Random Thursday email/video for you about something I wasted WAYYYY too much time trying to figure out.

How do you figure out what to pay yourself as an entrepreneur, as a business owner, and how much do you leave in the business?

This confused the shit out of me for the first 10 years of running AJ&Smart, and I probably lost ludicrous amounts of money doing it wrong. I don’t even want to think about it. It’s painful.

So let me try to simplify it for you, because I really wish someone had simplified it for me. (I’ll put the video here for those of you who just want to watch or listen):

Quick note before I start: I’m talking here about when you actually have a business with its own bank account. In America that’s an LLC, in Germany it’s a GmbH, you can also do this as a GBR. If you have a very big business, you already know the answer to this. If you’re just doing freelance work, you maybe don’t need this. This is for people running a small business with a few people in it.

There are two camps

When it comes to paying yourself in a small business, there are basically two camps.

Camp 1: Take what you need, reinvest the rest

This is the one you’ll find when you search online. It’s the one mentors tell you. Look at your personal expenses, make that your salary, and leave the rest in the company bank account.

Why would you leave it in the business? Safety. Growth. Whatever it is. People in this camp will tell you the only way to grow is to keep reinvesting the profits and take the minimum you can take. They’ll also tell you it’s better for taxes, because you don’t personally get taxed until the money moves from the company account to your account.

Camp 2: Take as much as you safely can

This one says: look at the profits, and take as much as you safely can.

What does “safely” mean? Everyone has their own level. Usually you’re looking at how much cash is in the company bank, as in, how long could this company survive if we stopped making money today or had a couple of bad months. Some founders leave three months of cash in the bank. Some say six. Some say twelve. It’s based on your risk tolerance and how predictable you believe your business is.

I’m somewhere in between. I usually sit around nine months. Right now I think we’ve got twelve, but sometimes that’s just because I forgot to think about it.

So at the end of the year in this camp, you’re going: okay, we made a million, 400k of that was profit, I’ve taken a small salary that covers my baseline expenses, now how much of that 400 can I take while still keeping however many months of cash I want in the bank?

What I was doing (and why it was wrong)

Because most people were telling me to, I was doing Camp 1. And it seemed logical. The business is my investment. The asset is my investment. Taking the money out just makes the asset more risky, and I’ll get taxed the second I take it out anyway. Right?

What I did not think about were the negative side effects of Camp 1, which were pretty severe.

What Chris Do told me

A while back, when we were around 30 to 35 people and mostly a UX design and Design Sprint agency, Chris Do was hanging out in the Berlin office. (If you don’t know Chris Do, look him up, he’s an Emmy award winning designer and a legend.)

I told him I wasn’t feeling it. Not enjoying it, not really motivated to keep going. He asked how much I was paying myself. I told him: a minimum salary, basically what I needed for my expenses, plus a little at the end of the year. The number was roughly in line with a standard UX design employee at my own company. A bit more, but relatively in line with what I’d get paid as a UX designer somewhere else.

And he said, well, that’s your problem.

As the business owner, you have all the risk. Your employees have none. If you have a bad month, you don’t take a salary. If the company goes bad, you’re on the line for everything. I had the maximum risk and I was taking basically the same reward as everyone else in the company.

So I wasn’t seeing any tangible reward for growing the business. Yes, I had access to the money in the AJ&Smart account, but it wasn’t really mine. I knew that a couple of bad months and it’s all gone, eaten up by the business. My money was directly tied to every risk the business had.

His point: you need to feel the effects of this money on your personal life. If your life is exactly the same, if you’re still being super careful with money even though the business is making four million, something is off. I kept thinking “why don’t I just get a normal job?” That’s the problem when you’re not paying yourself in line with the risk and effort you’re taking. You get disconnected from the whole point of why you started, which was to build a business, work for yourself, and have your own thing.

Part of the issue was that I was getting advice from people who thought of us like a startup, not a bootstrapped small business. There was no investment in AJ&Smart. We started getting clients and grew from zero. There’s no real exit either. Sure, I could sell, but the deals are always kind of shit. So by not taking the money, I was just getting more and more disconnected from the point.

What Jason Fried told me

Jason Fried runs 37signals (Basecamp), so I won’t introduce him. Years ago he told me the same thing, more bluntly: it’s a terrible idea to leave the money in the company. Take it out, always. No one ever went broke taking a profit.

