Jimmy Lin

Are you building features or driving outcomes? In this week's Product Thinking Podcast, we revisit my conversations with Jose Quesada from American Express and Matthew Skelton, co-author of Team Topologies, to talk about structuring teams around value. One thing Jose said that I believe is key: "You need to start with the outcome you want to drive, rather than the thing you want to do." Most teams skip this step. They jump straight to "we're building a recommendation engine" instead of asking "what are we trying to achieve?" When you start with an outcome (like increasing repeat purchase rate by 20%), you open up multiple paths to get there. Maybe it's a recommendation engine. Maybe it's improving the checkout flow. Maybe it's better email personalization. Starting with a solution locks you in before you understand if it's the right one. Teams that lead with outcomes make better decisions, get clearer stakeholder alignment, and avoid the build trap. Teams that start with solutions end up measuring success by what they shipped, not what they achieved. The fix requires discipline: define the outcome first, immerse yourself in the data, form your hypotheses, then figure out the how. Your features should be answers to outcome-driven questions, not the starting point. How does your team approach discovery? Outcomes first, or solutions?

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Brian Balfour shared a blueprint for understanding the scale of change ahead. Here's the M&A POV for the AI column: Development Methodology: Acquirers don't care much about your new revolutionary process. They care if your team has a constant framework for automation and AI. Tools: AI infrastructure companies are the real strategic targets. AI apps and basic tools, not so much. Monetization Models: Traditional "6x recurring revenue" multiples become irrelevant in AI deals. AI companies get acquired for their potential to unlock value in the acquirer's ecosystem. Growth Models: AI companies don't follow traditional growth playbooks. The uncertainty creates arbitrage opportunities for strategic buyers. Measures of Success: The metrics are undefined because AI value creation is still emerging. This benefits companies that can "craft a narrative" around strategic value. Defensibility: Acquirers want to buy before defensibility gets established and prices go up. Build strategic relationships as early as possible to be on their radar. Skillsets & Roles: Companies are buying teams that "can handle the next generation" of AI. The talent scarcity makes these acquisitions strategic necessities. Team & Org Design: AI companies should be molded to fit the acquirer's vision. This flexibility commands strategic premiums from buyers. The current undefined nature of AI creates strategic value that can't be benchmarked against traditional multiples. Startup founders can take advantage of that. i5growth / i5invest: Investment Fund, global tech M&A arm, team of 100+, offices in San Francisco, Vienna, Madrid, Berlin, Frankfurt; 200+ exits & strategic partnerships with tech leaders such as Google, Microsoft, Salesforce, Qualcomm, Samsung, Nvidia, Naspers, NBC, … #strategy #startups #growth #i5growth #i5invest Image by Brian Balfour

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Pop quiz: Who hasn’t heard that "90%+ of AI projects flop" stat dropped at every tech meet or biz panel lately? It’s constantly recycled. But after deep dives with execs and teams across manufacturing, finance, and retail, a different story’s emerging. The real threat isn’t failure—it’s missing the sweet spots where AI can *actually* deliver transformation. Take manufacturing as an example. Many leaders go through rounds of flashy AI tools—smart chatbots, next-gen dashboards—only to realize these don’t solve their real pain points. One company, for instance, processed 10,000 invoices by hand every month. The real breakthrough? Targeted, straightforward finance automation that started saving $40K monthly. The lesson: Instead of chasing shiny tech, start by mapping your workflow wastelands and focus on problems that matter. Too many organizations get swept away by buzz—promises with little real context. What derails most projects isn’t actually the technology. It’s organizational chaos: launching projects without fully understanding what’s broken, security issues, disorganized data, missing skills—classic case of buying the latest tool without first checking if you truly need it. A sound process looks like this: • Map every workflow, no exceptions • Measure every resource drain in time and money • Isolate the critical bottlenecks • Build a clear, stepwise plan for transformation When done right, this flips the monthly ledger: losses turn into measurable gains. Suddenly, ROI is clear—trackable, defensible, and rooted in the business. Nearly half of companies abandon more AI projects than they complete (S&P Global). 90% don’t manage their data effectively (TechRadar). According to RAND, about 80% of failures stem from gaps in planning and organizational culture—not the code. The pattern: Failure is usually procedural. Most teams chase hype, buy before measuring, and apply AI to symptoms, not the root causes. The high-return sequence is: • Hunt for high-impact wins before building solutions • Set a roadmap with clear milestones and accountability • Integrate AI where the ROI is unmistakable and your governance is ready Organizations that succeed with AI are highly disciplined: they prioritize bottlenecks, obsess over data quality, build team capability, and resist distractions until the numbers add up. They know exactly *where* and *how* AI will impact their P&L. It’s not luck—it’s strategy. For me, having helped launch AI-focused solutions, one lesson repeats: The “failure rate” isn’t doomsday—it’s a guide. Ignore the hype, focus on measurable, real-world value. The hidden ROI isn’t in the AI itself. It’s in the overlooked workflows within your business. Audit thoroughly, cross every division, and measure every gap: odds are, untapped opportunities are waiting. #AI #Automation #DigitalTransformation #BusinessGrowth #ProcessImprovement #FutureOfWork #Startups #Innovation

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I’ve been talking with founders about how painful enterprise customization still is — even in 2025. David Dworsky and Gordon Ritter just put words to what we’ve been seeing: the age of point-and-click configuration is ending, and the next category winners will make customization conversational. For early-stage founders, this is the wedge: - Own one painful workflow - Capture the data - Build toward becoming a system of record If you’re building in this space, I’d love to hear how you’re approaching it. Link to the full article on this in the comments. 

