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It’s hard to believe that five years have already gone by since RevenueCat’s inception. In a matter of weeks, RevenueCat will become the company where I have worked the longest in my career. As Jason Lemkin says, it’s important to continuously reinvent the company and oneself every five years. It’s required to carry on and stay relevant the following five. I had no doubts my role was going to evolve again. It has every single year, leading me to start this series of posts. But the remarkable part this year has been the internal transformation of RevenueCat. As we enter 2023, the company is more mature than ever before, with well-established processes, cross-functional teams, and leaders in key areas. The company has become a well-oiled machine, allowing us to deliver quality software at a faster pace. However, reaching this point was not without its challenges and it took a lot of hard work to get here. Expectations vs reality Last year, I had high hopes for revamping our onboarding,...
over a year ago

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More from Miguel Carranza

My role as a founder CTO: Year Seven

2024 has come and gone, and it’s time for my annual post. What a year for startups—like squeezing five regular years into one. Do you remember the Apple Vision Pro, the DMA regulation, founder mode, or the o1 launch? All of that happened in just the last twelve months. It’s also been wild at RevenueCat. My journal is full of stories that could fill a whole book or even a few HBO Silicon Valley seasons. Some are inspiring, some are hilarious, and others are honestly gnarly. Due to limited space, the need for context, and respecting everyone’s privacy, I’ll cover only the most interesting topics at a high level. Looking back, it was a good year for RevenueCat. Actually, a great one. Perhaps our best since 2020. We have plenty to celebrate: We accelerated again, and we hit our C10 revenue plan. We made our first acquisition and welcomed an amazing founder to the team. We signed our first multi-million-dollar contracts. We went to more than 20 events around the world… …including hosting our own conference, featuring its own award ceremony. We became the #1 payments SDK on iOS. Our swag went to 11. We launched over 80 user-facing features. We showed up in Times Square and along Highway 101. We raised a mini Series C and welcomed two new board members. We landed in Japan for the first time. Our API grew beyond 2B requests per day. We are processing nearly twice the TAM we had when we started the company. OpenAI is a friend of the cat. We continued building a winning team. We hired people who were on my to work with bucket list even before we started the company. By all the metrics, 2024 was our year of shipping and selling. We absolutely helped developers make more money. My role If you compare our progress to the goals I wrote about in last year’s blog post, it’s clear we succeeded. But the journey itself was a lot rockier than I had imagined. Many things didn’t go as planned, somes hires did not work out, and some strategy changes were really hard to push through. At the start of the year, besides my usual responsibilities, I also set four personal goals to help me scale with the company. I wanted to: Ship code more consistently. Talk to at least one customer every single day. Get more involved in areas outside of engineering. Stay very close to my co-founder Jacob, giving him my full support. I completely missed goal #1. Honestly, that hurts because I love building software. But I’m not too upset about it—our customers care that the team ships, not that I personally do. And in a way, I did help the team ship. As for the other three goals, I hit them, at least based on the company’s results. Still, my self-perception wasn’t always great. I found myself acting much more like a co-founder/executive than a CTO. Some weeks were brutal, with constant context switching across tasks and teams I didn’t always enjoy. At one point, there were over 60 people in my org, spread all around the world, which is pretty intense for an introverted computer kid. A lot of bullshit escalates to the top, making me question my entire existence some days. And then life threw serious personal emergencies at some of our team members too. Like I said last year, life is what happens when you’re busy building your startup. As we got closer to 100 people, it was statistically unavoidable that we’d face a few life-changing traumas—sometimes several all at once. As a founder, you need to be supportive and empathetic, but also protect your mental health. As a human, it’s tough. Add in a couple of two-year-olds who were often sick and not sleeping, and it felt like a ticking bomb. Did I burn out for the first time in my life? I don’t think so, but it got close. I’m confident being a founder (and having a co-founder) kept me going. I care too much and must stay resilient. If I’d been just an employee, I might have tapped out. But enough about the tough parts. Aside from being a professional BS handler, here’s how I spent most of my time: Lots of travel This was the year I traveled the most in my life—and looking back, I probably should have traveled even more. I visited customers, helped with sales, conducted executive interviews, and spoke at a few conferences. It’s hard being away from two little kids, but each trip turned out to be worth it. Support One of my biggest worries this year was our support function. Everything was fine, but our Support Engineering Manager was going on parental leave, and the bus factor was scary. I’ve seen support crises before—they’re not fun. It wouldn’t have killed the company, but at our size, it might have forced us to pull senior engineers into support and slow down our product velocity. Time was short, so we tried a few things that worked: We hired two new Developer Support Engineers who already knew our product—former customers! Their onboarding was smooth, and they hit the ground running. We split the support team into two pods with their own leads. Each pod handles certain tickets, and they collaborate with each other instead of relying too heavily on one person. We finally set up our first on-call rotation for emergencies. Sales and post-sales Reviewing sales and implementation calls, giving technical input, collecting enterprise customer feedback for product and engineering, joining calls, and even doing some in-person visits. Writing more As our team continues to grow across the globe, not everyone has the same direct interaction with me or Jacob as before. A lot of our culture and collaboration style was once passed through observation, but now needs to be written down to reach everyone faster. These days, my code editor is basically replaced by Google Docs. I’ve been publishing more internal and external documents—like our Engineering Strategy and an updated How to Work with Miguel. Product delivery We still have a few details to refine, but our founder Shipping and Timeline reviews have been valuable. It gives Jacob and me a high-level view of everything in progress, lets us offer feedback, and helps us dig deeper where needed. It’s a great way to see each team’s capacity, find bottlenecks, keep a sense of urgency, and deflate anything that’s not truly important for the customers. Re-orgs This year brought a couple of big reorgs in product and engineering. Overall, they went well, but the puzzle gets more complex with each new piece. We created sub-teams to narrow their focus and keep things running smoothly. For the first time, we had a couple of management layers between me and our ICs. One major change was shutting down our Enterprise/Reactive team. The idea was solid at first, and they delivered plenty of value, but eventually they became the random tasks team. Our new plan is to reinforce the rest of the teams: quick enterprise requests go to the right team to handle them reactively, while bigger projects move to the main roadmap (which keeps us disciplined). The engineers from that old team will help bootstrap new teams as we hire in 2025. Hiring Our engineering hiring goals weren’t super ambitious, but we still reached them. The pace was a bit uneven, and some roles took longer to fill than desired. However, when Hiring Managers took ownership of the process (with recruiting as a support) it made a huge difference in the quality of our candidates. We also brought back the founder interview stage: Jacob or I spoke with every single candidate before making an offer, and we plan to keep doing this for the foreseeable future. Random founder stuff Not my main focus, but I still spent a fair amount of time handling people-related topics, operations, investor, customers and partners relations, fundraising, company policies, planning, etc. Learnings: deepened insights On culture Shipping is king. Yes, deadlines are stressful, but failing to ship and getting stuck in endless debates is far worse. It’s depressing. If someone isn’t a good culture fit, it will be more than a single incident. Over time, it becomes pretty clear to everyone. Top performers tend to measure themselves against the very best in the company. Reassure them they are doing a great job. On the other hand, those who underperform will look to other underperformers to gauge their own progress. Even top performers will struggle if they don’t fully align with the vision. Nothing beats talking to customers. Encourage everyone to do it. Better in person. Most managers don’t have a strong incentive to be strict, so finding the right balance takes a lot of calibration. Only once everyone is aligned, you can truly delegate. On hiring Managers hate hiring because it’s binary: a lot of “no”, but eventually one “yes” can change everything. Staying consistent really helps. Simple things, such as weekly updates keep everyone accountable. People management sucks. If someone’s main motivation is to be a manager for the title, or so they can “lead,” that’s a red flag for me. Best managers end up being those who never planned on becoming one in the first place. They actually roll up their sleeves and can do the work. Big ideas are great, but they need to be executed. This matters even more when it comes to executives. A truly great exec can change your life and it will feel like a brand new company. Given their influence, anything less than great will eventually turn into a big mess. Spend time with executive candidates in person. Watch how they work and make sure they’re real builders. Previous founders and true engineers are usually a little bit de-risked, but they’re still not guaranteed. I also like to write a very detailed onboarding doc, clarifying context, expectations, and what success or failure looks like. Having them write a 30/60/90-day plan helps us all align. I’ve learned not to rely on their past pedigree. The real key is their glass eating endurance. On company building Re-orgs are inevitable at a growing startup, and they will feel scary or emotional for people who aren’t used to them. I find it helpful to be super clear about why we’re doing it, and to share the fallback plan if things don’t work out. But I’ve learned that by the time you think you need a re-org, you’re already behind. We now plan to reassess our team structure twice a year for optimal shipping. A numeric goal (like an SLA or revenue target) is just a proxy. Missing it isn’t the end of the world if you learn in the process. But if you surpass it without recognizing what’s broken underneath, you’ll be masking critical issues. Perfectionists are great, but can have a tough time at startups. Some do fine if they’re focused on one specific thing or working as an IC. But as soon as they have to juggle multiple tasks, the chaos can feel overwhelming. Help them embrace it. Things will break. It’s about continuously reprioritizing, and stopping small cracks from becoming big fires. No agenda == no meeting. Synchronous time is expensive. The only exception is the occasional unscheduled call. After you reach around 50 people (especially in a remote setup), documenting every process change becomes crucial. I’ve learned the hard way that simply talking about a new process isn’t enough. Founders can’t talk to everyone all the time anymore, and misunderstandings or gossip can spread fast. Not everyone will read everything, but at least there’s a single source of truth to reference. Best people can stretch quite a bit—they’ll often rise to the challenge. But it’s wise to keep an eye on their limits before they burn out or become a bottleneck. On scaling as a founder A great EA is life-changing. Family will be supportive, but it’s not fair to offload all the stress on them. They will end up feeling helpless. Having a solid co-founder, a network of peers, or a good executive coach makes a world of difference. Founders are the ultimate guardians of the culture. It’s constant work, and it will feel relentless—especially when things are going well and it’s easy to get entitled. The best team members will help uphold the standard, but you cannot expect them to do all the policing. At this stage, it’s stupid not to level up your lifestyle in ways that reduce stress or save time. This might include childcare support, having a second car, investing in a better mattress, or hiring help with housekeeping. The startup is bigger than its founders, and the goal is to continuously remove yourself from the critical path. Still, it’s easy to forget that, as a founder, you literally brought everything into existence from thin air. Imposter syndrome often creeps in when you step outside your core expertise, but if your gut feeling is strong, it’s worth paying attention to. Stay open-minded, yet remember that no one knows the company quite like you do. The future Next year is going to be another big one. We’ll keep shipping and selling, while finally tackling our design and UX debt. We’ll keep investing heavily in our infrastructure. Not just for reliability, but also for real-time data. We want RevenueCat to feel fast, accurate, and easy to use. We’re also upgrading our self-serve and enterprise support, aiming for a truly world-class experience. In many ways, we’re finally seeing the original vision Jacob and I had back in 2017 come to life. We’ll be launching new product lines too, and if we execute well, we will be just a couple of years away from hitting $100M in revenue. We’ll keep building a winning team. We’ll hire about 45 people, 30 in Engineering, Product, and Design. It’s a challenge, but totally doable. As for me, my personal goals haven’t changed much, but my perspective has. Jacob and I used to joke that being happy and winning can’t happen at the same time. But why not? We’re in a privileged position to shape our own path and change anything we don’t like. After a lot of reflection and coaching, I realized I was simply too hard on myself. I was feeling depressed by the constant BS even though we were winning. A hack that helped was working with my EA to set weekly goals and then sending a public update to the full team. It let me see the real progress behind all the drama and back-to-back meetings and stay transparent with everyone. Next year, I’ll avoid meetings before 9 AM, keep an eye on calendar creep, and hold myself accountable to exercise and doing what helps me decompress. I know, it’s obvious. I also plan to travel more. Especially to the Bay Area, which is clearly back again. Meeting up with other founders and customers is always worthwhile. Another thing that made last year tough was having half my direct reports on parental leave for about half of the year. Now they’re back, and I can feel the momentum returning. Jacob has also taken over product again, now that he’s stepped away from directly owning operations and people. Increased shipping velocity has been noticeable. We have all the pieces in place. All that’s left is to keep pushing forward: shipping, selling and enjoying the ride. If there’s one thing I learned in Silicon Valley, it’s that no goal is too crazy if you refuse to give up. I really hope you enjoyed reading this post. As always, my intention was to share it with complete honesty and transparency, avoiding the hype that often surrounds startups. If you are facing similar challenges and want to connect and share experiences, please do not hesitate to reach out on Twitter or shoot me an email! Special thanks to my co-founder Jacob, my EA Susannah, the whole RevenueCat team, and our valuable customers. I also need to express my eternal gratitude to all the CTOs and leaders who have been kind enough to share their experiences over these years. Shoutout to Dani Lopez, Peter Silberman, Alex Plugaru, Kwindla Hultman Kramer, João Batalha, Karri Saarinen, Miguel Martinez Triviño, Javi Santana, Matias Woloski, Tobias Balling, Jason Warner, and Will Larson. Our investors and early believers Jason Lemkin, Anu Hariharan, Mark Fiorentino, Mark Goldberg, Andrew Maguire, Gustaf Alströmer, Sofia Dolfie, and Nico Wittenborn. I want to convey my deep gratitude to my amazing wife, Marina, who has been my unwavering source of inspiration and support from the very beginning, and for blessing us with our two precious daughters. I cannot close this post without thanking my mom, who made countless sacrifices to mold me into the person I am today. I promise you will look down on us with pride the day we ring the bell in New York. I love you dearly.

