Business + Tech + Investing
Every generation of cheap content invents its own watermark. Every watermark eventually gets a workaround. Here s the twenty-year pattern hiding inside this week s AI news. In this post: I read a thread this week from the CTO of GPTZero explaining how Anthropic, Google, and OpenAI actually watermark AI text. Not the marketing version. The real [ ] The post Plagiarism appeared first on Keith Brown…
I spent the last few days building using some of the latest AI tools and models. Nearly didn t sleep, seriously. Was up for nearly 24 hours straight, building out several working prototypes at the same time. It was a big mental shift from what I m used to. Instead of planning out a quarterly roadmap that [ ] The post Two Loops appeared first on Keith Brown .
Was catching up with a founder of an early stage software company last week over coffee. They recently launched a big outbound marketing campaign. It sounded great at first. They integrated three separate autonomous AI agents to scrape LinkedIn, write personalized emails, and handle follow-ups. They sent 100,000 hyper-targeted emails in 30 days. The result? [ ] The post Double Down on Humans…
The insights, analysis, and data presented in this article are for informational and educational purposes only and do not constitute financial, investment, legal, or tax advice. Always conduct your own independent due diligence before buying or selling any security. I was catching up with the founder of CostHawk recently, asking him what he s seeing in [ ] The post Anthropic Whales appeared first…
There is an iconic scene in Moneyball where Billy Beane sits at a drab boardroom table, completely surrounded by old-school baseball scouts. They are debating subjective aesthetics, tracking useless legacy data points, and bloating the payroll with players who look the part. Billy realizes the entire industry is playing a legacy game. The goal isn t [ ] The post Builders or Growers appeared first…
There is a scene in Jaws where the shark finally shows itself, and Brody famously says, You re gonna need a bigger boat. He was wrong. They didn t need a bigger boat. They needed a crew that could actually move. Jaws was an AI-native team. It sounds silly, but if I haven t lost you yet, read [ ] The post The New Exec Team appeared first on Keith Brown .
Over the last six months, I’ve spoken to more than a dozen executives at mature, established software companies. Every single one of them is facing the exact same existential threat. Legacy SaaS is now a dirty word. And it gets worse. Customers at these legacy SaaS companies are looking at their platforms and asking a [ ] The post The Legacy SaaS Premium appeared first on Keith Brown .
I have spent the last twenty years of my life in the SaaS trenches. I love this industry. I love the expansion revenue, the predictable seat counts, and the way software used to solve every problem by adding more humans to a platform. I have seen the SaaS 1.0 era turn into a gold rush, [ ] The post The Last Castle appeared first on Keith Brown .
Software used to be hard. We paid Alpha Engineers like professional athletes because they were the only ones who could turn a vision into a functional machine. For a decade, the legacy software engineer was the most expensive line item on the P L. Google famously paid Principal Engineer Zach Lloyd a retention package so lucrative [ ] The post Bottlenecks appeared first on Keith Brown .
We were halfway to San Antonio yesterday when I realized I had not looked at a single Yelp review or scrolled through a TripAdvisor list. Usually, planning a spring break trip out of Dallas is a week of open tabs and second-guessing. This time, I let Gemini handle the architecture. It chose a specific cabin [ ] The post Bronze Medals appeared first on Keith Brown .
I have managed hundreds of people over my career. The companies I ve worked for have had nearly 100,000 employees combined. I know corporate, I know startups, mostly, I just know people. I know the weight of that responsibility. I know the late nights spent worrying about career paths, interpersonal friction, and the general health of [ ] The post The End of Management appeared first on Keith…
It is a survival mechanism. If you grew up in an environment where silence meant a storm was coming. Maybe it was one parent, a family member, a sibling, or all of the above. As a defensive mechanism, you became elite at reading rooms. You learned to detect a shift in mood before a word [ ] The post Chasing Approval appeared first on Keith Brown .
