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

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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

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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

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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.

When I do it again

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In what feels like a lifetime ago, I decided to build my first, real startup. From February 2010 to February 2014, I served as the co-Founder and CEO of a small company named CPUsage. Me and two amazing co-founders took a crazy idea, explored a big problem space, began building a prototype, raised venture capital, built a team, built a couple products, flirted with providing value to a market, and then failed miserably. Four years, about a million in outside funding, destroyed personal lives and finances of at least one co-founder, and we had nothing to show for it. No meaningful revenue, no product worth something to others, no acqui-hire.

These were the most enjoyable and educational years of my career! I loved every minute of it! I learned more than I imagine an MBA or any set of degrees could teach. I’m a better human for this experience, and a better professional. Failure and all.

I learned so much about so many things, and in this blog post today, I want to focus on what I learned about what it takes to be successful when starting a company. Specifically doing so with the intent to innovate, grow rapidly, and return outsized rewards to employees and investors….in other words, a startup.

I try to limit regret in my life, but I do seek opportunities to improve myself by learning from my past. Through my experiences co-founding and leading CPUsage from 2010-2014, here is some of what I’ll do differently next time I start a startup.

Go deeper with potential customers

In short, I became a Product Manager after CPUsage because I quickly realized that we failed in part due to one specific reason: we didn’t go deep enough with customer discovery. We talked to a bunch of people, there was no shortage of potential clients or simply just people to learn from. The problem is that we got too excited, too easily. We stayed at the top level of the problem, we didn’t dig deeper to understand the root of their problem or how truly painful it was. We heard what we wanted to hear, went back and built what we thought the potential customer wanted, and then they never used it.

There was clearly a problem, and it was painful. We just didn’t know exactly where the pain emanated from, which meant we couldn’t prescribe the right medicine. We sought what we wanted to hear, not what we needed to hear.

I became a Product Manager because I wanted to master customer discovery and make sure I was equipped to prevent this mistake again. I loved building software, but I wasn’t going to build truly great software until I figured this out. Big thanks to Todd Etchieson for believing in me and giving me that opportunity at New Relic!

The next time I build a startup, I’ll do what I’ve done as a Product Manager since CPUsage: be relentless with customer discovery, seek deep understanding of the problem space, and build products that are 10x better or 1/10th the cost of the alternative.

Have a REAL go-to-market plan

So it turns out that taking a product to market is more than posting about it on Twitter or Hacker News and hoping people will come use it. Who knew?! Through my experience at CPUsage, I learned that my world may seem big and important, but it is just a spec in the universe of software, technology, and the market I am going after.

We honestly had no plan, and no idea how to win customers. We were building a two-sided market and easily figured out how to capture the supply side, but didn’t tackle the demand side. Seems obvious now, but it was far from obvious then. Tell a few friends and it will take off, right?

The next time I start a company, I’ll think about go-to-market from day one. We’ll make demand capture and distribution an inherent aspect of the product. Just because you build it, doesn’t mean they will come.

Focus spending

I now know that in the early stages of a software startup, the most important thing to invest in is customer validation with product. There is little that you can spend money on that is as, or more important than, putting product in the hands of customers and prospects to learn from, and adapt to. Almost anything else is a distraction and likely doesn’t produce significant enterprise value.

Don’t hire sales people. There is no need for a CMO or even a marketing intern. It’s all about engineering at the pre-seed and seed stage. The co-founders can do the rest. Spend to learn, and learn through the eyes of your customers and prospects as they use (or don’t use) your product.

Seek accountability

If it isn’t obvious yet, I should tell you that my co-founders and I had never started a company before, never took funding, never built a real product outside of our day jobs. Not only did we need help, people to guide us, and hold us accountable…we didn’t even know we needed this. As the saying goes, we didn’t know what we didn’t know.

Within weeks our initial close of funding, we attended a portfolio event for our lead investor. For some reason, we thought this was the right time to ask our lead, “you gave us money but didn’t ask for a board seat, don’t you want one?” He probably laughed inside, and then told us that as a seed-stage company without a complete product or any customers, we didn’t need the overhead of a board. We should just focus on building our product, and let him know if/when we needed help.

