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Hey Product Fans!

Welcome to this week’s 🌮 Product Tapas!

If you’ve been forwarded this or just stumbled upon it, you’re in for a treat. For the best reading experience, check out the web version and sign up for future editions here.

I'm writing this from gloriously sunny Turkey this week ☀️, but don't worry, I'm still tracking all the chaos so you don't have to!

📰 Not Boring:The productivity wars are heating up as Grammarly snaps up Superhuman, whilst Cursor's pricing drama shows even the hottest dev tools aren't immune to growing pains. Meanwhile, the AI talent shuffle continues with moves that make Premier League transfers look tame, and Meta's dropping$3.5 billion on eyewear because apparently your face is the next frontier.

⌚️ Productivity Tapas: This week's lineup includes a ChatGPT-Slack hybrid that'll change how you think about AI interfaces, plus tools that let you build App Store-ready mobile apps just by chatting. Perfect for those "I wish there was an app for that" moments.

🍔 Blog Bites: Ben Thompson delivers a reality check on Big Tech's AI positioning (spoiler: Meta's in more trouble than you think), Tim Herbig shows why most product discovery is just expensive procrastination, and how Superpower built a 150k waitlist by putting distribution before product.

🎙️ Pod Shots: Andrew Wilkinson drops wisdom from 75 businesses on why boring beats flashy every time, plus the (yes clichéd, but very relevant) truth about why billions didn't make him happier.

Ready to dive in? Let's go! 🚀

📰 Not boring

AI Productivity Land Grab

• Grammarly acquires AI email client Superhuman. The productivity suite wars are heating up, with everyone racing to become the AI-first version of whatever they used to be. Hot on the heels of Airtable's pivot, we're watching the great unbundling and re-bundling of productivity tools in real time

• Cursor now available on Web and Mobile

  • Although a recent pricing change sparked a developer exodus and forced a quick U-turn. Nothing says "we're still figuring this out" like having to backtrack on pricing within weeks of a major launch

• Anthropic announces Desktop Extensions: One-click MCP server installation for Claude Desktop

  • Meanwhile, Amazon has quietly become the global leader in MCP. The infrastructure layer always wins, even when nobody's paying attention

Big Tech Chess Moves

• Ilya Sutskever becomes CEO of Safe Superintelligence after Meta poached Daniel Gross. The AI talent shuffle continues. At this point, tracking who's where feels like following Premier League transfer windows, but with higher budgets and more existential dread

• Meta Invests $3.5 Billion in world’s largest eye-wear maker in AI Glasses push. Not content with buying all the top AI resource in the world, Meta's now going after your face. The AR future is expensive, apparently

• Google brings Gemini to Wear OS watches, adds AI Mode to Circle to Search. Google's strategy seems to be "put Gemini everywhere and see what sticks."

The Chaos Corner

• Samsung seems to have leaked its own trifold phone design

• From @ns123abc YC startup drama: A company claimed they built a cheating tool in 4 days, but actually stole it from an open-source project called "Cheating Daddy," which is itself a clone of Cluely (the$15M a16z-backed cheating tool we mentioned last week) - The cheating tool ecosystem is apparently both thriving and completely incestuous. Peak “Silicon Valley”

• Jack Dorsey launches a WhatsApp messaging rival built on Bluetooth

The Rest

• Neobank Revolut seeks $65B valuation, a year after its $45B deal. That's a 44% bump in 12 months

• Redditors are sharing ways to make ChatGPT atop agreeing with everything you say

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⌚️ Productivity Tapas: Time-Saving Tools & GPTs

• Tidbit: “Like Slack and GPT had a baby.” ChatGPT but with a Slack type interface

• Tile: Build and ship App Store ready mobile apps with AI agents. Chat to edit, Agents handle auth, payments, CMS & more

• TensorBlock Forge: fast, secure way to connect and run AI models across providers via API

Remember, as a Product Tapas Pro subscriber you can access the full time saving tools database for fast approaching 400 time-saving tools relevant for product managers and founders 🔥.

Check the link here to access.

🍔 Blog Bites - Essential Reads for Product Teams

AI Strategy: The Big Five's AI Reality Check After 2.5 Years

Ben Thompson revisits his landmark 2023 analysis of how Apple, Google, Meta, Microsoft, and Amazon are positioned for the AI epoch, revealing some big shifts in competitive dynamics and strategic positioning. Triggered by Meta's apparent crisis and Zuckerberg's desperate talent acquisition spree, Thompson reassesses each company's infrastructure, models, partnerships, and business model implications in the current AI landscape. Read the full article here.

