How I'd help Jay Clouse prepare his business for paternity leave in 6 months

...if I was part of his team

This is the first edition of a new experiment I’m running on this publication where I write public letters to entrepreneurs I admire. My goal with this experiment is to find the business I can help integrate and grow as if it was my own, since I’ve realized that’s what I want to do with this next chapter of my life. And who better to start with than Jay Clouse, THE creator experiment guy whose business Creator Science I’ve been following for a long time and deeply respect, regularly discuss at lengths with fellow creators I met through his community The Lab, and whom I occasionally send unsolicited feedback to.

Hello Jay,

I saw your LinkedIn video announcing baby #2 and your goal of taking 2 months of paternity leave in November and December. Given everything I know about your business, this had me struck by shocked Pikachu face. Changes are coming to the Creator Science business!

So, I went down a rabbit hole of watching your latest business retro for members of the Lab and listening to 4 of your most recent podcast episodes to try and understand your thinking and what changes you’re planning to make.

I’m so glad I did because it allowed me to see just how differently you’re willing to approach your business. I’m really excited for you and I had some thoughts about how I’d help you prepare if I was part of your team, so I thought I’d share them here.

Your stated goals

“We’re doubling the family so we gotta double the business.”

You said this half-jokingly but you also said it feels like a scary goal because you might fail.

At the same time you want to have more time to spend with your family (including 2 months of paternity leave) and more time for reading and writing (your book!).

Your big question this year:

“Can I reduce the time spent in the business without reducing the value the business creates for the audience and the value we capture in the business?”

Why this is a big deal

I’ve been following your business for almost two years now and this isn’t the first time you’ve mentioned wanting to get yourself out of the operator role of your business.

11 months ago, you wrote about being the bottleneck of your business and wanting to get yourself out of operations. Last summer/fall you explored the option of hiring a fractional COO to run your business but were deterred by the costs. In your 2025 Year in Review you wrote “I am (still) the bottleneck (…) Even if I’m not going to hire full-time (the current plan), I could still be doing a much better job of outsourcing.”

But this time does feel different.

• You have the experience of having your first child and want to do things differently this time around

• You plan to take 2 full months off

• You’re seriously considering hiring

• You said “the team is going to be running the business” 😱 (I never thought I would hear you say this)

• You just got back from an author’s retreat which seems to have really impacted you. You saw how bestselling authors you look up to run their businesses, what’s possible. And you heard how they see you which inspired you to start seeing yourself in a new light, too. You said you want to try to match the belief and confidence others have in you.

How you plan to get there

Pieced together from your latest retro and podcast episodes:

• Using AI in the ideation phase of content creation, building internal AI tools, making open claw assistant more useful as community manager (sensing intelligence about what needs attention, what’s worth including in the Weekly digest)

• Relax the content creation schedule and focus more on value (which you’ve started doing with the podcast)

• Improve onboarding (of the newsletter and the Lab)

• Give more operational tasks to your assistant Izzy, let her take more ownership with sponsorship deals (she’s been asking you to let her “take on everything” and you’ve been reluctant so far)

• Get up earlier and dedicate some of that time to writing your book and some of that time to working on the business (instead of in it)

• Stop wearing both hats as visionary and integrator. You mentioned being inspired by the EOS framework and the Culture Index. You realize that you’re the bottleneck of the business and need to let go of operations, so you can focus on higher-leverage, visionary work like building strategic partnerships.

• Build out your team and potentially hire someone full-time to run the operations (with a big MAYBE!). You believe that hiring someone full-time means getting their full attention while hiring part-time means getting a quarter of their attention. So, you lean towards hiring someone full-time but worry about making such a big investment in the business. However, you also believe your first hire should directly lead to more revenue (a successful business owner gave you that advice), so you’re hesitant to hire for operations first.

• Make fewer moves, bolder strokes (which you feel is somewhat at odds with hiring and growing because that should mean “doing more”)

Why this isn’t enough

This is a much different set of intentions than I’ve heard from you before which I find really exciting. But I believe there’s a gap between the goals you set and the plan you’re describing, and it’s getting bigger with time.

Listening to your thoughts of the past couple of weeks, I get the impression that the goals you set inspired by the author’s retreat are still going strong. But your commitment to what you’re willing to do to get there has been fading a bit.

