I love Paul Graham’s writing. Hackers and Painters is one of my favorite books of all time. Graham’s thoughts on art and science resonates with me as a designer who studied fine art. The internet broke when the long-time Silicon Valley investor wrote about Founder Mode. There’s been a shift in tech’s factory reset moment during the past few years. The professional management class is getting slashed with the reduction in workforce and the advancement of AI capabilities. Graham’s essay references a talk Airbnb CEO Brian Chesky about Founder Mode vs. Manager Mode.

As always, the internet had a lot of opinions that obviously have to be binary and polarizing towards one direction; classic Silicon Valley hopping on bandwagons. My critique is not Graham’s writing. In fact, he’s right. What’s wild to me is management somehow got conflated to professional management consulting. More accurately, it’s BCG Mode, not Manager Mode. Instead of picking sides, I’m going to propose a different mode.

Operator Mode.

While we talk about founders and C Suite professional managers, the majority of people working at companies are operators. Tech loves adopting words from the military. An operator is someone who…well, operates—plans and executes. Above all else, I consider myself a company operator (who comes from a design background). In this issue, I’ll share how I think of my role helping founders in running their companies.

Operators that add value

In my experience, there are two primary regrets founders have. The first is raising too much money that results in higher demands from the board. After that, it’s building a leadership team from a professional management class. Both result in the founder losing control and getting tucked in a corner as a Chief Strategy Officer or an honorary title.

It sucks to see that happen. Instead, founders are better equipped to find operators that add value to their needs. There are three core areas I believe are most valuable for founders: managers with strong craft, expansive experience, and scale the mission

1) Craft-oriented managers

The concept of professional managers is the biggest mistake. A professional manager is perceived as someone who is hands off, focuses on administration of management, and a master bullshitter. Trust me, these people exist and it's true. Let me ask you a question. As a designer, how would you feel as a designer if the person that has authority over your job has a degree in Design Management but has never been a designer? Imagine an army general who has never seen combat, only studying philosophy and tactics. In my opinion, that's not management.

Most direct reports don't expect their manager to be the best designer on the team, but need to know at one point they were in their career. In order to grow in your craft, one of the top performance indicators in every career ladder, you need someone who knows the craft to elevate yours.

Founders don't need professional managers. They need strong craftspeople who know how to manager. From first-line manager to executive, the best managers are the one who are in the role to scale the craft, not something self-serving.

Whether it's being the founding designer or needing to fill gaps with team churn, the craft-oriented manager has no problem rolling up their sleeves.

2) Expansive experience for the company

An operator brings their experience to expand what the startup is capable of. That is the value of bringing someone in. It might be hiring a sales leader to build out a team as the startup expands into the Enterprise. Perhaps the company is about to IPO and needs a CFO who has repeated experience in this. The one thing an experienced operator cannot do joining a startup is living through the past experience of the company’s existence. This is why expansive experience is the biggest value add for startups growing; helping the founder get to where they want to be.

3) Scales the culture

The last one might be the most important. Operator Mode is scaling the culture of the company, not destroying it. When I decide to join a company, I make sure I’m aligned with the culture and values of the company. It’s impossible to align 100%, but I understand it’s part of my job to scale the culture, so I better be on board with it.

When good operators join companies, they transform the culture for the positive. I only join companies where the culture and mission resonates with me deeply because I feel it's my responsibility to help grow it. I'll never have the same influence as the founder, and that's precisely the point. What's important is for them to have other people they trust to scale the culture, not constantly combat it.

My belief is this doesn't mean to blindly execute without question. In fact, the best mission-driven operators will challenge founders on the hardest parts and hold them accountable.

Leading while in Operator Mode

The goal of an experienced operator is to not be a professional manager. The purpose is to help the founder achieve the vision, hopefully with a desired outcome for everyone at the company. It's difficult to achieve both, but that should be the motivation. Let me share three areas I focus on to help founders and why I think they want me in the first place.

Filling founder gaps

Operator Mode is about filling the gaps of the founder, not replacing them. I remember talking to a former colleague at Replit. One of the main reasons we joined was to work with an inspiring founder like Amjad; give him the amplification (but also counter-balances) to be the best founder possible. The goal is not to silence founders but make them better.

The responsibility in Operator Mode is to find areas you can take over for the founder to be more effective. Most pure founders don’t love managing, and they need managers they can entrust to look over the things they care about. I find the duty of an experienced operator to a founder as a crucial one. Founders have been grinding and putting their heart and soul into their company, and now they entrust you with it.

Scaling the entrepreneurial spirit

When it comes to entrepreneurship at scale, there is nobody who personifies that than Claire Vo. The CPO of LaunchDarkly's philosophy is she joins company to help inject innovation. She reminds teams how to work like a startup and not to be a beauracraticprofessional management machine. Vo is in the weeds by reviewing designs, getting into the work, and even building Chat PRD on her own time. Having a leader who builds and stays close to the craft is the only way they can help you grow. I still design, craft prototypes, and conduct research. The only difference is they serve a different purpose: to guide, invoke ideas, and stay sharp with the tools.

Operator Mode is leading in executing your craft

Whether a founder, operator, or executive, the goal is leading towards shared outcomes; fulfilling the mission while leading a great exit. Your craft may come in many forms. It might be design or engineering. It might be business growth or recruiting. Good managers know how to right size process and scaling. Despite their abundant experience, they’ll start in first principles to devise what’s needed, not blindly run a play book. The balance of craft and management is why I continue loving Operator Mode.

Hyperlinks + notes

A collection of references for this post, updates, and weekly reads.

• OpenAI launched o1 (Strawberry)

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