Remotely Inclined

Hi,

Welcome to Remotely Inclined, a newsletter about running a business remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Respond to this email (or send me one). Or just read on…

First: I recently stumbled upon Hauniv, an amazing monthly email digest of the startups that have raised money (they manually verify the data - no robots). If you’re interested in the startup space, you should definitely check them out.

Today: We’re talking about how to build a thriving remote business of one with Anna Codrea-Rado, a NYT and Guardian journalist turned remote entrepreneur.

Anna Codrea-Rado started her career as a journalist, eventually getting laid off by Vice Media in one of their mass layoffs. Instead of getting another job, Anna decided to go freelance, publishing pieces in the New York Times, Guardian, and more. From there, she built a fully-fledged business of one with multiple streams of income coming her way. 

In our interview, Anna shared how she started her business of one, the process she used to build multiple streams of income, and how she continues to expand even though she is still her only employee. 

Setting up multiple streams of income

→ When Anna was laid off, she decided to go freelance and her main income source became pitching and selling stories to major media outlets or magazines. She knew she wanted to grow her income in other ways, so she looked at building out new opportunities. 

→ Now, Anna still writes for major outlets but also has: A podcast, a paid newsletter, online courses, and a forthcoming book on building a freelance business of one.

→ Getting to this point required a shift in thinking. Here’s are the questions Anna asked herself that led to identifying new business opportunities: 

* Who else wants your skills? In Anna’s case, she started with media outlets but corporate blogs wanted her skills as well, which opened new client opportunities. 

* Who can you teach your skills to? Anna taught writing in journalism schools and now teaches freelancers how to build their businesses. 

* What else can your skills produce? Instead of only writing for media outlets, Anna started self-publishing her newsletter, The Professional Freelancer, and is now writing a book.

* How can you step out of your comfort zone but lean on your current skills? Everything Anna does is based on her skills as a writer and journalist, so she has a higher chance of success from the start. 

Building your own support systems

→ As freelancers and solopreneurs, it’s easy to feel lonely, isolated, or just plain alone with no one to ask for help or advice. 

→ Anna found that the way around this is to find two kinds of people: 

* General support such as a spouse or friend. The one who will tell you it’s going to be alright when things get touch. 

* Colleagues / “work spouses.” This is the person you can turn to with professional issues who can offer real advice based on relevant experiences. 

→ Once you have your support systems in place (Anna calls it your “emotional emergency fund”), it becomes a lot easier to stand up for your rights to be paid fairly, paid on time, and treated well. Solopreneurs work with multiple stakeholders, often with a power dynamic involved, so having additional support systems help give you the courage to ask for what you deserve. 

The final word

“[Growing my business] was about learning my options, what made sense for me, and going one step out of my comfort zone but very much leaning on my existing skillset.”

Remotely Inclined Chats with Anna Codrea-Rado

Transcript edited for brevity and clarity.

Stefan: Welcome, Anna! Can you share what your business is all about?

Anna: We were just saying before recording that there isn’t really a neat word for encapsulating everything that I do, but I always say first and foremost that I am a journalist. That’s what I’ve done for the past three years working remotely for myself. Beyond that I am building out more of a digital business. I still do traditional journalism for legacy media organizations like the New York Times, Wired, and the Guardian. Then I have a newsletter called The Professional Freelancer. It’s on Substack, which is how we got to know each other - through the Substack community. I also have a podcast called Is This Working, which is about the messy parts of work. And I campaign for freelancer workers’ rights while working on a book - it’s a guidebook for freelancers and anyone else who wants to work for themselves. 

You built a lot of revenue streams for your business. What are the mechanics behind your business and its growth?

I believe very passionately that a diverse portfolio of income streams is really fundamental for anyone, regardless of whether you’re employed full-time, a freelancer, or whatever your business structure looks like. Multiple revenue streams provide a bit more stability and security - they spread the risk out. It’s simply not putting all your eggs in one basket. 

I also think that there’s a bit of an image problem with multiple streams of income because it’s such an unsexy phrase. I know we have side hustler, but I don’t think that quite gets to it either. 

I got into freelancing in 2017 when the company I was working for, Vice Media, pivoted to video and had a massive global layoff. I started with my existing skill sets and how I could package them up differently and sell them to different types of clients or in a different format. 

So you think about large businesses and think about it in terms of B2B or B2C. I’m both since I sell to individuals and to large organizations. 

I built it all one by one. I started with traditional journalism - selling articles and stories to newspapers and magazines. Then I started adding new ones. I started doing some public speaking. Then I started doing some teaching and 1-1 coaching. Selling the newsletter came a bit further down after I’d built up the audience. 

It was about learning my options, what made sense for me, and going one step out of my comfort zone but very much leaning on my existing skillset.

How can people get started finding that first “thing” they can use to become the foundation of their business?

Start with an audit of your own skills and what you’re doing, because it’s easy to forget how valuable the skills you already have are. If you’re doing it repeatedly or have been doing it for many years, you take for granted that you have something very valuable. It’s a good idea to think about who else might want to have that thing. 

Take myself for example. My main thing was writing journalism. So then I thought about what other offshoots come from that. One of them is that I can teach the business of freelancing and the business of journalism. That is often a first step when you’re thinking about multiple income streams: what skill can you teach to others? 

For a lot of people, it’s easier to teach than you might think it is. And you can teach in lots of different formats. I’ve taught guest lectures at journalism schools. But you can set up your own webinars or online events - or in person events if we ever get back to a time when we do those. 

Then you can think about who else wants the actual skill. In my case, it’s distilling complex ideas into easily digestible copy. That’s a skill that not just media outlets want to buy. So you can take it and sell it to companies that maybe want to start a blog. And then you can end up in a place where you’re selling directly to your readers. 

It’s really starting with how am I looking at something and what are other ways it could work for me. 

How do you balance advocating for your own rights as a freelancer with so many stakeholders and clients?

It’s much easier said than done. But I have been advocating for freelance workers’ rights, particularly around pay. I have two campaigns at the moment. One is about late payment terms in the media and journalism industry, since all freelancers face issues with getting paid on time because of the power imbalance. 

Then I have a campaign around pay disparities in what I’ve identified as the freelancer pay gap - differences in pay that freelancers experience depending on a number of factors like gender, race, ethnicity, age, location, and all of these things. On top of that, there’s a disparity between what a freelancer gets paid versus an in-house person, with wages in favor of the in-house employee. 

Nonetheless there are structural problems that make freelancing unnecessarily difficult. So as freelancers it’s really important that we educate ourselves on what our rights actually are and then try as hard as we can to stand up for them. 

As a solo business owner, you can also work with other people. You can hire people to help you out. I’ve recently started working with a bookkeeper, since it’s difficult and draining and this person is better at it than I am. I’m paying for peace of mind and mental health, basically. It can be scary when you work for yourself and think that hiring someone is scary and daunting. But in the long run it’s investing in not only your business but yourself. 

What’s your advice for folks just getting started in their business?

This might sound counterintuitive, but I think when you are a business of one you need a work spouse or freelance advisors - your kind of freelance board of executives. 

However you want to think about it, you need people. You need them to support you but also people to give you solid business advice and who can talk to you about your specific issues. The number one challenge freelancers face when they work alone is there’s no one to turn to. I’ve lost so many hours just to self-doubt because I haven’t had someone who can share an idea. 

You also need an emergency fund and all of that practical stuff. But there’s an emotional side of working for yourself - you need the emotional equivalent of that emergency fund. Build up that support network - it will pay off in the long run rather than finding yourself in a position where you need that network and then not knowing where to find it. 

Amazing, thank you for your insights!

You can get in touch with Anna and Instagram and Twitter. You can pre-order her book on Amazon.

Image via Instagram

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about running a business remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Respond to this email (or send me one) Or just read on…

First: My book is live in paperback! If you know any freelancers (or are one yourself), I hope you enjoy it.

Today: We’re talking remote salaries, documentation, and more with remote work consultant Rhys Black.

Rhys Black started his career managing remote teams before starting his own multi-national, all-remote company helping government trade agencies connect with entrepreneurs. Now, he runs Delocate, a consultancy based in London, UK, that helps companies plan their remote work strategies.

In this interview, Rhys shared his insights on how remote companies can better use documentation to encourage autonomy in employees. From there, he sounded off on what he thinks the remote salary debate is really going to be about. 

Remote leader to remote entrepreneur

→ Rhys started his career leading remote product teams, engaging with developers, marketers, and designers all around the world. 

