Episode 17: COBRA, Health Insurance Confusion, AI in Benefits, and Building When | Andy Hamilton

19: AI, Automation & the Future of Chiropractic Care | Sherjan Husainie

Healthcare is filled with friction, paperwork, insurance headaches, and outdated systems. Sherjan Husainie looked at chiropractic care and asked a different question: What if you rebuilt the entire experience from scratch? In this episode of Life's a Pitch, Jared Gibson sits down with Sherjan Husainie, founder of KIRO, a fast-growing chiropractic company using automation, software, hospitality, and operational efficiency to modernize the chiropractic industry. KIRO operates membership-only, fully automated chiropractic studios where software powers nearly everything outside of the doctors themselves. What makes the story even more interesting is that Sherjan isn't a chiropractor. He started in aerospace engineering, became a VP at Morgan Stanley in tech investment banking across Asia, worked at Capital G (Google's late-stage investment arm), built and failed multiple startups, then walked away to build what he calls his "final company." The conversation dives into: ▪️ How KIRO is disrupting the traditional chiropractic business model ▪️ Why they eliminated insurance and simplified healthcare pricing ▪️ How AI, automation, and software improve operational efficiency ▪️ The obsession with customer experience and hospitality ▪️ Scaling a healthcare startup across New York City ▪️ Hiring, culture, and building high-performance teams ▪️ What founders learn after failed startups and career pivots ▪️ Why simplicity is often harder than complexity in business Sherjan also breaks down the realities of scaling physical healthcare locations, why quality control matters more than speed, and how KIRO plans to expand nationally while maintaining consistency across every studio. The episode also covers entrepreneurship, routines, discipline, New York City culture, consumer psychology, growth strategy, and the mindset required to survive while building a generational company. Key Takeaways: ✅ How KIRO is modernizing chiropractic care with automation and software ✅ Why removing insurance simplified the customer experience ✅ How founders scale physical businesses while protecting quality ✅ The role AI and engineering play in healthcare operations ✅ Why startup failures helped shape a stronger company ✅ The importance of customer obsession in building a brand Connect with Sherjan Husainie Guest LinkedIn: https://www.linkedin.com/in/sherjan/ [https://www.linkedin.com/in/sherjan/] Website: https://www.getkiro.com [https://www.getkiro.com] This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity. Learn more at https://www.outworks.io [https://www.outworks.io]

18. Interviewing Steve Jobs & Bill Gates, AI's Impact on Content, and Why Great Stories Matter | Rob Kelly

AI is changing content, hiring, marketing, and business faster than most people can keep up with. But long before AI became the conversation, Rob Kelly was already obsessed with storytelling, technology, and building companies around content that actually matters. In this episode of Life's a Pitch, Jared Gibson sits down with Rob Kelly, a three-time CEO and founder. Rob is currently the creator CEO of Media and the Machine, a newsletter and podcast exploring the intersection of AI & Content. The conversation starts with Rob's early journalism career, where he hustled his way into interviews with Steve Jobs, Bill Gates, and Andy Grove, including a surreal inbound phone call directly from Steve Jobs while he was building NeXT after leaving Apple. From there, the episode dives deep into: ▪️ Why AI is fundamentally changing content and agency work ▪️ The fear, optimism, and uncertainty surrounding AI adoption ▪️ How businesses should think about AI without overreacting ▪️ Why "AI plus humans" will outperform pure automation ▪️ The evolution of recruiting technology and job descriptions ▪️ How founders adapt when AI commoditizes part of their business ▪️ Why storytelling still matters more than ever Rob also shares the philosophy behind his documentary newsletter Daily Doc, his obsession with great nonfiction storytelling, and why some of the best stories in life are the ones you truly "can't make up." The episode also covers entrepreneurship, parenting, music, The Grateful Dead, creativity, content strategy, and the importance of leaving things better than you found them. Key Takeaways: ✅ What it was like interviewing Steve Jobs and Bill Gates early in their careers ✅ Why AI is disrupting agencies, content, and recruiting ✅ How founders should think about adapting instead of panicking ✅ The future of AI-powered content creation ✅ Why storytelling and human creativity still matter ✅ The mindset entrepreneurs need during massive technology shifts Connect with Rob Kelly Guest LinkedIn: https://www.linkedin.com/in/robkelly/ [https://www.linkedin.com/in/robkelly/] Podcast: Media and the Machine Company: https://www.ongig.com [https://www.ongig.com] Newsletter: DailyDoc.com This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity. Learn more at https://www.outworks.io [https://www.outworks.io]

Episode 17: COBRA, Health Insurance Confusion, AI in Benefits, and Building When | Andy Hamilton

