Sachin Rekhi

I was first introduced to Annie Duke's concepts in a recent podcast with Stewart Butterfield interviewing Ben Horowitz and Marc Andreessen on the 10th anniversary of A16Z. In the interview Stewart asks Marc about any mistakes he believed he had made building A16Z. Marc starts off by referring to Annie Duke's work and the concept of resulting, which is the tendency to equate the quality of a decision with the quality of its outcome, which is a risky and incorrect thing to do with any decision that has a probabilistic outcome. And he shares how A16Z has significantly improved the quality of their decision making over the years by focusing on the very process by which they make their investment decisions in the first place.

As someone who deeply values being an infinite learner, I saw an opportunity to improve the quality of my learning cycles from decision making so decided to take Marc's recommendation and read Thinking in Bets by Annie Duke. Annie brings such a fascinating perspective to decision making based on her 20 years as a professional poker player. As someone who has had to make thousands of split-second decisions whose quality determined whether she immediately won or lost tens of thousands of dollars at a time, she's had the opportunity to refine her decision-making approach. And ultimately to apply it to the world of business in her more recent consulting work.

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I recently had the opportunity to join the Product Love podcast to talk about all things product management with Eric Boduch. I spent a fair amount of time detailing my framework for the 3 types of product management roles that exist in the industry, which I affectionately call builders, tuners, and innovators. The builder is probably the most classic product manager. They’re focused on driving the roadmap and building features to serve user needs. They understand how to prioritize feedback, solve real user problems, and deliver delight. On the other hand, tuners try to optimize existing experiences such as monetization or growth flows. Tuners can be likened to growth hackers who focus on metrics and want to move the needle. And finally, when you are bringing a brand new product to market, regardless of whether you are at a startup or at an established tech company, the task requires a unique set of skills as an innovator to discover and reach product/market fit.

I always love reading each new book the Basecamp team publishes as they are inevitably chock-full of unique perspectives that preach an approach to working better that goes against conventional wisdom and established best practices. I don't always agree with every practice they preach, but I absolutely love reflecting upon diverging opinions that challenge my own assumptions. The Basecamp team does a fantastic job of thinking from first principles, questioning the status quo, and coming up with novel practices that they've carefully battle-tested on their own team over the last 15 years of developing Basecamp.

Their latest book, Shape Up by Ryan Singer, delivered another compelling read on effectively managing software projects. The book shares the full software development process that the Basecamp team currently uses across it's 50-person team to build and enhance Basecamp itself. As always, it preaches a uniquely Basecamp way of doing things. Jason Fried says so himself in the foreward:

For one, we’re not into waterfall or agile or scrum. For two, we don’t line walls with Post-it notes. For three, we don’t do daily stand ups, design sprints, development sprints, or anything remotely tied to a metaphor that includes being tired and worn out at the end. No backlogs, no Kanban, no velocity tracking, none of that. We have an entirely different approach. One developed in isolation over nearly 15 years of constant trial and error, taking note, iterating, honing in, and polishing up. We’ve shaped our own way.

While the book covers many aspects of the software development cycle, I wanted to share the three concepts I found most compelling.

One of the mental models that's had a huge impact on my life is the growth mindset. Coined by Carol Dweck in Mindset, the notion is that individuals either see the world through a fixed or a growth mindset.

In a fixed mindset, you believe that your qualities are carved in stone. That your abilities, attitudes, and personality are largely defined by your innate capabilities at birth. This mindset can be quite dangerous as it significantly effects how you see the world. Those with a fixed mindset often ruminate over their problems and setbacks, essentially tormenting themselves with the idea that the setbacks meant they were incompetent or unworthy. It can cause you to transform inevitable failures from an action (I failed) to an identity (I am a failure). Ultimately this view can result in reduced effort in trying to accomplish your goals because the prospect of failing becomes too much to bear.

Alternatively, in a growth mindset, you believe that your basic qualities are things you can cultivate through effort. While we each may start with different temperaments and aptitudes, you believe that experience, training, and personal effort can result in significant improvements in your skills and abilities. People with a growth mindset have a passion for stretching themselves and sticking to it, even (or especially) when it’s not going well. This mindset enables you to continuously grow your skills, evolve yourself, and reach new heights.

Carol Dweck's research makes clear that while your mindset often sets in early in life, there is a meaningful path to upgrading your own mindset from fixed to growth.

While I've been fortunate enough to have a growth mindset from a young age, I've realized over time there are ways to proactively redesign your life to maximize your own growth. Getting the most out of a growth mindset isn't simply about having the belief that you can improve. That's certainly table stakes. But mastery requires being intentional about your own growth: developing the right practices and attitudes to nurture it. I've adopted a variety of practices over the years that have ultimately become essential elements my own growth practice.

I've long found myself unsatisfied with the conventional discourse of what leadership is supposed to look like in Silicon Valley technology companies. These best practices are typically oversimplified into two high-level philosophies on leadership.

The first philosophy is often characterized by first setting an overall vision; then coming up with mutually agreed upon goals, often in the form of objectives and key results (OKRs), and holding teams accountable to those results; and finally delegating and getting out of the way to allow the team to perform. Folks who subscribe to this philosophy often talk about making yourself as redundant as possible as a sign of success in the process. Fred Wilson shares this mentality in how he describes the role of the CEO of a startup:

A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.

In stark contrast to this approach, the second philosophy is exemplified by the leadership style of the late Steve Jobs. It's a benevolent dictator mentality that has the leader at the top leveraging their own incredible and unique abilities, taste, and judgment to call the shots and make the most important decisions. They are often leveraging their teams as the execution arm of their will. And while scaling is the typical challenge to this approach, they solve for it through a maniacal focus on the very few products that really matter. Elon Musk and Mark Zuckerberg are also often described as leaders that exemplify this very leadership philosophy.

These two leadership approaches couldn't be more different from each other. Yet both suffer from serious shortcomings. Given this, I've always been fascinated with alternative or more nuanced approaches to leadership that could potentially provide a better way. Keith Rabois encouraged me to read The Score Takes Care of Itself by the late Bill Walsh to learn about another such way. It turned out to be a fantastic read in which Bill Walsh shares unique insights into his leadership approach from his time as head coach and general manager of the San Francisco 49ers. It provides a compelling model for tech startups today and I wanted to share my three biggest takeaways from it.