Why your startup is worth joining

How to communicate why your startup is worth joining - 31 min read

Except for a handful of companies who send people to Mars or develop AGI, most startups don’t seem to offer a good reason to join them. You go to their websites and all you see is vague, baseless, overly generic mission-schmission/values-schvalues HR nonsense that supposedly should turn you into a raving fan of whatever they’re doing and make you hit that “Join” button until their servers crash. Well…

Some people think that’s because most startups aren’t worth joining. I disagree. This argument generalizes one’s own reasons for joining a startup onto every other human being out there, which is unlikely to be true. I think most startups, no matter how ordinary, do have a reason to join them; a good reason; even many good reasons — they just fail to communicate them well. They’re like a shy nerd on Tinder with an empty bio and no profile pic: a kind, intelligent, and thoughtful human being who, unfortunately, will be ruthlessly swiped left — not because he’s a bad match but because his profile doesn’t show why he’s a good one.

Visually, this “Tinder profile problem” looks like this:


Now, look what would happen if a startup communicated a bit better. Suddenly, our candidates could see a reason to join. If the reason is good, they might even swipe right.


But most startups have many good reasons to join them. If only they communicated well, the outcome would be something like this:


Now, you’re probably wondering just what exactly those reasons are.

Here’s a rough list:

  1. The founders are interesting / fun / smart / human / you name it
  2. The team is great
  3. The culture is amazing
  4. The business is doing well

However, if you just copy this list and paste it on your jobs page, you will accomplish nothing. The candidates will never believe you. What you need to do instead is to supply them with a system of concretes (facts) from which their minds will form these abstract conclusions.

For example:

  • Instead of declaring that “the founders are reflective, thoughtful, and persistent,” show them how so, like Sarah from Canny does by writing comprehensive year-in-review blog posts for four years in a row.
  • Instead of proclaiming that “the founders are humble and can have fun,” show them how so, like Michael from Fibery did by becoming a hero of this hilarious page. (No businessy founder would ever agree to make this public. Michael did.)
  • Instead of purporting that “the team is great” or “you’ll work alongside very smart people” (God, I hate that one!), show them who exactly those people are, as PostHog does here and Wasp does here and here.

In the rest of the post, I’ll go through the four broad reasons to join a startup one by one and show real-life examples of communicating them well. In the end, I will explain how these four reasons, communicated well, fuse into two compelling messages that will interest any candidate.

One last thing. For the sake of clarity and comprehension, I will write in the second person. Instead of saying “candidates would never believe them,” I will say “you would never believe them.” It’s much easier to read and understand.

Possible reasons why your startup is worth joining, and how to communicate them well#

1. FOUNDERS — or, the founders are interesting / fun / smart / human / you name it#

Most startups have curious, interesting, ambitious, terribly smart founders; the kind most of us would love to work for if we had a chance. Sadly, only a few leverage this asset. In most cases, all you get is a small round pic with a fancy title and a few abstract, high-level sentences that cause no excitement whatsoever. What a shame!

How Canny commmunicates who their founders are#

Founder Stories blog category#

The first notable thing Canny does is the Founder Stories category in their blog. By quickly skimming the posts, you can understand that Sarah and Andrew (the founders):

If they just pinned this list of virtues to their Jobs page, you would never believe them. Instead, Sarah and Andrew show what actions they take, how they work, how they think, how they live — and you make up their own mind about what kind of people Sarah and Andrew are from seeing all that. The difference is enormous.

Note their writing style. They don’t claim to be know-it-alls with titles like “How to bootstrap your startup.” Instead, they write “How we Bootstrapped our SaaS Startup to Ramen Profitability.” They cover only what they know instead of overgeneralizing. This shows both expertise and humility.


Personal Instagram#

The second thing Sarah and Andrew do well to communicate who they are is their Instagram. They don’t post glamorous keynote appearances, as many entrepreneurs do. They share the actual day-to-day working life — both the fun and the struggle. It gives you a good idea of what they’re after in life. (Not keynotes.) That’s why it works, and that’s why people love it.


Side note: Sarah explains how she develops the Canny brand in this post. If you want to build a good one, give it a read. She also wrote about how they attract top talent. You can read it here.

How Fibery communicates who their founder is#

Startup Diary blog post series#

While you can get a pretty good idea of Michael (the founder) from the hilarious “Remote” page Fibery shipped last year, his Startup Diary post series offers an even better insight into his soul. In these monthly posts, Michael honestly shares everything that’s going on with Fibery, including the good, the bad, and the ugly: firing people for poor performance, losing important customers, and failing to reach product-market fit. The fact that he’s already written 45 of those (as of Aug 2022) is also telling. And he’s not a native English speaker. If he can do that, why can’t you?


Crazy challenges#

Besides writing the Startup Diary, Michael also embarks on crazy challenges like writing 100 posts about products. Only a passionate, driven person would commit to such a thing. You cannot help but respect him for it. (Before this challenge, he wrote 100 Medium posts in 100 days in 2018. You can read them here. Just scroll a few screens to reach the old stuff.)


If you look carefully, you’ll notice that Michael’s thinking about building a company is different from Sarah’s. For example, he despises the gentle, soothing “Oh don’t worry that it didn’t work out; you did such a good work!” approach, which is ubiquitous in the modern startup world. Instead, he states that dissatisfaction leads to progress, referring to the famous “Not quite my tempo” scene from Whiplash. Does that make you like him more than Sarah?

