Listen Here

| |

Conversation
Highlights

  • Kyle’s Transition from Government Cybersecurity to Entrepreneurship: Kyle shares his journey from conducting offensive cyber operations within the government to founding Huntress, highlighting the shift from high-stakes government work to the entrepreneurial challenge of building a cybersecurity company.
  • The Genesis of Huntress: Starting with a desire to “wreck hackers,” Kyle discusses the early days of Huntress, including the initial challenges of market education and finding the right go-to-market strategy through managed service providers (MSPs).
  • Overcoming Early Stage Challenges: Kyle reflects on the difficulties of convincing small and medium-sized businesses (SMBs) of the importance of cybersecurity and how these challenges led to a pivot in Huntress’ approach by partnering with MSPs to reach their target market.
  • Fundraising Insights: Kyle shares his experiences and lessons learned from fundraising, emphasizing the importance of storytelling and the balance between sharing a compelling vision and realistic projections to attract the right investors without unnecessary dilution.
  • The Importance of Addressing Imposter Syndrome: Kyle discusses the significance of recognizing and addressing imposter syndrome within his team and the broader startup ecosystem, highlighting the impact of founder influence on team morale and performance.
  • Adapting to a Competitive Landscape: As the cybersecurity market becomes increasingly crowded, Kyle outlines how Huntress maintains its competitive edge through a unique value proposition that focuses on lowering the total cost of ownership for its customers.
  • Vision for the Future: Looking ahead, Kyle articulates his vision for Huntress, not just in terms of potential financial milestones like an IPO, but more importantly, in terms of the company’s mission to protect the 99% — the often overlooked SMBs vulnerable to cybersecurity threats.
  • Personal Growth and Founder Advice: Kyle shares personal anecdotes and advice for fellow founders, emphasizing the importance of resilience, the value of peer support, and the necessity of continuous learning and adaptation in the journey of building a successful company.

Actionable
Takeaways

Market Education is Key:

Initially, SMBs underestimated the need for cybersecurity. Kyle's journey underscores the importance of educating your target market about the value and necessity of your product, especially when it addresses non-obvious threats.

Strategic Partnerships for GTM Success:

Huntress leveraged partnerships with MSPs to effectively reach and serve SMBs. This approach can be crucial for startups looking to scale their solutions in markets where direct access to end customers is challenging.

Storytelling in Fundraising:

Kyle’s experiences with fundraising emphasize the power of storytelling. Articulating a compelling narrative that balances vision with realism can significantly impact your ability to attract the right investors and secure optimal terms.

Long-Term Vision Over Short-Term Wins:

Kyle views potential financial milestones like an IPO as steps towards a larger mission rather than ultimate goals. Founders should focus on the long-term impact of their solutions, maintaining alignment with their company’s founding principles.

Address Imposter Syndrome Within Teams:

Recognizing and addressing imposter syndrome can significantly enhance team morale and performance. Founders should actively work to build confidence within their teams, ensuring members feel valued and capable.

Recommended Founder
Interviews

Paul Valente

CEO and Co-Founder of VISO Trust

Paul Valente, CEO and Co-Founder of VISO Trust: $17 Million Raised to Build the Future of Third-Party Cyber Risk Management

Danny Lopez

CEO of Glasswall

Danny Lopez CEO of Glasswall: $60+ Million Raised to Make the Content Disarm and Reconstruction (CDR) Category Mainstream

Peter Prizio Jr

CEO of SnapAttack

Peter Prizio Jr, CEO of SnapAttack: $8 Million Raised to Power the Future of Threat Management

Arjun Bhatnagar

CEO & Co-Founder of Cloaked

Arjun Bhatnagar, CEO of Cloaked: $25 Million Raised to Build the Future of Data Privacy

Matteo Bogana

CEO and Co-Founder of Cleafy

Matteo Bogana, CEO & Co-Founder of Cleafy: $12 Million Raised to Build the Future of Online Fraud Prevention

Edward Wu

CEO and Founder of Dropzone AI

Edward Wu, CEO & Founder of Dropzone AI: $20 Million Raised to Build the Future of AI SOC Analysts

Stijn Vande Casteele

Founder of Sweepatic

Stijn Vande Casteele, Founder of Sweepatic: $4.4 Million Raised to Build the Future of External Attack Surface Management

Christian Almenar

CEO & Co-Founder of Monad

Christian Almenar, CEO of Monad: $19 Million Raised to Solve the Cybersecurity Big Data Problem

Michael Assraf

CEO & Co-Founder of Vicarius

Michael Assraf, CEO of Vicarius: $29 Million Raised to Build the Future of Vulnerability Prioritization

Philippe Humeau

CEO of CrowdSec

Philippe Humeau, CEO of CrowdSec: $21 Million Raised to Build the Future of Cyber Threat Intelligence

