Startup Divorce: Six Conversations To Have With Your Cofounder Before You Go Into Business

Shortly after the controversy over Tinder first hit the news I was sitting with a group of former and current founders having lunch. There was an interesting juxtaposition between the way we viewed our own experiences with cofounders and the way we viewed Whitney Wolfe’s situation. Each one of us condemned the stripping of Wolfe’s cofounder status and the diminishment of her role in the company’s success. However, when it came to our own departed cofounders each one also admitted to wanting to figure out a way to seize back equity and rewrite the company history.

Working with a cofounder is like getting married, and breaking up with a cofounder is exactly like getting divorced. It is not fun. VCs and startup gurus talk a lot about the importance of team and cofounder dating, but very few people give specific advice about what you should be looking for. How do you know when you have a solid match? How do you find the red flags before equity is divided up?

For the most part my experience with cofounders has been overwhelmingly positive, but even within that sample there were some red flags I ignored that came back to bite me in the ass later on.

Here are six conversations you should have with your cofounder before you tie the knot:

Ask them how they would want to exit in a perfect world

You’re thinking IPO, they’re thinking acquire. In the end you might not get either. It may not matter, but the two goals have completely different timetables and often require completely different strategies.

Ask them where they see themselves in five years (no really)

After a year, your startup will have burned through most of its buzz. Tech blogs won’t really care if you’re killing it, they want shiny new products to write about. After three years if you’re not rolling around in a giant pile of cash everyone assumes your dead, broke and humiliated by your failure. Yet the reality of startups is that they take years of long, hard work. A cofounder who sees himself as only being a cofounder for two or three years is going to be trouble well before the company’s first birthday.

Pick something that fits their role and ask them how they would set it up

This isn’t about quizzing your cofounder, it’s about seeing how well they can explain things to you and whether they are aware of the consequences of the choices they would recommend. When you start a startup there’s a lot that needs to be setup and a lot of established companies willing to throw free accounts and credits at you. If your cofounder leaves, the remaining cofounders need to understand the terms of those freebies, when do they run out, how much will they cost when they do?

Give your cofounder time to research a full and complete answer to this, but press for details. If they don’t realize that you’ll have to file a change with the state to remove a register agent (a common trick used by companies offering cheap incorporation services) that could create a problem later on.

Pick a topic specific to what role your cofounder will be playing. If a technical one, ask about server setup. If a business role, ask about taxes. If a marketing role, ask about social media.

Ask them about their past jobs and startups

It’s not about qualifications, it’s about interests. Do they seem to jump from trend to trend, more concerned with striking it big than with following their passion? It’s easier to weather the stress of startup land when you love what you’re building. The number of sacrifices you’re willing to make increases and the burdens of startup life seem less demoralizing. When you’ve chosen your idea based on an assumption of what will be popular, popularity becomes the glue holding the team together.

Fair weather cofounders are the first to screw you over and the first to fight for more equity if the startup takes off.

Could they live on $1,000 a month? How close could they get to that level?

Would they move to Detroit? Live with their parents? Dumpster dive for food? It’s not necessarily important that they do any of these things, but understanding what cofounders consider essentials is a really good indicator of how long they’ll last. A cofounder who isn’t willing to drink tap water and has to live in certain trendy neighborhoods is going to be under way more pressure than one who considers those things expendable.

Also worthwhile asking them if they’ve ever actually cut back to that level. We all say we’re going to budget better just before we splurge.

Do they have any skills they can leverage to bootstrap comfortably? What about passive streams of income?

You will in all likelihood get to the point where your personal financial situation is negatively affecting the company. It’s not necessarily because of something you did wrong. Opportunities cost money. Here’s what happened with Exversion: YC threw us a little cash to fly in for our interview, but no where near enough to cover costs of the journey. TechCrunch insisted we fly out to SF for rehearsals in order to participate in Battlefield in Berlin. The Open Data Coalition offered us a free booth at their government conference, but we had to get to DC on our own.

I needed a few hundred dollars a month to balance things out, so I went back to teaching ESL (something I had done while traveling around Europe years before).

Having a skill or a resource that can provide injections of cash if needed is really useful. It can be the difference between having to leave the company or not.

If your cofounder says he can always freelance, press him on the specifics of contracts. The nice thing about freelance teaching is that classes have a definite start time and a definite end time. We agreed exactly how much time I would spend on that in advance and it would be extremely difficult to modify those plans.

However, working freelance for other startups or small businesses is different. They act like they own you, wanting you to be on call 24/7, changing project goals and specs on a whim, setting new last-minute deadlines. Add to that the additional work of finding clients, writing proposals, pitching them, negotiating terms, chasing after them for payment … freelance work can and will take over your life

In the end do you really need a cofounder?

No cofounder is always a better choice than a bad cofounder. Bad cofounders can do a lot of damage, often when the startup is the most vulnerable. At the same time, the existence of cofounders is used as an easy filter for VCs and incubators and I suppose that makes a degree of sense. If you can’t convince one person of your product how on Earth will you convince millions?

