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The Disciplined Troublemakers

The Disciplined Troublemakers

Von: Scott Shagory
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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.Copyright Heartcast Media Management & Leadership Marketing & Vertrieb Ökonomie
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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/

    Powered by: http://heartcastmedia.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/

    Powered by:http://heartcastmedia.com/
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    51 Min.
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