Why Founders Who Avoid Sales Always Fail with Lou Shipley

Career Resilience in the Age of AI with Ilana Golan

The career ladder is burning. And if you are still waiting for the right moment to adapt, you are already behind. In this episode, John sits down with Ilana Golan, founder of Leap Academy, to unpack what it actually takes to own your growth in a world where 92 million jobs are projected to be displaced in the next two years. From growing up a shy kid in Israel and becoming one of the first women to lead a flight instructor squad in the Israeli Air Force, to hitting rock bottom after a co-founder betrayal and building back stronger, Ilana brings a rare combination of raw honesty and practical frameworks to this conversation. They cover the 555 rule for cutting through decision paralysis, what it means to build a portfolio career, and why people will no longer pay for knowledge but will always pay for transformation. If you are ready to stop being a one-trick pony and start building something that holds up regardless of what AI throws at you, this conversation is the one to watch. Visit www.jbarrows.com [http://www.jbarrows.com] and learn how you can Make It Happen. What You’ll Learn * Why hard work still beats raw talent in any era * How to use the 555 rule to escape decision paralysis * What it looks like to lose your identity and rebuild from nothing * The case for building a portfolio career before you are forced to * Why people will not pay for knowledge but will pay for transformation Ilana Golan was an F-16 Flight instructor in the Air Force and the first female commander in her squad, a tech executive, and now the founder of Leap Academy, one of the fastest-growing companies in America. Leap Academy is disrupting professional education and is the only platform in the world today that helps individuals create portfolio careers and get ready for the future of work. Her disruption of professional education has caught the attention of leaders such as Richard Branson, Garyvee, and the Presidents of some of the biggest companies in the world. Ilana won Inc 500, Startup of the Year for 2023, CEO World Award, 40 Women to Watch, and has been on the biggest stages in the world, including Tech Crunch Disrupt, Google Startup Accelerator, Inman Connect, Executive MBA Programs, and more. Ilana was also invited to give a private talk for Richard Branson and a very selected CEOs on his private island. Connect with Llana! LinkedIn: https://www.linkedin.com/in/ilanagolan/ [https://www.linkedin.com/in/ilanagolan/] Instagram: https://www.instagram.com/ilanagolanleap [https://www.instagram.com/ilanagolanleap] Website: https://www.ilanagolan.com/ [https://www.ilanagolan.com/] Learn more about Leap Academy: https://www.leapacademy.com/ [https://www.leapacademy.com/] Join her free 3-day training: www.leapacademy.com/makeithappen [http://www.leapacademy.com/makeithappen] 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/ [https://www.linkedin.com/in/johnbarrows/] https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnBBemdVT2pBZ1dhY0szYzlzOGUzYURaekEtUXxBQ3Jtc0trNkZEWVBuS3dOOWZaZ0pZVFNrOGtNNHpuNjZWdGx0aVBhX2dNODRTdjVKVG1tS0xnRlJXWk5WOUpVdzk1YzQ1R3ZoTFhRZ3pxeFFibXU5WnFlVGJtVXl5dDUzM1JqdnkwRGRMaC05VTZ2YmNFLTFiSQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnbarrows%2F&v=bULevYtP1Ds Instagram: https://www.instagram.com/johnmbarrows/ [https://www.instagram.com/johnmbarrows/] TikTok: https://www.tiktok.com/@johnmbarrows [https://www.tiktok.com/@johnmbarrows] Check out John's Membership: https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGZxSnNVNDNhZU1zTGlfUHNWX19ZemtTLTM3QXxBQ3Jtc0tuY0sxajVtV1ZsdW5TMGtlV2tWTmNDTGVtUUZ6a1J6VmlMVi1DdU5uQ1cwRjRqdjF2ZlVqcXFveUtBWkp1WnZXSEZqQzA1TnJUclAxRVZWNm9fRjFxSlllYjdoTEd1VHFUUEFJbDdCSkR4SEU4TVgzTQ&q=https%3A%2F%2Fgo.jbarrows.com%2Fpages%2Findividual-membership%3Fref%3D3edab1&v=bULevYtP1Dshttps://go.jbarrows.com/ [https://go.jbarrows.com/] Join John's Newsletter: https://www.jbarrows.com/newsletter [https://www.jbarrows.com/newsletter]

