I just finished listening to Lenny’s conversation with Nan Yu, Head of Product at Linear, about what it takes to build a great SaaS product. Like many SaaS apps, the Kibu team and I have taken inspiration from Linear. But as we plan our roadmap and implement new solutions, I ask myself: What’s preventing us from building a product as beautiful as Linear, Slack, or Figma? Sure, time and resources matter, but I sense deeper things at play. Lenny and Nan’s conversation shed light on Linear’s approach and helped me articulate some thoughts: No Dogfooding Nan said that ideas for SaaS apps often start as useful products inside of larger companies. A typical story: a developer solves a personal problem, shares it with her coworkers, gets tons of praise, and considers if other companies have the same problem. I recall the story of Slack going a lot like this, and I suspect Linear is similar. The advantage of this approach is that the founder is customer zero. By building for yourself, user empathy has an instantaneous feedback loop, allowing you to rapidly build based off “vibe” alone. This is obvious advice, as the “built by X, for X” has been a marketing cliché for decades. It explains why the most lauded products in app design are almost always built by a team who can dogfood their own product. Kibu cannot dogfood its own product. As a content provider and documentation platform built for disability providers, Kibu operates with no day-to-day usage of its own product, as one may see at Linear, Slack, or Figma. Without dogfooding, “vibe development” is overshadowed by the voice of the customer. Of course, there’s nothing wrong with customer feedback, but Kibu’s lack of dogfooding handicaps our ability to have that “spidey-sense” of our customers’ needs. This could lead us down a complicated or unscalable path. I am particularly concerned with the latter, as our stellar dev team always ensures the UX passes user acceptability. I wonder how Kibu can mitigate our inability to dogfood: Try to dogfood: We once tried dogfooding by documenting our company goals and providing weekly updates in Kibu (similar to how our customers provide daily updates to their special needs members’ life plan goals). This was a positive step but still a square peg in a round hole. We simply do not operate with the same speed, setting, vocabulary, or consequences as our customers. Hire industry folks: Wow, wouldn’t it be nice to hire a former caretaker that turned into a valuable SaaS contributor! We’re starting to find those on the business side, but we haven’t found an engineer that fits that description. Regardless, by joining Kibu, the employee would have left the industry and no longer be engaging in Kibu. I assume that Strava developers still jog after getting hired lol… Ignore the issue and build: This has been our status quo and likely will be for a while. Let’s double down on customer feedback by scheduling recurring meetings with diverse users. Maybe we even pay them! Is there a company that we can take inspiration from that’s been in our position? What’s the most beautiful app that can’t be dogfooded? My first thought is Shopify, as I’m guessing Tobi Lütke and the whole team don’t personally maintain an e-commerce snowboard shop. Let me know if you can think of other companies. Saying No to “The Man” On the topic of preventing bloat, Nan said Linear is hyper-focused on delivering an exceptional IC experience and is willing to turn down feature requests that don’t align with that vision. For example, if Nan got a request from a middle manager to make end-of-month reporting slightly easier, Linear will deny that request if it means the IC’s work is strained a bit. This “bottom-up” prioritization philosophy is downright enviable! Kibu is in the business of compliance, meaning that we are limited to the needs of our customers’ regulators. If a government agency or grant provider want our customer to complete a 3-page questionnaire for every member every day, then our customer has no choice but to pass that requirement down to us. Our ability to design a frictionless experience for ICs hits a ceiling when met with regulation, no matter how dumb. This hindrance is particularly frustrating because we recognize the economic value that an exceptional IC UX could bring to our customers. If a low-level caretaker can take notes and track attendance on a tool that won’t make them want to blow their brains out, then: The data will be better, incurring less failed audits and penalties. The data will be better, allowing management to better identify inefficiencies that lead to better resource allocation. The staff will spend less time record-keeping and more time caring, leading to better outcomes and success stories. At the same time, regulation is why