• Opportunities in disguise

    I remember the first time I gave someone a raise. I’ll never forget it. This person was a key player on the team. Someone talented and experienced, that had nonetheless bought into our mission and delivered results. He was a fun person to be around, too. But because we were an early stage startup, we…More

  • Haircuts and leadership

    Today as I was getting my haircut, I noticed a situation that made me think about the role of a leader in an organization. What made today different than any other haircut? Today, the owner of the business was present at the front desk. He was there when I arrived, during my haircut, and as…More

  • What To Do When Your Feedback Doesn’t Land

    An excellent article by Lara Hogan. My favorite part: We’re going to have to lean into the discomfort of this moment here. I’m sorry! It might feel easier to avoid this awkward conversation, or simply trust that the feedback has landed. But moving forward without triple-checking that you’re on the same page wouldn’t be fair…More

  • Launching over and over again

    There’s a huge difference between shipping a product, soft launching, and launching. And there’s no rule that says you can only launch once. It took a fair amount of effort for me to divorce these ideas in my own mind. The novice mindset of “if you build it, they will come” is still one of…More

  • Project to Product and Greatness

    Jessitron writes: Software is not an up-front investment that pays off over its use. Software is an ongoing concern, an intricate piece of a business that needs to evolve if the business is going to. and: The difference between people good at receiving direction and people who generate their own direction, according to Kegan, is…More

  • The robustness principle of human communication

    If you work in software, you may have heard of The Robustness Principle, aka Postel’s Law. It states that when designing software systems, programmers should: Be liberal in what you accept, and conservative in what you send. In software, this means that you should always send data in a format that is as conformant with…More

  • What CTO means to me

    One of my favorite things about the role of CTO is how different the role is at different companies. Early on it basically means technical cofounder or at least first technical team member. As the company grows, it can evolve in either the technical direction or management direction or a hybrid of both. Some CTOs…More

  • Disagree and commit

    Someone once told me that as a member of the executive team at a growing technology startup, whenever there is a Big Decision that must be made, you have three choices: Agree and commit Disagree and commit Don’t let the door hit your ass on the way out Obviously this is a bit tongue-in-cheek, but…More

  • How I make product decisions

    We’re currently on week 14 of Agave, and I wanted to write a little about the product development process inside my brain as Jared and I are working on building the best virtual office in the world for remote teams to have serendipitous interactions. Separate problems/opportunities and solutions It’s such a common mistake to make…More

  • Management Scrutiny

    This, 1000000%: People aren’t paying attention out of any sort of expectation of wisdom – but when someone has an impact on your job, it’s rational and reasonable to analyze them to help your career. However, I find that few new managers are aware of this phenomenon, which can have far-ranging consequences. From Stay SaaSyMore

  • Plato and leadership

    Adrian Wooldridge writes about the ancient wisdom of Plato and how it relates to democracy and society’s classes. The most prescient part of the article for me was: If a society run by educated guardians is the best sort of society, in Plato’s view, a society run by the masses is the worst. Plato conceded…More

  • Incremental improvements and big bets

    I was reading Auren Hoffman’s Step Functions and One-percent Improvements and remembered a key piece of advice we received early at Bloc. I can’t remember who told us, but it was: Every project is either an incremental improvement or a big bet. You need both. I think about this a lot during roadmapping exercises or…More

  • Extrapolating from one number

    I was reading Scott Alexander’s excellent post this morning about why different people got the early coronavirus predictions right and wrong, and one of the things he mentions: The coronavirus killed fewer people than the flu did in January. But it might kill more in February — and unlike the flu, its scope and effects…More

  • Jargon mismatch

    From Boz’s Mission, Strategy, and Tactics: Interestingly, this post is an example of something even more paramount than having a mission: providing a common language for the team to use that everyone understands. Ensuring people use terms consistently isn’t just pedantry, it is potentially critical to scaling execution. I couldn’t agree more emphatically. One of…More

  • “Greatness” by David Marquet

    I try to watch this video at least once a quarter to remind me of how and why great leaders build and run their teams. It’s 10 minutes long and well worth your time. If you liked this, you should read his book, Turn the Ship Around.More

  • On choosing boring technologies

    A reaction / agreement to Choose Boring Technology. I remember a very early argument at Bloc that I’m sure Roshan will remember. It had to do with whether or not we should build our application in Ruby on Rails or some combination of separate frontend and backend tech. Those of you who know me now,…More

  • If You Multitask During Meetings, Your Team Will, Too

    From HBR This has become one of my biggest pet peeves at modern companies. And it is everywhere. Someone calls a meeting and 5 people show up, each carrying a laptop. Maybe you, as the meeting owner, kick things off. But then, I see your eyes drawn to your email inbox. During the meeting. While…More

  • Why I come to work every day

    At our company (and any company) many things change. We add features and enhancements to our products. We may launch new products and kill off old products. In response to market forces, we may find ourselves changing more fundamental things like our business model. Our cash balance changes, and our runway changes. When we raise…More