The Disciplined Troublemakers

Hosted by Scott Shagory

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Jul 2026

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The Disciplined Troublemakers Podcast is a weekly show exploring how technology CEOs and their teams are scaling, expand profitability, and exiting their companies – on their terms. Hosted by Scott Shagory, Disciplined Troublemakers is designed to provide technology CEOs and leaders with insights they can use immediately in their companies and organizations.

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July 21, 202653 min

Scaling SaaS Security: Cybersecurity for Tech CEOs with Roselle Safran

What happens when security finally speaks the language of the business? Most cybersecurity teams are working harder than anyone in the building knows. They are triaging threats, patching vulnerabilities, and running on fumes, and almost none of it lands with the board, the CFO, or the CEO in a way that actually registers. That gap is not a communication problem. It is a structural one. For technology CEOs and founders scaling SaaS companies, the question of how to connect security operations to business outcomes is one of the most underrated scaling decisions you will make. Get it wrong and you are protecting everything equally, which means you are protecting nothing strategically. Get it right and your security posture becomes a genuine competitive asset. Roselle Safran knows this terrain from every angle. She led cybersecurity operations at the Executive Office of the President during the Obama administration, built and sold an incident response platform to McAfee, and is now the CEO and founder of KeyCaliber, a cybersecurity company helping MSSPs and enterprise customers understand what they have, what matters most, and where their real exposures are. She is a Princeton engineering graduate, a frequent speaker on cybersecurity and entrepreneurship, and one of the clearest thinkers in the field on the gap between security jargon and business reality. Key Takeaways Security teams that skip the identification layer and jump straight to detection and response are building on an unstable foundation, because you cannot protect what you do not know you have. Pricing by number of assets creates friction because organizations almost always undercount, and discovering 3,000 assets they did not know existed is a hard conversation when the invoice is tied to that number. Shadow AI is the new shadow IT, and employees dumping sensitive data into unapproved tools are not being reckless, they are just trying to meet a deadline, which is why awareness training matters more than policy alone. Rebuilding a product to be AI native is not just a technology decision, it is a way to erase years of accumulated tech debt that was quietly becoming a ceiling on what the team could ship. Doubling down on existing customer segments, MSSPs, managed service providers transitioning to MSSPs, and enterprise, is a more disciplined growth path than chasing new markets when the product is still maturing. Roselle Safran said, "If you can say we had some major risks related to our critical business applications and we have addressed that, so now we have less risk of our revenue not flowing, that makes sense to someone who does not understand security." Host Scott Shagory said, "Real maturity is when it's considered to be a strategic asset, that is cybersecurity." Timestamps 00:00 Welcome and guest introduction 01:06 The founding frustration behind KeyCaliber 03:15 Why security teams struggle to connect to business outcomes 07:31 Where cybersecurity sits in the org and why it matters 09:21 How the threat landscape has shifted since Roselle's first startup 12:48 Who KeyCaliber's ideal customer is and what they misunderstand 15:39 The NIST CSF pyramid and why identify is the unglamorous foundation 18:18 Shadow AI, unapproved tools, and the awareness training response 21:53 When prospects think they can build asset inventory themselves 26:13 How KeyCaliber prices to avoid asset count disputes 29:58 How Roselle protects time for the work she actually enjoys 34:44 The decision to go AI native and erase years of tech debt 37:03 Best practices for companies navigating a legacy architecture refactor 40:19 What the next 12 to 18 months look like for KeyCaliber 45:32 Making cybersecurity language accessible to non security audiences 48:23 How to reach Roselle and wrap Connect with Roselle Safran LinkedIn: https://www.linkedin.com/in/rosellesafran Email: roselle@keycaliber.com Website: https://www.keycaliber.com

