(I realize I’ve been relatively quiet since I started my new job in January…this is what I’ve been up to. It may be the most interesting job I’ve ever had…but more to come on that over time.)

I was at a recent Gartner CEO conference on AI in New York City, and one phrase keeps rattling around in my brain: “There is such a rapid pace of development that we are regularly seeing ‘obsolescence before maturity.'” In other words, by the time AI products reach early adoption in the market, they’re already obsolete.

But here’s the thing – while everyone’s racing to build the next AI breakthrough, they’re missing a massive problem hiding in plain sight. AI has fundamentally changed the content game. You can generate content faster than ever, but the risk has grown exponentially. Human review doesn’t scale at AI speeds. Companies need intelligent guardrails.

That’s why I’m excited to announce what we’ve been building at Markup AI.

The Problem No One’s Talking About

Let’s be honest about what AI does well and what it doesn’t. AI models are fantastic at content generation by the pound, but they’re not great at precision and quality. More importantly, AI can’t possibly check its own work for quality. As you know from using ChatGPT or Claude, when you push back on AI output, it responds “you’re absolutely right,” no matter what you say. That’s not exactly the kind of rigorous quality control you want for your enterprise content.

The writing assistant industry has been playing “small ball” for years – spell check, grammar, basic tone suggestions, looking at one sentence at a time as you’re writing content. They’ve ignored several elephants in the room: brand compliance, terminology management, risk management, and batch checking already-published content.

Enterprise content production and compliance is a massively fragmented problem. Companies have thousands of people who write publicly facing content and dozens of systems for authoring, storing, and publishing content on one hand; and multiple brand and policy rule books and thousands to hundreds of thousands of pieces of already-published content on the other.

We work with the world’s largest enterprises across technology, healthcare, financial services, and manufacturing – organizations that can’t afford content mistakes because the stakes are too high. One wrong sentence could mean litigation, regulatory issues, or a reputation crisis.

Markup AI: Your AI Watching Your AI

This is why we’re launching Markup AI – the first content guardian agent. Think of it as your AI watching your AI. We scan, score, and rewrite content to ensure it’s on-brand, compliant, and won’t create problems.

Fixing typos is great, but that won’t ensure your content doesn’t get you sued, fired, or create a reputation crisis. We’re making sure your content actually serves its purpose.

The name says it all: Editors markup documents. Lawyers markup documents. Writers markup their own documents. And developers regularly use markup languages and annotations. Markup AI will quickly become the standard for Content Guardian Agents in the AI space – helping companies to scan, score, and rewrite content that is consistent, authentic, and compliant, rapidly and at scale.

The Press Release announcing our launch and $27mm financing is here.

What Makes Us Different

Here’s what makes us different: we meet you where you already work. Through our API-first approach, Markup AI integrates into whatever content systems and workflows you’re using today. No rip-and-replace required.

We’re building the future of content creation – where speed doesn’t compromise safety. True AI-native solutions that tackle trust and risk head-on in an AI-first world with triggers for human-in-the-loop. Because at the end of the day, AI can write, but someone needs to ensure what it writes is actually right.

This is a Restart

This isn’t just a product launch – it’s a restart. A new AI-native platform, a new team, a new location, and a new brand. With years of linguistic engineering experience behind us in our prior business Acrolinx, the gold standard for enterprise content compliance, we’re excited to unveil our new native-AI brand and platform, Markup AI.

We’ve been at this for a while now, and we’re proud to announce that leading tech companies such as Amazon, Adobe, ServiceNow, Gainsight, Instacart, Coinbase, plus over 75 more AI-first companies have all asked for early access to our Content Guardian Agent and a number are already up and running.

The future of content is here – and it needs intelligent guardrails. We’re excited to show you what we’ve built and how Markup AI can help your organization navigate the AI content revolution safely and successfully.

Ready to see your AI watching your AI? Visit us at www.markup.ai to learn more, get an API key for free, and try out our Writer’s Playground or the API itself.

More to come on the restart journey. It’s an interesting one, full of lessons for Startup CEOs everywhere.

