Freelance Fest: The Good, The Bad, And The Ugly Of Our Biggest Ever Event

by David Broderick

A few weeks ago we hosted the biggest event in Top of the Funnel’s four-year history:

Freelance Fest

We were joined by some amazing speakers (shout out to Lashay, Lizzie, Liam, Rachel, and Brooklin!) 

And we’re really happy with how it went.

Buuutttt some parts could have definitely gone better. 

Here’s a breakdown of the good, the bad, and the ugly of our first Freelance Fest.

But first…

Why Freelance Fest?

TOFU has changed a lot over the past few months. 

Tyler’s weekly round-ups of the best gigs shared in TOFU have driven hundreds of sign-ups to the community since we started doing them in April.

And most of those new members are freelancers, given where they’re found us from. 

So, TOFU has become a bit of a hub for freelance content folks.

Lizzie Davey also joined us for an awesome workshop on her warm pitching strategy in March.

And that quickly became one of our most popular webinars.

So, we knew TOFU members would want to hear more on those kinds of topics.

Plus, I’m a freelance content marketer.

And a virtual conference full of short and sweet workshops from awesome folks like Lizzie is the kind of thing I’d want to attend.

So, that’s what we decided to do.

And here’s how it went down…

The good

On the whole, we’re buzzing with how Freelance Fest went.

Here’s why…

It was the talk of Freelance Town

Real talk:

Our guest speakers pretty much never post on social about the workshops and Q&As they join us for.

We ask them to.

In the past we’ve even written LinkedIn posts for them to use.

But as a rule, they never post about the webinars they join us for.

Freelance Fest was different.

All five of our guest speakers (and Tyler, obvs) posted about the day multiple times on LinkedIn to their collective 80,000 or so followers.

Stuff like…

I think our speakers were more than happy to share stuff about Freelance Fest because they were saying “hey check out this cool event I’m part of”.

Whereas posting about a workshop you’re hosting might feel a bit more “look at me! Aren’t I great! Come listen to me talk for an hour”.

Because Freelance Fest was more of an “event” than our usual stuff, I also felt like I could be a bit cheeky and ask some of the folks I know with newsletters to give Freelance Fest a shoutout.

That got us featured in Aleyda’s SEOFOMO, Nick LeRoy’s #SEOForLunch, Chris Bibey’s Freelance Framework, and Kat Boogaard’s freelance newsletter (thanks so much for the shoutout folks 🙏)

And that all meant…

1,373 people signed up!

Tyler and I agreed a few weeks out from Freelance Fest that we’d be happy if 400-500 folks signed up for the event.

1,373 people ended up registering 🚀

Over 1,000 people joined the livestream during the day.

Plus, the recordings of the day’s workshops have racked up nearly 1,500 views on our YouTube channel in just a couple of weeks:

People loved it!

Check out these lovely comments folks dropped at the end of the live stream:

And this lovely LinkedIn post from Rachel:

And these lovely Slack comments from Belinda and Ayorinde:

Woohoo 🙌

The day ran cha cha real smooth

We asked our speakers to record their workshops in advance rather than deliver them live.

That way we didn’t have to stress about people running over their time slot, computer nonsense, or anything like that.

And we combined those prerecorded workshops with a couple of live Q&As and virtual networking sessions.

And man, the day ran as smooth as butter.

Strong recommend on that format for anyone thinking about running a virtual event.

We’ve written the Freelance Fest playbook

There’s SO much comms involved in an event like this.

Emails arranging logistics with the speakers.

Social posts.

Slack announcements.

It was a lot of work.

And I’m really lazy.

So, I added everything I wrote to a big Google Doc along the way:

And now I’ve got 7,000 words worth of content I can repurpose rather than write from scratch next time round.

That’s legit gonna save us dozens of hours.

The bad

Woohoo so Freelance Fest was a total success.

End of article.

Thanks for reading byeeee 👋

Wellll not exactly. 

Here’s what didn’t go so well…

Virtual networking no shows

The virtual networking calls we run in TOFU every month always go down a storm.

So, we decided to run two virtual networking sessions as part of Freelance Fest.

Because it’s not much of a conference without networking, right?

It was awesome to see this LinkedIn post from Nikita, who was specifically excited about the networking on the day:

And she wasn’t alone.

129 people signed up for the Freelance Fest virtual networking sessions.

Woohoo, right? 

RIGHT!?

Well, not exactly. 

Because less than half of those people actually showed up to the calls they’d signed up for 🫠

Which left a bunch of folks who did turn up ghosted 🫠🫠🫠

One poor TOFU member was the only person who showed up to BOTH the networking calls they signed up for:

So that sucked 🙃

The silver lining from all this:

We think we’ve come up with a fix to stop people from being ghosted on TOFU Connect calls from now on.

Up until now, we’ve organised everyone who signs up to our monthly networking calls into separate calls of three or four folks in advance.

And we always get a bunch of no shows.

Then we have to frantically run around finding new calls to add the folks who’ve been ghosted into.

So, we’re going to test inviting everyone to one big Google Meet call. Then we’re going to sort everyone into groups of 3-4 in breakout rooms in real-time.

The start of each call is gonna be messy.

But then at least folks can sign up to our TOFU Connect calls knowing they’re 100% not going to get ghosted.

And the World’s Ugliest Email award goes to…

Freelance Fest was the first event we’d ever run through Kajabi (we’ve recently switched from Luma).

So, we had a few teething problems setting up the event page.

The biggest – in more ways than one…

The GIANT TOFU logo we couldn’t stop from showing up at the top of every Freelance Fest email 🫠

The emails had to go out, so out they went 🙃

Cool takeaway from this if your crippling perfectionism stops you from ever shipping anything:

These ugly-ass emails still helped drive over 1,000 views on the day and 129 virtual networking sign-ups.

So I can finally confirm that those really annoying people are right.

Perfect is the enemy of good

The ugly

Oh wow you thought those poor people getting ghosted was bad?

I wish that was the worst of it.

Because…

Freelance Fest didn’t make any money 

We pulled together a list of 159 companies whose ideal customers are either freelancers or content marketers. 

Then I cold emailed every one of those companies to ask if they’d like to sponsor Freelance Fest.

 And I followed up with each of them between one and four times.

All that effort got us:

Five replies along the lines of “sounds cool but we don’t have budget right now”.

And zero sponsors.

So back to the drawing board on that side of things for the next Freelance Fest. 

Speaking of which…

Freelance Fest 2: Electric Boogaloo

We’re going be hosting the next Freelance Fest in January 2025 🙌

We’ll be doubling down on what worked. 

We’ll kick everything that didn’t to the curb. 

And you won’t get ghosted if you join the virtual networking calls 🥳

If you haven’t already, join us in Top of the Funnel to be the first to hear about the next Freelance Fest as soon as we have info to share!