That Worked - podcast cover

That Worked

Callan Harringtonthatworked.flashgrowth.com
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.
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Episodes

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 alignm...

Mar 13, 202543 minEp. 116

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...

Mar 06, 202521 minEp. 115

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. Tog...

Feb 27, 202523 minEp. 114

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 lik...

Feb 20, 202527 minEp. 113

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 different...

Feb 13, 202516 minEp. 112

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 ad...

Feb 06, 202530 minEp. 111

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...

Jan 30, 202536 minEp. 110

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 ...

Jan 23, 202535 minEp. 109

Dan Snyder - CEO & Co-Founder of Lower: Launching a B2C Line, Growth through Acquisition, and Building an Entrepreneurial Culture

Dan Snyder is the CEO & Co-Founder of Lower, a multi-channel home lender he helped build and grow over the last decade into the 28th largest lender in the country. Lower operates both an online direct to consumer business, and offline retail business with over 150 offices across the country. Lower raised the largest Series A in the State of Ohio ($100M) from fintech investors Accel and Sofi. Dan has also been named in the Smart 50 Class of 2022, 40 Under 40, Future 50 Class of 2021, and the ...

Jan 16, 202530 minEp. 108

Tom Grote - CEO of Agape Automation: Narrowing your Focus, Stong Values, and Balancing the Core Business and Innovation

Tom Grote is the CEO of Agape Automation, a food-tech innovation company that creates the automated Smart Kitchens of the future. Prior to Agape Automation, Tom was the COO of Donatos Pizza for over 17 years, a family-owned pizza company with more than 150 locations in six states. In this episode, you’ll learn: How narrowing in on what you’re really good at grows profits. The value of seeking out educational opportunities later in life. How to maintain a balance between operational excellence an...

Jan 09, 202531 minEp. 107

Dan Manges - Co-Founder of RWX: Finding Your Co-Founder, Engineering Challenges, and Decision Making

Dan Manges is the Co-Founder of RWX. RWX develops software engineering tools that optimize build and test performance, reliability, and developer experience. Its flagship product, Mint, is a generation newer Continuous Integration platform that gives engineers unparalleled capabilities to optimize their builds. Dan was previously the CTO of Root, a technology-powered car insurance carrier, which he co-founded in 2015 and took public via an IPO in 2020. Before Root, Dan was the CTO of Braintree, ...

Jan 02, 202547 minEp. 58

Matthew Achak - Co-Founder of FCR: Coin Flips, Choosing the Right Business Partner, and Employee Retention

Matthew Achak is the Co-Founder and Managing Partner of Non-Linear Venture Partners, where he consults and invests in early-stage start-ups. Prior to Non-Linear Venture Partners, Matt Co-Founded FCR, the leading provider of outsourced live agent support services for tech companies. FCR was acquired by TTEC in 2019. In this episode, you’ll learn: The importance of establishing a company's DNA and core values early The value of having a complementary and trustworthy business partner How to increas...

Dec 26, 202434 minEp. 78

David McFarland - Founder and CEO of Coterie Insurance: Building the Initial Team, Mitigating Hiting Mistakes, and Stage Fit

David McFarland is the Founder and CEO of Coterie Insurance. Coterie Insurance puts insurance agents and brokers first, delivering instant business insurance across the United States. Since 2018, Coterie has raised over $100M in funding and partnered with over 10,000 insurance agencies and brokerages across the country. Prior to leading Coterie, David was Chief Actuary at Clearcover, a personal auto insurtech startup in Chicago. David is also a Fellow in the Casualty Actuarial Society and has an...

Dec 19, 202438 minEp. 106

Ry Walker - Founder and CEO of Tembo: Difficult Moments, The Role of CEO, and Paying it Forward

Ry Walker is the Founder and CEO of Tembo. Tembo is the Postgres developer platform for building every data service. Their mission is to collapse the database sprawl of the modern data stack with a unified developer platform. Prior to founding Tembo, Ry was the Founder and CEO of Astronomer, which has been a huge success and has raised over 280 million dollars. In this episode, you’ll learn: How to navigate the difficulties of layoffs. The value of selling 5% of your shares during Series B. The ...

Dec 12, 202428 minEp. 105

Todd Kaufman - Co-Founder and CEO of Test Double: ESOPs, Strict Profit Margins, and Building an Ownership Mentality

Todd Kaufman is the Co-Founder and CEO of Test Double. Test Double is a software agency offering consulting services in development, product management, and infrastructure. Their experienced consultants embed with your team and help solve problems from strategy to execution. Todd has been a software engineer for over 25 years, focusing on building systems that deliver business value and scale without excessive costs. Prior to Test Double, Todd worked as a Vice President at Pillar Technology. In ...

