A Solopreneur’s First Imperfect Step with Claire Gallagher

A Solopreneur’s First Imperfect Step with Claire Gallagher

Claire Gallagher, Designer and Solopreneur Strategist, comes to Hacker Valley to break down branding, visibility, and choosing solopreneurship over business ownership. Combining the terms solo and entrepreneur, solopreneurs are a different breed of business owner, and Claire has made it her mission to help them not make the same business mistakes she once made. Claire walks through the essentials of how her business caters to individuals looking to go it alone and how to make an impact while staying small.

Timecoded Guide:

[00:00] Introducing the concept of solopreneurship

[04:32] Shifting to business strategy to better serve a client base

[09:19] Deciding alone as a solo entrepreneur

[16:40] Pricing your work and validating your professional value

[24:46] Making peace with looking silly as a business owner

Sponsor Links:

Thank you to our sponsors Axonius and Uptycs for bringing this episode to life!

The Axonius solution correlates asset data from existing solutions to provide an always up-to-date inventory, uncover gaps, and automate action — giving IT and security teams the confidence to control complexity. Learn more at axonius.com/hackervalley

With Uptycs, modern defenders can prioritize, investigate and respond to threats across the entire attack surface—all from a common solution: uptycs.com.

Why did you choose to go down a path of catering to solopreneurs, versus working with enterprises or small and medium businesses?

Claire has dabbled in building teams and working in larger businesses in the past, but her calling has always brought her back to a company of one. For solopreneurs, Claire explains, it’s not that they cannot afford hiring employees or scaling their business. Instead, a solopreneur’s focus is on the balance between work and life, along with the power and experience to make their own decisions about their business.

“I'm a loud introvert. I could talk all day, but essentially, I'm kind of introverted in secret. Generally, I like to work alone, to get into a creative flow, to not have anybody to answer to. This company of one, this solopreneurship, it suits my energy and my temperament.”

What are some of the pros and cons of going it alone as a solopreneur and keeping your business small?

There are pros and cons in business, no matter the size. Claire’s strongest pro for becoming a solo entrepreneur has been her ability to pivot without impacting anyone but herself. Pivoting towards strategy was a hard decision, but it was so much easier to make on her own. Unfortunately, making decisions on one’s own can also be a con of solopreneurship. Claire has seen clients have a lack of accountability in sticking with their decisions when they don’t have anyone working with them.

“That's a pro, I was able to pivot without having to hire people, sack people, and really invest heavily in changing everything. That's a real plus, I could just pivot like that and it was a decision that I made, and I was responsible for it.”

At what point would you recommend a solopreneur, or content creator, to reach out to someone like you so they could shine in this digital world?

Although solo entrepreneurs thrive in business on their own, it’s important to never go it alone. Claire advises that early stage solopreneurs consider the community around them and build their business with a healthy curiosity in books, online resources, and virtual communities of fellow entrepreneurs. As they progress through their business, Claire also recommends connecting with a coach or strategist, like herself, to go further faster and avoid careless mistakes.

“Solopreneurs think, ‘I'm smart, I can figure this out.’ Yes, you can, but to go further faster, I think you need to work with a mentor or a coach or strategist. You're always going to get further faster by finding somebody who understands what you're trying to achieve.”

What are some of the tenants that you teach people about coming across as authentically as possible?

Branding is a vital element of content creation and business ownership. However, the current world craves branding that comes across as authentic. Claire explains that authenticity comes from a willingness to make mistakes and put yourself out there, even if it feels or looks silly the first time. If a solopreneur is honestly trying to deliver value, that will show through any first-time awkwardness or silliness and still feel authentic to potential clients.

“Starting before you feel ready is really the only way that you can start because you can't know everything until you've tried some stuff. Showing up and making mistakes and maybe seeming a little bit foolish at the start, take it. That's what's gonna happen.”

