Welcome to benn.ventures

Because what else do we do?

To say it bluntly, I can't stand Slack. Superficially, it’s as good as software gets—it’s snappy and well-built; it’s approachable and friendly, both in its design and its personality; it has lots of ergonomic conveniences, from a wide set of keyboard shortcuts to impressively robust notification controls. And its funfetti brand was so popular that it reinvented the entire enterprise software aesthetic. None of this is bad, though I could do without all of the emojis.

But the bones of Slack’s glittering applications? The bones are horrible. Slack replaced well-organized email threads with a sprawling interchange of company-wide crosstalk. Companies that run on Slack run on group chats—there’s a text thread for every team, for every project, for every hobby and resource group, and, eventually, a group DM for every possible combination of five-or-fewer people. The day you start using Slack, it's a delightful little instant messenger. A year later, you have 3,000 unread channels, dozens of channels you've learned to ignore, and a sidebar multiplying towards infinity.

The issue, it seems, is that slack is for chatting. And chatting is for things like sharing pictures of your cats, or telling people that you’re running late, or coordinating an ambush on World of Warcraft.

Workplace communication is different. It's not inane chatter; it is—or at least, should be—more thoughtful conversation. Moreover, lots of messages need to be triaged. A request from your boss needs to be completed later; a long document needs your feedback; the matching criterion for the 21st input parameter in Channel File 291 of the IPC Template Instance really needs to be reviewed. If you get asked to do these things over email, you have options for how to manage them: Mark urgent stuff as unread; star them; leave to-dos in your inbox; delete or archive the chatter. And when you respond to a message, email forces you to reply in a thread. 

Slack does neither of these things. The principal thing that Slack encourages you to do is post a new message in a chronological chat room. And managing those messages is next to impossible, because Slack collapses everything into the blunt concepts of read and unread. Messages are either flagged with a literal red alert, or they’re effectively erased, thrown into a unrelenting river of automated posts and dissociative corporate prattle. There is no way to organize what’s happening in chat; there is no functional inbox for triaging stuff that’s read. In Slack, speak now, or the chaos will have moved on. 

For a couple years, there was a third option. Yammer, the first tech company I worked for, built one of the early products that tried to replace email with a SaaS app. In many ways, it was the opposite of Slack: The construction was shoddy, but the bones were great.

The design of Yammer was almost identical to Facebook. There was a feed of messages, with replies threaded below them.¹ The first message in each thread was the most prominent, and, as on Facebook and LinkedIn, the UI encouraged people to directly reply to messages rather than start new threads. Yammer also made a simple adjustment to how the feed was organized: When someone replied to a thread, that threat got bumped to the top of the feed. Conversations that generated a lot of replies tended to bubble up frequently, whereas less active conversations eventually fell off the screen. 

Yammer also had an inbox that let people triage conversations. It functioned much like email: If you were added to a thread, it’d get added to your inbox. When new messages were posted in one of those threads, the inbox would mark it as unread. See the message, it gets marked as read. If you want to remove a message from your inbox entirely, you could. 

It worked, and much better than I thought it would. You could go to the groups you cared about, and scroll through the feed, and read the thread starters just as you would skim subject lines. If something was interesting, you read the replies. If not, you moved on, slightly more aware of what was going on than before. Over time, you developed an atmospheric sense of what was happening—and because important conversations would naturally resurface, you rarely missed the key headlines. 

Unfortunately, Yammer never really caught on. It looked too much like a social network, so most of its customers used it as a water cooler rather than as an internal replacement for email. It eventually got bought, rebranded into oblivion, and tucked into some back corner of the Office suite, behind Microsoft’s own Slack clone. 

Glued on

A few months ago, Yammer founder, venture capitalist, and podcast host David Sacks launched Glue.ai. Demos of Glue look like a mashup of Yammer and Slack: It’s nearly visually identical to Slack, but, like Yammer, Glue is organized around an inbox and threads. If Slack feels like a giant company-wide chatroom, Glue feels like centralized email inboxes, where internal email threads are organized into publicly browsable groups.²

I…think I like it? It tries to be the best of both Slack and Yammer—structurally good bones, with a can of modern paint on top. It is lighter than email, and less insular, but more organized than the overcrowded airport terminal that Slack traps us in every day. Though I don’t think Glue will “reinvent workplace communication”—there are more dead startups buried under that tombstone than just about any other—it has as good of a shot as any.