Here’s roughly what he said:

Unlike companies that reinvest all or most of the money back in every year, 37signals takes the profit out each year as distributions to the owners. This means every year they take risk out of the company. Companies that keep reinvesting keep adding risk. And when the company ends one day, as they all do, they’ll have enjoyed the upside as it went, instead of waiting for an outcome that might never come. They work to enjoy the now that’s guaranteed, not the future that isn’t.

You don’t hear people say this, especially because so much of our business advice comes from Silicon Valley and books written by people trying to build something massive. In that case it does make sense to reinvest and take investment. But if you’re a one-person show or a three-person show, you’re just creating a shit ton of risk for yourself.

He’s got an article called “Why we choose profit,” and the line that stuck with me: profit is the ultimate shield against bullshit. On the company level, if you’re actually profitable and not just burning cash, you don’t have to work on projects you hate or with people who suck. It gives you options. On the personal level, if the company’s burning you out and you’ve been taking the profits along the way, you have more options to walk away and do something else. If you stay on Camp 1, waiting for some imaginary day when you finally take the money out, you often never get there.

The zombie business problem

Think about it simply. Say you’ve got 2 million in the company account and your yearly costs are 1.5. You have a bad year, you get sick, COVID happens, the market shifts, and that year you’re not profitable. All that saving you’ve been doing is now essentially gone.

Here’s the trap: the company keeps going. So you get a false sense that things are working and will be fine, because you’ve got so much cash in reserve. But it might actually be a signal that the business is dead. You’ve got a zombie business. You see this with startups sitting on leftover investor money that just can’t die.

At AJ&Smart, our UX design work became a bit of a zombie business, because there was so much cash in the machine that I didn’t notice for a long time that it wasn’t really working. We could run months and months in the minus and it was all fine.

Cash also makes you do stupid things. A couple of years ago we had something like 18 months of cash flow, because I hadn’t taken it out (I need to reinvest, I need to reinvest). Someone came in and said let’s invest some of what’s left over into building something. I said cool, let’s do it. It dragged on for a year and a half, didn’t really work, and at least a million euro that’s no longer there. I could have taken some of that as a distribution and started the Unscheduled CEO thing sooner, with less pressure on us to do well.

The risk-reward thing

People will tell you that you should distribute profits to every single person in the company. Sure, if they also have the same risk. Meaning, if they also don’t get paid when the company isn’t making money, if they have to use their own money to keep it afloat, if they have to go to court if bankruptcy hits, like you do as the CEO.

The owner takes more money not because they’re an egotistical maniac. It’s the risk-reward thing. If I worked for someone else, my risk is low. They can fire me, but I can get another job. I don’t have to spend the next year or two shutting down a business, dealing with lawyers, and paying back the tax authorities. When a business fails, the amount of years that can drag on for is a lot.

So what should you actually do?

This is my opinion, not fact, but it’s also the opinion of people way more successful and way smarter than me: take as much as you safely can.

There’s nuance. This doesn’t mean you ignore the future. If you know you want to hire someone for Facebook ads next year, keep that in the company. Plan for those things. But take the rest. Take as much as you can without creating danger for the business, and don’t feel bad about it. That’s what a small business is for.

And there’s a responsibility side too. If you’ve got a few people relying on you, you have to be responsible enough that if the company fails, it’s not from pure negligence.

But here’s the real reason this matters. Another thing Jason said: you’ve just gotta take money off the table. If you don’t, you start to resent your own business. You start thinking “what the hell am I doing this for when I could make the same money by myself?” And usually that feeling means your effort isn’t bearing fruit, your personal life isn’t improving, you’re not feeling financially secure, and the machine is just eating you up while you tell yourself one day it’ll work out.

The whole point of making money is so you can do more of what you want and make more things. I would never have been able to spend my Tuesdays (and now a couple of days a week) messing around on a weird little art-business project called The Unscheduled CEO if I hadn’t been taking profits along the way.

Do this this week

Go look at your numbers and answer two questions honestly:

1. How many months of cash do you actually need in the bank to feel safe? Pick a number (three, six, nine, twelve) based on how predictable your business really is.

2. Are you feeling the effects of your business in your personal life at all? If the business is doing fine but your life looks identical to when you were broke, you’re probably stuck in Camp 1.

Then take as much as you safely can, off the table, into your own account. Don’t feel bad about it.

