Author Archives: Casey Winters

What Type of Job is This: My First Year as Chief Product Officer

I have written about the Chief Product Officer role in the past, and why the job is so hard. I also wrote about being a product leader during a crisis. But not much is written about starting as a new product leader. So, I thought I’d write a post about my first year as CPO, and share some general lessons. First, a reminder of the situation I started in. I had been an advisor for Eventbrite for about two years, so I had a lot of comfort with the CEO and many of the executives before ever starting the role. I believe this is an underrated way to start new roles for senior people because you can de-risk the culture fit and alignment issues that plague many new executives. When I started advising Eventbrite, the company had a business unit structure, so it didn’t even have a CPO role, but product leaders embedded into different business units. The company reorganized functionally, and created this role and asked me to consider it.

What Type of Job is This?
I believe the most important question a product leader needs to ask when they get started is what type of job it is they have to do. I wrote in the past that there is frequently a misalignment on vision vs. execution roles. There may also be a misconception of what type of product work is needed to help the company i.e what the product strategy should actually be. In the Reforge Product Strategy course, we teach that there are four different types of product work:

  • Feature development: adding new things to the product that improve value proposition e.g. Uber’s Split Fare
  • Product/market fit expansion: adding totally new products that create new value propositions e.g. Uber Eats
  • Growth: tuning the product experience so more people can connect to the current product’s value prop e.g. Uber improving driver onboarding
  • Scaling work: tuning the underlying technologies or process to help the product and team continue to be effective e.g. Uber rearchitecting its data pipelines

Old school product leaders would just do their preferred type of product work even if it wasn’t what the company needed, or adopt a primitive portfolio approach to the four types of work even if part of the portfolio was wasted work e.g. building a ton of features for a network effects business, or doing a lot of growth work for a pre-product/market fit product. As a modern product leader, it’s important to understand based on the company and its lifecycle, what type of product work has leverage, and these crude approaches are usually not the best approach.

Usually, the best place to start is looking at what the company is actually working on right now. In Eventbrite’s case, the company was:

  • Integrating the acquisition of Ticketfly to move up-market in a specific vertical and build an enterprise sales motion
  • Building a consumer marketplace to drive incremental ticket sales to event creators
  • Paying down technical debt with duplicate versions of Checkout and Create
  • Launching a developer platform so external developers can add more features for Eventbrite’s broad base of event creators
  • Launching new SaaS products with its incubation arm

Julia, our CEO, had told me she wanted me to focus on growing the self-service business faster. So, first off, what you should notice is that there are too many things going on for a company of Eventbrite’s size (sub one thousand people). In other words, the product strategy lacked focus. So, I had to spend my first few months understanding these different strategies to understand which ones to focus on. So I gathered as much information as I could about these different strategic initiatives, as well as digging into the core self-service business.

What Was Going On With the Core Business?
The core self-service business was growing steadily at significant scale and was profitable. Most of the sales clients we brought in stressed our product/market fit, which we compensated for with manual services at no charge, straining margins. We didn’t have a good sense of who our self-serve customers were, how we acquired them, or what retention looked like. As we dug into these questions, we found that while Eventbrite’s product/market fit was strongest with making it really easy to host a single event, but the bulk of our growth and profit was coming from frequent creators hosting small events very often. So, while the product roadmap was scaling for size of event, the market was scaling with frequency of event. The product did not handle this frequency very well, causing these event creators to hack the product to get what they needed, and a higher churn rate over time as those hacks proved problematic to execute. The gaps in our product to strengthen product/market fit for these creators didn’t seem insurmountable, but none of them were actually on the roadmap.

We also were able to get a clear picture of the core competencies and competitive advantages of the Eventbrite product. The fact that Eventbrite supported events of all types and wasn’t focused on one vertical e.g. conferences meant the company had a scale of data no other company had. Secondly, the self-service acquisition model meant the product had very low acquisition costs overall. That model was also a good fit for many different types of creators. Lastly, the company had leveraged its scale of events to drive consumer demand through channels like SEO, emails to previous ticket buyers, and distribution partnerships with companies like Facebook and Spotify.

What Did the Team Say?
As I talked with the team about the state of the product and what they were actually working on, let’s just say the team had a lot to say. Breaking it down by project:

Upmarket Music Vertical Expansion
We tried to integrate music customers too quickly into the Eventbrite platform, and we were much further away from product/market fit with the more traditional enterprise approach those customers were used to than we thought. The space is low growth and low margin, and relies on enterprise sales, relationships, and high touch human service, which doesn’t match our self-service capabilities well.

Consumer Marketplace
Frequent creators drive most of the inventory consumers are interested in, and if frequent creators’ efficiency tools on Eventbrite don’t work for them, they will leave the platform even if they sell extra tickets because of the platform. This is an interesting strategy, but needs to be sequenced after we have a great product experience for frequent creators.

Technical Scaling
Internal developer productivity was incredibly low due to low level of investment in developer tools. Our infrastructure was rickety and frequently had stability problems during big “on sales”. Multiple versions of every feature made it hard to build new things quickly and at high quality. We never deleted features because some sales clients use them and would complain. Everything we build is an MVP, and we rarely iterate.

Developer Platform
While the strategy of leveraging external developers to build specific features for a large array of customers with different needs makes sense at Eventbrite’s scale, we internally lacked the capability to service our own engineers well, much less external developers.

New SaaS Products
Many of these products are very far away from product/market fit and do not have a path to scalability. There is one partnership related to creator marketing tools being run out of this program which is doing well though, and it has been easier to talk with creators about that than our marketplace demand.

Developing A New Product Strategy
Strategy is about making choices among many options that optimize across a few key dimensions like:

  • Company Focus
  • Business Model
  • Target Customer & Market
  • Competition
  • Core Competencies & Competitive Advantages
  • Consequences & Risk
  • Sequencing

Eventbrite failed to make a lot of hard choices with its product strategy when I arrived, so it was time to make some tough calls on what to focus on. There are no simple answers here, but in evaluating the initial strategy, it became clear we should do the following:

  • Upmarket Music Vertical Expansion: We are too far away from product/market fit trying to rebuild the Ticketfly model, and there is little margin or growth to be had once we get there. There is a lot of competition, and the go-to market approach leans out of our core competencies. It felt like we were trying to win the music industry’s last war instead of building a more technology-forward experience many up and coming music venues would appreciate. We need to focus our music creators towards a self-service experience like the rest of our product, and if that means that some of the less tech savvy customers won’t come with us on that journey, that’s okay.
  • Consumer Marketplace: The product needs to have a good experience for frequent creators before they will value our demand, and we should probably help them improve their efforts to drive their own demand first. Sequence to this strategy when frequent creators are in a good state.
  • Technical Scaling: Developer velocity is the purest form of leverage in a software company. We should be investing more in this area so we can increase our strategic appetite over time.
  • Developer Platform: If we are not providing a great experience for our own developers to build great features, we are even less likely to provide a great experience for external developers. Pause until our technical infrastructure is in a much better place.
  • New SaaS Products: Creators drive the majority of ticket sales through their own marketing efforts, and they are not expert marketers. Our knowledge can help them improve and automate their efforts. Cancel everything else in this area.
  • Core Self-Service Growth: Make the product experience great for frequent creators of small events as they drive most of the profit for the core business. We are not far away from strong product/market fit here.

