Creating artifacts that accelerate your career

How entrepreneurs crystallize their experiences and insights into domain expertise

In the wake of winding down my startup 3 years ago, I was freelancing and dabbling with different side projects. I felt insecure about having just spent over 3 years building a startup, with very little to show for it. 

Some of my side projects were around helping founders with fundraising. I wanted to create something that would show that the past four years hadn’t been a waste – that my experience could be turned into something valuable for others. 

This culminated in spending 100 hours over 5 weeks co-writing a book on seed fundraising for founders called Oversubscribed. At the time, writing the book was a playful attempt to crystallize my experience and insights as a founder into credibility and domain expertise. I wanted to create something as an output of my grueling founder experience that others found useful. 

The book wasn’t a breakout success by book standards – we didn’t make any money from it and we didn’t get any book deals. But it was read by thousands of founders and people liked it. I didn’t have the foresight to realize that I had just created a career artifact that would serve as a major career accelerant. It would open doors to new opportunities, accelerate my trajectory at my next gig, and serve as a foundation for future projects.

First, I was able to leverage that artifact to get a job on the AWS Startup team. The fact that people liked the book gave me credibility during the recruiting process which helped my chances. After joining, when AWS needed someone to create a 1-hour talk on fundraising, I was called upon because of the book. I turned that talk into a workshop which I used to scale my mentoring of startups, doing my workshop over 50 times with over 2,000 founders. I ended up doing my workshop a few times with the On Deck Founders program, leading them to ask me to be a fundraising coach for founders in the program looking to raise seed rounds (and repurposing my workshop into a long-form post on their website). We’re still in the early days of seeing the compounding career returns I’m getting from those 100 hours I spent writing that book 3 years ago.

I’ve seen other entrepreneurs create artifacts – during periods of transition – which have served as career accelerants as well. They don’t just manifest as books – they can be talks, essays, or even side projects. And I’d bet that they didn’t know precisely where those artifacts would take their careers at the time that they created them.

Tara Reed founded Kollecto – a service that helps you find affordable art – in 2014. As a non-technical founder, she built the product herself by stitching together different tools (this is before #NoCode was a thing). As she started to see that Kollecto wouldn’t become a venture-scale business that would demand all of her time, she crystallized her insights and experience into a TEDx talk, Building Apps Without Code. That artifact served as a launchpad for the next stage of her career – she positioned herself as one of the experts in no/low-code tools and founded Apps Without Code, an online school teaching people how to build their own app businesses without writing any code.

Sahil Lavingia founded Gumroad in 2011. After raising $16M from top investors, the company struggled to realize the venture-scale expectations that come with raising that kind of money. Sahil had to pivot to a profitable independent business (including massive layoffs) and ended up buying back shares from their investors, enabling him to build Gumroad the way he wanted, without the venture-scale expectations. This was a unique experience which Sahil crystallized in his viral essay Reflecting on My Failure to Build a Billion-Dollar Company. This essay positioned Sahil as an expert on building startups in more minimalistic ways. He built upon this with another essay two years later, No Meetings, No Deadlines, No Full-Time Employees, and now he has a book being released in October 2021 called The Minimalist Entrepreneur.

Ben Tossell was the Community Lead at Product Hunt from 2015-2017. He saw thousands of projects launch on Product Hunt. When he left Product Hunt to work on his own endeavors, he did a project called 10 startups in 24 hours. Having seen so many “startups” launch on Product Hunt and having an interest in No-code tools, he showed that a surprising variety of products could be built and launched quickly without code. This positioned him as an expert on No-Code tools, propelling him in launching MakerPad, an online learning community helping non-technical folks use no/low-code tools to build projects, run businesses and automate workflows. Makerpad was recently acquired by Zapier, and Ben has started a rolling fund where he invests in no-code/low-code tools, as founders of these tools seek out Ben because of his domain expertise.

This all begs the question: how do we define a career artifact and what makes a good one?

A career artifact is a durable resource that crystallizes insights and experience into domain expertise.  It positions you as an expert, can be used as a credential to open doors for new opportunities, and can serve as a foundation for building additional assets.

In the rest of this post, I’m going to break down this definitions with further explanations, examples, and counterexamples. I’ll surface some of the questions I’d recommend thinking about when creating a career artifact. Before diving in, here’s a cheat sheet of all of the eight questions surfaced:

8 questions to ask when creating a career artifact

Durability

  1. If you went a year without touching the artifact, would it still hold value?

Crystallizes insights and experience into domain expertise

  1. What unique experiences or insights do you have that you can draw upon?

  2. What work will be required to convert these my experiences and insights into domain expertise?

Positions you as an expert

  1. As a result of creating an artifact, how will people describe your expertise?

  2. How will you make sure you get validation from the market or endorsements from other experts in the creation and distribution of this artifact?

