The road to remote working success: an inside look at bootstrapping a startup

the road to success surfer

This short story about remote working was co-authored by Charlie Birch, Rachel McGehee, and Summer Weirich.

the road to success - starting a remote work startup Rebel and Connect

Our names are Charlie Birch, Rachel McGehee and Summer Weirich and we are the founders of Rebel + Connect, a startup that creates custom retreats for remote working companies and their employees.

Background on us. Why we are creating a remote working startup.

In February of 2016, I registered for an online business course program. Prior to making this decision, I had been struggling to build my coaching practice. I invested in a webinar training program that I hoped would be a game changer. I put in a tremendous amount of hours to build my funnel, design my webinar, and prepare for a flood of new clients. In addition to the money I invested to participate in that training, I also spent $300 on Facebook ads, hired someone to help me with social media, and purchased a webinar software.

When it came time for my webinar, I had only three guests: my buddy from college, my sister, and a woman I had connected with on LinkedIn. I was crushed.

For the whole week following this epic bomb, I laid on the couch at my boyfriend’s house eating junk food, intentionally checking out from the world around me.

I was brought back to life when my dad called and pitched an idea for a blues musicians’ traveling train tour from Philly to New Orleans and back again. This idea did not end up materializing, but the excitement lingered and made me curious.

Soon after, the online course program sent out our first pre-course bonus. Five minutes into the first PDF worksheet, I had a breakthrough.

My previous business sucked and would continue to suck because I hated it. It was the wrong business for me. I didn’t want to be a tour guide on a train as my father has suggested, but I was sick of relating to people through a purely digital platform like webinars. I wanted to co-create real life experiences with others.

The moment I admitted that to myself, I was hit with a flood of ideas and experienced intense clarity.

The integration of these ideas was the seed of the business concept that over the next seven months would blossom into Rebel + Connect.

This is our story (so far…)!

Why Rebel + Connect is a unique remote work startup and team.

I honestly don’t remember the specifics of when Charlie called me, I just remember that she said she had a business opportunity that she wanted to tell me about. I remember I had a great feeling about this right from the start. I have always wanted to be a co-owner of a business, but finding the right business and the right co-owner(s) is tough to say the least.

Charlie had been my roommate previously and I know that when she puts her mind to something, it happens. Though we are two very different humans, we are similar when it comes to ambition and completion – so I trusted she was on to something!

When Charlie told me that Rachel was the other potential business partner, I got very excited. I know Rachel is another amazing human who is ambitious as we are and has great ideas continuously come from her brain. I could hardly wait to meet with Charlie and Rachel on a Zoom call.


It was March, and out of the blue I get a text from Charlie Birch.

I hadn’t seen Charlie in almost 2 years. And the last time I had seen her was a complete chance encounter when I was visiting Boulder.

But that’s how things go when you’re connected to yourself and to others. Somehow the right people seem to pop up at just the right time. Now maybe to you it doesn’t seem like the “right” time, but when we let go of fear and doubt, the Universe has a way of delivering.

remote working startup - text screenshot

So back to that “out of the blue” text. It went like this:

My first thought?

Hear her out, Rachel. She’s a friend, so you at least gotta listen to what she has to say.

And my second thought?

Rachel, are you effing serious? There’s no way you can be part of anything else. You already have too much on your plate as it is.

Well, anyone that knows me knows I went with my gut and intuition and I scheduled a time to chat with Charlie.

When we finally got on the phone I had just finished a long day, was driving home in traffic, and I was not in the best mindset to be “pitched.”

By the time I pulled into my driveway, Charlie had piqued my interest slightly, but I still wasn’t sure. She mentioned that Summer was on her mind as a partner, and they were hopping on a video chat later that week.

I know Summer as someone who is just as busy as me (if not more!), with the ability to spread glitter regardless of her stress level. So if she was open to it, I had to hear more.