Years ago, I heard then General David Petraeus give a talk to a small group of us about leadership. He was literally coming to us live from his command center in Iraq or Afghanistan when he was running the whole theater of war over there. I realize he subsequently had some tarnish on his reputation after pleading guilty to a misdemeanor around handling classified information, but the main thrust of his talk, his Formula for Strategic Leadership, still stands as one of the more memorable talks on leadership I’ve ever heard and is no less relevant as a result.

Given that I still remember it vividly 14-15 years later, I thought I’d recreate it here with my own annotations after the four principles. It’s a simple 4-step formula:

1. Get the big ideas right. Obviously, you aren’t going to go down in history as a great leader if you consistently get the big picture wrong. That doesn’t mean you have to be right about everything and every detail. But if you pick the wrong market, bet on the wrong approach, happen to get your timing wrong by a few years…it’s hard to win.
2. Communicate them up and down the organization. Every mature leader knows that ideas and plans only go so far if they stay in your head or get filtered down through leadership teams. For your values to take root, for your strategy and strategic choices to make sense, and for people in the organization to be able to connect their daily execution to your company’s north star, you need to spend a lot of time communicating those things throughout the organization. Different groups, different meetings, different channels. And then, when you’re finally exhausted and sick of hearing yourself say those things over and over and over again…keep saying them.
3. Personally oversee their implementation. Leaders who throw things over the proverbial wall — “here’s what to do, now go do it while I move on to something else” — are not really strategic leaders. The devil is in the details. If you can’t bother to spend a few minutes overseeing the implementation of your strategy and carefully watching when and how it works and doesn’t (see next item), you may be a good visionary, but you’re not really a strategic leader.
4. Memorialize and institutionalize best and worst practices. This is where so many leaders fall down on the job. When something in your organization wraps up — a launch, a quarter, a project — you have to do a retrospective, curate learnings both good and bad, and publish them. That way your whole organization can have a growth mindset as a system.

There are about a zillion books on leadership out there. Most of them are probably between 200 and 400 pages long. While they may all have variations on this theme and colorful examples behind them, this still rings true for me as the essential formula for strategic leadership.

My cofounder Cathy wrote a great post on the Bolster blog back in January called Procrastinating Executive Development, in which she talks about the fact that even executives who appreciate the value of professional development usually don’t get to it because they’re too busy or don’t realize how important it is. I see this every day with CEOs and founders. Cathy had a well phrased but somewhat gentle ask at the end of her post:

My ask for all CEOs is this: give each of your executives the gift of feedback now, and hold each other accountable for continued growth and development to match the growth and development of your company.

Let me put it in starker terms:

Grow or Die.

Every executive, every professional, can scale further than they think is possible, and further than you think is possible. Most of us do have some ceiling somewhere…but it will take us years to find it (if we ever find it). The key to scaling is a growth mentality. You have to not just value development, you have to crave it, view it as essential, and prioritize it.

Startups are incredibly dynamic. You’re creating something out of nothing. Disrupting an industry. Revolutionizing something. Putting a dent in the universe. For a startup to succeed, it has to constantly put something in market, learn, calibrate, accelerate, maybe pivot, and most of all grow. How can a leader of a startup scale from one stage of life to the next without focusing on personal growth and development if the job changes from one quarter to the next?

I was lucky enough to have a great leadership team at my prior company, Return Path, over the course of 20 years. Within that long block of time with many executives, there was a particular period of time, roughly 2004-2012, that I jokingly refer to as the “golden age.” That’s when we grew the business from roughly $5mm in revenue to $50 or $60mm. The remarkable thing was that we executed that growth with the same group of 5-6 senior executives. A couple new people joined the team, and we struggled to get one executive role right, but by and large one core group took us from small to mid-sized. Why? We looked at each other — literally, in one meeting where we were talking about professional development — and said, “we have to commit to individual coaching, to team coaching, and to growth as leaders, or the company will outpace us and we’ll be roadkill.”

