Life's a Pitch with Jared Gibson

Jared Gibson
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Life's a Pitch is a podcast where founders and executives drop the polish and get real. No filters, no perfect stories. Just raw conversations about the chaos of building companies, the struggles that come with it, and the messy life that happens outside of work. It is part therapy, part comedy, and part truth serum with curveballs, sarcasm, and plenty of laughs. Because life is not balanced, work is not polished, and honestly… Life's a Pitch.

  1. Aug 5

    26. Hiring Global Talent, SDRs & Building Remote Teams | Jason Lalk

    Hiring great people has never been harder. At the same time, founders have access to more global talent than ever before. So how do you build high-performing remote teams without sacrificing quality? In this episode of Life's a Pitch, Jared Gibson sits down with Jason Lalk, founder of Remote Growth Partners, a company that helps businesses hire, train, and manage overseas sales and marketing professionals. Before launching RGP, Jason was the first employee at CloserIQ, where he helped build one of the top startup recruiting firms in the country. As both a client and a friend, Jared shares firsthand how Remote Growth Partners has helped Outworks build an incredible team over the past several years. The conversation dives into remote hiring, SDRs, AI, cold calling, entrepreneurship, content strategy, and what founders often get wrong when building teams. We also cover: ▪️ How to hire exceptional overseas SDRs and marketers ▪️ Why cold calling still outperforms most outbound channels ▪️ AI's impact on hiring and remote work ▪️ The biggest hiring mistakes founders make ▪️ Building intentional interview processes that actually predict success ▪️ Why niching down creates stronger businesses ▪️ Growing a company through referrals and LinkedIn content ▪️ Lessons from building Remote Growth Partners Jason also shares stories from Augusta National, why operational excellence matters at every level, balancing entrepreneurship with family, and why "intentionality" has become one of his guiding principles. Key Takeaways ✅ Why global hiring is becoming a competitive advantage ✅ How to interview candidates more effectively ✅ Why cold calling is far from dead ✅ What AI means for recruiting and remote teams ✅ Building a sustainable content strategy as a founder ✅ The value of being intentional in business and life Connect with Jason Lalk LinkedIn: https://www.linkedin.com/in/jasonlalk/ Remote Growth Partners: https://www.remotegrowthpartners.com This episode is powered by Outworks. Outworks helps founders and executives build authority through executive-led content that creates trust long before the first sales conversation. Learn more at https://www.outworks.io

  2. Jul 15

    25. Entrepreneurship, AI & Association Innovation | Dave Will

    *]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id= "request-6968e12e-f610-8333-9786-a673cbc23b1f-0" data-turn-id-container= "request-6968e12e-f610-8333-9786-a673cbc23b1f-0" data-testid= "conversation-turn-250" data-turn="assistant"> What if the voice in your head telling you that you got lucky...never goes away? For Dave Will, that's been one of the biggest drivers behind building multiple successful companies. In this episode of Life's a Pitch, Jared Gibson sits down with Dave Will, founder of PropFuel, an AI-powered member engagement platform built specifically for trade associations and professional societies. Before PropFuel, Dave built and sold a software company, only to discover that success didn't quiet the little voice telling him he needed to prove he could do it again. The conversation explores entrepreneurship, AI, product market fit, leadership, persistence, and what it actually feels like after selling a company. We also get into: ▪️ Why persistence beats intelligence over the long run ▪️ The "little voice" every entrepreneur battles ▪️ Building PropFuel and the future of AI for associations ▪️ Product market fit and why founders often chase the wrong problems ▪️ How AI is changing SaaS and software development ▪️ Why niching down creates better businesses ▪️ The loneliness of entrepreneurship ▪️ Running marathons, Ironmans, sailing, and why endurance teaches better business lessons than almost anything else Dave also shares the story behind selling his first company, what it felt like when the wire finally hit his bank account, and why he still felt the need to start over from scratch. One lesson that stuck with me was his personal philosophy: Walk slow. Smile more. Simple advice that says a lot about how he approaches business, leadership, and life. Key Takeaways ✅ Why persistence matters more than raw talent ✅ The importance of finding true product market fit ✅ How AI is reshaping SaaS and associations ✅ What really happens after selling a company ✅ Why niching down accelerates growth ✅ The entrepreneurial mindset behind building businesses that last Connect with Dave Will LinkedIn: https://www.linkedin.com/in/davidrwill/ PropFuel: https://www.propfuel.com EO 360 Podcast: https://eopodcasts.org/  This episode is powered by Outworks. Outworks helps founders and executives build authority through executive-led content that creates trust long before the first sales conversation. Learn more at https://www.outworks.io