When I got on a Zoom chat with Charlie and Summer a week later, I realized that this girl had done her homework. Charlie was so serious about this “idea” and was bringing so much passion to it, that it already felt real. I had to be a part of it.

On March 11, 2016, all three of us hopped on our very first Zoom call.

Charlie gave a bomb-@$$ presentation that explained her idea to aid remote teams in creating and planning retreats. It was 47 slides long to be exact! The content highlighted social science, market research, the business model, an ideal client avatar, and each person’s internal roles.

She made it clear to us that we were the perfect business partners to help make this a huge success, but that regardless, she was doing this 110%. She told us that she didn’t need an answer right away, that we could give her an answer by the end of the week. However, Charlie had sold the $#!T out of us!

“I don’t need a week, I’m in 100%!” exclaimed Summer.

Rachel said, “Charlie, if this is where your brain is, I want to be in your brain!”

Raising Our Startup

Right from the start, it was clear that this was going to be an unconventional team. We knew we would never feel at home in a board room. Actively refusing to conform to the traditional cookie-cutter image of a business meeting has allowed for more fun and creativity than any of us could have ever imagined.

In person, our official meetings more closely resemble this:

remote working startup - rebel and connect team

When we aren’t able to be in the same location (99% of the time) you might expect to see something like this….

remote working startup - rebel and connect working

Within 10 days of forming our team, Rachel’s brain started to twitch when she was exposed to Summer and Charlie’s excessive texting habits. Her reaction was to make a three page google doc transcription:

remote working startup - rebel and connect work notes

It was painfully obvious that we needed to create a better system for internal communication. Summer introduced us to Slack and we never looked back!

Tracking projects and tasks for our team had Rachel approaching headless chicken status.

We needed a way to organize everything in one place! Charlie wanted a visual timeline and began researching different options. Trello won and became our project management solution.

Turns out Trello and Slack have built-in integrations! 😉

Since we are all friends first and business partners second, we had to get serious about how we would use our meeting time. The only way to avoid falling into the old habits of pure social interaction…

remote working startup - rebel and connect beer meeting

…was to create new norms of behavior that set the tone for productive and constructive meetings. Now we start and end every meeting with a three part ritual that draws upon:

  • a centering technique that Charlie learned from her mentor Mark Walsh.
  • an aspect of Twin Hearts Meditation practiced by Rachel called the A-bun-dance.
  • a style of verbal check-ins called ‘popcorn’ that is informed by the practice of lean speech. Charlie learned this technique while studying counseling psychology at Naropa University.

While the name of a business isn’t the most important thing, it isn’t insignificant either. We went on for about two or three weeks trying to come up with a name that resonated with all three of us. Some names that we played around with were Retreat Queens, Bolder Retreats, and Rebel Custom Retreats, but none of those seemed right.

Finally we found the perfect name, Rebel + Connect. We are all rebels who value connection.

Rebel + Connect is a call to action, and we are committed to, “Celebrating Human Connections in a Digital World!

As part of her online business course bonuses, Charlie had gained access to a course called Lift, which was designed to arm startups with the legal information they need to start a legit business.

After extensive research, we finally decided to register as a multi-member LLC in the state of Colorado.

We drafted, refined, and signed our operating agreement, identified, delegated, and drafted the specifics of the endless jobs descriptions, and then we got to work outlining the basic collaboration agreement we would present to our future collaborators.

Turns out that Charlie’s background in dance choreography and profession training, which requires a firm grasp of operation language, translated well into the rather tedious craft of contract writing.

If you want to celebrate with us, our business birthday is May 31, 2016!

Next, Summer took charge setting up a Google Voice account. She tried to connect all three of our phones to the Google Voice number, as a result the Google Voice line hijacked Rachel’s and Summer’s personal voicemails for a week, sending voicemails to the incorrect receiver, and misleading business prospects.

It took over a week to resolve. Thank goodness for Summer’s persistence.

In July, we decided we would lead our business to market with the launch of an exclusive subscription-based membership site.