We didn’t take him up on that offer enough. We talked to our investors frequently, but we were mostly on our own. We asked for help, but in hindsight we only asked for help a fraction of the time we should have, in part because we didn’t know we needed help.

We may not have needed a traditional board of directors at that point, but we certainly needed the accountability that a board with investors/outsiders provides, along with the sense of “in it together” that I believe board members share with founders.

When I do it again, I’ll ensure that I have a framework in place to hold myself more accountable. It may be a board with investors/outsiders in the early days, it may be advisors, it may be a peer group, it will probably be all of the above. Regardless of the form, I’ll seek accountability, asking others to say the things that are heard to hear, tell me when I am wrong, set high expectations, and ultimately walk with me on the journey. Business success is no one’s responsibility except the founders, but we can’t do it alone. That’s just human nature.

More goal setting

Especially in the early stages of a company, it’s simply impossible to plan very far into the future (you decide what “very far” means). That doesn’t mean you can’t plan, and those plans better be more specific than “build valuable things that people will pay for.” How will you know what the thing should be? How will you know when you’ve gotten here? How will you know what valuable means? I may not know what I need to do every day between now and ultimate business success, but I can predict with high degrees of certainty what questions need to be answered, and what milestones must be reached.

When I do it again, my co-founder(s) and I will drive our work from questions we know need to be answered, and milestones we believe need to be met. We’ll put short term and long term goals in front of ourselves. We’ll commit to doing achievable things in the near-term, then do them. We’ll create inflection points and forks in the road, and we’ll ask others to hold us accountable to these things. All this will be done while being firm on the vision and flexible on the details, giving ourselves room to be wrong, or change our minds, in service of the goal.

Fail faster

Did you catch this earlier in the post? About one million dollars and four years? As first-time founders, we falsely believed that stretching our money out as long as possible would give us the best opportunity to learn and build for success. We were so, so wrong! Our frugality meant we did less, in more time, and impacted our ability to learn quickly, from meaningful product development. Sure, we had 4 years to learn, but those learnings were each less valuable than they would have been had we gotten them in 12-18 months, instead of 48. In fact, we would have had a better chance at success had we spent the same amount of money over a shorter period of time. Building more, more iteratively, and more quickly would have created enterprise value. Both in the product itself and the trust we’d have built in our investors and customers. We would have had a better chance because we would have pivoted sooner, but also because we’d have more people believing in us and rooting us on, including ourselves.

We failed too slow because we made all the other mistakes listed above. We didn’t set specific enough short term goals and questions to answer. We didn’t have a framework to keep ourselves accountable to this work. We didn’t spend purposefully to develop products we could learn from. We had no clue how to get our product in the hands of customers. We didn’t really listen to the problem within the problem when speaking to the market or customers. All of these mistakes ate up time. Sure, they ate up money too, but most importantly they ate up time.

The above isn’t an exhaustive list of what I learned the first time I was an entrepreneur, nor is it a complete list of the things I’ll do differently. I am inspired not only by my experience as a first time, early stage entrepreneur, but also through my work in Product Management at New Relic, Pagerduty, and then Zenput. I also love to read and have found The Hard Thing About Hard Things by Ben Horowitz and Sprint by Jake Knapp & John Zeratsky to be incredible sources of inspiration and learning.

I’d also like to thank the people that gave me the opportunity to learn these things, and support me through the experience: Our investors (Ash, Ben, Eric, Omar, Damien), my co-founders (Matt and Shiv), our families (for me: Richard, Gayle, Kristin, Nate, Sabrina, and more), and our friends (including, but not limited to: Robert, Ken, Mike, Bill, Justin, Dionna, Shashi, and more).

Oh, and one last thing. I am doing it again. Now, today, this month, all this year, and next year! I can’t wait, not just to do it, but to do it better this time! Watch this space for more.