July 7, 202647 min

Embedding Security as a Growth Engine with Jon McLachlan

What if your security program was your best sales tool? Most B2B SaaS founders treat security as a cost center, something to minimize, budget around, and deal with only when it bites them. Jon McLachlan has spent years making the case that this framing is exactly backwards, and the founders who get that earliest tend to scale the fastest. This episode gets into the real mechanics of scaling SaaS companies with security embedded from the start, not bolted on. For technology CEOs and operators weighing build versus buy decisions, the conversation around fractional security teams versus in-house hiring is one of the most honest you will hear on the topic of B2B software scaling. Jon McLachlan is the CEO and co-founder of Ysecurity.io, where he helps SaaS companies build practical embedded security and compliance programs without slowing down product development. He also leads Cyberbase AI, focused on the intersection of AI and cybersecurity, and co-hosts the Security Podcast of Silicon Valley, now over 90 episodes deep. Jon started Ysecurity almost by accident, helping founder friends who needed security guidance, and grew the team to more than 45 people through referrals alone. Key Takeaways Bootstrapping a security firm through referrals is possible when trust is the product: every client at Ysecurity has come through word of mouth, a signal that founders are handing over the keys to people they already believe in. The fractional security team model solves a real gap in B2B software scaling: founders can rent an entire embedded security function, from vCISO to red teaming to GRC, without the complexity of building an in-house team from zero. Checkbox security is a floor, not a ceiling: SOC 2 Type 2 and ISO certifications matter for sales cycles, but the real return on investment comes from integrating security into marketing, sales training, and product positioning so it opens new business. Chasing enterprise clients when your DNA is startup-focused is a costly detour: Ysecurity tried repositioning for large publicly traded organizations, landed a few deals, and found the red tape incompatible with their speed and culture, a pivot that clarified everything. Founder mental health deserves more airtime than it gets: with depression rates among tech founders estimated around 43 percent compared to roughly 9 percent in the general population, protecting personal recovery time, whether running, cycling, or scheduling unstructured space, is an operational decision, not a luxury. Jon McLachlan said, "Security is not just this little box on the side that we should think of as a cost center. The right way to do this stuff is really to integrate it into the entire organization. It is an investment in every sense of the word, and you should expect it to pay off." Host Scott Shagory said, "Sell security without selling security, to overgeneralize. If you can do that, it is just such a potent message, and to be able to really enable gains that are more challenging and yet at the same time provide genuine security, it is not just a checkoff list." Timestamps 00:00 Welcome and guest introduction 01:05 Why Jon and his co-founder Sasha started Ysecurity 02:50 ICP focus: organic growth toward B2B SaaS and AI-enabled companies 03:33 Why ideal customers sometimes still say no, build versus buy 08:47 Scaling from 2 to 45 people: culture, remote work, and staying connected 12:38 Decisions that created disproportionate leverage, and the enterprise pivot mistake 15:17 Selling security as a growth engine, not a cost center 18:19 Where the market undervalues or oversimplifies embedded security 23:43 What work founders must protect: running, biking, and personal recovery 27:22 Silicon Valley pressure, 996 culture, and how Jon navigated a difficult personal period 34:49 What the next 12 to 18 months look like for Ysecurity and Cyberbase AI 37:42 Networking effects, trust, and why referrals are the whole game 42:11 Conviction, authenticity, and what the best founder relationships actually feel like 44:25 Where to connect with Jon and closing thoughts Connect with Jon McLachlan LinkedIn: https://www.linkedin.com/in/jonmclachlan Ysecurity: https://www.ysecurity.io Cyberbase AI: https://www.cyberbase.aiS ecurity Podcast of Silicon Valley: available on major podcast platforms

