🟢 Lessons from earning $41K/month online

And what I dream of next

(4 min read)

In my previous post (about 5 magical shifts in solopreneurship), I wrote about increasing from $500/client to $5,000/client in our group coaching business.

With our new premium pricing, my partner Katie and I were able to attract much more serious clients, and our revenue increased, at its peak reaching $41K within 30 days.

(The pricing option that clients chose most frequently was a single upfront payment of $5,000, but that wasn’t the only option available.)

I also mentioned that my new goal is to experience a 5th “shift” in my entrepreneurial journey.

The lifestyle that we’d created with that business wasn’t what we hoped.

Let’s explore:

🟢 How we reached $41K

🟢 What it felt like (good and bad)

🟢 What we could have tried instead

🟢 What I think the 5th shift will be

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How we reached $41K

The business model was simple.¹

1. Run Facebook ads offering counter-intuitive advice about dating.²

2. From the ad, link to a landing page offering a free masterclass teaching a 5-step process for dating.³

3. In the masterclass video, offer useful tips, inspiration, and encouragement.
   
   Demonstrate the value of expertise and coaching.
   
   Invite women to apply for a complimentary 1:1 strategy session phone call.

4. Women who enjoy the video would visit our calendar and schedule a call.
   
   Once they find a time slot that works for them, they complete a short form.
   
   [Side note: If their answers revealed that they were not a great fit for our program, we’d send them other resources that were a better fit and canceled the call.]

5. On the 1:1 phone call, ask what the prospective client had tried, how important their relationship dreams were to them, and let them know what our program would help with.
   
   If they want to join and pay in full up front, offer a discounted price of $5,000.
   
   They read their credit card number, and we type it into Stripe, and welcome them into the program.
   
   Give them access to our online course and tools, and invite them to our group coaching calls.

Few businesses are simpler than that!

We had only 1 source of clients (Facebook ads) and only 1 product/service (our online course + group coaching program) and only 1 way that new clients could pay (reading their credit card number on a 1:1 call).

What it felt like (good and bad)

We felt so excited to have figured out this flow. 🤩

Our imaginations started going wild with how large our program could become. 💭

The fulfillment of our program was not a bottleneck. 🎉

Since the coaching was group instead of 1:1, and clients benefited from others’ participation on the calls, we felt like we’d be comfortable inviting more clients at a time.

However, you might have spotted 3 problems:

1. Running Facebook ads was so painful. 😣

   1. Facebook is one of the worst companies in the world. Dealing with FB at all feels gross.

   2. Plus, They banned our account many times, which stopped our business completely each time. We always felt like our sole source of clients was precarious.

   3. We didn’t enjoy the chore of running ads, especially since the ones that performed best for us were on the weekends, when we’d prefer not to be thinking about work.

2. 🛑☠️ It was exhausting to handle all sales 1:1.

   
   This was the main bottleneck on our business and the worst emotional drain.
   
   We’re introverts who prefer quieter days (rather than talking with new people constantly).
   
   This is important. You need to know yourself and what kind of days you’re designing.
   
   We didn’t enjoy having such a large portion of our schedule consumed by these calls.
   

3. [See below about the 5th shift]

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This post is public, so feel free to share it. 🙂

🙌 Do you want to get featured in a future issue? Let me know.

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What we could have tried instead

We’d created a difficult life for ourselves.

We thought we saw a way out of it:

1. Outsource the management of our ads.

2. Outsource our sales calls.

3. Ideally, outsource the management of all of those people too.
   
   I.e. Partner with someone who enjoys and is excellent at managing people.
   

We started down this path.

We created an open role for ads manager and one for enrollment coach (for the sales calls).

We conducted interviews for each.

We also hired a copywriter to see if we could succeed in selling a fully-scalable self-study online course (without the coaching added in).

Then the pandemic started.

Dating = strangers meeting each other.

Terrible idea in a pandemic!

We were already exhausted before the pandemic started (and feeling like we’d need to redesign our business or close it down).