---------------

Links:

Keep up with Claire Gallagher on LinkedIn and at ClaireCreative.com

Connect with Ron Eddings on LinkedIn and Twitter

Connect with Chris Cochran on LinkedIn and Twitter

Purchase a HVS t-shirt at our shop

Continue the conversation by joining our Discord

Check out Hacker Valley Media and Hacker Valley Studio

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Superhuman Productivity and AI Mastery with Pedram Amini

Superhuman Productivity and AI Mastery with Pedram Amini

What if you could have a conversation with yourself—years into the future? Or leave behind an AI-powered avatar that understands your thoughts, philosophies, and even your voice? In this episode, we explore the mind-blowing potential of AI and its impact on cybersecurity, productivity, and even legacy. Pedram Amini, Chief Scientist at OPSWAT, joins Ron Eddings to discuss his journey from bootstrapped startups to AI-driven innovation. Together they cover topics like the role of AI in cybersecurity, the rise of fake identities in hiring, the ethics of AI-generated content, and why mastering AI tools is no longer optional—it's essential. Pedram shares his workflow for superhuman productivity, his thoughts on deepfakes, and how AI is reshaping how we work and communicate. Impactful Moments: 00:00 - Introduction 02:00 - Meet Pedram Amini, cyber innovator 03:07 - The $17M North Korea insider threat case 06:00 - Fake job candidates and AI hiring scams 09:28 - Deepfakes and AI-driven deception 14:00 - Future of AI-powered personal assistants 20:49 - The reality of bootstrapping vs. VC funding 26:00 - AI in cybersecurity: risk or revolution? 31:00 - “AI isn’t taking your job—someone using AI is” 35:00 - The ultimate AI-powered legacy project   Links: Connect with our guest, Pedram Amini: https://www.linkedin.com/in/pedramamini/ Check out the entire article about the $17M North Korea insider threat case here: https://www.theregister.com/2025/02/12/arizona_woman_laptop_farm_guilty/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

21 Helmi 202536min

Cybersecurity Meets AI: The Good, The Bad & The Janky

Cybersecurity Meets AI: The Good, The Bad & The Janky

There’s no doubt that AI is changing the game in cybersecurity, but not always in the ways we expect. In this episode, Ron Eddings shares his firsthand experience with AI-powered tools that make him a cyber superhero—when they work. From automating security tasks to turbocharging programming workflows, AI is proving its value, but also revealing its limits. Through live walkthroughs and real-world examples, he showcases how AI automates security tasks, accelerates programming, and enhances research—while also showing why some cybersecurity actions should stay human-led.   Impactful Moments: 00:00 - Introduction 02:00 - The good and bad of AI in security 04:00 - Google’s AI weapons controversy 06:30 - Deepfake scams and AI-powered phishing 09:00 - How AI helps (and fails) at programming 12:00 - Automating security research with AI 18:00 - AI-generated meeting notes & productivity hacks 21:00 - What AI should NEVER do 23:00 - The future of AI in cybersecurity   Links: Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

13 Helmi 202522min

A Human-Centric Approach to Cybersecurity with Edna Conway

A Human-Centric Approach to Cybersecurity with Edna Conway

What if cybersecurity was more than just tech—what if it was about the people it serves? In this episode, Edna Conway, Founder and CEO of EMC Advisors, shares her incredible journey from law to cybersecurity and explores the human element often overlooked in technology.  Recorded live at InfoSec Nashville 2024, Edna discusses the intersection of innovation and tradition, the critical role of accuracy in AI, and her vision for cybersecurity's future. From anomaly detection to the wisdom of creating "enclaves," her insights remind us that tech is here to serve people, not the other way around.   Impactful Moments: 00:00 – Introduction 01:22 – Keynote insights: Innovation meets tradition 02:39 – From prosecutor to cybersecurity leader 07:00 – Human-first approach to AI and security 11:40 – LLMs in cybersecurity: opportunities and accuracy 16:34 – Balancing risk with AI use in business 23:06 – Bringing diverse talent into cybersecurity 32:30 – Advice on leadership and collaboration   Links: Connect with our guest, Edna Conway: https://www.linkedin.com/in/ednaconway/ Learn more about ISSA Middle TN here: https://issamidtn.org/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