That set us on a path to focus on our own growth and development as leaders. We were constantly reading and sharing relevant articles, blog posts, and books. We engaged in a lot of coaching and development instruments like MBTI, TKI, and DISC. We learned the value of retrospectives, transparent 360s, and a steady diet of feedback. We challenged ourselves to do better. We worked at it. As one of the members of the Golden Age said of our work, “we went to the gym.”

The “Grow or Die” mantra is real. You can’t possibly be successful in today’s world if you’re not learning, if you don’t have a growth mentality. You are never the smartest person in the room. The minute you are convinced that you are…you’re screwed.

If you don’t believe me, look at the development of your business itself as a metaphor for your own development as a leader. What happens to your startup if it stops growing?

(You can find this post on the Bolster Blog here)

At What Price False Positives?

As has been covered in many places, including Direct and The Wall Street Journal, Verizon settled a lawsuit yesterday over “too aggressive” spam filtering, or what we in the business call false positives — filtering out legitimate, non-spam emails as spam.  This is a huge problem that part of our business at Return Path, our Delivery Assurance Solutions group, has been fighting for years.

The gist of the settlement is that Verizon is changing the way it filters spam to make sure more legitimate mail gets through, and that it is refunding various small amounts of money or free months of service to customers who complained about the problem.

I am NOT a believer in lawsuits like this at all.  Also, I think the act of filtering aggressively enough to catch the spam but not so aggressively as to cause false positives is a very difficult balancing act that most ISPs actively struggle with every day.

So the outcome here is that a bunch of consumers will receive money or refunds or free service ranging from a few dollars up to potentially $100.  The seven class plaintiffs are going to receive $1000 each for their troubles.  Oh and for good measure, the lawyers are asking for $1.4 million in expenses.  Don’t even get me started on that one.

All that said, though, it’s interesting that there’s now some kind of economic cost to false positives on the books.

I am fortunate in my current job to spend a lot of time talking to other founders and CEOs. I mentor and coach them, my company and I help counsel them on executive and board searches, and I spend time with them at conferences and seminars. Even when I am giving them advice, I always take time to learn what they’re doing, what works, and what doesn’t work. I’ve noticed a consistent set of behaviors and practices common among the successful founder operators – the ones who go on to lead their companies through multiple chapters of growth and sometimes never hire the “seasoned operator” to come in and take over. 

#1 – They are students of the game. It’s easy to get mired in the day to day details of building a business from scratch. The best founders are the ones who take time to watch, read, and learn. They want to see what other entrepreneurs do and they ask probing questions about what works and doesn’t work. They read blog posts, articles, and books. They listen to podcasts and constantly try to apply learnings to their company. They seek out coaches and mentors. 

#2 – They have positive and regular (and sometimes extreme) personal habits. It’s easy to get sucked into working all the time when you’re building a business from scratch and counting every penny and every minute. However, observing how successful CEOs manage their time shows that either very early mornings or very late nights are pretty common, and not in the way you might think. A 4:30 or 5 am alarm for regular exercise, or drawing a hard line around “no work after 6” means the leader is committed to personal time to stay fresh, and connect with friends and family. Abraham Lincoln is quoted as having said “Give me 6 hours to chop down a tree, and I will spend the first four sharpening the axe.”

#3 – They know how to leverage themselves. It’s easy as a founder to think you’re the only person who can get something done. Delegation is hard, and it often involves investing more time to train someone else how to do something than doing it yourself. The best founders figure out how to squeeze every minute out of the day by remembering that building a startup is a team sport and that building up the team around them is the key to their own productivity. 

#4 – They have great work hygiene. It’s easy to not respond to emails or texts or Slack messages because they’re not the most important thing you have going on. It’s easy to not send a Thank You note after a meeting or take time to connect with a colleague on a human level. The best founders are the ones who know the power of their own words, the power of their own presence, and who find the time to inject that power into others’ lives.