→ His first foray into entrepreneurship was a company called Trade Nations, which helped government trade promotion agencies connect with entrepreneurs and level-up their marketing. He built a distributed team across Europe and Latin America. 

→ His friends started asking him for advice on how they could run their remote teams more efficiently. Soon, he had too much demand on his time. He moved on from Trade Nations to found Delocate, his consultancy focused exclusively on helping companies set up the backend processes and culture frameworks to make remote work successful. 

Asynchronous is king

→ When working remotely, particularly with team members in multiple time zones, Rhys advocates for becoming as asynchronous as possible (asynchronous basically meaning that you don’t expect an immediate response to a message). 

→ Asynchronous communication starts with documentation. When companies build “lean documentation” - treating any internal document like a product intended to solve a problem (or answer a question), you can train people to build a muscle memory that they should always check the documentation and do some of their own research first before asking another team member for help. 

→ From there, leaders have to encourage and promote a culture of non-immediacy. This means reminding people who are always jumping from question to question that they should be focused on their own deep work and to let people’s questions sit for a bit. Part of this, of course, is having nomenclature or a tag for truly urgent issues, since sometimes you really do need an answer right away. 

Tools mentioned in this episode

* Notion

* Slack

* Loom

* Salesforce

* Asana

* Tandem.chat

The final word

“I think that it [salaries] become a bit of a land grab by some of these larger tech companies. They are happy to continue to pay San Francisco salaries. So they’ll do it to suck up the best talent around the world in the short and medium term.”

Remotely Inclined Chats with Rhys Black

Transcript edited for brevity and clarity.

Stefan: Welcome, Rhys! Tell me more about your work with Delocate

Rhys: Yeah. My background is in the tech industry, predominantly in London, UK, and a bit in the US, as a program manager. I was managing teams of developers, designers, testers, and marketers. Those teams were usually some form of remote. Not necessarily fully distributed, but a mix. 

Then I started my own company previous to Delocate called Trade Nations, which was a fully distributed company with employees in Europe and Latin America. We were working with governments, specifically trade promotion agencies. 

Delocate kind of spun out of Trade Nations. I started helping some friends who had businesses and were running remote teams. They were having a lot of similar challenges, and I’d made all of the mistakes already. So it was telling them what to do and what not to do. It evolved from there. 

What were the top three challenges you noticed on remote teams? 

The first thing would probably be the basics of collaborating and communicating together. Especially when time zones are involved. 

One of the things we work on with clients is helping teams become as asynchronous as possible. That’s a big part of it when time zones are significant - you can’t be waiting on someone for 10 hours. So the first thing is to create an environment where people can answer their own questions and get to work. 

The other thing is creating an environment that is as distraction free as possible. When you’re working synchronously, it’s easy for teams to end up answering everybody else’s questions more than focusing on their own work. 

How can a founder or team leader create distraction-free environments?

One of the most important things is to create a culture where hyper-responsiveness is not tolerated. If people see it happening, it should be cracked down on pretty quickly. If you don’t breed that culture in a remote company, it can wreak havoc. You need to be pretty staunch on that and make sure your team realizes that we don’t expect you to respond immediately. 

We don’t want you to respond immediately because we want to create a work environment that allows you to get into flow. It’s a much more enjoyable experience as an employee to be more productive and focused as opposed to pinging you left, right, and center every couple of hours. 

Does that mean leaders should punish people for responding quickly?

No I don’t mean cracking the whip on people, but I mean being proactive in creating that culture. A lot of the time culture is just left up to chance. It’s about being proactive so people know it’s very clear. Then it’s a case of nudging a little bit and creating habit formation. Eventually, it becomes second nature and the team starts to moderate everybody else. 

Should leaders remind people they don’t have to respond to everything immediately? 

Yeah. I did that in my own company. I regularly had team members that I could see they were messaging too much in the evenings and things like that. I’d tell them that I was not expecting a reply that moment. It’s just about setting the expectation. 

Can over-documentation reduce creativity?

Documentation has a pretty bad rap. It’s thought of as this thing that gets written and then never really used. That certainly shouldn’t be the case in a remote company. 

In my eyes, documentation has been created wrong - or suboptimally - for quite a long time. There’s a balance between documentation and spontaneity. In a young company, you don’t want to kill the best thing a company has which is agility and being flexible. 

I approach documentation like any product, since documents are the productization of knowledge. You can create a document in a very lean way - it doesn’t need to be a 10-page thing on a particular topic on day one. 

What I usually tell clients is to link all these individual pieces of information in Notion. Add a blurb or context about what it’s for, and then let that be the seed of the documentation. If it starts to get traffic and traction, then maybe it’s worthwhile to take that information and consolidate it a bit. 

But documentation is useless if you don’t use it. You have to build that muscle memory where instead of pinging someone on Slack, first look in the documentation. Then comes the balance point: if you’re looking for 20 minutes, maybe it’s time to call it quits and message someone you know has the answer. So it shouldn’t get in the way of asking questions. 

What’s your opinion on setting remote salaries - should it be done by location?

It’s an interesting topic. How do you price Thailand in a global market, for instance? It’s not something I typically advise our clients on, since there are some good salary calculators out there. 

I think that it will become a bit of a land grab by some of these larger tech companies. They are happy to continue to pay San Francisco salaries, since pretty much anywhere else in the world is cheaper than San Francisco. So they’ll do it to suck up the best talent around the world in the short and medium term. 

Amazing, thank you for your insights!

You can get in touch with Rhys via email.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about running a business remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Respond to this email (or send me one) Or just read on…

First: Welcome to new subscribers! If you know someone interested in running a business remotely, I’d be grateful if you forwarded them this newsletter.

Today: We’re talking choosing to go remote, structuring a business in a way that works for you as an entrepreneur, and the power of moving your energy where it’s valued.

Avery Francis has been an HR leader for years, but went out on her own to found Bloom in 2018. The company has been some form of remote from day one, but went fully remote in late 2019, and Avery has since run the business from Canada, Scotland, the Netherlands, and more. 

In this conversation, Avery shared the biggest shift she made as an entrepreneur - and how it led to generating over $500,000 in revenue from Instagram, only working 28 hours a week despite growing quickly, and becoming more profitable than she ever thought possible.  

Copy what you know and end up a copycat

→ Avery worked for a few companies before she went out on her own to found Bloom. In the beginning, Avery structured Bloom based on copying her experience at her previous employers. 

→ This helped her get off the ground, but she realized that the business wasn’t actually serving her. She was making some money, but was working more than she wanted to and in a way that didn’t feel authentic to her. 

→ She thought actively about the kind of business and lifestyle she wanted, not just what she knew about at the moment. This was based on personal desires, what she admired about other companies, and Bloom’s values. From there, she started to restructure Bloom to better serve clients, make more money, and provide a better lifestyle for her and her team. 

Changing for the better

→ A key part of Avery’s realization is that she wanted to travel more and build a business that served her, instead of the other way around. 

→ Here are a few of the changes Avery made to her business: 

* Moving from 5 days a week, 8 hours a day to 4 days a week, 7 hours a day. 

* Moving from working on client site to working remotely with occasional client visits. 

* Not being available 24/7 on email for clients and setting boundaries. 

* Launching more specific services, including Bloom Experiences, to evolve the company away from just contingent recruiting. 

* Invoicing monthly instead of bi-weekly. 

→ These changes not only provided a far better lifestyle but made Bloom more profitable, as new services brought in revenue and monthly billing allowed for more client development without concern that an invoice was always coming the following week. 

Twitter energy on Instagram

→ Another part of Avery’s transition with Bloom was to bring her personality more into the business. She wanted a business that allowed her to be herself, not have to put on a face for clients. 

→ As part of that, she started using expressing creative / visual side, taking the insights she would share on Twitter and creating graphics for Instagram. One Instagram post took off, and helped her gain over 70,000 followers - including Arianna Grande. 

→ Her newfound platform with Instagram helped Bloom and Avery reach a global audience, which so far has resulted in over $500,000 in new business - just from leaning into the things she already liked to do and building a business that supported who she was as a person.

The final word

“Once I got to the point where I had overcome my own assumptions about the type of business that I was going to build, I moved away from basically copying what I’d already seen, done, and what already worked. I was able to build a company that was right for me.”

Remotely Inclined Chats with Avery Francis

Transcript edited for brevity and clarity.

Stefan: Welcome, Avery! Can you share what Bloom does?

Avery: In a nutshell, we help companies build the world’s best workplaces. 