  3. What spiky point of view will this artifact represent?

Can be used as a credential to open doors for new opportunities

  1. Would this artifact be something you’d be willing to put in your email signature?

Can serve as a foundation for building additional assets

  1. Would you want to continue building things in the space you’re carving out with this artifact?

Durability

A career artifact should be able to stand the test of time. It should not require maintenance to retain its value. 

This doesn’t mean your perspective can’t change. Even if your perspective changes over the course of a few years, an artifact is a snapshot in time and therefore will always remain an accurate representation of your domain expertise at the time it was created.

For example, I now have a more nuanced point of view about certain elements of fundraising than I had when I wrote Oversubscribed, and the fundraising environment has evolved since I wrote the book 3 years ago. Still, the book remains an accurate guide for fundraising circa 2018, so it still has value. In Tara’s TEDx talk in 2015, she references tools like Bubble, Zapier, and Typeform . While the tools have continued to evolve and I’m sure Tara has a more nuanced point of view on building apps without code, the TEDx talk remains an accurate snapshot in time. I still get messages each week from people reading Oversubscribed, and Tara’s talk has 447K views since it was published 5.5 years ago, with 10% of the comments coming in the past 12 months.

On the other hand, some projects are not durable. For example, side projects which require maintenance rarely endure the test of time. We have busy lives, and if maintenance is required for an artifact to be valuable, there’s a good chance it will wither and die. If you create a job board for healthtech enthusiasts, while it has value and may be able to help you land a job at a healthtech VC, it will only hold its value as long as it’s being maintained. Once abandoned, these temporary side projects lose their value and cannot be used to accelerate your career.

When considering creating a career artifact, make sure it will be durable by asking yourself, “if you went a year without touching this, would it still hold value?”

Crystallizes insights and experience into domain expertise

Good career artifacts are more than just by-products of the work you’ve been doing. They require additional work to crystallize your insights and experience into domain expertise with a strong point of view.

Without the act of reflecting and spending many hours writing an essay, Sahil Lavingna’s experience with Gumroad is just something he experienced. But through the process of turning that experience into an essay for broad distribution and consumption, he was able to convert that lived experience into a strong point of view on entrepreneurial minimalism.

Without putting in the time to create a talk, building an app without code was just something that Tara Reed did – it wasn’t something that could get on stage and talk to other entrepreneurs about. 

Before I set out to write a book on fundraising, I had a lot of good fundraising advice that I would give, but I had blind spots. I wasn’t able to provide comprehensive fundraising advice that was relevant to all founders. It was through the process of writing the book and battle-testing the concepts with founders that I developed expertise. 

The process of creating something that crystallizes your own insights and experiences into an artifact that can be broadly distributed and consumed forces you to develop a strong point of view and domain expertise on the subject.

When thinking about a potential artifact, ask yourself, “what unique experiences or insights do you have that you can draw upon?” and “what work will be required to convert these into domain expertise?”

Positions you as an expert

If you’re able to convert your insights and experience into domain expertise through the creation of an artifact, then surely you’ll be looked at as an expert, right? Not necessarily. 

To be positioned as an expert, your artifact needs to (1) legibly frame your expertise, (2) be validated by the market or endorsed by other experts, and (3) stand out from the crowd.

Legibly frame your expertise

As a result of creating an artifact, how will people describe your expertise? This is a simple question that is often overlooked. In Erik Torenberg’s essay Build Personal Moats, he defines a personal moat as “a competitive advantage specific to you that's not only durable, but compounds over time.” He underscores that a personal moat should be “Legible, in the sense that your expertise should be easy to describe, easy to share, and makes people want to do both for you.”

So one of the first questions you should be asking is “As a result of creating an artifact, how will people describe your expertise?” You should be able to write it out, legibly and concisely. 

Validation or Endorsement

I’ve seen entrepreneurs create artifacts that fail to position themselves as an expert because it doesn’t get validated by the market or endorsed by other experts. It’s one thing to create an artifact – it’s another thing to create an artifact that gets others to view you as an expert.

With Oversubscribed, there was risk that Max and I would write yet another piece of fundraising content – something there’s already more than enough of. Without positive reviews and endorsements from other experts on early stage startups, Max and I would just be a couple of random startup people creating a useless fundraising resource. 

