Hack & Hustle

Hack & Hustle

Hack and Hustle dives into the challenges and successes in cybersecurity sales and marketing, featuring a fresh topic every week. Get career-boosting insights from top leaders and reps, and candid feedback from CISOs and buyers on what works and what doesn’t. Who knows? You might just end up thanking us from the beach at your next club trip! Sponsored by Delve Risk, the intelligence platform for cybersecurity sales and marketing (delverisk.com). Hack & Hustle Podcast on Youtube Hosted on Acast. See acast.com/privacy for more information.

Episodes

August 27, 2025 28 mins

In this episode of Hack and Hustle, Anthony Johnson and Brad Rager dive into the whirlwind pace of AI development and its transformative impact on businesses. They explore how AI is reshaping industries, the feeling of being an "imposter" in this fast-evolving landscape, and the necessity for leaders to redesign their companies from the ground up.


🎯Are you ready for some real conversations?


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In this conversation, Anthony Johnson and Brad Rager discuss the rapid evolution of AI technology, its potential to automate creative processes, and the challenges businesses face in adopting these innovations. The discussion highlights the importance of leveraging unique data, understanding customer intent, and mastering prompt engineering to fully harness AI's capabilities.


"Data quality is crucial for effective AI implementat...

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In this episode of Hack and Hustle, Anthony Johnson welcomes Chelsea Strong to discuss the importance of building trust in sales, navigating hype cycles, maintaining customer relationships, and the significance of networking. Chelsea shares her insights on how to break into the market as a new seller and emphasizes the value of mentorship and authentic connections in fostering a successful sales career.


"It's all who you know, n...

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In this episode of Hack and Hustle, Anthony Johnson and Brad Rager delve into the complexities of equity options, particularly in the startup environment. They discuss what equity and options are, how they work, and the risks involved in exercising them.


"You made a bet. You made an investment." "You're in a casino."



🎯Are you ready for some real conversations?


Hosted on Acast....

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In this episode of Hack and Hustle, Anthony Johnson and Brad Rager welcome Todd White to discuss the importance of building trust and personal relationships in sales. Todd shares insights from his career, emphasizing that genuine connections and understanding customers as individuals are crucial for success.


"You must be present to win." "If you can help them, they will remember you."


🎯Are you ready for some real conversatio...

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In this episode of Hack and Hustle, Anthony Johnson and Brad Rager welcome Jonathan Sabatini, CRO at Consortium Networks, to discuss the critical role of trust in cybersecurity sales. They explore how building a strong internal culture translates to external success, the importance of hiring for cultural fit, and the challenges of scaling while maintaining that culture.


"Trust is the most critical element of success." "The best ...

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In this episode of Hack and Hustle, Anthony Johnson and Brad Rager welcome Kayla Citrin Thaler, a successful SDR leader. They discuss the importance of authenticity in sales, effective outbound strategies, and the significance of personalization in outreach. Kayla shares her insights on video outreach, tips for leveraging LinkedIn, and the necessity of hard work in achieving sales success.


"You have to do the extra work." "Perfe...

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In this episode, Anthony Johnson and Brad Rager welcome Damian Tommasino, Staff Solutions Engineer at Snyk and Founder of Cyber Informants. They discuss the importance of LinkedIn for personal branding, networking, and career growth, particularly for sales engineers. Damian shares insights on building a community, engaging authentically, and the long-term strategies necessary for success on the platform.


"It's a long game thing....

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May 7, 2025 23 mins

In this conversation, Anthony Johnson and Brad Rager delve into the intricacies of the recruitment process, particularly in the cybersecurity sector. They discuss the roles of recruiters, the types of recruitment models, common misconceptions candidates have, and how candidates can effectively leverage recruiters to advance their careers.


"Recruiters primarily work for the companies that pay them." "Networking and outreach are e...

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April 23, 2025 25 mins

In this episode of Hack and Hustle, Anthony Johnson and Brad Rager discuss the importance of conducting thorough diligence on potential employers. They emphasize the significance of understanding company culture, the impact of industry context, and the necessity of asking the right questions during the job search process.


"Candidates should ask thoughtful questions during interviews." "Networking with former employees can provi...

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In this episode of Hack and Hustle, Anthony Johnson and Brad Rager invited Mark Cervantes to share his extensive experience in sales channels and partnerships, emphasizing the importance of understanding channel dynamics, building relationships, and the long-term commitment required for success.


"Channel sales should be measured by partner-initiated opportunities."


Are you ready for some real conversations?


Join the commun...

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In this episode, Anthony Johnson and Brad Rager discuss sales enablement with Brian Murphy, SVP of Sales and Business Development at NowSecure. They explore Brian's journey into sales, the evolution of sales practices, and the importance of customer-centric selling.


"Be curious, not judgmental." "Sales enablement is about how do you do selling more effectively."


Are you ready for some real conversations?


Join the communit...

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In this episode, Anthony Johnson and Brad Rager discuss strategies for growing your career and networking by giving back and getting involved in the cybersecurity community.


They are joined by Dennis Dayman, CISO of Code 42, who shares his experiences and insights. The conversation covers the importance of joining organizations and coalitions, the benefits of networking, and the value of contributing to the community.


Are you...

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In this episode, Anthony Johnson and Brad Rager discuss the value and ROI of attending cybersecurity conferences as vendors. They explore the different types of conferences, such as Black Hat and RSA, and the benefits they offer to security leaders. They also discuss the importance of networking and building relationships at conferences. The conversation covers strategies for maximizing ROI, including participating in regional bout...

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In this episode of Hack and Hustle, Anthony Johnson and Brad Rager talk with Dmitriy Sokolovskiy, CISO at SEMrush, to discuss the critical intersection of cybersecurity and business. Dmitriy emphasizes the need for vendors to listen actively to security leaders, and build long-term relationships. The conversation also delves into importance of maturity in decision-making processes and how crafting a good story is essential for enga...

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January 29, 2025 24 mins

In this episode, Anthony Johnson and Brad Rager discuss networking strategies to land a job in the cybersecurity industry. They emphasize the importance of networking and building connections with people, both within and outside of your company, industry, and sector. They also stress the need for purposeful networking, having a clear story and objectives, and being open to opportunities.


"Network up and down." "People are findin...

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In this episode of Hack and Hustle, Anthony Johnson and Brad Rager interview Neil Saltman, co-author of  "Cybersecurity Sales: A Buyer and Seller's Perspective."


They discuss:

1) The evolution of cybersecurity sales,

2) The importance of relationships and trust, and

3) The changing landscape of lead generation.


Neil shares insights on what separates successful sales reps from mediocre ones, the significance of understandin...

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December 20, 2024 4 mins

In the very first episode of Hack & Hustle, Anthony Johnson and Brad Rager introduce our podcast, where we'll discuss the ups, downs, and lessons learned in the world of cybersecurity sales and marketing.


The aim? To build a community and provide real conversations to help people in their careers.


The podcast focuses on three main areas:

  1. Helping sellers excel in their current roles,
  2. Guiding individuals in finding the ri...
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