From Mowing Lawns to $3M Exit: The Sales Mindset That Builds Real Businesses | DJ Carroll

Why 90% of Companies Are Failing at AI (And the Reason Sales Tech Has Made Us Worse) — Jack Siney

Most of what you read about AI on LinkedIn or X is being told to you by people who are trying to sell you something. Jack Siney has lived the other side of it, talking to thousands of frontline B2B companies, and his diagnosis cuts straight through the noise. Ninety percent of companies have absolutely nothing on the business side of AI that is truly proven, scalable, and operational enough that they would risk their business on it. Jack is a 7x entrepreneur with 5 successful exits and 1 honest "learning experience." He started his career negotiating F/A-18 fighter jet contracts on behalf of the US Navy, became a Principal Consultant at PwC, then went on to co-found GovSpend (acquired by Thompson Street Capital Partners) and Advanced Public Safety (acquired by Trimble). He is now Co-Founder and Chief Revenue Officer of FrontRace, an Activity Intelligence Management platform that uses AI to reveal the invisible patterns inside how companies actually win. In this conversation Jack and Matthew get into why $650 million was spent on AI last year with 90% of it never being implemented, why forty years of sales technology has not made companies any better at hitting their forecasts, the difference between automating a real process and automating stupidness, and the simple steps every leader should take before plugging AI into their business. If you are a CEO, CRO, or founder making AI decisions right now, this episode is the reality check most of your feed is not giving you. ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 🔗 CONNECT WITH JACK SINEY LinkedIn → https://www.linkedin.com/in/jacksiney/ The Shift LinkedIn Group → https://lnkd.in/esVwNcan ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 🎙 THE CEO AND THE SALESMAN PODCAST Subscribe for more episodes → https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn → https://www.linkedin.com/in/matthewwhyatt

He Sold to a $4 Billion Competitor. Then Helped Engineer 33 More Exits. — Steven Pivnik

Most founders march toward an exit with no real plan, no clear number, and no idea how the buyer is going to value the business they spent decades building. Steven Pivnik has done the work himself, growing Binary Tree to over 200 employees across 12 countries before selling it to a $4 billion competitor, and he has since helped advise on 33 exits creating over $1.1 billion in value for the founders involved.In this conversation Steven walks through exactly how he approaches exit planning with founders, why most owners get penalised on valuation without realising it, the three drivers that move valuations the most, and the personal identity work most founders avoid until it is far too late. He also shares why his endurance sports journey, including Ironman World Championship Kona, the Seven Summits, and his 2025 Mt Everest expedition, fundamentally changed how he ran his business.If you are a founder who has built something valuable and you want to give yourself the best possible shot at converting that into the outcome you actually deserve, this conversation is essential listening.🔗 CONNECT WITH STEVEN PIVNIKPersonal site → https://stevenpivnik.com/ LinkedIn → https://www.linkedin.com/in/stevenpivnik/ Acresis Advisory → https://aipadvisory.com/ THE CEO AND THE SALESMAN PODCASTSubscribe for more episodes → https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn → https://www.linkedin.com/in/matthewwhyatt

Why Most B2B Marketing Fails (And How to Build a System That Actually Works) — Tim Fitzpatrick

Most B2B businesses think they have a lead generation problem. According to Tim Fitzpatrick, what they actually have is a marketing engine problem. He calls the place most growth-minded operators get stuck "the marketing maze," a disorienting cycle of disconnected tactics, false starts, and short-term thinking that burns money without ever building anything that compounds.Tim is the founder of Rialto Marketing and has spent over a decade as a fractional CMO and marketing advisor for B2B businesses, helping owners stop guessing and start building marketing systems that actually deliver. Before Rialto, he ran day-to-day operations at a wholesale distribution business that grew an average of 60% per year for nine years before being acquired, so he understands marketing through the lens of someone who has actually had to deliver results.If you are a growth-minded operator who knows your marketing should be working harder than it is, this conversation will give you a far clearer path forward than another tactic.CONNECT WITH TIM FITZPATRICKRialto Marketing → https://www.rialtomarketing.com/ LinkedIn → https://www.linkedin.com/in/timpfitzpatrick/ Revenue Roadblock Scorecard → http://revenueroadblockscorecard.com/THE CEO AND THE SALESMAN PODCASTSubscribe for more episodes →https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn → https://www.linkedin.com/in/matthewwhyatt

Why Most Sales Transformations Fail (And 3 Fixes That Actually Work) Matt & James, Mentor Group

Most sales organisations underperform for reasons that have very little to do with their salespeople. Matt Webb, CEO of Mentor Group, and James Barton, Chief Solutions Officer, have spent decades helping global enterprises lift the bonnet on their sales engines, and the pattern they see again and again is that the issue is almost never just one thing. It is some combination of people, process, and technology, and trying to fix one of them in isolation is like playing whack-a-mole with the warning lights on a dashboard. In this episode they break down what is actually broken inside most modern sales organisations in 2026, why pipeline coverage at 3x or 4x has become a vanity metric, the difference between content consumption and skill acquisition, why so many enablement programs fail at the embed stage, and the order in which a CRO should think about investing in leadership, technology, and AI. Matt and James have just opened their first office in North America and have recently co-authored a new book, Infinite Selling. If you lead a sales team, run enablement, or sit at the top of a revenue org wondering why the numbers are not landing the way they should, this conversation is for you. CONNECT WITH MATT WEBB LinkedIn → https://www.linkedin.com/in/matt-webb-3b34ab9/ CONNECT WITH JAMES BARTON LinkedIn → http://linkedin.com/in/jamesabarton/ MENTOR GROUP Website → https://www.mentorgroup.com/ Infinite Selling (book) → https://www.amazon.com/Infinite-Selling-Approach-Generation-Realisation/dp/B0CKV4LB79 ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 🎙 THE CEO AND THE SALESMAN PODCAST Subscribe for more episodes → https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn → https://www.linkedin.com/in/matthewwhyatt

Lessons from 30 Years Inside Big Business Transformations — Christopher Carter, CEO of Approyo

Most leaders believe their biggest threat is competition. Christopher Carter has spent decades inside some of the world's most complex scaling organisations and says the real threat is almost always internal. Complexity, dirty data, and the wrong technology in the wrong hands will slow a business down far faster than any competitor ever could.Chris is an author, keynote speaker, and one of the most experienced voices in enterprise technology and SAP implementation globally. In this conversation we get into the messy reality of what actually happens when businesses try to scale their systems without first getting the fundamentals right.WHAT WE COVER— Why complexity is the real enemy of growth and how it sneaks in through the people, not just the technology— The stair-stepping framework Chris uses when walking into organisations that have hit a wall— Why speed that makes a business successful at 10 to 50 people becomes a liability at 500 to 5,000— What actually happens when you plug AI into dirty, unstructured data— The most dangerous lie leaders tell themselves about growth— Why 97% of companies are failing to get ROI from AI and what they are doing wrong— What CEOs need to do before they even think about upgrading their ERP or adding AI toolsIf your business is growing but the cracks are starting to show, this episode is for you.Full links to Chris's books, upcoming tour dates, and speaking events are below.https://christophermcarter.com/Subscribe for more episodes: https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn: https://www.linkedin.com/in/matthewwhyattChristopher Carter: https://www.linkedin.com/in/christopher-carter-885159/