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

    How Badger Maps Scaled to $8m ARR w/o VC Fuel
    Dec 2 2025
    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: mailto:scott@purplefinchgroup.com

    Sponsor: Purple Flinch Group
    https://www.purplefinchgroup.com/

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    57 Min.
  • Your Financial Story is Powerful with Pam Prior

    Your Financial Story is Powerful with Pam Prior
    Jul 22 2025
    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: mailto:scott@purplefinchgroup.com

    Sponsor: Purple Flinch Group
    https://www.purplefinchgroup.com/

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    56 Min.
  • Scaling Without Breaking What Makes You Great with Desh Urs

    Scaling Without Breaking What Makes You Great with Desh Urs
    Jul 8 2025
    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/

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    51 Min.
  • Traceable, Role-Aware AI: Transforming Financial Operations with Tom Blair

    Traceable, Role-Aware AI: Transforming Financial Operations with Tom Blair
    Jun 3 2025
    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/

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    43 Min.
  • Scaling Uploadcare and Navigating a Successful Exit without Regrets with Igor Debatur

    Scaling Uploadcare and Navigating a Successful Exit without Regrets with Igor Debatur
    May 27 2025
    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/

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    38 Min.
  • Digitizing the Convenience Stores Tech Left Behind with Jason Vego

    Digitizing the Convenience Stores Tech Left Behind with Jason Vego
    May 13 2025
    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/

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    48 Min.
  • Turning Cybersecurity Compliance into a Catalyst with Jason Young

    Turning Cybersecurity Compliance into a Catalyst with Jason Young
    May 6 2025
    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/

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    48 Min.
  • The Scaling Power of Communication at Signpost with Lucas Wilson

    The Scaling Power of Communication at Signpost with Lucas Wilson
    Apr 22 2025
    Welcome to another episode of Disciplined Troublemakers, where we explore the landscape of tech companies and the art of scaling businesses effectively. Today, we are joined by Lucas Wilson, CEO of Signpost, who has been steering the company since February 2024 and has achieved remarkable progress.

    Signpost supports small and medium-sized businesses in the home service industry by streamlining day-to-day communications with prospects and customers through a unified platform. Lucas offers his perspective on the challenges and opportunities inherent in scaling a SaaS company within the home services sector, as well as the vital role of online reputation management.

    Our discussion highlights the importance of quality service as a distinguishing factor and traces Signpost's path toward mastering customer communication. Lucas shares his experiences as a turnaround specialist, emphasizing the need to define a company's core identity and the impact of actively listening to customers.

    Join us as we uncover the strategies and insights Lucas contributes, demonstrating why maintaining focus is crucial for growth in today’s rapidly evolving tech landscape. Whether you're a CEO, an entrepreneur, or interested in the mechanics of scaling tech companies, this episode offers valuable takeaways on pursuing progress and excellence.

    Chapters:
    00:00 - Introduction
    01:09 - "Ensuring Quality Customer Communication"
    05:53 - "AI and Live Receptionist Integration"
    08:05 - Exploring AI Communication Platforms
    12:18 - "Uncovering Decision-Making Insights"
    15:24 - Improving Customer Service Efficiency
    19:16 - Urgent Tornado Warning Tech Support
    20:40 - Storytelling and Misunderstandings in Communication
    26:07 - Core Values Drive Market Strategy
    27:08 - Internal Reflection Drives CEO Success
    31:38 - "Empowered Workforce, Secure Future"
    35:34 - Enhancing Service Through Technology
    36:57 - Franchise Tech Integration Challenges
    40:21 - Leadership Roles: Different Mindsets
    43:03 - Outro

    Quotes:
    "Staying focused, listening to our customers, and delivering quality service is what sets us apart."- Lucas Wilson

    "Begin with the end in mind, eliminate obstacles, and build trust through seamless communication."- Scott Shagory

    Key Takeaways:
    Staying True to Core Values
    Learning from Experience
    Team Empowerment
    The Journey of Transformation
    Balancing AI and Human Touch
    Embracing Challenges as Opportunities

    Connect with Lucas Wilson:
    LinkedIn: https://www.linkedin.com/in/lukewilsonsignpostceo/
    Website: https://bias2action.co/

    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/

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    43 Min.