January 6, 202652 min

When DCIM Infrastructure Starts to Think with Jad Jebara

Scott Shagory opens Disciplined Troublemakers with a scene many leaders know well: complex infrastructure, rising costs, and the pressure to scale without surprises. Across the table sits Jad Jebara, the co-founder, President, and CEO of Hyperview, who has turned hard-earned lessons into a cloud-native DCIM platform built for clarity and speed. Jad’s path runs through two corporate turnarounds—at Peer 1 Hosting, where disciplined execution helped drive a $650MM acquisition by Cogeco, and at IDS Software, which was acquired by PDF Solutions. He’s led finance, supply chain, and IT; run a consulting firm on ERP and process design; and built a career at the intersection of finance and technology. That background now fuels Hyperview’s product-led approach: self-serve deployment, transparent pricing, and global scale without the bloat. In this conversation, Scott follows the thread from problem to practice: how operators move from scattered systems to a single source of truth; how data center teams balance utilization, ESG, and AI-era demand; and how a CEO’s four Rs—responsibility, realism, reflection, and resilience—shape decisions when the stakes are high. If you work in or around critical infrastructure, this story offers a practical map: what to measure, how to act, and how to lead when growth arrives all at once. Press play. Chapters: 00:00 - Intro 00:09 - Entrepreneurship, Scaling, and Insights 03:50 - "Reinventing DCIM for Sustainable Infrastructure" 07:41 - Data Centers and Rising Costs 10:43 - Scaling for Global Data Solutions 16:51 - "Optimizing Industry Sustainability Metrics" 20:54 - Comprehensive Infrastructure Monitoring Solution 23:33 - "Clear AI Roadmap and Vision" 25:40 - "Product-Led Growth and Strategy" 30:44 - Complexity in Tech and Strategy 34:56 - Founder Challenges and Growth Insights 37:19 - Driving Network, AI, and Growth 42:19 - AI's Impact and Leadership Evolution 45:34 - Reflection, Responsibility, Resilience 48:43 - "Empathy and a Learner Mindset" 51:15 - "Discipline Troublemakers Podcast Outro" 51:26 - Outro Quotes: "Make critical infrastructure think. Build the tools we needed. With vision and a learner’s mindset, curiosity becomes an impact."- Jad Jebara "Make the complex simple so others can win. Trust, clarity, and connection matter as much as the tech."- Scott Shagory Key Takeaways: From Frustration to Innovation Making Critical Infrastructure Think Redefining Data Center Management Scaling Globally, Collaborating Locally Sustainability With Real Impact Leading With Joy and Resilience Product Led, Customer Driven Connect with the Guest: Jad Jebara LinkedIn: https://www.linkedin.com/in/jadjebara/ Website: https://hyperviewhq.com/ Connect with the Host: Scott Shagory Website: http://purplefinchgroup.com LinkedIn: http://linkedin.com/in/scottshagory Email: scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/

December 2, 202557 min

How Badger Maps Scaled to $8m ARR w/o VC Fuel

Welcome back to Disciplined Troublemakers. In this episode, host Scott Shagory engages with Steve Benson, the CEO and founder of Badger Maps, a leading mobile mapping solution tailored for field sales professionals. Steve’s journey from tech sales to becoming Google Enterprise’s top sales executive reveals the vision behind establishing Badger Maps in 2012. From a modest beginning, he has grown the company into a global SaaS powerhouse, boasting over 90 employees and an impressive $8 million in annual recurring revenue. Scott and Steve share an insightful conversation about the realities of scaling a SaaS business without the backing of venture capital. They discuss how actively listening to customer feedback helped shape Badger Maps' unique niche in the market. Steve also sheds light on the significance of memorable branding—yes, it often involves an animal! This episode offers valuable insights on remote team dynamics, achieving product-market fit, and the merits of steady growth over the rapid pace often associated with VC-funded ventures. Founders, CEOs, and anyone interested in sustainable technology growth will find pragmatic lessons and candid reflections throughout their discussion. Chapters: 00:00 - Introduction 00:19 - From Sales to Software Startup 06:00 - Naming Trends in Tech Branding 08:14 - Global Team Structure Insights 12:37 - Classic SaaS Success Journey 14:18 - AI Success and Scaling Challenges 19:28 - Strategic Decisions and Market Insights 23:52 - Building Differentiation Through Hard Work 25:51 - Focus Over Ego in Business 30:47 - Sales Mapping and Territory Tools 33:34 - Bootstrap Success Through Customer Focus 34:46 - Competing in Mapping Solutions 40:58 - Tech Priorities: Team, Product, Growth 44:10 - Strategic Foundations for Sustained Growth 46:59 - Early Entrepreneurship and App Building 49:35 - Bliss in Ignorance 52:54 - Incentives Shape Outcomes 56:29 - Outro Quotes: "Identify a niche and deliver real value. With software's extensibility, steady growth and customer focus can lead to lasting success."- Steve Benson "Consistency in serving customers is key. Stay true to your vision, listen carefully, and you'll create something truly impactful."- Scott Shagory Key Takeaways: Solve Problems You Know Deeply Creativity Isn’t Always About Reinventing the Wheel Steady, Sustainable Growth Can Win the Race Listen to Your Customers—And Build Moats Around Their Challenges Know Your Strengths and Stay In Your Lane Bootstrapping vs. VC: There’s No One-Size-Fits-All Path You Will Grow, Even If You Don’t Expect To Endurance Builds Brands That Matter Connect with Steve Benson LinkedIn: https://www.linkedin.com/in/stevenbenson/ Instagram: Steve Benson (@stevebensonsf) Website: Badger Maps - Route Planner for Sales Connect with the Host Scott Shagory http://purplefinchgroup.com http://linkedin.com/in/scottshagory Email: scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/

