The True Essence of "Founder Mode"

Paul Graham’s recent “Founder Mode” blog post has stirred up a lot of chatter and a lot of opinions in the startup world. Some folks think he’s advocating for micromanagement, while others say he’s oversimplifying things by presenting two extremes. But here’s how I see it: "Founder Mode" is about one thing—doing whatever it takes to win.

For me, being in Founder Mode is all about giving a shit—about everything. This doesn’t mean you shouldn’t hire talented managers (as PG suggests); in fact, you absolutely should. But when you do, your first and most important job is to be the champion of the vision, mission, and purpose of the company. It’s not about micromanaging for the sake of control. It’s about making sure every move, every decision, every action, and every strategy aligns with what the company needs to succeed.

Let’s be real: sometimes micromanaging is necessary. And that’s okay. Startups are hard. It is unlikely you’ll win. Every battle you engage in is David versus Goliath. If things aren’t lining up with the vision or the standards that you know are crucial to winning, you’ve got to step in. But the goal isn’t to hover over everyone’s shoulder. It’s to build a culture where everyone—from the top down—gives a shit.

Hiring the right people is key. Don’t just grab big-company execs because of their impressive, shiny resumes. You want doers—people who are ready to dive deep into the problem you’re solving, people who are champions of your vision, and who are relentless in finding solutions. You need people that give a shit.

Once you’ve got the right team, step back and let them do their thing. Micromanagement shouldn’t be your default mode but don’t hesitate to step in when things aren’t going as they should. As a founder, you have to stay deeply involved in the critical decisions that steer the company and you need to have opinions on everything else your company does. Sometimes you’ve got to make the tough, unpopular calls and hold your team to the highest standards. That’s your job. You are the most qualified to do these things. Others may seek consensus, or take the easy path. Some will put their future ahead of the company’s. That may be reasonable for them, but it’s not for you. To me, Founder Mode means giving a shit and doing what only you as the founder can reasonably do. Take that risk. Do things that don’t scale. Make unpopular decisions. Own failure and success.

If you feel like you have to micromanage every decision, every person, and everything, you aren’t in Founder Mode, you’re just a bad leader. If you can’t trust the people on your team to do what it takes for the company to win, or easily adjust their work based on your guidance, you are probably shitty at hiring, terrible at championing your vision, bad at motivating, and junk at managing. Don’t hide your failures behind “Founder Mode.”

At the end of the day, to me, being in Founder Mode means being stubborn about your principles and vision, caring more than anyone else about what your company is trying to achieve, and doing everything it takes to win. That might mean getting deep into the weeds of your business, or it might mean hiring well and getting out of the way. If you are relentless about championing the vision, if you create a culture of people who care, if you give ownership, and when you demand excellence, you are more likely to win.

The choice here is not Founder Mode versus Manager Mode. The choice is to give a shit or don’t give a shit. Building something great requires giving a shit. After that, there is no right or wrong way.

Does the Head of Product Need to Be the Best Product Manager on the Team?

I’ve had this blog post in my head for a couple weeks now. I’ve been thinking about how to lay out a strong case for what I momentarily thought was a controversial topic. I figured the post would be long and go to great lengths to help readers come to the conclusion that I have.

But guess what? None of that is needed. there is such an easy answer to the question: “Should the head of Product Need to Be the Best Product Manager on the Team?”

No.

So why did I go on this journey? It was a moment of weakness that I don’t mind admitting to. Recently, I’ve had a bunch of great conversations with founders preparing to hire their first head of Product (VP, CPO, HoP). To my surprise, more than one has directly said or strongly implied that they expect their new Product leader to be “the best Product Manager on the team.”

In every leadership role I’ve been in, I’ve had at least one team member that I believe to be a better PM than I ever have been, and I have always seen that as a good thing. At the same time, I also believed myself to be the best and most capable of leading the functions I was responsible for. I guess these chats with talented CEOs made me start to doubt myself and I began pondering this question, assessing my own skills and abilities.

I don’t believe that anyone expects a CTO to be the best software developer on an engineering team. We don’t expect the CMO to be the best visual designer on the creative team. Why would we expect the CPO to be the best Product Manager on the team?

This may be cliche, but I used a sports analogy to help me put this question to rest: Steve Kerr, the Head Coach of the Golden State Warriors NBA team was not the best basketball player on any of his teams when he was a championship winning player (not even close). Yet, today he is recognized as one of the best coaches in the NBA over the past 10 years. Kerr will one day be inducted into the NBA Hall of Fame, and it will be because of his coaching career, not his playing career. He is a talented and effective leader of players that are all better than he was.