#5 – They have a recurring belief in creative destruction. It’s easy to create a new company because there’s a need in the market to disrupt incumbents. Creative destruction is central to the story of entrepreneurs everywhere. It’s very hard to apply that same creative destruction mentality to your own work. The best founder operators are the ones who are not just capable of tearing down an industry…but are equally capable and enthusiastic about tearing down their own product, their own team, and their own business processes in order to build them back up. MVPs are often too “M” and need to be replaced and upgraded consistently over time.

None of these practices is the path of least resistance—they require extra effort. I’m not sure what the cause and effect is here. A weak founder with bad product market fit and an untrusting attitude towards employees can’t just start waking up early and reading a lot and magically become successful. But on the margin, enough correlation leads me to believe that there’s something in the combination of these practices that leads to the competitive edge, the informed intuition, the vision, and the ability to motivate the people around them that are common in successful founder operators. 

(The following post was written by one of Return Path’s long-time senior managers, Chris Borgia, who runs one of our data science teams and has run other support organizations in the past, both at Return Path and at AOL.  I don’t usually run guest posts, but I loved the topic with Chris suggested it, and it’s a topic that I’d only have a limited perspective on!)

Managing Up in a Growing, Global Workplace

For many years, I thought “managing up” was a cheap way of getting ahead. I thought someone who managed up was skilled at deceiving their boss into thinking they were more accomplished than they really were.

I have since learned that managing up, or managing your boss, is not devious, but is actually a valuable discipline. When you learn to manage up successfully, you empower your boss to better represent your interests to influencers in the organization.

If you are a manager, you should realize that in addition to managing your boss, you can help your employees effectively manage you. When our employees help us to be successful, we are further enabled to invest in their success. This symbiosis is seen in any relationship – the more you help the other person, the more they will be able to – and want to – help you. If you are a manager, it’s important to realize that your employees should be managing up, and you can encourage them to do so by being vulnerable, admitting ignorance, and asking for support.

There are many books and articles on managing up or managing one’s boss. The essentials are fairly consistent:

• Understand your boss’s goals, priorities, and needs
• Know your boss’s strengths and weaknesses
• Set mutual expectations to build trust
• Communicate and keep your boss informed

You’ll need to be intentional about the essentials no matter where you work, but there are additional challenges of managing up in a growing, global workplace like Return Path. In a growing company, you’re likely to work for a boss who is new to their role, the company or the industry. In a global company, you may report to a boss who works in another office, or even in another country. The fundamental aspects of managing up are the same, but these situations can require a tailored approach.

When your boss is new to their role, the company, or the industry

In a growing company, you’re likely to report to someone who is new to their role in the company, new to the company itself, or even new to the industry. You can be invaluable to your boss in closing the knowledge gap and enabling them to make the best decisions for you and your team.

• Process Help your boss understand how the department operates. How are goals and priorities determined? How do people communicate? What does the team expect from the boss?
• People If your boss doesn’t know the people, they may lack the appropriate empathy in a given situation. Help them understand your team’s needs and how their decisions impact the people.
• Decision Making Your boss will likely need additional data to help them make decisions. Providing your boss with this data up front, saving them from admitting ignorance, will go a long way to developing a strong relationship.
• Context Sometimes your boss won’t know what they don’t know, so providing your boss the context around issues, decisions, and goals will enable them to make the best decisions for your team.

When your boss works in another office or country

In a global workplace, it’s likely that at some point you will have a boss who works in another office or even in another country. Having a remote boss offers many opportunities for managing up.

• Visibility Your boss doesn’t see you – or possibly others on the team – every day, so you might want to communicate more about the day-to-day operations of the team. At times, it will feel like you are sharing minutia, but it’s likely your boss will find this valuable in developing a complete understanding of what is going on.
• Insight If you work in a core office, you have a tremendous opportunity to be your boss’s eyes and ears.  What are you seeing or hearing locally that might change your boss’s plans or perspective? What are people worried about? Are there any rumors your boss should be aware of?
• Culture If your boss is in a different country, you will need to develop a relationship that considers any cultural differences. Cultural differences are seen in office attire, working hours, email habits, vacation schedules, and more. Bosses in some cultures may expect more deference, while in others they may expect more direct honesty. Understanding your boss’s culture, and helping her understand yours, will develop mutual respect and expectations to make each other successful.

