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/ Website: https://www.4when.com Email: [email protected]

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

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.

✅ 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

LinkedIn: https://www.linkedin.com/in/christinapbrady/ Email: [email protected] Website: https://www.luster.ai

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

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.

✅ 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

LinkedIn: https://www.linkedin.com/in/macgill-davis/ Website: 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

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 has distributed tens of millions of books to children in under-resourced communities.

The conversation goes deeper than the origin story. Brian breaks down how his mindset shifted from chasing success to choosing significance, and why that decision changed everything about how he approaches business, relationships, and life.

They also unpack how Buku Branded was built as a purpose-driven company that redirects marketing dollars toward literacy, creating a model where business growth and impact are directly connected.

The episode also explores:

▪️ The real story behind starting Bernie's Book Bank ▪️ Why book ownership is critical to childhood literacy ▪️ The difference between success and significance ▪️ Why "networking" is the wrong way to build relationships ▪️ The power of giving first without an agenda ▪️ Early sales lessons and overcoming call reluctance ▪️ How purpose-driven businesses can scale impact

The conversation closes with reflections on legacy, relationships, and the idea that the only thing you leave behind is the impact you make on others.

✅ Why significance matters more than success ✅ How one decision can completely change your life's direction ✅ The importance of literacy in long-term outcomes ✅ Why giving first creates stronger relationships ✅ How to think about business as a vehicle for impact ✅ What most people get wrong about networking and sales

Guest LinkedIn: https://www.linkedin.com/in/brianfloriani/ Email: [email protected] Bernie's Book Bank: https://www.berniesbookbank.org Buku Branded: https://www.bukubranded.com

Outworks helps B2B companies build real, repeatable executive content engines through executive-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.

Learn more at https://www.outworks.io

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, helping companies build content systems that generate trust, pipeline, and real business results. His approach is simple but not easy: content should not just create awareness, it should create demand.

The conversation dives into why video is still massively underutilized in B2B, what's really holding people back from creating it, and how companies can shift from random posting to building a repeatable content engine.

They also unpack the difference between content that looks good and content that actually performs, and why most companies fail before they ever give it a real shot.

The episode also explores:

▪️ Why most people quit video content way too early ▪️ The real reason leaders avoid creating content (it's not strategy) ▪️ How to build trust faster using video vs text ▪️ Why LinkedIn reach is down and what to do about it ▪️ The difference between predictive vs non-predictive lead generation ▪️ Why podcasting is becoming one of the most powerful B2B growth channels

The conversation also touches on what it actually takes to build a content-driven business over time, including the mindset shift required, the discipline most companies lack, and how Alex built a system that turns conversations into pipeline.

Key Takeaways:

✅ Why content needs to be tied directly to revenue, not just awareness ✅ How video builds trust faster than any other format ✅ The biggest mistake companies make when starting content ✅ How to think about LinkedIn, YouTube, and podcasts strategically ✅ Why most marketing fails without the right internal mindset ✅ How to build a content system that compounds over time

Connect with Alex Sheridan LinkedIn: https://www.linkedin.com/in/alexsheridan Website: https://www.impaxs.com

This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through executive-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.

Learn more at https://www.outworks.io

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 draft.dev in 2020 and scaling it to more than $2.5M in ARR in just two years.

Karl shares what it actually looks like to build a service business, step out of the day to day, and then start buying businesses instead of only building them. The conversation also gets into a more personal side of entrepreneurship, including his sobriety journey, how discipline plays into everything he does, and why avoiding hard things usually slows you down more than it helps.

They also get into content, why attribution on LinkedIn is still messy, and why that doesn't mean it isn't working. Karl breaks down how compounding channels actually drive pipeline over time, even when you can't point to one post and say "that closed the deal."

The episode also covers:

• Why sobriety changed how Karl operates as a founder • How draft.dev scaled to $2.5M+ ARR • Why content works even when attribution doesn't make sense • What to look for when buying a service business • Why niche agencies win more often than generalists • The real challenges of running multiple businesses at once

The conversation closes on something most founders don't talk about enough. No matter how big the company gets, the uncertainty doesn't go away. You just get better at dealing with it.

✅ Why discipline and sobriety can improve decision-making ✅ How to scale a niche agency quickly ✅ Why LinkedIn content is a long game ✅ What most founders miss about acquisitions ✅ Why specialization creates leverage ✅ How to think about growth plateaus

LinkedIn: https://www.linkedin.com/in/karllhughes/ Website: https://draft.dev Podcast: https://www.retainedtrust.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

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 software firm into an AI-forward automation company, and what business leaders should actually be focusing on as AI continues to reshape industries.

The conversation covers everything from building a company over two decades to navigating uncertainty in AI, hiring the right people, and why a true partnership mindset still wins in business.

The episode explores:

▪️ How Liventus helps companies modernize legacy systems and automate workflows ▪️ Why a problem-solving mindset beats short-term revenue thinking ▪️ The difference between being a vendor vs. a true partner ▪️ Why hiring the right people is the hardest and most important part of business ▪️ How AI is impacting decision-making, operations, and efficiency today ▪️ Why most leaders feel behind on AI and what to actually do about it ▪️ The reality behind AI hype vs. what is actually happening in business

Key Takeaways

✅ Why focusing on solving real problems leads to long-term growth ✅ How to think about AI without getting lost in hype or fear ✅ Why education and experimentation with AI is no longer optional ✅ The importance of partnership over transactional relationships ✅ How automation and data can drive faster, smarter decisions ✅ Why great businesses are built on great people, not just strategy

Connect with Dan Levin Website: https://www.liventus.com Email: [email protected]

This episode is powered by Outworks.