a month ago 43 votes
Full Circle

I’m back in Spain for my brother’s wedding. I rarely visit during the summer. The heat in my hometown is brutal, around 40 degrees Celsius (over 100 Fahrenheit for my imperial friends). Most people escape to the coast, just like my family did when I was a kid. I haven’t been here in years. As I drive along the coast, I find myself reflecting on a tweet about money and happiness, a vivid memory pulls me back in time. It’s August 22nd, 2007. The iPhone, the first real smartphone, has just been announced. It’s so cool, but of course I cannot afford it. It’s not even going to be released in Spain. I’ve just gotten my driver’s license, and I’m about to dive into my third year of Computer Science. I set up my clunky TomTom navigator knockoff, and hit the road. I’m on my way to meet Marina for our first real date. She’s cool, pretty, and kind. She likes the same music as I do, and even has distant relatives in California, the place we jokingly plan to visit someday (if I ever get enough cash). I’m listening to a pirated Blink-182’s self-titled CD. Pop-punk is pretty niche in the south of Spain, and it’s dying. Blink-182 has split up, and I missed my window to see my favorite band live. The Atlantic Ocean is as flat as a lake. This corner of Huelva’s coast is sheltered from any real waves, a stark contrast to the world-class surf breaks I drool over in magazines. And suddenly, reality hits: my childhood dreams of building a tech company in Silicon Valley, while vacationing in Southern California feel impossibly far. Even getting through my degree feels like a pipe dream. School isn’t fun anymore. It’s grueling, especially the parts I thought I’d enjoy, like algorithms and Data Structures. I might never become a Software Engineer. I feel stuck, trapped by my lack of direction. I am seriously considering quitting. But no degree means no job in the US, and good tech gigs are rare here in Spain. The only cool company is Tuenti, a new startup that is cloning Facebook. I’m nowhere near smart enough to land a job there though. Flash forward to today, 17 years later. It’s almost laughable to think about how hopeless things once seemed. Even now, it doesn’t feel like I’ve “made it.” The path and the results look nothing like what teenage me envisioned, but somehow, I’m realizing I’ve kind of checked off every box. I married Marina, and we live in Southern California with our two beautiful identical kids. We’ve become American citizens, and I’ve lived in the Golden State for nearly a third of my life. I’ve worked as a Software Engineer at a Silicon Valley startup, learned from the best, and found the best co-founder I could ask for. We launched our own company. Smartphones? They’re in everyone’s pockets now. Our product is in a third of all new apps shipped in the US. We’ve helped developers reach millionaire status, and we’ve made more money than I ever thought possible. But I’ve learned that a lot of money is a relative term. Somehow, I managed to hire insanely talented engineers—a bunch of them, ironically, from Tuenti. Blink-182 is back together, and I’ve been fortunate enough to see them live five times. I’ve even bumped into Tom Delonge after surfing world-class waves a few times. I’m literally just realizing how surreal all of this is. I tend to get caught up in the chaos of what’s next—the next big fire, the next goal—but sometimes you’ve got to stop, be present, and reflect on how far you’ve come. It wasn’t easy. It wasn’t without loss, sacrifice, and a fair share of doubts. Am I truly happy? Maybe not in a perfect, all-the-time kind of way. There are external things humans cannot control. But when I look at my life, I realize there’s no real reason not to be. The journey has been was worth it so far: the ups, the downs, the unexpected turns. So, here’s to your journey, whatever it looks like. Keep going, keep dreaming. It might not turn out the way you envisioned it, but it’s only impossible if you quit.

