Getting out of the cave


In the allegory "The Cave", Plato describes a group of people who have lived chained to the wall of a cave all their lives, facing a blank wall. The people watch shadows projected on the wall from objects passing in front of a fire behind them and give names to these shadows. The shadows are the prisoners' reality, but are not accurate representations of the real world.

As a team building a company, we are this group of prisoners. Our reality is not the shadows on the wall but that what exists outside of the cave. To become successful, it is crucial we get out of the cave. Not just sales and marketing but most roles, especially product and engineering.

We won’t go in depth on networking with peers outside our company, that’s a pretty obvious way of getting out of the cave. This page focuses on two specific ways to get out of the cave: interacting with customers and advisors.

Interacting with customers

“Customers” should be interpreted as current but also potential future customers.

Given we’re focused on making customers badass and use the Jobs To Be Done framework to understand what will make them badass, it follows naturally we should have a deep understanding of what’s blocking (potential) customers from getting their jobs done. No one will benefit from a spray & pray approach.

There are four buckets of “interacting with customers” that each have a different objective. They roughly map to a customer’s journey.


This is us going out into the wild, asking questions and offering our hypothesis to people in the industry (and potentially even outside). A great example of this is the discovery done by Rik around potential go to markets

The objective of discovery is a) to inform ourselves about the current state of reality and b) to stress test our hypotheses and assumptions.


Very often, what people say is not the same as what they do. A lot of knowledge can be gained by watching a person do things, that would never surface in a conversation.

Either on-site or over a call, shadowing is passively watching a person perform their job (i.e. trying to “get their job done”). This can happen at multiple stages of the customer’s journey. Before they’ve ever heard of Awell or seen a demo, shadowing allows us to understand how the current way of getting their job done blocks them from being successful. After they started using Awell, shadowing becomes a powerful tool to understand how our product is enabling or blocking them from extracting full value, and again getting their jobs done but this time with our software.

The objective of shadowing is to gain the knowledge that cannot be gained from conversations.

Collison install

After the founders of Stripe, Patrick & John Collison (so not a collision install):

To gain early users, Stripe’s founders employed a power move now immortalized at YC as “the Collison installation.” While some founders might share an email sign-up link after pitching their company to their peers, the Collisons grabbed potential users’ laptops and set them up with Stripe right then and there.

Any chance we get and where it makes business sense, doing the initial work for our incoming customers accelerates getting to a badass customer. Even if we need to fly to their offices, yank the laptops out of their hands and do it for them, this kind of action leaves nothing to chance when it comes to making a customers successful with our product. Obviously there are gradations and multiple media that can be used, i.e. making a postman collection available, building (part of)) a flow for them based on a Miro board, but nothing beats getting into the same room and doing it for them.


This is the most common form of customer interaction and can span everything from qualitative, off the cuff questions in calls what they like and don’t like about our product, to running Sean Ellis and NPS tests to quantify their moods. Feedback can be requested on our live product but also on our prototypes, product pitches, pricing exercises, marketing messages, you name it.

Given a number in isolation will never provide sufficient view on reality (following the cave allegory, a number from a survey is always a shadow on the wall), we opt for always gaining additional color through conversations rather than just rely on the numbers.

Interacting with advisors

“Advisors” can be coaches or advisors, there is overlap. Only the word advisors is used below but it means both.

All existing knowledge is available in books, podcasts, papers, videos and courses. Then why would we need advisors? The added value is twofold:

  • Advisors accelerate learning as they can pattern match inputs & outputs / outcomes. A book won’t do this for you.

  • Advisors can personalize generic content onto your specific problem - i.e. solve exactly instead of generically.

In other words, the above mentioned content is shadows on the wall. Advisors and coaches allow you to get out of the cave. This is not to say that we shouldn’t be reading, taking courses, listening to podcasts: there is value in there. But advisors and coaches are accelerators which we should always prioritize when we have a question or a challenge.

Learnings from S16 on extracting most from your advisors & coaches

On Oct 5, 2023 Thomas participated in a fireside chat organized by our investors S16. This chat hosted a world class advisor: Elena Verna (currently head of growth at Dropbox, see also her interview with Lenny here) and executive coach: Sherali Karimov (has been executive coach to Miro’s CEO among others). Below are the learnings from this chat:

About knowing when to get advisors

  • It's scary how many people are solving problems that are not actually problems, or their top 3 problems. Prioritize your problems first. This is job 1.

  • Take the time to write down explicitly what your desired outcome is, it will allow you to focus in your interaction with the advisor.

What does a good advisor look like?

  • Someone who knows what awesome looks like in a narrow area / specific problem you're trying to solve is the best kind of advisor.

  • A great advisor guides you through 4 stages:

    • Unconscious incompetence

    • Conscious incompetence

    • Conscious competence

    • Unconscious competence

Best practices

  • At dropbox:

    • Any VP and above gets a mandatory advisor / coach assigned.

    • They see who they can stretch internally before hiring any fulltime new role

  • If you have performance issues or an opportunity for growth, first attract an advisor who has the superpowers you are looking for so they inform you who to hire (and can help hire the right person).

  • What is the superpower you can apply when you work with advisors in order to extract maximum value? Turn from defensiveness into curiosity. Ask "why are you proposing this", "does it apply to use case X as well", "give me examples". You don't HAVE to agree with the advisor as you’re still accountable in your role. It's not a debate with the goal to get to a right answer. Listen, be curious, then it's still your decision.

  • Add advisor to slack channels so they can monitor (sometimes point them to where they need to focus).

  • Come with an agenda: prep questions / problems (duh this sounds obvious but the rush of the startup sometimes leads to a lack of prep, which reduces the value of the interaction).

  • Ask a lot of questions about the why behind what they are advising. Understanding how they tick means you're downloading their expertise and pattern matching into your own brain