The Thoughtful Entrepreneur Podcast Por Josh Elledge of UpMyInfluence.com arte de portada

The Thoughtful Entrepreneur

The Thoughtful Entrepreneur

De: Josh Elledge of UpMyInfluence.com
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You’re gonna love this DAILY, commercial-free entrepreneur spotlight show. We feature CEOs and founders of 6-9 figure B2B companies. Agencies, coaches, consultants, and other leaders share not only their success stories - but their advice for business leaders focused on business growth. You’re going to hear real stories from real people all in 15-25 minutes time - perfect for your commute. On this podcast, your host, Josh Elledge encourages entrepreneurs to share not only their expertise but their stories and their hearts. We believe that every person has a unique message which can positively impact the world. Even YOU! If you’d like to be featured on The Thoughtful Entrepreneur, apply here: https://UpMyInfluence.com/guest/https://upmyinfluence.com/privacy/ Economía Gestión Gestión y Liderazgo Liderazgo Marketing Marketing y Ventas
Episodios
  • 2330 - Key Insights for Building High-Performing Organizations with Ninety's Mark Abbott
    Nov 26 2025
    Mastering Business Growth: Insights from Mark Abbott, Founder & CEO of Ninety, on Operating Systems, Culture, and Organizational Maturity

    In this episode, host Josh Elledge sits down with Mark Abbott, Founder and CEO of Ninety, for a deep dive into business operating systems, organizational culture, and the journey of scaling small and mid-sized companies. Mark—drawing on decades of experience in entrepreneurship, software development, coaching, and workplace culture—explains how leaders can build high-performing, resilient organizations by implementing the right frameworks at the right time. This blog breaks down the episode’s key insights and practical guidance to help business owners navigate their company’s growth stages with clarity and confidence.

    Building Mature, Aligned, and High-Trust Organizations

    Mark begins by explaining what a Business Operating System (BOS) truly is: a combination of tools, disciplines, and concepts that help organizations stay aligned, accountable, and scalable. He emphasizes that every company already has an operating system—whether intentional or accidental—and the goal is to consciously design one that matches the business’s stage of development. Popular frameworks like EOS, Scaling Up, and The Great Game of Business offer structured paths, but each company must adopt the tools most appropriate for their maturity level.

    He breaks down the five stages of business development—Formation, Early Growth, Expansion, Maturity, and Legacy—and stresses that leaders must avoid skipping steps. For example, documenting every process too early is counterproductive; focusing instead on clarity, roles, and early team alignment yields better results. As businesses grow, they often mistake size for maturity, creating organizations that look impressive on the outside but lack foundational discipline internally.

    Mark also highlights the importance of culture, trust, and forgiveness. High-performance organizations assume goodwill, set clear expectations, and use trust as a guiding principle—while also acknowledging that not all behaviors should be tolerated. He references research from Dr. Paul Zak to explain how trust chemically fuels team performance and why leaders must foster environments where transparency and accountability thrive. Platforms like Ninety help reinforce these practices by providing tools for meetings, scorecards, vision alignment, and process documentation, ensuring companies build habits that support long-term excellence.


    About Mark Abbott

    Mark Abbott is the Founder and CEO of Ninety, a platform designed to help small and mid-sized businesses implement and sustain business operating systems. With decades of experience across entrepreneurship, leadership development, and organizational design, Mark has coached countless teams on building trust-based cultures and operational excellence. Connect with Mark on LinkedIn.


    About Ninety

    Ninety is a comprehensive software platform built to help organizations adopt, implement, and sustain a Business Operating System such as EOS. With tools for meetings, scorecards, rocks, issues, processes, and organizational clarity, Ninety equips leadership teams with everything they need to run a healthy, aligned, and scalable business. The platform supports both coach-led and self-directed implementations and includes extensive resources for long-term growth and accountability.


    Links Mentioned in This Episode
    • Mark Abbott LinkedIn
    Más Menos
    19 m
  • 2329 - How to Communicate Worth in Your SaaS Pricing Using the Value Equation with Product Tranquility's Dan Balcauski
    Nov 25 2025
    Mastering B2B SaaS Pricing: Expert Strategies from Dan Balcauski of Product Tranquility

    In this episode, host Josh Elledge sits down with Dan Balcauski, Founder and Principal Consultant of Product Tranquility, to uncover the true science behind effective B2B SaaS pricing. With over two decades in software and deep expertise in pricing strategy, Dan explains why pricing is often misunderstood, what founders consistently overlook, and how SaaS leaders can turn pricing from a liability into a powerful growth lever. This blog breaks down the episode’s most actionable insights to help SaaS founders and product leaders build value-driven, scalable pricing systems.

    Why Most SaaS Pricing Fails—and What to Do Instead

    Dan explains that the biggest mistake in SaaS pricing is choosing numbers before validating whether customers actually perceive value. Founders often rush to set a price—$49, $99, $1,000—without first understanding the customer’s pain, alternatives, or what makes the product meaningfully different. Instead, Dan recommends charging something early, engaging customers in honest conversations about value, and validating willingness to pay through real-world interactions rather than internal assumptions.

