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What to Look For Before You Buy a Business
Most buyers start with revenue and margin. Start instead with whether the business is good or broken, then ask four questions about the owner, the demand, what’s been neglected, and the team.

Matt Pisoni
4 days ago2 min read


Grok Bot vs. Claude Cowork: The AI Future Is Not One Super-Assistant, It's an AI Team
Grok Bot and Claude Cowork are two different bets on how AI gets work done — a roster of persistent teammates vs. a single agentic workspace. Here's how they compare, and what it means for operators putting either to work.

Matt Pisoni
Sep 187 min read


The Unglamorous Version of AI
Most talk about AI focuses on flashy new capabilities, but real business value lives in unglamorous operational wins. It’s found in a dispatch desk routing jobs in two minutes instead of fifteen, or overnight quotes sent within the hour. The biggest opportunities aren't about reinventing your strategy; they're about target-fixing repetitive tasks, organizing trapped institutional knowledge, and resolving long-ignored workflow bottlenecks to directly boost your bottom line.

Matt Pisoni
Sep 172 min read


Three Questions to Ask Before You Ever Look at the Financials
Owners considering a sale often prepare for the moment a buyer opens the books. That moment matters, but by the time it happens, most of your view of the business should already be formed. It comes from three questions worth asking early, in conversation, before anyone pulls up a spreadsheet. 1. "What do you wish you'd had time to fix?" Every owner running a business day-to-day has a mental list of things that annoy them — a process that's clunky, a system that's outdated, a

Matt Pisoni
Sep 142 min read


Nvidia's $500B Bet to Turn GPUs Into an Asset Class — What Would Have to Go Right?
An operator's questions about Nvidia's reported $500B compute financing plan — what has to be true for it to work, and what happens if demand doesn't show up.

Matt Pisoni
Sep 32 min read


Why Psychedelic Use Is Increasing—and Why the Conversation Is Finally Getting Interesting.
An observational take on why psilocybin, ketamine, and ayahuasca are moving from fringe conversation to serious discussion—and why the science deserves more respect than the hype.
A few years ago, mentioning psychedelics in a business conversation would have changed the temperature in the room.
Someone would suddenly need more coffee. Someone else would become fascinated by the floor. And one person—usually the guy who once spent a semester “finding himself” in Boulder—woul

Matt Pisoni
Aug 235 min read


Seattle Layovers With My Brother: How to Turn 18 Hours Into a Full Summer Vacation
Almost every year, usually on my way to or from Hawaii, I try to stop in Seattle to visit my brother Sean. The layovers range from 6 hours to 18 hours and occasionally 24. This most recent stop was 18 hours, bookended by a redeye from Hawaii to Seattle and another redeye from Seattle back home. We walked roughly eight miles, grabbed scooters and e-bikes whenever it made sense, wandered through neighborhoods, stopped at coffee shops, ate tacos from food trucks, sampled beer,

Matt Pisoni
Aug 213 min read


Prosecutorial Misconduct and the Justice System’s Incentives Problem
Prosecutorial misconduct is rarely just about bad actors—it’s about bad incentives. While most prosecutors strive to act ethically, the justice system often rewards convictions and case volume over restraint. With low accountability, hidden evidence, and immense pressure on defendants to accept plea deals, the system can end up prioritizing wins over true justice. Real reform requires shifting these underlying incentives toward transparency, strict disclosure, and genuine acc

Matt Pisoni
Jul 234 min read


When It Stops Feeling Like Justice and Starts Feeling Like a Win‑at‑All‑Costs Game That You Are Stuck In.
What started as an investigation slowly became a saga. The process stretched on for years. Allegations were repeated as if they were facts. Nuance disappeared. The story hardened: there were “good guys” and “bad guys,” and I was placed in the second category long before all the evidence was heard. The longer it went on, the more it felt like momentum mattered more than accuracy.

Matt Pisoni
Jul 113 min read


The New Era of Local SEO: How Google Gemini is Transforming Your Business Profile
If you run a local business, you already know that your Google Business Profile (GBP) and your Google Maps listing are critical assets. For years, they have served as the digital storefront of your operation, driving foot traffic, phone calls, and website visits. But recently, Google has fundamentally shifted the landscape. Your business profile is no longer just a passive listing for human eyes; it has become the core dataset feeding Google’s artificial intelligence ecosyste

Matt Pisoni
Jun 185 min read


Claude Cowork: Your Delegated Operator
Claude Cowork isn’t just another chatbot bolted onto your workflow. It behaves like a delegated operator that can own real processes end to end: tracking documents, updating dashboards, and surfacing decisions your team actually needs to make. In this post, I break down how Cowork fits into a modern operating system for your business and where it already outperforms ad hoc prompting.