5 months ago 55 votes
From J1 visa to Blue Passport: A startup founder's immigration journey

I am drafting this post at 35,000 feet flying back from Japan. I’ve entered the US about 30 times, but this will be the first time I’ll be using my shiny blue passport. No anxiety about aggressive questions, secondary inspection, or the possibility of deportation. A couple of days ago, my wife had her naturalization ceremony, and with her, our whole family is now American. This post is a reflecting on our 11-year immigration journey. My American Dream My story with technology started at 8, with my first computer. I fell in love and decided that one day I would start a computer business. And of course, it would have to be in Silicon Valley, the epicenter of innovation. I grew up influenced by the iconic Californian lifestyle of the 90s, from Tony Hawk to bands like Blink-182 and The Offspring, which only fueled my desire to call the West Coast home. As I finished my Computer Science studies, the reality of achieving my American dream seemed increasingly distant. My enthusiasm for the Californian way of life hadn’t waned — I had started surfing and I was even playing in a pop-punk band. But the immigration complexities were too daunting. It looked impossible. I decided to study a Master’s Degree in the UK and reinforce my English. Right before completing my degree in England, I was offered a six-month internship at a startup in San Francisco. Financially, it was not the smartest decision — I would barely be able to afford rent, despite having better paid options in Europe. However, experiencing Silicon Valley was a lifelong dream. It wasn’t an obvious choice. But I ultimately packed my suitcase, left behind my family, girlfriend and friends, and relocated across the world. Landing in California My journey in the U.S. began with a J1 visa, intended for interns and relatively simple to secure with an employer’s backing. It was a suitable fit for my six-month plan, extendable to a full year, without any ambition for a longer stay. Yet, I worked extremely hard, and the situation changed when I was introduced to the possibility of obtaining an H-1B visa. Unlike the J1, the H-1B visa demands wage parity with U.S. citizens, allows for a stay of up to six years, and paves the way for permanent residency. Most importantly, it meant I could start laying down roots in the US, such as building my credit score, buying a car, or negotiating a long-term lease. First Immigration Problems My living situation dramatically improved when I traded my small, rat-filled room for a two-bedroom apartment in the Outer Sunset, sharing the space with a friend. I got a sizeable salary bump. However, the happiness was short-lived. H-1B visa applications had exceeded available spots for the first time in years, introducing a lottery. My coding skills, education, and value to my employer wouldn’t factor into this gamble. Anxiety mounted for a very long month, as friends celebrated their visa wins. I was left in the dark, bracing for bad news. Against the odds, relief came just a day after a disheartening talk with my immigration lawyer, granting me my first taste of luck. Reuniting with my girlfriend Sick. My H-1B visa approval meant I could make the US my home for six additional years, longer than Marina and I had been dating. As she was about to end her studies, we strategized on ways to reunite in the US. Marrying earlier was an option, but with H-1B restrictions preventing spouses from working, we looked for alternatives. The easiest path forward involved securing a student visa, leading to an 12-month work permit, followed by an H-1B visa application. In the competitive climate of 2015, her work visa acceptance felt nothing short of miraculous, becoming our story’s second lucky strike. Permanent Residency While six years might seem long, they pass quickly when you are busy and having fun. Halfway through, it became clear we needed to strategize for the future when it was time to renew my visa. My employer agreed to initiate the Green Card application, a lengthy and costly process requiring proof that I was indispensable for the company. Despite the complexities, our attorney believed the case would progress smoothly, estimating an 18-month completion time. Surprisingly, the initial phase went way faster than anticipated, prompting our attorney to suggest an immediate wedding for Marina and me, a necessary step to include her in the Green Card application. We quickly scheduled our wedding at the Spanish Consulate in San Francisco, departing from our original plan for a ceremony in Spain. More problems A year and a half in, expecting our Green Cards, we faced an unexpected challenge: our marriage, officiated at a consulate, was not recognized by US Immigration, compelling us to marry again, pay the associated fees again, and start the process over. This development was extremely frustrating, specially as my friend Jacob and I were contemplating founding a company, and the absence of a Green Card meant remaining as an employee. To rectify the situation, we promptly got remarried at San Mateo City Hall, choosing it for its rapid scheduling. Two months later we held another ceremony in Spain with our family and friends (our third marriage overall). The delay in our reapplication, exacerbated by the recent election of Trump and a subsequent slowdown in immigration services, led us into a stressful period of uncertainty. Our inability to make definite plans, from household purchases to housing arrangements left us anxiously awaiting any news on our application. As we navigated this uncertainty, the possibility of dedicating myself fully to our startup (later named RevenueCat) became increasingly dim. Going All In A pivotal moment came when our now startup, RevenueCat, was accepted into Y Combinator, requiring my full-time commitment. A big challenge due to my pending Green Card application. My immigration status became the biggest risk to our startup, even before launching. In searching for a solution, we identified a potential hack: an immigration loophole that allowed for employment changes under specific circumstances. It wasn’t risk free. There were no guarantees, and it involved giving up my H-1B status and the ability to travel. Should my Green Card application face rejection for any reason, I would instantly become an illegal immigrant. Deciding to take the gamble, we prepared the necessary documentation. To support our case, Jacob, my co-founder, had to write a letter stating that although my compensation was on the lower side, his, in the CEO role, was even lower. We also had to declare our company’s annual earnings ($0 at that time), and I suggested Jacob to specify it as less than $1 million. You should never lie to Homeland Security 😅. This leap of faith paid off; eight months later, we received our Green Card interview, where the immigration officer, making fun of our unique circumstances, granted approval on the spot. The Decision to Become American Those with an employment-based Green Card need a five-year stay in the US, compliant with all laws and tax requirements, to qualify for citizenship. While obtaining citizenship is not mandatory, and one might choose to stay a permanent resident indefinitely, citizenship confers full rights and responsibilities. Among these, the requirement to pay federal taxes forever, a big concern for many. If RevenueCat succeeds as we hope, I’m looking at significant tax payments, even if we end up moving back to Europe. The decision to embrace US citizenship came down to a simple reason: we can. We recognize the privilege of this choice, acknowledging the series of fortunate events that brought us here, aware that our journey could have taken decades had we originated from countries like India or China. Our twin daughters are blessed with dual citizenship, offering them a breadth of choices for their future. The opportunities the US has presented to our family are beyond what we once could dream. By becoming citizens, we gain a voice to influence immigration policies positively instead of blocking progress. My tax contributions have already reached the seven-figure mark. The continuation of our tax obligation is a small price to pay. And after all, there are some advantageous double taxation agreements 😉. Special thanks to my family for always supporting me and pushing me to live my dream in San Francisco. To Marina, my now wife, for joining me in this crazy adventure across the globe. To everyone at StepOne for running an amazing internship program. To Jesse, for believing in my potential and tackling the immigration challenges with me. And to my co-founder Jacob, for pushing me to take a leap of faith with my immigration status.