4 Helmi 202535min

Rise of the Machines: Why Your Attack Surface Has More Holes Than You Think ft Pandian Gnanaprakasam

Rise of the Machines: Why Your Attack Surface Has More Holes Than You Think ft Pandian Gnanaprakasam

Did you know nearly half of your enterprise devices are agentless—leaving your attack surface wide open? In this episode, Ron is joined by Pandian Gnanaprakasam, Co-Founder and Chief Product Officer at Ordr, to discuss the critical risks posed by agentless devices and how orchestration can strengthen your defenses. Pandian shares key findings from Ordr’s 2024 "Rise of the Machines" report, highlighting the risks of overlooked agentless devices. He covers the rapid growth of these devices, strategies to manage vulnerabilities, and how automation can strengthen your defenses.   Impactful Moments: 00:00 - Introduction 04:15 - Why agentless devices dominate the next decade 06:30 - Insights from Ordr's “Rise of the Machines” report 08:50 - Hidden risks: 42% of devices are agentless 11:15 - Solving the "Swiss cheese" problem of security gaps 14:30 - Prioritizing vulnerabilities with business context 18:10 - Orchestration vs. automation: The harmony difference 22:00 - Why visibility is the foundation of security 27:30 - Ordr’s unique approach to securing the attack surface Links: Connect with our guest, Pandian Gnanaprakasam: https://www.linkedin.com/in/gpandian/ Check out Ordr’s Rise of the Machines report here: https://ordr.net/resources/rise-of-the-machines-report-2024 Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

28 Tammi 202538min

How a Game Turned a Watchmaker into a Cybersecurity Pro with Simeon Kakpovi

How a Game Turned a Watchmaker into a Cybersecurity Pro with Simeon Kakpovi

What if cybersecurity training could be as engaging as your favorite game? In this episode, Simeon Kakpovi, founder of the KC7 Foundation, shares how his gamified approach is changing lives and reshaping the cybersecurity pipeline by making cybersecurity education accessible.  From his journey as a threat hunter to building a free online game that teaches real-world blue team skills, Simeon joins Ron to show how creativity and inclusion can unlock potential in unexpected places. Plus, listen to the remarkable story about how a watchmaker with no cyber background landed a dream job at Microsoft—all thanks to KC7.   Impactful Moments 00:00 - Introduction 01:11 - The evolution of cybersecurity 03:03 - Cybersecurity Mergers & Acquisitions 05:38 - Meet our guest: Simeon Kakpovi of KC7 Foundation 06:00 - KC7 wins “Team of the Year” at the SANS DMAs 8:43 - Founding the KC7 Foundation 10:00 - Lessons from Lockheed Martin’s Cyber Analyst Challenge 11:46 - How KC7 gamifies real-world cybersecurity 14:52 - Bringing KC7 to high school and middle school students 16:52 - Expanding access to cybersecurity careers 25:09 - A watchmaker’s journey to Microsoft 34:00 - How to get started with KC7     Links Connect with our guest, Simeon Kakpovi on LinkedIn: https://www.linkedin.com/in/kakpovi/ Check out the Cybersecurity M&A Roundup Article here: https://www.securityweek.com/cybersecurity-ma-roundup-37-deals-announced-in-december-2024/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

22 Tammi 202535min

Managing and Mitigating Cyber Risks For Your Assets with Jerich Beason and Wes Wright

Managing and Mitigating Cyber Risks For Your Assets with Jerich Beason and Wes Wright

