How we Organized Freelance Business Week Denver 2019

In October 2019 a small team of freelancers held a five-day event with 70+ speakers and 200+ attendees with the help of 25 sponsors across 16 venues. It cost us just shy of $5,000 and took over 1,500 hours. We made a profit of $2,700. This article will go into the nitty-gritty details of just how we pulled this off. This is part of a series—if you would like a higher-level recap of the event, check out this post, if you are interested in what we are planning next click here.

Table of contents:

Some Context

It’s fall 2018 and I’m co-hosting a session for Denver Startup Week. We are calling our session Better Together: How Freelancers Can Win. There are over 125 people packed into Woods Boss Brewery and we’ve got them moving all around the space, getting into groups and talking about the struggles and awesomeness of freelancing. It is clear that there is energy in this community. Something is present, waiting to emerge.

Building off this momentum, I begin to host monthly events. We begin to call ourselves Better Together. After a few months I write up a vision of what this group could bring into being. I believe the community of freelancers and independent workers in the Denver area could form into an association. Soon I’m connected to Emily Leach, founder of #FREECON in Austin, Texas (coming to Denver next September), and the Texas Freelancer Association. She introduces me to Freelance Business Week, a week-long series of events that she started in Austin and is taking national. She invites me to host it in Denver. Being naïve and maybe a little overambitious, I agree to consider it, if I can put together a team…

6 Months Out – April

Forming a team

In early 2019 I began pulling together the core team. Because Better Together was already hosting events, there were people in the community who had already built trust and taken on responsibility.

diffuse light pours in through large bay windows across a table full of snacks and computers. There are 4 people around the table with a 5th appearing in a computer screen on a stool.
One of our first core team meetings.

The core team:

Teams typically go through a process called nemawashi (Japanese for “laying the groundwork”) that consists of four phases: “forming,” “norming,” “storming,” and “performing.” A group forms together and builds norms. Then the “storming” phase is when the norms and expectations are tested, often leading to a new round of norming. You can guess what the performing step looks like.

I chose the team based mainly on intuition. I did my best to set expectations by being honest about my lack of experience and the fact that Freelance Business Week was a new venture. We would be charting unknown territory and there was no promise of success or profit. I also trusted that those who were interested could get the job done.

The team performed amazingly, I’d like to tell you it was more than magical luck, but I can’t point to anything beyond trusting my instincts to create that luck.

Creating expectations, agreements, and roles

As the team formed we spent a good deal of time setting expectations, which are outlined in our “working together” document (Template here). This document went over a few key things that any team should plan for before conflict or confusion arises:

  • Decision-making process — How will we make decisions? How will we handle contentions decisions?
  • Shared Resources — How will we share resources? Who will have access? (Assets, files, etc.)
  • Roles & Responsibilities — What roles will each person take on? How will we define/share responsibilities?
  • Communication​ ​Systems — What methods of communication do we want to employ? What agreements do we want to make about our communication, e.g., frequency, timeliness, etc.?
  • Conflict​ Transformation — How will we transform conflict from something that is blocking us to something that is helping us?

Answering these questions up front helped us start off on the same page and manage our expectations. We even took time to name certain expectations, mainly around profit.

“We will aim to turn a profit. The core team will ‘eat last’ but share in the leftover profit based on the ratio of time spent working on the project. We will track our time (and expenses) in FreshBooks.”

We also created agreements around interpersonal expectations:

“We will recognize that each of us has lives beyond this project, and we may not be aware of all that each other is dealing with at a particular time—and therefore, we will respect each other’s boundaries and treat each other with kindness and request more context when necessary. We will not assume that other members of the group are capable of mind-reading, and therefore will clearly and respectfully establish boundaries when needed.”

We decided to form our team around three key roles: Coordinations, Communications, and Logistics. At the onset we did our best to anticipate what those roles would be expected to do. I would not suggest using these roles—see Lessons Learned for our suggestions for roles.

Ideation

As we were setting our expectations and agreements, we were also dreaming of what this event could be. I think this is an important step in any design process. We allowed ourselves to dream big and explore the idea space.

colorful writing on paper
Our dream doodles.

Meeting rhythms

Part of our agreements were meeting rhythms. Having regular time to check in and work together helps keep a distributed team on the same page and keeps energy flowing. We decided to meet in person once per month and hold a video call each week, then meet in person once per week in the final month before the event

Master notes document

Keeping a single notes document is a great way to keep things organized. Between meetings, as questions and topics came up, anyone on the team could add them as agenda items to the top of the document for discussion at the next meeting. Having everything in a single place allowed us to go back and see what happened throughout the course of the project.

