Episode 116 - Start-Up Secure with Chris Castaldo

Jan 26, 2021

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In this episode of the Hacker Valley Studio podcast, Ron and Chris are joined by Chris Castaldo, Chief Information Security Officer at Crossbeam and author of Start-Up Secure: Baking Cybersecurity into Your Company from Founding to Exit. Throughout his career, Chris noticed that the same cybersecurity related problems surface but there are many different ways to solve them.

Chris has always been passionate about startups and has plans to one day start his own company. While going through lists of top 10 books for startups and entrepreneurs he didn’t find any that mentioned how to do cybersecurity at a startup. This a significant gap for startups, not baking in cybersecurity early results in expensive rework 4-10 years after the startup is founded. This led to Chris writing Startup Secure - his goal was to create a guide and methodology for startup founders to avoid the expensive mistake of not baking cybersecurity into the startup in the beginning.

As the episode progresses, Chris highlights the difference in challenges for startups that are B2B (Business-to-Business) vs B2C (Business-to-Consumer). Cybersecurity startups must weigh the risks of building a product and building a secure company. It’s easier to implement all of the security controls offered by a solution when the startup is 20 employees or less because there is less impact on users and business functions. When cybersecurity startups are selling to organizations with cybersecurity teams, the startup is asked tough questions. For example:

What is your vendor review process?
Is your startup leveraging cloud security controls?
What is your privacy policy?

As a cybersecurity professional, Chris emphases the importance of networking with other professionals. There is an increase in virtual conferences and adoption of LinkedIn. Asking questions to the leaders in the field and providing mentorship to others both provide a significant impact while cultivating your career. Chris also highlights the importance of following up on conversations to build relationships and securing opportunities.

When transitioning from engineer to CISO, Chris found that being intentional and purposeful with his time was impactful in his transition. He developed these skills by reading books about stoicism. He found that focusing on “the right thing to do” was tough because of constant distractions but being purposeful was the solution to distraction. Instead of focusing on all the things that were on his plate he would break down his goals into smaller chunks and give them his undivided attention for a specific amount of time.

Moments During This Podcast:

0:00 - Intro

1:57 - Chris Castaldo on Hacker Valley Studio Podcast

2:47 - Chris’ start in cybersecurity as a red team member

3:50 - Why did Chris write his book Startup Secure

6:58 - Challenges of implementing cybersecurity at a startup

9:56 - What excites Chris about cybersecurity

13:35 - How do you immerse yourself in learning about cybersecurity?

17:33 - Surprises when transitioning from engineer to CISO

22:43 - Core tenants of solving hard problems

25:53 - Protecting the crown jewels at an organization during a breach

33:38 - Advice on sharing knowledge with the world

Links:

Pre-order Start-Up Secure: Baking Cybersecurity into Your Company from Founding to Exit