Life's a Pitch with Jared Gibson

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 an...

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 bargainin...

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,...

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...

Healthcare is filled with friction, paperwork, insurance headaches, and outdated systems.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, an...

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 CE...

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 wh...

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 befor...

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 mo...

A lot of people talk about impact. Very few actually build their life around it. In this episode of Life's a Pitch, Jared Gibson sits down with Brian Floriani, entrepreneur, founder of Bernie's Book Bank, and co-founder of Buku Branded. Brian shares the story behind launching Bernie's Book Bank out of his garage after a life-changing personal loss, and how it has grown into an organization that ha...

Too many B2B companies are still treating content like a nice-to-have. The ones that get it have turned content into a system that actually drives revenue. In this episode of Life's a Pitch, Jared Gibson sits down with Alex Sheridan, Founder of Impaxs and Podcast Builders, to break down what's actually working in B2B content right now. Alex has spent over a decade in B2B sales and marketing, helpi...

Most entrepreneurs think growth gets easier once things start working. It doesn't. The problems just change. In this episode of Life's a Pitch , Jared Gibson sits down with Karl Hughes , founder of draft.dev , a niche content agency focused on technical audiences, and owner of The Podcast Consultant . Karl started his career leading engineering teams at venture-backed startups before launching dra...

Most leaders feel like they're behind on AI. The reality is… everyone is trying to figure it out in real time. In this episode of Life's a Pitch, Jared Gibson sits down with Dan Levin, Co-Founder and President of Liventus, a technology company that has been helping businesses modernize systems, automate workflows, and make better decisions since 2002. Dan shares how Liventus evolved from a custom...

Most leaders think they're communicating clearly. Very few actually are. In this episode of Life's a Pitch , Jared Gibson sits down with Rob Johnson , a multiple Emmy award winning former Chicago TV news anchor who spent more than two decades on air at ABC and CBS. Today, Rob runs Rob Johnson Communications , where he works with executives, founders, and leadership teams to sharpen their messaging...

Most sales teams say they want better pipeline. What they actually need is better attention and a business that is not run on fake urgency, Slack dopamine, and pressure tactics. In this episode of Life's a Pitch, Jared Gibson sits down with Leslie Venetz, one of the most influential voices in modern sales. Leslie's content has been viewed more than 100 million times, she has been featured in The W...

Most revenue leaders talk about discipline, standards, and accountability. Very few actually build cultures around it and live it every day. In this episode of Life's a Pitch, Jared Gibson sits down with Larry Seiler, SVP of Revenue at Spyglass, a specialized technology advisory firm. Larry leads and scales high-performing sales teams while helping mid-sized and enterprise organizations reduce tel...

Most B2B founders want to scale revenue, but they still run sales like the company cannot close a deal unless the founder is involved in every conversation. In this episode of Life's a Pitch, Jared Gibson sits down with Alex Newmann, founder and CEO of Newmann Consulting Group. Alex helps B2B founders transition out of founder-led sales and build scalable, repeatable sales systems that drive predi...

A lot of companies struggle to explain what they actually do, even when they're good at it. This episode of Life's a Pitch with Aimee Schuster digs into that exact problem. Aimee is a founder and marketing leader who works with B2B companies, often in professional services and SaaS, helping them clarify their message, rebuild their marketing systems, and scale growth in a way that actually matches...

Most agency owners say they want predictable growth, but they still run their business like it's powered by luck, referrals, and a few warm intros that may or may not show up. In this episode of Life's a Pitch, Jared Gibson sits down with Chris DuBois, founder of the Dynamic Agency Operating System. Chris helps agency owners break referral dependence, stop duct taping their business together, and...

Most founders know they need a go-to-market strategy, but very few understand when founder-led selling should evolve into a real revenue engine, or how personal brand fits into that transition. In this episode of Life's a Pitch, Jared Gibson sits down with Jess Schultz, founder of Amplify Group, fractional CRO and CMO, former venture capitalist, and active angel investor. Jess works with B2B start...

Most professionals talk about reinvention, but very few actually do it without burning bridges, blowing up their identity, or chasing the next shiny thing. In this episode of Life's a Pitch, Jared Gibson sits down with James Hornick, former Chief Growth Officer at Hirewell and now an independent options trader specializing in systematic zero DTE strategies. James shares what it really looks like t...

In this episode of Life's a Pitch, I sit down with Jen Guzman, founder of Bestola Consulting and one of the most no-BS operators in Chicago's small and mid-market business scene. Jen and I go back to our days working together in HR/marketing during the early COVID chaos, so we start with real stories about urgency, leadership under pressure, and what it looks like to serve clients when everything...

In this episode of Life's a Pitch, I sit down with John Tsourakis, co-owner of digital agency OYOVA and a multi-time founder who has built, scaled, and exited businesses across agencies, healthcare, and tech. We get into what it really looks like to run an agency today, why the model is tough, where founders get it wrong, and how acquisitions and focus can create leverage instead of more chaos. Jo...