10 months ago 37 votes
Working with Miguel: A Practical Guide

Since reading ‘High Growth Handbook’ by Elad Gil, the value of writing a ‘Working with’ document became crystal clear to me. I am sharing mine externally to inspire other founders and leaders to reflect and write down their own working styles. These documents are incredibly beneficial, especially in a multi-timezone, remote setting like we have at RevenueCat. I’ve spent some time fine-tuning mine, and this is the updated version. Welcome to your go-to manual for understanding how to collaborate effectively with me. My Mindset: Logic-Driven, Plan-Oriented I’m a logical thinker, much like a computer. If A implies B and we have A, I’ll typically conclude B. Sticking to plans and predictability is my comfort zone, yet I value reactivity, especially when customer-related issues arise and are solvable. This company isn’t just a job for me; it’s my life’s work. I’m deeply invested in everything here — our technology, culture, team, and customers. I get inspired and energized by hard-working coworkers who believe in our mission even more than me. As a co-founder, I can offer a wealth of institutional knowledge and guidance. While I may not have all the answers, I’m usually good at pointing you in the right direction. RevenueCat is only a sum of it’s parts. Our teammates drive our culture and I want to make sure we are building a place that people want to be. If you have a suggestion on how to make RevenueCat an even cooler place to work for our teammates I’m always here to talk about it. How We’ll Operate Regular Check-ins: For my direct reports, expect weekly or bi-weekly one-on-one meetings. To make our discussions more focused, I prefer that we establish an agenda before our scheduled time together. Communication Protocols: My schedule doesn’t allow much room for impromptu calls. If something urgent pops up, message me on Slack first. Should it require a call, schedule it through Susannah, please never bypass her. Meeting Preparation: Come to meetings with an agenda to ensure productivity. Without one, I might dominate the conversation, potentially missing your crucial points. Let’s both be responsible for following up on action items. Team Support: I’m open to joining other team meetings, but please share the agenda in advance and mark my attendance as optional unless crucial. Problem-Solving Approach: My engineering background means I love tackling complex problems using a divide and conquer approach: by breaking them down into smaller, manageable chunks, solving each piece, and then combining them for a final solution. If we can improve a completely broken system to 90% functionality, that’s significant progress in my book! Communication Style Note-Taking: While I take meticulous notes, my current preferred tool doesn’t support sharing. If you wish to access these notes, it’s on you to set up a shared document in Google Docs, Notion, or Lattice. Information Filtering: I prefer having complete transparency and the ability to filter out unnecessary details myself. Always explicitly state if you need input from me, or else I’ll assume it’s for my information only. Feedback Style: Expect direct feedback from me. I’ll clearly differentiate between areas for improvement and significant performance concerns. Trust Dynamics: Consider my trust like a metaphorical ‘bucket’ that starts half-full for everyone and adjusts based on your actions. The more you fill this bucket, the more autonomy you’ll have. For Managers Transparency in Challenges: Startups are always broken one way or another. I prefer to hear any bad news about a project or a team member directly from you. Working together through challenges can strengthen our trust and working relationship. Progress and Concerns: During our 1:1’s, I’ll inquire about your team dynamics and direct reports’ progress. I encourage you to include any details in our 1:1 agenda and lead the conversation to address any performance concerns, project delays or notable achievements . Feedback Dynamics: I recognize the weight of my title. To avoid unnecessary tension, I prefer to provide critical feedback about your reports directly to you so you can address privately. On the other hand, if there is any commendable achievement by your team I will do my best to praise publicly. If you feel there is someone on your team that I should connect with or praise, please let me know. Encouraging our team and recognizing their strengths is something that is very important to me. Preferences and Pet Peeves What I like Doing your homework: No question is stupid, but always do your initial research before distracting the team. Being resolutive: Getting things done, unblocking yourself. Readable and consistent code. Proven, boring technology over unproven open source projects that is trending on Hacker News. Proactivity: See a problem? Fix it right away before anyone notices. Made a mistake? Build systems to prevent anyone else making the same one again. Double checking your work: Give your work (documents, presentations, pull requests) a quick self-review before presenting it to the team. Transparency: In a multi-tz, remote environment, over-communication is better than miscommunication. Healthy discussions. When there is a decision to make that is not clear, it’s because all the different approaches have pros and cons. Together we will be able to calibrate and choose the lesser evil. A short call (or loom) is preferred over constant Slack interruptions. What I don’t like Gossip and rumors: They destroy the culture. Be upfront. Cargo cult: Let’s not do something just because BIG CO does it. That’s the beauty of building something from scratch. Unnecessary blockers. You’re all pretty smart here! Always try to unblock yourself first. Lack of context in questions, emails, and discussions. Not speaking up when something isn’t clear. Recurrent mistakes or questions: One time, it’s totally expected. Two times, hmm. Three times, nah. Learn, document, and build systems. Complaining without taking any action to improve the situation. Sarcasm or other ways of communication violence during disagreements: When somebody wins an argument, most of the time, the whole team loses. Acknowledging My Flaws Overcommitment: I tend to take on more than I should, which inevitably affects my focus. While I’m working on this, please understand if I occasionally get sidetracked by emergencies. Communication while Debugging: When addressing issues, I might share unvalidated hypotheses, which can be confusing. I’m learning to communicate more clearly and only after verifying my thoughts. Problem-Solving Obsession: Unsolved problems keep me up at night, which isn’t ideal for my well-being. It’s a habit I’m aware of and trying to balance. Pessimistic Tendencies: In evaluating problems, I often veer towards catastrophic thinking rather than optimism, a trait I’m mindful of and trying to moderate. Office Hours To maximize my availability given my tight schedule, I’ve introduced ‘office hours.’ This time is open for anyone to schedule a 15-minute chat with me about any concerns or ideas you might have. Reach out to Susannah for scheduling details. Thanks for sticking with me till the end! These are my personal preferences, not commandments carved in stone. I’m stoked to collaborate, build awesome stuff, and, above all, have fun together!

