“Fill Your Cup First”: Wellness for Remote Entrepreneurs

Stefan Palios

Jun 18, 2020

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Rebecca Jacobs and Cailey Gibson have never met in person. Yet they are co-founders of Anika Works, a platform that helps nonprofits connect with impact-focused businesses. Their journey is one that seems odd when you consider the lore of co-founders meeting in college, or being high school buddies, or a chance meeting at a tech event. However, they are one element of the new reality: building a remote business does not require knowing someone in-person beforehand.

Despite not meeting in person, both were adamant that they built trust and vetted each other before agreeing to work together - there couldn’t be a “let’s try it and we’ll see approach.” Further, both care deeply about wellness and self-care, something that gets harder when you are working remotely and prone to feelings of isolation.

In this Remotely Inclined Chat, Rebecca and Cailey share how they met, how they vetted each other to build trust, and how they ensure wellness is built into the fabric of their business.

Vetting a co-founder you’ve never met

The two met in a facebook group, when Rebecca was looking for some social media and marketing help for Anika Works (initially, Rebecca was a solo founder).
Cailey did some work, but found that she wanted to get more involved -- that led to the co-founder conversation.
A big part of vetting for both Rebecca and Cailey was checking self-awareness and learning about who the other person becomes under stress. The key resource they pulled from was the Founder Institute’s 34 Questions to Ask a Potential Co-Founder.

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Taking care of yourself has been critical to Anika Works’ mission from day one, so the team prioritizes it.
Rebecca loves Ink Blot Therapy and the community of founders she built through the Founder Institute accelerator.
Cailey shared that the company has a #TeamWellness Slack channel where they hold each other accountable to personal wellness and the company has an open calendar for the team with different meetups, suggestions, and wellness tips so people don’t have to spend time searching for insight.

The final word

“Get comfortable with vulnerability. It’s scary, but that has been the source of so much of my growth and ability to succeed in this business.”

Remotely Inclined Chats with Rebecca and Cailey from Anika Works

Transcript edited for brevity and clarity.

Stefan: Welcome, Rebecca and Cailey! Can you share what Anika Works is all about?

Rebecca: Thanks for having us! Anika Works is a matchmaking platform where we help connect small nonprofits and grassroots organizations with service providers and corporate sponsors that help them prepare for fundraising, connect with the right donors, and help their organization so they can do more good.

But you two haven’t actually met in person? Tell me about that

Rebecca: Absolutely. What happened was that I was a solo founder to start. I came in with this idea. I went through the Founder Institute in Toronto. I noticed that in the trenches, it can be tough to be alone through all of it. So I knew that if I wanted this to work I’d need to find people better than me at everything except for the few things I could focus on and engage with.

I found myself in facebook groups. It was also my first segue into remote work because it was something I was curious about. One group, for female founders, I stumbled across Cailey as I was requesting help for marketing. She was a fantastic service provider for me, helped me set up our own facebook group that is now thriving.

We’ve now known each other for about six months and have been working together, but we’ve never met in person.

How did you vet each other without meeting first?

Rebecca: There needs to be some meaningful conversations happening. I want to make sure that my co-founder has all the information available and make sure it’s a fully transparent process. Ultimately my mindset was making sure she feels that she’s getting as much out of this as I did.

Cailey: We did a 3 page questionnaire - it took us about two hours to do it. If someone’s not willing to spend that kind of time to get to know you, then there’s a question of how you will manage when times get difficult.

One of the questions I remember was how you handle stress and what your conflict management style is. I let her know that I’m the type of person who mirrors the other person. If they are being passive aggressive, I’ll be passive aggressive. It’s definitely not one of those things you think is a great quality about yourself that you can’t wait to share, but it helps both of us realize that when you know the other person’s style, you can pick up cues and support each other.

Remote work can be lonely. Has that been a challenge for you?

Rebecca: Absolutely. It has been at the core of what inspired Anika Works and hopefully what will continue to inspire our culture as we grow. Founding Anika Works came from my experience working in East Africa in social sector work. One of the things that came up for me early on in the process was the struggle to balance what it means to take care of yourself and to give to others in your organization. It was something I noticed across the board that people were struggling with in this sector.

How do you address wellness at Anika Works?

Rebecca: As we now enter the entrepreneurship and tech space, it’s become very apparent to me that this is not something that’s sector agnostic. It is something everybody experiences. From the beginning it was a personal mantra that I can only do my best. I can only bring 100 percent of myself to work. And I can’t help people if I don’t first fill up my own cup and take care of myself to the point where I’m not worrying about burnout or worrying if I can get out of bed today. It’s been part of my journey from the get go.

For me, Founder Institute helped because I connected with a community of entrepreneurs. I also connected with Ink Blot Therapy, which has been a huge part of how I’ve maintained my wellness. I also think about putting myself out there, however scary.

Cailey: We have a #TeamWellness channel in our Slack. It’s almost an accountability channel of making sure that everyone’s prioritizing their wellness and making it easy for people. Finding time to scour the internet, especially with a lot of things being closed, isn’t good.

We also created a Wellness Calendar that people can quickly scan for things like a daily yoga class to check out. It just gives them something easier to plug and play rather than taking more than 30 minutes to go search for something.

What’s your advice for new entrepreneurs that want to hustle but also prioritize wellness?

Rebecca: First, congratulations on taking that risk and that step. It’s a hard path in a lot of ways, but also beautiful.

Then I would say get comfortable with vulnerability. It’s scary, but that has been the source of so much of my growth and ability to succeed in this business.

Cailey: Don’t try to control everything. You can’t ever be fully prepared. Just do as much research as you can, then start - with someone holding you accountable (whether a family member, friend, or Facebook group so you know you have a deadline).