Kibu Documentation exists in the first place, so if we’re sticking to a Linear-like “bottom-up” product strategy, then it is our duty to make compliance painless, if not a little fun. Reports Come Second: While the economic buyer and regulators relentlessly emphasize the importance of reports, Kibu must remember that reporting is merely a representation of rows and columns. What truly matters is the data inside—which aligns with our philosophy of prioritizing the IC’s data input experience. Kibu has already done a great job delegating customers’ reporting needs to the Customer Success team (hey, that’s me!) with custom Looker reports. Customers stay happy with white-glove reporting, while our product team remains focused on ICs. No BS copy: On the front page of every customer’s Documentation homepage, we have large text that reads “Your org is X% compliant. Found out why” If the goal is compliance, then let’s not blur anything. I’d rather sacrifice a little extra text on the page if it means our nontechnical users know exactly where to go and why. We should take this one step further and extend it to each entity in Kibu, like the member: “Here’s what you need to do to be fully compliant with Athena…“ More unicorns: Whenever you complete a task in Asana, a unicorn flies across your page! So cool. Per my bullet points above, a fun Kibu experience will lead to better financial outcomes for our customers. Tiny Thoughts Okay, the two sections above were the most provocative. Here are some more takeaways that Kibu is already doing. If we’re not, I don’t think it would be too controversial to implement: Y-combinatify Kibu: Our marketing page should be fast, fun, minimal, with lots of polished-up screenshots of our product (like Superhuman or Mintlify). Our brand should be “the new kids on the block” or “finally… Silicon Valley’s best are solving my disability provider problems” Say No to Enterprise: Linear demonstrates great restraint in saying no to Enterprise-level requests that they believe will lead to poor long-term growth. My last company experienced this, and I’m wary of going through it again. The 11-star Experience: The Linear team occasionally plays in a world where resources are unlimited and they can design the best gosh-darn experience. They’re always surprised by how many ideas are viable! Kibu should do the same… I love one developer’s idea of “Call Kibu”, where an IC can simply call a phone number and log their notes for the day- having a back-and-forth conversation with a robot who knows all compliance requirements.

Between 2009 and 2012, Apple iPhones and iPod Touches included a feature called “Send to YouTube” that allowed users to upload videos directly to YouTube from the Photos app. The feature worked… really well. In fact, YouTube reported a 1700% increase in total video uploads during the first half of 2009- crediting that growth to its strong integrative ties to Apple and social networks. However, this two-click upload feature was short-lived when Apple severed ties with YouTube by removing its homegrown app in 2012. While Send to YouTube can be thoroughly analyzed as a milestone on the “frenemy” timeline between Apple and Google, I want to explore a pleasant consequence of this moment. Apple uses the ‘IMG_XXXX’ naming convention for all images and videos captured on iOS devices, where XXXX is a unique sequence number¹. The first image you take is named “IMG_0001”, the second is “IMG_0002” and so on. During the Send to YouTube era of 2009 and 2012, the title of one’s YouTube video was defaulted to this naming convention. Unwitting content creators would then upload their videos on a public site with a barely-searchable name. To this day, there are millions of these videos. Try searching for “IMG_XXXX” on YouTube, replacing “XXXX” with your favorite numbers (I used my birthday, 0416). See what you get! There’s something surreal about these videos that engages you in a way you’ve never felt. None were edited, produced, or paraded for mass viewing. In fact, many were likely uploaded by accident or with a misunderstanding that complete strangers could see it. YouTube automatically removes harmful or violent content, so what remains exists in a unique, almost paradoxical state: forbidden, yet harmless. Putting all this together, searching IMG_XXXX offers the most authentic social feed ever seen on the Internet- in video, no less! While many videos are redundant snippets of a concerts, basketball games, or kids’ recitals, you also get one-of-a-kind videos that provides a glimpse into a complete stranger’s life. You’ll see a tumultuous event that made them, their partner, or their friend say, “hey, let’s record this”. I’d like to show you three of these videos that I found in my search. IMG_0416 (Mar 17, 