What’s the key to mitigating unseen cyber risks? In this episode, Wes Wright, Chief Healthcare Officer at Ordr and Jerich Beason, CISO at WM uncover the complexities of attack surface management (ASM) and its impact on cybersecurity.  Together with Ron, they explain what constitutes an attack surface and introduce practical frameworks like See-Know-Secure, emphasizing the need for complete visibility and data-driven risk mitigation.  Impactful Moment: 00:00 - Introduction 03:00 - Defining attack surface management 06:13 - See-Know-Secure framework  09:05 - Analogies for explaining ASM to stakeholders 15:33 - Building an inventory for asset visibility 20:42 - Convincing leadership: Budget strategies 25:00 - Tools and methodologies for ASM 36:57 - Managed services vs. in-house approaches 43:00 - Starting your ASM journey   Links: Connect with our guests – Wes Wright: https://www.linkedin.com/in/4kidwes/ Jerich Beason: https://www.linkedin.com/in/jerich-beason/ Learn more about Ordr: https://ordr.net/   Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

14 Tammi 202544min

The Year of the Agent: AI, Bug Bounties, and Cybersecurity Insights with Marco Figueroa

The Year of the Agent: AI, Bug Bounties, and Cybersecurity Insights with Marco Figueroa

How will AI redefine cybersecurity in 2025? According to Marco Figueroa, Program Manager for Gen AI at the ODIN Bug Bounty Program, this year is set to be the "Year of the Agent," where AI systems and integrations take a central role.  In this special New Year bonus episode, Ron sits down with Marco to discuss the transformative role of AI in solving cybersecurity challenges. Marco breaks down AI jailbreak techniques, the impact of bug bounty programs on securing AI systems, and why 2025’s fast-evolving tech landscape demands creative thinking. Learn how tools like ChatGPT and Gemini 2.0 are reshaping the industry and why staying adaptable is essential.   Impactful Moments: 00:00 - Introduction 02:14 - Speed vs. safety: AI system challenges 05:30 - Why experience matters more than information 07:45 - Legal stakes for deepfakes and AI 18:36 - Marco’s creative journey in cybersecurity 28:00 - Jailbreaks: Risks and surprising AI findings 37:13 - 2025 predictions: The rise of agents 41:00 - Closing thoughts and the power of community Links: Connect with our guest, Marco Figueroa: https://www.linkedin.com/in/marco-figueroa-re/ Chuck Brooks' 2025 Cybersecurity Predictions article: https://www.forbes.com/sites/chuckbrooks/2024/12/24/cybersecurity-trends-and-priorities-to-watch-for-2025/ Focus Areas for the FaccT Conference News: https://facctconference.org/2025/focusareas “Unreasonable Hospitality” by Will Guidara Book Link: https://www.amazon.com/Unreasonable-Hospitality-Remarkable-Giving-People/dp/0593418573 Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

10 Tammi 202541min

Understanding the Psychology of Cyber Risk with David Shipley

Understanding the Psychology of Cyber Risk with David Shipley

Most people think cybersecurity training is about knowledge, but what if motivation is the real key to success? David Shipley, CEO and Field CISO at Beauceron Security, shares how psychology and neuroscience reshape how we approach security awareness, reducing risks in ways tech alone never could. In this episode, Ron and David examine why people, not technology, are at the core of effective cybersecurity. David teaches us about the SCARF model, warns us about the dangers of overconfidence in training, and explains how gamification can drive meaningful behavior change when it comes to cybersecurity awareness and risk reduction.    Impactful Moments: 00:00 – Introduction 02:00 – David Shipley’s journey from journalist to cybersecurity leader 06:10 – Why motivation outshines knowledge in security training 08:20 – The Dunning-Kruger effect: Overconfidence in cybersecurity 11:17 – How overreliance on tech increases click rates 17:03 – Cybercriminals’ evolving tactics and emotional manipulation 25:00 – Gamification in cybersecurity: Changing security behaviors 30:56 – Using the SCARF model to enhance security culture 39:45 – Emotional intelligence as a defense against AI threats Links: Connect with our guest, David Shipley: https://www.linkedin.com/in/dbshipley/ Learn more about Beauceron Security here: www.beauceronsecurity.com/partner   Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

7 Tammi 202544min

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