I want to get back to growing With Jack after a year of distraction by running lots of mini experiments and being more intentional with measuring results.

This month I focused on advertising on different mediums:

• paid newsletter
• podcasts
• social media ads

In the past advertising has had poor results. I'm not sure if it's personal or an insurance thing. I think it's an insurance thing because you're dependent on getting in front of people at the right moment in their cycle. That means either chucking loads of money at advertising so you reach tens of thousands, or it takes a bit of luck.

On my budget it's about making yourself known and playing the long game. This means that when it's the right time in their renewal cycle you're at the forefront of their mind. 

Here's what I tried this month.

The Dunker takeover - a paid newsletter

I'm an avid subscriber to The Dunker. My favourite takeover has been the cyber security expert one. Penny's takeover included lots of practical takeaways despite the subject being pretty dry… just like insurance! I took inspiration from this when writing mine.

The Dunker is part of Freelancer Mag so their readership is exactly who I want to target. They have 5,000 subscribers.

My takeover was scheduled to go live on the 6th at 3PM. Within minutes a quote had come through. It might have been a coincidence but it was just the start I was hoping for!

Beyond that Google Analytics only shows referring traffic as 5% on the day of the takeover, with the majority being direct or from organic search. However, I did only include two call-to-actions to With Jack's website in the newsletter. The rest was focused on just being helpful.

I can't see open rate or clickthrough stats, but I'm confident I got in front of a lot of the right people. Hopefully I am at the forefront of their mind when it comes to thinking about insurance. 

Doing It For The Kids - podcast sponsorship

I sponsored five episodes of the Doing It For The Kids podcast, with the first episode published on the 20th of March. 2 are scheduled for April and another 2 in May so this will be something I can report back on down the line.

Sponsorship includes:

• 30 second pre-roll
• logo on the podcast page and show notes
• social media mentions

What I like about DIFTK is that both hosts, Frankie and Steve, have arranged their insurance through With Jack. Because of this the advertisement feels authentic. See (hear?) for yourself.

As soon as the podcast was published we had a flurry of social media activity and new followers. Podcasts tend to perform well because it's more genuine hearing a third-party talk about a product instead of a direct pitch—especially if they're already a customer.

There are still 4 episodes to come. Plus, podcasts are evergreen content since people tune in weeks or months after an episode has went live. Hopefully this translates to sign-ups, but so far DIFTK looks to be a great asset for bolstering our social media followers and activity.

Social media ads

February's mini experiment was all about committing to social media. Algorithms do what they can to nudge you towards paid advertising, like limiting your organic reach. I was interested to see if paid Instagram ads would give us a boost with March's mini experiment.

This is definitely something I'll be doing more of. It was a promising start and it will only get better as I learn what freelancers respond to.

I tried a range of adverts:

1. [graphic] Tips for avoiding late paying clients
2. [photo] A policy feature I love
3. [video] Bonita and I
4. [story] A monthly recap

I ended up canning the ad for the policy feature I love. I was using my personal account one day when my own ad popped up. It turns out the description isn't shown and the photo for the ad made no sense with zero context.

The video, on the other hand, performed well. In the video I introduce Bonita, a husky / staffy mix, and myself as a hybrid—an insurance broker and ex-freelancer. It's not a traditional insurance advert but I'm trying different things.

Stats by the end of March

1. [graphic] Tips for avoiding late paying clients. 4,437 views, 49 website clicks
2. [photo] A policy feature I love. 249 views, 1o profile visits. This is the ad I quickly canned after seeing it on my own feed
3. [video] Bonita and I. 7,100 views, 559 website clicks, 191 profile visits, 3 follows.
4. [story] A monthly recap. 1,429 views. 36 profile visits, 2 follows.

Now that I have a bank of videos and social media content I can play around with ads more.

Perspective - podcast sponsorship

Another podcast! I've sponsored Perspective for some time so I shouldn't be including it in March's mini experiment, but they did have 3 episodes go live in March.

This is different to DIFTK in that Perspective had me record my own ad and it's played mid episode. They are wedding professionals so I tailored my messaging for wedding photographers or film makers, focusing on problems like your SD card failing mid-shoot.

It's hard to track referrals from podcasts, but Perspective has a small yet engaged audience. It's regularly mentioned when photographers or filmmakers are buying a policy.

Laying bricks

March has always been a good month for sign-ups, but I compared enquiries to last year and they're down 24%. It's a combination of only getting back into the marketing game 10 weeks ago, and the market being low on work opportunities for freelancers.

I can't expect instant results. These mini experiments are about showing up consistently and laying foundations.

But this month was a lot of fun and I feel like I'm falling in love with working on With Jack again after a period of stagnation. The social media ads will take some experimenting with to get right, but it's something I'll spend more time and money on.

I'll also continue to benefit from the podcast sponsorship since more episodes are lined up to come out over the next 2 months.

Total ad spend: £670

Looking back at January and February's mini experiment

From what I can see there have been another 3 backlinks from the proof of insurance badge. The referrals have had little uptake so this is my cue to remove that part of the script. I did deliberate on whether having two call-to-actions was too many. There's my answer.

Social media continues to get good engagement from my schedule of posting 3 times a week, which I started on the back of last month's mini experiment. Followers are up, views are up, interactions are up.

It doesn't seem like any of the mini experiments have translated to increased sign-ups… yet. I'm confident that by the end of the year the bricks I'm laying will add up.

A look at April's mini experiment

I've been on the fence about April. We're still dealing with the aftermath of my mum's death (it turns out there's a lot to sort) and many days I feel overwhelmed by everything.

It's been 3 months and my emotions are now catching up with what's actually happened. I'm going to keep this month light and create and optimise landing pages for specific sectors, like marketers, illustrators etc.