You were hybrid remote but decided to go full remote - what was your decision making process like?

We made the decision to go fully remote about four months before COVID hit. It had been something I’d been working toward for about a year and a half since founding my business. I realized a lot of work could be done remotely. 

I spend a lot of my time having confidential conversations or conducting interviews, and often I’m working in a startup environment in these big open spaces. There was often either not a lot of office space or not a great desk situation for me. 

I’ve also been in a long distance relationship for a very long time and it came to the point where one of us had to make a move - and I’ve always wanted to work in the UK. So I took advantage of my dual citizenship and built a company where I can work remotely and work from anywhere in the world.

How did you adjust client expectations?

I’m really lucky to attract and work with some really amazing companies. When I initially said Bloom is moving to a more fully remote team, there were no questions asked. 

There were no client challenges. The challenges that were presented was making an adjustment in the way I structured my business - and that meant hiring more people. While I was running and operating the business from Scotland, I had three people based in Toronto continuing to work onsite with clients, but in a more passive basis versus being on site for eight hours a day. 

Did having to hire change you as an entrepreneur?

I needed to rework how I was thinking about the company I was looking to build. Being transparent, I was working with an organization that did - and does - very similar work to what we’re doing at Bloom. And I had structured my business off of the company I was working with prior. As a result, I was building a business that wasn’t the type of business I would want to be working in. 

So it wasn’t necessarily external factors that caused challenges, but it was my own way of thinking. Once I got to the point where I had overcome my own assumptions about the type of business that I was going to build, I moved away from basically copying what I’d already seen, done, and what already worked. 

I was able to build a company that was right for me. 

What were some of the unique elements that worked for you?

When I used to work full time, I would go from one company to the other. What I found in terms of making this transition to building Bloom is that I had complete freedom to mess up, to make mistakes, and to build something true to me. 

* The way we structured our days. 

* In how we collaborated with clients. 

* The way we communicate. 

For example, we’re in a busy season but we don’t work Fridays. We’ve had a four day work week for well over a year now. That’s what the team prefers. And we don’t work eight hours a day, we work seven. And even when we answer emails, we set really clear boundaries with clients in terms of when we’re available to chat and when we’re there to support them. 

For invoicing, instead of doing everything on a biweekly basis, which is what I was used to, we do monthly. It’s actually influenced us being more profitable. 

You also launched new offerings and leveraged new growth channels. Tell me about that

The plan was to launch this new offering months ago, but COVID hit. So we’ve been doing this work, and now get to formally introduce it: Bloom Experiences. It’s for organizations looking to bring in a new approach to corporate training and education for their teams. 

At Bloom, we’re all about growth. It’s what we’re best at. We wanted to specifically look at how we were actually helping companies grow. We look at our values and how we’re able to impact growth, and we’re really good at building those systems and structures so companies can scale in a meaningful and intentional way. 

So we were able to put in great, equitable hiring systems. But once these people get hired, what were we doing to further grow these folks? That’s where the education and deep learning experiences come into play. 

Obviously, with the uprising of the Black Lives Matter movement recently, we’ve been doing a lot of diversity, equity, and inclusion learning experiences too. 

Most coaches and consultants are on LinkedIn or Twitter. But you’ve found success on Instagram. How did that happen?

Yeah! I have celebrities like Arianna Grande following me now. It’s funny. 

What was meant to be a tongue-in-cheek post about what non-Black folks can do to better support Black people … kind of spiraled. 

What I’ve been saying is that I take my Twitter energy to Instagram. Instagram is a flex in terms of where you’ve travelled, who your friends are, and maybe a cute photo of your beautiful partner. And Twitter’s where you flex your brain muscles and talk about the things you’re passionate about. 

And then I do it in an aesthetically pleasing way. I’m serving up - in some cases hard - lessons from my own lived experiences as a Black woman or some tongue-in-cheek advice.

(She uses Canva to design her beautiful Instagram carousels.) 

What’s been the result of that Twitter energy on Instagram?

Just in the past two months, it’s resulted in over $500,000 in revenue. That’s pretty wild. It’s very unexpected. I didn’t know that I’d be able to build these kind of deep connections and relationships on Instagram. 

I love sharing ideas and sharing how to do it. I’m happy to share all my tips and secrets and how I navigate what I do. With Instagram, it feels more in tune with who I am. I’m a creative and visually driven person. And the design works for me. You’re confined. You’re forced to break down your ideas and concepts. You only have nine frames in a carousel to work with so you have to be really direct and concise with the ideas you’re sharing. 

I found Instagram is a great place for me to test out content before I put it on Twitter, too. 

What advice would you share for entrepreneurs choosing to stay remote post-COVID? 

The biggest hurdle I’ve come across is just my own mindset and how I think about the company that I’m building as an entrepreneur. Choice is really important in terms of not being totally dogmatic in terms of what’s going to be your company now versus your company five years from now. 

Amazing, thank you for your insights!

You can get in touch with Avery on Instagram and Twitter. 

Image courtesy Avery Francis’ Twitter.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about running a business remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Respond to this email (or send me one) Or just read on…

Buffer makes over $20 million in revenue annually, but they don’t have a sales team. Instead, they have a lifecycle marketing team led by Ashley Hockney. She started working remotely at Zapier, then as an entrepreneur, and now at Buffer. 

In this conversation, Ashley shared more about how Buffer grows without a sales team and the tools and processes she uses to lead a distributed, remote team of marketers across the globe.

A remote marketer’s toolbox

→ Buffer is timezone agnostic, so all documentation and collaboration has to be inclusive of people in different timezones. A big way Ashley does this with her team is through Slack threads. That way, everyone can see the core topic and add their thoughts into the thread. When organized properly, threads are easily searchable, so anyone in the company can learn about what’s going on. 

→ A powerful “tool” in Ashley’s arsenal is not a tool at all, but being a moderator. Buffer has guides on how to communicate - what type of information goes where, for instance - and Ashley spends some time ensuring those guidelines are followed. Because the team is asynchronous and remote, clean data is critical for team collaboration and knowledge sharing. 

How to be a remote marketing leader

→ Remote marketers have to show their emotion, thoughts, and personality through writing. If you’re not a strong writer - and even if you are - Ashley recommends leveraging emoticons, smileys, and other types of content to help express emotions if you don’t have the words to do it. This is often frowned upon in “professional” settings, but can be incredibly helpful at generating connection and understanding remotely. 

→ Leadership is about providing your team access to data and information, but then giving them time and whitespace to learn by themselves. A good marketing leader might be smart, but cannot teach their team everything. As well, in order to encourage learning on their own, a team leader has to both demonstrate that for the team and make sure people have time and autonomy to learn. 

The final word

“[Remote work] is truly something I think is here to say. Allowing life to be a priority over a commute. Letting people get two hours back in their day to say “this is my time.”

Remotely Inclined Chats with Ashley Hockney

Transcript edited for brevity and clarity.

Stefan: Welcome, Ashley! Tell me about yourself and your work at Buffer.

Ashley: I joined Buffer as the Director of Marketing and was running this team of product marketers, growth marketers, email, and community. We were looking at our customers and thinking how we could serve them. Traditionally, you might see a marketing director really invested in revenue, leading into growth hacks, etc. 

But I’m now the Head of Lifecycle Marketing, which is a bit of a divergence from that. We look a little bit more at lifetime value (LTV) and how we support users, not just at the moment of coming into the funnel, onboarding, or confirming at the end of a trial. It’s what happens after that. 

Buffer is famously remote. But you don’t have a sales team. How do you do business remotely without a sales team?

I’ll break it down into parts and explain why it made sense to focus on lifecycle marketing at Buffer.

With a sales team, you’re devoting a lot of time to one-on-one attention, but it’s also very outbound. There is a lot of value in that, particularly in B2B companies or enterprise-focused companies. But when we think about lifecycle marketing, the actions are a little more at scale or data-driven. It’s more about how we can achieve that customization through smart data at scale (Lots of big words, I know). 

A lot of this aligns with Buffer - who we are and what we know that people love. When we think about our value proposition and positioning in the market, we think about why we are great at this - and it comes down to our brand, how we do things, and how we think about our customers. 

It’s also things like our transparent salaries and our culture. That translates a bit into our product as well - with what we hope is a simple UI. With those things in mind, a business model of going really upscale and trying to one serve someone with a thousand-dollar budget just didn’t feel like us. So when we think about how we grow and scale the business without reaching for big contracts, it became about serving more people at a more accessible price point. It just felt really on-brand for us to say let’s serve a couple more and lean away from a model that searches for a really high price point. 