The new product strategy is remarkably simpler and more sequenced over time:

2021

2022

2023

Frequent Creators

Marketing Tools

Consumer Marketplace

Technical Scaling Technical Scaling

Technical Scaling

Frequent creator investment will be measured by improved frequent creator retention. Technical scaling will be measured by internal developer velocity and our say/do ratio. Marketing tools and consumer marketplace will both be measured by revenue from those sources. So, going back to what type of job this is, my initial directive would have made this product leadership role to be primarily about growth. Instead, the focus is on scaling with some product/market fit expansion. 

Your Product Strategy Probably Isn’t That innovative
One dirty secret behind the work of many executives and product leaders is that our strategies aren’t that innovative. There are a few playbooks we generally run to improve performance in companies depending on the business situation after we’ve gathered the right insight. You can run through them and rule most of them out like the con men strategies in Ocean’s 12:

Yes, product leaders also rule out strategies because we don’t have enough people or can’t train a cat that quickly.

The new Eventbrite strategy was a combo of two common strategic playbooks. The first part of the strategy is what Chris Zook calls “profiting from the core”:

“The greatest strategic error stems from an inaccurate understanding of the core and its full potential.”
-Chris Zook, Author of Profit from the Core

However, if you’re an Arrested Development fan, you might call it the “there’s always money in the banana stand” strategy. The idea behind this strategy is that many companies as they scale pursue too many expansion strategies and leave behind growth that is closer to their initial core business, plays more to their core competencies, and requires less work and less risk to execute. Eventbrite was pursuing expansions in verticals (music), business model expansion (SaaS), and value props (driving demand) while ignoring improvements that could help the growth of the core product (features for small, frequent creators). At Pinterest, VP Product Jack Chou ran a version of this he called “make the basics great”.

The other component of the strategy is probably most known from a blog post (and soon to be book) by current Snowflake and former ServiceNow CEO Frank Slootman. In Amp It Up, Frank Slootman basically divides up his strategy into three elements:

  • Improving velocity
  • Raising standards
  • Narrowing the focus

Personally, I would flip the order and revise the language to be more software specific:

  • Improve focus
  • Raise quality bar
  • Reduce tech and design debt (usually the biggest hurdle for velocity inside software companies)

By the way, if you’re a public market private equity investor, and you aren’t running this strategy on every sub-rule of 40 tech company, I have a question for you.

So, in Ocean’s 12 language, Eventbrite is running a banana stand combined with a Slootman Special. We… may need to work on these code names. Recently, Etsy has run this same strategy combo to grow its market cap from $2 billion to $25 billion in four years after many years of no market cap growth at all.

There is one other element to Eventbrite’s strategy, and that is presented by the table above: sequencing vs. parallelizing. There is a reason Eventbrite started to pursue a lot of these adjacent opportunities in the first place: fear the core business could not grow itself fast enough. But in trying to pursue multiple adjacencies at the same time, it not only failed to make the progress it wanted on any of them, but many were not set up for success because they would gain from other strategic elements of the plan already having been completed.

The goal of this post is not to geek out on all the generic strategies, though I could do that all day, but to give a sense of the work new product leaders need to do to understand strategy and make it explicit to the organization. Frequently, there is a mismatch between what the customer or business needs and what the team is working on today. Usually, by talking to the team, your customers, and looking at the data, you can identify the mismatch and position the team toward a more likely to be successful product strategy. Then, product leaders can move to the meat of the role, which is building and optimizing the structure and processes of the team to execute against that strategy more effectively over time, or adjusting to changing market dynamics *cough* pandemic *cough*.

Currently listening to the Housewerk EPs by Tusken Raiders.

20Growth Podcast Interview with Harry Stebbings

Harry Stebbings of 20VC fame is launching a new podcast series focused on growth. I was happy to be his first guest. We talk about growth inside startups, how to hire for growth, and many other topics. You can listen to the podcast here or on Spotify below.

Currently listening to Mana Pool by VAPERROR.

Reforge Fall 21 Applications Now Open: Apply Today

I’m excited to announce that public applications are open for the Fall 2021 cohort of Reforge. I’ll be participating alongside leaders from Tinder, Facebook, HubSpot, SurveyMonkey, Instagram, and more.

[Apply to Join Reforge]

Reforge Membership includes participation in a cohort-based program and ongoing access to content from all programs, weekly releases, deep-dive sessions, and a community of vetted peers to help you execute what you learn.

Fall Programs Begin October 4th

I’ve worked closely with Brian Balfour (CEO at Reforge) and the Reforge team for the past 3 years to develop and host four different programs. Onboarding for the Fall 21 cohort begins Oct 4th and programs run between 4 to 6 weeks long.

Product Strategy

Build, communicate, and execute a cohesive product strategy across feature, growth, scaling, and innovation product work.

With Fareed Mosavat (GP at Reforge, Ex Slack, Instacart, Zynga), Ravi Mehta (Ex CPO at Tinder, Facebook, Tripadvisor)

Advanced Growth Strategy

A step-by-step system to create, analyze, and communicate a growth strategy of compounding growth loops.

With Casey Winters (CPO at Eventbrite, Ex Pinterest, Grubhub), Kevin Kwok (Ex Greylock Partners), and Fareed Mosavat (GP at Reforge, Ex Slack, Instacart, Zynga)

Retention + Engagement Deep Dive

A deep dive on how to understand, measure and improve retention through activation, engagement, and resurrection.

With Shaun Clowes (SVP Product at Mulesoft, Ex Metromile, Atlassian) and Adam Grenier (Ex Lambda School, Uber)

Growth for Founders

Gain critical growth tools to help your company traverse the next leg of its growth journey.

With Brian Balfour (CEO @ Reforge, Ex VP Growth @ HubSpot), Elena Verna (Growth Advisor to Miro, Netlify, MongoDB and Ex SVP at SurveyMonkey), Fareed Mosavat (GP at Reforge, Ex Slack, Instacart, Zynga), Ravi Mehta (Ex CPO at Tinder, Facebook, Tripadvisor)

Other Programs

In the Fall cohort there will be 14 total programs across Product, Growth, Engineering, Founders, and Marketing all built and led by experienced executives. Here is the full slate:

Reforge Membership: What You Get

Reforge is the first-ever career development membership focused on high-growth tech practitioners, and is built entirely around the idea of driving impact for your business and for your career. The Reforge membership combines cohort-based programs, with a year-round experience to help you learn, grow and drive meaningful impact in your career.