Indeed, this whole post was built by looking back through those notes.

Five Months Out – May

Once our forming and norming was complete, we set to work shaping the event. We began editing down our ideation and thinking about what we were going to do and who we were going to do it for.

Target personas

Jenn Uhen created 4 personas that we believed would be our target audience. The experienced freelancer, the part-time freelancer, the freelance-curious, and the solopreneur. We used these “people” to develop our themes and tracks.

Tracks, Themes, Tickets

Through conversation, looking at the existing Better Together community, and Jenn’s personas, we developed themes for each day of the week, tracks for different interests, and our tickets. Here’s the original theme and track positioning.

ThemeIntention +  InquiryTech + ToolsTaking Care of Business—
and Yourself
Level UpMake Things Happen
TrackMondayTuesdayWednesdayThursdayFriday
StartupBrand YourselfTechLegal + Self-careSell YourselfMake Connections (Networking)
EstablishedFinesse Your Brand and Your ProductsUpgrade TechNew policy awareness + keeping it freshRecreate Yourself / MentorshipMake Connections (Networking)
NomadWhat nomad are you? What would work?TechTaxes + self-careLiving the lifestyleFind Your Clients
CreativeComing to Terms with CapitalismTechSelling Stuff and Taxes + Creative ReconnectionBuild Your PortfolioMaker Faire

You can view the themes and tracks document with all its details here.

Quality of experience

We framed the development of the week around questions of “What will participants feel?” and “What will their embodied experience be like?” Here’s what we came up with:

  • Camaraderie: A sense that they are among people who both understand their struggles and can model paths to success. A sense that the “these are my people.”
  • Quality, valuable education: We want attendees to feel unequivocally grateful that they’ve attended. We want them to rave to their friends and strangers alike about how much they learned.
  • Eye-opening: We want people to consider business practices, life hacks, income streams, etc. that had never occurred to them before.
  • Fun: Not just at the Ignite talk [we ended up dropping this] or at social hours, we want there to be laughter and smiles at this event. Though we will be laying down serious knowledge, we will not take ourselves too seriously.
  • Getting to know Denver: Though many of the lessons will be about freelancing generally, this is also a great opportunity to show off and share all that Denver has to offer: its resources, its freelancers, its venues, restaurants, and best-kept secrets.
  • Buzz-worthy: We want everyone to be talking this conference up, before, during, and after it happens. Social media should be well aware that something big is happening.
  • Connections: We want people to meet new partners, clients, vendors, and friends. We want to make them “so glad” they decided to attend. 
  • Inspiration: We want attendees to get so many good ideas and hear so many inspiring personal stories that they can’t wait to “get back to work” and start implementing what they’ve learned.

Looking back at these from the after the event I feel like we did a really good job creating these qualities in our event.

Ticket Price

Because FBW is fairly new there wasn’t much to go off. The national team suggested a price of $25 but we felt that was way too inexpensive for what we were envisioning. We looked at comparable events and came to $195. We estimated that if attendees went to 10 sessions at $20, it would be $200.

Later in the process we created 2 and 10-session (for $30 and $125) tickets, which were very successful. I’ll cover what we would do differently under Lessons Learned below.

Marketing strategy

Once we had the shape and the price of the event, Madison created a marketing strategy. This became the guiding document for our social media and email marketing efforts. It provided a high-level map of what we were going to do and when we were going to do it.

Instagram

We focused our social media almost entirely on Instagram. As Madison pointed out, our target audience was mainly on Instagram, not Twitter or Facebook. We were targeting creative and marketing people and that’s where they hang out. This greatly simplified our efforts and allowed us to focus on a single channel.

Build out website

With the plan in place, we implemented our website. The FBW national team provided us with a WordPress site using the Divi page builder. It came pre-populated with pages and content that we tweaked. For our application forms, we used AirTable to collect data from visitors. More detail about the tools we used can be found in the tools section below.

Four Months Out – June

Invite speakers / hosts

Once the infrastructure was in place, we began putting the word out. Our speaker application was shared through the personal networks of the core team, across the Better Together community, and over social media.

Cross-promotion page

During this time we began forming strategic relations with other organizations and events. For instance, we reached out to the Outlier Podcast Festival and offered to send some freelancers there to hold open office hours to support the podcasting community. I think this is a great example of using the resources at hand to create win-win collaborations.

