Dennis Underwood on Scaling Cyber Crucible: From Military Contracts to a $1.2M ARR SaaS Powerhouse, Mastering Lean Growth with a 10-Person Team, Global Patents & a Mission to Redefine Cybersecurity Through AI Innovation. (Episode 734 - Dennis Underwood)

1. What do you think is the hardest thing in growing a small business?

According to Dennis Underwood, the hardest thing in growing a small business is letting go of someone who’s doing a good job but no longer fits the company’s evolving needs. He explains that as a product company grows and its focus shifts, even capable and loyal team members might not align with new directions. Making those tough decisions—especially without a “services bench” to reassign people—is one of the most challenging yet necessary parts of leadership and sustainable growth.

2. What's your favorite business book that has helped you the most?

Dennis Underwood’s favorite business book that has helped him the most is Ready, Fire, Aim. He says it changed his perspective on perfectionism and speed in business. Early on, he focused too much on building the perfect product before going to market—a mindset that worked in government projects but not in fast-moving business environments. The book taught him that customers don’t expect perfection; they value progress and adaptability. This lesson helped him launch faster, learn from feedback, and grow Cyber Crucible more effectively.

3. Are there any great podcasts or online learning resources you'd recommend to help grow a small business?

According to Dennis Underwood, a great way to grow a small business is by constantly learning from practical, real-world insights. He recommends checking out resources like Y Combinator’s startup library, which offers valuable articles for founders, and following industry experts on LinkedIn—especially those who challenge conventional thinking and share unfiltered lessons from experience. For podcasts, he values shows like Grow A Small Business, The How of Business, and Masters of Scale, which feature actionable strategies, founder stories, and mindset shifts for entrepreneurs. These platforms, along with consistent self-education and reflection, help business owners stay grounded, adaptable, and ahead of the curve.

4. What tool or resource would you recommend to grow a small business?

Dennis Underwood recommends using tools that enhance automation, efficiency, and clarity in business operations. He highlights Google Gemini as a powerful AI resource for generating content, refining documentation, and improving communication. By uploading company materials and analyzing AI feedback, he identifies areas needing clearer messaging. For small businesses, he believes leveraging such intelligent tools helps streamline processes, boost productivity, and strengthen strategic growth.

5. What advice would you give yourself on day one of starting out in business?

Dennis Underwood’s advice to his younger self on day one of starting out in business would be to have the courage to move faster and fully commit to his vision. He admits he stayed too long in the comfort of government contracting because it felt secure, even though his goals were in commercial software. He says he should have moved out of Washington, D.C. earlier, left behind the “golden handcuffs” of steady contracts, and focused completely on building his product company. His biggest lesson—don’t let familiarity or fear delay your leap into the business you truly want to build.