Conversely, LeBron James can arguably play all 5 basketball positions at a high level, and he is considered by many to be the best basketball player of all-time, but we have no idea if he’d be a good coach. In fact, he probably wouldn’t be. If you look at ESPN’s top 40 NBA players of all time, you’ll only find three that have had some notable success as a coach, and not a single one even close to being one of the best coaches in any given year, let alone the history of the NBA.

Why is this? The job is totally different! The skills needed to be a top tier coach are completely different from the skills needed to be a top tier team member.

If Steve Kerr thought that he was the best player, and didn’t try to “hire” players better than him, I suspect that the Golden State Warriors wouldn’t have any of their four championship titles in the last nine years, and Kerr would have been fired long ago.

Just as the jobs are different in sports, the jobs are also different in software product management. A highly talented head of Product is focused on building and up-skilling the best team they can assemble. They create an environment and playbook that allows each team member to be their best and play the role the team needs them. They are the expert when it comes to the customer and the competitors. The head of Product connects the organization’s goals to execution in the area by setting, owning, and championing a strategy to build the right products, for the right market, with the right investment, at the right time.

If you haven’t been a Product Manager, it will be much harder to be great at the things a head of Product needs to do. You don’t need to have been the best PM, but you better know the job inside and out, have witnessed it done well, and have recognized when it was done poorly (even if that was you).

That brings us to what I believe the head of Product does need to be the best at:

  1. Setting vision & strategy: As a member of the company’s senior leadership group, you play a pivotal role in setting and guiding company vision, while owning a product strategy that guides the organization towards achieving that vision. Good strategy considers current customer needs, where the market is headed next, and what the company’s long term vision is. All packaged so that it is clear to all what the priorities are, why, and how we’ll act in order to reach defined goals.

  2. Recognizing trends and opportunities: Product Managers and Engineers focus heavily on shipping products to satisfy a problem that exists today. While PMs are not exempt from seeing and planning for the future, I expect the head of Product to be the first to see where the market is going, to spot emerging trends, to find hidden opportunities, and then decide when and how much to invest today for big rewards tomorrow. Product leaders do this by being out in the market with customers (literally and figuratively), building user empathy, becoming a trusted advisor, and acting as a continuous student of the industry. The right team, in the right positions, with the right playcalling is a multiplying force that exceeds anything that a head of Product could ever be on their own.

  3. Recruiting & nurturing talent: Product orgs operate at their best when they have the right people, in the right position, with the right coaching. It's not just about finding the best fit, it's also about convincing them to join the journey, coaching them to be their best, while fostering interest and excitement in the work. It’s not just about having the right people with the right skills, the head of Product needs to foster an environment and process that invites partnership from engineering through the Product Manager’s effective communication around the “what,” “why,” and “when” of their priorities.

  4. Facilitating cross-team collaboration: Great product doesn’t mean much if it can’t be effectively marketed, sold, and supported. Engineering isn’t the only team that product managers must work well with. An effective product leader makes sure their team does not work in isolation. They expect their product managers to influence Marketing, Sales, Support, and other functions by partnering with the leaders of these functions and to set an example of collaboration and paving the way for two-way relationships that benefit customers and the business.

  5. Communicating well: Absolutely everything in this list is dependent on being a fantastic communicator. I often say that product leaders really only do three deceivingly simple things: They listen (to customers, data, colleagues, etc), they think (about priorities, investment levels, timing, visions, strategy, etc), and they communicate (to win support, create understanding, set goals, etc). Being an effective communicator means winning support for strategy because it is clear, relatable, and powerful. Being a great communicator means selling the org on taking the right risks, at the right time. Being a stellar communicator means getting the best talent to jump in the boat with you and give it their all. A mastery of communication results in strong ties to customers where trust leads to openness and partnership.

Curious to see my thoughts on other aspects of Product Management? See those posts here. To see the conversations on this topic from the r/productmanagement Reddit sub, head over here.

Comparing Portugal and Oregon's drug decriminalization policies

I am lucky to be spending time in Portugal right now. Not vacation time, but an extended “live like a local” amount of time. Lisbon, where I am based, is beautiful and I am really enjoying it. The entire country is fantastic, and as you have probably heard from others over the last few years, it is (was) a hidden gem in Europe that deserves your attention.

While Portugal is still reemerging onto the global stage (after all, through history, Portugal used to be one of the most powerful and wealthy countries), there is one thing that many people are aware of: the country’s decriminalization of recreational drug use. (Please make sure to read the disclosure statement at the end of this post, it provides important context about the following paragraphs.)

