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.
Scaling Without Breaking What Makes You Great with Desh Urs
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 unce...
Traceable, Role-Aware AI: Transforming Financial Operations with Tom Blair
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...
Scaling Uploadcare and Navigating a Successful Exit without Regrets with Igor Debatur
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 Ride...
Digitizing the Convenience Stores Tech Left Behind with Jason Vego
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 se...
Turning Cybersecurity Compliance into a Catalyst with Jason Young
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.
Ch...
The Scaling Power of Communication at Signpost with Lucas Wilson
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.<...
Bootstrapping, PLG, and the Future of Webinars with Melissa Kwan
Melissa Kwan, cofounder and CEO of eWebinar , is transforming webinar automation by eliminating the repetitive strain of live sessions she describes as "soul crushing." In this episode of the Disciplined Troublemakers podcast, Scott Shagory explores how Melissa's innovative solutions enable technology leaders to scale their companies and boost profitability. Beyond eWebinar, Melissa cohosts the Profit-Led podcast, sharing growth strategies for bootstrap founders, and offers valuable insights on startup life and founder well-being on LinkedIn. The conversation delves into scaling product-led growth tech companies, Melissa’s journey toward building a lifestyle business, and her unique approach to redefining success on her ow...
Building Conversational Commerce in Latin America with Roberto Penacastro Ortega
In this episode of the Disciplined Troublemakers podcast, host Scott Shagory speaks with Roberto Penacastro Ortega, founder and CEO of LeadSales. Since its inception in 2020, LeadSales has provided a CRM and conversational commerce platform that assists small and medium-sized businesses in Latin America with lead management and generation through social media. Roberto discusses the challenges and opportunities of scaling SaaS companies in the region, the role of conversational commerce, and his vision to position LeadSales as one of Mexico's leading tech firms. Explore the future of lead generation and the impact of conversational commerce on business growth.
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AI Agent Opportunities in Healthcare with Ganesh Padmanabhan
Ganesh Padmanabhan is the founder and CEO of Autonomize AI, which utilizes AI Agents and Copilots in healthcare workflows by summarizing unstructured healthcare data for data-driven decision making and improved patient outcomes. Autonomize AI is backed by healthcare VC firm AMV and tech VC firm ATX Venture Partners.
Prior to Autonomize AI, Ganesh helped scale AI companies such as Molecula and CognitiveScale and before that time spent at Dell and Intel.
Quotes
"Choose a meaningful problem, ensure people are willing to pay for the solution, and build a sustainable business." — Ganesh Padmahaban
Unifying Proactive Cybersecurity with Ketan Nilangekar
Ketan Nilangekar is the founder and CEO of ThreatWorx, which delivers a unified solution for proactive cybersecurity, combining application and container security, vulnerability and third-party risk management, and threat intelligence into one seamless platform – called ThreatWatch. Prior to founding ThreatWorx in 2018, Ketan was a technical director at Veritas and prior to this worked for Symantec, Juniper Networks and Cisco. Ketan has a BS and MCS in computer science and patents focused on vulnerability detection and creating snapshots and backups
Quotes
"Think of proactive cybersecurity measures as vaccines, inoculating your enterprise against digital threats." - Keta...
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...
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...
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!
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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...
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...
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 yo...
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...
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 el...