What the Best BDR Teams Are Doing Differently Right Now with Lauren Reeves

Most BDR teams are struggling right now. Connect rates are dropping, email is getting ignored, and reps are rushing to get out of the role as fast as possible. Lauren Reeves is doing the opposite, and her team is booking more meetings every single quarter. In this episode, John sits down with Lauren Reeves, BDR manager at Swap Commerce and one of the most vocal advocates for the SDR and BDR profession in Europe. Lauren built her team from 6 to 40, incentivized her reps to build real personal brands on LinkedIn, and created a culture where people actually want to stay in the seat long enough to get good at it. She shares exactly what is working right now on email, on the phone, and on social, and what is quietly killing results for most teams that are copying the playbook from five years ago. If you lead a BDR or SDR team, or you are in the role of trying to figure out how to stand out and build a career in sales, this conversation will give you the most practical and honest take on what it actually takes to win right now. Visit www.jbarrows.com and learn how you can Make It Happen. What You’ll Learn * The hiring question Lauren asks in every interview * Why Lauren tells every candidate upfront: I do not work with dicks * Why good BDRs should stay in the seat for at least 18 months * Why the no promotion before a year policy creates better salespeople * What is actually working right now in email * Why the phone still converts * How Lauren pays her reps to post on LinkedIn * What BDRs should post on LinkedIn * Why costly quarterly targets work better than monthly pressure * How to spot it in an interview and how to coach it on the floor Lauren Reeves is a sales leader and outbound specialist with 7 years of experience in the BDR/SDR space, known for developing high-performing business development teams. She began her career as a BDR before moving into management, where she focuses on building ambitious, growth-driven sales professionals and creating environments centered on learning, collaboration, and success. Lauren has driven significant outbound revenue growth, scaled teams across regions, and earned recognition as a top sales manager and leader in the industry. LinkedIn: https://www.linkedin.com/in/thelaurenreeves/ [https://www.linkedin.com/in/thelaurenreeves/] 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/ [https://www.linkedin.com/in/johnbarrows/] https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnBBemdVT2pBZ1dhY0szYzlzOGUzYURaekEtUXxBQ3Jtc0trNkZEWVBuS3dOOWZaZ0pZVFNrOGtNNHpuNjZWdGx0aVBhX2dNODRTdjVKVG1tS0xnRlJXWk5WOUpVdzk1YzQ1R3ZoTFhRZ3pxeFFibXU5WnFlVGJtVXl5dDUzM1JqdnkwRGRMaC05VTZ2YmNFLTFiSQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnbarrows%2F&v=bULevYtP1Ds Instagram: https://www.instagram.com/johnmbarrows/ [https://www.instagram.com/johnmbarrows/] TikTok: https://www.tiktok.com/@johnmbarrows [https://www.tiktok.com/@johnmbarrows] Check out John's Membership: https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGZxSnNVNDNhZU1zTGlfUHNWX19ZemtTLTM3QXxBQ3Jtc0tuY0sxajVtV1ZsdW5TMGtlV2tWTmNDTGVtUUZ6a1J6VmlMVi1DdU5uQ1cwRjRqdjF2ZlVqcXFveUtBWkp1WnZXSEZqQzA1TnJUclAxRVZWNm9fRjFxSlllYjdoTEd1VHFUUEFJbDdCSkR4SEU4TVgzTQ&q=https%3A%2F%2Fgo.jbarrows.com%2Fpages%2Findividual-membership%3Fref%3D3edab1&v=bULevYtP1Dshttps://go.jbarrows.com/ [https://go.jbarrows.com/] Join John's Newsletter: https://www.jbarrows.com/newsletter [https://www.jbarrows.com/newsletter]