Most leaders are still stuck in a linear mindset. We have been taught for decades that to double our output, we must double our headcount. It is a simple, comfortable equation that is now completely broken. In the age of AI, thinking of hiring as a 1:1 ratio of people to production is a structural [ ] The post Hire Multipliers Not Headcount appeared first on Keith Brown .
Most leaders confuse activity with progress. We spend our days firefighting and wonder why the fires keep starting. It is easy to feel productive when your calendar is full, but being busy is often a trap that keeps you from being effective. In the movie Jumanji, there is a famous scene where an invasive vine [ ] The post Structural vs. Superficial appeared first on Keith Brown .
I have spent fifteen years in the trenches of high growth SaaS. I have seen the 2 a.m. board deck revisions and the desperate hunt for data gravity. I know what it feels like to earn every dollar of true ARR, recurring revenue through blood, sweat, and manual onboarding. The type of revenue that you [ ] The post The Rise of HARR (Hollow ARR) appeared first on Keith Brown .
It is good to be back sharing my thoughts more. I have mostly stayed off social media since the world got loud a few years ago. It felt like there was enough noise and nobody needed one more opinion. But I have heard from many of you that my perspective still carries weight. That means [ ] The post Reflections on 2025 appeared first on Keith Brown .
Private equity likes to call itself the rational antidote to sentimental founders, bloated corporate structures, and quarterly-obsessed public markets. The narrative is tidy: disciplined investors step in, unlock efficiency, and deliver superior returns through operational excellence. But inside the model is a more unvarnished reality, a world where companies become spreadsheets, people become…
I ve thought a lot lately about my past time in startups earlier in my career. Looking back on it, I had no idea what I was getting into. And today I still see people each day taking the plunge and going off on their on. Joining an early-stage startup is like getting on a fast-paced [ ] The post Early Stage Startup DNA appeared first on Keith Brown .
I was once in a meeting a Superpages.com early on in my career. An executive told his senior team, “We’re all in this together. So, I need your best ideas to double revenue, and I need those ideas by the end of the week.” The room nodded. Later, one of those managers admitted he felt [ ] The post Power Dynamics appeared first on Keith Brown .
The best teams are now elite hires and a fleet of AI agents. Here’s what that means for hiring, org structure, and the future of work. The post The End of Entry Level appeared first on Keith Brown .
I’ve been in SaaS for over two decades. I’ve seen it all—from duct-taped onboarding flows that accidentally convert, to UI tweaks that unlock $10M ARR bumps. But this? What HubSpot is doing right now is one of the biggest unspoken sins in SaaS: decoupling the user experience from the value layer. They’re inviting customers to [ ] The post Headless CRMs appeared first on Keith Brown .
I’ve had some intense conversations lately—friends who run VC firms, founders building on the frontier of AI, and business owners seeing the shift in real-time. And whether we’re talking markets, technology, or workforce strategy, the same theme keeps surfacing. The next three years will be defined by two unavoidable outcomes: 1. The Rise of Abundance [ ] The post Abundance and Displacement…
In the swiftly evolving landscape of artificial intelligence (AI), we find ourselves living in what I call The Mirage Age. This era is marked by a fascinating paradox: the entities we interact with – our jobs, companies, and even our cultural norms – are simultaneously real and illusory. They exist, yet not in the forms [ ] The post The Mirage Age appeared first on Keith Brown .
In 2008, the world witnessed a financial crisis of unprecedented scale, largely precipitated by the collapse of the housing market. A significant contributor to this collapse was the widespread practice of offering home loans with no down payment, leading to a glut of homes that no one wanted to buy. In 2015, a similar trend [ ] The post Toxic Assets appeared first on Keith Brown .
I was having lunch with a friend last week who leads HR at a Fortune 500 company. They just finished a large round of layoffs and are preparing for more. After years of taking free tax credits to keep people at work, quite the opposite is happening now. It s almost like after being stuck at [ ] The post The Great Reset appeared first on Keith Brown .