From “I want to reengineer the business”, “I need to stop wearing both hats as visionary and integrator” and “the team is going to be running the business” to “I suppose I could delegate more tasks to my assistant Izzy and have her own sponsorship deals” and “I can get up 1.5 hours earlier to work on the business.”

You have this strong, inspiring, ambitious goal (it’s even SMART for goodness’s sake):

In 6 months, you want to double the business while spending less time in it and then taking two months of paternity leave.

It deserves an equally strong, inspiring, ambitious plan.

This made me think of something James Clear wrote in his newsletter:

“The rules:

(1) know precisely what you want,

(2) determine the cost of what it will take to get it,

(3) don’t bargain over the price.”

–James Clear

6 things worth examining

1. You’re the most customer-facing creator I’ve ever bought from

I’ve been a customer of several creator businesses at different price points, most of them higher-ticket than yours.

The most striking difference is this: you’re both the face of the business and the only person I’ve ever interacted with as a customer. And I’m a Basic tier member, your least expensive product.

In every other program I’ve bought (like the Part-time YouTuber Academy by Ali Abdaal and Write of Passage by David Perell), I was mainly or entirely looked after by the team, not the founder. And I was thrilled to work with their teams, because especially Ali positions his team as mini-celebrities inside his business.

I get why you do this differently. You believe that people come to the Lab expecting to join a community crafted by you, and you don’t want them to feel handed off. The Lab is the core of your business and community-building is your forte (the thing you’re known for!) so it feels right for you to be running this.

But this isn’t scalable, and there’s a less obvious cost: your business doesn’t look aspirational from the inside.

Creators join the Lab to learn how to build and grow a business. But the business they’re learning from seems exhausting and complex to run. There’s a gap between what you teach (focus on one platform and one signature offer, etc.) and how your business operates. You have, of course, written about this: “You give better advice than you take.”

The perspective I think you’re missing is that your role as a rolemodel might be more important than your role as community manager and coach.

If you do decide to further professionalize your business and step out of this customer-facing role, you unlock a new level of business for your community members, too.

2. You tend to hire specialists

Your hires so far have mostly been specialists: an audio engineer to raise podcast sound quality, a YouTube producer, your assistant Izzy initially brought in for short-form content repurposing, Mal as head of Instagram.

Having a team of specialists with no other person to manage them keeps you in the integrator role.

When you did look for operational help, you went looking for an expert too: a fractional COO who could “hit the ground running.” It makes sense that you didn’t want to spend the time training someone and an expert would need less of it. But then the cost deterred you from going through with it and you ended up making no change to your team structure.

This is different from what I’ve seen other creators do, like Ali Abdaal, Daniel Botero who turned his VA into his COO, and Michael Bungay Stanier who hired his future CEO from behind the bar of a pizza restaurant. They all hired someone junior, enthusiastic, and values-aligned, and let them grow into the role.

They describe the process something like this:

1. You hire this junior enthusiastic person

2. You teach them a process you’re currently doing

3. They document and standardize it

4. They hire and train someone else to do it

5. Repeat until you’ve taught them all processes

6. Profit (lol)

3. Your Basic tier could be a ramp (instead of “Standard-lite”)

The Basic tier of the Lab has a retention problem. You’ve been making changes to try and fix it: opening up direct messaging, running a month of revenue experiments, sending a weekly digest.

I don’t think these changes address the root cause.

The Basic tier is currently designed as Standard-lite, a lighter version of your full membership at a lower price point. And I get that you don’t want to make the higher tiers look unattractive by giving too much away at the bottom. But this overlooks that the Basic and Standard tier have different target customers with different needs.

Standard and VIP members are established creators who are making at least $10k/month or have at least 10k subscribers on a single platform. They roughly know what they’re doing and they come to the Lab to hang out with and learn from fellow professional creators. Access to you helps them grow because they know what to ask.

Basic members are still figuring out the basics (lol). They don’t always know what they don’t know. They might think their next step is optimizing their funnel when they haven’t yet figured out a compelling offer. Unguided access to you is less useful at this stage because they’re not yet in a position to use that access well.

So the current Basic tier gives the least structured support to the members who need the most direction.

What I heard from Basic members who didn’t renew when I talked to them is that they liked the courses, they met interesting people, but they couldn’t see how staying another year would get them any closer to where they wanted to be. One person said: “If I could see a path to making $10k/month by staying in the Lab, I would stay.”

