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Chelsea Clarke of HerPaperRoute: 5 Things You Need To Know To Successfully Run a Live Virtual Event

Ensure the speakers will attend live, while their session is live streaming.

As soon as you have your event schedule finalized, let your speakers know what day and time their recording will be live streaming. Then, personally invite each speaker to attend at their live stream time. This way, they can engage in the chat box with attendees, answer questions and provide a human touch in real-time, to compliment their pre-recorded session.

As a part of our series about “5 Things You Need To Know To Successfully Run a Live Virtual Event”, I had the pleasure of interviewing Chelsea Clarke.

Chelsea Clarke is a business strategist, investor, business broker and the founder of entrepreneurship blog, podcast and school HerPaperRoute™. Her specialties are blog monetization and website investing. Chelsea developed the Paper Route Profit Model™ a system for monetizing and scaling content, which she teaches at HerPaperRoute Academy. She has grown her company to over half a million dollars in less than three years. In 2019 Chelsea launched the Blogs For Sale brokerage, where she helps investors and content creators buy and sell niche online businesses, blogs and media properties.

Although she has a BA in Media, Chelsea believes you do not need a fancy degree to create a successful business in this day and age. Through her work teaching marketing and business growth-hacking strategies, she has helped a community of 200,000+ entrepreneurs increase their financial fitness and make more paper.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”?

I grew up in a creative family with an artist mom who always had a different creative project on the go, from painting wild murals to welding furniture in our backyard. My grandfather was a political cartoonist with a wit like no other, whose political cartoons were published in a regular column in McLeans magazine and the Vancouver Sun. As a kid, I admired how he was able to work from the comfort of home doing something creative that he enjoyed. I loved drawing and writing, and I enjoyed any school project that allowed me to add some creative flair to it.

I was also very interested in money, and from a very young age I would have yard sales, and sell cans of soda from my bike on the beach. I clearly remember when I was in grade 3, another class was having a bake sale. I had about $6 in my backpack, which can buy a lot of 5c cookies. So I went and bought everything they had. I then took the cookies, laid them out on a paper towel on the other side of the school and sold them to kids for $1 each. I thought I was so clever. But my mom didn’t agree, and made me give my profits back to the school. However, this was probably my first taste of entrepreneurship, and I became obsessed.

As I grew up, I became very interested in the strategy that goes into building a business, and I was constantly finding creative ways to make money. I started a blog as a hobby in University while studying digital marketing, and eventually I found content monetization to be my #1 passion, as it combined everything I felt lit up by: marketing strategy, money, tech and creativity.

Can you tell us the story of what led you to this particular career path?

In 2016 I was working a corporate marketing job at a business brokerage by day. My job was to build and maintain websites, organize marketing projects, and design things in Photoshop. I was doing the job of 3 separate professions, for one measly $30k paycheque. By night I was bartending in a busy live music venue. I was also 8 months pregnant! I knew that I had to figure something out before the baby arrived.

Now, I had always had a blog as a hobby, but until then, I had never thought of it as a business. That all changed one night in early 2017, when I was feeling completely lost and unsure of myself. I stared up at the ceiling, exhausted, holding my newborn, and admitted to the universe that I needed some direction. The very next day, while scrolling online, I came across an ad for a virtual summit for bloggers and online course creators. I signed up and binged the entire event. I soaked in every bit of information that I could, and by the end of the summit, I had my first online course plotted out, and a monetization plan for my blog. That virtual event changed my life! Within 6 months I was earning more than enough to replace my employment income, and I found my place where I am now.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was fresh out of high school, I launched a business drop shipping T-shirts from China online. I set up a website, put the images of the shirts up on the site, accepted orders from customers, and then ordered the shirt from the supplier on ALiExpress. I thought I had figured out the game of life! Except I totally missed the whole point of drop shipping, and didn’t drop ship a thing. You see, at the point where you order the T-shirt from AliExpress, you are supposed to put your customer’s address as the shipping address, so the supplier can send the T-shirt directly to your customer. But for my first few months in business, this didn’t dawn on me. I was putting my own address down, waiting for the shirt to arrive at my house, and then repacking and shipping it to the customer, which costs a lot and takes months!

When I finally put it together that I should just cut out the step of shipping it to myself, and instead have the supplier ship it right to my customer, it all made sense. So that was a silly newbie mistake and a good learning experience.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

“Superfans” by Pat Flynn is a recent book which has been inspiring me this past year. He has a very genuine take on his role as an influential person in this industry which I very much admire. There is a part in the book where he is talking about why it’s so important to respond to every email.

