In this episode, we’re joined by Oluwadamilola Obamehinti, a cybersecurity executive with over 15 years of experience working across Fortune 100 companies like eBay and the Founder of Cyber Culture.

She shares her journey from building a successful career in cybersecurity to leaving Silicon Valley to start her own company, along with the real strategies that helped her grow her personal brand and expand her influence in the tech space.

We dive into practical insights on breaking into cybersecurity, navigating corporate environments, building a strong C-Suite network, and attracting high-value clients. Oluwadamilola also breaks down the differences between GRC and Incident Response, the evolving role of certifications in tech, and the emerging risks around AI and security.

This episode is packed with actionable advice for anyone looking to grow in tech, transition into cybersecurity, or build a long-term, sustainable career.

⏱️ Timestamps:

0:00 Opening Remarks & Appreciation

1:04 Meet Oluwadamilola Obamehinti

1:33 Cyber Culture & Her Entrepreneurial Ventures

3:23 Her Cybersecurity Career Journey

4:56 Transition Into Entrepreneurship

5:16 Why She Made the Leap

5:54 Biggest Challenge in Building Her Brand

6:30 How She Built Her Personal Brand

8:00 Posting on LinkedIn While Working in Corporate

9:08 Building a C-Suite Network

10:06 Navigating C-Suite Conversations

11:16 9–5 vs Entrepreneurship

12:19 GRC vs Incident Response

13:15 Breaking Into Big Tech

14:58 Do Certifications & Degrees Still Matter?

16:24 Cyber Culture Scholarships & Membership

17:20 Clients & Services

18:59 How Cyber Culture Started

19:41 Tech Exit Strategies

20:45 How to Get Clients

22:00 Cybersecurity Consulting Areas

23:15 AI Security Risks

25:22 Identifying AI Scams

26:54 Roadmap to Top Companies

28:51 Soft Skills in Tech

29:58 Future of Cyber Culture

31:05 Corporate Politics Strategies

33:51 Growing HackerproofHQ

35:00 Closing Remarks

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#Cybersecurity #TechCareers #WomenInTech #AI #PersonalBranding #CareerGrowth #GRC #IncidentResponse #SiliconValley #CyberCulture #SOC2 #Compliance #Infosec

5 senior cybersecurity leaders sit down for an unfiltered conversation about what it really takes to build a career and a security program from the ground up.

This panel covers imposter syndrome in leadership, getting fired for integrity, transitioning from military to cybersecurity, why curiosity beats certifications, personal branding for security professionals, and how trust and relationships are the real foundation of cybersecurity.

PANELISTS:

- Jo Justice — Business Information Security Officer, Leidos :https://www.linkedin.com/in/jo-justice

- Dd Budiharto — Chief Security Advisor, Microsoft (Oil, Gas & Energy): https://www.linkedin.com/in/dd-budiharto-cissp-cisa-cism

- Oyefunke Fayoyin — Chief Information Security Officer, Devo :https://www.linkedin.com/in/oyefunkefayoyin

- Joshua A. Dray — Chief Information Security Officer, San Jacinto College :https://www.linkedin.com/in/joshua-dray

- Todd Beebe — Information Security Officer, Freeport LNG : https://www.linkedin.com/in/toddbeebe

TIMESTAMPS:

0:00 – Guest Arrival & Opening Moments

1:34 – Welcome & Introduction of Panelists

5:30 – Jo Justice: Career Journey into Cybersecurity

9:47 – Joshua A. Dray: Career Journey into Cybersecurity

15:08 – DD Budinarto: Career Journey into Cybersecurity

17:24 – Oyefunke Fayoyin: Career Journey into Cybersecurity

21:39 – Todd Beebe: Career Journey into Cybersecurity

26:22 – What Does a CSO Do? (Roles & Misconceptions)

29:26 – Building Relationships with CEOs & Advancing to the C-Suite

32:35 – Do Certifications & Degrees Matter in Cybersecurity?

34:39 – Showcasing Curiosity & Readiness on Your Resume

39:14 – How Companies Decide Layoffs

41:25 – Does Being Fired Affect Your Reputation?

43:20 – How to Protect Yourself from Layoffs

49:45 – Live Q&A Session

1:06:00 – Appreciation & Closing Remarks

PRESENTED BY:

Hacker Proof HQ — Cybersecurity Consulting & Advisory

Cyber Culture

Baddies in Tech

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Hacker Proof HQ helps companies build security programs, achieve compliance (SOC 2, ISO 27001, HIPAA, PCI-DSS), and develop security strategy from the ground up. Whether you're a startup navigating your first audit or an enterprise strengthening your posture, we can help.

Book a consultation: https://www.hackerproofhq.com/#book-consultation

Website: hackerproofhq.com

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#cybersecurity #CISO #infosec #cybersecuritycareers #compliance #securityleadership #SOC2 #ISO27001 #cybersecurityconsulting #hackerproofhq #TheConnect #CSuite #Cybersecurity #CyberSecurityCareers #CyberLeaders #TechCareers #CareerGrowth #Leadership #ExecutiveLeadership #InfoSec #CyberSecurityJobs #CareerInTech #WomenInTech #TechLeadership #CISO #CSO #ProfessionalDevelopment #JobSearchTips #CareerAdvice #TechIndustry #Layoffs #ResumeTips #Certifications #Upskill #Networking

Why do venture capitalists reject great startup ideas?

In this episode, we sit down with Elena Obukhova, venture capitalist, entrepreneur, and Founder of Supermoon and Supermoon Ventures, to break down what actually gets startups funded and why most founders get it wrong.

With experience across quant finance, venture capital, and global growth strategy, Elena has helped scale fintech, tech, and blockchain companies while building a network of 42,000+ founders and 2,700+ investors worldwide.

We dive into what really drives startup success, from go-to-market strategy and product positioning to investor expectations and team dynamics.

If you're a founder or building in tech, this episode gives you practical insights to raise capital, grow faster, and avoid costly mistakes.

⏱️ Podcast Timeline

0:30 – Welcome

1:22 – Elena’s Journey into Crypto and the UN

4:54 – Supermoon for Founders

6:36 – Idea vs Go-To-Market

8:01 – Red Flags vs Green Flags

10:50 – Product Launch Focus

13:06 – HireHack Growth Strategy

17:51 – Working with VCs

20:38 – Revenue Before Funding?

21:16 – Early Revenue Signals

22:27 – Global Adoption Gap

26:14 – Mistakes That Shaped Supermoon

29:25 – Founder Resilience

31:05 – HackerproofHQ Challenges

32:53 – Sponsorship & Equity

35:55 – Investment Focus

37:07 – Closing

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🔗 Connect with Elena Obukhova

Instagram: [https://www.instagram.com/elenaobkv](https://www.instagram.com/elenaobkv)

Supermoon: [https://www.linkedin.com/company/supermoongroup/](https://www.linkedin.com/company/supermoongroup/)

Supermoon Ventures: [https://www.linkedin.com/company/supermoon-vc/](https://www.linkedin.com/company/supermoon-vc/)

🔗 Connect with Us

Instagram: [https://www.instagram.com/hackerproofhq](https://www.instagram.com/hackerproofhq)

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📧 [Info@hackerproofhq.com](mailto:Info@hackerproofhq.com)

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