The First Guy to Lose to Salesforce (And What He Did Next) with Kris Lawson

Before your buyer takes your call, their AI has already researched you, evaluated your solution, and started forming an opinion. The question isn't whether AI is changing sales. It's whether you're going to catch up to what's already happening on the other side of the table. In this episode, John sits down with Kris Lawson, the sales leader, founder of Ruby, and Snowflake alumnus, to unpack the most important shift in B2B sales that most people are completely ignoring. Kris was the first Oracle rep ever to lose a deal to Salesforce, went on to build and scale sales teams across some of the most iconic tech companies of the last 25 years, and is now building the AI-powered sales assistant he always wished he had. From how buyers are already using AI to screen vendors, to why generic AI tools will never replace purpose-built sales intelligence, to how to pick a rocket ship company before anyone else knows it's one, this conversation covers the ground that matters most right now. If you're in sales, leading a sales team, or building a company and trying to figure out how to win in an AI-saturated market, this episode will change how you think about what's coming. Visit www.jbarrows.com [http://www.jbarrows.com] and learn how you can Make It Happen. What You’ll Learn * Why your buyer's AI is already evaluating you * How OpenAI and Anthropic told one company to "just send the documentation" and let their LLMs decide * The framework Kris uses to evaluate whether a company is worth joining * Why the first Oracle rep to lose a deal to Salesforce ended up joining Salesforce * Why the chat interface will never work for the average sales rep * The build-vs-buy fallacy in the AI era and the real risks nobody is talking about * How AI will reshape sales methodologies * The rubber duck exercise and how to use AI to learn, not just execute * Why choosing the right life partner is the most important career decision a salesperson will ever make Kris Lawson is a sales leader, entrepreneur, and co-founder of Ruby (heyruby.ai) — an AI-powered sales assistant purpose-built to help sales reps be excellent in every customer interaction. Kris has spent 25 years scaling go-to-market organizations at Oracle, Salesforce, Microsoft, and Snowflake. He was the first Oracle rep ever to lose a deal to Salesforce, went on to become a key early sales leader in Canada for Salesforce, and has since built and exited multiple sales organizations in the tech sector. He is also co-founder of Snow Angels, a Snowflake alumni investor syndicate focused on data and AI startups. Connect with Kris Lawson: Website: https://www.heyruby.ai/ [https://www.heyruby.ai/] LinkedIn: https://www.linkedin.com/in/krislawsonland/ [https://www.linkedin.com/in/krislawsonland/] 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/ [https://www.linkedin.com/in/johnbarrows/] https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnBBemdVT2pBZ1dhY0szYzlzOGUzYURaekEtUXxBQ3Jtc0trNkZEWVBuS3dOOWZaZ0pZVFNrOGtNNHpuNjZWdGx0aVBhX2dNODRTdjVKVG1tS0xnRlJXWk5WOUpVdzk1YzQ1R3ZoTFhRZ3pxeFFibXU5WnFlVGJtVXl5dDUzM1JqdnkwRGRMaC05VTZ2YmNFLTFiSQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnbarrows%2F&v=bULevYtP1Ds Instagram: https://www.instagram.com/johnmbarrows/ [https://www.instagram.com/johnmbarrows/] TikTok: https://www.tiktok.com/@johnmbarrows [https://www.tiktok.com/@johnmbarrows] Check out John's Membership: https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGZxSnNVNDNhZU1zTGlfUHNWX19ZemtTLTM3QXxBQ3Jtc0tuY0sxajVtV1ZsdW5TMGtlV2tWTmNDTGVtUUZ6a1J6VmlMVi1DdU5uQ1cwRjRqdjF2ZlVqcXFveUtBWkp1WnZXSEZqQzA1TnJUclAxRVZWNm9fRjFxSlllYjdoTEd1VHFUUEFJbDdCSkR4SEU4TVgzTQ&q=https%3A%2F%2Fgo.jbarrows.com%2Fpages%2Findividual-membership%3Fref%3D3edab1&v=bULevYtP1Dshttps://go.jbarrows.com/ [https://go.jbarrows.com/] Join John's Newsletter: https://www.jbarrows.com/newsletter [https://www.jbarrows.com/newsletter]