Your relationship with your boss is a symbiotic one. Your boss can’t be successful unless you are, so they are your champion.  Learning to effectively manage up, especially in a growing, global workplace, is not nefarious business. Your boss will represent and support you to the best of their abilities. The more you enable your boss, the better they can support you, and everybody wins.

Yiddish for Business

Contrary to popular belief, Yiddish isn’t “Jewish slang” (I hear that a lot).  According to Wikipedia, Yiddish is a basically a High Germanic language with Hebrew influence of Ashkenazi Jewish origin, spoken throughout the world. It developed as a fusion of German dialects with Hebrew, Aramaic, Slavic languages and traces of Romance languages.  It is written in the Hebrew alphabet.

I don’t speak Yiddish.  Like many American Jews whose families came to America in the late 19^th and early 20^th centuries, my grandparents spoke it somewhat, or at least had a ton of phrases they wove into everyday speech.  Presumably their parents spoke it fluently before coming here and Americanizing their families.  My own parents have a handful of stock phrases down.  My brother and I have even less.

What I like best about Yiddish is that I find it to be a very descriptive and also onomatopoetic language.  I can never verbally describe a Yiddish word without a lengthy description and some examples, and usually some level of gesticulation.  I’ll try to be more succinct below.  But in the end, words mean a lot like what they sound like they should mean.  A lot of New Yorkers who aren’t Jewish end up knowing a handful of Yiddish words because they’re pretty prevalent in the City, but many people outside New York don’t.  So I thought I’d have a little fun here and do something different on the 6^th anniversary of launching this blog (today) and list out some of my favorite Yiddish words and describe them with a business context.  In no particular order…

–          Schmooze – to chat someone up, work them, frequently with some kind of hidden agenda in mind.  Business application:  “She showed up at the charity event just to schmooze Alice, who was a potential client.”

–          Chutzpah – nerve, as in “wow, he has some nerve.”  My dad always said the classic description of chutzpah was the kid who murdered both of his parents, then pleaded with the judge for leniency because he’s an orphan.  Business application:  “He missed all his goals this quarter and asked for his full bonus and a raise?  Now that takes real chutzpah!”

–          Spiel (pronounced schpeel) – a monologue or lengthy pitch.  Business application:  “I’m raising money, so I have to really organize my spiel before I go talk to the VCs.”

–          Schtick – someone’s standard song-and-dance.  Business application:  “I stood up in front of the room and gave my usual schtick about our values and mission.”  Kind of like Spiel.

–          Schlep – to make a long, pain-in-the-ass kind of trip.  Business application:  “I had to schlep all the way to Toledo for a meeting with that guy, and he didn’t even end up signing the deal.”

–          Mazel tov – literally means “good luck” but usually used in regular conversation to mean “congratulations.”  Business application:  “You got a promotion?  Mazel tov!”

–          Noodge – someone who inserts himself into a conversation in a somewhat unwelcome manner.  Related to Kibbitz – to give unsolicited advice from the sidelines. Business application:  “Sally is such a noodge.  She kibbitzes about my unit’s strategy all the time and just stirs up trouble.”

–          Maven – an expert, even a self-styled one, in a very niche area.  Business application:  “You want to figure out what smartphone to  buy?  Ask Fred – he’s the maven.”

–          Kosher (a Hebrew word as well) – completely by the books, originally referring to dietary laws that religious Jews follow.  Business application:  “Ask Marketing if it’s kosher to use our partner’s logo like that.”

–          Verklempt – choked up, overcome.  Business application:  “When I got my review and promotion and raise, I was so verklempt that I couldn’t speak for a minute or two.”

–          Schlock, Dreck, Chazerai, Bupkis – all have slightly different literal meanings (apparently Bupkis means “goat droppings”), but I use all of them somewhat interchangeably to mean junk or something of limited or no value.  Business application:  “That presentation was nothing but chazerai.  What did I get out of it?  Bupkis.”