💡 "Meta's struggles to develop cutting-edge artificial-intelligence technology reached a head in April, when critics accused the company of gaming a leaderboard to make a recently released AI model look better than it was."

Product Discovery: The Three-Level Triangulation Framework

In his most recent post, Tim Herbig introduces a structured approach to Product Discovery that helps teams move beyond broad user research to targeted, strategic insights. By applying three levels of decision-making criteria, product teams can avoid "Alibi Progress" and focus their discovery efforts on what truly matters for business impact. Read the full article here.

💡 "Just because a user (segment) has a problem doesn't mean that you have to prioritise solving it. Instead, weigh the lever of the segment against what you're trying to achieve."

Growth Strategy: How Superpower Built a 150k Waitlist Through Distribution-First Thinking

Max Marchione, co-founder of Superpower, reveals the systematic approach behind building a 150,000-person waitlist in just six months for their longevity platform. By embracing a "distribution-first, product-second" philosophy, Superpower created a hype engine through viral mechanics, strategic brand positioning, and creative marketing drops that generated massive anticipation before product launch. Read the full article here.

💡 "In 2025, we're seeing a paradigm shift in company building: distribution first, product second. The traditional startup playbook – build product, find product-market fit, then scale marketing – is becoming outdated."

🎙️ Pod Shots - Bitesized Podcast Summaries

Remember, Product Tapas Pro subscribers get access to an ever growing database of all the top Podcast summaries we’ve ever created. 

Check it out here

🎯 The 75-Business Playbook: Why Boring Ideas Beat Flashy Ones Every Time

Andrew Wilkinson has started or been involved with 75 different businesses. As co-founder and CEO of Tiny—the "Berkshire Hathaway of the internet"—he's built a holding company worth hundreds of millions by buying profitable businesses and holding them long-term (and you’ve probably never heard of him…). But his journey from barista to billionaire (and back) taught him counterintuitive lessons about what makes businesses succeed and what actually creates happiness.

I like this episode mostly because Wilkinson shares his hard-won insights about finding great business ideas, and why boring beats flashy. Plus he also covers how AI is transforming work, and why money didn't solve his problems—but medication did.

 🎥Watch the full episode here

📆 Published: July 4th, 2025

🕒 Estimated Reading Time: 3 mins. Time saved: 94 mins🔥

🎣 Fish Where the Fish Are: The Charlie Munger Principle

Wilkinson's best advice for startup ideas comes from Warren Buffett's partner Charlie Munger: "Fish where the fish are." The metaphor is simple but profound—if you see a pond surrounded by fishermen with the best equipment all competing for the same fish, walk into the forest and find a small fishing hole with lots of fish and little competition.

"Almost nobody wakes up every morning and says, 'You know what? I'd love to start a funeral home,' or 'I would like to start a pest control business,' or 'I should start software that helps people fill out forms for the government,'" Wilkinson explains.

He contrasts this with businesses everyone thinks about—restaurants, cafes, cool apps—where millions of people have the same idea. Competition equals lower margins, and the more competitors there are, the lower your prices have to be.

Key Takeaways:

• Boring industries often have better economics than exciting ones

• Competition is inversely correlated with profitability

• The best opportunities are where few people want to compete

🏋️ Start with Baby Weights: Why First-Time Entrepreneurs Should Think Small

Wilkinson uses a gym analogy to explain why new entrepreneurs should start small: "You don't want to walk into the gym on day one and try and deadlift 300 pounds." When someone tells him they want to start "the next great AI company" or launch a new bank, he sees it as the equivalent of attempting that 300-pound deadlift.

His first business—a web design agency—was perfect for a beginner. All he needed was the ability to build websites and talk to customers. When they said yes to $5,000, he sent an invoice, did the work, and got paid. Simple.

"Because of that, I got immediate positive feedback and I built my own narrative. And my narrative was, 'I'm good at business, I can do this, keep going,'" he recalls.

Key Takeaways:

• Choose businesses where you can get quick wins and positive feedback

• Simple business models are better for learning the fundamentals

• Early success builds confidence for tackling bigger challenges later

💀 Learning from Dead Bodies: Why Some Ideas Always Fail

One of Wilkinson's biggest insights is recognizing patterns of failure. "The biggest mistakes I've made have been going into business models where other people have repeatedly failed and thinking, I can do this better."