How do you keep the creativity up when you’re remote and can’t brainstorm in one room?

Truthfully, it comes down to your people and investing in them. We hire people who are so thoughtful and considerate, and out of that comes empathy for wanting to do better and wanting to learn more. 

Structurally, especially coming in as a marketing director, it was about how I empower my team with smart data and then time and white space to go research and learn so they can make decisions on their own. Communication is part of that as well. 

How do you facilitate communication on a remote team?

Slack! Slack threads are key. We use it to asynchronously chart big thoughts and concerns. We also use Dropbox Paper and Dropbox Files. Then, it’s not a tool, but we have guidelines on how we communicate - what goes where, how, when. 

When you’re thoughtful about that, you get that kind of inclusivity and cross communication that can get out of hand if you don’t set those guardrails. 

What are the most important guidelines people need to set for remote communication?

I think it’s necessary to know what communication goes where. At Buffer, we’re timezone agnostic, which has to be a choice you make as a company. With that, we’re intentional about communicating asynchronously to be inclusive of all time zones. 

Another thing I’ve learned is that you have to be intentional about how you want things to go - and if you are going to moderate or not moderate. At Buffer, we’ve seen the benefit from moderation, offering how we communicate in a positive way. Or this is how we use emojis. 

How did you get introduced to remote work? What made you choose to stay remote as you became a team leader?

I got my first foray into remote work when I was working at Zapier in 2016. I spent the year travelling around, which was an incredible experience. I’ve stayed remote since, started my own company and was remote from home. Then with Buffer I’ve always been remote. 

Remote work is truly something I think is here to say. Allowing life to be a priority over a commute. Letting people get two hours back in their day to say “this is my time.” For me, that’s opened up opportunities. I spent time in Japan. I spent time in South America and now I know a little Spanish. 

And staying is huge for parents as well. Perhaps 2016 is a trigger for me as we’re heading into an election. But we think of those boundaries between Coasties and rural areas. I live in Brooklyn, but I was raised in a small town in Indiana. There’s this dialogue about how these worlds are so different and how we don’t communicate. And one of the wonderful things about remote work is you’re not tied to where you are - you can reinvest in those communities. You can choose where you want to live. Boundaries set up by geography just aren’t there. 

What’s the biggest lesson you learned as an entrepreneur that helps with your role at Buffer?

For anyone in tech, there’s this comment that people can’t wait to start their own business. That they don’t want a boss. Or that they want freedom. I was totally this person. What I found working for myself is that you have many more bosses, more clients, more partners, more landlords… there’s always a moment where you’re collaborating and co-creating. 

Like the Bob Dylan song: You’re always going to have to serve somebody.

What’s your least favourite part of remote work - and how are you handling it?

I’m an extrovert. I love people. So it’s being intentional about getting out with friends after work or joining a coworking space that is easy to walk to. 

What’s one thing you wish every remote marketer knew?

There’s this dialogue often in an aggressive growth space that’s about having to do something and push through and force it to come off as confident. That you can’t include emojis. Or no one likes smileys. You have to let people know where you’re at - lean into emoticons to help express emotion when you don’t have the words.

What resources do you turn to for professional development and learning?

I think remote is actually better for professional development. When things are remote and you’re doing it right, there’s a lot of documentation. For example, at Zapier I was trying to figure out if this launch we did had any impact on engagement and adoption. I went really deep in the data with before and after analysis. I could just pop in and spend a little extra time because I was curious reading and learning from other teams. 

For anyone who’s curious or ambitious, those resources are there so you can asynchronously learn and absorb. There’s a lot of passive resources for you learn from your coworkers. 

Amazing, thank you for your insights!

You can get in touch with Ashley via email or on Twitter. 

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about running a business remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Respond to this email (or send me one) Or just read on…

First: Welcome to all the new subscribers - we’re officially over 650! If you know someone interested in running a business remotely, I’d be grateful if you forwarded them this newsletter.

Today: We’re talking about remote community building with an entrepreneur who’s built a multi-thousand person virtual freelancer community.

Bobbie Racette has been helping businesses remotely for years, but never as much as during the COVID pandemic. Her business, The Virtual Gurus, connects businesses all over the world with highly-trained, highly-educated freelancers and virtual assistants for everything from blogging and social media to data entry and planning calendars. Now, she’s further innovating in the space with askBetty, a Slack app where entrepreneurs can work with freelancers on a task-by-task basis.  

As an entrepreneur, Bobbie has built a strong community of over 6,000 freelancers in the Virtual Gurus network. The way she built - and sustains - that community is a lesson for anyone leading remote marketing, community, or sales teams. 

In this episode, Bobbie shared what she focuses on when it comes to community building remotely: education, infrastructure, and the human touch.

The power of education

→ A core value proposition of Virtual Gurus is providing highly-trained remote workers for companies. To help ensure the success of gurus on the platform (thus making them more money), the company hired an onboarding team to explicitly work with new gurus to get them up to speed and matched with clients. 

→ Another way that Bobbie and the team ensure their community is poised for success is to offer them direct education. The Virtual Gurus Academy offers courses - available to anyone, not just guru community members - on specific skills that Virtual Gurus clients are willing to pay for. 

Communities need infrastructure

→ Whether digital or physical, every community needs the infrastructure to succeed. Current team solutions were helpful, but frequently didn’t allow for the kind of community building that Bobbie wanted. 

→ While it’s not visible on the front-end, the Virtual Gurus team built a thriving community platform where gurus can connect to help each other with work assignments, mentor each other, and build their networks. 

The human touch

→ Every marketplace has at least two sides, and Virtual Gurus is no different. So they have a customer success team explicitly focused on providing the human touch to both clients and the gurus working to support them. That way, no one feels that they are only working with a machine - and there’s always a direct connection to the core operations team. 

→ Part of Bobbie’s mission is to use technology and business as a driving force for good in the world. This was one of the reasons behind founding the Academy, but also drives Bobbie’s further community building efforts. Specifically, she’s working with various underserved and often-ignored communities, including the LGBTQ+ and Indigenous communities in Canada, to teach them the skills necessary to launch their own freelance business, whether with Virtual Gurus or not. 

The final word

“The main thing [about remote work] is to trust your team. You trust them in the office. You’re not sitting beside them all the time. You just have to have that same trust being at home.”

I’d be grateful if you shared this post with anyone you know interested in remote work and running a business remotely

Remotely Inclined Chats with Bobbie Racette, Founder of Virtual Gurus

Transcript edited for brevity and clarity.

Stefan: Welcome, Bobbie! Can you share a bit about yourself and Virtual Gurus?

Bobbie: Yes! Virtual Gurus is a virtual assistant platform - a marketplace where we provide work to virtual assistants, freelancers, and remote workers. On the flip side, we provide services to businesses and entrepreneurs of all sizes. 

We match based on algorithms - we have all the virtual assistants in a database and you can select which assistant might be better for you. Our assistants are all in Canada, but work with clients all over the world in Singapore, the UK, Australia, and all over the US and Canada. 

We’re also working on a Slack app called askBetty. Since so many entrepreneurs don’t need full-time virtual assistants, we’re building askBetty as a by-the-task app. 

You gave away a lot of free services in response to COVID. How did that impact your business?

I turned it into thinking that panicking isn’t going to get me anywhere. Instead, what can I do to help people? 

A few of our clients were quitting and pausing because they were stressed out and not sure what was going to happen. It was all unknown at that point. So we decided to launch a People over Profit program and decided to kick it off with 110 startups across Canada, giving them free service from us. 

We took a financial hit from that, but everything worked out because most of the clients ended up staying on because they liked the service. We didn’t even need to do any marketing because it was marketing itself from work of mouth. That resulted in us having 66% month-over-month growth. 

How do you manage a growing remote team - now in the hundreds - while still maintaining quality?

One of the things we’ve worked on internally is the management side. There are a lot of moving parts as you grow. So we hired a full-time client success team to manage the quality of the work. We also have an onboarding team and a Virtual Gurus Academy to train virtual assistants, which is available to everyone. We try to help VAs and freelancers to scale up. 

We also have a whole community on the backend. People don’t see this, but the community can talk, support each other, and help each other with jobs - it’s all remote workers helping each other. 

I love the focus on community. How do you balance synchronous vs asynchronous work with your growing team?