–          Kvell – to beam or burst with pride, related to Nachus – warm “gooey” feeling of pride.  Business application:  “I had so much nachus when my company won that award for being the best place to work, I was just kvelling.”

–          Mishegas or Bubbamyseh – craziness or self-imposed silliness.  You might have heard the word Meshugenah before, which means crazy.  Business application:  “I can’t get all caught up in his mishegas.  I’m going to make my own decision here.”

–          Kvetch – either a noun or verb meaning complain, in a harpy kind of way.  Business application:  “Frank is such a kvetch.  He is just never happy.”

–          Mensch – a good guy.  Business application:  “Michael is such a mensch.  He always helps his colleagues out even when he doesn’t have to or doesn’t get credit for it.”

–          Fercockt (pronounced Fuh-cocktah) – crazy, messy.  Business application:  “John’s project plan is totally fercockt.  No one can follow it even when he tries to explain it.”

–          Mishpochah – family.  Business application:  “Welcome to the company – we’re happy to have you in the mishpochah.”

–          Tsuris – heartache or sadness.  Business application:  “Boy that’s one client that gives me nothing but tsuris.”

–          Tchotchke (pronounced chach-kee) – a trinket or little toy.  Business application:  “What kinds of tchotchkes are we giving away at our booth at the upcoming trade show?”

Pull one of these out in your next meeting – see what it gets you!

Part of creating the best place to work  is learning how to self manage – very, very well.  This is an essential part of Creating an environment of trust , but only one part.  What does self-management mean?  First, and most important, it means realizing that you are in a fishbowl.  You are always on display.  You are a role model in everything you do, from how you dress, to how you talk on the phone, to the way you treat others, to when you show up to work. 

But what are some specifics to think about while you swim around in your tank?

1. Don’t send mixed signals to the team.  You can’t tell people to do one thing, then do something different yourself
2. Remember the French Fry Theory of being a CEO.  My friend Seth has the French Fry theory of life, which is simply that you can always eat one more French fry.  You’re never too full for one more fry.  You might not order another plate of them, but one more?  No problem.  Ever.  As a CEO, you can always do one more thing.  Send one more email.  Read one more document.  Sometimes you just need to draw the line and go home and stop working!  (See my earlier post  here  on how Marketing is like French Fries for another example.)
3. Regularly solicit feedback, then internalize it and act on it.  Do reviews for the company.  Do anonymous 360s (I’ve written about these regularly here). Get people a review that has ratings and comments from their boss, their peers, and their staff.  Do them once a year at a minimum.  And do one for yourself.  They’re phenomenal.  Everyone needs to improve, always.  Our head of sales Anita always says “Feedback is a gift, whether you want it or not.”  Make sure you do them for yourself as well.  Include your Board.  If you don’t agree with the feedback you are being given that is likely a data point that you have a BLIND SPOT.  Being defensive about feedback is dangerous.  If you don’t get it/don’t like then do some more work to better understand it.  Otherwise you will forever be defensive and never develop in this area
4. Maintain your sense of humor.  It’s not only the best medicine, it’s the best way to stay sane and have fun.  Who doesn’t want to have fun at work?
5. Keep yourself fresh:  Join a CEO peer group.  Work with an executive coach.  Read business literature (blogs, books, magazines) like mad and apply your learnings.  Exercise regularly.  Don’t neglect your family or your hobbies.  Keep the bulk of your weekends, and at least one two-week vacation each year, sacrosanct and unplugged.  As Covey would say, Sharpen the Saw

You set the tone at your company.  You can’t let people see you sweat too much – especially as you get bigger.  You can’t come out of your office after bad news and say “we’re dead!”  You can make a huge difference by being a great role model, swimming around in your fishbowl.

The Best Laid Plans, Part I

One of my readers asked me if I have a formula that I use to develop strategic plans.  While every year and every situation is different, I do have a general outline that I’ve followed that has been pretty successful over the years at Return Path.  There are three phases — input, analysis, and output.  I’ll break this up into three postings over the next three weeks.

