Every founder who has ever handed sales off too early has paid for it. Every single one.

In this episode, John sits down with Lou Shipley, a Harvard Business School lecturer, board member, investor, and author of Unlikely Entrepreneurs, to dig into why sales is still the most misunderstood function in business, and why founders who treat it as a second-class citizen almost always fail. Lou draws from decades of experience running companies, building sales cultures from scratch, and teaching MBAs how to sell before they ever launch a product.

From cold-calling encyclopedia buyers to opening Asia for Avid Technology to building the sales curriculum at HBS, Lou has lived every stage of the sales journey, and he's done it at the highest level.

If you're a founder, a sales professional, or anyone trying to understand what it actually takes to build a company in the age of AI, this conversation will challenge everything you think you know about selling. Visit www.jbarrows.com and learn how you can Make It Happen.

What You’ll Learn

• Why founders who delegate sales too early almost always fail
• How Lou built one of Harvard's most in-demand courses
• The cultural disdain of sales
• Why sales is not about convincing anyone of anything
• How to use AI as a learning tool instead of an answer machine
• What the Guy Kawasaki GPT experiment revealed
• Why curiosity is the most important professional skill in the AI era
• What SaaS companies should be doing right now
• How to build a farm system for sales talent
• 17 stories that prove anyone can build something worth buying

Lou Shipley is a multi-time tech CEO, entrepreneur, and enterprise software leader with over 25 years of experience driving growth and innovation. He has led several successful startups through rapid expansion and acquisition, including Black Duck, WebLine (acquired by Cisco), Reflectent (acquired by Citrix), and VMTurbo. In addition to his executive leadership, Lou serves on multiple boards, teaches technology sales at Harvard Business School, and is a respected mentor, speaker, and commentator in the tech industry.

Connect with Lou Shipley:

Website: https://www.loushipley.com/

LinkedIn: https://www.linkedin.com/in/loushipley/

Grab a copy of Lou Shipley’s book, “Unlikely Entrepreneurs: Wins, Losses, and Crucial Lessons on Building Great Companies,“ on Amazon: https://www.amazon.com/Unlikely-Entrepreneurs-Lou-Shipley/dp/1394345895/

John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment.

Connect with John Barrows:

LinkedIn: https://www.linkedin.com/in/johnbarrows/

Instagram: https://www.instagram.com/johnmbarrows/

TikTok: https://www.tiktok.com/@johnmbarrows

Check out John's Membership: https://go.jbarrows.com/

Join John's Newsletter: https://www.jbarrows.com/newsletter

If your prospect thinks they can already get what you're selling for free, you don't have a product problem — you have a positioning problem.

In this episode, John sits down with Eric Appel, CRO of Island, the company that turned a free commodity — the browser — into one of the fastest-growing enterprise security platforms in the world. Eric pulls back the curtain on how Island landed eight of the top ten US financial institutions as early customers, why the advisor network beats outbound at scale, and what today's sales reps are getting catastrophically wrong before they even open their mouths.

If you're navigating a market where AI is commoditizing everything around you and buyers think they don't need what you're selling, this conversation will change how you think about value, positioning, and the future of selling. Visit www.jbarrows.com and learn how you can Make It Happen.

What You’ll Learn

• How Island sold a "free" product to the world's biggest enterprises — and won
• The advisor network strategy that replaced traditional outbound prospecting
• Why the first 15 sales hires at Island were all known killers — and why that matters
• How to build a real feedback loop between sales and engineering
• The three questions you should never ask a prospect (and what to do instead)
• Why hypothesis selling is replacing discovery in today's AI-driven sales environment
• What separates leaders from followers in the AI era — and why followers will get left behind

Eric Appel is the Chief Revenue Officer at Island, the enterprise browser company redefining how organizations think about security, productivity, and AI enablement. With a career that spans Arthur Anderson, Yahoo, McAfee, and some of the most pivotal chapters in information security, Eric has spent over two decades building go-to-market engines for category-defining companies. At Island, he helped architect the sales strategy that brought the world's largest financial institutions, pharma companies, and global enterprises onto the platform — proving that even a "free" product can command a premium price when the value proposition is airtight.

Connect with Eric Appel:

Website: https://island.io

LinkedIn: https://www.linkedin.com/in/eric-appel-605310/

John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment.