The Covid pandemic forced the majority of the global workforce to abandon their traditional office space. It challenged them to create a new and very different home work environment. At times this was vastly more productive, and other times it was much less productive. Today I want to explore one area I think we will [ ] The post Healthy in a Hybrid World appeared first on Keith Brown .
The last few years has been one of the most challenging events of our time. And while some of have pushed forward, many are still afraid and stuck in a type of holding pattern of sorts. For those of us in the business of leading, the stakes are high when it comes to how we [ ] The post Leading in Difficult Times appeared first on Keith Brown .
We are in the midst of the one of the most fascinating shifts in modern labor. Businesses are desperately trying to get teams back to the office, while many people are considering whether they even want to work at all. The culprit is not remote work, millennials, or corporate real estate. Those are a red [ ] The post The Illusion of Output appeared first on Keith Brown .
My goal is to be the CEO one day. I have heard this line a thousand times when I ask people what their end game is. The problem is it s very different from what CEOs say when you ask them how they got there. You always hear some variation of this quote from great leaders. [ ] The post Not Everyone Can Be a CEO appeared first on Keith Brown .
100 days on the job. Most new employees are barely out of formalized onboarding in 90 days, let alone quitting their job. But a CEO s role is different. They are brought in to champion a vision and then bring it to life. Kevin Mayer was brought in from Disney+ to TikTok to do much the [ ] The post Kevin Maye appeared first on Keith Brown .
After 10 years of the hustle and grind, you can say I had made it. Fortune 500 companies. Mergers and acquisitions. Running some of the largest consumer websites in the world. Making the top of the Inc. 5,000 list. Everyone talks about getting “there”—to your goal, the top of your own personal, proverbial ladder. But [ ] The post Why I Quit LinkedIn appeared first on Keith Brown .
Stewart, I’ve been your #1 fan since day one. An investor since your IPO. A power user since we adopted it Aha! and used it to become one of the fastest growing remote companies in the world (before remote was cool). Over the last year I had accumulated a decent position in Slack for a personal investor. Sure, you probably [ ] The post Slack is Afraid of Microsoft appeared first on Keith Brown .
The year 2020 will forever be remembered as a year of change in business. Both the medical and social levels demand a necessary shift in the way we function as businesses. The lines between work and home have vanished for everyone. Under quarantine, we went from a separate home and work life to everything happening [ ] The post Vulnerable Conversations at Work appeared first on Keith Brown .
There was a time when law school was my future. It was all I thought about day and night. From researching the top legal fields, to understanding how tiers of law school impacted my future earning capability, I had it all down. There was one problem, a degree plan. There is no undergraduate degree plan [ ] The post Law School and Learning appeared first on Keith Brown .
9 years. It s a long time in the real world. And an eternity in the tech world. That is how long of a head start Tesla has had on big auto makers like GM, Ford, and Chrysler. That is why I couldn t help but smile a bit when CNBC wrote about the Tesla competitor the [ ] The post Big Auto vs. Tesla appeared first on Keith Brown .
Slack released their S-1 today, and as usual with SaaS companies I took time to read through it. I do not usually do write ups on S-1 s, in fact, this is my first one. As I read through it there were some interesting learnings worth calling out, especially around their strategy. Here are a few [ ] The post Slack s S-1 Filing appeared first on Keith Brown .
I live in the future. Much like Marty McFly in Back to the Future, I feel like I ve already lived it in some way. No, I do not own a time machine. It has more to do with the way I am. You see, one of my strengths is vision. I can just as easily [ ] The post Why Entrepreneurs Struggle with Empathy appeared first on Keith Brown .
Just an interesting note from my project Facebook fan page this morning. I crossed the 30,000 fan barrier and wanted to see how much Facebook would now let me spend on a sponsored post. So, I asked the question to myself plain and simple. Are Facebook Ads better than Google Ads at reaching people effectively? [ ] The post Thoughts on Facebook vs. Google for Growth appeared first on Keith Brown .