The Input Phase goes something like this:

Conduct stakeholder interviews with a few top clients, resellers, suppliers; Board of directors; and junior staff roundtables.  Formal interviews set up in advance, with questions given ahead.  Goal for customers: find out their view of the business today, how we’re serving them, what they’d like to see us do differently, what other products we could provide them.  Goal for Board/staff: get their general take on the business and the market, current and future.

Conduct non-stakeholder interviews with a few industry experts who know the company at least a little bit.  Goal: learn what they think about how we were doing today…and what they would do if they were CEO to grow the business in the future.

Re-skim a handful of classic business books and articles.  Perennial favorite include Good to Great, Contrarian Thinking, and Crossing the Chasm.

Hold a solo visioning exercise.  Take a day off, wander around Central Park.  No phone, no email.  Nothing but thinking about business, your career, where you want everything to head from a high level.

Hold senior staff brainstorming.  Two-day off-site strategy session with senior team and maybe Board.

Next up:  the Analysis Phase.

The Beginnings of a Roadmap to Fix America’s Badly Broken Political System?

UPDATE:  This week’s Economist (March 17) has a great special report on the future of the state that you can download here, entitled”Taming Leviathan:  The state almost everywhere is big, inefficient and broke. It needn’t be,” which has many rich examples, from California to China, and espouses a bunch of these ideas.

I usually try to keep politics away from this blog, but sometimes I can’t help myself.  I’m so disgusted with the dysfunction in Washington (and Albany…and Sacramento…and…) these days, that I’ve spent more spare cycles than usual thinking about the symptoms, their root causes, and potential solutions.  A typical entrepreneur’s approach, I guess.  So here’s my initial cut at a few solutions.

I’m sure it’s incomplete, and it’s possibly overly simplistic.  While I think it’s a pretty pragmatic and non-partisan approach, I’m guessing people will have visceral political opinions about it.  Here are five things I’d like to see that I think will start us on the road to repair:

• Nonpartisan redistricting: All districts at all levels of government should be drawn by nonpartisan commissions.  There is no reason to create “safe” seats and uncompetitive elections that drive candidates to extreme positions in order to win primaries.  All of that is undemocratic.  I hope California’s proposition that creates this kind of solution works and is copied.
• Public finance of campaigns: This will have to come with a constitutional amendment limiting free speech when it comes to political campaigns, but we should be prepared as a society to limit freedom in that one narrow way in order to remove money from politics.  This topic just keeps coming up, from both the left and the right (think about the examples of Wall Street donations impacting financial reform on one side and public sector union political contributions impacting negotiations with states and cities on the other).
• Presidential line-item veto: Its constitutionality may be in question, but this would give the President a more granular form of one check-and-balance he already has and could greatly help reduce wasteful spending as well as simplify legislation (more on that in a minute).
• Auto-expiration of tax/spend bills: I found the debate over the expiration or extension of the “Bush tax cuts” to be enlightening.  Maybe some class of tax/spend bills — those over a certain dollar figure, those that create entitlements, though that involve government subsidies to industry — should be forced to be renewed every 5 or 10 years instead of being “evergreen” so that the debate can reoccur in light of changes in circumstance.  How many other things are “on the books” in ways that don’t make sense in today’s world?
• Simplicity of legislation: The health care reform bill was 1,990 pages long according to the pdf I just downloaded, and few if any in Congress actually read the whole thing.  They even admitted it AT THE TIME.  Is this a smart way to govern?  Whether voluntarily or via constitutional amendment, Congress should consider only passing single-issue bills and maybe even limiting the size of any given piece of legislation to something that at least THEY THEMSELVES ARE ABLE TO READ.

These things should do a lot to ease legislative gridlock, relieve bitter partisan rancor, and remove some of the silly parliamentary manoeuvrings that plague our government today.  Whether or not they can systematically deal with elected officials’ unwillingness to tackle hard problems and penchant for personal deal-making and runaway deficit spending is another question.