Live Cohort-Based Programs

Real problems require real depth. Membership includes participation in two cohort-based programs per year where you will go deep on how to solve a key problem in a 4-6 week, part-time, virtual format, guided by an executive.

Each week in a program, you can expect:

  • Around 3 hrs of deep content covering actionable frameworks and systems.
  • An expert-led case study with a featured guest to apply what you learned to a real-life situation.
  • Connecting with vetted peers solving similar problems through discussions and feedback.
  • Hands-on guidance by an Executive-In-Residence who has done the work before.

All Year Access to Tech’s Best Content & Curated Community

Your personal growth doesn’t stop with the program, it just begins. As a Reforge member you can:

  • Access all content across every Reforge program (over 14+ programs!)
  • Complete step-by-step projects to help you implement and execute what you learn.
  • Attend weekly workshops and deep-dive sessions by Reforge Partners.
  • Receive weekly releases of projects, examples, and cases.
  • Connect with vetted peers solving similar problems.

[Apply to Join Reforge]

Members Love Reforge

You’ll be joining other top operators from companies like Airbnb, Spotify, Stripe, Dropbox, Zoom, HubSpot, Reddit, and LinkedIn who consider Reforge one of the best professional investments they’ve made.

  • “Even for experienced practitioners, Reforge crystalizes a practical and easily explained series of handy frameworks and immediately gives you a way to approach almost any product in any industry.” – Scott Worthington, Dir of Product Marketing at Peloton
  • “Reforge has the best content of any educational resource that I’ve encountered. It’s the best way to accelerate your career in tech.” – Bangaly Kaba, Former Head of Growth at Instagram, Instacart
  • More reviews here…

Who Do I Learn From?

In addition to the experienced executives that build and lead our programs, you’ll hear examples from the industry’s best. Past featured guests have included:

  • Bangaly Kaba, ex-Head of Growth @ Instagram, Instacart
  • Dun Wang, CPO at Calm
  • Melissa Tan, ex-VP Product at Ro, ex-Head of Growth at Dropbox
  • Darius Contractor, Head of Growth at Airtable
  • Jiaona Zhang, VP Product at Webflow
  • Kelly Mayes, Sr Dir Product at Roblox
  • Adam Fishman, CPO at Imperfect Foods, ex-Patreon and Lyft
  • Crystal Widjaja, ex-SVP Growth at GoJek
  • Vaibhav Sahgal, VP Consumer Product at Reddit
  • Justin Bauer, EVP Product at Amplitude
  • Bela Stepanova, VP Product at Iterable
  • Angel Steger, Dir Product Design at Facebook, ex-Dropbox and Pinterest
  • David Bakey, ex-VP Consumer at Harry’s
  • Zindzi McCormick, Head of Activation at Slack
  • Kieran Flanagan, VP Growth/Marketing at HubSpot
  • And many more…

[Apply to Join Reforge]

To join the Fall cohort, you must apply before September 10th. Once accepted, seats are first-come, first-serve. If you have questions, contact hello@reforge.com. I hope to see you in the Reforge community!

Product Positioning and the Product Marketing Partnership

This was adapted from an internal blog post in collaboration with Tamara Mendelsohn, Eventbrite’s CMO. Slightly edited to make more sense for people outside of Eventbrite.

When you actually launch new products to customers (which many teams don’t do), product managers and designers that have focused on scaling issues and optimization have to flex a new type of cross-functional muscle: how to work with product marketing. The default mode of this partnership across the industry is beyond terrible. Product works in isolation on product, then at the last minute hands things off to product marketing to name it and “launch it”. Product marketing then does their best to come up with a brand forward approach to make the product or feature sexy to their customers, but more so for their portfolios or their friends. Marketing doesn’t match the product, dev teams are pissed that marketing doesn’t understand the feature, marketing is pissed they got brought in last minute, customers don’t know what the hell the thing the company released is and don’t use it. Rinse and repeat.

If you don’t want to do that at your company, you actually have to put in work to make sure the default mentioned above doesn’t happen, and for a company that isn’t in a rhythm of shipping new products and features over time, muscles can not be particularly well toned for that. Consider this post a workout training video that helps you understand how to tone those muscles and learn how to position products well so that customers adopt and understand.

The Brand Marketing Pyramid

If you’ve ever had the pleasure/misfortune of getting an MBA, you’ve likely suffered through a few mostly worthless marketing classes. But they’re not all bad. Perhaps the most important concept you can learn from these classes is how positioning works. If you’re positioning any product or feature or service, there are three different layers of branding that need to occur, and they get harder to execute the closer to the top you try to get:

  • functional benefits: what the features deliver
  • logical benefits: what the product enables you to do
  • emotional benefits: how it makes you feel

Most brands work their way up the pyramid over time. At first, they try to clearly describe what their product or service does, taking a list of features and translating them into benefits. As the brand learns more about what customers actually care about, they usually determine that focus isn’t as optimal as describing what the features actually enable — sometimes called “the job to be done.” Describing a phone as having “10 megapixels” (feature) means very little to most people, and even saying “higher resolution” (functional benefit) is often not as impactful as saying “it takes great pictures” (logical benefit), but it depends on the audience. If a brand gets really good at describing the functional and logical benefits, over time it tries to reach the customer with more emotional resonance: “Feel like a professional photographer” (which was basically the “Shot on iPhone” campaign). But Apple is able to do this because it’s built up high awareness of its features and functional benefits over time. 

Let’s take a look at how this evolved at Grubhub while I was there. When I joined the company, our tagline was “discover who delivers”, clearly what the company did. When we hired our Head of Marketing, we overhauled the brand and changed the tagline to “eating made easy”, more of the logical benefit. Eventually, we moved up the pyramid again to “happy eating”, an emotional benefit.

Once it all came together, Grubhub had a playful, visual style that resonated with young professionals, advertising that focused around the irrationality of hunger, and a nice mixture of emotional resonance, features, logical and functional benefits in its advertising.

While Grubhub got better at this type of work over time (and has gotten so much worse since that Head of marketing left), Nike and Apple are incredibly fantastic at this balance. While they receive accolades for their work at the top of the pyramid, they still do all the forms of positioning in different contexts.

Position

Apple

Nike

Features iPhone 12
5G speed. An advanced dual-camera system. Ceramic Shield for 4x better drop performance. And a brighter, more colorful OLED display.
The Lebron 17
Heel max air unit, air max zoom pods, high tenacity yarns, heat molded.
Functional Benefit iPhone SE
Small, secure, water resistant, long battery life.
Nike Joyride
Make running feel easy.
Logical Benefit iPhone privacy
iPhone lets me control who sees my data.
Built for Speed
I will go faster in these shoes.
Emotional Benefit Make Movies Like The Movies
You can be as awesome as this when you use the iPhone camera.
You Can’t Stop Us
Nike athletes defeat all odds. So can we during the pandemic.

