The Disciplined Troublemakers

Scott Shagory
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The Disciplined Troublemakers

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.

Episodes

  1. Go-To-Market Strategies That Scale with Chris Kirsch

    1 DAY AGO

    Go-To-Market Strategies That Scale with Chris Kirsch

    Welcome back to The Disciplined Troublemakers. In this episode, we discuss successful tech company strategies with Chris Kirsch, Founder and CEO of the Cyber Marketing Clinic and former CEO of RunZero. Chris brings extensive expertise in product marketing and growth from startups to Series A companies. We'll explore establishing a clear Ideal Customer Profile (ICP), the importance of adaptable messaging, transitioning from founder-led sales to scalable models, and developing effective sales strategies. We'll also touch on pricing, product-led growth (PLG), and achieving product-market fit. Chris will share tips on distinguishing between users and economic buyers, building business cases for new products, and using data for lead generation. Join us for valuable insights on scaling tech businesses. Let's dive in! Quotes "The journey of entrepreneurship can begin with a single part-time effort fueled by passion." - Chris Kirsch "Building processes and systems from the start is key to sustainable growth." - Chris Kirsch Featured in this Episode Chris Kirsch Linkedin: https://www.linkedin.com/in/ckirsch Website: Cyber Marketing Clinic Chapters 00:00 - Introduction 01:00 - Managing Complex Network Connections 07:00 - HD Moore on Metasploit and Cybersecurity 15:03 - Quick Product Demos Via Social Media 20:11 - Enhancing Retention Through Streamlined Research 23:51 - Importance of Experienced Directors for Growth 28:24 - Founders’ and VCs’ Incentive Alignment 36:17 - Defining Ideal Customer Profile (ICP) 41:54 - Emphasizing Low Pricing and User Experience 46:22 - Evaluating Customer Value Through Interviews 50:04 - Refining ICP and Market Strategy 57:58 - Challenges in Finding The Right Sales Leader 59:57 - Revenue from Series A Companies Powered by http://heartcastmedia.com

    1h 3m
  2. Managing IT Services and Cybersecurity with Earl Foote

    JAN 7

    Managing IT Services and Cybersecurity with Earl Foote

    Welcome back to The Disciplined Troublemakers. In this episode, we explore IT services and cybersecurity with Earl Foote, the founder and CEO of Nexus IT Consultants, a MSSP based in Utah and a 3x founder on the INC 5000 list.  Nexus IT Consultants provides white-glove IT support and services specializing in outsourced IT support, cybersecurity, compliance, and cloud solutions. Nexus offers managed services to organizations of all sizes and sectors.  The company was recently ranked #41 out of 154 Utah businesses as a top place to work in 2024 by the Salt Lake Tribune.  In his personal time, Earl is a huge music enthusiast with his own band focused on rock and roll.  He also loves shushing down the slopes and in Utah during the winter months. Join us to gain insights into shaping the IT landscape and improving business operations. Let's dive in! Quotes "Regulated firms need strong cyber and compliance practices for annual audits." - Earl Foote "Concentrate on your core competencies, and partner with experts for everything else." - Earl Foote Featured in this Episode Earl Foote Linkedin: https://www.linkedin.com/in/earlfoote Website: https://www.nexusitc.net/ Chapters 00:00 - Introduction 01:26 - Owning 20-25 Guitars Across Locations 04:57 - Tech Partnerships and Innovations 08:06 - Impact of Cybersecurity Compliance on Industries 10:05 - Innovative Solutions for Enhanced Cyber Compliance 15:52 - Cyber Practices: Essential for Compliance 19:34 - High-Growth Security Provider: 93% CAGR, Employee Praise 20:59 - Utah's Top MSP Expands Responsibly Nationwide 24:43 - Strategic Growth and Talent Search 29:34 - MSPs Explained: More Than Basic IT Support 32:30 - Collaborative Tech and Security Enhancements for Large Orgs 35:01 - Improving Tech Compliance for Clients 38:10 - Sales Empowerment, Not Fear-Based 41:35 - Visionary, Growth-Minded Leadership 47:42 - Meditation for Grounding Amid Challenges 49:39 - Growth Mindset and Humility Drive Success 51:57 - Leadership Growth Through Empowering Others 55:15 - Outro Powered by http://heartcastmedia.com