He learned this lesson the hard way with a bar he started with a friend. Despite being "tech guys" who thought they could build better systems, they were humbled by the operational complexity. "If you think about it, like my example earlier of if you run a software company, what has to happen? You have to hire a bunch of nerds, they need internet connections and computers... A pizzeria, it's like if the baker doesn't wake up at three in the morning and start prepping dough, the entire thing is effed."

Key Takeaways:

• If there are dead bodies in a space, understand why they died before entering

• Don't assume you can fix a fundamentally broken business model with better management

• Operational complexity often kills businesses that look simple from the outside

🤖 The AI Revolution: From Palm Treo to iPhone Moment

Wilkinson is deeply embedded in the AI transformation, using tools like Lindy.ai to automate much of his work. He's built agents that manage his email, calendar, and even relationship conflicts (using Limitless to record conversations and get AI coaching on how to communicate better).

"It's like having the world's most reliable employee who costs $200 a month and works 24/7," he says about his AI setup.

But he sees current AI tools as being in the "Palm Treo phase"—powerful for early adopters but not yet accessible to everyone. The iPhone moment will come when anyone can open ChatGPT and say, "I run a business, can you help me?" and get a fully functional digital employee.

Key Takeaways:

• AI is already replacing knowledge work jobs (researchers, assistants, translators)

• Current tools require technical skill but will become more accessible

• The next 5 years will see massive job displacement in knowledge work

💰 The Happiness Paradox: Why Billions Didn't Fix His Brain

Perhaps Wilkinson's most powerful insight comes from his journey with wealth and mental health. Despite reaching billionaire status, he remained anxious and unhappy. "I remember a month ago, I had this day where I was sitting in the sauna and I was stressing about a bunch of business problems... 10 years ago I had all the same thoughts and I was stressed out about similar kinds of problems and our revenue was $20 million bucks... Now we're at almost 300 million and I'm still stressed about the same things."

The breakthrough came not from more money, but from addressing his mental health directly. Getting diagnosed with ADHD and starting an SSRI transformed his life more than any business success.

"No amount of money or success or attention or anything else had done what this little tiny yellow pill could do for my mental state," he reflects.

Key Takeaways:

• Wealth doesn't solve internal anxiety or depression

• Mental health issues are medical problems that often require medical solutions

• Even billionaires compare themselves to their peers and feel inadequate

🎯 The Moat Strategy: What Makes Businesses Unbreakable

When buying businesses for Tiny, Wilkinson looks for companies that are "so good that it's hard to mess up." He focuses on businesses with strong moats—competitive advantages that make them difficult to disrupt.

The best moats he's found are:

• Network effects: Communities so large that users won't leave (like Letterboxd, their film social network)

• Strong brands: Pricing power through customer loyalty

• High switching costs: Though he notes this is "more depressing" as it's not consumer-friendly

Recent acquisitions include Serato (DJ software with deep hardware integration) and AeroPress (the coffee maker company), both businesses where his personal interests aligned with strong competitive positions.

Key Takeaways:

• Look for businesses that are hard to compete with, not just profitable

• Network effects create some of the strongest moats

• Personal knowledge of an industry provides unfair advantages in evaluation

🧠 The ADHD Entrepreneur Connection

One of Wilkinson's most surprising discoveries was learning he had ADHD at age 30+. Despite being organized and successful, cognitive testing revealed severe working memory issues. This led to a broader realization: while only 5% of the general population has ADHD, about 30% of entrepreneurs do.

"Many entrepreneurs I talk to, they love new things. They love jumping around between a million different topics. They're an inch deep and a mile wide like I described. And they describe themselves as unemployable."

Getting diagnosed and treated didn't just help his work—it transformed his personal relationships by helping him understand why he'd forget simple tasks like taking out the garbage.

Key Takeaways:

• ADHD is significantly overrepresented among entrepreneurs

• Many successful people have undiagnosed conditions that affect their lives

• Understanding your brain's wiring helps in both business and relationships

🔄 Bootstrap vs. Venture: It's Not About Size, It's About Tolerance

Wilkinson challenges the false dichotomy between "lifestyle businesses" and venture-scale companies. Tiny has grown to nearly $300 million in revenue while remaining bootstrapped. The difference isn't potential size—it's tolerance for burning money.

"I think the only difference between what we do and what a venture capitalist does is the level of tolerance of burning money on fire," he explains.