Most companies spend a tremendous amount of time thinking about how to recruit, onboard, and retain employees. Very few spend enough time thinking about what happens when people leave. In this episode of Life's a Pitch, Jared Gibson sits down with Andy Hamilton, CEO and co-founder of When, a digital health platform helping employees navigate health insurance transitions during major life events while reducing costs for employers. Andy previously founded and scaled multiple technology companies, including ApartmentJet, which was acquired by Expedia Group. The conversation dives into the broken reality of COBRA, why healthcare decisions become overwhelming during layoffs or career transitions, and how Andy's own experience during the COVID pandemic inspired him to build When alongside his co-founders. Andy explains how most employers unintentionally create a terrible offboarding experience by treating exiting employees as "someone else's problem," despite the fact that former employees often remain on company health plans through COBRA and can dramatically increase healthcare costs. They also unpack: ▪️ Why healthcare shopping is confusing for almost everyone ▪️ How AI and concierge support work together during high-stakes decisions ▪️ The hidden costs employers overlook after layoffs and offboarding ▪️ What founders learn after raising venture capital and scaling teams ▪️ The challenge of transitioning from founder-led sales to a professional revenue organization ▪️ Why startups constantly rewrite their messaging while figuring out product-market fit ▪️ The emotional rollercoaster of entrepreneurship and learning not to get too high or too low The episode also touches on parenting, entrepreneurship, weather obsession, tennis, Claude AI, Depeche Mode, and how a founder's personal pain often becomes the foundation for building something meaningful. Key Takeaways: ✅ Why COBRA and health insurance transitions are broken for employees ✅ How employers can reduce healthcare costs through better offboarding ✅ Where AI actually helps in healthcare navigation and where humans still matter ✅ Why founder-led sales eventually needs to evolve ✅ The importance of discovery and messaging in early-stage startups ✅ How entrepreneurs learn to manage constant highs and lows Connect with Andy Hamilton Guest LinkedIn: https://www.linkedin.com/in/andyhamilton/ [https://www.linkedin.com/in/andyhamilton/] Website: https://www.4when.com [https://www.4when.com] Email: andy@4when.com [andy@4when.com] This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity. Learn more at https://www.outworks.io

16. From Homeless to Founder | Building Luster, AI Sales Enablement & Revenue Growth | Christina Brady

You hear a lot of people talk about building resilient teams and great sales processes. Very few have lived the kind of resilience it actually takes to build something from nothing. In this episode of Life's a Pitch, Jared Gibson sits down with Christina Brady, Founder of Luster, an AI-driven platform helping sales teams improve performance, eliminate revenue leaks, and make better decisions before deals go sideways. Christina shares her unconventional path into entrepreneurship, from navigating early life trauma and homelessness to becoming a sales leader and ultimately building a company designed to fix the exact problems she faced in the field. The conversation dives into the reality of sales leadership, why traditional enablement often fails, and how predictive AI is changing the way teams train, coach, and close deals. They unpack what it really means to lead without a safety net, how time and regret shape decision-making, and why most companies are reacting to problems too late instead of preventing them. The episode also explores: ▪️ How early life adversity shaped Christina's mindset as a founder ▪️ Why sales enablement is broken and treated like a cost center ▪️ The difference between reactive coaching and predictive enablement ▪️ How AI can identify revenue risk before deals are lost ▪️ The pressure and loneliness that comes with fundraising and building a team ▪️ Why great leaders hire experts and actually listen to them The conversation closes with reflections on time, purpose, and why everything in life, good or bad, has to mean something. Key Takeaways: ✅ Why resilience isn't built in business, it's built before it ✅ How predictive AI is changing sales performance and coaching ✅ The hidden cost of poor sales enablement on revenue ✅ Why founders face a different kind of pressure and loneliness ✅ How to identify and fix revenue leaks before they happen ✅ Why time is the most important resource in business and life Connect with Christina Brady: LinkedIn: https://www.linkedin.com/in/christinapbrady/ [https://www.linkedin.com/in/christinapbrady/] Email: christina@luster.ai [christina@luster.ai] Website: https://www.luster.ai [https://www.luster.ai] This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity. Learn more at https://www.outworks.io [https://www.outworks.io]

15. AI Time Tracking & Productivity Systems | How Rize Hit #1 on Product Hunt | Macgill Davis

Everyone thinks they're productive. Very few actually measure it. In this episode of Life's a Pitch, Jared Gibson sits down with Macgill Davis, founder of Rize.io, an AI-powered time tracking platform helping individuals and teams understand how they actually spend their time. Mac shares the real story behind launching Rize and hitting #1 on Product Hunt, including the months of groundwork that most people never see. From building early demand with a waitlist to validating ideas before writing a single line of code, this is a masterclass in how to launch the right way. The conversation dives into Mac's journey from startups to Twitter and back into building again, along with what he learned working alongside some of the best engineers in Silicon Valley. They also unpack how AI is changing the way companies operate and why time tracking, when done right, is becoming a critical layer for understanding productivity, profitability, and real ROI across teams. The episode also explores: ▪️ Why time tracking systems fail and how automation changes everything ▪️ How to measure whether AI tools are actually improving team performance ▪️ The rise of "Head of AI" and what that means for organizations ▪️ Why being "busy" is often a sign of inefficiency ▪️ How great founders think about building products and validating ideas The conversation closes with insights on entrepreneurship, consistency, and why success is less about big moments and more about showing up every single day. Key Takeaways: ✅ How Rize validated demand before building the product ✅ Why AI-powered time tracking is becoming essential for modern teams ✅ The real way to measure productivity and workflow efficiency ✅ How companies should think about AI implementation and ROI ✅ Why consistency beats motivation in entrepreneurship ✅ How to turn time data into better business decisions Connect with Macgill Davis: LinkedIn: https://www.linkedin.com/in/macgill-davis/ [https://www.linkedin.com/in/macgill-davis/] Website: https://rize.io [https://rize.io] This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity. Learn more at https://www.outworks.io [https://www.outworks.io]