Our utter lack of experience in this arena led us to believe that we could do everything manually (and for free) with Pinterest, Google Sites, and a Facebook group.

Looking back this seems laughably naive. We learned that creating a start to finish automated VIP Membership sales funnel with a corresponding members’ area required us to invest in, become proficient in, and skillfully integrate Instapage, Autopilot, Squarespace, SentryLogin, and Stripe. $1,000+ and countless hours later, we have transformed ourselves into tech-savvy online business Boss Babes!

remote working startup - rebel and connect tools used In August we explored the idea of saving money by switching from Zoom to Google Hangouts.

remote working startup - rebel and connect Google Hangouts

If you have ever been part of a remote team or even just a video conference, you know how important screen sharing and video quality can be.

remote working startup - rebel and connect live sessions

In a nutshell, Google Hangouts was $#!T.

We are Zoom-ers all the way! Zoom is worth the investment and still cheaper than an office! Zoom Room, baby!

At one point Rachel noticed that we had acquired an “Anonymous Hippo” as a fourth team member.

We had a good laugh until we realized that it could be a security breach. We discovered it was access from one of our personal email accounts and all triple checked our settings to ensure that only the three of us could view our Google Drive.

Being Millennials, we figured we could just use Venmo or CashApp to make our monthly internal contributions to our business bank account. Paying for checks and going to the branch seemed like a waste of time and money. Plus we wanted all our system to be location independent.

CashApp has a quicker turnaround time for transfers, so we gave that a try. Turns out that CashApp treats any transfers made to a business account as business transactions and charges the business a processing fee.

After figuring out why our bank account balance did not reflect the full amount of our intended contributions, Rachel went to war with CashApp explaining that yes we are a business, but that these transactions were not business exchanges. She insisted that we were not going to stand for CashApp taking a percentage of money exchanged internally when no revenue had been generated. They fought back, but Rachel won!

remote working startup - rebel and connect emails

We now use Venmo to make our monthly internal contributions.

Our ideal workplace is everywhere, nowhere, and wherever the F@$K we want!

Summer was road-tripping from Albany, NY to Denver, CO, using her phone as a hotspot to access Zoom and attend meetings. Leading up to one meeting in particular, Summer was camping in Yellowstone National Park.

When we joined the Zoom Room and started our meeting ritual: centering, A-bun-dance, and ‘popcorn’, Summer said “adrenaline” and “pain.”
Whenever there are negative emotions or experiences reported during these check-ins, we make sure to give that team member time to ‘unpack.’

Charlie and Rachel soon learned that Summer had chopped off the end of her thumb with a hatchet only 30 minutes prior to the meeting! Summer’s best friend, Kyle, bandaged up her thumb, our team held a two-and-a-half hour meeting, then Summer left to go get a tetanus shot.

remote working startup - rebel and connect hangout 2

About a month later, shortly before another significant meeting, Summer was thrown a yet another curveball, slipping on a wet floor in Chicago, injuring her ankle.

Hoping she could still make it to the meeting, she reported that she would be hopping to the pharmacy to purchase an ace bandage, hopping to the Apple store to buy a charger (she had left hers in Colorado), and would be with us shortly. However, Charlie insisted that Summer go to the hospital. Good thing Summer took Charlie’s advice, she had a broken fibula.

remote working startup - rebel and connect broken foot

We all agree that communication is key. Regardless, nobody is perfect, and misunderstandings are bound to happen.

After seven months without any significant co-founder conflict, which is pretty good for a group of three headstrong women, we had our first big blow out.

During a conversation about social media best practices, words were misunderstood, things escalated quickly, and two team members felt compelled to leave the meeting.

While it may be much easier to “walk out” of a digital Zoom Room, it is not the desired practice for the success of a team or retaining friendships. Eventually everyone returned, conflicts were mediated, and the meeting resumed.