We’re trying to figure out exactly what we’re doing as far as making sure, logistically, how our virtual assistants can service multiple clients at once and how they do it. So we have a few staff in a small coworking space, mainly our operations staff, and everyone else. Most of our upper management is at home. 

We also train our contractors on the importance of time management and balance. We work with them on prioritizing. That’s helped us as well with our own skills. 

With the Academy, people can take courses anywhere. With askBetty, it will be everyone with a Slack account. 

Hybrid remote versus all-remote: what’s your preference?

So I’m at home. Our COO is at the office because she just got back from a holiday. We have full time staff for operations in an office. Sometimes it’s important to be in the same room. Upper management doesn’t necessarily need to be there, but our CSMs found they feel like more of a team when together and more able to focus on the client success side of it. 

I’d love to get rid of the added expense of a coworking space, but the CSMs love it there. We also give our VA’s the same option - if they want to go into coworking spaces local to them, we’d be happy to build partnerships with coworking spaces they can use. 

But we don’t need a full office. We’re also growing and hiring five more people, but still won’t get an office - they will be fully-remote workers. 

What’s your advice for leaders making the hybrid vs all-remote choice for their teams?

The first thing I thought when COVID hit was that it would be a game changer. A lot of people came to the realization that working from home is probably better - you can be just as, if not more, productive from home. And I know expense-wise, it’s better for my company. 

But we had the platform for it. It was an easy transition for us. We ended up changing the transition to make sure we could help all the businesses that use our service, and we were able to reach out and give them advice on how to change everything. One of the things I’ve tried to tell people is that everything stays the same, you’re just not looking at their faces all day (other than zoom or something). 

Whether remote or not, everybody should know their core responsibilities and should still be able to perform those responsibilities. You just have to over-communicate and set expectations with staff and contractors. Then you should be able to work remotely. I think the main thing is to trust your team. You trust them in the office. You’re not sitting beside them all the time. You just have to have that same trust being at home. 

Amazing, thank you for your insights!

You can get in touch with Bobbie on Twitter and check out Virtual Gurus.

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Image courtesy Virtual Gurus

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about running a business remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Respond to this email (or send me one) Or just read on…

Joe Blair is a venture capitalist in Silicon Valley firm Cota Capital and host of the Epic Human Podcast, but before that he was an engineer turned entrepreneur. His first foray into the concept of remote work was when he invested in an air taxi service back in 2017, which caused him to think more consciously about where people could live and work. At the time, remote work was seen as an exciting new prospect, but potentially more hype than reality. COVID obviously changed things a bit. 

In this episode of Remotely Inclined Chats, Joe and I dig deep into how VCs are thinking about remote work, how the whole VC ecosystem has changed from in-person to remote, and how successfully fundraise remotely without “remote washing.”

From opportunity to reality

* When Joe first got into remote work back in 2017 / 2018, a lot of the conversation was how remote was a niche thing that had some potential. COVID forced everyone to try it, and now the conversation has shifted from potential to practicality. 

* The first Remote Work Expo that Joe hosted in 2019 had 35 attendees. The April 2020 edition had over 450. The questions focused on the right tools and management practices for remote work. 

* Even though many workers are looking forward to returning to office life when it’s safe to do so, Joe says that he’s seen a decade’s worth of acceleration in the remote work movement due to COVID. 

“Remote washing” is out, accurate categories are in

* With the rise of remote work came “remote washing” - slapping a “we help remote teams” logo on your business, similar to “greenwashing” when companies talk about helping the environment as a marketing tactic. 

* Joe said that most venture capitalists can see through remote washing, so it won’t help your odds of fundraising in this environment just by saying you work for remote teams. 

* Technologies that help remote teams often fall into one of four categories: horizontal solutions explicitly for remote teams, vertical solutions for a specific industry that includes remote workers, physical infrastructure to support remote work, and back office functions that support remote companies. You can build a successful company in any of these categories.

Building VC relationships remotely

* VCs are adjusting to the new reality of becoming remote workers, said Joe, and a new study found that 69% of VCs are giving all-remote deals the green-light. Joe’s VC firm, Cota Capital, just finalized its first all-remote deal, investing in medtech startup Proprio.

* If you want to fundraise remotely, you need to work on digital relationship building skills and focus on authentic reach outs. Whatever you do, don’t copy-paste a generic blast out to every VC you can find. 

* Warm intros are still the best bet, but if you can’t get one, then anchor your efforts in a genuine connection to what the VC is interested in personally. You’re far more likely to get a response if you’re talking to them about blogs they’ve written, podcasts they host, or other ideas they’ve put out into the world versus just talking about what their fund is doing in that particular moment. 

The final word

“I think we’ve accelerated this transition to remote work by at least a decade.”

I’d be so grateful if you shared this article with your colleagues and friends who are interested in remote work

Remotely Inclined Chats with venture capitalist Joe Blair

Transcript edited for brevity and clarity.

Stefan: Welcome, Joe! Can you share your journey with remote work?

Joe: Sure. To put it into context, I’m from the New York / Connecticut area. I was originally an engineer, turned entrepreneur, turned venture investor. I’ve been doing venture investing for the last seven years after graduating from Harvard Business School. 

I came to remote through my interest in mobility. About three and a half years ago I started getting interested in the future of aerial mobility, which led me to an investment in a company called Lilium, which is an on-demand electric air taxi company. It’s a new transportation paradigm where you can get from city to city in the air, on-demand like you would with Uber. 

I started thinking harder about if this new transportation dimension were to manifest, where would people live? I then started thinking about what if you don’t have to commute at all. 

Then I found myself in Wyoming at a round table discussion with the then governor. We were talking about mobility and he was asking how we bring San Francisco-based tech companies to Wyoming. I was in this beautiful log cabin style mansion, snow-capped peaks all around me, and I started thinking that it was one of the most beautiful places I’d ever been. I was struck by the irony that they were asking how to get people to live there, meanwhile in the back of my mind I’m thinking I would love to live here, so how can I figure out how to work remotely and live here? 

So I started thinking about it from first principles as an engineer. The internet exists. Remote conferencing exists. Cloud-based productivity tools exist. Why can’t people work remotely? It didn’t seem to me like there was a technology barrier. 

What barriers were holding people back? 

I put together a summit to explore this topic back in 2019. Remote Summit. It was a virtual conference - we had 35 people show up, and we powered it with Remo.co. 

We had some thought leaders, including Laurel Farrer from Distribute Consulting and the first head of remote at AngleList, and some of my VC friends showed up. And we talked about remote - I think the title at the time was about whether remote was hype or a huge opportunity. The context was all about that remote is happening, but is still kind of niche and a futuristic concept. It would probably take us 10 years to progress and there are probably a few dozen companies that have started innovating in this space. 

I remember thinking it would probably take a long time but maybe there are early investments to be made. And then COVID hit and the world flipped upside down. All of a sudden, these companies had to go fully remote. They were forced to do it. Then people realized they could get by. Maybe they needed different management styles, but there’s good arguments out there for if remote work is at parity with working in an office. I think it depends on management style. 

But if you look at the big picture of this Black Swan event for remote work, let’s say 2% of knowledge workers were working remotely pre-COVID. Now it’s about 80% to 90%. Then when things “go back to normal,” let’s say that number goes down to 20%. That’s still a 10x jump in a very short period of time. 

I think we’ve accelerated this transition to remote work by at least a decade. It’s been an extremely exciting time. You have announcements from companies like Coinbase, Twitter, Square, and Shopify, saying this is working for us and we’re going fully remote - at least an an option - in perpetuity. 

And it’s a huge shift in mindset of employers, because they are realizing that many employees really value remote work. They get to spend more time with family and friends, reduce time commuting, and live life on your schedule. 

What are you seeing in VC conversations about remote work now?

At the beginning of April, I had another conversation with Laurel Farrer, and we decided to do another summit. The conversation was around managing a team remotely - what tools are available. Many entrepreneurs had been working on these products for years and now they’re making their products available. So we did another Remote Startups Expo, about the tools, software, and platforms that are going to enable this transition to remote work. 

I think there’s excitement in the air. And an acknowledgement all around that the tools we have are not optimized for the needs of managers and employees alike. 

I tend to split the category of remote work into four different categories: 

* Horizontal collaboration tools like Tandem chat. 

* Vertical collaboration tools around a particular industry, like Pendo Health out of the UK that’s effectively Slack for medical professionals. 

* Physical infrastructure. Having some sort of location to go to whether it’s a home office or a third place. 

* Back office for things like hiring remote workers across the US and different countries. 

