Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.

If you’re in the middle of en entrepreneurial career or want to start something down the road, consider subscribing:

Entrepreneurship is a skill, not a switch to flip

I get upset when people who are currently not doing anything entrepreneurial say that they want to start a company in the future. 

It’s the equivalent of me spending most of my time playing basketball growing up, never having picked up a guitar, and saying that I wanted to be a lead guitarist some day. 

Being an entrepreneur isn’t a switch you can flip – it’s a skill. At any point in a career, entrepreneurial skills are either non-existent, being strengthened, or atrophying. But founding a company isn’t the only way to build entrepreneurial skills.

Recently, I interviewed Maya Baratz Jordan, the CEO of Founder Factory New York, a venture studio and accelerator that recruits founders to build startups at the idea stage (more to come on that interview). When deciding which founders to bet on, Maya said they don’t necessarily need to have a founder background, but she asks herself, “Can this person go from zero to one? Do they have a track record of being able to build something from nothing?”

This evaluation boils down to a founder’s zero-to-one entrepreneurial skills. These skills are a little different from functional skills like product marketing, product management, engineering, financial modeling, interviewing, and everything in between. These functional skills are great and are generally useful. Assuming you get past the zero-to-one stage, they are really valuable in the later stages of building a company.

But zero-to-one-skills are different. Zero-to-one skills take those functional skills and apply them to the unique challenges of building something from nothing. How do you build a product people want? How can you get people to invest their time and energy when there’s little certainty that your idea will work? How do you get early customers? How do you give investors confidence in what you’re building when there’s so much uncertainty?

Often functional skills honed at bigger companies can be too heavy-handed for the speed that is required at the zero-to-one stage. For example, I’ve seen new entrepreneurs with finance backgrounds create financial models for their pre-seed startups that are way too complex and detailed, when at the pre-seed stage the important thing about a financial model is that it shows the assumptions around key business drivers. Similarly, being an engineer at a FAANG company may teach an engineer how to deal with back-end engineering challenges at scale, but it doesn’t provide the skills required to build a full-stack web app in a weekend using modern development frameworks. At Amazon, I’m developing some invaluable skills about goal-setting, operations, interviewing, and more. But if I tried to apply those skills directly to building something new without distilling them down to the unique needs of the zero-to-one stage, applying those skills as-is would slow me down.

On the other hand, deep functional skills are sometimes not enough to move quickly at the zero-to-one stage. An aspiring entrepreneur who was an A+ growth-stage product manager is going to be a lot slower at the zero-to-one stage than a B- growth-stage product manager who is skilled at creating product MVPs with no-code solutions and a little javascript.

Being a good founder requires breadth of zero-to-one skills with a few zero-to-one superpowers. To put another way, a good founder should be T-shaped with zero-to-one skills (even better to be double-T-shaped. And that doesn’t necessarily require a founder background.

The concept of T-shaped skills, or T-shaped persons is a metaphor used in job recruitment to describe the abilities of persons in the workforce. The vertical bar on the letter T represents the depth of related skills and expertise in a single field, whereas the horizontal bar is the ability to collaborate across disciplines with experts in other areas and to apply knowledge in areas of expertise other than one's own.

When building a startup, developing entrepreneurial skills happens through survival. It’s like being thrown into the deep end of the pool – you’ll either figure out how to swim or drown.

But building an entrepreneurial career includes periods of time when we’re not building startups – but that doesn’t mean we can’t build entrepreneurial skills during those times. We should always be in pursuit of being T-shaped with zero-to-one skills.

When not working on a startup, there are two ways I’ve observed that can develop zero-to-one skills.

1. Convert functional skills into zero-to-one skills through side projects and startup advising

2. Orient your day job so that you’re working on zero-to-one challenges

Convert functional skills into zero-to-one skills through side projects and startup advising

If you have functional skills from a day job, it’s hard to convert them to zero-to-one skills without anything forcing you to do it. This is where working on side projects or advising startups can be helpful.

Have product management skills? Work on a side project where you are trying to ship a product to customers. You will need to harness your product management skills while forcing you to learn how to build a v1 of a product using Webflow, Zapier, Airtable, and Bubble.

Have expertise in interviewing and hiring? Advise a startup that’s making it’s first five hires on how to set up an interview process that’s reflective of the company’s culture. It will force you to contextualize the your interviewing and hiring skills to the zero-to-one phase.

Have a strong finance background? Help a startup with their financial model and learn how to model a business when you have big assumptions and lots of uncertainty.

These side projects and advising can help convert these functional skills into zero-to-one skills.

Orient your day job so that you’re working on zero-to-one challenges

Even if you work for a big company, having a job where you’re owning the launch a new product, development a new program, or the creation of a new team – positions you to develop zero-to-one skills.

While these pursuits can’t fully compare to the experience of building something from nothing, they still build some of the muscles that you would need when starting something from scatch.

Even if your core job isn’t inherently entrepreneurial, there are usually some ways you could take on special projects that would give you entrepreneurial reps. If that’s not possible, then you’re going to need to get your entrepreneurial exercise through side projects and advising. If your day job doesn’t give you enough bandwidth to do that either, then you probably need to find a different day job if you actually want to be an entrepreneur.

If you want to start a company in the future, you should be finding ways to get entrepreneurial reps now – no matter how small – whether it be doing entrepreneurial things in your day job, advising startups, or getting reps through a side project. It’s like if I wanted to become a Michelin star chef – in a perfect world, I would get an apprenticeship with one. But given that’s near impossible, at a bare minimum I should start cooking for myself. That way I’d have something good to talk to a more experienced chef about.