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:
- The founders are interesting / fun / smart / human / you name it
- The team is great
- The culture is amazing
- 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.
- 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.
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!
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):
- Accept their mistakes, talk about them, and learn from them. Even if the issue is sensitive, like firing people. (Reflections from the last 2 years as a founder, First hire to first fire.)
- Are reflective, thoughtful, and persistent people. (How we built a $1m ARR SaaS startup, Year four in review: Overcoming the unexpected.)
- Have very definite, clear values. But, more importantly, stand up to them, even if that means losing revenue. (Saying no to big customers.)
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.
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.
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?
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.
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.)
- Fibery.io Vision v.1: Getting Started
- The Next Wave of Work Management Software
- Augmenting Organizational Intelligence
- Use Networks to Prioritize Product Features
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.
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.
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?
Second, both James and Tim have an extensive README file (one, two) 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.
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?
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.
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.
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!
Perhaps the best thing about this post is how little work it takes to create one. I imagine that collecting the data took some time, but the actual writing (it’s an 11-min read) took no more than a week. A week of work for a candidate magnet of such tremendous power? Sounds like a deal.
P.s. Sarah writes a lot more about their team in her yearly review posts, but I decided not to elaborate on those for the sake of clarity. You can check them out here: year 1, year 2, year 3, and year 4.
Unlike Canny and PostHog’s, Fibery’s About Us page doesn’t reveal much info about each team member. You will find no bios or README files there. But it clearly tells you one thing: the team is a bunch of weirdos. So, if weird is your thing, you’ll be attracted to Fibery like a moth to a flame. (Side note: Fibery managed to clearly explain their vision in one paragraph. This is rare.)
I’ve already mentioned Michael’s Startup Diary monthly blog series. What I didn’t say is that each post communicates something about the team: who did what that month, random Slack posts (links, quotes, tweets, and images), etc. If someone new joined that month, Michael writes a few paragraphs explaining who that person is, where they come from, what they’re going to do at Fibery, and even attaches a photo. Like Chris.
At PostHog, every team member has a well-written, few-paragraphs-long bio and a stylish illustration on the Team section of the PostHog’s Handbook. (Which is a work of art worthy of its own blog post, by the way.) Many team members have their own README files, like the founders do. Check out Lottie Coxon’s, PostHog’s Graphic Designer’s README here, and some others here and here. Even a quick read through these bios and READMEs gives you a good idea of who PostHog has on board.
In addition to bios and READMEs, PostHog has a day-in-life video of Lottie, their graphic designer. It communicates a lot more information about what kind of person she is and how working at PostHog feels like than her bio. I wish they had more of those.
Finally, PostHog’s handbook offers two more sections where candidates can learn even more about the team: Culture and Team structure. All are worth a read, and each tells you something new about the company and the team, nurturing your liking and respect for these people. Definitely worth stealing.
To help candidates understand who they will be working with, we at Wasp write a blog post about each new hire:
The posts are brief enough to be read in one sitting. Yet, they are very informative. Basically, each post is an interview, presented as an article. We hope they give candidates a good idea of who they'll be spending half of their waking time with.
While researchers still argue about the ultimate definition, most of us understand culture as “what working here feels like” and/or “how we do things here.” We also understand how crucial it is for those looking for work. It seems glaringly obvious that startups should work hard on communicating their culture. Yet, most companies don’t. Or, even worse, they flood their websites with meaningless HR fluff, which only scares interesting people away. In short, communicating culture well is another low-hanging fruit waiting to be picked.
Canny does an outstanding job at communicating their culture. The primary tool they employ is, once again, their blog. (Note how multifunctional it is: founders, expertise, team, and now culture.) The posts in the Founder Stories category convey very well what working at Canny feels like. Here are a few examples.
I’ll risk repeating myself, but this post so beautifully explains Canny’s culture that I couldn’t resist. It mentions why and how they work remotely, how they do team retreats (with photos and a video from Lisbon!), and how they had fun together playing weird Zoom games when travel was not an option due to Covid.
Pay attention to the imagery. It communicates a lot more information than any lengthy, elaborate description would. Indeed, a picture is often worth a thousand words.
Instead of saying that “team is our priority” or “we invest in our people,” Sarah shows what they’ve done to support their team.
Again, note how specific the imagery is.
Interestingly, Sarah’s post isn’t framed as “hey we do many team retreats, we’re awesome, come work for us.” If they wrote that, the reader would feel uneasy. They would sense bragging. That’s why the explicit message in the post is what Canny learned doing team retreats, not that they’ve done many. This explicit message, however, implies that they indeed have done many retreats! It sends a message that Canny cares for their employees without explicitly saying so. This is what true mastery looks like.
Although this post describes Sarah and Andrew’s personal nomad experience, Sarah managed to reveal Canny’s culture through it. To do that, she described how the team worked on Canny during those nomad years. She also wrote about their communication struggles, routines, and a lot more. And, again, look at how effectively her seemingly imperfect screenshots and photos transmit the vibe!