Positioning Features Is Harder Than Positioning Products

I have a real appreciation for great brand marketing, because I personally suck at this shit. Ultimately, what great positioning does is provide potential customers a promise of the product experience. If branding obfuscates that, it’s not doing its job. This is why when many brands go for the emotional benefit without pairing it with the other elements of the pyramid, it doesn’t work. But the reason brands try to do this in the first place is there is a lot of value to be gained by pushing what the product can be considered for over time, and creating loyalty through emotional connection in the process. That shit is hard though! 

Positioning part of a product is even harder than normal positioning because the promise of the feature has to sit inside the broader context of the positioning for the overall product. Comprehension of how products work and what they can do is already incredibly difficult, so adding new elements to products compounds problems most products are already not good at. Product people tend to suck at positioning themselves. We’re often too wrapped in our jargon to speak in ways the customer understands. So we’re happy to have marketing take the lead. But the default mode of positioning features from marketing teams is to try to enfuse the brand into them without understanding how it can create even more comprehension issues. Scott Belsky, the Chief Product Office at Adobe, talks about how his startup initially got this wrong, and how it hurt comprehension (the whole post is great, but the example is in the “be more accommodating” section).

We faced this same issue when I was at Pinterest. When we launched the product internationally, retention was a lot lower than in the U.S. As we watched international users try the product, we realized that many were struggling with the key call to action saying “Pin it!”, which didn’t mean anything in their language. The product team wanted to change it to the local word for “Save”, but the brand marketing team was absolutely against it. We tried it anyway, and saw a 15% increase in activation rate, even in the U.S.! Our own brand was confusing users, the exact opposite of what it is supposed to do. We faced a similar issue from an SEO perspective. 

Our images were called “Pins”. By changing our title tags to say “images” instead of “Pins”, we received 5% more traffic from Google. There is plenty of time to get activated users to build an emotional connection with our brand, but if our brand makes the product not enticing to try or too confusing, it needs to back away until a later time when it can help, not hurt, company goals. Many times product and marketing teams will try to “go their own way” to solve the problem. Product creates a page for SEO. Marketing creates a page for the launch that is more branded. Not a good idea. The buzz the marketing team can create with that landing page will help with SEO goals because it can drive links that help Google trust the page more to rank it higher. Instead, product and marketing must work together to carefully balance positioning to maximize what helps the page rank, what gets potential customers interested, and what drives loyalty over time. This is what the best brands like Apple and Nike do.

Product Positioning Is A Delicate Dance

Many times when we talk about product marketing, we talk about the launch. But positioning is where the real long-term value is for features and new products. Dev and marketing teams have a lot of different variables to balance in launching new products and features, and positioning is at the heart of many of them and the hardest to get right. In almost all cases, we will need to iterate to optimize comprehension, adoption, retention, satisfaction, and that emotional connection that leads to word of mouth and improved adoption of things teams will launch in the future.

Thanks to Tamara Mendelsohn for contributing to this essay.

Currently listening to my Vocal Tones playlist on Spotify.

Fire Every Bullet

In crisis situations, a new style or management and prioritization has to occur. Andy Grove famously called this “wartime”, and he and others like Ben Horowitz have described what it’s like to be a “wartime” CEO. I haven’t ever seen anything written about being a wartime CPO though. Being a wartime CPO means a lot has to change in how you approach building product. Most product leaders think about their team as the product, and they continue to iterate on their team through hiring, training, coaching, delegation, etc. In wartime, you’re not hiring, you don’t have time to train or coach, and you make more top down decisions. But there’s one big thing that needs to change for wartime CPOs I want to cover today, and that is prioritization and evaluation.

I hope you never have to be a wartime product leader. But as you might have surmised, Eventbrite has been in a wartime situation for over a year now. Let me give you some background. In February 2020, Eventbrite started to become aware of a big problem. While the company was off to a fantastic start to the year, we could see the tidal wave of a global pandemic coming. Neither the world, nor us, was ready for what our metrics were showing could happen: the global shutdown of the live events industry. We were about to go to war, but not against a competitor, instead against nature.

There were, of course, differing opinions about the severity of the situation. The media was making fun of VCs for banning handshakes and telling us to be more worried about the seasonal flu, but the media failed to take into account the true potential downside. When the downside is unknown and potentially disastrous, as Nassim Taleb would say, the only rational reaction is over-reaction.

We planned for our mission, to bring the world together through live events, to be tested like never before. We acted swiftly to ensure the longevity of our business and mission, and the wellbeing of our employees, creators and investors. We launched resources and tools, we increased communication to keep employees informed, engaged and connected, and we realigned cost structure and secured access to funding. We also re-wrote the strategy of the business to align to this new reality.

More specifically, on the product side, we shifted all of our focus to help our creators prepare for the reality of a global pandemic and what that meant for their businesses. As we got to work, I recalled a conversation I had with Luc Levesque years ago when we brought him on as an advisor to Pinterest. Luc was the VP of SEO at Tripadvisor at the time (now VP Growth at Shopify), which was the only American company I could find that had succeeded at international SEO. Pinterest’s biggest impediment to growth was international growth, and SEO had been our primary lever to get U.S. growth into good shape after our initial strategy of leveraging the Facebook Open Graph stopped working. I was asking Luc whether we should prioritize different tactics to make international SEO work like international link building, localizing our URL structure, or making sure only content in local languages showed up on a page. His response was basically, “Dude, you do ALL of it.” We could figure out which one mattered the most after we’re successful. This is the approach we took at Eventbrite when the pandemic went into effect.

We built every possible thing we could to help creators and the company. We helped creators pivot online through virtual events; we published information on how to apply for loans; we built a bulk refunds tool, introduced the ability for creators to pay-in or wire money to Eventbrite to refund consumers and a credits system, and an easy postponement tool. We fired every bullet we had at the pandemic problem. We did not prioritize. It didn’t matter how much effort each activity was. We were going to do it all, and do it fast. We released things that would not meet our normal quality bar, because the only thing better than releasing these features for creators today would have been releasing them yesterday. We later learned other companies were doing the same.

One thing I would say, maybe feeling somewhat self-conscious right now, we made a company wide decision to lower our minimum acceptable quality bar due to the pandemic. If you observe Shopify right now, we are launching a lot. Almost just because of this one change. So we are pulling a lot of our roadmap forward in time. Everything that can help businesses right now, just because, again, we are in a crazy world right now.
Tobi Lutke, CEO of Shopify, on Invest Like The Best (May 2020)

You never want to be on the other side of a catastrophic event having failed saying “we could have done more,” and that has been top-of-mind for us throughout the pandemic. What is interesting when you take the approach of doing everything is some of the tactics work really well, and some do not. There is a tendency to evaluate those tactics in isolation for their success and failure. This is a mistake. You have to evaluate success or failure via the aggregate of all the bullets you fired. Did we save the company? We did. Did we save a lot of our creators’ businesses? We did. You can’t do an experiment or results review on those tactics individually. You have to look at the portfolio.