The people I talked to were mostly blaming themselves for not making better use of the Lab, so they’re unlikely to tell you what changes to make. But as you keep reiterating, memberships should be designed to make it as easy as possible for people to get value, rather than putting the burden on the members.

So, the reframe I’d suggest is rather than asking “how do we give Basic members a good community experience?” start asking “how do we get Basic members to $10k/month or 10k followers as efficiently as possible?”

Some possible starting points:

• A structured onboarding sequence that diagnoses where someone is and points them to the most relevant material

• Collecting the success stories of Standard/VIP members and turning them into potential paths for Basic members

And improving member retention is one way a new full-time hire could have a direct impact on revenue.

4. Should your first hire directly generate revenue?

In your coaching session with Michael Bungay Stanier you said something I suspect is a big blocker to you building a team:

“One of the biggest arguments I make with myself when I think about putting more resources into the operations side of the business is that I’ve gotten really good advice in the past that your first hires should have a clear line to earning revenue and paying for themselves. And operations doesn’t really feel like that unless it really stretches into sponsorship operations.”

Which led you to the conclusion that you’d lean more into having your assistant Izzy handle getting more sponsorship deals for you, as opposed to having her in a purely operational role.

There are a few points I’d consider:

1. Who gave you this advice and do you have the same goals and business model? I’ve mostly heard this advice in the context of growing a SaaS product with sales calls and not a creator business (though I’d love to know if there’s a creator business that grew by hiring sales support first).

2. Your core business model. You run a founder-led creator business without sales calls. Your main product is a membership for creators. Yes, sponsorships are a revenue stream of the business but it’s one you’ve been working to become less dependent on. So, what would it look like for the first hire to directly generate more revenue for your core business?

   1. Growing top of funnel (more content, better-performing content, better-converting content, exploring new marketing & sales channels, strategic partnerships)

   2. Increasing conversion along the customer journey (lead magnets, email welcome sequence, landing pages)

   3. Increasing retention of the Lab (identifying retention-drivers, improving membership experience)

   4. New offers (though this shouldn’t be a prio if we follow your more-better-new framework and your plan to take fewer moves, bolder strokes)

3. Your goals. You want to work less and double the business. A sales hire should generate more revenue but does not have the potential to lead to less work for you. An operations hire should lead to less work for you and could lead to more revenue if a) they scale your marketing operations along with the rest of your operations, b) they improve retention through better operations (leading to better, more consistent customer fulfillment), or c) they free up your time for higher-leverage work that generates more revenue.

4. What other successful creators have done. I’ve often heard a competing piece of advice from successful creators like Ali Abdaal (paraphrazing): “Your first hire should run your operations and hire and manage the rest of your team, so that you’re no longer the bottleneck to growing the business and team.” You’ve brought up this same point, too. These two pieces of advice are at odds with each other. You can’t hire someone whose main job is to free up your time and at the same time immediately justifies their salary by bringing in more revenue. You have to pick your path to scaling. And to me, the business you say you want looks a lot more similar to someone like Ali Abdaal, whose first hire, general manager Angus Parker, is still running Ali’s operations and managing and growing his team. This leaves Ali free to work on the business and the few activities that only he can do as the personal brand of the business.

5. Clockwork vs. EOS

You brought up the Entrepreneurial Operating System (EOS) created by Gino Wickman and it sounds like you want to use it to scale Creator Science. But according to the EOS-creator, it’s not the right framework for your situation.

Gino Wickman wrote the foreword to the book Clockwork by Mike Michalowicz in which he maps out three stages of business. Stage one is figuring out if entrepreneurship is right for you. Stage two is about surviving the startup phase: “you must extract yourself from being the linchpin of the business so it can run without dependency on you. This is the Clockwork stage.” Stage three is scaling with a full operating system and where EOS comes in.

This places Creator Science at stage 2 where the Clockwork framework is most useful.

The reason I’m hammering on this point is that last year, I guided a boutique consultancy through implementing EOS. Despite getting mentored by a business owner using EOS, this did not lead to the desired productivity jump, because the founder remained as the bottleneck. Looking back, I realize that the EOS framework doesn’t include tools to remove the founder as bottleneck; it’s designed for a more mature organization, and Clockwork would have been the more appropriate framework for the job.