a year ago 37 votes
My role as a founder CTO: Year Six

Another year as a founder CTO, and let me tell you, it’s been one for the books. I can’t remember a time in my life that was more demanding and emotionally draining. Those early years were filled with hard work, but we were also full of energy, ambition to build, and the sense that we had absolutely nothing to lose. As my dear friend Jacob used to quip, “Worst case scenario nobody dies”. Yet, everything takes on a new perspective when you’re responsible for the monetization infrastructure of over 30,000 apps and ensuring the livelihoods of not only your team but also your own family. While I would typically begin this series of posts with an array of metrics, this year has been a whirlwind of events that has taken precedence over mere numbers. So, dear friend, take a seat and allow me to share with you a deeply personal and epic firefighting tale and the battle to restore the flame of RevenueCat’s core values. The Year of Shipping We embarked on Q1 with big intentions and an ambitious roadmap. With seven new engineering teams, my role was to lead the one responsible for serving our larger customers. My days consisted of collaborating with our (still tiny) sales team, while simultaneously overseeing our support function. While I continued to provide technical guidance to several projects, I made the conscious decision to delegate the bulk of product development to the other teams. In hindsight, this decision proved to be a mistake. The teams were still finding their footing, with a mix of new hires, and there was a disconnect between engineering and product that needed addressing — a topic we’ll get into later. Nevertheless, the team I led was firing on all cylinders, delivering enterprise-level features at a hasty pace. From implementing single-sign-on in a matter of days, to tackling gnarly bugs, this team’s momentum was inspiring. I hoped that this stride would serve as a catalyst, motivating the rest of the teams to achieve a similar velocity. On the home front, my wife’s parental leave came to an end in January, marking the start of a new era where my hours were no longer flexible. Together, we embarked on the demanding task of caring for our twin babies. Little did I know how much the lack of sleep would impact me. Fatigue began to set in and my usual escape valves, such as surfing, turned into distant memories. Caffeine became my closest friend, helping me stay awake as I navigated the demands of work and family. I would spend my entire weekends lying in bed, trying to recover. I wrongly assumed it would be a short phase. Troubles never come alone On the fateful morning of March 9th, while I was soothing one of our crying babies at 4:30 AM, my WhatsApp began buzzing with messages from concerned fellow founders. Rumors were swirling that Silicon Valley Bank, the custodian of most VC-backed startup funds, was about to collapse. Within hours these whispers escalated into a full-blown bank run and we found ourselves unable to access our funds. Without going into the nitty-gritty details, it was an intensely stressful weekend. We were on the verge of a payroll crisis and we didn’t even have a functioning bank to transact with. However, we couldn’t afford to let this situation be what killed RevenueCat. We worked to expedite the opening of new bank accounts and explored multiple liquidity alternatives. Fortunately, we were privileged enough to entertain multiple options. One investor came to help, wiring funds from their personal account, and some of our loyal customers offered to pay in advance. Just as hope seemed to dwindle, the FDIC announced that they would guarantee all deposits on that Sunday afternoon. Crisis averted. Emotionally drained from the weekend’s trauma, we received another unexpected blow just a few days later: Y Combinator was discontinuing its Continuity Fund. This created a dilemma regarding the fate of their board seat, something we would have never anticipated. Just weeks prior, we had suffered a severe outage caused by our cloud provider. We tried to console ourselves, thinking, “At least all these problems are internal; we’re not dealing with downtime”. A Crisis of Reliability Our break was short-lived. Less than a week after the Silicon Valley Bank fiasco we experienced yet another major outage, and this time, it was self-inflicted. When you’re handling hundreds of thousands of API requests per second, even a few seconds of downtime can set off a cascade of alarms and potential sales losses. Our customers were understandably frustrated, and they didn’t hesitate to make their displeasure known through every available channel. It was heartbreaking to witness and I felt a deep sense of personal failure. This marked the third user-facing issue in a matter of months. It wasn’t something to sweep under the rug: our reputation was on the line and it was time to act. By this point, I was utterly sleep-deprived and my Apple Watch had begun sending me concerning health notifications. The day after we resolved the outage, my co-founder Jacob and I came up with an action plan. It was officially wartime. We needed to act decisively. We publicly unveiled our plan: to develop a robust fallback system independent of our current infrastructure. And we promised to deliver it within a week. Simultaneously, Jacob and I embarked on an apology tour, reaching out personally to some of our most worried customers. This was a painful but humbling experience for us, but it proved beneficial on multiple fronts. It allowed us to reiterate our commitment to becoming the best in-app subscription infrastructure provider in the world while gaining invaluable insights into our customers’ pain points. RC Fortress I rallied a small crew of engineers from different teams to build the first version of what we called “RevenueCat Fortress”. This component was designed to make sure end-customers could purchase seamlessly, even when our main servers were unavailable. It was a crazy week because we set ourselves a tight deadline but it helped boost our spirits and proved we could deliver software fast. The initial version of RevenueCat Fortress was quite simple – it operated behind the scenes on the server. But we didn’t stop there. We made it even better in the next iterations by adding SDK improvements such as offline entitlements. When it finally rolled out, it did so with flying colors. We even got to put it to the test during a major Apple outage and it saved the day for RevenueCat customers, making them immune to Apple’s downtime. Turning things around Looking back, the birth of RC Fortress marked the start of a shift in our culture. It got us back to the basics of reliability, fast delivery, and customer obsession. We couldn’t afford to spend months on extensive, untested projects. We had to rapidly build the features our customers valued most and iterate from there. We also realized that keeping things rock-solid wasn’t just the infrastructure team’s job; it was a global effort. Around the same time, we faced a couple of setbacks when we parted ways with two executives – the VP of People and the VP of Engineering. We tried to find a new VP of Engineering but couldn’t find a match that really excited us. So, the board agreed it would be best if I took the reins of the entire engineering organization again. Those days gave me a chance to get closer to the product teams again. Here’s where I spent most of my energy: Performance: I clarified expectations, provided feedback, and coached managers on performance management. Hiring: We tweaked our hiring process and re-calibrated interviewers’ expectations. Reliability and Quality: We were pretty good at doing post-mortems after issues but we had too many of them. They lacked detail and they weren’t followed through with action items. We needed a little bit of a cultural reset. We introduced dedicated incident Slack channels and clearly defined roles. Customer Obsession: Taking over the support team was eye-opening. It gave me a direct line to our product’s weak spots and what confused our customers. We started categorizing support tickets and sending them straight to the right product teams for triaging. Project Management: We focused on breaking projects into smaller chunks to deliver faster, instead of getting lost in never-ending projects. Education and Best Practices: I spent time educating other departments, especially post-sales teams, to avoid recurring mistakes that were slowing down our engineering progress. On top of all that, I reconnected with our customers more than ever. I hopped on planes to visit them at their offices and even worked our booth at a few conferences. It was a refreshing change to chat with users face-to-face, and hearing their unique challenges in person after a long time. Life is what happens when you’re busy running your startup We were fortunate enough to fly in my mother-in-law to assist with our babies, which made my travel plans possible. I finally felt more rested and even managed to squeeze in a few surfing sessions. Things were looking up both personally and professionally. I was eagerly anticipating our annual company-wide offsite, especially since I had missed most of the previous one due to my wife’s high-risk pregnancy. This time around I was geared up to address the entire engineering team, sharing the exciting changes and boosting morale. We were about to start winning again. But then, the day before my flight, I received a call from my father back in Spain. My mother had been rushed to the hospital, and she had been diagnosed with an extremely aggressive form of leukemia. Time seemed to stand still. I boarded the flight as planned, chugged two Red Bulls, and delivered that motivational talk to the whole team, while my mom was in a hospital bed thousands of miles away. This was hands down the toughest thing I’ve ever done as a startup founder. I left the offsite early and headed back to my hometown. Over the following weeks, I traveled back and forth around the globe, coordinating with my family. Sadly, my mother never left the hospital, she passed away merely a few weeks after the diagnosis. These are the things that always lurk in the back of your mind when you’re living 10,000 miles away from home, but you never truly believe