We created a cross-promotion page with links to our logo, colors, and other design assets along with copy templates for email newsletters. Our intention here was to give people the resources to make it very easy to share our event.

Business card for peer-to-peer promotion

image of a front and back business card showing the Freelance Business Week Denver logo, dates, and hashtag along with the text '5 days of talks, events, and activities across Denver'

We had business cards printed with information about the event that we were able to leave at gathering spots and hand out at events. These were super helpful for networking purposes. Download source file here.

Develop sponsorship relations

In an effort to find sponsors we created a list of potential leads and started reaching out. Because this was our first year we had no metrics to show off and this made the effort challenging. Better Together had a few relations, mainly with Name.com, who immediately cut us a $1,000 check upon request.

In retrospect I feel that I could have done a better job showing that Better Together had been bringing people together for over 6 months. The lesson here is that hosting smaller events might lead to stronger sponsorship relationships.

We did find great success with in-kind sponsorships. Coworking spaces were interested in hosting freelancers (their potential clients) and generally it’s easier to get products and services from businesses than it is to get money.

Three Months Out – July

By early July we had 16 speaker applications and 7 tickets sold. At this point our early-bird special was live, offering 75% off the ticket price (we didn’t, however, have anything up about content, so there was very little for people to go off).

We were spending most of our time developing relationships with venues, reaching out for speakers, and building buzz. Internally we were working out details like the digital grab bag and copy for the website. Madison put together a strategic marketing plan that outlined email and social media in more detail.

Two Months Out – August

By the close of our application process, we had 60+ speaker applications and 13 tickets sold.

Soona promotional video

One really awesome sponsorship relationship was with Soona, an on-demand photo and video studio. We negotiated free (in-kind) studio use for promotion and inclusion in our programming. We worked with them to create some awesome videos to promote the event.

Volunteer application

By this time we had collected a few volunteer applications through our website and started reaching out for volunteers through our network. It became clear we would need a volunteer coordinator, something we found but could have used earlier in the process to take some of the workload off of our core team.

Posters, flyer the city!

We printed bright-green posters and started posting them all around the freelancer haunts, cafes, coworking spaces, etc. Source files available here.

Discount Codes

We used different discount codes to track our outreach methods. We kept a spreadsheet with the codes and what they were used for. Later we were able to track which codes were used to buy tickets to judge how well our different methods for outreach worked.

business cards10% off1
video ad10% off1
website10% off5
Upsale (offer to 3/10 session ticket holders)20% off2
Unicorn sale (instagram)40% off with 30 uses2

As you can see, not many folks used the codes associated with different mediums. 

Speaker selection and agreements

We used AirTables to track our speakers. I put together a three-person committee tasked with making final selections. Once again these folks were pulled from the existing Better Together community. Our process was fairly simple:

  1. Divide the speakers between the three committee members.
  2. Have each member mark their speakers as yes, no, maybe.
  3. Review the speakers marked maybe in a committee meeting and make final decision.

Once the speakers were selected we were able to send out speaker agreement forms using HelloSign.

Collaboration with other events

We collaborated or participated in a few events leading up to FBWDEN: Matchbox, Outlier Podcast Festival, and Denver Startup Week. This was a great way to promote the wider community and get exposure to people who go to events like this.

One Month Out – September

With just a month remaining, the work on relationship-building and technical systems slowed, while the logistics became a central focus.

Trim the fat

As the date approached, we realized that some of our big ideas weren’t going to make it into the final product. It was time to simplify. We couldn’t find someone to “own” the Ignite talks, so we turned that into the Monday-night social gathering. Our GLAM Session, a space where freelance stylists would “glam up” our guests and then photographers would take their headshots before the Thursday party, was going to cost too much and we hadn’t been able to organize the stylists.

There were plenty of things that we’d thought we could do, but ultimately couldn’t. We made the mistake of promoting some of these events, even going so far as to offer free tickets to the ignite talks, but as we quietly removed them, no one seemed to notice.

These are now ideas for future years. In retrospect, we should have “designed by subtraction” a bit earlier in the process.

Logistics logistics logistics

With our speakers selected, it was time to puzzle together the schedule and start arranging the venues. At one of our in-person meetings, we put all the sessions on sticky cards and drew a calendar on the whiteboard, then went to work. In the course of an hour, we had built the first draft. From there we set the times and dates in AirTable and handed it off to Jenn to build the run of show.

photo of a white board with columns and sticky notes drafting out the run of show
The first draft run of show.