While Fibery’s culture is different from Canny’s, they also communicate it well. Their primary tool is a weird, quirky website full of special projects that give you a sense of how they do things at Fibery and what working there feels like.
The first project is Fibery’s /anxiety page. Launched in 2019, it mocks every serious enterprise software out there with puns like “Yet another collaboration tool” as the page title, “Mistake” as a sign-up button text, and, my favorite, “Try—Suffer—Quit” page structure.
One day three years ago, someone submitted this page to Hacker News. The post surged to the top of the frontpage, stayed there for many hours, and got 705 upvotes and 145 comments from people all over the world relating to Fibery’s culture. Why? Because it felt real.
Here’s a glimpse of what people wrote in the comments:
The second special project Fibery did to communicate their culture is the /remote page. It shows what working from home is really like. It’s the funniest thing I’ve ever seen done by a software startup. (Have you ever seen a CEO being licked by a dog?) It also shows how the Fibery team works and even how they use Fibery to build Fibery. Like Canny’s “Lessons from a year of team retreats” blog post, it does so implicitly. A true masterpiece.
Broadly, the whole site screams that Fibery is a place for misfits, rebels, and trouble makers; the place where such people will be valued and will feel like home; the place built around brutal honesty and spicy humor.
The “What (non-)customers say” section is worth a mention. Over my nine years in startups, I haven’t seen a site that a) lists bad customer reviews; and b) uses 💩 emoji as a filter. Again, this is telling. It says a lot about who they are as people: humble, real, and fond of humor.
PostHog’s way of communicating their culture is the most explicit of all four examples, yet very effective. Their primary tool is the PostHog Handbook, which covers virtually every aspect of what working at PostHog feels like: interviews, onboarding, training, management, communication, and even firing. (They call it offboarding.)
The handbook goes all the way up to the high-level strategy, which is very clear. Notably, PostHog’s strategy section not only puts forth ambitious goals but actually explains how exactly the company will get there.
The values section is very specific; perhaps the most specific I’ve ever seen. PostHog does not merely list their values as meaningless abstractions but supports them with evidence. Some values have many paragraphs of examples demonstrating how the team follows them.
In summary, if Canny’s weapon of choice is the blog and Fibery’s is the website, then PostHog’s is definitely the handbook. It’s a work of art.
Unlike Posthog, we at Wasp don’t (yet) have a dedicated Culture page. We are too small for that. But that doesn’t stop us from showing what working at Wasp feels like. We just use different tools.
Our Twitter, blog, and monthly updates abound with memes, GIFs, and hilarious imagery. Plus, we write them in a humorous, lighthearted, easygoing style. By just scrolling through these things for a few minutes, candidates can understand that we aren’t some corporate bros. And if they like working on interesting things while having fun, they won’t help but feel an inkling to reach out.
When you just closed an $80 million Series B or signed Facebook as a customer, communicating progress is easy. You just state these facts. However, most companies need to attract great people way before Series B. In fact, it is these very people who’re going to get you there. As most startups are secretive about how things are going, communicating that things are going somehow — no matter how negligible your progress in contrast to the big guys — becomes quite an advantage. It immediately de-risks the opportunity in the candidate’s eyes. So, if EXPERTISE is about convincing candidates that you know how to build the wings, PROGRESS is about showing them the half-built carcass on your way down. Both are important if you want great people to jump off the cliff with you.
To give candidates a sense that things are moving, that this company is not some long slog but a place where progress is made every day, that they can become a part of something that’s growing and, therefore, can grow themselves, to do all that, Canny does two things.
The first one is their “Year in review” blog post series. Such comprehensive, thoughtful reviews are rare in the startup world. What is even rarer is when these posts span over four consecutive years. It sends a message that the founders are persistent and devoted to making this company successful.
Below are all Canny’s year-in-review posts in a sequential order:
- Year in review: Lessons learned from bootstrapping our SaaS startup
- Year in review: Lessons from our second year of bootstrapping Canny
- Year three in review: Lessons from growing our bootstrapped startup
- Year four in review: Overcoming the unexpected
In addition to year-in-review posts, Sarah writes about hitting notable revenue milestones. Like with yearly reviews, such transparency is rare. It attracts attention, causes liking, and builds trust.
- $0 to $3,500: How we Bootstrapped our SaaS Startup to Ramen Profitability
- $3,5k to $1m: How we built a $1m ARR SaaS startup
- $1m to $2m: How we’re moving our SaaS upmarket to enterprise sales
Finally, Sarah occasionally tweets short summaries of their progress, like this one. These tweets work like ads. Over time, a candidate’s brain fuses them into a broader idea like “Canny is growing” or “Canny is doing well.” Then, once a candidate decides to change jobs, it nudges the candidate to consider Canny.