Entrepreneurs are taking advantage here in a good way. They’re providing solutions that are really needed. It feels like we’ve been talking about remote work for a long time but it’s really only been a couple months. We’re still at the very early stages of this game. 

How are VCs shifting to remote and assessing deals remotely? How do you avoid “remote washing”?

I think Brianne Kimmel makes a good point about remote washing. With any hot trend, you’re going to see this. Like greenwashing or what I called block-washing for blockchain.

Any good investor can see through that almost instantly. What I think the nuance here is that there are tools built specifically for remote teams and then there are tools that are horizontal by nature that are good for centralized and remote teams. 

There are legitimate businesses built in all those four categories I mentioned before that would not be considered remote washing. 

But VCs have a very old-school mentality. They want to meet in person. To shake hands. They say ideally people live in my zip code so I can visit their office. But I think that’s starting to change. 

Like in every other industry, VCs are coming to grips. The reality is it doesn’t matter if your company is in Santa Clara, New York City, or Hong Kong. I’m not going to be able to meet you in person any time soon. So what’s the difference? 

I’ll speak for Cota Capital, my firm. We just made our first remote investment a few weeks ago called Proprio, an exciting company out of Seattle, Washington.  We met them virtually, did all our diligence virtually, and couldn’t be more excited about the investment. 

VCs are challenging their own assumptions and are having to deal with this idea of becoming remote workers themselves. 

What’s your advice for a founder looking to fundraise remotely?

The hardest part is making that connection when you don’t have it already. So of course warm intros ar egreat, but those aren’t always accessible to everyone. So for the folks who don’t have warm intros or existing relationships, I advise people to read up on the investors that you find personally interesting. Go to their Twitter, Instagram, podcast, read their writing. Get a feel for what they are interested in. 

If you’re building something that fits their investment categories or things they get excited about, I would suggest reaching out directly in an authentic way, saying ‘hey, I read your article. I’m building something that I think you’ll find interesting in this category. 

I love to jump on the phone when people do that for me and I can tell they’ve actually read up on me and done some homework. It’s not always a fit, but I almost always get back to them. 

I don’t advise you just copy-paste your email and blast every VC in the valley and see who gets back to you. I don’t think that’s a wise approach. 

Amazing, thank you for your insights!

You can get in touch with Joe on: 

* Twitter: @joeblairvc and @epichumanpod

* Instagram: https://instagram.com/epichumanpodcast

* LinkedIn: https://www.linkedin.com/in/joealanblair/

* Website: https://www.epichumanpod.com/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about running a business remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Take this short survey. Or just read on…

As this audience is well aware, I’m pro-remote work. But I also don’t pretend it’s the solution to every work problem. In previous Remotely Inclined Chats episodes, I’ve talked with leaders about the ways that remote work isn’t perfect - or ways it’s downright annoying. For Floyd Marinescu at C4 Media, it was around creativity. For Andrew D’Souza at Clearbanc, it was about culture. 

Andre-Paul Johnson, the head of growth at Breaking Walls, is also pro-remote, and has been working remotely on and off for a decade. He even left Breaking Wall’s Montreal office to work remotely from Jamaica in 2019. He also writes a newsletter about remote growth. But despite its benefits, he noticed a key weak point in remote work, and that’s what we talked about on this edition of Remotely Inclined Chats. 

So whether you’re pro-remote and want to avoid a serious pitfall or hate remote work and want some schadenfreude, keep reading. 

A hybrid failure

→ As more companies announce their post-COVID remote plans, the vast majority are picking a hybrid arrangement. People often think that a hybrid arrangement with some in-office employees and some remote employees is the best of both worlds. In Andre-Paul’s experience, it could end up being the worst of both worlds instead. 

→ When companies have a hybrid approach to remote work, a two-tiered culture can appear. Suddenly, a lot of work gets done in the office that remote workers don’t see, and vice versa. In Andre-Paul’s experience, companies will often default to the culture and communication style of the founders and leaders. However, in-office employees benefit from good remote cultures while remote workers don’t benefit from in-office cultures. So there’s a disconnect if leadership or company founders work in offices. 

→ A key issue Andre-Paul noticed in his hybrid remote arrangement as asymmetric information flows. When you aren’t in the office, you don’t see what people are casually working on and you don’t have random ‘collisions.’ This isn’t as much of a problem in all-remote environments, since information flows become entirely virtual. It’s a significant challenge in hybrid environments since a lot of work happens that isn’t documented when you’re in an office, leaving out remote workers. 

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Seeing the trees and the forest

→ Addressing this challenge, for Andre-Paul, was a matter of communicating in the open as much as possible. When work is documented (a regular management best practice), then it doesn’t matter where the work happens. For this to be successful, leaders of hybrid teams have to default to virtual information sharing regardless of if work is done in an office or remotely. 

→ One solution that Andre-Paul particularly liked was Quora’s announcement about going “remote-first.” While employees can choose whether to work remotely or come into the office, all of Quora’s leadership must be remote. This will keep information and culture flows happening virtually, so both remote and in-office employees can plug into what’s going on.

→ Despite the negatives he experienced, Andre-Paul is still pro-remote. He sees the benefits of location freedom and building deep relationships with people online as well worth the nuisances of asymmetric information and broken information flows. 

The final word

“The thing with remote is that it’s not that different, in the end, from in-person management.”

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Remotely Inclined Chats with Andre-Paul Johnson

Transcript edited for brevity and clarity.

Stefan: Welcome, Andre-Paul! Tell me what you’re up to at Breaking Walls.

Andre-Paul: Breaking Walls is a video startup based in Montreal. I’m the head of growth on our small team. My job is to make sure whatever our devs are making ends up in people’s hands. That means a lot of things when you’ve got a small team - but it’s one of the cool parts of the job since you get to touch a lot of different aspects of the business. 

You went remote for love. What happened?

I’ve been working remotely on an off for the past 10 years on a wide variety of products, small teams, big teams, some hybrid, and some fully distributed. I’ve kind of run the gamut of what it’s like to work remotely. 

But this past year and a half has been extra unique. Our team is based out of Montreal. I used to live in Montreal. Then early 2019 I moved to Jamaica to be closer to my girlfriend, which is a pretty big move. A big part of that also meant a lot had to change with how I did my job because our team was co-located. We still had the office in Montreal. Working as the lone remote work on the team means you need to implement new processes and adapt how you work to the new situation. Luckily for me I was able to be in a job that allowed me to work remotely. 

I’ve always wanted to travel, so I took the plunge. About a year and a half of travelling later, I’m back in Canada but still working remotely - currently based out of Toronto with the team still in Montreal. And now, of course, everyone is remote due to COVID. That has added a new dynamic to the team. 

You said that hybrid remote work is like the worst of both worlds. Can you elaborate on that?

One of the big issues with hybrid remote work is managing the flow of information in a way that seems fair to everybody. Typically in a co-located team, or a team where everybody’s in the office, all the conversations happen in person: information exchange and information flows. 

It also all happens in the same place in fully distributed teams - all online, on Zoom, or in Slack. 

But when you have a team that has both people in an office and people working remotely, you end up with a fragmented flow of information. Oftentimes that flow of information happens wherever the leadership team is. I can tell you from experience that most leadership teams on hybrid teams end up in the office. So what that means is everyone in the office has access to those informal conversations with the leadership team. They’re privy to the decisions being made and the processes behind those decisions. Meetings happen in the office and remote colleagues aren’t included, or it’s an afterthought. 

People who work remotely on hybrid teams often end up feeling like second-class citizens within their own team. And that impacts not only team productivity but team morale. And the result is a lot of hybrid remote teams don’t perform up to the level that they could, and there are different ways to mitigate that. 

How did you mitigate these challenges?

Before jumping into what I did, one thing I read recently is what Quora did when they announced they were going hybrid remote-first. They’re allowing anybody to work remotely while keeping headquarters open to anyone who wants to come into the office. 

But what their CEO did that I think is brilliant is that he said the leadership team has to work remotely. As I mentioned, the information flow happens wherever the leadership team is. And in this case, leadership is remote. So the information flow would happen online. If people chose to work in the office, they still have to log into meetings through their own video chat and camera. 

Everybody ends up on equal footing and there’s nobody who is at an unfair advantage over other people in the company. And I think that is an extremely thoughtful way of implementing hybrid remote work in a way that actually works for your team and allows your team to remain productive and everybody feel valued. 

In terms of information flow stuff I’ve done with my team, we’ve been working on a lot of challenges that remote work has. I think a lot of remote managers will be able to relate with this. 

