Deeper Business

Build your business - and your business-building intuition with foundational frameworks and practical application.

Aug 17 • 6 min read

The tale of two businesses


Here's the story of two businesses, each making over $100,000 per year.

There’s a lot to learn from comparing them, why they work, and what happens when we try to assemble a business that seemingly has the best of both worlds.

Business 1: Fractional C-Suite/Retainer Services

This business owner does fractional services, large projects, or retainer work (ongoing project management, copywriting, or podcast production).

The numbers:

  • Average pricing: $2,500/month ($18K-$60K annually per client)
  • Engagement length: 6 months to 3+ years
  • Delivery time: ~20 hours/week
  • New clients needed: 2-3 per year
  • Marketing time: 2-3 hours/week

How she finds clients: Personal relationships and participating in online or IRL communities/networks.

Most clients weren’t newsletter subscribers when they started working together. Some still aren’t, three years later.

Business 2: One-Time Purchases and Low-Priced Offerings

This business owner runs cohorts, small courses, and a low-priced monthly membership.

The numbers:

  • Average pricing: $2,500 cohorts, $250 courses/memberships
  • Engagement length: Mostly one-time purchases
  • Delivery time: ~7 hours/week, including delivery and course creation
  • New clients needed: 40-150 per year
  • Marketing time: 10-15 hours/week

How she finds clients: Broadcast marketing combined with heavy relationship building. Coffee chats, guest teaching, collaborations, some ads, and podcast guesting for exposure to new people. And a weekly newsletter, personal outreach, her own YouTube/podcast, monthly free classes, and sales calls for her existing audience.

She needs 600-1,200 new audience members every year just to keep the client flow going, and that’s at a conversion rate above industry averages.

What You Get and What You Give

Both businesses work. Both owners are happy. But the trade-offs are completely different.

High-Touch Recurring Work

What you get: If you don’t love marketing, this is for you. You get to focus on your craft. You’re not hustling for clients or constantly onboarding new people. You don’t need to understand 40+ different customer situations—just a handful at a time. And you don’t need broadcast marketing: a few portfolio pieces, some case studies, established referral partners, and slow-burn relationship building.

What you give: Repeatable work can feel booooooring at times. And those delivery hours are real — when I ran this model, I really was doing 20+ hours a week of client work. You might say you got into this so you didn’t need a job, but now you’ve got 2-3 of them, complete with different stakeholders, meetings, and politics.

One-Time and Low-Cost Purchases

What you get: So much creative freedom. Only 7 hours of delivery time per week! You get the time freedom you crave, with room for novelty like new courses and new workshops. Even when you’re running the same cohort content, it’s fresh participants each time.

What you give: That amount of audience growth requires a substantial amount of marketing in some format, even if the specific activities you run are different such as social or paid ads. (Ask me how I know this level of marketing takes ~10 hours a week). Maybe I could have done it more efficiently through other strategies, but I've grown my email list by about ~1,000 people since the beginning of 2024, and it took me 26 guest podcast appearances, 27 guest talks/collaborations, and a number of Kit recommendations to get there.

But these businesses are each congruent as a system.

I’ve lived and built both of these businesses.

Each business works because everything fits together.

It’s not about choosing the “best tactics”. It’s about operating your business as a system.

Business Model 1 (High-touch services) doesn't need a lot of clients and doesn't have a ton of time for marketing.

Business Model 2 (One-time purchases) does need a lot of new clients, which she has the freedom to do because her calendar is light on delivery.

When I was doing high-touch consulting work, I built my audience on the side—which meant I was actually running both models simultaneously for about 3 years. (It has been bananas on my calendar, but allowed me to focus on building a platform without having to sell to that audience for a very long time).

Maybe your business doesn’t operate at either of these poles: You have short but expensive projects, lower-priced long-term advisory engagements, or repeat purchases, so you need ~12 new clients per year. You’ll need more outreach and relational sales than just an hour a week, but not the high amount of broadcast-style marketing designed for audience growth.