He compares someone not replying to an email being no different than if someone walked up to you at a conference, held out their hand to shake yours, and you just turned and walked away, leaving them hanging. How awful that would feel for that person who was probably your fan. Since the inception of my business many years ago, and to this day, I have always personally responded to every email I receive, as I believe it’s very important to ensure my audience knows they are appreciated. So I really liked the analogy Pat mentioned with the missed handshake, because it really is so true.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

You will be defined not just by what you achieve, but by how you survive.”―Sheryl Sandberg

Growing up in a low-income single parent home, we didn’t have much money, that’s for sure. When at 17 I wanted to go to University, I knew my weekend dish washing job wasn’t going to foot the tuition bill. My resourceful mom found just about every scholarship fund that existed in my Province, and encouraged me to write to every one of them. I literally wrote for my life so that I could have an education, and it paid off. I was able to land scholarships based on creative merit and financial need, which covered my first 3 years of University. But of course, this didn’t cover food, rent or anything else! My mom taught me perseverance and inspired the all-in work ethic that would benefit me later in life as an entrepreneur. I spent my 20s finding creative ways to make money on the side of my restaurant job and classes. For years, it was a struggle, with many setbacks along the way. But it was also a superb exercise in learning how to take difficult circumstances and make a positive outcome.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, can you tell us a bit about your experience organizing events in general?

Before I was an entrepreneur, I worked in marketing and events planning for nightclubs. I was able to let my creativity run wild and dream up fun theme parties for bars around Vancouver. And then I would strategize with my promotions team on how to sell tickets to the events. Usually we had about one week to plan the event, and one week to sell out the club. So I was able to hone my skills with events marketing efficiently under pressure. This certainly helped me later on, when I launched my company and started planning online events to promote it.

Over the years since, I have facilitated a number of virtual events such as giveaways, webinars, and group coaching masterminds. However, in 2020 I decided to take on something ambitious, and host a 5-day live virtual summit.

Can you tell us a bit about your experience organizing live virtual events? Can you share any interesting stories about them?

I debuted the Brave At Business summit, a profit planning summit, in December 2020. The event featured 40 workshops, interviews and presentations with 35 speakers. I live streamed the mix of pre-recorded and live sessions each day. This way, attendees could watch each session together, on the same page, and chat with the speakers, myself and each other in real time.

Although I had experience hosting live webinars in the past, this 5-day live virtual summit was my first time live streaming for several hours at a time. And although I was prepared as much as I could have been, you are never really sure if everything will run smoothly, until you hit ‘Go Live’ and hope for the best.

But when you accept that fact, and trust in your abilities, great things can happen. My summit went really well, and attendees had a great time. The summit earned $58,075 USD in the end, and helped add 4,000 new people to my email list.

In your opinion, what is an example of a company that has done a fantastic job creating live virtual events? What specifically impresses you? What can one do to replicate that?

Elizabeth Stapleton hosts the Blogger Breakthrough summit, and she does a really great job in organizing it all. I had the opportunity to speak at her event in 2020 and will be again in 2021. I really admire how organized she is. She puts together a massive speaker resource kit that is packed with everything the speakers need to be prepared for the event. As we know, hosting a virtual event is a big job. Virtual summit hosts should be prepared to manage anything and everything. But if you give your speakers as many resources as possible, you can ensure that they will help take some of the promotion work off of your shoulders. So make it easy for them with swipe copy, templates, graphics, and as much information about the event as you can arm then with.

What are the common mistakes you have seen people make when they try to run a live virtual event? What can be done to avoid those errors?

It can be tempting once you decide you want to host a live event, to hit the ground running and launch as soon as you can. But I would really advise you to take your time and allow yourself several months for planning. There are many, many moving parts involved with hosting a virtual summit and it’s not something you want to rush.

Another mistake I have seen summit hosts make, is they get all wrapped up in the planning and behind-the-scenes production stage that they forget to be a host. As a summit host you are the face of the entire event, and you need to look at your role on camera like you would as if you were hosting a TV talk show. Oprah wouldn’t come to the interview looking disheveled and she wouldn’t let the audience know how exhausted she is from working. Even if you are exhausted from all the pre-summit planning, don’t let it show. Your attendees want to see a fun, happy, professional and gracious host who makes them feel welcome. Not a frustrated, frazzled mess who makes them feel uncomfortable!

So think of your summit hosting performance as if you were a professional actor hired to do it. Smile, sit up straight, let your personality shine through, and of course, dress the part. Above all, make your speakers and attendees feel welcome and appreciated. Your happy manner will go a long way. This is showbiz, baby!

Which virtual platform have you found to be most effective to be able to bring everyone together virtually?

There are certainly a lot of options on the market nowadays, for virtual events. For my live broadcast, I actually used my own website which I built on WordPress, and used Vimeo Livestream Studio to livestream the sessions to an embedded player on my website. Everyone came to the live page on my website to watch the show, and chat live in the comments.