Or, it did. Because Glue came out this year, in 2024. And if an app comes out in 2024, it can’t just be a clever new approach to a classic problem; it has to be “AI-powered.” Glue can’t be a communication tool for people; it has to be for “virtual team members” too. Startups can’t be a software business; they have to be an “AI company.” Their launch announcements have to have headlines about how they’re “AI native,” and they have to bury the interesting parts of what they’re building in the seventh post of the thread. This is Silicon Valley after ChatGPT: Nothing is complete without AI. 

Why? Why do we have to do this? How many good products are going to get ruined by unnecessary chatbots? How many simple ideas have been left on the cutting room floor because they couldn’t be shoehorned into the “age of AI?” How many promising startups went unfunded because “if you have a great product in the AI space, you can raise a Series A right away,” but the opposite is probably true if you are building something without AI? And how many good deals are out there because venture capitalists have been hypnotized by all this hocus pocus, and are ignoring the boring companies that aren’t draping themselves in the latest fad?

Be the change you want to see in the world, I guess. 

Are you starting a company that isn’t using AI? Are you here to make something dull, like a messaging app that still expects people to write their own posts? Are you creating a SaaS app that’s algorithm for organizing its feeds is “put the newest stuff at the top?” Do you employ real people as support agents? Benn.ventures wants to give you money.

Not much, mind you. Benn.ventures currently has an IRA in assets under management. And we’re down to a part-time salary and $800 in an HSA in dry powder. 

But raising venture capital isn’t just about raising money—it’s also about collecting endorsements. It’s about proving that you were one of the chosen few, selected by the ruthlessly exacting experts at Sequoia, at Benchmark, at Y Combinator. 

We don’t have a storied track record of success. And we definitely aren’t experts. But we are grumpy. We are selective, not because we know what we are doing, but because we are haters. We are not optimistic about the future. Given the current state of the world, you shouldn’t be building a company; you should be stocking up on beans and building a bunker. There was no CRM in The Road. 

People have said that investing is “taking your world view and deploying capital to try and shape reality to that world view.” My worldview is that I don’t like stuff. Your idea is bad; change my mind. I tried to build something, wasn’t so good at it, and am now bitter about it. A better person would say, “It’s time to try a new position, and to pay my experiences forward to the next generation.”

Nonsense. Silicon Valley is a status game, and status is zero sum. Much easier to tear others down than build ourselves up—to be Simon Cowell; Oscar the Grouch; Eeyore; Anton Ego; the Grinch, before his heart grew three sizes that day. Seeing successful young people zoom past us on the social hierarchy makes us feel bad, and our egos are fragile. We will never tell you we’re rooting for you from the sidelines because we’d rather you fail—we don’t want our LPs asking us why we passed on a big winner, and you failing makes us feel a little bit better about ourselves.³

Still, we’re greedy. You can apparently make a lot of money doing this, but you have to invest in something. So we will take your call, expecting to write a scathing review, but holding out hope for finding a few simple flavors from a bygone era. 

Frequently asked questions about benn.ventures

What unique perspectives do you have that differentiates you from other venture capitalists?

Pessimism? A general disdain for computers? We are a specialized firm, and our specialization is skepticism.⁴ You can comfortably walk into a pitch knowing there’s no pressure to convince us to like your company, because our default position is that we don’t like your company. 

We will tell you we’re excited to learn more about it, but we aren’t. We would like your pitch to be over; we would like to go to a long lunch; we would like to have a margarita. We would like to hurry up and make enough money so that we can retire. They say that there is no motivation like desperation, and we are up to our elbows in despair. 

What is your investment criteria?

That we like the stock.

Who are your limited partners?

Nobody. My parents? I am still on a Verizon family plan, and I think I use their Apple TV. Benn.ventures is not corrupted by the moneyed elite; we don’t invest on behalf of the one percent. 

If you would like to invest, however, we are open to bringing on new LPs. The fee structure is simple: 2 and 10 for 10—I charge a 2 percent management fee and an industry-low 10 percent carry, provided that you find 10 more LPs to invest behind you. It is critical that you do this last part, because we need their investments to pay your returns.

Are you founder-friendly?

Yes! Unless we believe that a company could be making us more money without the founder. But, look, that’s just business. Don’t take it personally. We are 100 percent behind our founders, so long as their interests align with our own. 