It depends. If you believe that being soft and balanced is better, you’ll go with Sarah; if you believe that real progress comes only from working yourself to the bone, you’ll go with Michael (or Elon). The important thing is that both founders have their own, unique viewpoints of how things should be done, and that they communicate these viewpoints as-is instead of chopping their legs off to fit the latest Procrustean fad.

In-depth, original blog posts about the industry#

Some entrepreneurs say that doing a startup is like “jumping off a cliff and building your wings on the way down.” Some of it might be true. But if you want reasonable people to jump with you, you better tell them that you have a degree in engineering and know how to assemble wings in a free fall. Otherwise, the only team you’ll recruit is a suicide squad looking for a splashy hit.

To communicate his expertise, Michael writes in-depth, original, theoretical posts about the nature of knowledge management and organizational productivity. These posts are gems, both literally and metaphorically. (They’re filed under the Gems category in the Fibery blog.)

For example:

After reading these articles, you understand not only that Michael really knows how to build wings while falling off the cliff, but that he has already jumped a few times. (Prior to Fibery, Michael had worked on knowledge management for more than a decade. He also had built a successful project management software, Targetprocess.) You know that he’s an expert who can be trusted.

Interestingly, even though Michael writes differently from Sarah, they both leverage what they’re good at. Sarah does not try to produce treatises on software development philosophy, and Michael doesn’t gush out with his personal learnings from building a startup. That, I think, is the right way to do it.

How PostHog communicates who their founders are#

PostHog’s founders James and Tim don’t write 100 posts in 100 days or run a personal Instagram. But they’ve come up with something else to communicate what kind of people they are. And it’s something unique.

Well-written, concise bio#

First, both founders have decent profiles in the company handbook. These bios are short, clear, and humane. They’re also very specific. Where else have you seen the name of the CEO’s cat?


Personal README files#

Second, both James and Tim have an extensive README file (onetwo) on how to work with them. These files give you an insight into their productivity habits, interests, and quirks. In fact, after reading them, you will likely have a better idea of the founders than you’d usually get from working at a company for a month!

For instance, James’s file has sections like:

  • Short bio. Includes very specific details like: “I tend to work 9am to 5pm with an hour for lunch, then I have a gap to have dinner with my family, then 9pm to around 11pm ish.”
  • Very clear areas of responsibility. No need to wonder what the hell the CEO is doing anymore!
  • Quirks. These are remarkably humble and open-minded, like:
    • “If I haven’t responded to something that you’ve sent me, that’s probably because I’ve read it and don’t feel particularly strongly - so just make a call on what to do if you don’t hear back in a reasonable time frame.”
    • “I’m a little disorganized. I compensate for this by making sure the teams I work on have this skill. Often I think this actually helps me prioritize the things that really matter.”
    • Explaining these quirks is an ingenious move. Besides explaining how to work with James, this section communicates that he’s profoundly self-aware and willing to accept and leverage his weaknesses. These qualities are very rare and incredibly valuable.
  • What I value. In stark contrast to most HR nonsense, these values are very clear, very specific, and written in English rather than HRese. (I just came up with this term: it means “legalese but for HR.”) Here are two examples:
    • “Proactivity. Do not ask me for permission to do things - I wouldn’t have hired you if I didn’t trust you. I’d rather 9 things get done well and 1 thing I disagree with than we don’t get anything done at all.”
    • “Directness impresses me. If you don’t like something please just say so. It makes for much healthier relationships.”

In addition to that, there’s also: How I can help you, How you can help me, My goals until end December 2022 (very specific!), Personal strategy, Execution todo (including “1 bike ride a week”!) and Archived todo.

In summary, this README page is a gem. I wish more founders had them.


How we at Wasp communicate who our founders are#

“Who we are” section of every job description page#

Matija and Martin (the founders of Wasp) embedded a concise description of who they are right into each job description page in Notion. They knew that this is the first company artifact many candidates will see. So they saved candidates time and effort on digging up who the hell started Wasp.

Note the language and substance of this list. When you read it, you immediately get a sense of who Matija and Martin are as people — fun, easygoing, no-corporate-bullshit kinda guys. Now imagine it said something “more normal,” like: “The company was founded by seasoned entrepreneurs…” What impression would that make?


2. TEAM — or, the team is great#

It is startling how little most startups tell you about their teams. Often all you get is a chessboard of faces and titles, which gives you no idea who these people are as people or how working with them will feel like. Given how crucial a reason “great team” is for most candidates, improving how you communicate it seems like a low-hanging fruit.

How Canny communicates who is on their team#

Decent team page#

The Canny’s difference starts with a team page. It has a dense summary of who each team member is as a person and includes high-quality, lively photos of everybody.


Look how specific those bios are. In most cases, all you get here is a generic “developer” or “marketer” without any personal details. Bios of robots, not people. No wonder nothing comes to mind, except perhaps for Agent Smith. But Canny’s bios are different. When you read them, you can actually imagine the person! They’re Neos in the world of Smiths.

Remarkable “Why work at Canny” blog post#

From there, it gets only better. Canny’s chief weapon for explaining their team is a blog post, the “Why work at Canny” blog post. Sarah wrote it back in the summer of 2021. It is full of quotes from team members and photos of their workdays and vacations. Real photos of real people. No wonder the comments section under the post abounds with raving fans willing to join the team straight away!