The Disciplined Troublemakers

Scott Shagory
  • 5.0 (1)
  • Entrepreneurship

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.

  1. When DCIM Infrastructure Starts to Think with Jad Jebara

    Jan 6

    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/

    52 min
  2. How Badger Maps Scaled to $8m ARR w/o VC Fuel

    12/02/2025

    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/

    57 min
  3. Your Financial Story is Powerful with Pam Prior

    07/22/2025

    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/

    56 min
  4. Scaling Without Breaking What Makes You Great with Desh Urs

    07/08/2025

    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/

    51 min
  5. Traceable, Role-Aware AI: Transforming Financial Operations with Tom Blair

    06/03/2025

    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/

    43 min
  6. Scaling Uploadcare and Navigating a Successful Exit without Regrets with Igor Debatur

    05/27/2025

    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/

    38 min
  7. Digitizing the Convenience Stores Tech Left Behind with Jason Vego

    05/13/2025

    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/

    48 min
  8. Turning Cybersecurity Compliance into a Catalyst with Jason Young

    05/06/2025

    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/

    48 min
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About

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.

Information

  • Creator
    Scott Shagory
  • Years Active
    2023 - 2026
  • Episodes
    21
  • Rating
    Clean
  • Copyright
    © Copyright Heartcast Media
  • Show Website
    The Disciplined Troublemakers