If you look at teams in an office, a lot of information flows relatively freely and you don’t even realize it. Informal conversations, team lunches, looking over at someone’s computer, or even just the physical space element of knowing someone is there if you need help. On top of that, you get body language, which is huge. It has its pitfalls, but a big advantage is that all the information flows freely and you can get away with a lack of structure and poorly defined processes since so much information is implicit. 

With a remote team, there’s basically no implicit information exchange. It’s harder to build trust and harder to empower teammates or get timely feedback. 

Here’s what we’ve done in our teams over the years to try to fix these issues: 

Over communicate: you have to communicate absolutely everything. Every decision that gets made. Every conversation. You have to make sure nothing is left to chance and make sure all information is conveyed explicitly so expectations are set properly. 

Document: it’s not only communicating, but making sure that everything gets documented. We have meeting logs for every meeting, which I know a lot of teams do in-office but it’s crucial to do that on remote teams. Same thing with decision logs, making sure that the reasoning behind every decision is documented. 

But even with communication and documentation, it’s harder to build trust with your team. It becomes a challenge because all communication ends up being very intentional and explicit. You lose those serendipitous moments of running into a colleague or going out for lunch or drinks. You have to plan for everything. 

On our team, we’ve started making room for non-work bonding. That means anything from a daily non-work video chats (or weekly) to talk about anything and get to know each other as people. We also have informal Slack channels or activities like book clubs or movie nights, or even team offsites (in non-COVID times). 

How do you balance getting work done and travelling?

A big part of that comes down to how your team structures work. I’m on a team that allows a lot of asynchronous work from the get-go. Our team has synchronous periods, like working at similar times, but people will come into the office at different times during the day or something like that. 

In remote teams, it’s a great opportunity to take this to the next level and try to find the right mix between synchronous and asynchronous work. 

That way, unless we had scheduled meetings or other scheduled activities, I’m free to make my own schedule. And that freedom makes a huge difference in team productivity. On the flip side, asynchronous work has its pitfalls as it’s harder to build trust or culture, but that’s where synchronous communication and synchronous work comes in. 

In my experience, 30% synchronous and 70% asynchronous time seems to work really well. We don’t measure exactly, but that’s approximately how we’ve done it with our team for the past couple years.

What’s your advice for a remote leader struggling to build information and trust systems remotely?

The thing with remote is that it’s not that different, in the end, from in-person management. Management always comes down to giving space to your best people to do their best work, and making sure you facilitate information flow within the team. 

So whatever you can do to improve that on your team, wherever your feel your team is lacking, it’s your job as a manager to facilitate a solution. A lot of the time that is the same in a remote setting as it is in a non-remote setting. It’s much harder than it sounds, but it’s as simple as that. 

Amazing, thank you for your insights!

You can get in touch with Andre-Paul on Twitter or on his newsletter.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter for people who run businesses remotely. If you’d like to sign up, you can do so here. Want to share your feedback? Take this short survey. Or just read on…

Aaron Orendorff learned to be a content marketer from the church. After getting a masters of divinity and working at a multisite church in Oregon, he learned the basics of storytelling, creating emotional connections with people, and public speaking and writing. He spun that experience into a content marketing agency called IconiContent, and he ran editorial at Shopify Plus remotely for years. 

Now a VP of Marketing and a partner at Common Thread Collective, a digital growth agency, Aaron helps ecommerce and direct-to-consumer companies tell their story with high quality content. 

In this Chat, Aaron shares how he cultivates close relationships remotely and how he builds a sense of emotional connection with people he’s never met in person. 

Creating emotional connections remotely

* When he joined Shopify, the company was vast majority in-office (this was years before Shopify’s major remote work announcement). 

* To build emotional connections with people, Aaron focused on being present in every digital channel possible.

* The tactics Aaron used are: 

* Starting in Slack, offering encouragement, praise, ideas, or comments in random channels throughout the company.

* Working on a multi-platform “stack,” he would then connect with people on LinkedIn that he talked to on Slack, sending them a DM with an interesting note. From there, he’d do the same thing via email. 

* As the conversation continued, he’d look for opportunities for a phone call, which meant he’d get access to their phone number. 

* Once he had their phone number, he’d send a text message to continue “showing up” in different ways. 

* This strategy, though, can get annoying for people. The key is to ensure that you’re truly helping the person, not just messaging them. Focus on their problems, issues, or questions. 

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Building a brand

* Aaron’s experience in the church taught him the power of being as present as possible. When he left the church and wanted to get into content marketing, he focused on guest posting in as many blogs as possible. 

* He would write anything he could about marketing principles to be published anywhere possible - he didn’t question whether it was a small or big publication. 

* Over time, publishing in small blogs and building a network helped him land major publications like Fast Company and Entrepreneur. This work became cumulative, helping him connect with people like Tommy Walker who connected him to his opportunity to join Shopify Plus. 

The final word

“There’s power in appearing more present and more real than you really are when you diversify your channel approach to interactions.”

Remotely Inclined Chats with Aaron Orendorff

Transcript edited for brevity and clarity.

Stefan: Welcome, Aaron! Let’s kick it off with what you’re up to at Common Thread Collective?

Aaron: I joined Common Thread Collective in February 2020 as the VP of Marketing. I’m also a partner. It’s a digital growth marketing agency for ecommerce and direct to consumer companies. I fell in love with it based on my past experience at Shopify Plus. 

You were in the ministry before getting into tech. What was that transition like?

I’d love to say it was a calculated move, but that’s a lie. I invested myself wholeheartedly in my first career. I went to seminary, got a masters in divinity, focused on public speaking and preaching, and worked at a multiside campus church in Portland, Oregon. Then I proceeded to burn that career down. I found myself unemployed and unemployable in rural southern Oregon. 

I’d cut my teeth, mentally speaking, writing in church ministry. Which is where I learned, as crass as it sounds, that it doesn’t matter if you’re right, it matters if you create an emotional connection with your audience. When you’re able to articulate their objections and point of view better than they can, they turn the corner and think maybe there is another way. And whether we’re talking bout conversion in the religious sense or in the way tech uses it, the principles are the same. 

All communication is sales - trying to get what’s in my heart and mind into someone else’s in a way that makes them say “yes”. 

So I found these incredibly transferable skills. I had a suspicion that was later confirmed that people were selling things on the internet, but couldn’t write or communicate well. So I jumped primarily into content marketing, and one thing led to another. Over the past 7 years. 

You mentioned that when you joined Shopify they weren’t as open to remote work as they are now. How did you build relationships remotely?

To get to Shopify, I wrote like a madman - anywhere and everywhere - for a 2-3 year period. I tried to get my name on as many sites as I possibly could, from niche marketing to mainstream like Business Insider, Fast Company, Entrepreneur, or Mashable. This was to essentially trick the world into thinking that I was somebody. And this is even more important today in a remote working environment. 

What I used to do is every time an article would go live, I would tag people who were featured in the article, asking them to check that I quoted them right. Not a big ask, just for a bit of curiosity. I cast these wide nets over and over again. And when you do that enough times - when you show up enough - one of them hits. That’s how I ended up connecting with one of the most influential people in my life, Tommy Walker, who was at the time the editor in chief of Shopify Plus. 

How did you cultivate relationships at Shopify remotely?

When I was writing in other publications, I was in multiple places and multiple sites. It creates this powerful social proof illusion in someone’s mind. It’s the same principle when it comes to remote working, especially when it comes to working in a company that’s predominantly in offices. 

What I found was the more involved I got in various Slack channels that I didn’t necessarily need to be a part of, the more I went out into those channels and started mixing it up in the comments. Then I would track down the people I really liked. I could find them on LinkedIn and send them a DM there. Or I’d find any excuse to relevantly email a few people at once or doing one on one. 

Then I always look for an opportunity to actually call somebody to get their phone number. Then try texting them. What I did was the same sort of experience where suddenly I was in all these different places. 

It feels more like I’m a real person with a much deeper relationship than I genuinely have simply because of that multiplicity of touch points. 

I then thought about other days to do this. And my new favorite one: Rather than writing out long instructions to my team or a long request to other people, I’ll do a Zoom recording / screenshot. That way my face is in the video and it’s 3-5 minutes long. 

Is there a limit to this? Does it ever get annoying for people?

It can. But at first, I would say 70% of my time was spent going out into their world. I would go to their channels, pay attention to what they are saying, and offer solutions to their problems as much as I can. 