July 22, 202555 min

Your Financial Story is Powerful with Pam Prior

In this episode of Disciplined Troublemakers, host Scott Shagory sits down with Pam Prior, a CFO and financial coach with over 30 years of experience. Pam has guided a diverse range of clients, including bootstrapped entrepreneurs, private equity investors, Fortune 500 companies, social media influencers, and professional athletes through the complexities of business finances. Scott and Pam discuss how tech CEOs, whether bootstrapped or funded, can refine their financial storytelling and address challenges that arise from overlooked financials. Pam shares practical advice on establishing reliable bookkeeping practices, balancing growth with profitability, developing effective pricing models, and determining the right time to bring in a CFO or restructure the team. For those experiencing uncertainty in their business finances or seeking to implement processes that support sustainable growth, this conversation offers valuable insights and actionable strategies. Learn how to achieve financial clarity and make informed decisions that drive your business forward. Pam Prior is the owner of a bookkeeping and fractional CFO company, a two-time bestselling author, and the host of the Cash Flow and She Said, She Said podcasts. Known as the "Finance Friend in a Foxhole," she is dedicated to supporting 21st-century entrepreneurs. Chapters: 00:00 – Introduction 01:03 – "Numbers Reveal Business Story" 05:26 – Financial Literacy: Key to Business Success 09:15 – Early Stage Business Strategy 10:55 – Diversify Investments, Understand Cash Flow 16:11 – Pricing Strategy for Niche Coaching 18:58 – Value over Price 20:02 – "Charging Difficult Clients More" 26:23 – Scaling Beyond Founder Limits 28:29 – Scaling Challenges and Leadership Transition 33:15 – "Importance of Client Contracts" 34:12 – Founder to CEO: Prioritize Roles 38:27 – Family Dynamics in Business Hierarchies 43:04 – Evolving Documentation Practices 45:35 – "When to Hire a CFO" 49:04 – CFO Role in Business Strategy 51:01 – Embracing Entrepreneurial Agility 54:34 – Interview with Pam on YouTube 54:55 – Outro Quotes: "Seeing your numbers as your business story clears the fog of uncertainty. That clarity brings true freedom."- Pam Prior "When uncertainty lifts, clarity and perspective bring confidence and limitless growth."- Scott Shagory Key Takeaways: Financials Are Your Business Story, Not Just Numbers Clean Books Are Cheaper (and Less Stressful) than Cleanups Lift the Fog: Clarity Equals Confidence For Bootstrappers: Profit, Scale, and Personal Goals Must Be Balanced Scaling from $1M to $5M Means Reinventing Processes—and Yourself Process = Freedom, Not Handcuffs A CFO Is Your Foxhole Ally, Not Just a Number Cruncher Connect with Pam Prior LinkedIn: https://www.linkedin.com/in/pamsprior Website: https://pamprior.com/ Connect with the Host Scott Shagory: http://purplefinchgroup.com http://linkedin.com/in/scottshagory Email: scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/