Dec 05, 202444 minEp. 104

Joe Apgar - CEO of PELOTONIA: Surviving Cancer, Sharing Your Story, and the Power of Family and Friends

Joe Apgar is the CEO of PELOTONIA, which was established in 2008 to fund lifesaving cancer research and is a rapidly growing non-profit today. Before PELOTONIA, Joe worked eight years at Rockbridge Capital. He was named to the 40 Under 40 Class of 2020 by Columbus Business First and the Future 50 Class of 2021 by Columbus CEO Magazine. In 2022, he was selected as a member of the Young American Leaders Program at Harvard Business School. In this episode, you’ll learn: The healing power of writing...

Nov 28, 202457 minEp. 104

Maddie Bell - Co-Founder and CEO of Scheduler AI: Driving Habit Change, Using Your Own Product, and Big Idea Thinking

Maddie Bell is the Co-Founder and CEO of Scheduler AI, an AI appointment setter that integrates directly into your CRM, web forms, and chats to coordinate meeting times in seconds while safeguarding your show rates. Prior to Scheduler AI, Maddie was a Brand Director for Procter & Gamble. While at P&G, she spent 12 years leading and delivering topline, bottom line, and share growth for multiple billion-dollar brands and products. In this episode, you’ll learn: How to measure if an innovat...

Nov 21, 202441 minEp. 103

Aaron Crookes - Co-Founder & CEO of Apricity Robotics: Picking the Right Product for Your Market, Balancing Product Development vs. Business Building, and Strategic vs. Generalist Investors

Aaron Crookes is the Co-Founder and CEO of Apricity Robotics, a startup focused on developing semi-autonomous robots to aid and assist both patients and healthcare staff. Their main goal is to automate simple tasks so healthcare staff can be fully dedicated to critical patient needs. Prior to Apricity Robotics, Aaron worked in R&D for Autonomous Robots and Devices at Proctor and Gamble. In this episode, you’ll learn: How to balance building the product with building the business. When it’s n...

Nov 14, 202436 minEp. 102

Amanda Epp - CEO at ScriptDrop: Creating a Network Effect, Building a Customer Flywheel, and Being Your Authentic Self as CEO

Amanda Epp is a founding team member and the CEO of ScriptDrop. ScriptDrop is the only healthcare IT company specializing in medication access that serves patients in all 50 states. ScriptDrop works alongside its healthcare partners to deliver medication access opportunities through technology, empathy, and healthcare expertise. Previously, Amanda was an early employee of CoverMyMeds, moving up the ranks to ultimately serve as Director of New Product Implementation. She played an integral role i...

Nov 07, 202441 minEp. 101

Genevieve Bellaire - Founder & CEO of Realworld: Transitioning from B2B to B2C, Launching a Zero to One Product, and Creating a Category

Genevieve Bellaire is the Founder and CEO of Realworld. Realworld is your companion for navigating the journey of adulthood. They help you "get it together" by simplifying and streamlining your finances, health, career, and household. Prior to Realworld, Genevieve received her JD and MBA from Georgetown University and spent time at Goldman Sachs before ultimately launching Realword. In this episode, you’ll learn: How to build your MVP as a non-technical founder How to transition a B2B business t...

Oct 31, 202437 minEp. 100

Brian Gregory - Co-Founder and CEO of FMX: Waiting to Raise Capital, CEO Transitions, and Going Outbound

Brian Gregory is the Co-Founder and CEO of FMX. FMX is a leading provider of purpose-built, cloud-based solutions for Public Sector organizations. They help their customers transform facility, maintenance, and operations management in the communities where everyone learns, works, and lives. Before founding FMX, Brian was a partner at Dynamix Energy Services, managing energy savings projects that highlighted the critical role of proper facilities management, ultimately inspiring the creation of F...

Oct 24, 202443 minEp. 99

Lindsay Fork - Founder & CEO of Luxe Brands: Turning Challenges into New Businesses, Filtering Opportunities, and EOS

Lindsay Fork is the Founder and CEO of Luxe Brands. Luxe Brands is a bridal fashion company with multiline offerings + brands for all brides. From La Jeune Mariee Bridal Collection, a luxury designer and special-order boutique located in downtown Columbus, Ohio, to "luxury for less" with multiunit Luxe Redux, the company caters to serve all brides. Lindsay recently won the Ernst and Young Entrepreneur of the Year Award for the East Central Region. In this episode, you’ll learn: The importance of...