they’ll happen. Until they do, and they shatter you. Keep on pushing The days that followed were far from easy. We were dealing with the launch of our biggest customer’s app, something we’d been preparing for a long time. The scale was enormous and the hard work of our team truly paid off. Our systems ran incredibly smoothly. It was a monumental victory, especially after the rocky start to the year. But, mentally, I wasn’t prepared to savor the moment. Yet, the energy post-offsite was infectious. People genuinely enjoyed meeting each other in real life and were fired up to start shipping. We couldn’t let this opportunity slip through our fingers. I paid homage to my mom’s teachings by continuing to press forward. RC Paywalls One of the major product ideas that had always been on our team’s wishlist was paywalls. We hadn’t tackled it because it seemed daunting and we lacked a product team with all the necessary skills. We couldn’t even estimate how long it would take to build. But, fueled by the success of RC Fortress, we decided to take a shot at it. We assembled a small team with members borrowed from different corners of the company. We didn’t mess with any reporting structures but appointed a leader. We went back to our roots, working in a hackathon-style frenzy for a couple of weeks to build a prototype. Just like in the good old days. And, boy, did the team rise to the occasion. We gave them some extra time and, in the end, they delivered one of our biggest product wins of the year. Shipping paywalls felt like a breath of fresh air and a clear sign that we still had our mojo. We were still capable of shipping software at lightning speed and keeping our customers excited. Based on all these lessons, the Head of Product and I started cooking up a brand new way of building products at RevenueCat. Engineering/Product/Design changes The complete process overhaul would warrant a couple of blog posts, but let me highlight the key changes to our workflow: We’ve reviewed all existing teams to determine whether they should continue as is, be replaced, or undergo changes in their mission or structure. We’ve rebalanced and clarified the responsibilities across Product, Engineering, and Design: Engineering takes the lead on feasibility, delivery, and developer experience, managing Linear, and overseeing technical architecture (and debt) roadmaps. Product is dedicated to customer value, business viability, and collaboration with sales and marketing teams. They also provide support to engineering in refining project scopes. Design is responsible for usability. We’ve formalized the role of Tech Lead, assigning them as the Directly Responsible Individuals for specific projects. They’re accountable for project success, with full backing from their Engineering Manager. It’s optional and project-dependent and doesn’t entail a title or salary change. We’ve acknowledged the need for engineering-driven initiatives, where PM and Design are involved on an as-needed basis. For projects with dependencies with other teams, we’ll designate a team member from the collaborating team as a formal interface. Our existing setup of stable product teams will remain the norm for most of our work. Temporary project teams will be established only when there’s a strong need for cross-team collaboration over a limited period. We’ll conduct monthly roadmap and shipping reviews with the founders and Head of Product. These reviews will provide insights into what we’re building, offer feedback opportunities, and help identify cross-functional dependencies and misalignments. 2024: The year of shipping + selling Collaborating with the Product team showcased the immense benefits of working closely together. Traditionally, Product reported directly to our CEO, which introduced unnecessary layers of indirection. In light of this and our recent addition of a VP of Sales, we decided it was time for a reorganization. Currently, Jacob (co-founder, and CEO), is overseeing Go to Market, People, and Operations, while I’m responsible for Engineering, Product, and Customer Engineering. We’ve brought in a VP of Customer Engineering, who reports to me and is in charge of Support and Technical Account Management. With our current headcount at 73 employees, my organization consists of 48 team members. Our executive team developed the most comprehensive planning effort to date. Our goal is to accelerate growth, focusing on sales and product delivery. We will avoid distractions by being extremely strategic at hiring. The past quarter showcased the strength of our engineering and product teams. New team members have been onboarded successfully, contributing meaningfully, and our management structure is finally robust. It took a bit of time for the “year of shipping” to fully materialize, nearly a year later, but customers have taken notice and we’re capitalizing on this momentum. On the enterprise sales front, I’m extremely bullish. We’ve secured the biggest deals in the company’s history. RevenueCat has evolved beyond being a product just for indie developers. However, we acknowledge the need to continue closing the product-market fit gap for enterprise clients. We’ve gained valuable insights into enterprise needs, and we’ll keep developing new products and features tailored to them. Indie developers will also take advantage of them to make more money. In 2024, the collaboration between our go-to-market and engineering teams will be critical. Highlights This year, as you’ve probably noticed, was a tough one. However, besides the challenges, there were several remarkable achievements to celebrate: We truly shipped. Our second hackathon, spanning an entire week, was an epic success. Many of the projects launched immediately, directly benefiting our customers. We had the privilege of collaborating with prominent brands and companies, including none other than Arnold Schwarzenegger himself. We created an astonishing amount of high-quality content. Our SubClub podcast outperformed all my expectations. During the chaos of the bank run, we discovered that one of our idols was not only a RevenueCat customer but also a devoted fan. We experimented with fresh team topologies and processes, and they turned out to be successful. We fine-tuned our vision for building a winning team, offering improved feedback, clearer expectations, and timely performance management. Jacob and I are no longer the sole authorities on Apple and Google subscriptions within the company. We successfully recruited seasoned executives to join our team. Our core infrastructure team accomplished monumental feats. We now support over 1 billion API requests daily, transitioned to our own data platform, and developed our own memcached client. All while maintaining flat costs despite the increase in load. Learnings It’s impossible to achieve peak performance without attention to health, exercise, and sleep. I’m no longer in my twenties. Complexity is the root of all evil. Startups and software are inherently complex, so avoid introducing unnecessary complexity. Begin by building the simplest feature or process, debug it, and then iterate as needed. Starting a business is tough, but launching a remote startup is an even greater challenge. Scaling a remote startup while parenting two under two is a herculean effort. Building a brand takes years but its reputation can be destroyed in an instant. Protect the integrity of your brand at all costs. Every new team member should add value, and especially so in a startup. Some provide immense leverage, while others become bottlenecks. The trickiest are those in the middle, who often end up becoming bottlenecks. Founders usually spot this within the first few weeks. Letting someone go is a taxing task. Even when managers believe it’s the right thing to do, it often requires a significant amount of support and guidance. Transparency in times of crisis pays dividends. Employees want to be treated like adults, and it builds trust. The same applies externally. Early worries often become baseless. By the time they become actual problems, your company might have died, you might have gained experience, or you might have hired the right talent to tackle them. SOC 2 auditors may request unconventional supporting evidence, such as employee performance reviews. Developers love socks. I’m so fortunate to have the world’s best co-founder. At this stage, my role is much more aligned with that of a founder than a traditional CTO or VP of Engineering. I continue to address issues as if they were technical problems, but my responsibilities extend well beyond the technology area. Life keeps moving forward, with its share of highs and lows. Life is too short, so you have to ensure the journey remains fun. For me, that means working with people who inspire me, and serving customers I genuinely care about. I really hope you enjoyed reading this post. I’m aware it’s a lot longer than my previous ones, but there were so many stories to share. As always, my intention was to share it with complete honesty and transparency, avoiding the hype that often surrounds startups. If you are facing similar challenges and want to connect and share experiences, please do not hesitate to reach out on Twitter or shoot me an email! Special thanks to my co-founder Jacob, the whole RevenueCat team, and our valuable customers. I also need to express my eternal gratitude to all the CTOs and leaders who have been kind enough to share their experiences over these years. Shoutout to Dani Lopez, Peter Silberman, Alex Plugaru, Kwindla Hultman Kramer, João Batalha, Karri Saarinen, Miguel Martinez Triviño, Sam Lown, Javi Santana, Pau Ramón, Javier Maestro, Matias Woloski, Tobias Balling, Jason Warner, and Will Larson. Our investors and early believers Jason Lemkin, Anu Hariharan, Mark Fiorentino, Mark Goldberg, Andrew Maguire, Gustaf Alströmer, and Nico Wittenborn. I want to convey my deep gratitude to my amazing wife, Marina, who has been my unwavering source of inspiration and support from the very beginning, and for blessing us with our two precious daughters. I cannot close this post without thanking my mom, who made countless sacrifices to mold me into the person I am today. I promise you will look down on us with pride the day we ring the bell in New York. I love you dearly.