Analytics Battle: Hacker News -vs- Product Hunt

Product Hunt has emerged as tech’s new darling. All the power of Hacker News, but more curated, posts about the minutiae of programming languages, science and math stripped out in favor of showcasing the best technical projects.

As with all platforms of scale, the larger Hacker News became the more specific the romanticized expectations of it became. Burning idols are always en vogue. So one wonders how much of Product Hunt’s buzz is related to the effectiveness of the site itself, and how much does Product Hunt benefit from disaffected hackers flocking to something shiny and bursting with seemingly endless goodies.

I’ve been on the top of Hacker News a couple of times, and this week Exversion hit the front page of Product Hunt. I’m now in the rather unique position of talking about the impact of both. Not a lot of people can say that.

So … how do they compare?

In terms of pure eyes on the page, the number one position on Hacker News will yield about 1,500 to 2,000 uniques. If that number seems a little low, it’s because the posts that tend to do best on Hacker News are blog posts, code repos and news articles. So you end up driving traffic to your site through another vehicle, inevitably losing some traffic along the way.

Just because a post linking your baby does well on Hacker News, doesn’t necessarily mean you’ll see a significant boost in traffic. My first number one was directly about my experiences getting over my biases against my cofounders and that translated into a lot of interest in what we were building. My second number one was a review of a startup conference. It yielded only about 300 uniques.

By contrast, Product Hunt put 700 unique eyeballs on the screen, much more than a off-topic blog post but much less than a more relevant top HN post. However, while Hacker News hits you with traffic all at once, Product Hunt visitors show up gradually over the course of several days.

Personally, I prefer a couple days of boosted traffic over a spike that only lasts a few hours, but I guess that’s a matter of opinion.


But thousands of visitors who only stay seconds isn’t really that valuable. Obviously you want visitors who browse around, sign up for an account, stay for a while. Here it was no contest. The average Product Hunter stayed on Exversion for 10 to 20 seconds. The average Hacker News reader stays close to 2 mins

WINNER: Hacker News

And here’s where things get interesting, During the rush of new traffic produced by Hacker News returning visitors stayed around 5%. With Product Hunt returning visitors started off at 4% and climbed steadily to 10%. So visitors don’t stay as long initially, but they come back with greater frequency.

WINNER: Product Hunt

Viral Impact
Our first day on Product Hunt we had 300+ direct referrals, and 200+ indirect ones. Indirect referrals come from twitter bots and scrapers that harvest data from Product Hunt and redistribute it in order to boost their own content and activity levels. Get on the top of Product Hunt or Hacker News and these outlets will also pick up your link.

Sites scraping Product Hunt include Panda and The Scoop. Site scraping Hacker News also include Panda and The Scoop, but a wide variety of Twitter accounts attempting to narrow down the firehose.

And here is where the nature of Hacker News gives Product Hunt a distinct advantage: getting to the top of Hacker News is a real challenge. Staying at the top is practically unhackable. Things drop off fast and are engineered to drop off even faster depending on who you displease. Different karma levels unlock more features, specifically flagging and downvoting. There’s a rumor that if a YC-alum downvotes your post it drops immediately to the second page no matter what.

Whatever the case, the fact of the matter is during peak hours your post has only about twenty minutes to break into the top page. Once there it will start to drop as soon as the activity around it starts to wane. Realistically you’re looking at three~four hours of top quality time. If you hit a nerve you might be able to stay at number one the entire day, but rarely if ever do posts stay on the front page more than twenty-four hours.

Product Hunt, by comparison, basically freezes the top 10 every day and displays links by day. So content picked up by syndicators is much more valuable, because it sticks around longer whereas Hacker News can be more of a flash in the pan.

Furthermore, if your startup rates high enough you get featured in Product Hunt’s mailing list, driving an extra spike of traffic later in the week.

WINNER: Product Hunt

You can really only be posted to Product Hunt once. I actually didn’t submit Exversion at all, so while I was happy someone else liked my work enough to throw it up, I was also disappointed that we were up before we had finished planned changes to the main page designed to more intuitively explain what we’re about. The redesign of the front page is a big project we’ve been devoting a lot of time and energy too, and a feature on Product Hunt would have been a lovely cherry on top of that accomplishment, but que sera~

Hacker News, on the other hand, offers infinite opportunities to put yourself in front of new visitors. Just keep blogging and keep submitting. Even posts that barely manage a single upvote tend to yield 40~60 new visitors before they crash. Totally worth it when you figure that submitting is free and you would write the blog post anyway.

WINNER: Hacker News

Conclusions: Breaking off HN niches makes sense
I love HN. However I rarely if ever read it anymore. HN is a firehose of content that simply never ends and barely slows down. Even during off hours there is always new stuff to look at. You could literally spend your entire day reading HN. That’s the fatal flaw for them: the smartest hackers would rather spent all their time hacking, not reading Hacker News.

So I filter Hacker News by topic and break the week’s posts into digests (PS – if you’re into data you can subscribe to these digests here), but still there’s always FOMO. No algorithm is perfect.