When should you fire every bullet? Do you fire all the bullets only in near death situations? How about live events recovery? Is Eventbrite firing every bullet to maximize the success of that? Prospect theory states that humans dislike downside impact more than they like upside impact of the same level. Many people have called this irrational. In fact, it is not, because extreme downside effects are things like death and ruin. Extreme upside effects don’t have the same degree of effect. So, firing every bullet makes a lot more sense for extreme downside scenarios than extreme upside scenarios. Think of the two by two.

The difference between we could have grown a little faster and death vs. safety is not at all the same. That doesn’t mean firing every bullet in upside situations is wrong; it’s just not as clear of an answer as in the extreme downside scenario. Quibi did everything to grow for its launch and burned through $100 million. It might have been better to do a smaller launch and iterate on content to find stronger product/market fit. Uber burned through billions for many years to try to both accelerate the size of their market and their market share within it, and it’s almost a $100 billion company.

The important thing to remember here is in extreme circumstances a lot of the best practices are different. Decisiveness, waste, and measurement will trade off in very different ways. It’s important to register when in these extreme situations that a different rulebook may be required to do the right thing for your business or product when in normal operations. Wartime isn’t over at Eventbrite, but I like to think of the situation right now as we’re finally having peace talks. 

Currently listening to Primitive Arts by Ron Trent.

Transparent Optimism

When I started managing teams at Grubhub over a decade ago, I was pretty obsessed with high performance. I wanted my team to have very clear goals, remove any roadblocks they would face to being successful, and make a big impact on the success of the company. I was able to hire a strong team, and we got to work, 100xing the size of our customer base over four years. As part of this process, a lot of what I tried to do was reduce distractions for the team. Any time there was strategic misalignment or confusion at the top ranks of the company, I would hide that from the team so it didn’t affect their performance. In other words, I wouldn’t let confusion at the top level create confusion at their level.

As the team grew over time both in size and in scope, I started to see cracks in this strategy I didn’t immediately understand. The first symptom was people on my team saying that while they felt very supported by me and were growing in their skills and their career, they didn’t have much visibility in what other members of the team did or how their roles worked. So, I created a Friday meeting we called “Team Learn” where every week, one team member would deep dive on what they were working on so the rest of the team could learn more about it. Initially, these were topics like email marketing or Google Adwords, but we started expanding them to other topics the team wanted to learn about, like venture capital and emerging channels. This meeting was so successful other teams wanted to participate, so I eventually expanded the meeting to include other teams.

This didn’t solve the root problem though. As my team got more comfort or clarity in their feedback, I started to understand the root problem more. While I was shielding my team from any swirl related to top level strategic decisions or screw ups or whatever elsewhere in the company, I was not the only person they talked to at Grubhub. So, they would hear from peers about all of these other things going on I had deemed to be unimportant or distractions, and the fact that I didn’t ever mention them made it feel like I was hiding things from them. It made them feel as if they couldn’t handle that level of knowledge and weren’t being treated as senior as they should be. 

So I shifted my approach. I made a commitment to share what was going on, but also contextualize it so as not to create doubt or swirl in their minds about what was going on at the company. We were definitely winning, after all. I moved from extreme editorial filtering to complete transparency, followed by contextualizing how this will all work out and why we win. When we hire great employees, the push to focus them and not distract them, while good, can easily be used as an excuse to not share hard things, and that creates a belief that the team can’t handle unresolved conflict, work through confusion, or understand strategic fog or even help lift it, and creates the perception that you as a leader are hiding things. It’s like hiring a bunch of strong engineers, and then only feeding them tickets of what they need to code through Jira because if we actually got them involved in deciding the problem, “they couldn’t possibly understand the business!” It doesn’t make a lot of sense when you think about it.

At Eventbrite, I have come to call this style transparent optimism. I’m going to give you all the context, the good, the bad, and the ugly, and explain how I think we come out on top. I trust my team with being able to handle all of that context and ultimately help us work through some of the thornier issues together. This is a style of communication that will not work with all cultures. Company cultures have to decide where they exist on a spectrum of open vs. closed in their communication. If I tried to apply this style at Apple, for example, I would quickly be fired for sharing things they do not want shared. So I bias toward cultures that have a comfort with this level of transparency, which is not all companies! Many companies would not even let me write a blog like this while working there. At Eventbrite now, I host quarterly AMAs with the team, the CEO does them twice a month, and both the CTO and I wrote monthly internal blog posts on what is on our mind. 

Obviously, I am biased, and communication styles come with pros and cons. With transparent optimism, I create risks of more interpretations of what is happening, external leaks, and it just requires me to communicate a lot more. But ultimately, I think it creates a default trust and default respect with the team, and helps them contribute more to the success of the company.

Currently listening to Scurlage by µ-Ziq.

The Rise of Department Operations Roles, and How to Tackle Inefficiency

At every company, there are well defined roles you would expect to see. In software, they tend to be roles like engineering, product management, design, marketing, legal, finance, etc. But as companies scale, they tend to invest in more specialized roles over time. During that transition, operating in one of these roles can be confusing. One interesting trend emerging at many companies including Eventbrite is the creation of departmental operations roles. Oh, you’ve seen them: Marketing Operations, Sales Operations, Design Operations, Product Operations et al. My first instinct when I hear an “operations” title is “inefficiency.” Not that the operations person is inefficient, but that there is inefficiency at the company. It is okay to be inefficient at things at your company. At various times, it will make sense to be inefficient in tons of areas of the company. The danger is in accepting inefficiency for the long term. We should strive to eliminate inefficiency over time at companies, not embrace it. Thus, the goal of departmental operations teams can be somewhat paradoxical. By explicitly attempting to remove inefficiency, they are actually attempting to remove the need for their roles entirely. 

The Intercom Biz Ops team was the first to just come out and say it. This can create a remarkable conflict of interest though. By doing a good job, will I eliminate the need for my job? As a result of this conflict of interest, we have started to see people in these roles try to define them as long-term necessities in organization, which means employees are optimizing for themselves instead of the company. What is interesting about this trend is that this job security issue shouldn’t be a conflict of interest. The goal of every job inside an organization should be to eliminate the need for it so you can do more important things. This is a great way to get more responsibility and promotions. There would be no greater pride for me than feeling like I am no longer needed in my current role at Eventbrite, for example.

So, if you want to do a great job in a departmental operations role, how do you do that? Well, the real question is how do we solve inefficiencies at companies? It’s like solving any problem within your company. You use various tools. I have a very specific hierarchy I like to follow to solve these problems, and I wish more companies used it instead of defaulting to hiring people and creating roles. If you’re in a department operations role, you can consider this a playbook to helping the company be more successful.

#1 Software
Any problem or inefficiency we can solve with software is superior to other forms because it automates away the inefficiency in the future once it is built. Now, it may be the case that we cannot think of or do not have the resources to develop a software solution to the problem, permanently or temporarily, or that there is no software we can buy that helps. This is okay, even normal. Companies tend to under-invest in leveraging engineering to build solutions that help their companies become more efficient, largely because so many companies are engineering-constrained. But just like engineers have started to work more on business problems like growth or marketing, they will eventually start to work more on internal tooling that enables their and other teams.