a year ago 31 votes

More in programming

Diagnosis in engineering strategy.

Once you’ve written your strategy’s exploration, the next step is working on its diagnosis. Diagnosis is understanding the constraints and challenges your strategy needs to address. In particular, it’s about doing that understanding while slowing yourself down from deciding how to solve the problem at hand before you know the problem’s nuances and constraints. If you ever find yourself wanting to skip the diagnosis phase–let’s get to the solution already!–then maybe it’s worth acknowledging that every strategy that I’ve seen fail, did so due to a lazy or inaccurate diagnosis. It’s very challenging to fail with a proper diagnosis, and almost impossible to succeed without one. The topics this chapter will cover are: Why diagnosis is the foundation of effective strategy, on which effective policy depends. Conversely, how skipping the diagnosis phase consistently ruins strategies A step-by-step approach to diagnosing your strategy’s circumstances How to incorporate data into your diagnosis effectively, and where to focus on adding data Dealing with controversial elements of your diagnosis, such as pointing out that your own executive is one of the challenges to solve Why it’s more effective to view difficulties as part of the problem to be solved, rather than a blocking issue that prevents making forward progress The near impossibility of an effective diagnosis if you don’t bring humility and self-awareness to the process Into the details we go! This is an exploratory, draft chapter for a book on engineering strategy that I’m brainstorming in #eng-strategy-book. As such, some of the links go to other draft chapters, both published drafts and very early, unpublished drafts. Diagnosis is strategy’s foundation One of the challenges in evaluating strategy is that, after the fact, many effective strategies are so obvious that they’re pretty boring. Similarly, most ineffective strategies are so clearly flawed that their authors look lazy. That’s because, as a strategy is operated, the reality around it becomes clear. When you’re writing your strategy, you don’t know if you can convince your colleagues to adopt a new approach to specifying APIs, but a year later you know very definitively whether it’s possible. Building your strategy’s diagnosis is your attempt to correctly recognize the context that the strategy needs to solve before deciding on the policies to address that context. Done well, the subsequent steps of writing strategy often feel like an afterthought, which is why I think of diagnosis as strategy’s foundation. Where exploration was an evaluation-free activity, diagnosis is all about evaluation. How do teams feel today? Why did that project fail? Why did the last strategy go poorly? What will be the distractions to overcome to make this new strategy successful? That said, not all evaluation is equal. If you state your judgment directly, it’s easy to dispute. An effective diagnosis is hard to argue against, because it’s a web of interconnected observations, facts, and data. Even for folks who dislike your conclusions, the weight of evidence should be hard to shift. Strategy testing, explored in the Refinement section, takes advantage of the reality that it’s easier to diagnose by doing than by speculating. It proposes a recursive diagnosis process until you have real-world evidence that the strategy is working. How to develop your diagnosis Your strategy is almost certain to fail unless you start from an effective diagnosis, but how to build a diagnosis is often left unspecified. That’s because, for most folks, building the diagnosis is indeed a dark art: unspecified, undiscussion, and uncontrollable. I’ve been guilty of this as well, with The Engineering Executive’s Primer’s chapter on strategy staying silent on the details of how to diagnose for your strategy. So, yes, there is some truth to the idea that forming your diagnosis is an emergent, organic process rather than a structured, mechanical one. However, over time I’ve come to adopt a fairly structured approach: Braindump, starting from a blank sheet of paper, write down your best understanding of the circumstances that inform your current strategy. Then set that piece of paper aside for the moment. Summarize exploration on a new piece of paper, review the contents of your exploration. Pull in every piece of diagnosis from similar situations that resonates with you. This is true for both internal and external works! For each diagnosis, tag whether it fits perfectly, or needs to be adjusted for your current circumstances. Then, once again, set the piece of paper aside. Mine for distinct perspectives on yet another blank page, talking to different stakeholders and colleagues who you know are likely to disagree with your early thinking. Your goal is not to agree with this feedback. Instead, it’s to understand their view. The Crux by Richard Rumelt anchors diagnosis in this approach, emphasizing the importance of “testing, adjusting, and changing the frame, or point of view.” Synthesize views into one internally consistent perspective. Sometimes the different perspectives you’ve gathered don’t mesh well. They might well explicitly differ in what they believe the underlying problem is, as is typical in tension between platform and product engineering teams. The goal is to competently represent each of these perspectives in the diagnosis, even the ones you disagree with, so that later on you can evaluate your proposed approach against each of them. When synthesizing feedback goes poorly, it tends to fail in one of two ways. First, the author’s opinion shines through so strongly that it renders the author suspect. Your goal is never to agree with every team’s perspective, just as your diagnosis should typically avoid crowning any perspective as correct: a reader should generally be appraised of the details and unaware of the author. The second common issue is when a group tries to jointly own the synthesis, but create a fractured perspective rather than a unified one. I generally find that having one author who is accountable for representing all views works best to address both of these issues. Test drafts across perspectives. Once you’ve written your initial diagnosis, you want to sit down with the people who you expect to disagree most fervently. Iterate with them until they agree that you’ve accurately captured their perspective. It might be that they disagree with some other view points, but they should be able to agree that others hold those views. They might argue that the data you’ve included doesn’t capture their full reality, in which case you can caveat the data by saying that their team disagrees that it’s a comprehensive lens. Don’t worry about getting the details perfectly right in your initial diagnosis. You’re trying to get the right crumbs to feed into the next phase, strategy refinement. Allowing yourself to be directionally correct, rather than perfectly correct, makes it possible to cover a broad territory quickly. Getting caught up in perfecting details is an easy way to anchor yourself into one perspective prematurely. At this point, I hope you’re starting to predict how I’ll conclude any recipe for strategy creation: if these steps feel overly mechanical to you, adjust them to something that feels more natural and authentic. There’s no perfect way to understand complex problems. That said, if you feel uncertain, or are skeptical of your own track record, I do encourage you to start with the above approach as a launching point. Incorporating data into your diagnosis The strategy for Navigating Private Equity ownership’s diagnosis includes a number of details to help readers understand the status quo. For example the section on headcount growth explains headcount growth, how it compares to the prior year, and providing a mental model for readers to translate engineering headcount into engineering headcount costs: Our Engineering headcount costs have grown by 15% YoY this year, and 18% YoY the prior year. Headcount grew 7% and 9% respectively, with the difference between headcount and headcount costs explained by salary band adjustments (4%), a focus on hiring senior roles (3%), and increased hiring in higher cost geographic regions (1%). If everyone evaluating a strategy shares the same foundational data, then evaluating the strategy becomes vastly simpler. Data is also your mechanism for supporting or critiquing the various views that you’ve gathered when drafting your diagnosis; to an impartial reader, data will speak louder than passion. If you’re confident that a perspective is true, then include a data narrative that supports it. If you believe another perspective is overstated, then include data that the reader will require to come to the same conclusion. Do your best to include data analysis with a link out to the full data, rather than requiring readers to interpret the data themselves while they are reading. As your strategy document travels further, there will be inevitable requests for different cuts of data to help readers understand your thinking, and this is somewhat preventable by linking to your original sources. If much of the data you want doesn’t exist today, that’s a fairly common scenario for strategy work: if the data to make the decision easy already existed, you probably would have already made a decision rather than needing to run a structured thinking process. The next chapter on refining strategy covers a number of tools that are useful for building confidence in low-data environments. Whisper the controversial parts At one time, the company I worked at rolled out a bar raiser program styled after Amazon’s, where there was an interviewer from outside the team that had to approve every hire. I spent some time arguing against adding this additional step as I didn’t understand what we were solving for, and I was surprised at how disinterested management was about knowing if the new process actually improved outcomes. What I didn’t realize until much later was that most of the senior leadership distrusted one of their peers, and had rolled out the bar raiser program solely to create a mechanism to control that manager’s hiring bar when the CTO was disinterested holding that leader accountable. (I also learned that these leaders didn’t care much about implementing this policy, resulting in bar raiser rejections being frequently ignored, but that’s a discussion for the Operations for strategy chapter.) This is a good example of a strategy that does make sense with the full diagnosis, but makes little sense without it, and where stating part of the diagnosis out loud is nearly impossible. Even senior leaders are not generally allowed to write a document that says, “The Director of Product Engineering is a bad hiring manager.” When you’re writing a strategy, you’ll often find yourself trying to choose between two awkward options: Say something awkward or uncomfortable about your company or someone working within it Omit a critical piece of your diagnosis that’s necessary to understand the wider thinking Whenever you encounter this sort of debate, my advice is to find a way to include the diagnosis, but to reframe it into a palatable statement that avoids casting blame too narrowly. I think it’s helpful to discuss a few concrete examples of this, starting with the strategy for navigating private equity, whose diagnosis includes: Based on general practice, it seems likely that our new Private Equity ownership will expect us to reduce R&D headcount costs through a reduction. However, we don’t have any concrete details to make a structured decision on this, and our approach would vary significantly depending on the size of the reduction. There are many things the authors of this strategy likely feel about their state of reality. First, they are probably upset about the fact that their new private equity ownership is likely to eliminate colleagues. Second, they are likely upset that there is no clear plan around what they need to do, so they are stuck preparing for a wide range of potential outcomes. However they feel, they don’t say any of that, they stick to precise, factual statements. For a second example, we can look to the Uber service migration strategy: Within infrastructure engineering, there is a team of four engineers responsible for service provisioning today. While our organization is growing at a similar rate as product engineering, none of that additional headcount is being allocated directly to the team working on service provisioning. We do not anticipate this changing. The team didn’t agree that their headcount should not be growing, but it was the reality they were operating in. They acknowledged their reality as a factual statement, without any additional commentary about that statement. In both of these examples, they found a professional, non-judgmental way to acknowledge the circumstances they were solving. The authors would have preferred that the leaders behind those decisions take explicit accountability for them, but it would have undermined the strategy work had they attempted to do it within their strategy writeup. Excluding critical parts of your diagnosis makes your strategies particularly hard to evaluate, copy or recreate. Find a way to say things politely to make the strategy effective. As always, strategies are much more about realities than ideals. Reframe blockers as part of diagnosis When I work on strategy with early-career leaders, an idea that comes up a lot is that an identified problem means that strategy is not possible. For example, they might argue that doing strategy work is impossible at their current company because the executive team changes their mind too often. That core insight is almost certainly true, but it’s much more powerful to reframe that as a diagnosis: if we don’t find a way to show concrete progress quickly, and use that to excite the executive team, our strategy is likely to fail. This transforms the thing preventing your strategy into a condition your strategy needs to address. Whenever you run into a reason why your strategy seems unlikely to work, or why strategy overall seems difficult, you’ve found an important piece of your diagnosis to include. There are never reasons why strategy simply cannot succeed, only diagnoses you’ve failed to recognize. For example, we knew in our work on Uber’s service provisioning strategy that we weren’t getting more headcount for the team, the product engineering team was going to continue growing rapidly, and that engineering leadership was unwilling to constrain how product engineering worked. Rather than preventing us from implementing a strategy, those components clarified what sort of approach could actually succeed. The role of self-awareness Every problem of today is partially rooted in the decisions of yesterday. If you’ve been with your organization for any duration at all, this means that you are directly or indirectly responsible for a portion of the problems that your diagnosis ought to recognize. This means that recognizing the impact of your prior actions in your diagnosis is a powerful demonstration of self-awareness. It also suggests that your next strategy’s success is rooted in your self-awareness about your prior choices. Don’t be afraid to recognize the failures in your past work. While changing your mind without new data is a sign of chaotic leadership, changing your mind with new data is a sign of thoughtful leadership. Summary Because diagnosis is the foundation of effective strategy, I’ve always found it the most intimidating phase of strategy work. While I think that’s a somewhat unavoidable reality, my hope is that this chapter has somewhat prepared you for that challenge. The four most important things to remember are simply: form your diagnosis before deciding how to solve it, try especially hard to capture perspectives you initially disagree with, supplement intuition with data where you can, and accept that sometimes you’re missing the data you need to fully understand. The last piece in particular, is why many good strategies never get shared, and the topic we’ll address in the next chapter on strategy refinement.