Tiffany Ricks

CEO and Founder of HacWare

Tiffany Ricks, CEO and Founder of HacWare: $2.6 Million Raised to Build the Future of Security Awareness

Rodrigo Leme

Marketing Director of Right-Hand Cybersecurity

Rodrigo Leme, Marketing Director at Right-Hand Cybersecurity: Standing Out in a Crowded Market – Niche Targeting and Customer-Centric Approach

Ani Chaudhuri

CEO & Co-Founder of Dasera

Ani Chaudhuri, CEO & Co-Founder of Dasera: $21 Million Raised to Build the Future of Data Security

Pukar Hamal

CEO and Founder of SecurityPal

Pukar Hamal, CEO and Founder of SecurityPal: $21 Million Raised to Power the Future of Customer Assurance

Scott McCrady

CEO of SolCyber

Scott McCrady, CEO of SolCyber: $20 Million Raised to Build the Future of Managed Security

Paul Lewis

Founder and CEO of Calamu

Paul Lewis, CEO of Calamu: $20 Million Raised to Build the Cyber Storage Category

Spencer Thompson

CEO and Co-Founder of Prelude

Spencer Thompson, CEO and Co-Founder of Prelude: Over $30 Million Raised to Build the Future of Continuous Security Testing

Jason Martin

Co-Founder and Co-CEO of Permiso Security

Jason Martin, Co-Founder and Co-CEO of Permiso Security: $10 Million Raised to Build the Future of Cloud Security

Ian Amit

CEO and Founder of Gomboc

Ian Amit, CEO & Founder of Gomboc: $5 Million Raised to Build the Future of Cloud Security Remediation

Sivan Tehila

Founder and CEO of Onyxia

Sivan Tehila, Founder and CEO of Onyxia: $5 Million Raised to Build the Future of Cybersecurity Performance Management

Tom Jermoluk

CEO of Beyond Identity

Tom “TJ” Jermoluk, CEO of Beyond Identity: $200 Million Raised to Build the Future of Multi-Factor Authentication

Ryan Lasmaili

CEO & Co-Founder of Vaultree

Ryan Lasmaili, CEO of Vaultree: $16 Million Raised to Build the World’s First Fully Functional Data-in-Use Encryption

Marina Segal

CEO and Co-Founder of Tamnoon

Marina Segal, CEO & Co-Founder of Tamnoon: Over $5 Million Raised to Build the Future of Cloud Security

Justin Beals

CEO, Co-Founder of Strike Graph

Justin Beals, CEO of Strike Graph: $12 Million Raised to Build the Future of Automated Security and Compliance

Josh Shaul

CEO of Allure Security

Josh Shaul, CEO of Allure Security: $6 Million Raised to Help Businesses Win the Battle Against Online Scammers

David Brumley

CEO of ForAllSecure

David Brumley, CEO of ForAllSecure: $38 Million Raised to Build the Future of Security Testing

Arie Zilberstein

CEO and Co-Founder of Gem Security

Arie Zilberstein, CEO and Co-Founder of Gem Security: $34 Million Raised to Power the Future of Cloud Detection and Response

Mollie Breen

CEO and Co-Founder of Perygee

Mollie Breen, CEO and Co-Founder of Perygee: $6.4 Million Raised to Build the Future of IT/OT Security

David Etue

CEO of Nisos

David Etue, CEO of Nisos: $33 Million Raised to Build the Future of Managed Intelligence

Mykolas Rambus

CEO & Co-Founder of Hush

Mykolas Rambus, CEO & Co-Founder of Hush: $7.5 Million Raised to Build the Future of Data Privacy

Stephen de Vries

CEO and Co-Founder of IriusRisk

Stephen de Vries, CEO and Co-Founder of IriusRisk: $40 Million Raised to Build the Future of Threat Modeling

John Milburn

CEO of Clear Skye

John Milburn, CEO of Clear Skye: More Than $20 Million Raised to Build the Future of Identity and Access Governance

Dave Mor

CEO and Co-Founder of OneLayer

Dave Mor, CEO and Co-Founder of OneLayer: $15 Million Raised to Protect Private Cellular Networks

Ryan Schonfeld

Founder & CEO of Hivewatch

Ryan Schonfeld, CEO of Hivewatch: $25 Million Raised to Build the OS of Physical Security

Austin Gadient

CTO & Co-Founder of Vali Cyber

Austin Gadient, CTO & Co-Founder of Vali Cyber: $15 Million Raised to Build the Future of Linux Security

Will Wilson

Co-Founder of Antithesis

Will Wilson, Co-Founder of Antithesis: $47 Million Raised to Build the Future of Autonomous Testing

Neil Serebryany

CEO and Co-Founder of CalypsoAI

Neil Serebryany, CEO & Co-Founder of CalypsoAI: $38 Million Raised to Power the Future of AI Security