#2 Process
My next goal would be to solve the problem or inefficiency with process. Process innovation is a remarkable thing. By understanding the issue and proposing a way of operating to solve the problem, the pain point can frequently be mitigated or disappear. Now, this is not as automatic as software because it requires people doing things to follow the process and usually more training than software. But processes can become hard-to-break habits, especially once employees see the benefits of them inside an organization. This is more of where departmental operations roles tend to thrive today. By understanding the strategy of the business and the day-to-day operations, operations team members can spot inefficiencies, test different process solutions and assume responsibility for scaling out ones that work. But these solutions can be led by anyone. The more this happens without dedicated operations people, the more efficient an organization is.

#3 People
My next best option after process is to solve a problem with a person. Hiring is expensive, so it should be considered carefully. I definitely prefer hiring for concrete roles that have well defined value inside companies. Engineer, designer, analyst, etc. If you need to hire an Operations role because the problem is nebulous, temporary, or today can’t fit into one of those roles, you can do it. But you should have a career plan for those roles to evolve into a more well-defined role. Fortunately, team members that showcase generic problem solving skills are great fits for many other types of roles inside companies, so they rarely have to worry about their next internal career move. Still, it may be more efficient to actually look at one of the other solutions below.

#4 Advisors or Consultants
Sometimes the right person isn’t available, or the problem is well time-boxed. In this situation, I prefer to find consultants or advisors. Subject matter expertise exists out there in the world for almost anything. Working with individuals that have specific experience makes it easy to align incentives even if this subject matter expertise isn’t hireable full-time. If the issue is temporary, you may not want to hire full-time anyway.

#5 Agencies and Firms
Lastly, I look at agencies or firms. With these companies, it is hard to prevent misaligned incentives. But they do have expertise and bodies that you can throw at a problem with less risk of being stuck with them full-time. 

Where Operations Wins
I am not against Operations roles; I just want companies to understand how to use them well and to scale out of them whenever possible. Early stage companies can absolutely crush with Operations. Smart people Swiss Army Knifing problems is many times the fastest way to scale in the early stage. Operations roles can also thrive in larger companies, if they root out inefficiency with the tools above and don’t succumb to empire building. We can’t yet automate transportation needed for the delivery of the business? Call that the Operations team. We can’t automate training for our customers yet? Call that the Operations team. 

The COO role is very common, though its definition is ambiguous because it tends to be a grab bag of executive inefficiency. Usually, the COO manages what the CEO is inefficient at. That can be management in general, or parts of the company the CEO is less capable of adding value to. The COO role can also be a roll up of certain executive functions when the CEO has too many direct reports as well. 

This is all fine and even optimal. But every operations role you add you should also add to a list of inefficiencies you hope your company can solve one day, and always be thinking towards software or processes that make these current roles unnecessary so those people can take on even more important roles over time.

Currently listening to Good Times by Moire.

Reducing Product Risk and Removing the MVP Mindset

I originally wrote this piece internally at Eventbrite and thought it might be valuable to folks who do not work at Eventbrite as well. Slightly edited to remove Eventbrite jargon.

What is the right way to build products? Earlier in my career, I would have told you everything should be AB tested, and that you should build only as little as you need to validate a hypothesis. Every problem should have user research involved at the beginning, aligned on the problem instead of just validating or invalidating solutions. Every key result should be outcome based. Every engineer, designer and product manager on the team should be involved in defining the problem and the solution. These are all good ideas. However, once you add enough of these “best practices” up, it reads kind of like those articles talking about the morning habits of the most successful people in the world. If you actually try to follow all of those habits, it would take you six hours a day and cost a lot of money. I was once reading an article about what a futurist at Google eats for breakfast every morning to live longer. The article added up that his diet of food and pills cost him $1 million per year. My morning ain’t that long, and I ain’t got that much money.

So if the documented “best practices” take too long or are too expensive, how do you approach different product situations? I want to share a few frameworks that I think can help, but there is no substitute for judgment here. Eventbrite has lots of different product problems. One of the things we are trying to get better at is defining the type of product problem we are working on,  and outlining how we build based on who we are building for, whether it’s consumers or the many different types of event creators we support.

RULE #1 OF PRODUCT WORK: IT IS NEVER DONE

We should all know that products and features need to continually improve to stay relevant for our users over time. And it should come as no surprise that no product or feature is perfect on initial release. They need to be refined over time to get better, incorporating feedback from actual users. Many companies just launch new features and forget they exist, rarely improving them. This is not how great products are built. What this means though is that initial releases will never have everything teams want. But if you continue to iterate, this is not a problem. As long as we’re getting value to users as they become available.

If you’re going to continue to iterate on features, supporting them takes effort to maintain and improve over time. The much bigger question then becomes whether product work should be started, and when progress should be shared with users over time. If you start the work, you’re implicitly saying the company should expect to support it for years. That’s a big commitment. So, at Eventbrite we try to do work to de-risk that commitment up front. And if you have a long amount of work mapped out, figuring out what chunks can be released independently so that incrementally more value is being experienced by users is tricky. I’ll dive into how at Eventbrite we are trying to improve our approach to reduce risk and ship releases incrementally.  

A FRAMEWORK FOR REDUCING RISK IN WHAT WE BUILD

Product development projects always have very high opportunity cost. So, no matter who we are building for, we try to de-risk investments into projects by learning more about the problems before we invest time in solutions. How do you de-risk projects? An obvious answer may be to talk to customers, right? But it’s not that simple. Users of products are generally unreliable narrators of their own behaviors and preferences. How unreliable depends on who the customer is. For our consumer products, asking our consumers what they want is usually a lost cause. Sure, we can and should regularly talk to them about their problems, but we have to infer solutions ourselves. We can’t expect our consumers to be excellent product thinkers. If we did build what they asked for, they probably wouldn’t end up using it. As Henry Ford allegedly said, “If I’d asked customers what they wanted, they would have said a faster horse.” 

For event creators, it depends on how sophisticated they are. Eventbrite is a broad, horizontal platform used for many different types of events, from small meetups to large festivals and conferences and everything in between. For our most sophisticated customers (and most enterprise businesses), it’s not a bad approach to ask customers what they want, ask them to prioritize how bad they want it, and build and charge for things in that order. For less sophisticated customers, it’s still likely a bad idea. This ends up creating two spectrums to help you understand what to do by level of sophistication of the user vs. how much data users generate. Each of these quadrants tends to have a different approach to de-risking projects.