Now we felt like trying to figure out how to keep the business alive (without needing to encourage strangers to meet each other!) was going to be too difficult.

So we closed the business and got jobs.

What I think the 5th shift will be

How would we have redesigned the business?

And what kind of business do I want in the future?

I already hinted at it.

Our business was mostly a service-based instead of asset-based business.

Since our program involved live group coaching calls + async advice online…

We had created a job for ourselves.

If instead our business had consisted just of digital products (e.g. an online course), it would be infinitely scalable.⁴

We’d be able to reduce our work-week down closer to ~0 (just marketing and minor maintenance).

The way to build wealth is to create (or acquire) income-producing assets.

The best business owners don’t work in their business. That would be a job.

Instead, they create assets.

(A business itself could be an asset if the owner hires a CEO who hires and manages other people. I don’t have experience with that.)

I don’t want jobs in the future, even ones I could create for myself.

I want fulfillment and financial freedom.

So, I’ll figure out digital products that I can enjoy creating.

And I’ll explore scalable, enjoyable ways of promoting them (e.g. this newsletter).

It will require patience.

But I wouldn’t be surprised if I experience what we saw in our dating clients’ lives:

If you raise your standards and hold true to your vision and deploy patience, paradoxically you get faster results.

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🖥️ Upcoming workshop: personalized guidance about how to earn $5K per client

In my previous post, I mentioned that I could offer a workshop about earning $5K per client in group coaching.

It’s happening. 🎉

There are 3 spots remaining.

It will be a live workshop and Q&A where I’ll teach exactly what I wish I knew (how to skip years of struggle).

I mentioned that I’d love to experience a “5th shift” where I learn how to sell digital products.

Group coaching is my 2nd favorite business plan, and I’m glad we learned everything we did about it so that I can fall back on that if I want.

Reply if you want more details.

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🕙 What we learned in recent posts:

🟢 How we earned $5K per client without offering 1:1 services

🟢 27 days in, I fold?!

🟢 The gross thought that helps me every day

🟢 “Impossible” transformations I needed to experience for myself

🟢 [See all posts]

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👀 Caught my eye this week:

Tim Urban of Wait But Why is one of my favorite writers.

Watch just a minute (from this timestamp) of his review of the Apple Vision Pro.

I’m not an Apple fan, but this does look pretty darn impressive, with some caveats.⁵

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🔜 Coming up (Saturday’s post):

The fastest way to upgrade your beliefs about what you can accomplish

💬 Question for you:

I’ll probably rename from “Work Less, Profit More”. I’m still trying to figure out how to label what I like thinking about and writing about.

Suggestions?

Reply or leave a comment!

I’ll be so excited to write back to you.

And if you've got a moment, I'd love to hear what you thought of this email.

Send me a quick message — I reply to every email ❤️

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📣 Special thanks to:

Janet Ridsdale

of

Now What? With JR

for your restack and support!

1. But the winding path to “figure out” that model was painful and took years.

Lots of failed experiments, lots of expensive coaches.

2. Recommend being pickier and raising their standards.

Most middle-aged women fear that “there aren’t enough single men available” in their town.

Hearing success stories of women who held out for a phenomenal match was intriguing enough that they’d want to learn more.

3. Coaches told us “the fortune is in the follow-up”.

So we collected people’s name and email address before showing the video.

In our experience, probably 100% of our clients bought immediately or never.

I doubt that any of our follow-up attempts helped.

So maybe collecting email addresses at this stage wasn’t necessary.

4. Not literally, but for the purposes of a 2-person business, it would be more than enough.

5. In his article, he says:

“The best way I can describe how I feel about the Vision Pro is a strange combination of utterly thunderstruck and mildly underwhelmed.

The magical interface, the giant screens, the immersive experiences—they’re just unfathomably cool and awe-inspiring. It feels like a sneak peek at the 2030s.

But after a couple of days, I found myself thinking, “Is that…it?”

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