Outworks helps B2B companies build real, repeatable executive content engines through executive-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.

Learn more at https://www.outworks.io

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, communicate with confidence, and connect when the stakes are highest.

Rob shares how his career in broadcast journalism shaped the way he thinks about leadership communication. From interviewing presidents and political leaders to delivering breaking news live on air, he learned quickly that clarity, trust, and authenticity matter far more than polished language or perfectly crafted talking points.

The conversation explores Rob's upcoming book Over Communicate, which focuses on a problem many organizations face today: leaders believe they are being clear, but their teams are hearing something entirely different.

They unpack why communication breakdowns happen inside organizations, how leaders can create environments where people feel heard, and why transparency and repetition are often the difference between confusion and alignment.

Rob also shares stories from his years as a news anchor, including high pressure interviews during major political moments, the discipline required to communicate clearly under pressure, and the lessons leaders can learn from broadcast journalism.

The episode also explores:

• Why leaders often believe they are communicating clearly when their teams feel the opposite • The communication habits that build trust inside organizations • What executives can learn from broadcast journalists about clarity and delivery • The realities of building a business after a career in television news • Why strong leadership communication requires repetition, transparency, and vulnerability

The conversation closes with reflections on leadership, storytelling, entrepreneurship, and the idea that communication is not about saying something once. It is about making sure it is truly understood.

Key Takeaways

✅ Why leaders consistently overestimate how clearly they communicate ✅ The habits that help executives build trust with their teams ✅ How broadcast journalism shapes confident leadership communication ✅ Why repetition is essential to strong leadership messaging ✅ The realities of entrepreneurship after a long career in media

Connect with Rob Johnson

Guest LinkedIn: https://www.linkedin.com/in/rob-johnson-communications/ Website: https://robjohnsoncommunications.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

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 Wall Street Journal, Morning Brew, and SUCCESS, and she is the author of the USA Today bestselling book Profit Generating Pipeline.

They talk about what it really takes to earn trust in 2026. The conversation covers how to run a low-urgency business without losing momentum, how to uncover real buyer urgency without manipulation, and why pricing transparency is no longer optional if you want buyers to move.

They also get into the behind-the-scenes reality of writing a book. The grind, the editing process, and what surprised Leslie most about publishing.

The episode explores:

▪️ When it is actually time to hire your first administrative assistant and how to define the role quickly ▪️ Why sellers confuse urgency with pressure and how to separate the two ▪️ A simple way to get prospects to stack-rank priorities and reveal what matters most ▪️ How Leslie builds a low-stress, low-urgency operating system using deep work and boundaries ▪️ Why putting pricing on your website reduces friction in the buyer journey ▪️ The earn the right philosophy for outreach, discovery, and follow-up ▪️ How conversation intelligence tools are changing how top sellers operate

Key Takeaways

✅ How to uncover real urgency without discounting or pressure ✅ Why low urgency can be a competitive advantage when done correctly ✅ The questions that surface true priorities and timelines quickly ✅ Why transparency builds pipeline and hiding pricing creates friction ✅ How to protect focus in a world designed to distract you ✅ What actually earns attention from modern buyers

Purchase Leslie's book: https://www.salesledgtm.com/book/

Connect with Leslie Venetz: LinkedIn: https://www.linkedin.com/in/leslievenetz TikTok: https://www.tiktok.com/@salestipstok YouTube: https://www.youtube.com/@leslievenetz Twitter/X: https://x.com/leslievenetz Instagram: https://www.instagram.com/b2bsalescoach/

Website: https://www.salesledgtm.com Leslie's Business Book Club: https://www.lesliesbookclub.com Revenue Revelry Masterclasses: https://www.revenuerevelry.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

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 telecom and technology spend.

Larry shares the philosophy behind "Do Hard Things," a principle Spyglass has operated by for more than 20 years, long before hustle culture made it trendy. The conversation dives into what it really takes to build resilient revenue teams, why rituals and standards matter in both business and family life, and how consistency compounds over time.

They unpack how Spyglass evolved from a scrappy dial-for-dollars startup into a structured, technology-enabled revenue engine. Larry breaks down how AI is impacting both go-to-market strategy and operational delivery, including the use of HubSpot, Gong, AI dialers, and automation tools to remove friction from sellers' workflows while elevating human performance instead of replacing it.

The episode also explores:

• Why sales leadership requires emotional stability through highs and lows

• How discipline and routine shape long-term performance

• The myth of work-life balance and how to manage chaos at home and work

• Why success in revenue leadership is rarely a straight line

• How to think about AI adoption without chasing every shiny object

The conversation closes with reflections on mentorship, fatherhood, resilience, and the reality that leadership is often about doing the hard things consistently when no one is watching.

Key Takeaways:

✅ Why discipline and standards create long-term revenue growth ✅ How to build resilient sales teams that survive hard cycles ✅ The real impact of AI on modern go-to-market strategy ✅ Why rituals and habits matter more than motivation ✅ How revenue leaders manage unpredictability and volatility ✅ Why doing hard things compounds over time

Connect with Larry Seiler Guest LinkedIn: https://www.linkedin.com/in/larryseiler/ Email: [email protected]

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