Run of Show

Jenn Uhen took on the lion’s share of fitting everything into place. Matching up the sessions with available venues then building the master run of show (ROS). This document detailed the whole timeline of our event. Each sheet (or tab) is a day. The columns are for each venue while the rows are 15-minute increments.

Jenn also created a run of show document for each venue with contact details and basic information about the schedule. These were sent to each venue so they knew exactly what to expect.

Paid ads

We spent $362.75 on Facebook and Instagram ads. Based on limited analytics research it appears that they didn’t result in any additional ticket sales (as far as we could tell) but they did get the word out.

The event

Our event ran very smoothly, with just one last-minute speaker cancellation. Volunteers were coordinated, people knew where to go (though parking was hard), and there were lots of snacks. You can read more about the event itself on our other blog post. Overall, our planning paid off.

Lessons learned

Sharon Banks, who volunteered at the event, approached us and offered to do an after action report. What follows mainly comes from her report, which is based on interviews with the core team, volunteers, and other stakeholders, as well as feedback from our community.

Successes

  • Great teamwork with a high degree of trust.
  • Meeting rhythms helped keep us in good communication
  • Three- and ten-session tickets were successful, though implemented late
  • Many freelancers and team members indicated that they felt part of an engaged community with high-quality participants.
  • Instagram ads broadened reach, though not necessarily ticket sales

Deltas – places for improvement

  • Shared coordinator role led to confusion; better to have a single person in charge.
    • More clarity about the scope of work for core team.
  • More after-hours events for freelancers still working 9–5 jobs.
  • Marketplace could have been before the main event and used to sell tickets.
  • Timing competing with Denver Startup Week.
  • People weren’t that interested in self-care.
  • Sessions weren’t very interactive, mainly lecture style. More support could be given to speakers to help increase interactivity.
  • Speakers did not know about sponsors, parking, lunch, etc. and so could not share with the participants. Could have shared event slides or information sheets with speakers.
  • The only way to be informed of speaker emergencies was through email, which was hard with last-minute cancellations.
  • Some speakers were added late in the game which made marketing and scheduling difficult.
  • Parking and getting around was a challenge.(We heard this one a lot.)
  • Lack of metrics made getting sponsors challenging. Few cash sponsors.
  • Low profit for core team (all told, we earned about $3/hour).
  • Printed too many flyers, business cards, posters, and bags. (My car currently has 200 tote bags in it!)

Recommendations

  • Redefine the structure of the core team to better meet the diverse needs of the conference. Possible structures could include:
    • Coordinators for each day or location.
    • One coordinator for full program and assistants only.
    • Executive producers and assistant vice producers for each location (yet a clear lead).
  • Market to speakers earlier so you can vet them effectively and make fewer last-minute changes.
  • Create communication strategies for speakers (i.e., share phone number for emergencies) and consider using one technology to address the need to regularly communicate with speakers.
  • Provide speakers with a slide or directions that they should share with participants on sponsors, events, meals, and information about space.
  • Consider simplifying the program and locations so as to make it easier to manage, easier for participants to attend, and to help reap a higher profit. Some changes could include:
    • Only using one space per day (or maybe on certain days like Tech Tuesday).
    • Reducing number of programs (maybe only focusing most programs on Tuesday through Thursday, as suggested by the national team).
    • Add a few key tracks and then add more if enrolled numbers exceed defined totals.
    • Provide fewer sessions with time between sessions. 
  • To reduce parking issues in Denver (a huge pain point for some), consider applying one or all of the following options:
    • Use spaces outside central Denver.
    • Map out parking details for each option.
    • Reduce locations and simultaneous sessions so people do not need to move cars frequently.
    • Find locations (possibly not coworking) that offer space.
    • Collaborate with local garages for discounts.

Tools & Practices

  • Meeting Rhythm – One in-person per month, one virtual meeting per week. One in-person per week in the final month. Zoom or Google Hangouts for video calls.
  • Master Notes Doc – Keep a single shared document with each new meeting agenda/notes at the top.
  • Google Drive – shared documents / collaboration
  • Asana – task management
  • AirTable – data management
  • Slack – real-time communication
  • Instagram – social media marketing
    • Later – Instagram scheduling
    • Canva – graphic design and templates
  • Sched – event management
  • Eventbrite – ticket sales
  • Hellosign – speaker agreements
  • Email – groups through G Suite
  • ActiveCampaign – email blasts (Mailchimp would also be good)

Templates and example documents

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