Cheers,
Jonathan

It’s the second heat wave of the summer here in Germany, 36°C in a country where almost nothing has air conditioning, so this is a short episode. But it’s a good one!

Last week I talked about the ideal business model for a consultant. This week I want to talk about a concept that changed how I sell.

For years I made selling harder than it needed to be, and then I understood one thing that made everything click. It’s a little unfair advantage hack that I rarely hear anyone mention. I use it all the time, and when it’s used on me, it makes me more likely to buy.

Btw last week’s episode looks like it’'ll be the first “non guest episode” to hit 10K listens, wohoo!

Anyway… sales…

It comes down to two things: speed and convenience.

The thing I didn’t get

I’m on both sides of this all day. As a CEO I’m constantly buying services. As the CEO of an agency I’m constantly selling them. And the thing that actually decides whether I hire someone is almost never that they were the best. It’s that they made it easy to start while I was still excited.

In January I was looking for help with the SEO of facilitator.com. I ended up on one call with one company. Not because they were the best, I didn’t do any research. Because they were the first to reach out and they could jump on a call straight away. Then they said they’d go away and make a proposal. By the time they came back, I’d figured out how to do it myself. They didn’t get the job.

Momentum is the whole game

Here’s the truth about CEOs. If you give them too much time to think, they’ve already moved on. The SEO thing was exciting to me for about a week. Then I was done.

So when someone gets on a call with me at AJ&Smart, it’s never about a big proposal. It’s about the soonest possible starting point. Someone wants help with a funnel, I don’t say I’ll prepare a proposal and we’ll have another call. I say: when can we start? This thing starts with a two-day kickoff, and at the end you might not even need us. No retainer to decide, no contract to sign. We just start.

That gives the other person the feeling that this can start now. Because I know they’ve got a million things going on. Right now this is a high priority. In two weeks it’s nothing.

Be the Michelin chef

A friend started a business this week and had a deal slipping. I told him: if you lose it, it won’t be the price or the service. It’ll be that the other CEO lost momentum. We’re so used to doing everything ourselves that if it takes you too long, we’ll just say fuck it and do it ourselves.

Too many of you get on a call, list everything you can do, then go away to make a proposal, then come back, then make the client choose a package. You’re handing the client the job of figuring out what they want from you. You’re the service provider. Be the Michelin chef. Say: this is what I think you need, let’s just start here and see where we get to.

Stop giving people homework

A CEO asks me, “Do you know someone for SEO?” I say yes. Two weeks later: “Oh, they sent me a proposal, I haven’t looked at it yet.” That person gave them homework. A lot of entrepreneurial people have that now-or-never thing, and a long proposal is a task they’ll never get to.

The best proposal anyone ever did for me closed a 100K deal in a Google doc, live, on the call. By the time we hung up, that was the deal. We started, I flew out, the paperwork happened in the background, and neither of us cared because we’d already begun.

Stay disconnected from the money

The move is to say: I’m excited, I can do this, let’s start. This is roughly my price. If it works out, my finance person will sort the contract. I want the client talking about the project and the dates, not the contract. If you’re a one-person show, your partner or a family member handles that part so you can stay on full speed.

And talk the price on the call. No jump scare in an email three days later. “Ballpark, around 15 to 20.” If you can’t say that on the fly, get better at running your business.

That’s the concept. Speed and convenience. Once I understood it, selling stopped being the hard part. You don’t need a better script or better marketing. You need to stop making it a job for people to say yes to you.

Cheers,
Jonathan

this week I want to try something a little different with the pod: i’m adding an enhanced summary of the “main takeaway” of the episode for those of you who prefer to just get to the good stuff and skip the rest.

Of course I still think you should listen to the full episode to get the context, or at least put it on in the background while you scan through this. But whatever way you like to consume my content, enjoy!

So!

Here it is:

The problem I had

Most consultants sell exactly one thing, and it happens to be the most expensive, hardest-to-buy thing on the menu.

It’s the lowest leverage thing too, meaning you have to put in a lot of time to get paid to do this… which takes away from being able to actually run your business.

For me it was selling design work to clients. Meaning the more design work I did, the more I would get paid. It was a 1:1 relationship with time and money.

Around 6 years in to my design career I learned that there was a completely differently way to approach running an agency, a completely different set of business models that I had no idea about… and honestly I wish I had known about them from the start because GODDAMN they changed everything for me.

Let me show you the other things you could be selling.