So what this implies is that our approach to de-risking projects should be very different depending on the type of customer we’re building for. Eventbrite isn’t Instagram, but we do have a lot of consumers compared to most companies. So, attendee experience projects are going to bias toward a data-first approach with research to back up the why when needed. They will also be the most likely to AB test. The self-service creator side of our business is more towards the middle of these axes. So we’ll blend some data and some research needed in addition to direct or proxy customer feedback. We also have segments of frequent creators that are smaller in number, but more sophisticated than the average self-service creator, so direct feedback plays more of a role in what we build, but it also has to be supported by data and user research. When we expanded our sales team into enterprise segments in the past, we were much more likely to build what they asked for.

A FRAMEWORK FOR DIFFERENT PRODUCT APPROACHES WITH DIFFERENT LEVELS OF AMBIGUITY

Cody Evol, a Director of Product Design at Eventbrite, helped develop one of our more useful frameworks to help us understand how much time we devote to a project. When I joined Eventbrite almost two years ago, every team was describing their project as an MVP, which is quite strange, as the Minimum Viable Product framework was built for launching new products, which is not what most teams were doing.

Product teams using inappropriate frameworks off the internet to justify their approach? Inconceivable!

The key thesis of Cody’s design quality framework is that the level of investment before something reaches a customer is tied to how confident we are that we understand both the problem and viability of the solution.

Your development approach should change based on how ambiguous the problem and ideal solution are.

When there is a lot of ambiguity about the problem or the solution, we should generally try to de-risk the project before investing a lot of time into it by using the approaches above. And we have many tools at our disposal to do this. With enough validation, teams should invest in building minimum viable products or features. Minimum viable product is probably the best known product development framework outside of perhaps Agile. It is about delivering value to users by building the smallest product you can to test your hypothesis. You ship to learn, which influences future product development. However, most things we build aren’t minimum viable products. It’s a product development framework for brand new products, and we rarely build brand new products. More likely, we are building features. These can be even more lightweight because you are building something on top of an existing product (you can think of a product as a bundle of features). The “Follow This Creator” feature was a great example of a minimum viable feature on the consumer side of our product. We didn’t know if consumers would adopt it, so we launched it just on Android without even building the push notification functionality. As we saw consumers adopt it, we built it for iOS and web and with email and push functionality.

The goal is usually to reduce the ambiguity around the product problem and solution so that you are not building an MVP/MVF, but instead doing phased delivery. This is a type of development where you have a strong vision and the problem and solution are validated, so the goal is to build toward that desired vision, and release incrementally as valuable pieces of that vision are complete.

MVP’s and MVF’s are to prove that our ideas actually solve a problem. If we prove that, we typically need to invest a lot more to reach the potential of the product or feature idea. Rarely do MVP’s or MVF’s crush expectations out the gate.

OUR APPROACH MOVING FORWARD

When projects are de-risked, we start building the desired product directly in phases. No shortcuts on design quality. No accumulation of technical debt to “get something out”. These are features we intend to be very valuable and support for a long time, so they should be built the right way. But how do you break up the product vision into phases when you have such a clear vision of the whole you want to build? Shouldn’t you just build it all upfront? There are a few reasons this is a bad idea. One is that if you wait to deliver some value to customers until all of the value you envisioned is completed, customers are dealing with sub-par experiences that do not improve for a long time. It is better to deliver some improvement over time than no improvement for a long time, and then a big reveal. Otherwise, you are holding back things that could add value to them today unnecessarily. Secondly, even with strong visions backed by data, usage of products can surprise you. It’s better to get the learning from usage incrementally over time to make micro-adjustments to the vision. Getting no feedback from customers on what you’re building for a long time is dangerous as customer preferences evolve. Lastly, releasing regularly allows you to de-risk your vision technically as well. You get to see how what you’ve built scales or breaks incrementally instead of all at once.

What if there is no way to break up the value delivered to the customer in phases, meaning it’s literally not valuable until all of the work is complete? It is generally still a good idea to release the code incrementally to de-risk the technical aspects of the project even if the customer doesn’t see it. One of my favorite recent examples of this is Apple. Hardware is usually very expensive to iterate on compared to software. Apple was working on a multi-year effort to launch Apple Pay using a customer’s fingerprint as the verification. Instead of launching a new way to authenticate and the credit card payment at the same time, it launched TouchID on the iPhone 5S to see if fingerprint authentication would be a successful interaction. That de-risked the launch of Apple Pay on the iPhone 6 using fingerprint for payment.

To bring it all home, product development is hard. You can’t read one article on the internet and all of sudden build great products, just like you can’t talk to one customer and know exactly what to build. We create frameworks not so that we can shut our brains off and follow an exact guide to building our product, but so that we can focus our brain power on the thousands of other very confusing and ambiguous questions we will undoubtedly face in trying to build this product over time. I hope these frameworks can help you understand how Eventbrite approaches situations it comes across, and gives you some things to think about as you build products.

Thanks to Cody Evol for his help on these frameworks.

Currently listening to Pool by Skee Mask.

Why Product Leaders Fail

I’ve yet to meet a fellow Chief Product Officer or Head of Product say, “yeah, I’m crushing it right now.” In my conversations with fellow product leaders, there’s even a meme that’s started to form around product leadership roles. Effectively:

“Yeah, you just try to put some points on the board before you inevitably get fired.”

So, if a typical CPO feels their role is about trying to survive a couple of years i.e. long enough to help the business a little bit, what is causing that? Why is it so hard to endure as a product leader?

I would say there are three common failure modes depending on how far along the company is. The earlier stage of a company it is, the more likely the answer is going to be misalignment with the founder/CEO. What no one tells product leaders when they accept product leadership roles is that nine times out ten the founder and CEO still wants to drive the product vision. They want you to help execute that vision. And as founders scale, their founder intuition ebbs in effectiveness in comparison to product expertise in-house, but it takes a long time for founders to accept that. That transition period can be very rocky.

For later stage companies, the more likely answer is that the CPO is really only good at one type of product work, and the type of product work needed for the business changes over time. This can manifest in two ways: The product leader has skills that don’t match the type of job needed today, or as they execute, the skills needed change, and the leader cannot adapt. Not only is the product leader not good at that new job, they are also less likely to be interested in it.

Let’s talk about each of these failure modes and what both product leaders and CEOs can do to make them less likely to happen.

Failure Mode #1: Who Owns Product Vision?

Founders tend to have insanely good intuition about their customers and products because, let’s face it, no one has spent near as much time thinking about them and their problems. When startups tend to hire product leadership, it’s their first time hiring this type of leader. Interview processes can be clumsy or unoptimized, with the founder still figuring out how to articulate the real need. Commonly, what happens during this process is both the founder and prospective product leader end up jamming together on the future product vision. Both sides love this engagement, but for the founder, it’s not an effective test on how much the prospective product leader will help the founder, and for the product leader, it can give a false impression that they will have a ton of say in the product vision.

If at all possible, founders should leverage outside expertise to structure the recruiting and interview process for this type of role. One of the key questions to get explicit on before the process begins is what role will this leader play in setting the product vision? For non-product/eng/design founders, they may be asked to define it. For founders with product, eng, or design backgrounds, that is typically not the case until the company becomes much larger. Product executives usually play a consulting or execution role in a vision that is founder led. Founders need to tell candidates which one it is, and candidates need to ask. Neither of these happen as often as they should. 