My personal belief is that country could stand some form of a new Constitutional Convention to critically review our society and its governance after almost 250 years.  I love our Constitution and think it was wisely laid out as the foundation for what has become one of the world’s greatest and most enduring nations…but that doesn’t mean that the Founders, who lived in a very, very different time, had perfect vision for all eternity.

In May 2023, Fred Wilson wrote a post about being approached by a company that had trained a large language model on all 9,059 of his AVC blog posts. They wanted to offer a chatbot called “Ask Fred.” He said no thanks.

His reasoning was sharp. He’s fine with anyone using his content to train AI. He put a Creative Commons license on his blog from the start. But he didn’t want a bot pretending to be him. The whole point of his blog is the humanity — the daily conversation, the thinking out loud, the relationship with readers. A chatbot that mimics Fred Wilson isn’t Fred Wilson. It’s a parlor trick.

I read that post and agreed with Fred completely. An AI version of me that replaces me? No interest.

But an AI version of me that helps me be more productive while keeping my voice and point of view? That’s a different story entirely.

Building MattBot

MattBot is a custom agent I built inside Chatgipity, our company’s internal AI platform. It’s not a gimmick. It’s one of the most useful tools I’ve ever created.

Here’s what’s under the hood:

• My complete body of writing. Every blog post from 20+ years of StartupCEO.com. My three books — Startup CEO, Startup Boards, and Startup CXO. My eBooks. Podcast transcripts from over 200 episodes. Conference talks.
• My email and Google Drive. So it has context on what I’m working on, who I’m talking to, and what’s current.
• A detailed map of what to include. I didn’t just dump content in. I created a structured guide for the agent — what topics I cover, what my positions are, how I frame arguments, what language I use and don’t use.

The result is an agent that doesn’t replace me. It accelerates me. It knows how I think, how I write, and what I’ve already said about many topics in entrepreneurship and leadership.

How It Saves Me Time

Let me give you some real examples.

A college kid I used to coach in baseball reached out recently and asked to interview me for his freshman entrepreneurship class. I always say yes to these — it’s important to me to help young people who are curious about building things. But historically, that’s a 90-to-120-minute commitment: time to think about the questions, time to write thoughtful responses, time for follow-ups.

This time, I asked him to send me the questions ahead of time. I fed them to MattBot. In 30 seconds, I had draft responses that were substantively right and sounded like me. I spent five minutes editing them, sent them back, and then spent 15 minutes on follow-up questions. Total time: 20 minutes instead of two hours. Same quality. Same voice. Same care.

Preparing for podcast appearances used to take me 30 minutes of reviewing the host’s questions, thinking about framing, jotting notes. Now it takes 30 seconds — MattBot drafts my talking points based on what I’ve already written and said about those topics, and I review and adjust on the fly.

Taking a generic output from any LLM and “Matt-izing” it takes 30 seconds. The upstream work on the LLM might save hours, but the only reason the final product works is that MattBot refines it with my language, my voice, and a high percentage of my long-term body of knowledge.

How the Company Uses It

This is where it gets even more interesting. MattBot isn’t just for me.

Marketing or our PR firm can hand me bullet points for an article or a LinkedIn post, and I can have MattBot do a first draft in 30 seconds. I review it, tweak it, and send it back. What used to be a multi-day back-and-forth is now an instantaneous turnaround.

Better yet, I published the agent to two colleagues in Marketing so they can use it directly. They can draft thought leadership content in my voice without waiting for me to be available. I still review everything — that’s non-negotiable — but the bottleneck is gone.

The Flywheel

Here’s what makes MattBot different from a one-time prompt or a static set of instructions: I treat it like a living system.

Every time I review a response and make edits, I feed those edits back in and tell the agent to learn from them. Any time I write something new — a blog post, an article, an email that captures how I think about a topic — I feed it in. Every new podcast transcript goes in.

So MattBot keeps getting better over time. It’s not a snapshot of who I was when I built it. It’s an evolving representation of how I think and communicate right now.

Fred was right to say no to “Ask Fred.” But I think he’d appreciate what MattBot actually is: not a replacement for humanity, but a tool that gives me more time to be human.