9 hours ago 2 votes
My friend, JT

I’ve had a cat for almost a third of my life.

an hour ago 2 votes
[Course Launch] Hands-on Introduction to X86 Assembly

A Live, Interactive Course for Systems Engineers

4 hours ago 1 votes
It’s cool to care

I’m sitting in a small coffee shop in Brooklyn. I have a warm drink, and it’s just started to snow outside. I’m visiting New York to see Operation Mincemeat on Broadway – I was at the dress rehearsal yesterday, and I’ll be at the opening preview tonight. I’ve seen this show more times than I care to count, and I hope US theater-goers love it as much as Brits. The people who make the show will tell you that it’s about a bunch of misfits who thought they could do something ridiculous, who had the audacity to believe in something unlikely. That’s certainly one way to see it. The musical tells the true story of a group of British spies who tried to fool Hitler with a dead body, fake papers, and an outrageous plan that could easily have failed. Decades later, the show’s creators would mirror that same spirit of unlikely ambition. Four friends, armed with their creativity, determination, and a wardrobe full of hats, created a new musical in a small London theatre. And after a series of transfers, they’re about to open the show under the bright lights of Broadway. But when I watch the show, I see a story about friendship. It’s about how we need our friends to help us, to inspire us, to push us to be the best versions of ourselves. I see the swaggering leader who needs a team to help him truly achieve. The nervous scientist who stands up for himself with the support of his friends. The enthusiastic secretary who learns wisdom and resilience from her elder. And so, I suppose, it’s fitting that I’m not in New York on my own. I’m here with friends – dozens of wonderful people who I met through this ridiculous show. At first, I was just an audience member. I sat in my seat, I watched the show, and I laughed and cried with equal measure. After the show, I waited at stage door to thank the cast. Then I came to see the show a second time. And a third. And a fourth. After a few trips, I started to see familiar faces waiting with me at stage door. So before the cast came out, we started chatting. Those conversations became a Twitter community, then a Discord, then a WhatsApp. We swapped fan art, merch, and stories of our favourite moments. We went to other shows together, and we hung out outside the theatre. I spent New Year’s Eve with a few of these friends, sitting on somebody’s floor and laughing about a bowl of limes like it was the funniest thing in the world. And now we’re together in New York. Meeting this kind, funny, and creative group of people might seem as unlikely as the premise of Mincemeat itself. But I believed it was possible, and here we are. I feel so lucky to have met these people, to take this ridiculous trip, to share these precious days with them. I know what a privilege this is – the time, the money, the ability to say let’s do this and make it happen. How many people can gather a dozen friends for even a single evening, let alone a trip halfway round the world? You might think it’s silly to travel this far for a theatre show, especially one we’ve seen plenty of times in London. Some people would never see the same show twice, and most of us are comfortably into double or triple-figures. Whenever somebody asks why, I don’t have a good answer. Because it’s fun? Because it’s moving? Because I enjoy it? I feel the need to justify it, as if there’s some logical reason that will make all of this okay. But maybe I don’t have to. Maybe joy doesn’t need justification. A theatre show doesn’t happen without people who care. Neither does a friendship. So much of our culture tells us that it’s not cool to care. It’s better to be detached, dismissive, disinterested. Enthusiasm is cringe. Sincerity is weakness. I’ve certainly felt that pressure – the urge to play it cool, to pretend I’m above it all. To act as if I only enjoy something a “normal” amount. Well, fuck that. I don’t know where the drive to be detached comes from. Maybe it’s to protect ourselves, a way to guard against disappointment. Maybe it’s to seem sophisticated, as if having passions makes us childish or less mature. Or perhaps it’s about control – if we stay detached, we never have to depend on others, we never have to trust in something bigger than ourselves. Being detached means you can’t get hurt – but you’ll also miss out on so much joy. I’m a big fan of being a big fan of things. So many of the best things in my life have come from caring, from letting myself be involved, from finding people who are a big fan of the same things as me. If I pretended not to care, I wouldn’t have any of that. Caring – deeply, foolishly, vulnerably – is how I connect with people. My friends and I care about this show, we care about each other, and we care about our joy. That care and love for each other is what brought us together, and without it we wouldn’t be here in this city. I know this is a once-in-a-lifetime trip. So many stars had to align – for us to meet, for the show we love to be successful, for us to be able to travel together. But if we didn’t care, none of those stars would have aligned. I know so many other friends who would have loved to be here but can’t be, for all kinds of reasons. Their absence isn’t for lack of caring, and they want the show to do well whether or not they’re here. I know they care, and that’s the important thing. To butcher Tennyson: I think it’s better to care about something you cannot affect, than to care about nothing at all. In a world that’s full of cynicism and spite and hatred, I feel that now more than ever. I’d recommend you go to the show if you haven’t already, but that’s not really the point of this post. Maybe you’ve already seen Operation Mincemeat, and it wasn’t for you. Maybe you’re not a theatre kid. Maybe you aren’t into musicals, or history, or war stories. That’s okay. I don’t mind if you care about different things to me. (Imagine how boring the world would be if we all cared about the same things!) But I want you to care about something. I want you to find it, find people who care about it too, and hold on to them. Because right now, in this city, with these people, at this show? I’m so glad I did. And I hope you find that sort of happiness too. Some of the people who made this trip special. Photo by Chloe, and taken from her Twitter. Timing note: I wrote this on February 15th, but I delayed posting it because I didn’t want to highlight the fact I was away from home. [If the formatting of this post looks odd in your feed reader, visit the original article]

yesterday 3 votes
Stick with the customer

One of the biggest mistakes that new startup founders make is trying to get away from the customer-facing roles too early. Whether it's customer support or it's sales, it's an incredible advantage to have the founders doing that work directly, and for much longer than they find comfortable. The absolute worst thing you can do is hire a sales person or a customer service agent too early. You'll miss all the golden nuggets that customers throw at you for free when they're rejecting your pitch or complaining about the product. Seeing these reasons paraphrased or summarized destroy all the nutrients in their insights. You want that whole-grain feedback straight from the customers' mouth!  When we launched Basecamp in 2004, Jason was doing all the customer service himself. And he kept doing it like that for three years!! By the time we hired our first customer service agent, Jason was doing 150 emails/day. The business was doing millions of dollars in ARR. And Basecamp got infinitely, better both as a market proposition and as a product, because Jason could funnel all that feedback into decisions and positioning. For a long time after that, we did "Everyone on Support". Frequently rotating programmers, designers, and founders through a day of answering emails directly to customers. The dividends of doing this were almost as high as having Jason run it all in the early years. We fixed an incredible number of minor niggles and annoying bugs because programmers found it easier to solve the problem than to apologize for why it was there. It's not easy doing this! Customers often offer their valuable insights wrapped in rude language, unreasonable demands, and bad suggestions. That's why many founders quit the business of dealing with them at the first opportunity. That's why few companies ever do "Everyone On Support". That's why there's such eagerness to reduce support to an AI-only interaction. But quitting dealing with customers early, not just in support but also in sales, is an incredible handicap for any startup. You don't have to do everything that every customer demands of you, but you should certainly listen to them. And you can't listen well if the sound is being muffled by early layers of indirection.

yesterday 4 votes