July 8, 202551 min

Scaling Without Breaking What Makes You Great with Desh Urs

Welcome back to the Disciplined Troublemakers podcast. In today’s episode, host Scott Shagory engages with Desh Urs, founder and CEO of iBridge —a global leader in digital transformation within healthcare, legal services, utilities, and defense sectors. With over four decades of industry expertise, Desh offers valuable insights into scaling infrastructure and software-as-a-service businesses, reflecting on iBridge 's evolution since its inception in 2004. The conversation explores the pressing challenges tech companies face in a swiftly evolving environment, focusing on effective data management, the accelerating advancements in AI, and maintaining security in critical industries. Desh discusses strategies for navigating uncertainty, the importance of enduring customer relationships, and the significance of adhering to core company values amidst growth. Listeners will hear detailed accounts of iBridge 's expansion into international markets like Saudi Arabia, the transition from service-oriented to product-driven models, and how prioritizing both employees and clients has been pivotal to the company's sustained success. This episode provides actionable insights and practical wisdom for CEOs, entrepreneurs, and anyone interested in the transformative role of technology in various industries. Desh Urs brings a wealth of experience from leading roles at TransUnion, Silicon Graphics, and Acxiom Corp., positioning him as a knowledgeable voice in digital transformation and business scaling. Chapters: 00:00 - Introduction 01:06 - Understanding and Organizing Data Value 03:22 - Prioritizing Foundational Questions in AI 06:58 - Data Expertise and Security Challenges 12:53 - Saudi Arabia's Social Transformation 14:32 - Rapid Economic Transformation Ahead 17:23 - Customer-Centric Partnership Success Model 22:10 - Customer Trust Ensures Mutual Success 24:21 - Terminating Contract with CEO 28:44 - Conversation Encouragement for Team Awareness 31:04 - Navigating Information Overload Challenges 36:11 - Transitioning from Services to Product 38:13 - Leadership and Transition in Challenges 43:03 - Decision-Making in a Flat Organization 45:08 - Transformative Social Impact of Connectivity 48:12 - Recruitment and Communication Strategy 50:11 - Outro Quotes: "Prioritize your customers, understand your true purpose, and embrace vulnerability. That's how we grow together."- Desh Urs "Ask who you are and who you serve. In a fast-paced world, wisdom comes from reflection and staying true to your mission."- Scott Shagory Key Takeaways: Transformation Starts with Understanding Your Data Adaptability is Essential in an Era of Rapid Change Security & Trust are Non-Negotiable Scaling Means Embracing Uncertainty—But Moving Forward Anyway Partnerships Over Transactions True Value Lies in Relationships and Integrity Evolving from Services to Products Purpose Beyond Profit Leadership is About Vulnerability and Openness Connect with Desh Urs: LinkedIn: https://www.linkedin.com/in/deshurs/ Website: Home - iBridge LLC Connect with the Host Scott Shagory: http://purplefinchgroup.com http://linkedin.com/in/scottshagory Email: mailto:scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/

June 3, 202542 min

Traceable, Role-Aware AI: Transforming Financial Operations with Tom Blair

Welcome back to the Disciplined Troublemakers podcast, a space dedicated to navigating the complexities of scaling technology companies with increased efficiency and reduced strain. In this episode, host Scott Shagory engages with Tom Blair, cofounder and CEO of http://iCLERK.AI . Tom brings decades of expertise in AI, data, and enterprise technology, highlighted by successful ventures with Performance Livestock Analytics and ClearAg. Scott and Tom examine the impact of applied AI on enterprise operations, focusing on how iCLERK optimizes intricate, repetitive workflows in the financial sector through role-aware autonomous agents. Drawing from his extensive experience, Tom discusses the convergence of AI with long-held ideas and how the swift advancements in technology are opening doors for businesses willing to adapt. Join the conversation as they address the practical challenges and milestones of AI integration, the significance of operational collaborations, and the implications of AI's rapid growth on organizational efficiency, workforce structure, and leadership strategies. For an insightful look into the progression of AI-driven business solutions, this episode provides valuable perspectives. Chapters: 00:00 - Introduction 00:09 - Automating Financial Reporting with AI 06:04 - Streamlining Workflows in IT Industry 08:17 - "Traceable AI for Reliable Reporting" 10:13 - Career Highlights in AI and Analytics 15:00 - "Tech's Emotional Relief Paradox" 18:48 - Deep Institutional Knowledge in Finance 20:13 - Misconceptions in AI Implementation 24:37 - Leveraging AI for Efficient Learning 27:14 - Joyful Life and Intellectual Fulfillment 32:31 - Early Vision: Semantic Image Recognition 33:43 - Bridging Tech Evolution & Human Static 37:58 - "Startups, Technology, and Happiness Curve" 40:06 - "Quick Results Through Clear Purpose" 42:36 - Outro Quotes: "Curiosity drives innovation. Solving real problems brings value and joy."- Tom Blair "Enhancing a single workflow transforms everything. Technology is about progress and simplicity."- Scott Shagory Key Takeaways: Reinventing Professional Workflows, One Agent at a Time From Fear to Opportunity: AI Adoption Is Accelerating Scaling Smarter, Not Harder Depth Matters: Institutional Knowledge as Secret Sauce AI Implementation Without Disruption The Joy of Building—and Continuous Learning The Exponential Future Is Now Start With Small Steps—And Unlock Big Change Connect with Tom Blair LinkedIn: linkedin.com/in/tom-blair Website: http://www.iclerk.ai Connect with the Host Scott Shagory: http://purplefinchgroup.com http://linkedin.com/in/scottshagory Email: scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/