In 2001, Portugal made a bold shift in its approach to drug use by decriminalizing the possession of all drugs for personal use, a move that pivoted the nation's drug policy from a framework of criminal justice to one of public health. Drug use is not legal, rather under this groundbreaking policy, individuals found with drugs within a set amount for personal use are not criminally charged but are instead referred to Dissuasion Commissions, which assess the need for treatment, harm reduction, and social reintegration. This paradigm shift, aimed at treating drug addiction as a health issue rather than a criminal one, has led to significant public health, safety, and addiction improvements, setting a precedent for drug policy reform worldwide.

Nearly 20 years later, my home state of Oregon in the US passed a similar drug decriminalization law. The ballot measure that voters approved is called Measure 110, and it passed with 58% support, with nearly 400,000 more “yes” votes than “no.” This new law and the surrounding policies are said to have been inspired and modeled directly after Portugal’s.

Fast forward to 2023, and many Oregonians, including myself, believe Oregon’s Measure 110 to be a complete and total failure. Fentanyl use is rampant, as is addiction, mental health issues, and homelessness…all four being tightly related to each other.

Everything I have read over the years about Portugal’s policy and it’s impact, as well as my experience in the country as a traveler leads me to support and admire what Portugal has done. So then why don’t I support what is happening in Oregon?

I was sitting in my favorite craft beer bar in Lisbon the other day, when I overheard a group of Americans saying that they understood Portland to have decriminalized drugs, but they also understood the city to be a mess. So I chimed in. I told them that it was Oregon, not Portland, that decriminalized drug use, and as much as I love Portland, I have to admit that they are right, the city is a mess right now due to drug sales and use. They then asked my why I didn’t think decriminalization worked in Oregon.

Here is why: Oregon decriminalized, Portugal decriminalized and then invested heavily in policy, programs, and infrastructure to support their people and prevent addiction as much as they can.

As far as I can tell, Oregon simply decriminalized use, made some token changes to an existing, ineffective drug dissuasion and treatment policy, and called it a day. Sure, the law includes a plan to invest more into treatment and recovery, but the thousands of addicts on our streets don’t seem to be getting access to those resources. From what I can tell, the support Oregon offers is still a loosely connected, complex network of third parties, that have not been effective to date. There is even a phone number you can call to get help! I wonder how often that gets used? (sarcasm)

It would seem that Oregon’s approach is nothing like Portugal’s! Both Oregon and Portugal continue to target and persecute the criminal sale and trafficking of drugs, but that is about where the similarities end. Putting words in the text of a law is different than doing what is needed.

Portugal has effectively said “We won’t treat you like a criminal for using drugs, but we will help you to not ruin your life, not ruin the lives of those around you, and not ruin our country.” They do this with a multi-pronged approach that is aimed at non-users, casual users, frequent users, and addicts. Oregon seems to say “We won’t treat you like a criminal. You are on your own to find the limited resources that exist to get help, if you want it.”

Portugal starts with prevention programs in schools and to the general public that uses a comprehensive approach based on data and wellbeing. Unlike many programs in the United States, the program is not focused on zero-tolerance, because that is not the human reality (abstinence-based sex education, anyone?).

If you do use drugs and get caught, you are given what is essentially the equivalent of a traffic ticket. It isn’t just a ticket that you pay, instead you are called in front of a Dissuasion Commission. This commission, which sounds a bit like a jury or a parole board, will seek to understand your situation, and then impose fines, order community service, enroll you into education programs, send you to drug treatment, put you on probation, and.or even suspend professional licenses. In other words, there are still penalties, but there is also significant social and health support.

Effective and accessible drug treatment seems to be a problem in Oregon. In Portugal, they have ensured infrastructure to make sure treatment happens. Here is another critical factor: Portugal has a social healthcare system. There are no financial barriers to treatment in Portugal. If you need it, you can get it at no cost. No arguing about who pays. No questions about insurance coverage. No financial reason not to get treated. This couldn’t be more different than in America where health insurance is typically tied to work, mental and addiction care coverage is typically different than medical care coverage, navigating programs for low-income citizens is complicated, and the entire industry is profit seeking.

I will be the first to tell you that I am no expert in healthcare, public policy, or the drug trade. I can however share my observations from Portugal.

In what is a relatively poor country by European and American standards, I see significantly fewer homeless people here than I do in Oregon. I haven’t once seen open air drug use or sales, something that I see about once per week in Portland. I’m not scared to walk down the street in a “bad” part of Lisbon at night. Drug use does not appear to be ruining lives, or the city, in any noticable way. (That said, I am an outsider, I don’t live here, and I haven’t experienced all aspects of these policies or programs, so I could be wrong).