Once founders understand their answer to this question, they need to vet for the appropriate skills. If what you really need is help executing on the vision, don’t spend much of the interview process jamming on the vision. Sure, candidates need to understand the vision, but what you really need to learn is are they comfortable receiving a vision from you and bringing it to life in the myriad ways that are difficult. 

Failure Mode #2: Does the Expertise Match the Type of Product Work Needed?

Different companies require very different approaches to their product strategy to be successful over time. Most of us understand there are different types of product work. There is tech and process scaling, there is building new products to find new product/market fit, there’s building new features and iterating on the user experience to strengthen current product/market fit, and there is growth work to get the maximum number of users to experience the product/market fit that exists. Traditionally, product leaders lean toward being experts in one or another. For example, I am definitely most known for my expertise in growth.

Founders often lack the understanding of what type of product challenge they are actually facing when they attempt to hire a product leader. Network effects businesses tend to focus more on growth because more users make the product stronger in a much more meaningful way than new features. DTC ecommerce companies / brands are always launching new products. SaaS businesses tend to need to launch lots of new features over time. Hiring a product leader that wants to build new features all the time into a network effects business likely isn’t going to work that well.

Failure Mode #3: Can the Product Leader Adapt as Needs Change?
Even if founders hire the leader with the right skills at the right time, as companies scale, how much weight they put on these will need to change over time. Today, the product leader’s job is to be what the business needs them to be. So while the old school product leader is a specialist, the new school product leader needs to be a chameleon, who can balance a portfolio across scaling, new product work, feature work, and growth weighted toward the needs of the business, and re-weight it considerably over time as business needs change rather than leave once business needs change. That’s hard, but inevitably how product leaders have to evolve to be successful over the long term within a company.

As a growth oriented leader, I am actually spending more of my time at Eventbrite on scaling, features, and new product expansion work, because that is what the business needs right now.

Product leadership is incredibly hard. Both founders and product leaders can eliminate some of what makes it so difficult by aligning on expectations before hiring roles, and on aligning which problems the organization is focused on right now. It is then up to product leaders to be able to evolve as the product needs change over time. They are both the best equipped to understand when needs change and help the organization change with them.

Currently listening to Rare, Forever by Leon Vynehall.

Career Paths, Personal Missions, and Concentric Circles of Impact

Often, people ask me for career advice or how I got to where I am, or more tactically if they should advise companies, invest in companies, start a company or become an executive or whatever. My first instinct is to say, “Why would you ask me? You certainly don’t want to follow any of the steps I took!” To try to make my advice more actionable than that, I thought I’d document some of the key decisions I went through to make a signal out of my career noise.

My career choices have been somewhat unconventional from the outside. I graduated summa cum laude in undergrad to just take an internship at Apartments.com. I joined a 15 person startup to start a marketing team at 25. To say I was unprepared is an understatement. After building up a team and growing Grubhub over five and a half years into a public company, I took an IC role at Pinterest, instead of many executive offers. After three years there, where we tripled the user base and unlocked international, I then decided to… hang out at a venture capital firm. Then started an advising business. Now, I’m a Chief Product Officer at Eventbrite, a public company.

No one would draw up a career path this way, but I focused on learning potential at pretty much the cost of anything else, and it’s served me well. What a lot of young people don’t understand is that if you bet on increasing your learning potential, your earning potential compounds over time. The money will be there if you gather differentiated skills the market values (my knowledge of obscure electronic music, for some reason, is not one of those skills the market values).

This advice is fairly easy applicable and, I think, well understood by a lot of people. If you are making a choice between learning and earning, the former will almost always make sense not only from a happiness perspective, but also from a financial perspective long-term. I want to talk about what happens after you self-actualize in this direction.

Let’s say you’ve spent a decade plus collecting valuable skills, applying them in interesting ways, and you are differentiated on the market. Problem solved, right? You’ll never have to worry about a job. You’ll have all these opportunities. Well, not really. They say in startups the problems never get easier; they just change to different problems. I think optimizing your career is the same way. What people don’t tell you is if you optimize for learning, there are fewer and fewer jobs where you can mix all that you’ve learned together. And that you actually have to pick amongst many competitive opportunities. Not picking or not leveraging all your skills can leave you unfulfilled, like you’re not at peak potential, or lead to some of your skills atrophying from lack of use.

As someone who went through this issue after Pinterest, I did some deep reflection on what makes me feel fulfilled on a path to a personal mission. I’ll share that mission as perhaps a useful example, but yours will almost certainly be very different, or even optimize on different attributes like industry, problem type, relationships, etc. After reflecting on what I liked and didn’t like at all the different companies I worked for or with, I realized I really enjoy problem solving. Specifically, figuring out problems related to building businesses and ensuring those solutions can be shared with others. Now, those solutions aren’t growth hacks or tips and tricks, but generalizable frameworks that can be wielded in the appropriate situations. I eventually landed on a personal mission of discovering and scaling the best practices of building companies.

What I found from my advising work is that the best practices of building companies are very unevenly distributed. And it isn’t that one company has all of them and isn’t sharing. It’s that companies are good at different things, and there isn’t even cross-pollination of these best practices so that every company gets better at operating. In fact, I’d say most companies in Silicon Valley in aggregate operate poorly. It’s a weird paradox that the best performing companies are some of the most poorly run, because they can be. As Rick James might say, product/market fit is a hell of a drug.

Like finding product/market fit for a company implies a product people value and a way to make money at it and scalably distribute it, the next question comes in how to deploy this personal mission. I played around with almost every model: full-time employment, advising a handful of companies in-depth, investing and helping the companies I invest in, creating courses with Reforge that anyone can take, and blogging for anyone who wants to read. There is an implied breadth and depth of impact and learning from this model. Focusing all your time on one company has the most impact on how it operates, but that scales the least of any model. Blogging reaches the most amount of people in aggregate, but with no customized learning.

What I have found interesting about my personal mission is that while there are clear trade-offs, there are also win-wins. The blog creates advising opportunities. Operating full-time at one company makes me a better advisor, course creator, and blogger by the depth of problems I get to work on. Advising allows me to see fresh perspectives that broaden my problem solving at my current company. I have not found a perfect formula to optimize the ratio of time spent between these different avenues to deploy against my mission, but what I did learn is that it is likely best to vacillate between the different circles, which is part of the reason why I am not a full-time advisor like I was in the past. This is basically a form of optimizing for different steps in my learning loops to continue to unconstrain my personal growth, much in the same way I optimize for unconstraining growth in the companies I work with.

Finding a personal mission and thinking about how to deploy against it is something I would recommend more people spend time exploring for themselves. I think it helps optimize for personal happiness and growth in an environment where there are seemingly competing opportunities all the time that are hard to judge against each other.