Matt Pisoni
Jun 153 min read


Perplexity Computer: Powerful, Expensive, and Closer to an AI Employee Than a Chatbot
Perplexity Computer is not just another chatbot window. It is a cloud-based AI “employee” that can research, call tools, and complete multi-step work from a single prompt. Instead of stopping at an answer, it runs workflows in a sandboxed environment and reports back, which makes the real question less “Can it reply?” and more “What work can it actually take off your plate?”

Matt Pisoni
Jun 152 min read


Google Personal Intelligence: When Your Inbox Becomes Your Second Brain
Once an AI can reason across multiple sources of your personal context, it starts to feel less like software and more like an assistant that has been quietly paying attention.

Matt Pisoni
Jun 94 min read


Hesitant to post because you’re worried you’ll come off like a wannabe influencer?
Most people have heard they “need a personal brand.” Usually, that advice comes wrapped in images of someone recording videos in their car or posting nonstop about their daily routine. If your reaction is that this isn’t you and you don’t have time for it, you’re not wrong. So you ignore it—and meanwhile, someone no more skilled than you keeps getting the call. What often gets missed is this: a personal brand isn’t a performance. It’s simply your professional reputation made

Matt Pisoni
Jun 23 min read


Give AI the First Shot (And Stop Doom‑Scrolling “This Changes Everything” Threads)
“Pretend to be a skeptical customer, a CFO, and a competitor. Roast this.”
It happily obliges, surfacing pricing questions, trust issues, and “this sounds like buzzword soup; what problem does it solve?” style feedback.
Is some of it overdramatic? Sure. But it’s cheaper than learning all of that live in front of a room of humans.

Matt Pisoni
May 225 min read


All Rise: A Book, a Friend, and a Blueprint for Rising Through It.
And critically, she introduced me to the attorney I would eventually hire for my post-trial proceedings: David Markus. David is everything you want in a lawyer when the stakes are real. He is focused, vigilant, and — in the best possible way — aggressive. He doesn't coast. He doesn't hedge. He fights for his clients with a precision and intensity that you feel from the very first conversation. Having him in my corner made a difference, and I owe that introduction entirely t

Matt Pisoni
May 203 min read


How to Avoid Scams Online: A Practical Guide for Everyday Users
Understanding the most frequent scams is your first line of defense:
Phishing emails or texts that impersonate banks, delivery services, or government agencies.
Fake websites that mimic real companies to steal login or payment information.
Online shopping scams offering deals that seem too good to be true.
Tech support scams claiming your device is infected and demanding payment.
Investment or cryptocurrency scams promising guaranteed high returns.

Matt Pisoni
May 192 min read


Why Fujairah Became the New Front Line in the Gulf
The broader conflict is about economic sovereignty, energy pricing, and the ability to shape the region’s future. Reporting in late April said the UAE planned to exit OPEC and OPEC+ on May 1, a move tied to giving Abu Dhabi more freedom over production policy and its long-term energy strategy. With the capacity to push output higher, the UAE is positioning itself to compete on volume, while Iran—constrained by sanctions—needs oil prices to stay elevated to support its economy

Matt Pisoni
May 62 min read


Scaling from $200M to $1B: What It Really Takes
But even that wasn’t enough.
Because you can’t scale a business without scaling trust. As the team grows, communication naturally becomes more complex. Silos start to form. Misalignment creeps in. If you don’t actively build a culture of teamwork and trust, growth will stall—or worse, collapse under its own weight. We had to be intentional about culture. Not as a slogan, but as a daily practice. Having your core values posted on the wall, but not treating people with respect

Matt Pisoni
May 62 min read


AI Search Is Rewriting the Funnel
I keep seeing the same pattern: performance feels harder to scale because the search journey is changing before the click even happens. Users are no longer behaving like they used to, and AI search tools are reshaping the moment where decisions begin.

Matt Pisoni
Apr 272 min read
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