Why Founders Who Avoid Sales Always Fail with Lou Shipley

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 [http://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/ [https://www.loushipley.com/] LinkedIn: https://www.linkedin.com/in/loushipley/ [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/ [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/ [https://www.linkedin.com/in/johnbarrows/] https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnBBemdVT2pBZ1dhY0szYzlzOGUzYURaekEtUXxBQ3Jtc0trNkZEWVBuS3dOOWZaZ0pZVFNrOGtNNHpuNjZWdGx0aVBhX2dNODRTdjVKVG1tS0xnRlJXWk5WOUpVdzk1YzQ1R3ZoTFhRZ3pxeFFibXU5WnFlVGJtVXl5dDUzM1JqdnkwRGRMaC05VTZ2YmNFLTFiSQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnbarrows%2F&v=bULevYtP1Ds Instagram: https://www.instagram.com/johnmbarrows/ [https://www.instagram.com/johnmbarrows/] TikTok: https://www.tiktok.com/@johnmbarrows [https://www.tiktok.com/@johnmbarrows] Check out John's Membership: https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGZxSnNVNDNhZU1zTGlfUHNWX19ZemtTLTM3QXxBQ3Jtc0tuY0sxajVtV1ZsdW5TMGtlV2tWTmNDTGVtUUZ6a1J6VmlMVi1DdU5uQ1cwRjRqdjF2ZlVqcXFveUtBWkp1WnZXSEZqQzA1TnJUclAxRVZWNm9fRjFxSlllYjdoTEd1VHFUUEFJbDdCSkR4SEU4TVgzTQ&q=https%3A%2F%2Fgo.jbarrows.com%2Fpages%2Findividual-membership%3Fref%3D3edab1&v=bULevYtP1Dshttps://go.jbarrows.com/ [https://go.jbarrows.com/] Join John's Newsletter: https://www.jbarrows.com/newsletter [https://www.jbarrows.com/newsletter]

Selling What They Think Is Free with Eric Appel

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 [https://island.io] LinkedIn: https://www.linkedin.com/in/eric-appel-605310/ [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/ [https://www.linkedin.com/in/johnbarrows/] https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbnBBemdVT2pBZ1dhY0szYzlzOGUzYURaekEtUXxBQ3Jtc0trNkZEWVBuS3dOOWZaZ0pZVFNrOGtNNHpuNjZWdGx0aVBhX2dNODRTdjVKVG1tS0xnRlJXWk5WOUpVdzk1YzQ1R3ZoTFhRZ3pxeFFibXU5WnFlVGJtVXl5dDUzM1JqdnkwRGRMaC05VTZ2YmNFLTFiSQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fjohnbarrows%2F&v=bULevYtP1Ds Instagram: https://www.instagram.com/johnmbarrows/ [https://www.instagram.com/johnmbarrows/] TikTok: https://www.tiktok.com/@johnmbarrows [https://www.tiktok.com/@johnmbarrows] Check out John's Membership: https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGZxSnNVNDNhZU1zTGlfUHNWX19ZemtTLTM3QXxBQ3Jtc0tuY0sxajVtV1ZsdW5TMGtlV2tWTmNDTGVtUUZ6a1J6VmlMVi1DdU5uQ1cwRjRqdjF2ZlVqcXFveUtBWkp1WnZXSEZqQzA1TnJUclAxRVZWNm9fRjFxSlllYjdoTEd1VHFUUEFJbDdCSkR4SEU4TVgzTQ&q=https%3A%2F%2Fgo.jbarrows.com%2Fpages%2Findividual-membership%3Fref%3D3edab1&v=bULevYtP1Dshttps://go.jbarrows.com/ [https://go.jbarrows.com/] Join John's Newsletter: https://www.jbarrows.com/newsletter [https://www.jbarrows.com/newsletter]