The Streetwise Founders' Thoughts.

Just upgraded to the Apple iPhone 17 and somehow my favourite "feature" survived the migration: the Apple Pay double click side button that works perfectly… about 60% of the time. You know the drill: Line behind you, terminal ready, you double click the side button to confirm and: iPhone: "Never heard of it." Cancel. Back out. Start again. Suddenly it works, like nothing ever happened. For a company that can put a desktop class chip in a phone, it blows my mind that these tiny, very repeatable UX glitches can live on for multiple generations. It really makes you wonder: Is software getting so complex and teams so overloaded that obviously fixable "papercut" bugs just never make it to the top of the backlog? Do you think we've normalised a level of friction that would have been unacceptable 10 years ago? In the meantime, if you see someone at the checkout rage tapping their side button, please be kind. They're not failing the tech. The tech is failing them.

The public clash between these two is a nice break from the madness we are seeing in the media these days. Ego meets economics! While both are undeniably ego driven visionaries, only one of them actually runs a profitable business. O'Leary refused to install Starlink wifi on Ryanair flights (would cost €200-250M annually). Musk called him an "idiot." O'Leary called Musk back "an idiot", Then Musk jokingly threatened to buy Ryanair. And O'Leary's response? Absolutely brutal. He literally capitalized on the feud with a "Big Idiot Seat Sale" that boosted bookings. (Never miss a marketing opportunity.) Musk's Playbook: The Investment & Debt Model SpaceX: Started with $100M personal wealth, then relied on $38B+ in government contracts and subsidies Tesla: Survived early on thanks to a critical $465M DOE loan (2010) X (Twitter): Bought for $44B in 2022 with $12.5B in bank debt financing Strategy: Get others to fund it, iterate, hope for exponential returns O'Leary's Playbook: The Revenue & Efficiency Model Built Ryanair on operational ruthlessness: single aircraft type, secondary airports, ancillary revenue (baggage, seats, snacks) H1 2025 Revenue: €9.82bn (up 13%) Self funds growth from profits Strategy: Cut costs, maximize revenue per passenger, repeat The Ego vs. Economics Reality: Both men have massive egos. Both disrupt their industries. Only one built a business model that actually makes money without constantly needing external capital injections. O'Leary figured out the hard way that profitability beats valuation hype every single time. Meanwhile, Musk's still discovering that owning a social media platform is harder than landing rockets. And O'Leary's leveraging the entire feud into free marketing.

What happened to all the Agentic AI sales tools? No automated LinkedIn messages, no automated emails, no strange looking AI bots commenting on posts anymore. I thought these tools were going to replace Sales People and increase everyone's sales by X million %? Has everyone just moved on to the next trendy tools or am I missing something? The truth is messier than trend fatigue. The automated outreach tools of before worked because they exploited a gap: LinkedIn and email providers weren't equipped to detect bot behaviour at scale. Volume was the strategy. You'd fire off 500 messages from a template, accept a 5% response rate, and call it a win. Then the detection systems got smarter. LinkedIn banned thousands of accounts in 2024 without appeal. They implemented behavioural biometrics that catch repetitive patterns instantly. Email providers started flagging AI generated content with accuracy. The entire spray and pray playbook became a liability instead of an asset. Here's the interesting part: Agentic AI in sales isn't dead. It's evolved. The new breed of AI tools don't pretend to be human anymore. They don't send messages on your behalf. Instead, they're living inside your existing workflows like true agents: analysing buyer behaviour, qualifying leads in real time, personalising at scale through context not templates, and surfacing decisions for humans to act on. The tools that looked cool didn't actually work for long. The tools that look boring in the background are the ones winning right now. Human judgment plus AI research still beats pure automation. That hasn't changed.

Events aren't what they used to be. As both an attendee and an organiser, I've had a front row seat to the way events have transformed over the past couple of years. Some organisers adapted fast. They made space for genuine interaction, broke up long sessions with networking or Q&A, and didn't just rely on old formats. Others tried to force traditional approaches into a digital world. Endless slides, no personal touch, little room for connection. It showed. What works now? Thoughtful design. Putting the attendee first, every time. Mixing live interaction with on demand content. Creating opportunities for real conversations, not just presentations. The events that succeed are run by teams who listen, experiment, and aren't afraid to change what isn't working. Those that don't evolve, lose their audience. Simple as that.

Most people are struggling with lead generation. The market is changing quickly and strategies that worked before are not working now. For example, if more content, more platforms, and more followers actually worked, wouldn't we all be booked out by now? Here's the uncomfortable truth: High-ticket leads don't come from shouting louder. They come from structure. Step 1: Nail your offer If your audience can't instantly tell who it's for, what problem you solve, and why you're different, you'll get likes, not leads. Clarity isn't optional. It's the entire game. Step 2: Repetition crushes novelty Stop trying to teach everything you know in every post. Hammer your core message from every angle. Clients buy what they recognise. If your message changes every week, don't be surprised when your pipeline dries up. Step 3: Stop hiding your entry point Most CTAs sound generic and high-commitment. Nobody wants to "jump on a call" with a stranger about an undefined offer. Instead, offer a small, clear, low-pressure step — a focused 1:1 session, a short workshop, or a mini-mastermind. Step 4: Guide them with confidence Have a sales system that moves the right people to your offer, naturally. No pressure. No awkwardness. Just clarity about next steps, and the confidence to invite. Here's the twist: You don't need a bigger audience. You don't need a brand new business idea. You need to tighten your structure and stick with it.

Sales reps waste 65% of their time on non-selling activities. One good thing that AI is currently changing is reducing this %. I have spent the past few months using Sybill to take notes during sales calls and it has drastically increased my productivity. Sybill not only takes notes, it compiles them into actions and recommended next steps, shows buyer intent and provides easy to read summaries. Definitely worth adopting these AI note takers into your tech stack!

The full list of companies and services that were affected by the outage yesterday: Social Media & Messaging: Snapchat, Signal, Reddit, Discord, Pinterest, Facebook, WhatsApp Banking & Finance: Lloyds Bank, Halifax, Bank of Scotland, Barclays, Venmo, Coinbase, Xero, Chime Retail & eCommerce: Amazon, Amazon Alexa, Amazon Music, Prime Video, DoorDash, Grubhub, Afterpay, Eventbrite, Starbucks Entertainment & Media: Netflix, Hulu, Apple TV, The New York Times, Disney Gaming: Fortnite, Roblox, Epic Games Store, Clash Royale, Pokémon GO, PlayStation Network, Xbox Fitness & Wellness: Peloton, My Fitness Pal, Strava, Life360 Productivity & Business Tools: Canva, Zoom, Slack, Jira Software, Asana, Smartsheet, Microsoft 365 Technology & AI: AWS itself, Perplexity AI, Ring, Blink Security, Roku Telecommunications: BT, Virgin Media, EE, Sky, T-Mobile, Verizon Travel & Transportation: Lyft, National Rail Government: HMRC (UK Tax Service), Gov.uk Many of these services rely on AWS infrastructure for multiple backend functions, so a single outage caused ripple effects throughout each industry. This outage yet again exposes just how fragile the online infrastructure is!

"AI will replace every SDR/BDR within the next 12 months." On a GTM Mastermind last week, someone said this to me. Coincidentally, someone else told me this exact same thing 6 months ago, and 6 months before that… This kind of talk does nothing to sell these new solutions. Just like SaaS, these tools might help a lot but they will only help salespeople be better at the job, they won't replace salespeople. It's time we stop talking about AI like it's going to take everyone's jobs. Technology gets replaced but people don't.