More notable than just my observations is what the data says. Since decriminalization and policies for education, support, and treatment went into effect, Portugal has improved across a number of key metrics. The rate of drug addiction went down, and is now one of the lowest in Europe. Drug related deaths went down dramatically on a per capita basis, and is also one of the lowest in Europe. Additionally, the transmission of HIV plummeted, and is again one of the lowest in Europe. Finally, teens and adults in Portugal are some of the least likely in Europe to ever use cocaine or cannabis. It should be noted that there is evidence of some age groups having increased rates of addition and death, during different periods since decriminalization.

So was Oregon wrong to decriminalize drug use? In my opinion, Oregon was wrong to decriminalize without also investing more, and more effectively, into education, prevention, and most importantly, treatment. It is also my opinion that if you believe that Oregon, any state, or the country is doing enough to counterbalance decriminalization, or if you don’t think it is the responsibility of the government to provide these things in order to have a functioning society, you need a wakeup call. Why only fund policing without funding programs to keep people out of police trouble?

A note about the author, sources, data, and contents of this blog post.

First and foremost, I am not an expert in the topics explored here. Much of this blog post is based on my opinion, personal understandings, observations, and readings. I believe my knowledge to be accurate and reasonably complete, but that is likely not the case from an objective, outside point of view.

Additionally, I have used two different chatbots (ChatGPT 4.0 and Bard) to help educate myself on these topics, including the use of them to cross-reference each other for accuracy. Chatbots can and often are wrong. The sources used by me and these chatbots include: The Cato Institute, The European Monitoring Centre for Drugs and Drug Addiction (EMCDDA), The Obama Whitehouse, the UK’s Transform Drug Policy Foundation, Portuguese Government reports, and the United Nations Office on Drugs and Crime (UNODC).

It is also important to note that there is not yet comprehensive, comparable studies or reporting on effectiveness and outcomes in Oregon, as only three years has passed since decriminalization was approved by voters. Trustworthy data collection and research on a sweeping change like this often takes much longer than three years. Therefore, the parts in this blog post about Oregon are heavily based on my own opinion, observation, and limited education on the topic.

The Dumbing Down of American Democracy

Recently, I’ve been thinking a lot about a style of communication that I see from politicians and other public figures, and it is really getting to me. It’s not a just a general style of communication, it is specific to politics, government, and our free society. I'm talking about the clownish oversimplification where every issue, idea, or person is slapped with a "Democrat" or "Republican" sticker. These labels are then used to validate or invalidate ideas, actions, and people. It's as if these statement should tell us all we need to know, like the nutritional facts on a box of cereal. But life, democracy, and politics just isn't that simple.

Take Donald Trump, who seems to see the world through a red-and-blue kaleidoscope. He's been in hot water more times than a lobster at a seafood buffet, and his go-to defense? Pointing fingers at "partisan" judges, juries, prosecutors, and attorneys. Like when he was found liable for sexual abuse and immediately called the judge and jurors "partisan," telling them to be "ashamed of themselves” ¹. Or when he slammed a "Clinton appointed judge" on Truth Social for giving him what he felt was an unfair trial simply because of the President that nominated them decades earlier, with no other reason or evidence ². Most recently, Trump implied that his civil fraud trial will be unfair because he believes that the court clerk is the girlfriend of Democratic Senate majority leader Chuck Schumer ³. He's not just turning courtroom drama into political theater, he is implying that people cannot think or act outside of the box of their political party.

Elon Musk gave us another recent example himself. Chiming in on the Joe Rogan podcast, he claimed Twitter was suppressing Republican tweets 10x more than Democrats. But here's a reality check: Tweets get the boot for spewing dangerous lies, hate, or violence, not party allegiance. Let's ask the uncomfortable question—could it be that one side is tweeting significantly more stuff that crosses the line? I don't have a spreadsheet handy to prove it, but come on, the last 10 years in America shows us enough.

Musk, someone believed by many to be one of the smartest people on earth, is mixing up causation and correlation. Is this out of ignorance or, worse, a calculated move to drive a wedge right through the fabric of America?

I am nowhere close to being the smartest person on earth, and yet I clearly understand the differences between correlation and causation. The concept is a basic rule of logical thinking.

So what’s going on? I’ll tell you what I believe: Politicians and big shots like Trump and Musk are either showing the world their lack of smarts or, more sinisterly, they're deliberately playing the pied piper leading us off the cliffs of division. Because of this, America is at a wildly dangerous point in history.