May 27, 202537 min

Scaling Uploadcare and Navigating a Successful Exit without Regrets with Igor Debatur

Igor is the co-founder and CEO of Uploadcare. Founded in 2012, Uploadcare is a file loader, data handler, and Content Delivery Network (CDN) – which ensures data is uploaded w/security, compliance, reliable storage, and a friendly UI. The company’s platform saves internal dev teams months of implementation effort. The platform handles 25 billion + requests per week. The company was acquired by Tiugo Technologies in 2024. Tiugo is a development platform focused on PLG as a GTM and is an affiliate of PSG Equity, a PE buyout firm specializing in mid-market SW companies. Earlier in his career, Igor founded Riders - an app that helped a million users improve 15 action sports disciplines – such as skateboarding and skiing. In this episode of The Disciplined Troublemakers podcast, host Scott Shagory engages with Igor to explore the journey of building Uploadcare. They discuss the challenges of the “build vs. buy” decision that CTOs often face, the complexities of managing large-scale file operations for diverse clients, and the strategies for handling unexpected data surges and expanding into international markets. Igor also shares his experience of selling Uploadcare to a private equity firm while preserving the company's mission and maintaining his role as CEO. This conversation offers valuable insights for founders, technical leaders, and anyone interested in the inner workings of successful SaaS businesses. Discover practical lessons on scaling, leadership, and navigating the evolving tech landscape on The Disciplined Troublemakers. Chapters: 00:00 - Introduction 01:23 - Tech Scaling Insights with Igor Debatore 05:28 - "Scaling Data Movement Challenges" 08:12 - Forecasting Growth Amid Uncertainty 10:46 - Cloud Platforms' Global Multi-Tenancy Operations 15:41 - Challenges Selling Solutions to Engineers 17:53 - Scaling Challenges in Networking 22:21 - "Founder Experience: Selling a Startup" 26:51 - Finding the Right Financial Partner 27:50 - Positive Experience & Learning Opportunity 31:50 - Reflecting on CEO Journey Transformation 34:24 - Human Connection: A Powerful Catalyst 37:39 - Outro Quotes: "I thrive on creating for people and witnessing the joy it brings our team and users. This passion fuels me every day."- Igor Debatur "Passion projects, where you dive in and take initiative, often spark the greatest impact and fulfillment."- Scott Shagory Key Takeaways: Solving Unseen Problems at Scale From Engineer to Global CEO Build vs. Buy—Lessons Learned the Hard Way Automatic Scaling, Real-World Resilience Acquisition as a Strategic Step, not an End Staying True to the Core Motivation The Power of Community and Learning Advice for Founders and CEOs Connect with Igor Debatur LinkedIn: https://linkedin.com/in/debatur Website: https://uploadcare.com Connect with the Host Scott Shagory: http://purplefinchgroup.com http://linkedin.com/in/scottshagory Email: mailto:scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/