    55 min
  3. Buying Profitable Businesses with Managing Partner Daniel Sweet

    05/20/2024

    Buying Profitable Businesses with Managing Partner Daniel Sweet

    Welcome back to The Disciplined Troublemakers. In this episode, we explore forecasting and financial systems for risk mitigation and business performance. Daniel shares a story of a startup with cash flow problems despite a successful product, emphasizing the need for financial management. We discuss strategies for tech CEOs to increase company value through profit generation, recurring revenue, and task delegation. We also address the aspects of preparing a business for sale, including planning, externalizing finances, and using technology for growth. Join us to enhance your business skills and position your company for success. Let's dive in! Quotes "In our ideal world, sales keep the operator constantly scrambling. That's the right level of growth." - Daniel Sweet "If your profit is fine-tuned to break even and avoid taxes, that's great until you sell, because a multiple of zero is zero."  - Daniel Sweet Featured in this Episode Daniel Sweet Linkedin:  https://www.linkedin.com/in/danielrsweet Website:https://www.sweetviewpartners.com/ https://thekeyssummit.com/ Chapters 00:00- Introduction 07:19- Market Gaps & Bootstrapped Entrepreneurs 11:32- Struggles in Small Business Management 19:04- System Challenges & Instant Insights 22:34- Retaining Ownership: Strategy Discussion 24:25- Consequences of Poor Financial Planning 29:04- Exponential Growth: Contact Scott at Purple Finch 30:53- Leveraging Experience for Growth 35:47- Tech for Efficiency, Not Job Cuts 38:23- CRM & Staff Training for Success 39:37- Practical SaaS and Tech Strategies 44:40- Navigating Financial Uncertainties 46:27- Financial Focus for Successful Selling 50:40- Summit for Freedom & Happiness 52:49- Complimentary Speaker Access 57:20- Effective Tools for Small Businesses 59:24- Outro Powered by http://heartcastmedia.com

    1 hr
  4. Owning Your Tech Company's Financial Truth with Anthony Nitsos

    05/06/2024

    Owning Your Tech Company's Financial Truth with Anthony Nitsos

    In Episode 4 of The Disciplined Troublemakers, our exceptional guest Anthony Nitsos delves into the SaaS industry's evolution towards a targeted go-to-market approach. Explore product pricing strategies and negotiation dynamics, influenced by business expert Frederick Pohl. Uncover Anthony's expert guidance on navigating SaaS finance and overcoming market disruptions. Gain valuable insights into the CFO's pivotal role in managing cash flow and key metrics like ARR and NRR. Join us for an in-depth exploration of the SaaS landscape, filled with practical advice for CEOs and founders tackling today's obstacles. Quotes "Businesses empower individuals to fulfill responsibilities and care for loved ones effectively." - Anthony Nitsos "Every decision impacts profit and cash flow. Understanding their origins improves effectiveness, especially for C-suite executives."- Anthony Nitsos Featured in this Episode Anthony Nitsos LinkedIn: ​​ https://www.linkedin.com/in/anthonynitsos Website: http://www.saasgurus.io/ Chapters 00:00 - Introduction 03:51 - Operations: Cash runway and sales growth vital 08:01 - Shorter CEO terms allow more focus 12:11 - Consistency in strategy and vision is crucial 14:42 - Understanding value of recurring revenue and evaluation 18:05 - Problem? Bring a solution, valuable for clients 23:03 - SaaS Gurus help CEOs price contracts strategically 24:28 - Negotiation involves determining what market will bear 27:32 - $500,000 ACV, $50,000 Contract: CFO's Focus 32:56 - Shifting to exponential growth, struggling VC-backed SaaS companies 36:10 - Valid product, strong market strategy crucial. Executing both 37:55 - CFO role extends beyond finance, sales, marketing 41:05 - Overcoming technical details to move forward successfully 44:35 - Exciting and dynamic place for teams and technology 54:44 - Outro Powered byhttp://heartcastmedia.com

    55 min
  5. Addressing Hallucinations - LLMs You Can Trust with Scott Cohen

    04/22/2024

    Addressing Hallucinations - LLMs You Can Trust with Scott Cohen

    Welcome back to Disciplined Trouble Makers! In this episode, we'll dive into the AI world with Scott Cohen from Jackson AI, known for groundbreaking work with the Department of Defense. Scott explores AI's ROI, scalability, and the buzz around AI hallucination. Uncover Jackson AI's unique strategies and the importance of human creativity in the age of advanced AI. Discover their commercial shift and funding goals, bringing AI capabilities to the forefront. Tune in to learn how Jackson AI combines innovation with confidence for the future of AI. Quotes "If we solely relied on AI, the spark of creativity would be lost. Instead, AI's true power lies in empowering us to reach new heights." - Scott Cohen "Maintaining a human element in AI operations ensures guidance towards tasks and broader objectives." - Scott Cohen Featured in this Episode Scott Cohen LinkedIn: ​​https://www.linkedin.com/in/scottncohen Website: http://jaxon.ai/ Chapters 00:00 - Introduction 04:04 - Focus on Specific Industries for AI 09:46 - Verification for Token Prediction Models 11:35 - Hallucinations vs Inaccuracies in Transformer Models 15:39 - Efficient AI Building with DETAIL Tool Chain 19:39 - Cooking Skills: Learning and Adapting 20:19 - Enterprise Costs and Impact Inquiry 24:27 - Human-Driven Decision-Making 28:12 - Scott Shagory Interviews Scott Cohen on Fundraising 32:04 - Commercial vs. Government: Value Propositions 34:46 - Balancing Human Uniqueness with AI in Business 37:03 - Human-AI Communication in the Workplace 41:53 - Collaboration Issues in AI Project Failures 45:10 - Navigating Organizational Hierarchy Challenges 47:07 - Importance of Educational Outreach in Data Science Teams 52:50 - Conclusion