2015) - 23 views The video shows a woman excitedly unboxing a book she received in the mail. From context clues, she seems to be a wife and mother from Memphis who’s unboxing the first published copy of her book. She thanks the friends, family, and publishers who made this happen. After a quick Google Search, I was able to find the book: A Profit / Prophet to Her Husband: Are you ready to be a wife? The book is meant “to help wives understand who they are and who they were designed to be.” It clocks in at 94 pages and has 30 ratings on Amazon! Go IMG_0416! I don’t care what you’re creating- I’m just a fan of creators. It looks like she kept at it- making a second book in 2020! IMG_0416.MOV (June 24, 2015) - 26 views The video appears to show a woman playing a matching card game that teaches you “the basics of the potash stuff” according to the cameraman. As the woman (who I assume is the cameraman’s supportive mother) flips two matching cards, she reads off the countries who produce the most potash. I honestly didn’t know anything about potash! Turns out that it is a mineral with large amount of potassium, which is helpful as a plant fertilizer. With Canada producing the largest reserves in the world, the vast majority of Canadian potash is found in Saskatchewan. I wonder if this family lives in Canada. Or, if this is just another school project of useless facts… I miss those! IMG_0416 (Feb 8, 2011) - 114 views Let’s end on a fun one. The video shows a young man snorting powdered sugar and dealing with the consequences of it. Given his BU hoodie, Dunkin’ Donuts location, and ironic depiction of drug use, I gotta say this is a VERY Boston video. What’s genuinely heartwarming is the shared laughter between the man, the camerawoman, and the motherly figure leaving Dunkin’. The camerawoman calls her “Myra”, suggesting they all know each other. We have nothing better to do, so we’re snorting powdered sugar captures an essence of suburban America that I’m sure many of us can relate to. Edit: 11/3/24 IMG_0417 (Mar 14, 2014) - 16 views I found this after posting, and it’s just too amazing to not include… a woman filming her partner as he finds out she’s pregnant. Assuming all has gone well, the child is now almost 10 years old. I wonder if the family even knows this video still exists. After posting this on Hackernews, it looks like somebody commented on the video lol. I hope the family receives a notification it and is able to share this with their kid. ¹ Edit: The IMG_XXXX sequence isn’t truly unique—after 10,000 photos, the numbering restarts at IMG_0001 (Source).

I just finished reading The Inner Game of Tennis by Tim Gallwey. Originally published in 1974, the book explores how the thoughts of an athlete affect their game. It’s lauded as being at the forefront of what we now call “sports psychology”. Although my competitive sports days are over, I was still intrigued to read it in context of my current life as a startup professional, rec basketball player, and coach. Here are a few takeaways that I have from the book. To preface, Gallwey talks a lot about Self 1 and Self 2. Put simply, Self 1 is the critical, judgmental voice in your head, while Self 2 is the instinctive, natural self that performs effortlessly when trusted. The goal is to remove Self 1 as much as possible so Self 2 can perform. How to Learn “To Self 2, a picture is worth a thousand words. It learns by watching the actions of others, as well as by performing actions itself… The benefits to your game come not from analyzing the strokes of top players, but from concentrating without thinking and simply letting yourself absorb the images before you.” Gallwey argues that every human is encoded with a natural learning process. This process allows babies to walk long before their parents could explain it to them. The key activity of observing a successful outcome with your eyes, ears, and nose is more effective than any technical explanation. I remember watching countless highlights of Shane Battier and Andre Dawkins as a kid- just trying to imitate their exact basketball shots. I would go as far as to open my mouth and scrunch my eyebrows in the same position as their posters on my wall. No one had to explicitly tell me to jump with my legs, position my hands, and flick my wrist; simply observing Battier and Dawkins taught my Self 2 to do it without me realizing. Relating this to career, it’s important to observe those who you aspire to be. In addition to reading books from those at the top, there’s value in being in the room where it happens. This is one reason young professionals should consider starting at large organizations. At Google, one can see how their Senior Directors react to pain, pleasure, choices, and adversity. Talent rubs off, and proximity to