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If ChatGPT and Netflix had a baby, it would look like a Navless.ai website. Companies like wisetail.com (Wisetail, an Intertek Company) are educating more visitors, faster with Navless:

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82% of small business failures aren't about bad ideas. They're about running out of cash while building great ones. The SBA data is clear: cash flow mismanagement kills more businesses than product-market fit issues. Yet most solopreneurs I see tracking through AI tools focus obsessively on revenue growth while ignoring the metrics that predict survival. Here are the three numbers you should review every single week: **Operating Cash Flow Ratio** This tells you if your operations generate enough cash to cover current obligations. Calculate it by dividing operating cash flow by current liabilities. Anything below 1.0 means you're burning faster than you're earning. **Cash Runway** Take your current cash balance and divide it by your average monthly burn rate. This number tells you exactly how many months you can survive at your current spending level. If it's under 6 months, you're in the danger zone. **Receivables Aging** Track how long it takes customers to pay you. Money promised isn't money you can spend. If your average collection period creeps past 45 days, you're funding your customers' operations with your survival budget. The pattern is always the same: businesses that monitor these three metrics weekly make different decisions than those who check their bank account when it's too late. Set up a simple spreadsheet. Block 15 minutes every Monday. Calculate these three numbers. Let the data guide your decisions before emotions do. What financial metric has saved your business from a close call? #SolopreneurLife #SmallBusinessFinance #CashFlowManagement #EntrepreneurTips #BusinessGrowth

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What's the real cost of unresolved tech risk in M&A? We worked with a $50M ARR SaaS founder who discovered—three weeks before closing—that his platform had critical vendor lock-in dependencies and undocumented hosting cost sensitivity. The investor's valuation dropped by $8M. The deal almost died. Here's what happened: nobody had mapped the commercial & integration considerations. Nobody understood the true capex requirements. Nobody had quantified the value leakage from operational fragility. This is exactly what our Investor-Grade IT Due Diligence audit prevents. We identify: ✓ Hosting cost sensitivity to growth ✓ Vendor lock-in risks ✓ Integration or carve-out complexity ✓ Post-acquisition investment requirements ✓ Value-impact mapping (ARR, churn, margin exposure) 4-8 weeks. One comprehensive report. Millions protected. Let's talk: denny.burda@riveconsultancygroup.co.uk

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Your product has traction. Revenue is growing. But your GTM systems are duct-taped together—and it’s starting to show. This is where most early-stage teams stall: 🚫 No clear funnel 🚫 Broken handoffs 🚫 Metrics you can’t trust We put together a playbook to help founders build GTM infrastructure that actually scales. Here’s the breakdown 👇

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We recently brought in George Berger to consult on graphics and branding for a SaaS platform we're building. The product’s still under wraps, but his impact isn’t—George brings clarity, precision, and 20+ years of design expertise to the table. We’re in tech. We understand what AI can do—and what it can’t. When it's useful and when it's not. Authentic visual identity doesn’t come from a model. It comes from someone who knows how to translate ideas into meaning. Your business is too important to settle for generic, AI-generated design. Don’t phone it in. Your work shouldn't be template-based. It should be intentional, human, and built to last. Work with George and get it done right. http://www.artofgvb.com

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Two years ago I met Damien Howley through the local Charlotte GTM community. We instantly aligned philosophically on the existential challenges facing the SaaS industry today. Why would enterprises still opt to “buy” when they can now “build” their own fit-for-purpose solutions at a fraction of the cost with AI and not have to deal with a vendor’s BS? But more critically… what does this new buyer-empowered era mean for startups, scale ups, and enterprises building and selling software B2B? What emerged after numerous late night conversations across time zones was a thesis: in order to justify existing in the AI era, software companies MUST regain their purpose… solving their customer’s biggest business challenges. We have way over indexed on specialization and forsaken effectiveness for the allure of “efficiency”. What does mean in practice? Siloes. Siloes. Siloes. Siloes. Siloes. And guess who feels that the most? Your customer. This is the reason churn has increased dramatically over the last 12 months. Customer experience has now become a chop shop of connecting disparate experiences across a GTM “journey”. Sales hand off to Services hand off to CS providing feedback to Product who prioritizes across Sales Services and CS while updating Marketing on how to talk about product to Sales… and it’s way more confusing than that, going on and on and on. … fast forward 12 months and Damien has published the ANSWER to this incredibly thorny problem. It’s called The Purpose Code and you’ve got to give it a read. If you are in GTM writ large for tech companies (Product, CS, Sales, Marketing, Exec), this is your guide for how to navigate the chaos of the world today and help your organization regain its true PURPOSE. Very grateful to have been able to play a part in the development of this book. Also very grateful to have met you along this crazy journey of starting a company Damien. Thank you for your friendship, intellectual sparring, and for sharing the most important message that technology leaders across business need to hear.

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