5 Things I’d Do Differently if Launching My Side Hustle Membership Group Again

Regret is just an opportunity to do it better next time.

About two years ago, I launched my side hustle, Marketing for Justice. It’s a membership group for law firm marketers, where we offer online digital marketing education via workshops, group coaching, a private community, and more. It has wildly succeeded my expectations, regularly generating $4K/month while requiring an average of 4 hours of work per week (sometimes a little more, sometimes a little less).

How I Generate $4K+ a Month in 4 Hours a Week

Don’t get the wrong idea, though.

That top line revenue number is misleading. Maybe not in the Bernie Madoff sense, but what I’m saying is that I’ve made plenty of mistakes — and if I had the opportunity to start over, there are a LOT of things I’d do differently. Here are 5 big ones:

1. Price the Membership Based on Value, Not Self-Doubt

Setting the price of your membership (or any other product or service, for that matter) shouldn’t be an emotional exercise. But for entrepreneurs like me — those who struggle with self-doubt and are well acquainted with imposter syndrome — that’s easier said than done.

The fact is, I significantly undervalued the worth of my membership program precisely because I undervalued my own. When I first launched Marketing for Justice, I charged $49 per month, or $249 when you paid annually. After a real come-to-Jesus moment, I closed my eyes, took a deep breath, and dove into the deep end, raising the price by 500% in one fell swoop.

I Raised the Cost of My Membership Group by 500%. Here’s What I Learned.

And guess what happened?

The business boomed. More members joined, no one blinked an eye at the new $249/mo. rate, and existing members participated more actively because they suddenly — subconsciously — recognized the true value of the membership.

The lesson here? Charge what your product or service — and by extension, you — is actually worth.

If you’re occasionally plagued by self-doubt, and your price doesn’t make you uncomfortable, you’re doing it wrong.

2. Not Pay Guest Experts

The structure of my business is centered around a 1x monthly “online workshop” (a fancier, way more enticing term for webinar), where a guest expert leads a training focused on a specific digital marketing channel or strategy, specific to law firm marketers. I’m very selective about who I invite to lead these workshops, only choosing those at the top of their game.

Because I wanted the best of the best, I just assumed I’d have to pay them — and in the beginning, I did. It wasn’t a lot — I was paying guest experts $200 per 1.5-hour workshop in the beginning — but it was still a pretty big chunk of change for a side hustle that wasn’t yet generating a lot of money.

I paid the guest experts for the value they offered my members, but didn’t consider the value I was offering them.

At the end of each workshop, I’d give the guest expert a list of contact information for every registrant — sometimes as many as 75 or 100 people. And because these workshops were specifically for in-house law firm marketers, this list was a gold mine for legal marketing agencies. I was basically handing over hundreds of highly-qualified leads for free, and then paying the expert 200 bucks on top of that.

It was, in a word, stupid.

(and very expensive for a startup side hustle on a shoestring budget)

So I stopped doing that, but I should have never started in the first place.

And guess what? I now have law firm marketing experts practically knocking down the door to get in front of my highly-qualified audience — even though I no longer pay them for their time.

3. Hire a Virtual Assistant

When I was first launching my side hustle, I was a comically overloaded one-man band. I didn’t have a lot of money, so I thought outsourcing anything was impossible. I’m also a perfectionist (a dangerous quality in any entrepreneur), so I just didn’t trust anyone to do the job, no matter how significant.

This was a huge mistake.

The thing is, virtual assistants (VAs) are both cheap and effective. You can pay an offshore VA a living wage (please, please make this a priority) and still only spend something like $15 per hour. And that $15 is worth its weight in gold when it comes to handing off manual tasks that would otherwise suck your time.

If I could do it again, I’d immediately hire a VA and assign them easy-to-do but time-consuming tasks so I could focus on the most important stuff.

Tasks I might assign to a VA include:

• Responding to common member questions via email and social media (I’d whip up some canned templates that would require only the slightest modifications)
• Queuing up social media posts in MeetEdgar and creating graphics in Canva
• Building landing pages for the monthly online workshops
• Editing the replay videos for the monthly online workshops, uploading them to the membership site and YouTube, and optimizing them for SEO
• Formatting guest experts’ slide decks in the Marketing for Justice style

Imagine the time I could have saved!

Instead of spending roughly 4 hours per week on my side hustle, I might have spent 2 or 3. Lesson learned.

Because every minute counts, especially when you’re also holding down a regular ol’ 9 — 5.

This Tool Cuts Time Spent on My $4K per Month Side Hustle in Half

Time is money, especially when you’re not making much to begin with.

4. Develop an Evergreen Lead Magnet

To grow my email list, I offered non-members access to one of our free online workshops. It was a win-win: they’d get top-tier marketing education and a chance to experience the perks of membership, and, over time, I’d get the opportunity to convert them into paying members with the most cost-effective marketing channel in existence — email.

The online workshop was a lead magnet, sure, but it wasn’t evergreen (meaning that I couldn’t market it continuously, because it only happened once per month).

Without a true evergreen lead magnet, I put myself at a major disadvantage. Instead of growing constantly, my email list grew sporadically and inconsistently.

If I were launching my side hustle again, I’d immediately offer an evergreen lead magnet to continually grow my email list. Maybe a recorded webinar, a downloadable video, a checklist or toolkit. Something potential members could get on-demand, anytime, in exchange for their email address.

There are few things more important than growing your email list. Set yourself up with an evergreen lead magnet so you can do that constantly.

5. Pay More for Lower Transaction Fees

I use Squarespace to run my membership group, and I gotta say, I’m pretty happy with it. It handles (almost) everything, from payments to member management, website design to video hosting, etc. But if you start with a lower-end subscription, you also pay higher transaction fees.

As in, way higher.

In the first few months, I paid hundreds of dollars in transaction fees to Squarespace (not to mention to Stripe, which also takes a cut). What I didn’t realize is that I could pay roughly $50 more per month to upgrade to a higher-end subscription, which, among other fun and useful things, came with dramatically lower transaction fees.

The thing is, when it comes to transaction fees, the difference between 7% and 5%, or 4% and 2%, may not seem like a lot, but it 100% is.

For me and my $4K/mo. side hustle, it means hundreds more dollars in my bank account each month.

So pay attention to the fine print when choosing a payment processor or a subscription level. I wish I had known I had more options when I was first getting started.

Spending an extra $50 on my subscription plan saved me hundreds of dollars in transaction fees per month.

The Short Version

Do I have regrets for how I launched my side hustle membership site? Sure. But as I mentioned earlier, I prefer to think of regrets as opportunities to do things better the next time. At the very least I may be able to help someone else avoid the trouble I ran into.

So, if you’re considering launching a side hustle (particularly a membership group), here’s what I’d advise:

• Charge what your product or service is worth — don’t give in to self-doubt (and if you’re grappling with that, remember that your pricing should make you uncomfortable)
• Don’t pay guest experts or instructors if you’re already giving them value (e.g., access to a highly-qualified group of warm leads)
• Don’t waste time on tedious, manual tasks (or get hung up on perfection) when you can hire a perfectly capable virtual assistant for $15 an hour
• Offer an evergreen lead magnet so you can continuously and consistently grow your email list (not to mention at a crazy high ROI)
• Read the fine print from your payment processor and consider upgrading your subscription to lower your transaction fees

Are you running a side hustle or membership site? What lessons have you learned? What have you done that you definitely wouldn’t do again? I’d love to learn from your experience. Connect with me on LinkedIn and follow my blog on Medium for more posts like this.