leadership is a great way to become a better professional without needing to take a single note. A good coach will encourage their student to find a mentor whom they can observe. Once the observation period ends, the coach should not ask the student what they observed. That’s that trap of Self 1. Rather, the student should immedaitely act and trust that Self 2’s naturally encoded learning will lead to them success. Thinking While Performing “Before hitting the next set of balls, I asked Joan, ‘This time I want you to focus your mind on the seams of the ball. Don’t think about making contact. In fact, don’t try to hit the ball at all.” It’s happened too many times in my golf game; I’d pick up a new, exciting feeling on the driving range, codify those feelings into rules, then enact those rules on the course… only to disastrous results. Creating rigid, conscious rules is a Self 1 exercise that prevents Self 2 from effortless performance. People often misinterpret “thinking” for “performing”. Thus, if you do not think about your newest backswing, you will not do it. However, if you trust the learning process of observing, feeling, and experiencing, you will build a muscle memory that goes beyond any thought. At the beginning of every spring, I would pick up my clubs and play some golf. I always play well in my first couple rounds. And, it used to piss me off! I would think, wow, I must be really bad at practicing if rusty Ben always plays better than golf-every-day Ben. But, I now realize that “rusty” is a poor word. This version of me doesn’t overthink. It is a version that has had time to hibernate and naturally encode all my greatest golf habits (and forget the others). To keep Self 1 from creeping in, Gallwey suggests focusing on something harmless, like the seams of the ball. This keeps Self 1 occupied and lets Self 2 take control. You’re not thinking about what to do with the seams—you’re just acknowledging them. Calm your mind, trust your body. You’re more talented than you think! Competing Against Others “It is the duty of your opponent to create the greatest possible difficulties for you, just as it is yours to try to create obstacles for him. Only by doing this do you give each other the opportunity to find out to what heights each can rise… Instead of hoping your opponent is going to double-fault, you actually wish that he’ll get it in. This desire helps you achieve a better mental state of returning it.” This is a great way to reframe “challenge” as “opportunity.” Whether you’re competing against another person, the environment (a golf course, the stock market), or yourself, pressure is a privilege. If I see a great tennis player on the other side of the net, I ought to smile, as it’s an opportunity to prove to Self 1 that Self 2 is even more awesome than he thinks! I’ll admit, I’ve lost some of my competitive edge since entering the workforce. My competitors are less often other people and more often internal feelings—fear, change, complacency. But I’m starting to see that competitive joy can still be found in these areas too. When I face a difficult situation at work, it’s an opportunity to improve and sharpen my skills. Judging Yourself “Why shouldn’t a beginning player treat his backhand as a loving mother would her child? The trick is to not identify with the backhand. If you view an erratic backhand as a reflection of who you are, you will be upset. But you are not your backhand any more than a parent is his child… Remember that you are not your tennis game. You are not your body. Trust the body to learn and play, as you worst trust another person to do a job… Let the flower grow.” It’s easy to see performance as a reflection of your character or work ethic. A big part of my personality that I’m working on is how negative outcomes in one area of my life tend to impact others. I’ve heard the saying, “would you talk to a friend that way?” and how I should separate my mistakes from my self-worth as a human. This is essentially Gallwey’s advice, although I found his perspective much more optimistic and constructive. First, one must detach the activity from the human. You are not your tennis game. Once you do that, you can see your game for what it is- a living entity that’s filled with potential, secrets, and passion. Go off and explore! That said, I struggle with this idea when it comes to my career. Perhaps I’m too American, but I find it hard to say, “You are not your career,” and mean it. Since college, I’ve expected that my accomplishments, my friends, the places I’d live, and even the women I’d date would spawn from my career and the experiences within it. I think many young professionals feel the same way. This makes detaching from outcomes difficult, and it’s something I still need to think about.

