Episode 3 - Bryson Bort

A day in the life of an Entrepreneur



Bryson Bort joins LeaderSpeak to explain how relationships, mission, and a willingness to learn unfamiliar business disciplines shaped several different organisations. His experience spans consulting, an attack-emulation product company, and a nonprofit devoted to industrial control system security.

Guest background

Bryson founded the cybersecurity consultancy GRIMM and SCYTHE, which develops an attack-emulation platform, and co-founded the nonprofit ICS Village. He has also served as a cybersecurity and national-security fellow and an adviser to the Army Cyber Institute. Before entering business, he served in the US Army and supported Operation Iraqi Freedom.

Guest links: LinkedIn · X/Twitter

Topics discussed

Entrepreneurship is a team result

Bryson’s first point is that the entrepreneur is not the whole story. He names leaders, technical specialists, and co-founders across GRIMM, SCYTHE, and ICS Village whose work makes each organisation possible. The founder may be a visible spokesperson, but a capable network supplies knowledge, execution, and continuity.

His own transition began after becoming a successful executive responsible for a large offensive-development group. The role had shifted away from serving customers and toward internal argument, making the work less rewarding. He left to create GRIMM as a one-person consultancy, then relied on trusted relationships and people willing to join the effort.

Accessible education and community contribution

Community engagement is part of Bryson’s operating philosophy. His teams build capture-the-flag exercises and other educational material, but he rejects the idea that introductory content is disposable. There will always be newcomers who need a first step.

Challenges therefore need what he calls a spouse test: someone without prior technical experience should be able to follow a tutorial and accomplish something meaningful. SCYTHE’s community work also includes multidisciplinary exercises rather than only pure hacking challenges, exposing participants to problem solving, reverse engineering, and open-source intelligence.

How a founder’s role changes

Bryson describes entrepreneurship as a persistent mental and emotional commitment. The daily role changes as the company grows. Early on, receiving any customer payment feels improbable. Recurring customers then establish that the company is real. A later, painful stage requires moving from a small operation—where every person may perform several critical jobs—to enough scale for specialists and resilient processes.

At SCYTHE, Bryson now spends less time on individual sales operations and more on strategy, forecasting, staffing, and selected customer relationships. He values autonomy and repeatable process so the business does not depend on his involvement in every activity.

Learning capital and commercial sales

SCYTHE emerged from a GRIMM client engagement that exposed an unmet product need. Bryson initially distrusted venture capital, then realised that investors could provide knowledge he lacked as well as money. Product startups consume capital while pursuing growth, so founders need to understand why they are raising, from whom, and what milestone the funding must reach.

Commercial sales was another unfamiliar discipline. Bryson interviewed sales engineers at conferences to learn what their work involved and what motivated them. Bringing in an experienced CTO similarly changed SCYTHE’s direction and addressed the risk of relying on a single founder for both business and technical leadership.

Mentorship and networks

Effective mentoring needs clear goals, cadence, and expectations. Bryson encourages mentees to ask for help without deciding in advance that a busy person will say no. An asynchronous email lets the recipient respond on their own schedule. Those requests and introductions are how networks compound over years.

Key insights

Actionable takeaways

  1. Map the people whose skills complement yours and invest in those relationships.
  2. Design beginner material so a newcomer can complete a meaningful first task.
  3. Document processes and delegate ownership as the company grows.
  4. Learn an unfamiliar business function by interviewing practitioners who do it daily.
  5. Ask mentors for specific help and make it easy for them to respond asynchronously.

Watch the interview

https://www.youtube.com/watch?v=BekleQeJJL4