to make your board one of the most valuable assets of your company. They discuss public, private, non-profit and start-ups (which they believe is its own category) boards - the work they do, the impact they have and their potential to be profoundly impactful on the organization they serve. On Boards Podcast is for anyone who is a board member, would like serve on a board, is an owner of a business, a member of a non-profit organization, an investor in a business or is interested in Board of Directors or Boards of Advisors or business governance. Economics Management Management & Leadership
Episodes
  • 91. Reinforcing Board Cybersecurity with Gary Evee

    91. Reinforcing Board Cybersecurity with Gary Evee
    Feb 16 2026
    In this episode of On Boards, hosts Joe Ayoub and Raza Shaikh welcome Gary Evee, cybersecurity leader and founder and CEO of Aprivé. His company is pioneering a concierge approach to cybersecurity protection, providing services that protect high-value individuals and families from the digital threat landscape. Drawing on more than 25 years of experience across IBM, cybersecurity leadership, and board service, Gary explains how breaches increasingly take place through individuals rather than systems. He highlights how personal devices, home networks, and online data exposure create vulnerabilities for executives and board members, and why cybersecurity must extend beyond the corporate firewall. He currently serves as the board director of Aware Inc. and is a trustee of Dedham Savings Bank. Key takeaways People are the primary cybersecurity risk Most breaches target individuals and start in simple ways with phishing emails, password reuse, or compromised personal devices. In cybersecurity, people are the weakest links and organizations often lack in providing continued digital protection for executives once they step outside the company's firewalls Home networks and personal accounts often lack even basic security controls and so cybersecurity is a risk for anyone that works remotely, travels, or brings their work home from the organization. It can even impact your family. Aprivé: Personal and enterprise-grade cybersecurity The company offers a white-glove services that protect individuals, their home network, devices and digital footprint Aprivé is unlike other cybersecurity companies and proactively helps people get the protection they need in places outside of the enterprise Aprivé's services cover six pillars Password and credential security Home network hardening Mobile and personal device security Online identity and digital footprint management Financial and account monitoring 24/7 concierge support and incident response Boards and executives are high-value targets with outsized exposure Even the best board portals don't flag when a non-authorized user logs in with stolen credentials taken from a phishing malware or compromised device When an attacker gets access, they can gather information that could lead to reputational damage Aprivé's services ensure everyone within the enterprise is protected, assessing the vulnerability of each individual — especially the C-suite The company also serves high profile and public figures Quotes "People continue to remain the weakest link." " What we found was [people] oftentimes have no one thinking about how to protect them once they left the organization." "Even the best board portals assume that the person that's logging on is legitimate." "If I steal your credentials through a phishing malware, a compromised personal device, the system doesn't see me as an attacker, it sees me as a trusted user." Links Aprive Guest Bio Gary Evee is a visionary entrepreneur, investor, and cybersecurity leader dedicated to redefining how the world's most influential people safeguard their digital lives. As the founder and CEO of Aprivé, he is pioneering the next frontier of personal cybersecurity, Executive & Lifestyle Defense, a model that blends technology, concierge service, and intelligence to protect executives, high-net-worth individuals, and families from the evolving digital threat landscape. With more than 25 years of experience spanning technology, cybersecurity, and business transformation, Gary is known for his rare ability to bridge innovation and trust. Before founding Aprivé, he served as an executive leader in IBM's Cybersecurity Business Unit, helping Fortune 500 CEO's and global enterprises navigate emerging threats while scaling IBM's security portfolio worldwide. In addition to his work with Aprivé, Gary founded Evee Security Consulting Group, advising corporations and public institutions on cyber risk management, identity protection, and incident response. He also founded CyberTrust Massachusetts, a pioneering public-private initiative that develops the next generation of cybersecurity professionals through education, workforce development, and real-work defense programs. Gary erves as a Board Director at Ware Inc. (NASDAW: AWRE), a leading biometrics and identity authentication company, and as a Trustee of Dedham Savings Bank and Charlesbridge Bank. He is also a Visiting Fellow at the National Security Institute at George Mason University, contributing to national discussions on cybersecurity, policy, and technology innovation. A sought-after speaker and thought leader, Gary regularly shares insights on executive risk, digital identity, and the future of cybersecurity, empowering leaders to safeguard what matters most in an increasingly complex digital world.
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    30 mins
  • 90. Building an effective board for post-restructured companies with Jon Weber

