My opinion on work from home has evolved recently. Ever since I graduated college 5 years ago, went into consulting, left and launched my own business, I’ve pretty much worked from home. That changes recently:

Last month I was accepted to be a part of Density Collective, Chicago’s preeminent startup coworking hub (and a resounding answer to ‘how do we build more cool startups in Chicago?'). So far I have really enjoyed it - it’s been a really interesting and welcome change of pace for me.

And ultimately it’s made me think a bit harder about the whole idea of remote work. Especially in the context of startups - it’s a complex issue that I think more early teams could be more intentional about. So I wanted to consolidate some of my thoughts here:

The Remote Work Landscape

First, let me clarify I am talking about early stage startups (<8 employees specifically), which is where we are. The dynamic really seems to hinge on the size/type of business, and your WFH protocol should probably evolve with the size of your team.

It’s also important to note that we’re still in the relatively early innings of figuring out remote work as a society. WFH was largely nonexistent pre-2020, and many of the big companies are just now swinging the pendulum back toward a return to office (famously JPM with the construction of their new $3B HQ on Wall St) with varying degrees of success.

A quick search tells me that early-stage startups are 2-3x more likely to work fully remote vs. the general workforce; only about 20-25% of startups are fully on-site compared to more than 61% for the general workforce:

Now I don’t think these numbers^ are incredibly shocking. I have generally been a strong proponent of working remotely (I like to think we’ve gotten pretty adept at it within our startup). But I think there’s a difference between desire and feasibility.

Why do most startups prefer remote/hybrid work? The obvious answer is that it’s far cheaper. Aside from the typically-named benefits (more flexibility, less distractions), working remote saves big in two ways:

1. No rent (dedicated desks at coworking space range from $300-$2000/mo)

2. No relocation expense to recruit top talent

The latter is the big hitter here. Working remote as a startup enables you to hire agnostic of geography - and finding top tier talent is arguably the most important piece. There’s a bit of a paradox; the highest talent density is in big hubs like NYC/SF, which also is where office space costs the most.

So given the choice, most startups will choose to save on office space, recruit from everywhere (argument to be made that confining your talent search to only the place you are HQ’d means you’re missing out on the majority of good prospects).

There are also obvious downsides to WFH in startups - speed/effectiveness of internal communication is the main one that comes to mind. The other is laziness.

Compared to typical business, a fundamental advantage of startups in the marketplace is being able to move faster than the competition. This appears to be (at least in part) a function of your ability to have impromptu, spontaneous conversations - the main benefit of working in person.

In a WFH settings there’s way more friction; you can’t physically bop over to your cofounder’s desk for a quick chat or jump into a conference room and use the whiteboard (the result is often async slack messages or the dreaded 30min Google Meet). If you’re not careful this will slow you down too much to compete.

Secondly there is the laziness. It’s true that people do tend to get productive outside of the panopticon, when no one else is there to keep you honest (though I suspect this is inherently less true in startups where are motivation and risk are often higher vs general workforce). No one will admit it about themself of course but when you are a boss you must accept it.

So what is one to do? Here’s what we’ve found:

How Should Startups Think About WFH?

For us the best solution is the following: 1) default decentralized work (ideally from startup-oriented coworking spaces) with 2) >quarterly in person all-team get togethers and 3) well-defined internal comm’s protocols

1) Default Decentralized

For most early-stage companies it just isn’t financially feasible to corral everyone into the same exact office 5-days a week. (If your team does happen to all be in the same city then great, but even so 3 or 4 days in person is probably enough of a balance between speed and distractions).

For us most of our team is split between Minneapolis and Chicago. So we have a membership at a startup-focused coworking space in both cities. The reason this works well is that you still have the ambient energy and focus that comes from being around other people building things, without the overhead of a dedicated office.

Plus, the networking opportunities and cross-pollination of ideas from other startups is invaluable. If you can’t find a coworking space find a hacker house or the coffee shops where startup people tend to work and make friends who will keep you accountable.

2) In-Person Team Weeks (at least Quarterly)

Once a quarter we bring the whole team together for 3-4 days to work together for a few days and plan our roadmap for the next few months. This seems to be frequent enough to feel natural while when everybody’s in the same room while not being overly expensive.

We try to make a point of really hanging out during these. We bake in social outings and do fun stuff together, which is really important. But they’re also our highest leverage moments for 1) strategic planning/big picture alignment, 2) tackling complex problems in front of the whiteboard, 3) rapid prototyping and decision-making.

It’s important to be really intentional about these. We set an agenda for them months out and each one feeds into the next one. TBH I wish we could do them more (maybe in the future we will).

3) Well-Defined Internal Comm’s Protocols

This is the glue that makes the rest work. You have to find a way to promote those serendipitous moments in a remote-first setting. It’s not a perfect science or set of tools (some platforms like gather.town are an attempt to make this more possible) but again it’s about being intentional, exemplifying from the top, and making sure everyone buys in.

For us this looks like: Daily 10min standups in slack, response time expectations, outlining when to hop on a quick call vs write it out (if it takes more than 3 back-n-forths, call), documentation standards (all decisions / meetings get recorded), 'office hours’ where we are avaliable for impromptu calls.

The key that I’ve learned (which was counterintuitive at first) is that the structure creates freedom. By being really explicit about how we communicate, you actually eliminate alot of the ambiguity that can slow you down.

Takeaway

There is no perfect answer (I will be excited to revisit this in a couple years to see how things have changed). BUT, defaulting to either extreme (full remote vs full in-office) without thinking through what works best for your current team is a mistake.

For us: the hybrid model captures ~80% of the benefits of being in-person while maintaining the flexibiltiy (and cost savings) of remote work. Most important i't’s a system that evolves with us - for example as we grow we might need more face time (or less). These are some of the things we’ve made to discuss during our quarterly in person sessions tbh. The framework lets us adjust without overhauling everything.

End of the day: the real competitive advantage isn’t whether you’re remote or in-office (pros/cons to both), it’s whether you’re intentional about creating an environment where great work happens consistently

Curious your thoughts?

Peace,
Ramsey