    He emphasizes that pricing is ultimately about value, not features. Early-stage founders frequently offer too much for too little, or price too high without proving outcomes. Avoiding these pitfalls requires asking the right questions, initiating value conversations early, and documenting everything customers say about cost, alternatives, and perceived ROI.

    Dan also stresses the importance of selecting a pricing model that aligns with how the customer receives value. Whether subscription-based, usage-based, or outcome-based, the model must match customer expectations and internal economics. This approach helps avoid unnecessary friction in the buying process while increasing expansion potential over time.


    About Dan Balcauski

    Dan Balcauski is the Founder and Principal Consultant of Product Tranquility, where he helps B2B SaaS companies build value-based pricing and packaging strategies. With over 20 years of experience in product management and pricing, Dan works with SaaS CEOs and product leaders to align pricing with customer value and business goals. Connect with Dan on LinkedIn.


    About Product Tranquility

    Product Tranquility is a boutique consulting firm specializing in pricing, packaging, and product strategy for B2B SaaS companies. Through proven frameworks and deep market analysis, Product Tranquility helps SaaS founders create pricing systems that accelerate revenue, improve customer alignment, and scale sustainably across growth stages.


    Links Mentioned in This Episode
    • Dan Balcauski LinkedIn
    • Product Tranquility Website

    Key Episode Highlights
    • Pricing must begin with validating customer value—not picking numbers
    • Why charging something early leads to stronger product feedback
    • How to start pricing conversations earlier in the customer journey
    • Choosing the right pricing model based on value delivery
    • Why packaging and tiered pricing increase conversions
    • How to use the Van Westendorp Price Sensitivity Meter
    • Common pricing pitfalls (anchoring too low, freemium overuse, feature-based pricing)
    • Why pricing is an iterative, evolving process—not a one-time...
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    28 m
  • 2328 - Overcoming Skepticism in Hiring Senior Talent Overseas with Rekruuto's Sid Jashnani
    Nov 24 2025
    Unlocking Global Talent and Founder Freedom: Insights from Sid Jashnani of Rekruuto

    In this episode, host Josh Elledge talks with Sid Jashnani, Founder of Rekruuto and certified EOS implementer, about how founders can reclaim their time, scale with confidence, and access high-performing global talent. Sid shares his personal leadership journey, his frameworks for effective delegation, and his expert perspective on hiring senior-level overseas professionals—revealing practical, repeatable systems founders can apply immediately.

    The Power of Global Hiring and Delegation for Founders

    Sid’s story begins on the golf course with his 14-year-old son during a period of serious illness—an experience that reshaped how he leads both at home and in business. Instead of defaulting to advice or correction, Sid embraced curiosity, asking open-ended questions that encouraged deeper connection. This same leadership principle applies directly to business: when founders listen more and prescribe less, teams become empowered, engaged, and more accountable.

    Sid also challenges the common belief that overseas hiring should be limited to entry-level roles. Drawing from his experience in the Philippines, he explains why many mid- and senior-level professionals abroad bring global expertise, strong process orientation, and cultural adaptability—making them strong fits for operations, marketing, finance, and management roles within EOS-driven companies. With proper onboarding and context-sharing, these hires integrate seamlessly and provide exceptional value at a fraction of the cost.

    To help founders free themselves from burnout and low-value tasks, Sid offers his four-quadrant time audit: a simple but powerful system for categorizing activities based on skill and enjoyment. By identifying tasks you are good at but dislike—or those you neither enjoy nor do well—leaders can delegate strategically, reinvesting their energy into high-impact work that drives revenue, growth, and clarity.


    About Sid Jashnani

    Sid Jashnani is the Founder of Rekruuto, a global hiring agency specializing in matching U.S. companies with senior-level talent from overseas. As a certified EOS implementer and seasoned entrepreneur, Sid helps founders streamline their operations, delegate effectively, and scale sustainably. Connect with Sid on LinkedIn.


    About Rekruuto

    Rekruuto helps founders and business owners hire skilled global talent through a risk-free, flexible model. Specializing in mid-level and senior overseas professionals—particularly from the Philippines—Rekruuto provides vetted candidates, trial periods, and month-to-month engagement options. Their mission is to help founders reclaim their time by delegating confidently and scaling with the right people in the right seats.


    Links Mentioned in This Episode
    • Sid Jashnani LinkedIn Profile
    • Rekruuto website

    Key Episode Highlights
    • Why curiosity-based leadership strengthens both family and team relationships
    • The advantages of hiring mid- to senior-level overseas talent
    • Cultural adaptability and global experience of Filipino professionals
    • Sid’s four-quadrant time audit for identifying delegation opportunities
    • How to calculate the value of your time as a founder
    • Rekruuto’s risk-free hiring model and month-to-month flexibility
    • How to start small and scale confidently with global...
    Más Menos
    20 m
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