The problems start when you break your system by mixing and matching tactics that belong to a different business model.

Three Common Ways We Break our Business Model

Break #1: Low-priced but high-touch delivery

You choose a business model like $1,000/month social media management. Now you still need a bunch of clients, but you’re also delivering 25+ hours a week. Where’s the time for client acquisition? This is the express lane to burnout.

Break #2: High-volume business with half-hearted marketing

You want the group or one-time purchase business model, but you try to do it with sporadic social posts, an AI-written newsletter, and occasional collaborations. You’ll struggle to get the exposure and trust you need for 40+ new clients annually.

Break #3: High-value services with scaled marketing

You choose retainer or large project work but spend your precious few marketing hours shouting in the algorithmic void with your content instead of building the referral relationships that will help you land those high-value clients.

Choosing Your System

I haven’t found a perfect business model.

They’re all hard somewhere. They’re all boring somewhere.

But the ones that work? Those business owners choose one system, that aligns with their strength, and increase their skill at executing it over time.

Ask yourself:

  • What’s my actual capacity for client delivery? (Energy, not just hours)
  • How many new clients do I really need each year?
  • What marketing can I realistically sustain long-term?
  • Which model’s difficulties energize me instead of draining me?

Your answers will tell you if you need to strengthen your system or find a different one.


Most people are trying to force tactics that don’t match their business model. Or they haven’t clearly defined their model in the first place.

This is exactly what we solve in Define Your Foundations.

We don’t just pick tactics. We build your entire business model from the ground up:

  • Map your optimal model based on who you want to serve and how you want to work
  • Design your revenue system to eliminate feast-or-famine
  • Create your marketing strategy around your strengths
  • Build the operational foundation that supports sustainable growth

No more copying what worked for someone else’s completely different business.

Just a clear, coherent business system designed specifically for you.

Next cohort starts September 18, with enrollment opening in late August to the waitlist. Limited to 15 participants so everyone gets the attention they need.

NEW EPISODES

Is it a lion or a Slack notification?

Entrepreneurship is hard. And it’s even harder when your nervous system is stuck in a mode that’s not serving you.

In this episode, we sit down with The Entrepreneurs’s Therapist Shulamit Ber Levtov to talk about the nervous system realities of entrepreneurship—especially for those who didn’t become entrepreneurs by opportunity but by necessity.

We talk about what it means to choose our nervous system activities, how to understand what’s in (and out of) our control, and the unique paradox of entrepreneurship: you get freedom… and also you’re the one holding the whole thing together.

UPCOMING EVENTS

Each month we'll discuss a chapter in my upcoming book, Leaving the Casino: Stop betting on tactics and start building a business that works.

Each dialogue is 12-1pm ET.

August 20: Your Business Model

September 17: What's the Impact You Want to Have?

October 22: The Responsibility You Carry

Community and Reads

I went on one of the biggest podcast in the world

I understand why, Jay Shetty’s podcast is HUGE, one of the biggest in the world. It seems incredibly exiting. And in many many ways it was! and it is! I so appreciate the enthusiasm from everyone, I felt so seen and supported.
When the podcast came out two weeks ago, James and I, my agent and my publishers waited with baited breath - how much of a pump would this give my book sales?

Everything is now opaque

Marketing used to be a game of visibility.
You researched the market, spotted the gaps, built the content, ran the ads. You showed up, people saw you, some of them clicked-and, crucially, you could see it happening. You had dashboards. Attribution models. Funnels. You could test, optimise, improve. It wasn’t perfect, but it was observable.
That era is over.
We’re entering a fundamentally different paradigm; where intelligent systems mediate how people discover, evaluate, and interact with brands. Whether it’s an LLM summarising answers, an AI assistant making recommendations, or a multi-modal agent facilitating purchases, the new digital experience isn’t about users browsing websites. It’s about systems making decisions.

Jessica Lackey

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Build your business - and your business-building intuition with foundational frameworks and practical application.


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