Connect with John Barrows:

LinkedIn: https://www.linkedin.com/in/johnbarrows/

Instagram: https://www.instagram.com/johnmbarrows/

TikTok: https://www.tiktok.com/@johnmbarrows

Check out John's Membership: https://go.jbarrows.com/

Join John's Newsletter: https://www.jbarrows.com/newsletter

Sales is about solving problems. It’s about helping people achieve their goals—and that’s exactly what innovation is at its core.

In this episode, John sits down with Jason Wild, author of Genius at Scale: How Great Leaders Drive Innovation, to talk about his journey from Chicago to becoming a high-level entrepreneur. Drawing from his experience working with companies like IBM and Salesforce, he breaks down the ABC structure that helps business owners think differently and drive meaningful innovation.

If you’re ready to elevate how you approach growth, this conversation will challenge your perspective on leadership, strategy, and the results you’re capable of creating. Visit www.jbarrows.com and learn how you can Make It Happen.

What You’ll Learn

• What it’s like to work with IBM and Salesforce
• The ABC structure for innovation
• Laying out the framework for innovation
• Aligning People In One Vision
• Approaching innovation in the era of AI

From a child actor in Hollywood to tech executive in Silicon Valley, Jason Wild has collaborated with some of the most talented and creative people in the world. He is an adviser and author on growth, innovation, strategy, and leadership, having led projects in 40 countries from Disney and AT&T to NATO and the City of Paris. He is the co-founder of Wild Innovation Consulting and helps leaders and organizations unlock their genius at scale, with significant experience in AI, business, and operating models, and digital transformation. He worked for over 20 years in executive roles at Microsoft, IBM, and Salesforce. He is dedicated to ensuring that AI and emerging tech benefit all of humanity.

Connect with Jason Wild:

Website: https://geniusatscale.com/

LinkedIn: https://www.linkedin.com/in/jasonwild/

Get a copy of “Genius at Scale: How Great Leaders Drive Innovation” on Amazon: https://www.amazon.com/Genius-Scale-Great-Leaders-Innovation/dp/1647827507

John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment.

Connect with John Barrows:

LinkedIn: https://www.linkedin.com/in/johnbarrows/

Instagram: https://www.instagram.com/johnmbarrows/

TikTok: https://www.tiktok.com/@johnmbarrows

Check out John's Membership: https://go.jbarrows.com/

Join John's Newsletter: https://www.jbarrows.com/newsletter

Start by asking yourself: What am I good at? What do I love doing? And ultimately, what will I get paid for?

In this episode, John is joined by Roderick Jefferson to have a real conversation about ambition, ego, and the true cost of success across our lives, relationships, and leadership. Together, they unpack the importance of slowing down, why constant hustle can come at a price, and the powerful lessons Roderick learned after experiencing a stroke.

If you’re at the stage where you’re focused on building a legacy and discovering your deeper “why,” this episode will challenge and expand your perspective on what it really means to be successful.

Want to equip yourself for success before it’s too late? Visit www.jbarrows.com and learn how you can Make It Happen.

What You’ll Learn

• Why work-life balance is a lie
• The impact of taking a break
• How to use AI to your advantage
• Understanding ambition vs ego
• Building your own legacy

Roderick Jefferson is an internationally recognized speaker, author, and thought leader who lives and breathes enablement. With more than 25 years of experience, he has held senior executive positions at companies such as Siebel, NetApp, Salesforce, Oracle, and others. He had delivered keynotes, guest lectures, webinars, and podcasts in fourteen countries at prominent events and conferences, sharing his vibrant and engaging insights with a worldwide audience. Roderick is an acknowledged thought leader in the enablement space and the author of Sales Enablement 3.0: The Blueprint to Sales Enablement Excellence™, an Amazon #1 New Release and best-selling book, and the Sales Enablement 3.0 Companion Workbook™, which guides organizations aiming to enhance their sales strategies through effective enablement practices.

Connect with Roderick Jefferson:

Website: https://www.roderickjefferson.com/

LinkedIn: https://www.linkedin.com/in/roderickjefferson/

Facebook: https://www.facebook.com/ThevoiceofRod/

Instagram: https://www.instagram.com/roderick_j_associates/?hl=en

YouTube: https://www.youtube.com/channel/UCShK1i36e1AY1yVHHPh93wQ

X: https://x.com/thevoiceofrod?lang=en

Grab a copy of “Sales Enablement 3.0: The Blueprint to Sales Enablement Excellence” on Amazon: https://www.amazon.com/Sales-Enablement-3-0-Blueprint-Excellence/dp/1736190903

John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment.