Sites like Product Hunt make a lot of sense because they keep good stuff from falling through the cracks. However even this most promising spin off doesn’t come close to generating the traffic of the fire hose. On the other hand, Product Hunt has succeeded where many other “Hacker News for X” attempts have failed because it refines the methodology of HN to fit its own purposes. Multiday boosts in traffic are much preferable to insane fleeting spikes. Visitors who come back a third and fourth time are gold.

All the numbers here reflect my own experiences. They are influenced by Exversion’s unique worts and complications. But I feel confident in saying that the primary difference between the two platforms is that Hacker News will send you traffic, Product Hunt will build traffic.

Building SEO Link Backs Through Github Pull Requests

Continuing our theme of being as evil as possible: you can now import data from Github into Exversion.

First let me say that I love Github. It is a hacker’s paradise and the perfect platform for what it is actually designed to do: share code. But lately Github has started pushing the idea that Github is an appropriate platform for everything from novels, to tutorials, to datasets. And while I’ve seen some truly brilliant ways of arranging a repository to do chapter by chapter instruction, the problem with releasing data on Github is that the same structures that make Github the most efficient solution for hosting code makes it a frustrating and inefficient solution for hosting data.

Nevertheless people do just dump data on Github, dump it there and hope that other people will actually use it. More and more people are dumping data others have already cleaned in exactly the same way on the same platform. If they could find the data on Github in the first place they could have spent their time building something else.

The question for us became how do we turn this into an advantage?

Time to come clean: I did not originally build the ability to import from Github for users. I built it as part of the admin dashboard.

I kept finding interesting data lost and ignored on Github. I kept downloading these files, creating data repos for them and uploading them to Exversion. It was satisfying… a bit like a treasure hunt, but it took up a lot of time. As a hacker when you do the same thing enough times, knowing that you are going to do it many more times in the future, you begin to think seriously about automating it.

The Great Scavenger Hunt: Finding Data on Github

Unless you’re linked to it directly or know the organization/person releasing it, finding data on Github is a pain in the ass. Github search does the reasonable thing and weights their search results by repo activity, however the overwhelming majority of their community is interested in code, not data. If you’re searching for something like Ebola data, the right repo pops up immediately. But if you want something like flight data most of what comes up on Github are apps and pet projects where the word “flight” appears in the title or the description.

Github allows you to search by filetype, which is useful, but will assume you want to query inside files. In other words the query “flights extension:csv” will return csv files with the word “flights” in them (or in the file name) and not repositories that match flights and have csv files. You cannot run a filetype filter without a search query.

So once again, even if Github was the perfect solution for hosting data (which it is not) it can be very difficult to find the data that’s up there. We can’t harvest the data from Github if we can’t find it on Github. This was our first problem.

Luckily there is a service that can search Github and find all the csv files in public repositories. It can even filter it by time period so that every day we have a timely listing of new data to steal.

It’s called Google 🙂

Link Building Through Pull Request

Once I knew where the files I wanted were, importing was pretty easy. Github follows nice, orderly, predictable url patterns. I could download the raw csv file, reuse the repo’s metadata from Github’s API, and put the whole thing in the queue for Exversion with just a click of a button. But I wanted more. I wanted some way to reach out to the people struggling to use Github as a data sharing solution and let them know that we exist.

So once I confirmed the data had been imported correctly, I automated the process of forking the original repo, editing the file to add a link back to the “mirror” on Exversion and committed the change back to Github.

Let me tell you, who ever designed Github’s API is a very smart guy because there is one thing you cannot do through the API and that is create a pull request across forks. Working on this project made me realize how amazing it is that Github has not had the spam issues of other large, social websites. I suppose it would not be unfair to call what I was doing the world’s first pull request spam (but then again there are a lot of weird and wonderful things that go on via pull request) and I do feel a bit … dirty about it. Like, sure it’s incredibly evil, that doesn’t bother me … but it … mmm … inches a bit too close to an ethical line here.

At the same time, most everyone I’ve contacted through pull request has been incredibly cool. By preventing me from automating this last step I had to take the time to write a short message explaining that I’d found the data interesting enough to mirror on a site where it could be accessed via API. Most people putting data up on Github understand the convenience of having an API and were more than happy to accept my pull request.

It was a simple win-win outreach strategy: because even if the user never checked out Exversion to see what we offered over Github, we still got a nice link back from a high quality domain. And if the user accepted our pull request? That link back became even more valuable!

Github for Data

One of our most important goals in developing Exversion is trying bring together a community of data enthusiasts. There is no gathering place for people who love data: we cross too many age groups, industries, technical skill levels. But what sites like Github ultimately prove is how communication and collaboration within a community can incubate innovation. What would technology look like today if Github didn’t exist? Would languages like Ruby and Python dominate? Would Julia or Clojure ever gotten off the ground?

Traction is important, but far more important is reaching out to like minded people who will ultimately appreciate what you are trying to build.