Guess the #1 reason why investors didn’t want to invest in Hustle Fund back in 2017.

No, it wasn’t Eric Bahn’s obsession with minivans or Elizabeth Yin’s infatuation for hippos... The truth is that investors did not like that we were a fully remote VC fund.

Being a remote-first company wasn’t the norm pre-COVID, especially in the VC and startup industries. But fast forward 5 years later, we’ve grown to ~33 remote employees across 7 cities managing $130m. 😲

Going remote has been a huge competitive advantage for us… but it also comes with a unique set of challenges. In this week’s recap of Uncapped Notes, we share our take on remote work. We’ll cover:

1. The benefits
2. The downsides
3. What we’ve done to fill the gaps and build an amazing culture

Why we love remote work

There are a dozen reasons why our team loves remote work, but here are our top three.

#1 – Access to global talent

Talent used to be concentrated in a few main hubs, one being Silicon Valley. But we’ve always believed great hustlers can come from everywhere.

So by being remote, we’ve expanded our talent pool and found some incredible people to work with from around the world. The result is that our team has a diverse set of backgrounds and experiences to draw from. That’s awesome.

#2 – Cost savings

We don’t pay for office space, or utility bills, or high-speed internet. AND our team isn’t required to relocate. So everyone saves money and can live wherever they want.  

#3 – Flexibility

We’re big on prioritizing output of work over clocking a certain number of hours. So if someone needs to take their kid to swim practice, or go for a long run, it’s no big deal.

We trust each other enough to be focused when we need to be. So far, it’s worked extremely well for us. 🙂

Potential downsides

Remote work isn’t for everyone. Here are some common problems we’ve seen ourselves and in our portfolio companies.

Team communication can be slow

When the sun sets on our teammates in California, the sun rises in Singapore, where some of our other teammates are based.

So we need to be mindful when we schedule our company-wide meetings. We have to time a time that works for everyone. Or if we’re working on a project with a Southeast Asia-based team member, we need to think ahead about when to respond or make requests to avoid 24-hour delays.  

Potential for isolation

There’s a risk of feeling like everyone’s on their own little island.  

Some people (like myself) don’t mind this because we know we’ll see each other 3x/year for our team offsites. And that we can hop on Zoom anytime if we need a quick brainstorm session with a teammate. But this can be an issue for those newer in their careers.  

When I was first starting out, I learned so much just by being in the office every day.

• I had walking meetings with my manager who took extra time to mentor me.
• I could turn around and the editor-in-chief could give me direct feedback on my drafted article.
• Some teammates and I could brainstorm an idea and spontaneously spend an hour spitballing with a whiteboard and Post-it notes.

Now that I’ve experienced things like this for a decade now, I’m comfortable doing a lot of this online. But for someone just starting out, they may not have had the same lived experience to know what “great work” looks like. This leads me to my next point.

Being afraid to ask for help

When Eric Bahn was first getting started in his career, he was afraid to ask for help. But his teammates could walk by his cubicle, notice his mood, and say something like “Hey Eric, you seem to be frustrated” or “You seem a little down. Is everything ok?”

Then they would stop and proactively help Eric.

In a remote world, we are less in tune with how our teammates are on a day-to-day basis. Which means that remote employees need to be hyper-conscious of their needs, and proactively ask for help when they need it. There are simply fewer opportunities to naturally check in on each other.

How we dealt with these challenges

While we’re not perfect, we are proud of the remote culture that we’ve built at Hustle Fund. Here are a few things we do to address these common pitfalls that have a huge impact.

Give shout outs

We run our comms through Slack and have a special channel just for #shoutouts.

When a team member does something amazing – big or small – we have the opportunity to show gratitude. The entire team throws up an emoji or adds a comment to make them feel valued.

It’s such an easy thing to do. The channel is active every day because we’re always showing appreciation toward each other.

Document everything

We recently worked with Thenuka Karunaratne, our entrepreneur-in-residence, to build a system called Company OS.

Company OS is a place to locate ANY piece of info within Hustle Fund.  

I joined Hustle Fund full-time in January to produce Hustlers’ Retreat, our flagship event for founders. I wanted to learn more about how our team had run events in the past.

Within Company OS, I was able to find my teammate’s project on a previous event, and learned a ton about how to get started… without having to schedule a meeting with her. I could easily see the past speakers, agenda, launch plan, sponsors, etc.

We do this for every project. All the initiatives we’ve built – from Angel Squad to Uncapped Notes to our Deals team – are clearly documented.

This has been an absolute game-changer for us. If this is something you want to dive deeper into, Thenuka is giving a 3-hour workshop on building your own Company OS live at Hustlers’ Retreat.  

Plan team offsites

Even though we are fully remote, we are human and we love seeing each other in-person. So we plan team offsites 3 times a year for 4-5 days.

This is dedicated time to reflect on where we’ve been and think strategically about where we’re going. And we always budget in time for fun activities for our team to bond. We’ve hiked in Vietnam, skied in Oregon, and played bocce ball in San Jose.

If this is your vibe, we’re hosting a guided offsite for founders at Hustlers’ Retreat next month. There’s gonna be night hikes, pool parties, ghost stories, and so much more. ⛰️

Phew, that was a lot

Remote working isn’t for everyone. For it’s made our entire team happy and productive.

There’s been a lot in the news about companies mandating employees to return back to the office. But COVID has accelerated the mindset shift for employers everywhere that people can still be effective without being physically in the office.

I believe remote work is here to stay. What do you think?