From Founder to Master Operator

How it started:

In 2015 I became obsessed with a simple question: How do founders get better at their jobs?

I interviewed entrepreneurs, board members, and investors. Person after person responded with confusion, as if the answer was obvious to everyone but me. “It’s the founder’s job to get better, to learn, to mature. Learn fast, or see your company perish.”

There was no training. No formal education. Just trial and expensive error.

It was shocking at first. I wondered if the startup founder could be the one (potentially) highly compensated professional that lacked any kind of real training. Pilots are taught to fly. Teachers are taught to teach. Surgeons are taught to mend. (In fact, imagine if surgeons were treated like founders: “Ok, we know you killed the last one, but we’re sure you’ll figure it out eventually.”)

Was the gap in the ecosystem really this wide?

To answer that question, I examined each of the options a founder might pursue.


The best a founder can hope for in academia is a limited program focusing on prototyping, early customer discovery, and finding a line of sight to product-market fit. Students do not learn how to build an early team, rally toward goals on an impossible timeline, raise capital, or align board members. Nor do they gain the dozens of other skills required to build a sustainable business.


Accelerators consist of 6 months of chaos followed by a demo day. At best, founders attend workshops, sit with part-time advisors, and meet some investors. The typical successful startup requires nearly a decade to reach liquidity. A 6-month pre-seed accelerator barely makes a dent.

Venture Capitalists

Great VCs provide value in 4 ways: governance, strategy, introductions, and capital. Bad VCs cause harm, but I’ve told that story in another post. VCs neither provide training nor safe mentorship. They make money by making good bets. And they would sooner replace an underperforming founder than engage in the heavy lift required to uplevel performance. There has been a great shift to separate strategy from the capital with an increasing number of avenues for founders seeking good advice separate from funding — from peer networking groups to classroom intensives to…


What about the cottage industry of advisors that have populated the startup scene for decades? You know who I’m describing. This is often an accomplished founder who:

1. Is taking a brief break from full-time gigs.

2. Has ample domain knowledge.

3. Is motivated to pay it forward with earlier-stage CEOs.

Unfortunately, the typical hobbyist advisor has no curriculum or pedagogy and, instead, hopes the founder asks the right questions at the right times. Sporadic meetings and pithy anecdotes might be useful; but should not be confused with training.


And of course, there are books, blogs, Twitter threads, and conferences. All can be useful. I certainly have my favorites. But closing the last mile between a written framework and what is happening on the ground is difficult. And most founders lack the space to hunt down, interpret, and implement the right piece of content for every challenge.

The Road to Mastery

For every founder, whether a first-timer with a fresh idea or a veteran operator of a growth-stage business, there is a gap between the operator they are and the one they might become.

Bringing a new idea to the world requires unique thinking.

But building an effective company around that idea benefits from discipline, not improvisation. Goal setting, financial planning, and internal communications are not specific to a domain, geography, or culture. Sales, marketing, people operations, and customer success are functional skills that transcend any specific business. So, what does it mean to be a master operator? To be a master operator means gaining fluency across the gamut.

3 Dimensions of the Master Operator

The 3 Dimensions of the Master Operator are the heart of what we teach at Enjoy the Work. I’ve provided an overview below.

Dimension 1: General Management

Here is the thing people in entrepreneurship don’t want to admit: Most founders don’t know how to run a business. They know how to build a product. Possibly, they know how to win a customer or attract users. But running a business well requires a great deal more than just written code and a sales deck. Such as:

Strategy and goal setting. What has to be true to achieve the next milestone? How best do you codify, disseminate, report, and evaluate targets and progress? And how do you instill these rituals such that feedback loops are rapid and blameless?

Financial planning. How do you master bottom-up and top-down planning and transform your operating model into a living part of your management process? How do you infuse your critical financial targets into the entire company and ensure they remain aligned with changing market conditions?

Internal communications. What is your communication architecture? How do you share knowledge, make decisions, run meetings, and gather feedback?