I then brought everyone over to Zoom for our networking parties, utilizing Zoom’s breakout room feature to split attendees into smaller groups so they could talk to one another in private rooms.

The combination of Vimeo and Zoom made for a smooth production, tech-wise. And then having the broadcast appear on the event website made for a seamless experience for attendees.

Are there any essential tools or software that you think an event organizer needs to know about?

In addition to Vimeo, Zoom and WordPress, I would also recommend using a good audio transcription tool so that you can add closed captions to your videos so they are accessible for the hearing impared. is perfect for this, it transcribes your mp3 audio files to text, which you can edit and export to an SRT file, to add to your videos. And the best part? It costs less than $10 a month!

Ok. Thank you for all that. Here is the main question of our discussion. An in-person event can have a certain electric energy. How do you create an engaging and memorable event when everyone is separated and in their own homes? What are the “Five Things You Need To Know To Successfully Run a Live Virtual Event” and why? (Please share a story or example for each.)

In-person events absolutely have the excitement of parties where you can network with other attendees and schmooze with speakers. They have the buzz of seeing your favorite speaker present live in the room with you, and the fun of walking up to sponsor booths to chat with brand reps and learn about cool products. But there is no reason why you can’t bring all of those experiences to your attendees, virtually!

Here are five ways that I was able to bring the excitement of an in-person event to attendees of my virtual profit planning summit, Brave At Business.

1. Ensure the speakers will attend live, while their session is live streaming.

As soon as you have your event schedule finalized, let your speakers know what day and time their recording will be live streaming. Then, personally invite each speaker to attend at their live stream time. This way, they can engage in the chat box with attendees, answer questions and provide a human touch in real-time, to compliment their pre-recorded session.

This gives the attendees a world-class experience. When the speaker is there live in the chat, it makes attendees feel that your event really is special, and that the speakers and organizers really do care.

But it is also a great networking opportunity for the speaker. Many attendees will have questions for them about their presentation and about their business. It is a great way to make connections and bond with potential new clients, in a fun setting.

When I hosted my summit, I noticed a big difference in attendee engagement, watch time and attendance between the sessions where the speaker was there, and the ones where the speaker was not. The sessions people enjoyed the most were the ones where the speaker was there in the chat box alongside them!

I also extended this invitation to my event sponsors, so they too could attend live while their sponsored sessions were broadcasting and participate in the chat box. All of the sponsors seemed to really enjoy this interactive opportunity to engage with attendees. It was essentially the virtual equivalent of attendees being able to walk up to their exhibit hall booth and talk about their products.

2. Embrace virtual networking parties & breakout sessions.

Ask anyone what the most fun part of any in-person event is, and most will say the networking parties. The after parties provide a much-needed break from a day of presentations. Being able to break out and network with other like-minded people is a major perk of live events. And who wouldn’t love the chance to schmooze with their favorite speaker over a martini?

But those days of schmoozing in large groups are over. At least for the social-distancing near future. But, virtual events still allow for networking parties — no masks required.

When I hosted the Brave At Business summit, I made sure to include a number of sessions that encouraged real social interaction and networking. I used Zoom to host a group networking party, where attendees all jumped into a live call. I separated them into smaller groups, in private ‘breakout rooms’ where they could chat and network amongst one another. After 15 minutes, I mixed up the groups and everyone had a new group of people to socialize with. It was a lot of fun.

Another way to encourage the feeling of togetherness is by hosting co-working sessions. A co-working session is where attendees join a group Zoom call, they each choose or are given a specific task to work on, and for the duration of the call everyone works on their individual task, silently, together.

We also used Zoom to host our live expert panel. For that, three speakers and myself met in a Zoom and then I livestreamed our discussion to a page on my website, where attendees were watching and interacting in the chatbox. They could ask the speakers questions and be a part of the discussion in real-time.

For attendees of any virtual event, it can feel overwhelming and draining if the sessions go on and on. There needs to be some breakout sessions where the attendees have a chance to participate. So I would ask yourself, how can you get creative and give your attendees an incredible experience, where they are part of the dialogue?

3. Keep the party going in a Facebook group.

After a day of watching your speakers share their wisdom, your attendees will likely be feeling inspired, motivated, and wanting more. Just because the day’s live stream has ended until tomorrow, doesn’t mean your event should hit the pause button.

Create a pop-up Facebook group (or just use a Facebook group you already have for your business), and make it the social portal for your event. This will allow attendees to mingle with each other 24/7, share feedback about the sessions, and feel a sense of community around your event. It’s also a great way for you as the host to form a closer connection with your attendees (who may very well become your future clients).

Make sure your speakers are all members of the group before the kickoff so that attendees can tag them in posts to ask questions or give praise about their presentations.

