From the Corps to 50 Strong with CEO Omar Dennis

Marine Corps veteran and cybersecurity entrepreneur Omar Dennis joins Freddie Kim to unpack the real story behind acquiring a business, scaling from 1 to 50 employees overnight, and leading with emotional intelligence. Omar is the CEO of Sedulous Consulting Services, a firm that now supports federal, healthcare, and commercial clients in high-stakes cyber missions. He shares how a single question led to a 6-month M&A process, why fear is just data, and how EQ – not a degree – helped him navigate layoffs, culture shifts, and customer expectations post-acquisition.

We get tactical on evaluating team fit, how to deliver hard news with respect, and the business case against hiring C-players. If you're thinking about buying a business or leading one through change, this is a must-watch.

#veteransintech #businessgrowth #fearlessleadership
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Connect with our guest:
🎖 Marine Corps Veteran. 🧑‍💻 Cybersecurity CEO. 📚 Continuous Improvement Champion.
🔗   / sedulousomar  
🛡️ https://sedulous.com/
📘 Resources:
Kaizen methodology: https://kaizen.com/what-is-kaizen/
Understanding Primary and Secondary Emotions: https://www.simplypsychology.org/prim...

⏱️ CHAPTERS:
01:10 – Omar’s Cybersecurity Journey
A quick look at Omar’s military background and cyber career.

03:56 – From 1 to 50: The Power of Acquisition
How Omar went from one contractor to 50 employees overnight.

05:19 – Recognizing and Managing Fear
Omar explains how managing fear shaped his leadership.

07:32 – Building Confidence Through Mission
How defining personal mission and staying steady under pressure builds trust across teams.

11:15 – SBA Secrets and Seizing the 7%
Omar discovers an underused SBA program that changes everything.

15:25 – The Risk and Reward of Debt
Omar gets real about signing the SBA loan and leading through fear with clarity, courage, and process.

20:08 – Culture Reset
He details how Sedulous 2.0 set the tone post-acquisition with clear values and shared ownership.

23:47 – Letting Go With Respect
40% of the team didn’t stay – Omar explains how he handled it.

29:11 – Kaizen and EQ
Omar shares his philosophy of continuous improvement and why EQ is his leadership superpower.

32:30 – Reputation, Relationships, and Reset
Not all layoffs go smooth – he shares lessons learned.

36:16 – Identifying and Elevating Talent
Omar used reviews and offsites to find his top players.

43:39 – Hiring for Mindset
Two bad PM fits led to one big insight: understand your client’s personality before making a hire.

48:01 – Learning from Hiring Mistakes
Two bad PM fits led to one big insight: understand your client’s personality before making a hire.

50:48 – Co-Interviewing With Customers
Sedulous now invites customers to interview hires to ensure technical and personality alignment.

54:00 – Shaping Culture With Action
Omar leads by example, building team culture through consistency, curiosity, and personal care.

58:32 – Primary vs. Secondary Emotions
Anger is a secondary emotion – he breaks it down.

01:02:38 – Omar's Easter Egg “Three Questions” Framework
Omar shares his tactical tool for emotional control: Does it need to be said, by me, right now?

01:05:28 – The Trap of Hiring C Players
He ends with a warning: hiring cheap may save in the short term, but always costs in the long run.

01:09:36 – Final Reflections and Respect
Freddie and Omar close with gratitude, respect, and a shared mission to build teams that last.