The vast majority of the time I’m showing up, I’m not coming with a problem or a request. 

What’s your advice for newbie remote entrepreneurs?

There’s power in appearing more present and more real than you really are when you diversify your channel approach to interactions.

Perhaps the crowning achievement of this is building up to the sacred phone number. People are incredibly busy. So I am always building up to the excuse to ask for a phone number, not to call them, but to cross into the intimacy of text. I want it to be something where I intrude, but to cross that final barrier. So maybe I can possibly send them a phone recorded video of me celebrating something. It’s building this good will. 

Amazing, thank you for your insights!

You can get in touch with Aaron on Twitter or LinkedIn. 

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about remote work and remote entrepreneurship. If you’d like to sign up, you can do so here. Want to share your feedback? Take this short survey. Or just read on…

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: Wellness as a remote entrepreneur

* 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).

Amazing, thank you for your insights!

You can get in touch with Rebecca and Cailey in the Anika Works Facebook Community or on Twitter.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com

Hi,

Welcome to Remotely Inclined, a newsletter about remote work and remote entrepreneurship. If you’d like to sign up, you can do so here. Want to share your feedback? Take this short survey. Or just read on…

Shelly Spiegel’s company Fire Engine RED has been remote since she founded it in 2001. However, she didn’t feel she could talk about it for 10 years, worried that people would judge her company for not having an office space. Things changed in 2011 when Fire Engine RED won an award for its culture, noting they were the first remote company to win the award. Many people were shocked at the idea that a remote company could have a culture, let alone an award-winning one. 

Since 2011, Shelly has been more vocal about her all-remote company, writing a book on her methods called Fully Remote (formerly Virtual Possibility) and regularly commenting on the remote work world, including putting together one of the first directories of all-remote companies.

In particular, Shelly is proud of Fire Engine RED’s culture. The 80+ person company has an impressive retention rate and average tenure of 6.5 years, nearly 50% higher than the American average. 

In our chat, Shelly shared the tactical ways she builds culture remotely -- and explains how other companies can adopt the practices for themselves. 

Remote culture tactics

I believe our culture is why our team member retention rate is 92% and the average team member stays with us for 6.5 years. Some of our team members are even moving in 7-10 years. 

I always say that being CEO is not just being the Chief Executive Officer but also the Chief Entertainment Officer. You can’t just focus on growing the business, you have to focus on your team as well.

Transparency 

You name it, I’ll answer the question. 

I also have a feedback system where people can participate - they can ask me any question anonymously and I will respond within 24 hours, and share my response with the team. So people know I will answer the question and take action if need be. 

For example, we used to put people’s phone numbers on our website, and I got feedback that people were getting tons of spam calls. Within 24 hours, they were removed. 

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Fun 

Something else that’s popular is what we call Walking Wednesdays. It’s a phone call (totally voluntary) with a topic that has nothing to do with work. It could be about your first car or your first job’s team members, or something else. 

It’s optional, and people go for a walk wherever they are (our team stretches across 26 states and 5 countries). I kick it off then it just becomes a conversation. It works even though we have a team of 80 people -- I would say we have about an 80% of our team that joins each week. 

Recognition

We have a Slack channel called REDcognition, where we recognize members of our team for the good work they do for one another. We also post when good client feedback comes in because I want the team to know about it. 

Civic duty

Since we’re in an election year in the US, we set up another Slack channel called I Voted, where people can post messages with them voting or with the I Voted sticker on them, their pet, or their kids. 

We also joined an organization called Make Time To Vote, which is an initiative in the US where companies commit to letting employees vote on company time, so the time is respected and paid. That’s one of the reasons we started the I Voted channel, and it’s very popular. 

An aside: A big part of culture is music. For me, that’s country music (don’t judge). But I also like discovering new music, and I recently learned about Album Daily, a newsletter dedicated to helping you discover - or re-discover - great music.

If you’re a music lover, this newsletter is worth checking out.

Family and COVID

With more family members home than ever before, we’re in the process of putting together a company-wide talent show to showcase our team members’ talents and the talents of their family as well. 

Everyone’s excited because it’s not just the team, but also families. And for children especially. In fully remote companies, too, every day can be bring your pet to work day, so one of the things we’re doing with the younger children of our team members is having a pet show and tell call where they can introduce their pets to our team. 

The final word

“You can’t just focus on growing the business, you have to focus on your team as well.”

Remotely Inclined Chats with Shelly Spiegel

Transcript edited for brevity and clarity.

Stefan: Welcome, Shelly! Can you share what you’re working on and what Fire Engine RED does?

Shelly: Absolutely. I started Fire Engine RED in December 2001 and from day one we were a fully remote company. We’re coming up now on 20 years. 

We primarily serve colleges in the US and work with admissions offices helping them market their institutions to prospective students. On the technology side, we’ve developed a CRM product to help colleges manage their interactions with prospective students. So we’re a hybrid company - marketing and technology. 

How has it been growing a remote business in the education field?

Back in 2001 we were an anomaly being remote. We didn’t feel it was in our interest to share that we were remote with our prospective clients for the first 10 years. If people asked, we’d be honest, but we didn’t just talk about it. 

In 2011, we applied for an award through Inc Magazine as a top place to work that had a great culture and good values. I was thrilled were one of the 50 companies selected. And in fact we were the first fully remote company to be selected for this award. The judges were shocked that a fully remote company could have a culture. 

One of the reasons we went and stayed remote was the ability to hire top talent - and educators became impressed with the team we put together. I would always tell them we were able to do this because we’re fully remote, and thus they became more and more comfortable with that fact. 

Should people speak loudly about being remote now, or should they keep it silent?

They should very much talk about it. It’s a positive. It really is. It gives companies the ability to hire top talent.

And when COVID hit, it proved that further from a business perspective. 

My worlds collided. We had so many processes in place to work remotely that we could continue working without skipping a beat. And then I gave several webinars to colleges and admissions offices, specifically teaching them how to lead a remote team, since my clients found themselves in this position overnight. 

2020 has been the year of change. Now people realize things can change at any moment. 

Can you share what you’ve done to build such a strong culture remotely?

I believe our culture is why our team member retention rate is 92% and the average team member stays with us for 6.5 years. Some of our team members are even moving in 7-10 years. 

I always say that being CEO is not just being the Chief Executive Officer but also the Chief Entertainment Officer. You can’t just focus on growing the business, you have to focus on your team as well.

Transparency 

You name it, I’ll answer the question. 

I also have a feedback system where people can participate - they can ask me any question anonymously and I will respond within 24 hours, and share my response with the team. So people know I will answer the question and take action if need be. 

For example, we used to put people’s phone numbers on our website, and I got feedback that people were getting tons of spam calls. Within 24 hours, they were removed. 

Fun 

Something else that’s popular is what we call Walking Wednesdays. It’s a phone call (totally voluntary) with a topic that has nothing to do with work. It could be about your first car or your first job’s team members, or something else. 

It’s optional, and people go for a walk wherever they are (our team stretches across 26 states and 5 countries). I kick it off then it just becomes a conversation. It works even though we have a team of 80 people -- I would say we have about an 80% of our team that joins each week. 

Recognition

We have a Slack channel called REDcognition, where we recognize members of our team for the good work they do for one another. We also post when good client feedback comes in because I want the team to know about it. 

Civic duty

Since we’re in an election year in the US, we set up another Slack channel called I Voted, where people can post messages with them voting or with the I Voted sticker on them, their pet, or their kids. 

We also joined an organization called Make Time To Vote, which is an initiative in the US where companies commit to letting employees vote on company time, so the time is respected and paid. That’s one of the reasons we started the I Voted channel, and it’s very popular. 

Family and COVID

With more family members home than ever before, we’re in the process of putting together a company-wide talent show to showcase our team members’ talents and the talents of their family as well. 

Everyone’s excited because it’s not just the team, but also families. And for children especially. In fully remote companies, too, every day can be bring your pet to work day, so one of the things we’re doing with the younger children of our team members is having a pet show and tell call where they can introduce their pets to our team. 

What is your advice for a remote entrepreneur who is feeling in over their head?

Only hire people who share your values. 

You can have all the processes in place with the right clients, but it comes down to people. You just can’t focus enough on your people. 

Not everyone’s cut out to work remotely, and not everyone’s cut out to work for you. So you’ve got to define your values and find people who share those values. 

Amazing, thank you for your insights!

You can get in touch with Shelly on Twitter or LinkedIn.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit remotelyinclined.substack.com