    90. Building an effective board for post-restructured companies with Jon Weber
    Dec 17 2025
    In this episode of On Boards, hosts Joe Ayoub and Raza Shaikh welcome Jon Weber, founder of the Jon F. Weber advisory firm and an experienced board leader in operationally intensive, post-restructured companies. Jon has served on over 50 boards. Drawing on more than 20 years of experience at institutional investors, including Icahn Enterprises, Goldman Sachs, and Elliott Investment Management, Jon shares what distinguishes a board that genuinely drives change. The conversation explores how boards are rebuilt following restructurings, why these roles demand significantly more engagement than traditional boards, and how disciplined board composition, leadership, and governance practices can unlock value. Jon also discusses lessons learned from distressed situations, the importance of strong board chairs, and why many boards fall short of their potential. Additional Resources For Jon's articles, podcasts, and webinars on governance and other restructuring-related topics, see https://jonfweber.com/thought-leadership. Key takeaways Early beginnings with operationally intensive investments Throughout his career, Jon had worked for institutional investors who invest in undervalued troubled companies — companies facing challenges relating to talent, strategy, technology, or operational issues. Over the years, Jon has become experienced in overseeing businesses that need very actively engaged boards. Post-restructured boards When a company is restructured, it has new stakeholders, owners, and boards of directors. These boards must be built from scratch, with clear governance structures, committee charters, onboarding processes, and an expectation of deep engagement. Jon characterizes these boards as at least "50% more difficult" than traditional boards. Members of post-restructured boards must be willing to accept the challenge to be deeply involved and do the work necessary to make an impact. Board composition should start with a scorecard Jon likens effective board building to acting as a "casting director." To effectively create a post-restructured board, one has to study the business, learn the industry and its history, and have a clear, deep understanding of the company. Before candidate interviews, a scorecard with explicit criteria and consensus on what will lead to a high performing board is created to assure that recruiting priorities are clear. Strong board leadership is necessary The board chair must have board experience and preferably board leadership experience. The chair must actively manage the board, set expectations for preparation and behavior, facilitate constructive dialogue, and provide regular, direct feedback to the CEO. Without this strong leadership, these boards tend to drift or defer to management. Focus forward, not backward Jon emphasizes that effective boards minimize time spent rehashing historical results and instead prioritize decision-making, problem-solving, and future-oriented discussions. Preparation before meetings, including sharing questions in advance, enables board time to be used for meaningful conversation rather than passive presentation. Quotes "Because it's a new board, it's not tethered to the legacy of the past.""We're not looking for clones of ourselves or people that bring a mirror image of our own beliefs, but rather constructive disagreement at times around particular knowledge of the business."" Investors are human, too, they have biases…the bias that investors have is they prefer candidates who tend to agree with their investment thesis and who have a frame of reference that is consistent with theirs.""A board that doesn't have a leader ends up being led by management—and that's not good governance." Links www.jonfweber.com Guest Bio Jon leads an advisory firm that serves investors in operationally intensive investments. Previously, he created and led operating partner groups for over 20 years at institutional investors, including Goldman Sachs, Icahn Enterprises, and Elliott Investment Management. He has impacted dozens of portfolio companies across a broad range of industries through operational engagement, talent management, and effective oversight, in partnership with management, driving change as a board member, senior executive, and board-level advisor in the Americas and Europe. His roles have included President of Icahn Enterprises, L.P. (NYSE-IEP), CEO of Philip Services Corporation, WestPoint Home, and Viskase, and board member of Aligned Energy, American Railcar Industries, Crescent Communities, Martinrea Honsel, National Energy Group, PLH Group, Promises Behavioral Health, WIND Hellas, Windstream, Xenith Bankshares, and XO Communications. Earlier in his career, Mr. Weber was an investment banker at Morgan Stanley and JPMorgan and a corporate lawyer at Weil. He is a Life Member of the Council on Foreign Relations. Jon earned a J.D., cum laude, from Harvard Law School, and B.S. and M.B.A.,...
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    40 mins
  • 89. Building early stage boards with Firas Raouf

    89. Building early stage boards with Firas Raouf
    Dec 4 2025

    In this episode, Joe and Raza speak with Firas Raouf, co-founder and general partner at Companyon Ventures, a Boston-based VC firm specializing in early-stage B2B software and AI startups.

    Firas shares insights from 25 years as a founder, operator, and venture investor—helping companies transition from founder-led sales to scalable, operationally disciplined organizations. The conversation focuses on how early-stage founders should think about creating their first board, the mistakes to avoid, and why great board dynamics depend heavily on execution.

    Key takeaways

    • Career beginnings

      • 25 years ago, Firas co-founded three startups — two were during the dot-com era and one that became VC-funded, giving him firsthand experience sitting on the receiving end of board advice and investor expectations.

      • Then, Firas was invited to join OpenView while working at Insight Venture Partners and was able to spend 10 years seeing OpenView and its portfolio companies grow.

      • Later he co-founded Companyon Ventures

    • How Companyon Ventures supports the expansion stage investing

      • After early product-market fit, companies hit the "now we need to scale" moment.

      • Companyon Ventures specializes in this transition, helping founders build their first leadership team ,operational discipline, KPIs and dashboards scalable go-to-market engines a plan for capital needs

    • Early-stage boards are about support

      • Firas emphasizes that early boards are not oversight bodies like public-company boards. Their purpose is to surround the founder with people who can help them think strategically, navigate challenges, and build a scalable company.

      • A board can include a seat for common shareholders, lead investors and an independent board member, who is someone with whom the
        CEO is comfortable.

      • Since lead investors can become a long-term board member, Founders
        must evaluate who they are letting in, not only the valuation. Once
        someone is on the board, they're not easy to remove.

    • Boards must evolve as the company evolves

      • As companies grow, the expertise they need changes. Firas suggests cycling out board members after two years.

      • After 18–24 months, it's common for a board member's value to plateau, making board refreshes, new independent directors, or role rotations both healthy and necessary.

    Quotes

    • "A happy board tends to reflect great execution. An unhappy board tends to reflect poor execution."
    • "I do think that you should keep things fresh, so to speak, and so any board member really that has been there more than two years, it's rare that you haven't picked their brain dry."
    • "It's not just about valuation, it's also about who you're going to let into your company, into your house, because once you let them in, you can't get rid of them."
    • "The board of directors for an early-stage startup is the opportunity to have a number of people around the table that can help you navigate and scale your company."

    Links

    Companyon Ventures- Boardroom Confidential

    Guest Bio

    Firas Raouf is the co-founder and general partner of Companyon Ventures, a Boston-based VC firm that invests in early-stage B2B software and AI startups. Before launching Companyon, Firas was part of the founding team at OpenView Venture Partners, where he helped pioneer the "expansion stage" investment model and partnered with dozens of software founders to scale their go-to-market operations. Today, he focuses on helping founders transition from founder-led sales to scalable growth by building leadership teams, operational discipline, and repeatable GTM engines. Firas is known for his hands-on, operator-turned-investor approach and his passion for guiding first-time founders through the challenges of building high-growth software companies.
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    39 mins
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