    25. Entrepreneurship, AI & Association Innovation | Dave Will

  3. Jul 9

    24. Relationship Selling, Restaurant Growth & Building Premier Payroll Solutions | Michael D'Onofrio

    Everyone talks about scaling a business. Michael D'Onofrio built one by focusing on something much simpler: relationships. In this episode of Life's a Pitch, Jared Gibson sits down with Michael D'Onofrio, Managing Partner of Premier Payroll Solutions, to discuss his journey from selling pet food and medical devices to building one of the fastest-growing payroll companies serving the restaurant and hospitality industry. Instead of relying on aggressive sales tactics, Michael built Premier Payroll Solutions through trust, referrals, and genuine relationships. Today, the company serves nearly 2,000 businesses across more than 40 states with a team of 30+ employees. The conversation covers entrepreneurship, sales, leadership, company culture, and why relationships continue to outperform transactions. We also get into: ▪️ Why relationship selling beats traditional cold calling ▪️ Building Premier Payroll Solutions from a simple idea on a napkin ▪️ Lessons from leaving medical device sales to start a business ▪️ Growing organically through referrals and trust ▪️ How the restaurant industry navigated COVID-19 ▪️ Building a company culture people actually want to be part of ▪️ Why hospitality is the foundation of great customer service ▪️ How Michael and his partners use podcasting to build relationships instead of chasing leads Michael also shares one of the most emotional moments of his entrepreneurial journey during the pandemic, why he believes investing in people always pays the greatest return, and the advice that shaped his entire career: "Don't do a good job. Do a great job." Key Takeaways ✅ Why relationships remain the greatest competitive advantage in business ✅ How Premier Payroll Solutions grew almost entirely through referrals ✅ The power of niching into the restaurant and hospitality industry ✅ Leadership lessons from navigating COVID-19 ✅ Why culture matters more than perks ✅ How podcasting can become one of the best business development tools available Connect with Michael D'Onofrio LinkedIn: https://www.linkedin.com/in/michael-d-onofrio-176b0122/ Premier Payroll Solutions: https://www.premierpayrollny.com Staying Hungry Podcast: https://www.youtube.com/@StayingHungryPodcast This episode is powered by Outworks. Outworks helps founders and executives build authority through executive-led content that creates trust before the first sales conversation. Learn more at https://www.outworks.io

    24. Relationship Selling, Restaurant Growth & Building Premier Payroll Solutions | Michael D'Onofrio

  4. Jun 25

    23. Collective Bargaining Software, Founder-Led Sales & Selling to Schools | Michael Mastrullo

    School boards negotiate hundred-million-dollar budgets with volunteers and almost no data. Michael Mastrullo spent 20 years inside public schools watching it happen. Then he built the fix. In this episode of Life's a Pitch, Jared Gibson sits down with Michael Mastrullo, co-founder and CEO of Litix, a SaaS platform that gives K-12 school districts and municipalities data-driven collective bargaining analytics and compliance training. Before Litix, Michael spent 20 years in public education, 16 of them as a high school principal running budgets and sitting at the bargaining table. Before that, he worked fixed income sales at Merrill Lynch and was drafted out of high school as a professional baseball player in the Cleveland Indians organization. Today he's building Litix from the operator seat. Litix Insights brings real salary benchmarking, settlement forecasting, and budget modeling to labor negotiations that used to run on spreadsheets and emotion, and Litix Academy turns mandatory state and federal training into something people will actually sit through. The company works with 85% of Massachusetts school districts, partners with more than 300 districts and municipalities, and holds a 97% retention rate, mostly off word of mouth and founder-led sales. The conversation covers what it really takes to sell into the public sector, why your network gets you a meeting and nothing more, and how a guy with no formal sales training built a category with no real competitor. We also get into: ▪️ Why people don't buy data platforms, they buy 50 hours of their life back ▪️ Selling into school districts and municipalities, and the wall every vendor hits ▪️ Building from an embarrassing MVP you pray doesn't break in the demo ▪️ Landing the Massachusetts superintendents endorsement that changed everything ▪️ Why a 97% retention rate comes from doing things that don't scale ▪️ Hiring when you're small and can't afford to miss ▪️ Walking away from a great job, a top salary, and a pension to go all in ▪️ Why the baseball "failure" was the best thing that ever happened to him Michael also shares the human side most founders edit out. The one panic attack that pulled him out of law school orientation. Tearing his labrum and the day his career ended. Reframing a decade of feeling like a failure once he had kids. Caring for his father while building a company. And what it actually feels like to walk away from security when everyone around you thinks you're crazy. Key Takeaways ✅ Your network opens the door, it does not guarantee the meeting or the deal ✅ Stop selling the platform, sell the problem you've personally felt ✅ Hyper-responsiveness and unscalable service are a real competitive moat ✅ A third-party endorsement won't close the deal, but it gets you the look ✅ Hiring is the highest-leverage decision a small company makes ✅ No job is too small, and hard work covers a lot of gaps Connect with Michael Mastrullo LinkedIn: https://www.linkedin.com/in/michael-mastrullo-0338a3153 Litix: https://litix.ai 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

    23. Collective Bargaining Software, Founder-Led Sales & Selling to Schools | Michael Mastrullo

  5. Jun 17

    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 DemandBird: 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

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

  6. Jun 10

    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/  SearchLab: 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

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

  7. Jun 2

    20: PropTech, EV Charging & Building 3 Startups at Once

    Life's a Pitch with Jared Gibson

  8. May 21

    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/  Website: 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

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About

Life's a Pitch is a podcast where founders and executives drop the polish and get real. No filters, no perfect stories. Just raw conversations about the chaos of building companies, the struggles that come with it, and the messy life that happens outside of work. It is part therapy, part comedy, and part truth serum with curveballs, sarcasm, and plenty of laughs. Because life is not balanced, work is not polished, and honestly… Life's a Pitch.

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