4. Have a virtual DJ play music between sessions.

If you are wanting to create a unique, memorable virtual event that will be sure to have people talking, get a DJ! With the right setlist, you will be able to keep attendee energy up throughout the day.

Truthfully, hiring a DJ to play music at your online event is not as tricky as it may sound. All you really need to do is ask around if anyone can recommend a great DJ, or just poke around on Soundcloud. With so many bars and nightclubs closed this year due to COVID restrictions, many DJs are available and in need of a gig. Then, you simply send him/her an email with information about your event, ask if they would be available to send you a video of themselves playing music, and include your pay or ask for their rates. Then when they send you the video, you livestream it at any point in the event you like.

Our DJ really brought the fun vibes and kept people dancing at their computers.

5. Offer giveaways.

Many in-person events will have some sort of game or scavenger hunt for attendees to play. A game encourages people to participate in the event, attend presentations, and interact with sponsored content. I would highly recommend having a game of Bingo at your next virtual event! Instead of numbers on each square, make it a task the attendee needs to complete such as “Attend 5 sessions live” “Follow us on Instagram” “Leave us a review” and so on.

Have everyone post their completed Bingo cards in a dedicated thread in your Facebook group and watch your engagement soar!

Let’s imagine that someone reading this interview has an idea for a live virtual event that they would like to develop. What are the first few steps that you would recommend that they take?

If you are thinking of hosting your own virtual event, I would first highly recommend that you allow yourself at least three months of planning, before the event kickoff. 90 days may seem like a long time for preparation, but believe me, you will be surprised just how many things you will need to do in that time.

The first step would be to come up with your event’s topic. Be as niched-down and specific as you can, so you know exactly what your event will be about and the specific thing it will help people learn.

No one likes a general anything-goes business summit with 50 speakers presenting on 1,000 random topics about anything and everything. To help you with this, think about what the transformation will be, that you intend to give your attendees. What will they walk away with after attending your event?

Then, seek out speakers who are experts in that topic, and who can provide value towards that transformation. They don’t all have to be big league super stars either! Including lesser-known or newer speakers can provide a great mix of expertise, and maybe some new ideas too.

In the first month, you will also want to create resources for your speakers, so that they have everything for their presentations and their promotions. Month one will have you busy with speaker management, creating content, and getting the tech side of things ready.

In month two, record the interviews with your speakers. For the ones who will be submitting their presentations to you, make sure their deadline for submission gives you lots of time before the event. Ideally you will have 30 days to edit their videos, and make closed-captions and transcripts.

You should also make sure that by the end of month two, your event website is built, collecting signups, and ready for the event. You should also have your All-Access Pass detailed sorted out, and it’s checkout and delivery process worked out. This is also a great time to pitch and sign your event sponsors.

In month three, you will be pre-writing your social media posts and email sequences. You will be testing your shopping cart, funnels, ads and making sure everything is ready for launch. Make sure you allow yourself time to test your live stream, and have a few practice runs. This way, when it comes to the real event you are prepared. And of course, month three will also be when you and the speakers are promoting the event and driving traffic to the sign up page. The last 30 days before launch will go by very fast.

Super. We are nearly done. Here are our final questions. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I am passionate about encouraging everyone to have their own online revenue streams. Simply counting on your employer to give you a paycheque is far too risky, in my opinion. You need to have control of your wealth, and having an online business (or a few!) is key. We saw remarkable job loss this year with the pandemic, but those who could pivot and take their services and products online can thrive.

Several years back I was laid off unexpectedly and found myself in a scary situation. I shifted to selling digital products online, and it changed my life! So that is why I teach online business development, affiliate marketing, and website investing. I aim to help people take control of their income and their futures. If there is someone reading this who feels stuck in their job, I want you to know that you have every opportunity online to turn your situation around.

What do you love most? You can create an online course or a virtual event and teach someone how to do what you know. No idea is too small. There is an audience for every niche, so let your creativity run wild!

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Oh, I would love to sit down with Jen Sincero for sure! She is hilarious! Her book ‘You Are A Badass At Making Money’ landed in my lap at the exact time I was making a personal transformation into business entrepreneurship. Her book propelled me into business with confidence like no other, and opened my eyes to so many things.

There is a part in her book where she talks about when she was deciding to become a coach, and she worried that her potential clients may discover old videos of when she fronted punk bands, as it may discredit her professionally now. I certainly dealt with this same feeling when I was stepping into my role as a professional. Although not cool enough to have been in a punk band, I have had a colorful past that didn’t align with what I assumed a professional business owner “should” look like. I was inspired by Jen’s story of how she confronted her fear of being “found out” and she came to the realization that every part of one’s journey matters and that we don’t need to hide our true selves just to appear a certain way in business. We will attract our ideal clients because they will love our real lives and quirks.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Thank you so much for having me. I’d love to stay in touch with your readers!


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