The decision comes down to your goals. If you want to start a satellite business requiring massive upfront investment, you need venture capital. But if you're solving a problem that doesn't require lighting millions on fire before generating revenue, you can build a wonderful, scalable company without ever raising money.

Key Takeaways:

• Bootstrap businesses can scale to hundreds of millions in revenue

• The choice depends on capital requirements, not ambition

• Many successful businesses grow naturally without needing to burn cash

🎪 The Future of Work: From Knowledge Work to Human Connection

Looking ahead, Wilkinson sees a world where most knowledge work becomes automated, but new types of jobs emerge around human connection and experience. He points to OnlyFans as an early example—people paying for comfort and connection.

"Imagine people did that day to day, they just love hanging out with funny people. So you have a funny guy who you chat with or comes over to your house... Maybe it's a guy who comes to play pickleball with you."

His advice for navigating this transition: get incredibly good with AI tools and use them to build wealth that can be diversified into compute and energy. The window for this opportunity may be longer than people think, as robotics will take time to handle physical tasks.

Key Takeaways:

• Knowledge work jobs will be heavily impacted by AI

• New jobs will emerge around human connection and experience

• Physical world tasks will remain human-dominated longer than digital ones

🎯 The Lazy Leadership Philosophy

Throughout his journey, Wilkinson has developed what he calls "lazy leadership"—systematically removing himself from tasks he hates. Whether through AI automation, hiring, or business design, the goal is to focus only on what energizes him.

"How do I get away from the things I hate as quickly as humanly possible? How do I be Teflon for tasks?" he asks.

This philosophy extends to hiring: he looks for people who are already fully formed and can do what's needed, rather than trying to coach people into new roles. "I've never been able to change someone. You can never mentor someone out into being a good employee."

Key Takeaways:

• Design your role around what you love, not what you think you should do

• Hire for what you need now, not potential

• If you're thinking about firing someone, you probably should

Andrew’s journey is a great listen (which Lenny Podcasts aren’t??). His insights about finding boring opportunities, building moats, and using AI tools are all decent takes for the next generation of entrepreneurs. But perhaps his most interesting lesson (and yes it’s a cliche) is that success without addressing your internal state is hollow—and that sometimes the most important breakthroughs come not from business strategy, but from understanding and caring for your own mind. 🧘‍♂️ 

 🎥Watch the full episode here

📅Timestamps:

• (00:00) Introduction to Andrew Wilkinson

• (04:07) Finding the right business idea

• (07:18) Avoiding common business pitfalls

• (11:58) Finding your unfair advantage

• (17:08) Fish where the fish are

• (20:08) Why boring is good

• (25:30) Bootstrapping vs. venture capital

• (31:20) Lessons from acquiring and managing businesses

• (36:47) Avoiding people problems

• (42:39) Leveraging AI in business and life

• (49:30) The Limitless device

• (53:13) Job displacement and AI’s future impact

• (58:20) Advice for new grads

• (01:02:50) Parenting in the age of AI

• (01:05:26) The pursuit of happiness beyond wealth

• (01:10:10) Mental health and medication

• (01:16:45) Lightning round and final thoughts

Referenced: 

• Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/12656... • Metalab: https://www.metalab.com/ • Letterboxd: https://letterboxd.com/ • AeroPress: https://aeropress.com/ • Brian Armstrong on X: https://x.com/brian_armstrong • Warren Buffett’s quote: https://quotefancy.com/quote/931119/W... • Flow: https://www.getflow.com/ • Instacart: https://www.instacart.com/ • Things: https://culturedcode.com/things/ • Dustin Moskovitz on LinkedIn:  • Salesforce: https://www.salesforce.com/ • Serato: https://serato.com/ • Chris Sparling on X: https://x.com/_sparling_ • Lindy: https://www.lindy.ai/ • Replit: https://replit.com/ • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/be... • David Ogilvy: https://en.wikipedia.org/wiki/David_O...) • Malcolm Gladwell’s website: https://www.gladwellbooks.com/ • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/in... • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/bu... • Limitless: https://www.limitless.ai/ • Perplexity: https://www.perplexity.ai/ • Claude: https://claude.ai/ • ChatGPT: https://chatgpt.com/ • Gemini: https://gemini.google.com/app • William Gibson’s quote:   / the-future-is-already-here-it-s-just-not-e...   • Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo

That’s a wrap.

As always, the journey doesn't end here!

Please share and let us know what you would like to see more or less of so we can continue to improve your Product Tapas. 🚀👋

Alastair 🍽️.