Two days ago, I decided I want to buy my first house. My goal is to purchase it before the summer of 2025. Why are you buying a house? To make money. I see this as an opportunity in a space that many friends and family consider a safe, high-return bet (if done right). When joining Kibu, I took a pay cut in exchange for higher upside, executive responsibilities, and the opportunity to work on a great mission. That said, it’s time to use the money I’ve saved to explore additional revenue streams. Purchasing a home, making renovations, earning cash flow from renters, and watching the home’s value appreciate could be the revenue stream I’ve been looking for! Where are you buying a house? I will be buying a house in my hometown of Pittsburgh, PA. My parents and sister still live there, and we all have a good sense of the “best spots” in the city. I love Pittsburgh, and I can see myself visiting 2-3 times per year—especially with my recent move to NYC. On top of hometown knowledge, Pittsburgh is one of those “best value” cities, often getting acclaimed as one of the most walkable, affordable cities in America. Although I’ve just begun planning, I could see myself purchasing somewhere near my dad, close to a train line and some nightlife, like Mt. Lebanon, Mt. Washington, or maybe the Southside. Can you afford to buy a house? Anyone who’s debt-free, has good credit (720+), and earns a steady income can buy a house. However, factors like intent, location, and risk tolerance will decide if one can actually afford a house. As I said above, I intend to purchase a house for investment purposes. That means the monthly mortgage and operating expenses must be less than the rent income I intend to receive: Net Cash Flow = Total Rental Income − (Operating Expenses + Mortgage Payments) Additionally, I need to determine if I can afford the house at the time of closing. Generally, a lender requires a down payment of ~20% of the home’s purchase price. However, as a first-time homebuyer, that payment can be considerably lower. An FHA loan could allow for a down payment as low as 3.5%, but that comes with added upfront and monthly premiums known as MIPs (Mortgage Insurance Premiums), which I would essentially treat as added mortgage payments. As a rough estimate, homes in Mt. Lebanon and Mt. Washington range from $200k to $500k. Per advice on YouTube, I intend to speak with a local lender in Pittsburgh, evaluate my financials, and be told exactly what I can afford. Who’s going to help you? As a first-time homebuyer, this one makes me the most nervous. Even as I write this blog and browse Zillow, I get feelings of doubt. I need to find trusted mentors and professionals to guide me down the right path. Mentors My dad: I’ll look to my dad, a 40+ year Pittsburgh homeowner, to help search for neighborhoods. My dad has also mentioned he’d be willing to periodically visit the house after it’s purchased, which is immensely valuable for me as an out-of-state buyer. Friends: I have two friends in mind who can share their homebuyer stories. One of them was in a similar position to mine: a new NYC resident who bought a house in his Texas hometown. Another friend is a serial real estate investor. YouTube and ChatGPT: I will lean on all the internet’s free resources to help me get the dumb questions answered. ChatGPT is a game-changer for answering FAQs, as it can contextualize answers to my situation and provide solicit-free advice. Professionals Lender: A good lender will be responsive, transparent, and have a proven track record in first-time home buying. Agent: A good real estate agent will have similar qualities to the lender, with strong connections to inspectors and contractors. What’s your timeline? (Sep-Oct): Speak with a Pittsburgh-based lender and learn what I can afford. (Oct-Jan): Search for properties on Zillow, Redfin, and Craigslist. Perform back-of-the-napkin math on the mortgage, operating expenses, and estimated rent to determine if the house will be cash flow positive. (Jan-Mar): Visit a couple dozen homes in person. Look for patterns in why homes are valued the way they are. (Feb-Apr): Make offers. (Mar-May): Make home inspections. Use the data to negotiate credits or a reduced price on the home. (May-Jul): Renovate the house. Be onsite as often as possible to ensure work is being done in a timely manner. (Jul-Sep): Look for renters. Take professional pictures of the house and post it on rental sites. Profit??