Connect with John Barrows:

LinkedIn: https://www.linkedin.com/in/johnbarrows/

Instagram: https://www.instagram.com/johnmbarrows/

TikTok: https://www.tiktok.com/@johnmbarrows

Check out John's Membership: https://go.jbarrows.com/

Join John's Newsletter: https://www.jbarrows.com/newsletter

Most startups obsess over growth. Very few actually understand when scaling makes sense—and when it doesn’t.

In this episode, John talks with Mark Roberge about the real science behind building and scaling a company. They unpack the myths around product-market fit, the ethical decision point every salesperson faces, and why revenue alone can be a dangerously misleading signal for founders.

If you're building, selling, or leading a team, this conversation will challenge how you think about growth, customer value, and the future of sales in an AI-driven world.

Ready to sharpen your sales skills and stay relevant in a rapidly changing market? Head over to www.jbarrows.com and keep learning how to Make It Happen.

What You’ll Learn

1. Why revenue isn’t product-market fit
2. The ethical decision point in sales
3. Why retention beats new revenue
4. The role of a customer success matrix
5. How AI may reshape sales careers

Mark Roberge is the founding CRO of HubSpot, where he scaled revenue from zero to over $100M and helped take the company public. After leaving HubSpot, he joined the faculty at Harvard Business School and co-founded Stage 2 Capital, the first VC firm run and backed by go-to-market leaders. He’s also the author of The Science of Scaling, which introduces a data-driven framework to help founders decide when to scale, how fast to grow, and whether scaling makes sense at all.

Connect with Mark Roberge:

LinkedIn: https://www.linkedin.com/in/markroberge

Instagram: https://www.instagram.com/roberge_mark

X: https://x.com/markroberge

Mark's Bestselling Books Amazon: https://www.amazon.com/stores/author/B00NSKE4WY

John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment.

Connect with John Barrows:

LinkedIn: https://www.linkedin.com/in/johnbarrows/

Instagram: https://www.instagram.com/johnmbarrows/

TikTok: https://www.tiktok.com/@johnmbarrows

Check out John's Membership: https://go.jbarrows.com/

Join John's Newsletter: https://www.jbarrows.com/newsletter

AI is changing sales. But trust still wins deals.

In this episode of Make It Happen Mondays, John Barrows sits down with negotiation expert Tim Castle to break down what it actually takes to negotiate and close deals in today’s AI-driven sales environment.

They dive into the real difference between influence and manipulation, why belief in what you sell matters more than ever, and how preparation, emotional awareness, and cultural nuance shape successful negotiations. Tim also explains how AI can help sales professionals prepare faster while reminding us that human connection and trust are still the ultimate advantage.

If you're serious about improving how you sell, negotiate, and build trust with buyers in the AI era, this episode delivers practical insights you can apply right away.

Want to sharpen your sales skills and stay ahead of the curve? Head over to www.jbarrows.com and start building the systems that help you close more deals.

What You’ll Learn

1. Why belief in your product matters
2. Influence vs manipulation in negotiations
3. How top negotiators prepare
4. Using AI for better sales prep
5. Why trust still wins in sales

Tim Castle is a globally recognized negotiation expert ranked among the Top 30 Negotiation Professionals in the World (2025) by Global Gurus. He is an award-winning author of multiple bestsellers, including The Art of Negotiation and The Momentum Sales Model, and the founder of the Negotiation Edge Training Academy. Tim works with ambitious organizations that want to win negotiations with integrity, build influence, and create stronger buyer relationships in an increasingly AI-driven world.

Connect with Tim Castle:

Website: https://www.timjscastle.com/

Facebook: https://www.facebook.com/TimJSCastle

LinkedIn: https://www.linkedin.com/in/timcastle3/

Instagram: https://www.instagram.com/timjscastle/

X: https://x.com/TimJSCastle

TikTok: tiktok.com/@timjscastle

Tim's Bestselling Books Amazon: https://www.amazon.com/stores/Tim-Castle/author/B07G6LF77C?

John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment.