The central premise of Clockwork is that a healthy business should be able to run without its owner for at least four weeks. You probably already know the book well (given that you’ve interviewed the author) but in case the Clockwork process isn’t top of mind, here’s a quick rundown of the steps:

1. 18 months out: Declare Operation Vacation. Start by picking a date for your 4-week vacation that is 18 to 24 months from today (you have a slightly sportier timeline, Jay)

2. 17 months out: Run a time analysis. Track and analyze your time for at least one “typical” week and complete all other Clockwork exercises for yourself (this includes identifying the QBR of the business, the Queen Bee Role)

3. 14 months out: Tell your team. Invite them to ask questions, ask for support, establish better cross-communication among team members (clear line of responsibility for each role, daily huddle)

4. 12 months out: Cut down on doing. Have a team meeting to determine what you need to stop doing (Trash, Transfer, Trim, and Treasure all your actions), discuss any concerns of the team, cut your Doing workload to under 80 percent of your time and push your time toward Designing, stop being the only person serving the QBR

5. 10 months out: Deeper cuts to doing. Run fresh time analysis, confirm you’re under 80% Doing work or better, meet with team to cut Doing time to less than 40%, allocate freed-up time to Designing

6. 8 months out: Measure progress and establish backups. Run another time analysis, confirm you’re under 40% Doing, commit to achieving 0% Doing withint the next 60 days, meet with team to plan & measure progress, identify backups and redundancy for each person

7. 6 months out: Run a test. Take a one-week vacation out of town without internet, have a team meeting on your first day back, review what did/didn’t work, make improvements and fixes

8. 4 months out: Run more tests. Week 1: another one-week vacation test, week 2: come back to debrief and fix roadblocks, week 3: another one-week vacation, week 4: debrief & fix

9. 2 months out: Plan full disconnect. Run time analysis to confirm you’re at 0% Doing work (if not: make plan to get there immediately), make a communication & emergency plan for the 4 week vacation

10. 1 month out: Act as an observer. Observe the operation, delegate any remaining work, document loose ends and give them to someone else

11. 1 week out: Take a vacation at work. Goal: have no Doing work, no deadlines except self-imposed ones; delegate any secrets you’ve been hoarding for yourself

12. Operation Vacation.

13. When you return: Debrief meeting on day 2, then every week for 4 weeks; schedule next 4-week vacation for 12 months from now

6. Fewer moves, bolder strokes vs. growing the business

One of the lessons you took from the author’s retreat are James Clear’s words “fewer moves, bolder strokes.” You want to do the things that you do with more excellence and more intensity and more intention. Which I love because this reminds me of my favorite diagram (from the book Essentialism):

But then you said that this is the tension you felt when it comes to hiring, “because again, there is a world where instead of hiring to add more capacity, I reduce the scope of what I want to do and just try to be more excellent in a smaller number of things. I think both are viable.”

So it sounds like you see two opposing directions for your business:

1. Stay small and do less, better

2. Grow the team and do more

But I think there’s a third option, scaling, as Mike Michalowicz describes it in Clockwork:

“Growing a company is different from scaling it. Most businesses grow. Very few scale. You grow a business by doing more to get more. You scale a business by doing less to get more. They are different orientations. Extremely different.”

He suggest shifting to questions like “How do we halve our efforts to double the output?”

…which I now realize sounds veery similar to your big question this year: “Can I reduce the time spent in the business without reducing the value the business creates for the audience and the value we capture in the business?”

So here I am, again, telling you something you probably already know.

I still decided to bring it up because here’s what I’m worried will happen if you look at hiring as synonymous with doing more:

• You’ll use hiring as a reason to take on more projects (you already have a backlog: virtual summit, Studio coaching app, new Instagram strategy)

• You’ll free up your time and immediately fill it with tasks that don’t fit into the existing team structure

• You’ll feel guilty spending time working on the business because it will look like the opposite of doing more (and it’s a new type of work which you need to give yourself time to learn how to do)

Hopefully this can help you take your own advice of building a simple and elegant business over a complex one.

You said in your conversation with Michael that you feel like a passenger in your own business right now. I’ve valued everything I’ve learned from you this past year, and in return I’d love to help you get back in the driver’s seat.

I’m excited about where you’re taking this and rooting for you either way. And if you want to talk, you know where to find me :)

Cheers, Anna

I pledged to do things differently this year and this public letter is the first step. I’m looking for an entrepreneur whose mission I believe in enough to help build their business as if it were my own. If you’re a founder who recognized yourself anywhere in this letter and want that kind of energy on your team, I’d love to talk: anna[at]theannareich.com