Capital raising. What amount of capital will unlock the next inflection point in the business? Who are the target investors? What is your fundraising thesis, supporting financial model, objection handling content, and theorized deal structure? What are your diligence materials, and how do you create sufficient scarcity to close the round?

M&A. What sources of inorganic growth might advance the company — whether via the acquisition of an install base, employees, or technology? What is the list of targets? How do you construct a business case and an integration plan to ensure the reality of the acquisition matches the promise?

Hiring. How do you hire not just one person well but many? What are the systems that ensure optimized decisions while maintaining the culture and competence needed to achieve venture-scale returns? What robust onboarding is needed to transform new hires into productive team members with maximum efficiency?

Board management. How do you foster one-on-one investor relationships, understand venture points of view, prepare professional board packages, and run effective board meetings?

Dimension 2: Functional Management

If a startup begins to work, hiring functional leaders is an inevitability. But let’s imagine a first-time founder with an engineering background hiring a VP of Sales. How does the founder know what great looks like? And even if they make the hire, how will they learn to manage that person? The master operator understands deeply the functional responsibilities of each of their direct reports — what goals make sense, what menu of tactics are available, and what great looks like.

Marketing. What’s your brand? How do you market your product, from demand generation to growth to lifecycle? How will you reach customers with the right message at the right time on the right platform? What is your PR strategy? Or how do you convert your best customers into evangelists?

Sales. What’s the sales motion, and do you have a codified playbook by which to scale bottom-of-the-funnel execution across your SDR, pre-sales, and account executive functions? How will you map sales territories, build a reinforcing commission structure, manage the pipeline, and ramp new hires?

Customer Success. How do you keep your existing customers happy? Ensure they succeed at using your product or service. Collect and leverage the right data points. Manage accounts? Do you upsell? Cross-sell? Both?

People Ops. What’s your hiring strategy? How do you attract, develop, and keep top-level talent? How will you compensate your team, recognize high performers and manage low ones? What does your org chart look like? What’s your mission? What’s your vision? What are your values?

Finance. How will you deal with taxes, compliance, industry regulations, insurance, etc.? What is the monthly, quarterly, and annual closing process? How do you build an FP&A function such that annual planning, scenario forecasting, and board reporting are seamless?

Product & Engineering. What’s your product vision to bring something novel to the world? Product strategy to outmaneuver your competition? Or development processes to ensure you ship good code?

Dimension 3: Self Management

Have you met a founder who has endless intellectual capacity but cannot connect with other humans? The founder who lacks empathy, fails to make people feel safe, doesn’t hold himself or others accountable, and more? It’s not enough to know how to build a product and hire a team; the master operator wishes to build a sustainable operation, and that starts with emotional strength.

Accountability. Can you hold yourself and others to their word in a manner that replenishes, rather than depletes, relationships?

Conflict resolution. Can you address hard topics directly and with kindness?

Psychological safety. Do you foster an atmosphere of openness? Do those who work with you share all the news with you, even when it’s negative?

Empathy. Are you able to view the world through the lens of those you serve?

Intuition. Can you hear the quiet voice in your head that lets you know what you really believe?

Feedback. Are you able to shape and share what your people need to hear to improve?

Self-care. Your emotional state follows your physical state. Underslept, poorly nourished, and utterly sedentary won’t let you perform as needed to navigate the dynamism and pressure of an ascending startup.

Where are we now?

The industry still needs more master operators. Startups are the world’s source of innovation, job growth, and economic prosperity. But too often, compelling ideas perish due to inexperienced leadership.

Founders are extraordinary humans. They will turn their imagination into reality. But they don’t have to conjure an org chart. They don’t have to innovate how to run a meeting well. And they certainly don’t need to invent a new form of hiring, financial planning, or capital raising. Those are all skills to be learned.

Founders should invent products. Not how to run the companies. That’s why we founded Enjoy The Work, and it’s why, nearly a decade in, we still enjoy every moment of it.

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