Connect with John Barrows:

LinkedIn: https://www.linkedin.com/in/johnbarrows/

Instagram: https://www.instagram.com/johnmbarrows/

TikTok: https://www.tiktok.com/@johnmbarrows

Check out John's Membership: https://go.jbarrows.com/

Join John's Newsletter: https://www.jbarrows.com/newsletter

Artificial Intelligence is transforming sales faster than any technology shift we’ve seen before. In this episode of Make It Happen Mondays, John Barrows sits down with Peter Grant, CRO of You.com and a four-time unicorn operator who helped scale companies like Salesforce and Siebel.

Peter shares his journey from the British military to enterprise software leadership, and how that experience shaped his approach to leadership, hiring, and sales discipline. The conversation dives deep into how AI is changing enterprise sales, go-to-market strategies, and the future of work.

They explore why AI literacy is becoming a mandatory skill, how sales organizations are evolving, and why the gap between top performers and average sellers is about to grow dramatically.

If you work in sales, leadership, or technology, this episode will challenge the way you think about productivity, hiring, and the role of AI in modern business.

What You’ll Learn in This Episode

• How Peter Grant went from the military to leading revenue at multiple unicorn companies

• Why AI is the biggest disruption to sales since the internet

• The evolving role of sales professionals in an AI-driven world

• Why top performers are becoming even more effective with AI tools

• The risks of relying too heavily on AI without critical thinking

• How enterprise companies are adopting AI and measuring ROI

• The importance of AI literacy for professionals in every industry

• Why the future of work will reward curiosity, adaptability, and continuous learning

About the Guest

Peter Grant is the Chief Revenue Officer at You.com, an AI platform helping enterprises deploy generative AI solutions with measurable ROI. He has helped scale several high growth technology companies, including Salesforce and Siebel, and is known for building high-performing revenue teams in emerging technology markets. MIHM Peter Grant

Key Takeaways

AI is accelerating the performance gap.

Top performers who embrace AI will become dramatically more productive, while those who rely on outdated processes risk falling behind.

AI literacy is becoming essential.

Understanding how to effectively use AI tools will soon be a core skill across nearly every profession.

Sales roles are evolving.

The traditional sales process is changing as buyers gain access to more information and automation tools.

Curiosity and adaptability matter more than ever.

Professionals who continuously learn and experiment with AI will have a significant advantage.

Resources Mentioned

You.com – https://you.com/business

John Barrows Training – https://jbarrows.com

Stefan Feuerstein isn’t just an expert in delegation—he’s a humanitarian leader with a track record of real-world impact. In this powerful episode, Stefan joins John to unpack the simple but transformational delegation model from his book ABC Delegation.

But this conversation goes far deeper than business. Stefan’s approach—Autonomy, Briefing, and Consent—was born not in a boardroom, but in the field. From leading 250 people in Honduras (the murder capital of the world) to supporting migrant children at the U.S. border, Stefan’s leadership method was forged under pressure in some of the world’s most difficult environments.

Together, they break down the mindset shift needed to delegate effectively (especially for control-prone entrepreneurs), the practical framework for implementing ABC, and real examples of how it’s driving results for teams worldwide—from humanitarian missions to Fortune 500 companies.

If you’ve ever said “I’ll just do it myself,” this episode will challenge you—and give you the tools to lead and let go.

Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together!

Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/

Connect with John on IG: https://www.instagram.com/johnmbarrows/

Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1

Join John's Newsletter: https://www.jbarrows.com/newsletter

Connect with Stefan on LinkedIn: https://www.linkedin.com/in/stefan-feuerstein-0b35a7117/

Check out Stefan's Website: https://abcdelegation.com/

This episode is different.

Devin Reed returns to the podcast—but this time, it’s not about content strategy, marketing tactics, or growth frameworks. It’s about something far more personal and far more relevant.

After posting a powerful message about how “business as usual” feels disconnected from reality right now, Devin made a conscious decision to stop staying quiet. That post sparked this conversation.

Together, John and Devin unpack what it means to:

1. Speak up without becoming divisive
2. Use your platform responsibly
3. Navigate uncertainty without pretending everything is fine
4. Find your voice when you’re not sure what to say
5. Lead with integrity in emotionally charged times

This is a raw, thoughtful discussion about privilege, responsibility, fear of backlash, and the tension between staying silent and standing for something. It’s not about politics. It’s about humanity. It’s about leadership.

If you’ve been feeling the disconnect…

If you’ve been unsure how to show up…

If you’ve been wrestling with whether to speak or stay quiet…

This conversation might help you find clarity—and maybe even a little courage.

Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together!

Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/

Connect with John on IG: https://www.instagram.com/johnmbarrows/

Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1

Join John's Newsletter: https://www.jbarrows.com/newsletter

Connect with Devin on LinkedIn: https://www.linkedin.com/in/devinreed/

Check out Devin's Website: https://www.thereeder.co/

In this episode of Make It Happen Mondays, John sits down with Saif Khan, Regional VP of EMEA and APAC at Semrush, one of the top SaaS platforms helping digital marketers drive visibility, traffic, and growth. But this episode isn’t just about tools or tactics—it’s about the real human side of sales leadership.

From growing up in a council estate in West London to building elite sales teams across two continents, Saif shares how a single ride-along with his uncle sparked his lifelong passion for sales. He breaks down how five years in retail taught him more about buyer psychology than any formal sales training ever could—and why emotional intelligence, not just methodology, is the real differentiator in today’s market.

The conversation dives into:

• How burnout creeps in even during “success”

• Why Saif hit pause on his career for a solo journey through Southeast Asia

• The coaching crisis in frontline management

• The line between AI augmentation and AI dependency—and what it means for the future of leadership.

Whether you’re an SDR, a VP, or somewhere in between, this episode is packed with real stories, fresh takes, and valuable lessons for anyone navigating the evolving world of modern sales.

Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together!

Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/

Connect with John on IG: https://www.instagram.com/johnmbarrows/

Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1

Join John's Newsletter: https://www.jbarrows.com/newsletter

Connect with Saif on LinkedIn: https://www.linkedin.com/in/saif-khan-cism/

Check out Saif's Website Semrush: https://www.semrush.com/

Check out these additional links for Semrush

Employment Opportunities: https://careers.semrush.com/jobs/

Apple Podcast: https://podcasts.apple.com/es/podcast/technically-her/id1871241654?l=en-GB

Spotify: https://open.spotify.com/show/7nBfeFVia9d7ClK7CVOBcV?si=9ef5467e40644435

Instagram: https://www.instagram.com/semrush_life/#

Youtube: https://www.youtube.com/@SemrushLife

LinkedIn: https://www.linkedin.com/company/semrush/posts/?feedView=all

TikTok: http://tiktok.com/@semrushlife

In this episode, John sits down with Ashley Herd, a former General Counsel and HR executive turned founder of Manager Method — a movement and book that gives managers the real-world tools no one else teaches. She’s also a LinkedIn Learning instructor, podcast host, and a powerful advocate for human-first leadership.

Ashley brings a sharp legal and HR background from brands like KFC and McKinsey, and shares how those experiences opened her eyes to a problem most companies ignore: we don’t train our managers.

This conversation dives into:

1. Why most managers are set up to fail
2. Her signature framework: Pause. Consider. Act.
3. How to shift from micromanagement to trust
4. The three leadership styles: Tight Jeans, Sweatpants, and Cozy Joggers
5. What KFC taught her about recognition and culture
6. How to support employees during grief, loss, and hard times

If you’re a frontline manager, a senior leader, or someone trying to improve your org’s leadership culture, this episode is packed with honest insight, practical frameworks, and real empathy for the people doing the hardest job in business: managing other people.

Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together!

Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/

Connect with John on IG: https://www.instagram.com/johnmbarrows/

Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1

Join John's Newsletter: https://www.jbarrows.com/newsletter

Connect with Ashley on LinkedIn: https://www.linkedin.com/in/ashleyherd/

Check out Ashley's Website: https://www.managermethod.com/

Get Ashley's Book "The Manager Method" Here: https://www.amazon.com/Manager-Method-Practical-Framework-Support/dp/B0F88XQ919/ref=sr_1_1?crid=3OXJB8FFOLV4P&dib=eyJ2IjoiMSJ9.gCPkw0XjqseVzVOGs73g3eB07oBsCIPccO7Bg_F6_pJUk_7hYRf_o4C7UEKTRNAKfZZubHS4muiYeQwrCl2bTruXHFHdVzSIcOgY2Ro0vyR55Lg6emhKDYAInm1NlGQq4aRtfUIBaphOf1El-r00xw.zVw99DEqK3s5Fks8X-BIFrh6_YByNw6CA-exZYjmUhw&dib_tag=se&keywords=ashley+herd&qid=1770643943&sprefix=Ashley+Herd%2Caps%2C142&sr=8-1