That Worked

Callan Harrington
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That Worked

Host Callan Harrington breaks down the careers of top founders and executives, pulling out the key items that led to their success. These are actual career transitions, mistakes, insights, breakthroughs, and general advice that can be immediately implemented.

  1. Matt Farrell - COO at Niobium Microsystems: Succeeding in the Earliest Stages, Evaluating Potential Employees, and Creating Work/Life Alignment

    MAR 13

    Matt Farrell - COO at Niobium Microsystems: Succeeding in the Earliest Stages, Evaluating Potential Employees, and Creating Work/Life Alignment

    Matt Farrell is the COO at Niobium Microsystems, a trusted hardware design company developing high-performance microelectronic components to enable the secure collection, processing, and distribution of critical data. Matt is a multi-time founder and early-stage executive. Before the startup world, Matt was a coach for the University of Dayton Men’s basketball team and later the Assistant Athletic Director at the University of Dayton.  In this episode, you’ll learn: How to create work/life alignment How sports prepare you for startupsHow to evaluate potential employeesWhat to expect in the earliest stages of a company Why you need to have a bias for action in a startup  Follow Matt on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter

    43 min

  2. MAR 6

    Mastering Content Strategy, Delegation, and Creative Efficiency

    In this episode of That Worked, co-hosts Callan Harrington and Sullivan Finlay dive into content strategy, delegation, and maximizing creative output. Sullivan shares how structured planning has transformed his workflow, the power of visual content boards, and why repurposing content is essential for expanding reach without reinventing the wheel. They also break down the 10-80-10 rule of delegation, an approach to outsourcing that helps creators and entrepreneurs focus on high-impact work. Plus, they dive into the role of relationships in business growth and discuss the balance between creative control and efficiency.In this episode, you’ll learn: Strategies for effective collaboration and outsourcingWhy repurposing content can supercharge engagementHow to leverage visual planning tools for content creationThe importance of structured ideation and content pipelinesThe 10-80-10 rule of delegation and how it optimizes workflow Follow Sullivan on TikTok and Instagram Follow Callan on LinkedIn Subscribe to the Newsletter

    21 min

  3. FEB 27

    The Power of Improv, AI-Driven Content, and Buying Back Time for Growth

    In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay explore how improv can transform leadership, the evolving landscape of AI-driven content creation, and why outsourcing is essential for scaling creative work. Sully shares improv techniques—such as adaptability and active listening—that boost effectiveness both on stage and in the workplace, while Callan emphasizes the growing importance of human-driven insights in an AI-saturated environment. Together, they unpack how AI-generated search results are reshaping content discovery, highlight the practical benefits of delegation to reclaim valuable time, and offer candid observations about the world of LinkedIn thought leadership.  In this episode, you’ll learn: The importance of outsourcing to reclaim time and focus on growth.Why improv training can enhance leadership, negotiation, and adaptability.How content creators can balance control with delegation for better output.How AI-generated search results are reshaping content discovery and online trust.Managing frustration and workflow efficiency in a high-demand creative environment.Follow Sullivan on TikTok and Instagram Follow Callan on LinkedIn Subscribe to the Newsletter

    23 min

  4. FEB 20

    The Ethics of AI, Digital Likenesses, and the Future of Content Creation

    In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay dive into the rapidly evolving role of AI in entertainment, content creation, and brand collaborations. They explore the ethical dilemmas of AI-generated personas, the impact of deep research tools on competitive analysis, and how AI is reshaping creative industries. Sullivan shares his perspective on balancing creative integrity with AI-driven scalability, the challenges of licensing digital likenesses, and why in-person entertainment might become even more valuable in an AI-saturated world. Callan and Sullivan also discuss their upcoming live comedy show, Corporate Takeover, and the creative process behind bringing corporate satire to the stage. In this episode, you’ll learn: The impact of AI on industries like acting, comedy, and digital mediaThe challenge of balancing creative ownership with AI-generated contentHow Sullivan and Callan are developing a live comedy show inspired by corporate cultureHow OpenAI’s deep research tool is reshaping competitive analysis and content preparationWhy AI-driven brand collaborations present both opportunities and ethical dilemmas for creatorsFollow Sullivan Finlay on TikTok and Instagram Follow Callan on LinkedIn Subscribe to the Newsletter