    53 min
  6. Negotiating with a Psychological Edge with Al McBride

    01/22/2024

    Negotiating with a Psychological Edge with Al McBride

    In this episode of "Disciplined Trouble Makers," negotiation and communication coach Al Mcbride shares valuable insights on the complexities of negotiation. Discover the impact of emotions and mindset, the value of trust and rapport, and effective strategies for creating deals. Join host Scott Shagory and Al Mcbride to gain a fresh perspective and practical advice for navigating negotiation in today's business environment. Quotes "Exercising bravery involves taking a step outside the familiar confines and expressing your needs with assertiveness."–Al Mcbride "Negotiation is all about adopting better rituals, letting go of what doesn't serve you, and being mindfully aware." - Al Mcbride Featured in this Episode Al Mcbride LinkedIn: https://www.linkedin.com/in/aliste/ Website: www.almcbride.com Upcoming Book: https://almcbride.com/book/ Chapters 00:00 - Introduction 00:15 - The Pressure on Business Leaders: Balancing Emotions in Negotiation 10:06 - Mutual Benefit in Negotiation: Going Beyond Self-Interest 11:52 - Embracing Vulnerability: Clear Goals and Authentic Negotiation 20:48 - The Significance of Strategy: Navigating Negotiation with Clarity 26:12 - Role and Identity in Negotiation: Taking Ownership of Emotional State 29:34 - Operational Fitness with Purple Finch Group: Assisting CEOs 38:16 - The Cost Breakdown Gap: Crucial Knowledge for Salespeople 44:06 - Enlightenment Through Philosophy: Personal Growth and Methods 45:30 - Gender Differences in Negotiation: Personal vs. Cause-driven 51:51 - Condensed Wisdom: Books as Vessels of Knowledge 56:17 - Honesty and Caution: Building Strong Interpersonal Relations 01:00:35 - Conclusion Produced by heartcastmedia.com

    1h 1m
  7. Defining Cybersecurity in Economic Terms with CEO Joe Saunders

    01/08/2024

    Defining Cybersecurity in Economic Terms with CEO Joe Saunders

    In this episode of "Disciplined Trouble Makers," host Scott Shagory engages in a captivating conversation with Joe Saunders, the CEO and founder of RunSafe Security. Together, they delve into the dynamic world of cybersecurity and tech entrepreneurship. From addressing the pressing need for memory safety in the government sector to navigating the intricacies of building a resilient tech company, Scott and Joe share insights and valuable lessons learned from their experiences in the industry. Join them as they explore the significance of memory safety, discuss the nuances of tech company growth, and highlight the power of improv in fostering effective communication and teamwork. This thought-provoking episode provides a unique perspective for tech leaders and entrepreneurs, offering a deep dive into the ever-evolving landscape of technology and innovation. Quotes "You want to make other people look good. Whether it's your customer, a colleague in a meeting, or anyone else, the goal is to be selfless and create opportunities for others to shine." -Joe Saunders "One of the most important things that I've learned is having a really good framework about who you are and who your company is." -Joe Saunders Featured in this Episode Joe Saunders CEO, RunSafe Security LinkedIn: https://www.linkedin.com/in/joesaunders/ Website: www.runsafesecurity.com Podcast: https://pod.co/lessons-from-the-school-of-cyber-hard-knocks Chapters 00:00 - Introduction 00:15 - Building Resilient Software: RunSafe's Mission to Eliminate Vulnerabilities 05:27 - Adapting Economically in an Uncertain Landscape 09:35 - Shaping Intent and Navigating Economic Perspectives 14:12 - Aligning Efforts and Educating on Vulnerabilities 15:05 - Selling the Future: The Complex Process and Buyer Education 18:41 - Discussing Gremlin's Solutions for Tech Companies 24:32 - Cash Flow Positive and Yearning for Growth Opportunities 27:08 - The Importance of Effort: Going Above or Below the Line 31:27 - Shifting Towards Open Source: Software Trends in Embedded Devices 34:13 - The Open versus Closed Source Debate: Perspectives and Insights 37:50 - The Art of Improv: Making Others Shine in Collaboration 41:09 - Embracing Mistakes and Fostering Resilience in a Learning Culture 47:14 - Learning through Experience: Structure and Risk-taking in 53:01 - Conclusion Produced by Heartcast Media http://www.heartcastmedia.com

    54 min

  8. 09/07/2023

    Pilot Episode

    Get ready to embark on a journey into the world of tech innovation and entrepreneurship with the debut episode of the Disciplined Troublemakers Podcast! Join me, your host, Scott Shagory, as we dive headfirst into the dynamic universe of technology CEOs and their incredible stories of scaling, profitability, and successful exits. In this weekly show, we'll unravel the secrets of visionary leaders who dared to challenge the status quo, disrupt industries, and build extraordinary companies – all on their own terms. Tune in to gain exclusive insights that will empower tech CEOs and leaders to elevate their game and drive real impact in their organizations. Are you ready to become a disciplined troublemaker and make waves in the tech world? Then don't miss a single episode of this podcast!

    2 min
  • 8 Episodes

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.

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