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

22. B2B Social Media, SEO & the Future of LinkedIn | Alex Boyd

You can build a product that thousands of people love and pay for. The platform it runs on can still shut it down overnight. That is exactly what happened to Alex Boyd. In this episode of Life's a Pitch, Jared Gibson sits down with Alex Boyd, three-time founder and co-founder of DemandBird. Alex has spent the last decade building and exiting companies in B2B social and SEO. He founded RevenueZen, a B2B SEO and content marketing agency he exited to Onfolio, then built Aware, a LinkedIn engagement tool that grew to more than 1,000 paying customers before LinkedIn shut it down over its use of unofficial APIs. He's one of the most active and most honest voices in B2B social media, and one of the few people who can talk about LinkedIn without sounding like an actual LinkedIn post. Today Alex is co-founder of DemandBird, a cross-platform social media tool he launched at the end of last year. This time it's built entirely on official APIs, with a native MCP and API, so teams can draft, schedule, repurpose, and publish across LinkedIn, Twitter, Substack, Bluesky, Reddit, YouTube, and more. DemandBird is built for the agency or in-house team first, not the solo creator, aimed at the people who have outgrown clunky legacy tools like Hootsuite and Sprout Social. The conversation gets into what actually happened when LinkedIn killed Aware, how Alex rebuilt without burning everything down, and why social and SEO are quietly merging into the same game. It's an honest look at building in a space the platforms can take away from you at any moment. We also get into: ▪️ The day LinkedIn asked Alex to shut Aware down, and what he told 1,000 paying customers ▪️ Why he now builds entirely on official APIs and is rebuilding the relationship with LinkedIn ▪️ How to actually use Reddit for B2B without sounding like a bot ▪️ Why social media and SEO are merging as posts start to rank in search ▪️ Building DemandBird for agencies and teams instead of solo creators ▪️ Where social media AI agents and MCPs actually belong, and where they don't ▪️ The "stay in your lane" LinkedIn algorithm and why fighting it costs you reach ▪️ Substack, Threads, Bluesky, and where B2B attention is moving next Alex also shares his honest take on authenticity, that he isn't trying to be his whole self on LinkedIn, he's doing marketing, and why that's a healthier way to think about the platform. He gets into the grief of letting go of something he poured years into, the discipline of focusing only on what customers value most, and the one question he asks himself before every pivot. Key Takeaways ✅ Build on the platform's official rules, not around them ✅ Why SEO and social media are becoming the same channel ✅ How to use Reddit and other platforms to reach B2B buyers ✅ Why your LinkedIn content performs better when it picks one lane ✅ The smart, limited role for AI agents and MCPs in social media ✅ The 80/20 question every founder should ask about their own product Connect with Alex Boyd LinkedIn: https://www.linkedin.com/in/alexcboyd [https://www.linkedin.com/in/alexcboyd] DemandBird: https://demandbird.com [https://demandbird.com/] This episode is powered by Outworks. Outworks helps founders and executives build audience, authority, and trust through executive-led content systems that actually drive business results. Learn more at https://www.outworks.io [https://www.outworks.io/]

21. SEO, Entrepreneurship & Scaling a Digital Marketing Agency | Mark Bealin

SEO is dead. At least that's what people have been saying for the last decade. Yet companies still need leads, Google still dominates search, and businesses are still trying to figure out how AI is changing the way customers find them online. In this episode of Life's a Pitch, Jared Gibson sits down with Mark Bealin, founder of SearchLab, one of Chicago's leading digital marketing agencies. Under Mark's leadership, SearchLab has earned multiple national awards, landed on the Inc. 5000 list four consecutive years, and become a recognized leader in SEO, paid search, and digital marketing. The conversation dives into the evolution of search marketing, how AI and large language models are impacting SEO, and what business owners are getting wrong about digital visibility today. We also cover: ▪️ Building SearchLab from scratch ▪️ Finding a niche and becoming known for it ▪️ The future of SEO in an AI-driven world ▪️ Google, Gemini, and the changing search experience ▪️ Entrepreneurship, leadership, and scaling an agency ▪️ The role EO has played in Mark's personal and professional growth ▪️ Managing multiple priorities as a founder, dad, coach, and community leader ▪️ The loneliness of entrepreneurship Mark also shares lessons learned from growing a business through uncertainty, dealing with imposter syndrome, and balancing work with the things that matter most outside the office. Key Takeaways ✅ Why SEO isn't dead despite what people say ✅ How AI is changing search and digital marketing ✅ The power of niching down in business ✅ Lessons from scaling an award-winning agency ✅ Why entrepreneurship can feel lonely ✅ The importance of building a life outside of work Connect with Mark Bealin LinkedIn: https://www.linkedin.com/in/markbealin/ [https://www.linkedin.com/in/markbealin/] SearchLab: https://www.searchlabdigital.com [https://www.searchlabdigital.com] This episode is powered by Outworks. Outworks helps founders and executives build trust, authority, and audience through executive-led content systems that actually drive business results. Learn more at https://www.outworks.io [https://www.outworks.io]

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