The Disciplined Troublemakers
The Disciplined Troublemakers
Scott Shagory
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.
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 SweetFeatured in this EpisodeDaniel SweetLinkedin:  https://www.linkedin.com/in/danielrsweetWebsite:https://www.sweetviewpartners.com/https://thekeyssummit.com/Chapters00:00- Introduction07:19- Market Gaps & Bootstrapped Entrepreneurs11:32- Struggles in Small Business Management19:04- System Challenges & Instant Insights22:34- Retaining Ownership: Strategy Discussion24:25- Consequences of Poor Financial Planning29:04- Exponential Growth: Contact Scott at Purple Finch30:53- Leveraging Experience for Growth35:47- Tech for Efficiency, Not Job Cuts38:23- CRM & Staff Training for Success39:37- Practical SaaS and Tech Strategies44:40- Navigating Financial Uncertainties46:27- Financial Focus for Successful Selling50:40- Summit for Freedom & Happiness52:49- Complimentary Speaker Access57:20- Effective Tools for Small Businesses59:24- OutroPowered by http://heartcastmedia.com
May 20, 2024
1 hr
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 NitsosFeatured in this EpisodeAnthony NitsosLinkedIn: ​​ https://www.linkedin.com/in/anthonynitsosWebsite: http://www.saasgurus.io/Chapters00:00 - Introduction03:51 - Operations: Cash runway and sales growth vital08:01 - Shorter CEO terms allow more focus12:11 - Consistency in strategy and vision is crucial14:42 - Understanding value of recurring revenue and evaluation18:05 - Problem? Bring a solution, valuable for clients23:03 - SaaS Gurus help CEOs price contracts strategically24:28 - Negotiation involves determining what market will bear27:32 - $500,000 ACV, $50,000 Contract: CFO's Focus32:56 - Shifting to exponential growth, struggling VC-backed SaaS companies36:10 - Valid product, strong market strategy crucial. Executing both37:55 - CFO role extends beyond finance, sales, marketing41:05 - Overcoming technical details to move forward successfully44:35 - Exciting and dynamic place for teams and technology54:44 - OutroPowered byhttp://heartcastmedia.com
May 6, 2024
54 min
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 CohenFeatured in this EpisodeScott CohenLinkedIn: ​​https://www.linkedin.com/in/scottncohenWebsite: http://jaxon.ai/Chapters00:00 - Introduction04:04 - Focus on Specific Industries for AI09:46 - Verification for Token Prediction Models11:35 - Hallucinations vs Inaccuracies in Transformer Models15:39 - Efficient AI Building with DETAIL Tool Chain19:39 - Cooking Skills: Learning and Adapting20:19 - Enterprise Costs and Impact Inquiry24:27 - Human-Driven Decision-Making28:12 - Scott Shagory Interviews Scott Cohen on Fundraising32:04 - Commercial vs. Government: Value Propositions34:46 - Balancing Human Uniqueness with AI in Business37:03 - Human-AI Communication in the Workplace41:53 - Collaboration Issues in AI Project Failures45:10 - Navigating Organizational Hierarchy Challenges47:07 - Importance of Educational Outreach in Data Science Teams52:50 - Conclusion
Apr 22, 2024
53 min
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 McbrideFeatured in this EpisodeAl McbrideLinkedIn: https://www.linkedin.com/in/aliste/Website: www.almcbride.comUpcoming Book: https://almcbride.com/book/Chapters00:00 - Introduction00:15 - The Pressure on Business Leaders: Balancing Emotions in Negotiation10:06 - Mutual Benefit in Negotiation: Going Beyond Self-Interest11:52 - Embracing Vulnerability: Clear Goals and Authentic Negotiation20:48 - The Significance of Strategy: Navigating Negotiation with Clarity26:12 - Role and Identity in Negotiation: Taking Ownership of Emotional State29:34 - Operational Fitness with Purple Finch Group: Assisting CEOs38:16 - The Cost Breakdown Gap: Crucial Knowledge for Salespeople44:06 - Enlightenment Through Philosophy: Personal Growth and Methods45:30 - Gender Differences in Negotiation: Personal vs. Cause-driven51:51 - Condensed Wisdom: Books as Vessels of Knowledge56:17 - Honesty and Caution: Building Strong Interpersonal Relations01:00:35 - ConclusionProduced by heartcastmedia.com
Jan 22, 2024
1 hr 1 min
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 SaundersFeatured in this EpisodeJoe SaundersCEO, RunSafe SecurityLinkedIn: https://www.linkedin.com/in/joesaunders/Website: www.runsafesecurity.comPodcast: https://pod.co/lessons-from-the-school-of-cyber-hard-knocksChapters00:00 - Introduction00:15 - Building Resilient Software: RunSafe's Mission to Eliminate Vulnerabilities05:27 - Adapting Economically in an Uncertain Landscape09:35 - Shaping Intent and Navigating Economic Perspectives14:12 - Aligning Efforts and Educating on Vulnerabilities15:05 - Selling the Future: The Complex Process and Buyer Education18:41 - Discussing Gremlin's Solutions for Tech Companies24:32 - Cash Flow Positive and Yearning for Growth Opportunities27:08 - The Importance of Effort: Going Above or Below the Line31:27 - Shifting Towards Open Source: Software Trends in Embedded Devices34:13 - The Open versus Closed Source Debate: Perspectives and Insights37:50 - The Art of Improv: Making Others Shine in Collaboration41:09 - Embracing Mistakes and Fostering Resilience in a Learning Culture47:14 - Learning through Experience: Structure and Risk-taking in53:01 - ConclusionProduced by Heartcast Mediahttp://www.heartcastmedia.com
Jan 8, 2024
53 min
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!
Sep 7, 2023
2 min