May 13, 202548 min

Digitizing the Convenience Stores Tech Left Behind with Jason Vego

In this episode of The Disciplined Troublemakers, host Scott Shagory welcomes Jason Vego, who is the co-founder and CEO of Bevz. Founded in 2020, Bevz is a SaaS platform for independent liquor and convenience stores, helping them centralize and streamline delivery via 3rd party services – such as DoorDash, UberEATS, and GrubHub. Prior to Bevz, Jason founded a dog grooming SW platform, which failed, and earlier in his career he worked at Citrix as Head of Global Employee Communications and Engagemen The conversation highlights Bevz's evolution into a comprehensive inventory management system, enabling stores to efficiently track and sell products both in-store and online. Jason discusses the unique challenges of catering to independently operated stores and outlines the company's ambitious growth plans to expand across thousands of U.S. locations. This episode provides actionable insights for technology leaders and retail enthusiasts aiming to scale their businesses and navigate the complexities of the modern marketplace. Chapters: 00:00 - Introduction 00:09 - Convenience Store Digital Transformation Platform 03:22 - Independent Rural Store Challenges 08:45 - Protein Bar Market Challenges 11:39 - Holistic Approach to Business Growth 15:54 - Snack Food Trends and Market Insights 19:32 - "Building Trust Through Data Insights" 22:54 - "Emphasizing the Human Element in AI" 27:01 - Convenience Retail's E-Commerce Potential 28:14 - Mobile Device Impact on Ordering 32:12 - Scaling Solutions for Tech CEOs 34:09 - Balancing Excel and People Dynamics 40:10 - Leadership Growth and Challenges 41:54 - Value of Fundraising Experience 45:27 - Managing Trade-offs in Business Growth 47:45 - Outro Quotes: "Scaling means building trust and empowering overlooked sectors to thrive."- Scott Shagory "We're transforming independent stores into digital powerhouses, revolutionizing convenience retail."- Jason Vego Key Takeaways: Unlocking Potential in the Overlooked Building Trust and Empowering Growth Navigating Complexity with Simplicity Scaling with Product and People in Mind The Human Touch in a Digital World Visionary Yet Pragmatic Connect with Jason Vego: LinkedIn: https://www.linkedin.com/in/jvego/ Website: https://www.bevz.com/ Connect with the Host Scott Shagory: http://purplefinchgroup.com http://linkedin.com/in/scottshagory Email: mailto:scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/

May 6, 202548 min

Turning Cybersecurity Compliance into a Catalyst with Jason Young

Welcome to the Disciplined Troublemakers podcast. In today’s episode, we speak with Jason Young, founder and CEO of Pylon Cybersecurity. Jason Young is the founder and CEO of Pylon Cybersecurity, a firm he started in 2011. Pylon helps security managers automate network compliance through real-time services which ensures data accuracy and a definitive chain of custody. In 2024 Jason and the team saved the Defense Health Agency, a Combat Support Agency w/in the U.S. DoD that supports medical services readiness for the Army, Navy, and Air Force, $25 million dollars by optimizing their cyber compliance workflows. Chapters: 00:00 - Introduction 00:09 - Scaling Cybersecurity with Jason Young 03:48 - "From Systems Admin to Auditor" 08:01 - Cybersecurity: Cost Center or Strategic Asset? 12:35 - Transforming Conversations for Meaningful Outcomes 15:48 - Understanding Team-Specific Problems 19:37 - User-Centric Strategy for Agility 20:45 - Listening to Junior Insights 26:42 - Exploring Orchestration Layers in DOD 29:50 - Accidental CEO Journey 31:25 - Effective Leadership and Team Retention 34:16 - Rigid Systems vs. Creative Context 38:11 - Breaking Creative Blocks 43:45 - "Evolving Perceptions and Reality" 45:25 - "Meeting People Where They Are" 47:26 - Outro Key Takeaways: Championing Cybersecurity Compliance Empowering IT Operations Creating Value with Technology Culture and Innovation Go Hand in Hand The Power of Listening Quotes: "Turning compliance into a value driver can revolutionize organizations and the entire industry."- Scott Shagory "Solving the real problem unlocks true innovation and value."- Jason Young Connect with Jason Young: LinkedIn: https://www.linkedin.com/in/jason-paul-young/ Website: https://pylonsecure.com Connect with the Host Scott Shagory: http://purplefinchgroup.com http://linkedin.com/in/scottshagory Email: mailto:scott@purplefinchgroup.com Sponsor: Purple Flinch Group https://www.purplefinchgroup.com/ Powered by: http://heartcastmedia.com/