What is the Zero Moment of Truth? Google defines it as the following. The ZMOT, or Zero Moment of Truth, is a new decision-making moment that takes place a hundred million times a day on mobile phones, laptops and wire devices of all kinds. It’s a moment where marketing happens, where information happens, and where [ ] The post 25 Google ZMOT Quotes — The Zero Moment of Truth appeared first on…
Often I hear website owners paranoid about what people post on their site. Of course nobody wants spam, but why are you so worried about what people say on your website? Think you are going to get sued for hosting defamation? Think again. The CDA, or Communications Decency Act, specifically section 230, protects websites from [ ] The post I Love Section 230 of the Communications Decency Act…
There are tons of absolutely broke dreamers out there, and hopefully I’ve moved in the right direction over the years. I have definitely learned a few things along the way, and I’d like to share a few in hopes of saving at least one person from wasting at least one hour of their life. Ideas, [ ] The post How Not to Be Another Broke Entrepreneur appeared first on Keith Brown .
I used to advertise on facebook quite regularly. I could monitor the return on every dollar invested, and it was a great time to invest in buying fans. But lately a few things have changed and I stopped most of my facebook advertising. Why? The reason is pretty simple. I wasn’t getting the same ROI, [ ] The post Social Media Risks for Your Business and Your Life appeared first on Keith Brown .
Some would call SMS marketing the most effective marketing channel ever invented. They wouldn’t be wrong either. With a bone-crushing 98% open rate, if text messaging were an Olympic athlete, it would win all the medals in every sport, even figure skating. Running a text messaging campaign isn’t rocket science. It’s actually the complete opposite [ ] The post Insane Mobile Phone SMS Stats that…
I remember going to work with my dad growing up. From the first time I saw his degree hanging on his office wall I began adding things up in my mind, and more importantly in my spirit. I don’t think I realized how much weight I was putting on that piece of paper all those [ ] The post An Open Letter to This Years Graduating Class appeared first on Keith Brown .
Experian Hitwise released a recent study touting that 1 Facebook fan = 20 extra visits to your website. They studied top retailers, and came away with the conclusion that since big companies are winning online, anybody can just as easily. I couldn’t disagree more with their blanket statements about Social Media, and thought they hid [ ] The post The ROI of Advertising on Facebook appeared first on…
Today I was able to attend the Hoth‘s webinar about SEO link building. It was lead by Alex Pyatetsky, and discussed a wide range of topics surrounding link building. There were a few mentions of the Hoth and their product, but for the most part Alex stayed on topic. I’m not going to discuss everything [ ] The post 6 Ways the Hoth Builds Valuable Links to Your Brand appeared first on Keith Brown .
If there was an SEO anonymous support group I’d introduce myself like this. My name is Keith, and I have a problem. Anything that can be reverse engineered and optimized, I attempt to manipulate for fun, personal growth, or financial gain. So naturally when LinkedIn introduced endorsements, I was all about it. The end game: [ ] The post Optimize Your LinkedIn Profile Using These Simple Marketing…
I’m fascinated with algorithms and equations. Part of me thinks that I don’t actually love optimizing for Google, as much as Google is the most profitable problem solving puzzle the modern world has ever seen. What does this have to do with balancing the equation of acid and alkaline foods and a healthy diet? Read [ ] The post Balancing Acid vs. Alkaline Foods in Your Diet appeared first on Keith…
Politicians aren’t solving the debt crisis, so entrepreneurs around the world are. Bitcoin, a decentralized digital currency, was created in 2009 based on an open-source p2p internet protocol. Think of it as the Napster of the international economy. In late 2011 a bitcoin was worth $2, last week it was $180, at times reaches as high [ ] The post Bitcoin and the Psychology of Distrust in our…
The following is my rough outline from the 11AM SXSWi session featuring Pinterest Co-Founder and CEO Ben Silbermann. There was lots of great advice on monetization, design, building a successful business, and social communities. And I felt like sharing a few of those things with you today. The questions covered everything from his job history, [ ] The post Pinterest CEO Ben Silbermann on Launching…