    27 min

  5. FEB 13

    Why Specialization Changes Everything

    Callan Harrington, Founder of FlashGrowth and host of That Worked, takes a deep dive into the strategic decision to niche his business into the insurance space. In this solo episode, he breaks down the fears, challenges, and long-term benefits of narrowing focus in business. If you’ve ever hesitated to specialize, this episode is packed with insights on how niching down can unlock exponential growth opportunities. In this episode, you’ll learn: The importance of industry expertise for differentiationWhy committing to a niche can accelerate word-of-mouth referralsWhy niching down feels risky but often leads to exponential growthHow segmentation and early adopters play a role in business successHow specialization simplifies decision-making and improves networking Follow Callan on LinkedIn Subscribe to the Newsletter

    16 min

  6. FEB 6

    The Power of Niching Down, Adding Instant Value, and Vulnerability in Content Creation

    In this episode of That Worked, host Callan Harrington and co-host Sullivan Finlay, a writer, comedian, and content creator, dive into the challenges and opportunities of building a career in the evolving digital landscape. They explore the vulnerability of content creation, why niching down can accelerate business growth, and how relationship-building plays a crucial role in expanding creative opportunities. Sullivan shares his insights on adapting to industry shifts, while Callan discusses adding instant value in business and the importance of strategic positioning. Together, they offer actionable advice on future-proofing careers and navigating an ever-changing digital world. In this episode, you’ll learn: How AI could redefine knowledge work and career stabilityThe power of niching down in business growth and creative careersStrategies for leveraging existing relationships to expand opportunitiesThe high-stakes TikTok bidding war and what it means for brands and creatorsHow content creators can diversify income streams and future-proof their careersFollow Sullivan Finlay on TikTok and Instagram Follow Callan on LinkedIn Subscribe to the Newsletter

    30 min

  7. JAN 30

    Sriya Maram - Co-Founder of Persana AI: The Modern GTM Stack, Prompt Engineering, and How AI is Impacting GTM

    Sriya is the Co-Founder of Persana AI. Persana AI is a Y-Combinator-backed AI tool designed to enhance sales through hyper-personalization, seamless integration, and united workflows.  Prior to Persana AI, Sriya was a Product Manager at LinkedIn.  In this episode, you’ll learn: The value of participating in hackathons.What a modern GTM tech stack looks like.  How to develop a ‘prompt engineering’ skill set. How using your own product impacts your product roadmap. How to educate, train, and inspire customers to adapt cutting edge technology.  Follow Sriya on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter

    36 min

  8. JAN 23

    Scott Knowles - Co-Founder and CEO of Deep Vector: Empathy in Sales, Selling to a Competitor, and Breaking the Rules

    Scott Knowles is the Co-Founder and CEO of Deep Vector, a web-based software platform that transforms unstructured documents into actionable insights with speed and precision.  Prior to Deep Vector, Scott was the Founder and CEO of Modgic, a software company that provided workers' compensation and mod analysis tools for the commercial insurance industry and was successfully acquired by Zywave in 2021.  In this episode, you’ll learn: The power of narrowing your focus. How innovating internally can differentiate your service model. How to test if a product is ready for you to start selling externally. When it makes sense to transition from bootstrapping to raising capital. How to approach partnerships and acquisitions with competitors without sharing sensitive information. Follow Scott on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter

    35 min
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    5
    out of 5
    16 Ratings

    About

    Host Callan Harrington breaks down the careers of top founders and executives, pulling out the key items that led to their success. These are actual career transitions, mistakes, insights, breakthroughs, and general advice that can be immediately implemented.

    Information

    • Creator
      Callan Harrington
    • Years Active
      2022 - 2025
    • Episodes
      116
    • Rating
      Explicit
    • Copyright
      © 2025 Callan Harrington
    • Show Website
      That Worked

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