Growing with Gratitude

Anyone who tells you they are a self-made anything is full of it- it takes a tribe to build and grow a startup.

In addition to our amazing life partners (Andrew, Anthony, and Strueber) and our extended support systems, we are extremely fortunate to have lawyers in all of our families. The amount of $$$ we saved on legal fees paired with the confidence we have in our operation is significant. There is no other way we could have accessed this same caliber of legal advice. A huge shout out to Debby Gardner, Clark McGehee, and Geoff Weirich.

Our decision to build our business on a foundation of collaboration also led us to connect with our first formal collaborators: Shannon Townsend, Ed Harrold, and Alicia Patterson. We are so excited to play with you and show the world that collaboration by far supersedes competition. Building our provider network is a foundational part of the work we do. We plan to grow this network as big as we possibly can in order to make it as easy as possible for remote leaders to access vetted high-quality resources for success in designing their custom retreats.

Finally, we have been on the receiving end of some outrageously generous offers from other entrepreneurs including but not limited to:

Khia Banks of Core Happiness for gifting us 4 coaching sessions allowing us to gain serious brand clarity!!! You are a rockstar and we couldn’t have done it without you!

Aaron Tarlini of Altitude Designs for hanging in there with us as we figured out all the OCD details of our perfect logo, and for a very reasonable price we might add!

Lisette Sutherland who took a chance on an unknown startup and invited Charlie to be a guest on her show, Collaboration Superpowers Podcast.

Arne Giske of Giske Business and the Millennial Entrepreneur Podcast. Thanks for taking the time to connect with us, welcoming us into your amazing community, and trusting us with your valued connections.

Scott Doucet of Podcasters Bay and Xavi Umeh of Brickred Studios. Thanks for taking the time to talk with us about our plans for Rebel + Connect Radio, and more importantly for being bad@$$ humans worth knowing.

Lois Wyant of JFT Marketing for having Summer on her show!

Jeff Lavin of Wi-Me Snowboards and Get Awesome for taking the time to meet with us and trusting us with your connections.

Daniel Ekker of Wi-Me Snowboards. For your amazing offer to help us take things to the next level. We are blown away by your generosity!!

Last but not least, thanks so much to Matt Gottesman and Case Kenny of Maker’s & Moguls for keeping it real and inviting us to participate in this amazing The Road To Success blog series!

Our goals for the next two months.

Great question!! We have our sights set high. Don’t miss our next three articles in The Road To Remote Team Success: A Raw Inside Look at Bootstrapping a Fully Distributed Startup series for PRSUIT. Over the next two months, we will be:

  • Producing fresh, original, free content on our blog, podcast, and webinar feeds
  • Landing our first couple of high end clients
  • Growing our VIP community to 100+ members (learn more)
  • Expanding our provider network by formalizing numerous collaborations with other coaching and training, travel management, and event planning people (collaborate with us)
  • Planning, enjoying and broadcasting our first official internal retreat (follow our Rebel + Connect Facebook page to tune in)
  • Researching our first annual event (tag us in your picture at @RebelandConnect on IG to let us know where you would go and what you would do #HereRC)
  • Seeking out opportunities to add value for other peoples’ tribes with guest blogs, podcast interviews, virtual trainings, and much more.

This road is extending beyond the horizon. Join us on our wild adventures complete with obstacles and celebrations by subscribing to our blog, Stories From The Road… and our podcast, Rebel + Connect Radio!!


Written by Rebel and Connect

At Rebel and Connect, we work with leaders of remote team empowering them to use retreats as a strategic tool to enhance worker experience and company culture. Rebel + Connect is a Colorado based company owned and operated by Charlie Birch, Rachel McGehee, and Summer Weirich. We operate remotely and service clients from all over the globe. For more about our mission follow us on Instagram, Twitter, connect with us on LinkedIn by clicking on our names above and checking out our LinkedIn Pulse articles. Email us directly at Free Download: Top 15 Things to Consider When Planning a Company Retreat

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