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The Disciplined Troublemakers

The Disciplined Troublemakers

Written by: 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 Economics Leadership Management & Leadership Marketing Marketing & Sales
Episodes
  • Embedding Security as a Growth Engine with Jon McLachlan

    Embedding Security as a Growth Engine with Jon McLachlan
    Jul 7 2026
    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
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    48 mins
  • When DCIM Infrastructure Starts to Think with Jad Jebara

    When DCIM Infrastructure Starts to Think with Jad Jebara
    Jan 6 2026
    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/
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    52 mins
  • 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: scott@purplefinchgroup.com

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

    Powered by:http://heartcastmedia.com/
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    57 mins
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