Oct 17, 202442 minEp. 98

Chris Powell - CEO of Talmetrix: Red Pill Moments, Going from Corporate to Startup, and Channel Partnerships

Chris Powell is the CEO of Talmetrix, an employee feedback and analytics company with a mission to humanize data to further workplace well-being. Leading up to Talmetrix, Chris built a career in human resources, including working as the Chief Human Resources Officer for Scripps Networks Interactive. In this episode, you’ll learn: How to capitlize on “red pill or blue pill” moments The strategic value of combining software with service The importance of identifying the right data points in human ...

Oct 10, 202438 minEp. 97

Tsavo Knott - Co-Founder and CEO of Pieces: Building a Community, Trusting your Gut, and Company Events

Tsavo is the CEO and Co-Founder of Pieces, a suite of on-device developer tools that boost productivity by helping you solve complex development tasks through a contextual understanding of your entire workflow. Tsavo was an entrepreneur from the jump, founding his first company, accent.ai, straight out of high school. In this episode, you’ll learn: How to balance gut instinct with market feedback The importance of elevating your EQ to put together top-tier teams How to reach developers in the sa...

Oct 03, 202434 minEp. 96

Exploring 10X Goals, Navigating Creativity, Content Optimization, and Delegation Strategies

Callan Harrington is the founder of Flashgrowth, and today, he is joined by Sullivan Finlay, a comedian and content creator based in Chicago. Sullivan has built a successful following on social media through engaging, humorous, and relatable content. In this episode of "That Worked," Callan and Sullivan dive into topics ranging from emerging healthcare models to the future of local news, technology, and how both guests are leveraging strategic thinking for growth. In this episode, you’ll learn: ...

Sep 26, 202433 minEp. 95

Katie Trauth Taylor - Co-Founder & CEO at Narratize AI: AI-Driven Storytelling, Scaling Innovation, and Creating Serendipity

Katie Trauth Taylor is the CEO and Co-Founder of Narratize AI, a Generative AI storytelling platform for innovative enterprises. Before Narratize AI, Katie received her PhD in Rhetoric and Composition. During her PhD program, she launched her first startup, Untold Content. She is also the host of the Untold Stories of Innovation podcast. In this episode, you’ll learn: How to capitalize on referrals to outpace competitors. The most impactful incentives for brand ambassadors. How to build a connec...

Sep 19, 202445 minEp. 94

Jane Mosbacher Morris - Founder and CEO of TO THE MARKET: Change Management, Using Capitalism to Make an Impact, and Thought Leadership

Jane Mosbacher Morris is the CEO of To The Market. To The Market is a turn-key solution for ethical manufacturing and sourcing of apparel, accessories, and home goods. Before To The Market, Jane was the Director of Humanitarian Action for the McCain Institute and a Counterterrorism Advisor for the U.S. State Department. She is also the author of Buy The Change You Want to See, a book that explores how you can have a greater social impact through your everyday purchases. In this episode, you’ll l...

Sep 12, 202436 minEp. 93

Brock Leonti - CEO & Co-Founder of Prescribe FIT: Turning Passion into a Business, Solving Staffing Challenges, and Managing Stress

Brock Leonti is the CEO & Co-Founder of Prescribe FIT. Prescribe FIT is a full-service remote monitoring and lifestyle health coaching solution designed for orthopedic practices and patients. Prior to Prescribe FIT, Brock was the Founder of Larock Healthcare Academy, which was acquired by Beckfield College, and President & Founder of Time For Help Home Care. In this episode, you’ll learn: The importance of using your PTO. A solution to industry-wide staffing shortages. How to identify wh...

Sep 05, 202428 minEp. 92

Darrin Murriner - Co-Founder & CEO of Cloverleaf: Rejection, Resilience, and Building a Winning Team

Darrin Murriner is the Co-Founder and CEO of Cloverleaf. Cloverleaf is an identity discovery and team-building tool that uses the most common behavioral assessments to help you discover how to work more effectively as a team or as an individual in a team. Prior to Cloverleaf, Darrin co-founded BabysitEase. He is also the author of Corporate Bravery, a book about eliminating fear-based decision-making and transforming corporate cultures into brave places for people to do their best work and stay ...

Aug 29, 202434 minEp. 91

Tim Metzner - Founder & CEO at Fireroad: Nurturing Your Culture, Retaining Top Talent, and Leaps of Faith

Tim Metzner is the Founder and CEO of Fireroad. Fireroad is a new kind of holding company, borrowing the best from venture studios and private equity models. They bring a balanced approach to managing the risk of early-stage ventures with the predictability of enduringly profitable businesses. Prior to Fireroad, Tim was a Founder of Ocean Accelerator, Differential, and Coterie Insurance. He’s also an active angel investor in 56 deals. In this episode, you’ll learn: How to nurture a great culture...

Aug 22, 202433 minEp. 90
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