Why do I say that? Well, because these people influence, millions of people listen to them. They eat up these oversimplified, misleading morsels and spit them back out. Every time they do, they chip away at the trust we've got in our system—our courts, our laws, our very democracy. America is built on this trust, the kind that lets us put power in the hands of the people, where politicians are supposed to be our servants, not sultans.

I worry about what happens when that trust goes away. Down comes the house of cards. We've seen it throughout history. Fascist regimes and dictators are elected because people believe they will be the heros that will save the system, the only people that can act without bias. Of course, they aren’t the heros, they don't hand power back to the people. They keep it, and they do whatever it takes to keep their grip tight.

We've got to stand up to this bullshit. Call it out. Tell Trump, Musk, and their ilk that we're not buying what they're selling. We're better than that. We're smarter, more logical, and too dang stubborn to let our democracy get bulldozed by a tweet or a sound bite. And when I see we, I mean all American’s, regardless of political party affiliation. I believe most of us have it inside to be smart, fair, factual, locial, and unbiased if we want to. Don’t let Trump, Musk, and others push that inherent intelligence down into hiding, let it shine.

So, the next time you're chatting about politics with someone who's parroting these divisive lines, hit them with facts, with calm-reason, with the kind of clear-eyed logic that's been the bedrock of this country. Remind them—and maybe ourselves—that we're capable of more, that we're the land of the free thinkers, not the blindly led.

If we don’t, we might just find ourselves in a history book chapter titled "How to Lose a Democracy 101." And with world tensions flaring up in Ukraine and Israel, our democracy needs to be on solid ground more than ever. We can't let it be shaken by those who'd rather see us divided for their own gain or ego. Let's keep our heads, our hearts, and our freedom intact.

The Shocking Reality of Dynamic Airline Pricing: A Personal Experience with United Airlines

Last night, my wife and I made the decision to book flights for an upcoming trip. We have a long-standing loyalty to United Airlines, having earned significant status over the years. On occasion, we opt to book our flights separately, each of us paying for our own ticket, yet flying on identical routes. What transpired during this booking process was both startling and infuriating, shedding light on the complex algorithms that govern airline pricing.

Understanding Dynamic Pricing

It's no secret that airlines employ dynamic pricing strategies, which I assume are primarily influenced by supply and demand, as well as timing. There have also been whispers that your geographical location at the time of booking can impact the price you're offered. For instance, it's rumored that individuals booking from Europe may receive more favorable rates for domestic U.S. flights than those booking from within the United States. While I had always been somewhat skeptical of this claim, my recent experience has made me a firm believer.

I am now convinced that airlines are not only leveraging location as a factor for dynamic pricing, but also a multitude of other factors that define you as a person and consumer. This is akin to Instagram suggesting a sweatshirt that complements the t-shirt you just purchased (prior purchase history), or a San Francisco-based startup CEO being targeted with ads for private jet travel (work and income). In the case of airlines, they may also be using data such as your travel frequency, preferred destinations, family size, and more to tailor your pricing.

A Real-Life Example

Here's what unfolded last night that solidified my belief in this theory. My wife suggested we book our flights for a trip we have planned next month. She quickly found a round-trip fare for $288 and proceeded to book her ticket. While sitting next to her, I searched for the same flights, on the same days, and with the same tier of frequent flyer status. Astonishingly, my fare came out to be $222—a 23% discount compared to my wife's rate.

But the story doesn't end there. I soon realized that I had inadvertently used my work credit card for the booking. Upon contacting customer service via the mobile app's live chat feature, I was informed that the payment method couldn't be changed; I would have to cancel and rebook. Within a mere 10 minutes of my initial booking, I found that the price had escalated to $241—a 9% increase.

The Implications

We were quoted three different prices for the exact same flight, all within a span of 10 minutes, and under identical conditions—Same wifi, same type of device, same app, no VPN. While these fluctuations may not significantly impact our wallets, consider a 23% price difference on an international flight costing $2,000; one traveler could end up paying $460 more than another.

I have a few other trips that I still need to book, so I intend to further investigate this phenomenon by experimenting with various booking conditions, such as using a VPN, logging in and out of the United app, and employing incognito mode. I will share my findings in a subsequent post. I can’t wait to see what happens.

Is This Legal?

This experience raises questions about the legality of such pricing strategies. Is it lawful to charge different prices for the same service based on factors like income, employment, or IP address? It probably is legal in the US, but it certainly is concerning. As a consumer, I prefer price transparency and equal treatment. Sure, price based on supply/demand, but charge me the same as you charge my neighbor. That’s what I get when I go to a restaurant, buy electronics, or purchase a ticket to a concert. I don’t think it is too much to ask for from an airline.