There are a shortcuts to getting validation or endorsement with an artifact. 

  1. Collaborate with other experts on the artifact. Max and I had VCs and other experts on fundraising provide feedback on early drafts of the book and even got their feedback on topics that they felt were underexplored in existing fundraising content. Collaborating with these experts gave us their endorsement right out of the gate. 

  2. Distribute using a platform that serves as an endorsement and has built-in distribution. Tara doing her Building Apps Without Code talk with TEDx Detroit gave her the built-in endorsement and distribution of TED. Her talk is on the TEDx Talk Youtube channel, which has 31.7M subscribers. Creating her artifact with TED gave Tara endorsement and distribution out of the gate which helped her immediately clear the bar for being positioned as an expert.

Ask yourself, “how will you make sure you get validation from the market or endorsements from other experts in the creation and distribution of this artifact?”

Stand out from the crowd

This is probably the most important part of positioning. Frankly, it’s the thing that I did not do well with Oversubscribed. “Early Stage Fundraising” is a pretty generic category of expertise. The value of your artifact is correlated with the uniqueness of your positioning. The framework I like the most for this is Wes Kao’s Spiky Point of View

We live in a noisy world. Whichever industry you’re in, there are thousands of other people like you trying to get noticed.

Unless you distinguish yourself, you’ll never get a chance to show how different you actually are.

To stand out, you need to develop what I call a “spiky” point of view. 

A spiky point of view is a perspective others can disagree with. It’s a belief you feel strongly about and are willing to advocate for. It’s your thesis about topics in your realm of expertise.

While No-code is a hot topic now, at the time when Tara Reed gave her talk, Building Apps Without Code, it was a controversial topic. You can see others vehemently disagree with her talk youtube comments like, “learning to code is better than learning how to control somebody else's widgets on a platform.”

Having a spiky point of view requires conviction and will help you stand out from the crowd and get stronger distribution of your artifact.

So ask yourself, “what spiky point of view will this artifact represent?”

Can be used as a credential to open doors for new opportunities

Assuming your artifact legibly frames your expertise, has validation/endorsement, and stands out from the crowd, the chances are high that it will serve as a credential which can open doors for new opportunities. 

As I was reminded by my exchange with my former boss, my writing a book on fundraising wasn’t what served as a credential to help me get a job at AWS – it was the fact that people liked the book.

In order for an artifact to be used as a credential to open doors, you have to be willing to identify with it. I think of this as the “email signature test.” You have to be willing to link to your artifact in your email signature in order for it to serve as a credential. 

I’m not suggesting that you literally need to link to your artifact in your email signature – you can include it in your Linkedin bio, twitter bio, or personal website instead. But the point holds that you need to be willing to link your professional identity to the artifact. 

By tightly connecting your professional identity with the artifact, you’re able to leverage it as a credential. It will enable you to consistently reinforce with others that you are the creator of the artifact, which will in turn reinforce others’ view of you as a domain expert, which will open new opportunities for you. 

When I would go and meet startups in different accelerators and incubators throughout the US to help them with fundraising, I would reference Oversubscribed to immediately gain credibility. Reinforcing this credential helped me earn trust and opened other doors for me, as different programs started requesting that I show up and help their startups with fundraising. Even when I wasn’t in the room to advocate for myself, people were able to reference the book as my credential.

Ask yourself, “would this artifact be something you’d be willing to put in your email signature?”

Can serve as a foundation for building additional assets

A great career artifact can be repurposed, extended, or built upon. They lead to other projects which can lead to new companies, 

Oversubscribed has been repurposed into a fundraising talk, a fundraising workshop, a long-form blog post, and a cohort-based program for early stage founders.

Tara’s talk on Building an App Without Code led to her starting Apps Without Code.

Sahil built upon his essay with another essay two years later, No Meetings, No Deadlines, No Full-Time Employees, and now he has a book being released in October 2021 called The Minimalist Entrepreneur.

Ben built upon his 10 startup in 24 hours artifact in starting MakerPad, which was recently acquired by Zapier

When creating these career artifacts, it’s hard to predict what additional assets we might build in the future. Without being prescriptive, it’s important to ask ourselves, “would you want to continue building things in the space you’re carving out with this artifact?” If the answer is no, that’s ok – there’s still value that can be derived from the artifact, though it likely has a ceiling. 

But creating an artifact that can serve as a foundation for future projects makes it more than just a career accelerant – it can be a launchpad for the next chapters of your career.