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

That Worked

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26:28

Squid Game is back—and this time, the knives are out. In the thrilling Season 3 premiere, Player 456 is spiraling and a brutal round of hide-and-seek forces players to kill or be killed. Hosts Phil Yu and Kiera Please break down Gi-hun’s descent into vengeance, Guard 011’s daring betrayal of the Game, and the shocking moment players are forced to choose between murdering their friends… or dying. Then, Carlos Juico and Gavin Ruta from the Jumpers Jump podcast join us to unpack their wild theories for the season. Plus, Phil and Kiera face off in a high-stakes round of “Hot Sweet Potato.” SPOILER ALERT! Make sure you watch Squid Game Season 3 Episode 1 before listening on. Play one last time. IG - @SquidGameNetflix X (f.k.a. Twitter) - @SquidGame Check out more from Phil Yu @angryasianman , Kiera Please @kieraplease and the Jumpers Jump podcast Listen to more from Netflix Podcasts . Squid Game: The Official Podcast is produced by Netflix and The Mash-Up Americans.…

about a year ago 30:22

MP3•Episode home

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 stability
The power of niching down in business growth and creative careers
Strategies for leveraging existing relationships to expand opportunities
The high-stakes TikTok bidding war and what it means for brands and creators
How content creators can diversify income streams and future-proof their careers

Follow Sullivan Finlay on TikTok and Instagram

Follow Callan on LinkedIn

116 episodes

#Careers #Entrepreneur #Business #Callan Harrington

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

That Worked

published about a year ago

MP3•Episode home

In this episode, you’ll learn:

How AI could redefine knowledge work and career stability
The power of niching down in business growth and creative careers
Strategies for leveraging existing relationships to expand opportunities
The high-stakes TikTok bidding war and what it means for brands and creators
How content creators can diversify income streams and future-proof their careers

Follow Sullivan Finlay on TikTok and Instagram

Follow Callan on LinkedIn

Subscribe to the Newsletter

116 episodes

#Careers #Entrepreneur #Business #Callan Harrington

All episodes

1
Matt Farrell - COO at Niobium Microsystems: Succeeding in the Earliest Stages, Evaluating Potential Employees, and Creating Work/Life Alignment 43:05

16 weeks ago43:05

43:05

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 startups How to evaluate potential employees What 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…

1
Mastering Content Strategy, Delegation, and Creative Efficiency 20:51

18 weeks ago20:51

20:51

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 outsourcing Why repurposing content can supercharge engagement How to leverage visual planning tools for content creation The importance of structured ideation and content pipelines The 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…

1
The Power of Improv, AI-Driven Content, and Buying Back Time for Growth 23:28

19 weeks ago23:28

23:28

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…

1
The Ethics of AI, Digital Likenesses, and the Future of Content Creation 26:39

20 weeks ago26:39

26:39

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 media The challenge of balancing creative ownership with AI-generated content How Sullivan and Callan are developing a live comedy show inspired by corporate culture How OpenAI’s deep research tool is reshaping competitive analysis and content preparation Why AI-driven brand collaborations present both opportunities and ethical dilemmas for creators Follow Sullivan Finlay on TikTok and Instagram Follow Callan on LinkedIn Subscribe to the Newsletter…

1
Why Specialization Changes Everything 16:21

21 weeks ago16:21

16:21

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 differentiation Why committing to a niche can accelerate word-of-mouth referrals Why niching down feels risky but often leads to exponential growth How segmentation and early adopters play a role in business success How specialization simplifies decision-making and improves networking Follow Callan on LinkedIn Subscribe to the Newsletter…

1
The Power of Niching Down, Adding Instant Value, and Vulnerability in Content Creation 30:22

22 weeks ago30:22

30:22

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 stability The power of niching down in business growth and creative careers Strategies for leveraging existing relationships to expand opportunities The high-stakes TikTok bidding war and what it means for brands and creators How content creators can diversify income streams and future-proof their careers Follow Sullivan Finlay on TikTok and Instagram Follow Callan on LinkedIn Subscribe to the Newsletter…

1
Sriya Maram - Co-Founder of Persana AI: The Modern GTM Stack, Prompt Engineering, and How AI is Impacting GTM 36:23

22 weeks ago36:23

36:23

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…

1
Scott Knowles - Co-Founder and CEO of Deep Vector: Empathy in Sales, Selling to a Competitor, and Breaking the Rules 34:48

24 weeks ago34:48

34:48

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…

1
Dan Snyder - CEO & Co-Founder of Lower: Launching a B2C Line, Growth through Acquisition, and Building an Entrepreneurial Culture 30:11

25 weeks ago30:11

30:11

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 #4 CEO by Glassdoor. In this episode, you’ll learn: How to adapt from a B2B to B2C mindset. When to acquire externally versus build internally. How an entrepreneurial culture empowers high performers. How to grow market share in a down market through acquisition. How avoiding over-accommodating a seller in an acquisition leads to long-term success. Follow Dan on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter…

1
Tom Grote - CEO of Agape Automation: Narrowing your Focus, Stong Values, and Balancing the Core Business and Innovation 31:05

26 weeks ago31:05

31:05

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 and innovation. How to build a business grounded in courage, empathy, and doing the right thing. The importance of surrounding yourself with a diverse team with complementary skills. Follow Tom on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter…

1
Dan Manges - Co-Founder of RWX: Finding Your Co-Founder, Engineering Challenges, and Decision Making 47:24

27 weeks ago47:24

47:24

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, where he built a payments platform that PayPal acquired in 2013 for $800M. In this episode, you’ll learn: The unique challenges engineers face What to look for in a technical co-founder What to look for in a non-technical co-founder The benefits of assigning a mentor to new employees Why you need to focus on the problems you’re having now Follow Dan on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter…

1
Matthew Achak - Co-Founder of FCR: Coin Flips, Choosing the Right Business Partner, and Employee Retention 34:11

28 weeks ago34:11

34:11

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 increase your employee retention rate in a high attrition business Strategies for leveraging small communities to build a successful business How taking chances and learning new things can help you find your calling Follow Matthew on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter…

1
David McFarland - Founder and CEO of Coterie Insurance: Building the Initial Team, Mitigating Hiting Mistakes, and Stage Fit 37:33

29 weeks ago37:33

37:33

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 extensive background in creating and managing insurance programs. In this episode, you’ll learn: How to evaluate a potential co-founder. How to structure a consult-to-hire team before raising capital. How robust data collection can help you stand out from the competition. How a strong and quick offboarding process can mitigate hiring mistakes. How to ensure you have the right team members for the current stage of your business. Follow David on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter…

1
Ry Walker - Founder and CEO of Tembo: Difficult Moments, The Role of CEO, and Paying it Forward 28:03

30 weeks ago28:03

28:03

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 importance of letting your team review you as a CEO. How to build strong leaders through clear expectations of roles. The importance of paying it forward within your entrepreneur community. Follow Ry on LinkedIn Connect Follow Callan on LinkedIn Subscribe to the Newsletter…

1
Todd Kaufman - Co-Founder and CEO of Test Double: ESOPs, Strict Profit Margins, and Building an Ownership Mentality 43:54

31 weeks ago43:54