The most notable thing Fibery does to communicate their progress is the Startup Diary blog posts series written by the founder, Michael, every month, for the past 45 months. It’s the longest series of monthly updates I know. In these posts, Michael honestly shares everything that’s going on with the company: the good, the bad, and the ugly.
Below are just a few examples, selected by me. You can study all Fibery’s monthly updates here.
- #2 Slow September 2018 — Fibery startup progress in September 2018. Slow month with not so many news. First positive feedback. Company name selection.
- #6 Planning Private Beta in January 2019 — Fibery startup progress in January 2019: Private beta goals, selecting a market positioning (hard), apps re-design.
- #10 Burn in May 2019 — Several people burned out, new features are delivered, public release will be sooner (we hope) (despite ill fortune).
- #16 Crazy November 2019 — Fibery 1.0 is silently launched. Silence is hard to keep. HackerNews front page. Twitter madness. 3000 registered accounts.
- #17 Fragmented December 2019 — Public announcements moved to January. +Lena. Tons of feedback. First money! Hype is over. We consider rising a ~$4M round.
- #35 Raised $3.1M in July 2021 — TLDR: We closed $3.1M seed round. Building a second brain for teams. Fibery mission. Building in Public. Automation rules. Documents and Rich Text history.
- #36 20k MRR in August 2021 — Special Startup Diary edition. 20k MRR & 15 new customers! +Chris. +Sales agency. 4 case studies. Airtable integration & notify people action.
- ($30K MRR) #42 Connecting the dots in April 2022 — TLDR: 🇺🇦 Ukrainian war affected our performance. $30K MRR 🐌. 69 reviews in G2 ❤️. Marketing for customer-built products is hard 🥉. 12 customer stories 👻. 2 hours downtime 🥲. New navigation ⛵️. My Space 🔒.
Imagine a candidate who is considering two or more similar startups. Guess what might convince them to go with Fibery? Progress. Or, more exactly, an understanding that Fibery is persistently making progress and, therefore, has a decent chance to become successful. Delivered through these very updates.
Last year, Michael (Fibery’s CEO) started writing year-in-review posts too. I didn’t mention them because there’s just one post for now. You can read his 2021 review here.
The second tool that Fibery employs to share their progress is the /open-startup page. Like monthly updates, it gives candidates a good idea of how the business is doing. This understanding, however, comes from a different source: pure numbers. And numbers often speak louder than words.
In the PostHog’s handbook, they have a page called Story. It succinctly shows the milestones the company has hit so far. For each milestone, they offer a clear and concise explanation of what happened, sometimes no longer than a sentence. As a result, candidates can get a good idea of how things are going in less than a minute. That’s something to aspire to.
Here’s the section titles:
- Jan 2020: The start
- Feb 2020: Launch
- Apr 2020: $3M Seed round
- May 2020: First 1,000 users
- Oct 2020: Billions of events supported
- Nov 2020: Building a platform
- Dec 2020: $9M Series A
- Jun 2021: $15M Series B
- Sep 2021: Product Market fit achieved for PostHog Scale
For each milestone, Matija and Martin (Wasp founders) write a blog post describing not only what they accomplished but also how they did it.
For example, when Wasp got into YC, they didn’t just post the news on Twitter. They wrote a blog about their journey to Y Combinator. It got thousands of views.
Same with fundraising. When Wasp closed a $1.5m seed, Matija documented and shared their fundraising learnings in a blog post. It ended up on the HN frontpage. (Incidentally, this post communicates something important about the founders. It takes persistence to run 250+ meetings in 98 days.)
To keep the momentum, Matija also writes a monthly newsletter. It’s similar to Michael’s Startup Diary in substance, but has a different style. Wasp style. (Which, again, communicates our culture.)
Like PostHog’s Story page, Wasp’s monthly updates give candidates a bird’s eye view over everything that’s happened in the past two years. To anyone interested in connecting the dots, this page is a gem.
The founders are interesting / fun / smart / human / you name it
The team is great
The culture is amazing
The business is doing well
By communicating all these reasons well, what Canny, Fibery, PostHog, and (we hope!) Wasp really end up transmitting is two powerful messages:
- The company is likely to succeed
- Working there will be awesome
These two messages are the real answer to “why people should join your company.” The trick, however, and the reason why I wrote this post, is that you can only transmit them indirectly. You can’t say “our founders are great.” You need to provide candidates with many-many facts about the founders, which their minds will then fuse into this abstract conclusion. Ditto for expertise, team, culture, and progress. Eventually, these first-level abstractions will blend into still broader ones: “the company is likely to succeed” and “working there will be awesome.”
Thus, there’s no single, ultimate answer to “why people should join your company.” There’s only a complex system of concrete, specific units of information from which candidates make the answer themselves. In other words, you can’t teach them why your company is likely to succeed and why working here will be awesome. But you can outline the facts and let them learn for themselves. I hope this post shows how to do that outlining well, and I hope you will apply this knowledge to bring talented people onboard and build great things.