Cybersecurity Needs More Praetorian

Episode Guest:

Nathan Sportsman

CEO @ Praetorian

Available On:

Episode Summary

In this episode, Nathan Sportsman, CEO of Praetorian, shares his journey of building an offensive security firm focused on preventing breaches before they happen. He discusses transforming the company from a well-regarded services business into a product company, overcoming the challenges this created, and the pivotal decisions that have lifted the company to the forefront of the fight against cybercrime.

Nathan also offers an unfiltered picture of the personal sacrifices and tough decisions that were required to navigate situations such as high growth in the midst of the “Great Resignation” and the company first going bust before ultimately taking off.

About the Guest

Nathan Sportsman is the visionary leader, founder and CEO of Praetorian Cybersecurity, a global firm specializing in offensive security and attack surface management. With over two decades of experience in the cybersecurity industry, Nathan has been instrumental in

shaping proactive strategies to prevent breaches and secure enterprises worldwide. His mission-driven approach centers on creating “a world without compromise” by moving beyond traditional detection and response models to emphasize preventive, attacker-emulation techniques. Under his leadership, Praetorian has grown into a trusted partner to more than 20% of Fortune 500 companies, leveraging cutting-edge expertise and technology to address the ever-evolving landscape of exploitable cybersecurity vulnerabilities. In addition to his work at Praetorian, Nathan hosts Where the Warlocks Stay Up Late a docuseries chronicling the oral history of the cybersecurity industry. His passion for preserving the legacy of early pioneers and inspiring future innovators reflects his deep commitment to the field.

Episode Insights

KGK & Company’s analysis of the practical takeaways inside this episode’s conversation on value creation. Learn about KGK

Understanding how current organizational behavior is rooted in past events is critical to business problem solving.

Understanding the noteworthy wins and losses a leadership team or organization has experienced in the past, is both a source of overlooked root cause issues and which solutions to the business’ painpoints are likely to be most effective.

Persistent stress and unsuccessful efforts to overcome a challenge may signal an underfunded initiative requiring intervention.

Prolonged periods of stress (18-24+ months) from repeated efforts to address the same issue, may indicate an underfunded initiative where the vision for the business remains the unchanged, while past ineffectiveness further decreases appetite for risk.

Direction and velocity provide indicators of leadership gaps and effectiveness.

The right leadership creates direction (e.g. tech decisions) and velocity (milestone achievement), so by extension the impact of leadership gaps, upgrades, or additions is ultimately visible within the direction and velocity of achievements in a given area. Therefore measuring direction and velocity of achievements provides a way to evaluate the extent to which leadership is an issue or an effective solution to performance challenges.

One question leaders can use to reveal overlooked opportunities in their organization.

Decisions that leaders wish they would have made sooner can provide categorical visibility to underrepresented success factors. By asking, “What decisions do you wish you had made sooner?”, leaders can uncover who and what has had a positive impact on organizational performance, why, and where further overlooked opportunities may lie.

How CEOs calculate the true cost of a poor hire.

The cost of a poor hire includes associated hard costs, additional overhead to manage the hire, and the resulting opportunity cost to the company. While calculation requires educated assumption, it accurately reflects the real implications for an owner or CEO.

Candidates with previous founder/co-founder experience are an undervalued source of people with an owner's mindset.

When searching for candidates to fill key roles, prior founder/co-founder experience offers an easily-searchable, often undervalued criteria for identifying people with the breadth of experience, sense of ownership, and fortitude to breakthrough barriers to success.

Poor onboarding may be a symptom of inadequate strategic planning.

Poor onboarding, a potential root cause to new leader underperformance, may itself be a symptom of business planning practices that yields vague role definition, inadequate interviewing, urgent hiring, or inadequate metrics for measuring new leader success.

Addressing customer journey adjacencies may offer new differentiation and revenue.

Especially in businesses where differentiation is challenging (e.g. services), making traditionally poor experiences (e.g. separating with a client) into one that is materially value-added, is often a financially sound strategy for differentiation, increasing revenue, and reinforcing the company’s reputation.

Listen Here

Hindsight

Compelling conversations with CEOs and business owners, who share their experiences and what they might have done differently, now that they have the benefit of hindsight.

Best Way to Listen

Visit the episode page for a 1-2 min. overview of the episode, our analysis of the strategic management takeaways within, and for an improved podcast listening experience.

About the Guest

Spencer Kupferman is CEO of PKWARE, an end-to-end data security platform that gives organizations a way to protect data on endpoints, cloud systems, and on-premise infrastructure.

To learn more about the company, go to https://www.pkware.com/

Inside the Episode

in this episode Spencer talks about the crowded state of cybersecurity market, how PKWARE is staying focused from a product and go-to-market standpoint, and thereby differentiating in a market where demand is high, but supply is even higher. Spencer leaves with some great advice on how organizations should handle their weaknesses.

Topics by Timestamp

1:32 – Spencer’s journey to becoming CEO

11:16 – Differentiating in the crowded Cybersecurity market

18:18 – On leveraging channel sales to increase distribution

27:17 – Product Features: To build or not to build

37:59 – Hindsight: focus on strengths, forget fixing weaknesses

Resources Mentioned

Subscribe For New Episodes and Insights

Value Creation Stories From The Middle Market

Hindsight is a podcast featuring conversations with CEOs, investors, and P&L Leaders about the strategies and tactics creating new value for today’s middle market companies.

About The Host

Kanhai is CEO of KGK & Company and has over 20 years of experience helping businesses to see and capitalize on their overlooked opportunities.

Kanhai’s career has enabled him to master the art of asking insightful questions, which he uses on Hindsight to create captivating conversations and draw out elements of a story which even a seasoned executive can learn from.

About The Sponsor

KGK & Company is the leader in data-driven value creation for middle market businesses.

Through our proprietary, data-driven approach we typically deliver ROI within 6 months and a 10x (or more) return over the effective life of our work.

Learn More About The Company

To give middle market CEOs and leaders a proven way to accelerate value creation using their data and our proprietary approach.

Services

Methodology

About Us

Client Work

Podcast

Blog

Complimentary Value Creation Analysis