However, firing CEOs and writing punishing term sheets that aren’t copied directly from the YC website requires lawyers, effort, and a fair amount of business acumen. At benn.ventures, we have none of these things. We might try some weird 12-dimensional gambits, because what’s the fun of being a day trader without doing kooky trades, and what’s the fun of being in charge if you don’t instigate some boardroom shenanigans. They will probably fail though, because of a mix of bumbling incompetence and a sort of uninspired laziness. Just because we want to be Machevellian doesn’t mean we’ll be able to pull it off. 

How has the fund performed?

Imagine what can be, unburdened by what has been. 

What is it like to have benn.ventures as an investor?

We believe in the creative power of founders, and will use every resource we can to make you successful. We want to help you chase your dreams, and want to make those dreams even bigger. We aren’t professional investors, but operators who haven’t stopped hustling. We want to be the first person that you call when something goes wrong. We don’t just want to ring the bell at the New York Stock Exchange with you; we want to be in the trenches during your toughest moments too.

Hahaha no we don’t. We are venture capitalists because that stuff is hard. In the arena, your face gets marred by dust and sweat and blood; there is effort, and shortcoming, and, often, failure. We’re not trying to get our delicate hands that dirty. We didn’t come to Silicon Valley to struggle; we came to succeed.⁵ When something goes wrong, we want to be told about it after the fact, at the holiday party, long after it’s fixed. Our website doesn’t have a phone number for a reason. 

Is this real?

I mean, no. There is a minimalist website for old angel investments,⁶ but my books are an “Investments” tab in a Google sheet that’s called “Finances.”⁷ There is no legal entity called benn.ventures. Does making a joke about starting a venture firm violate SEC regulations? I don’t know, because benn.ventures doesn’t exist, and definitely doesn’t employ any lawyers who can answer that question.

Still, it could be real, partly because I’m not above selling my soul for attention on the internet, partly because working in venture does sound abstractly interesting,⁸ and partly—and this is the point that this very long preamble is ultimately leading to—because what else do you do? 

It feels like we’re starting to reach an odd frontier in the evolution of the Silicon Valley data professional. In the early 2010s, the “rockstar ninja” data scientist was all the rage; then, people became VPs of data and analytics. When that career path stalled—people can only build a data culture at so many 100-person series B SaaS startups before they get bored—analysts started companies. Now, as that era fades, those same people will inevitably start wondering what they should do next. 

The mid-level data executive merry-go-round is a plateau. Moving into other roles, like operations, finance, or product, feels like a soft reset. Starting a company is hard, and a pretty extreme “default” step. Joining Cigna as the Chief Analytics and Innovation Officer is a good way to get invited to Gartner panels. There are choices, but they’re all a bit uncomfortable.⁹

So what happens to all of us now? I don’t know. But some release valve will have to open somewhere, because a huge cohort of data people are about to be halfway through their second decade in the industry, and a bunch of them are going to wonder where they go next. And as much as I’d enjoy the joke, the world probably doesn’t actually need a Statler and Waldorf Capital Partners.

1. There were actually many feeds, organized by groups, which were analogous to Slack channels. 

2. This might be the best way to understand Yammer. It wasn’t a chat app, but an email app that grouped emails by team or subject, and put those emails in central feed that everyone could read and respond to.

3. In fairness, you’ll probably do the same? Our rejection letters will put a chip on your shoulder, and you will want to prove us wrong. Maybe that’s the real play here; we’re just a feeder firm for Spite Capital.

4. We also have hobbies that aren’t triathlons, Rapha, and Sun Valley.

5. We do want to choose, and we want to choose the podcast.

6. It’s in plain HTML and there is no favicon. Because we are purists who have real work to do, and can’t be bothered by whimsical things like colors and fonts and cascading style sheets. 

7. Other tabs include lists of stuff to sell on Facebook Marketplace, and gift cards that I need to spend.

8. Of course, when I was in college, working for McKinsey also sounded abstractly interesting. Fly around the country, parachute into important meetings, fire off some advice, and assign all the work that needs to be done to other people. But the reality—mostly formatting decks, I’m told—is awful.

9. Another possibility is that VP is the appropriate plateau for the Silicon Valley data professional. It’s perhaps not the position we want, but it’s the position we deserve.