The three rungs

Every consulting business can be split into three offers.

Done For You. You do the work. The client pays top dollar and gets your hands on their problem. This is where almost every consultant lives, and most of them never leave.

Done With You. You don’t do the work. You teach their team to do it. Workshops, training, group coaching. Cheaper for the client, way more leveraged for you.

Do It Yourself. Courses, books, content. The client never interacts with you at all. Cheapest rung, fully scalable.

When AJ&Smart was a UX agency, Done For You was us running design sprints for clients. Done With You was teaching their teams to run sprints themselves. Do It Yourself became the Design Sprint Masterclass.

The part nobody expects

Done With You ended up being the most lucrative tier for us.

Here’s why. You train ten people at a company. Another team hears about it and wants the same thing. Then another. The training spreads inside the company in a way a one-off project never does. And the rungs feed each other: trainings generate sprint requests, sprints generate training requests.

There’s also a second thing that happens once you have three rungs instead of one. On a huge number of our sales calls, when the price for the top tier is too high, we don’t lose the client. We move them down a rung. If you only sell Done For You, every call is all-or-nothing. With three rungs, “no” to one offer is “maybe” to another.

“But my work is too custom to teach”

I said this exact sentence for years. I was certain there was no Done With You version of UX design. Too subjective, too dependent on me being in the room.

I was wrong, and if you’re thinking it right now, so are you.

The goal is not to turn the client’s team into you. It’s to find one fragment of what you do that can be taught. Maybe it’s just how you run a kickoff. Maybe it’s one part of your process. That fragment is a product.

And if you’re experienced, there’s a move most consultants never consider. You don’t only have to sell to clients. You can sell to you, ten years ago. There are people who would do anything to be where you are now, and teaching them is a whole second business. That’s where Facilitator.com came from.

Stop selling your time

The last piece. Once you have your rungs, price them as packages, not hours. No day rates, no itemized lists of what’s included. The moment you itemize, you invite people to negotiate you down line by line.

A rule of thumb I picked up that’s stuck with me: one month in your group program should cost about the same as one hour alone with you. That gap is what makes the cheaper rungs feel like a deal and the expensive rung feel exclusive.

Do this this week

1. Write your three rungs. One sentence each: what’s your Done For You, what could your Done With You be, what could your Do It Yourself be? Don’t build anything yet. Just name them.

2. Find the teachable fragment. Ask yourself what you do that feels boringly easy to you but looks like magic to clients. That’s your Done With You seed.

3. Add a down-sell to your next sales call. When someone balks at the price, instead of “no problem, bye,” try: “There’s another way to work with me. I can teach your team to do this themselves.”

4. Price by the rung. Top expensive, bottom cheap, and stop itemizing.

You don’t have to build a course this month. You just have to stop being a business with one product, where that product is the single hardest thing on the menu to say yes to.

Cheers,
Jonathan

P.S. The book that flipped this switch for me on packaging and pricing is Built to Sell by John Warrillow. It’s a short read. Worth doing this week.

I haven’t written something here in a while.. but I thought this could be useful.

DO let me know in the comments if it is.

So last week I ran an event where I hung out with a bunch of consultants and helped them figure out how to get more clients One of the big topics that came up is “what do you actually say on a sales call??”

And here’s basically what I said:

Most consultants ruin sales calls in the first sixty seconds, and they all do it the same way: an awkward intro, then “so... should I tell you what I do, or do you want to go first?”

You’ve just handed the lead the job of running your sales call. Then you panic-fill the silence by presenting your services to someone who never asked.

We’ve used essentially the same call structure at AJ&Smart for years. It was written for selling design sprints, but it’s the script for selling everything. Four phases.

Phase 1: The brain dump

You open. Small talk, then:

“The most useful thing for me would be to just hear where you guys are at right now: challenges, what’s going on. Would you mind giving me a bit of a brain dump?”

Then you shut up and take bullet-point notes while they talk. When they pause, you repeat their challenges back to them: “So one of the biggest things I’m hearing is that every time the product team gets together, nobody agrees on features, and that turns into five or six meetings. Is that right?”

Almost nobody does this. Most consultants are just waiting for their turn to present. Reflecting their problem back, in a clean and structured way, already puts you ahead of nearly everyone they’ve talked to, because they finally feel heard.

Phase 2: Connect the dots

Now link their problems to what you do. But do not present your services yet.

“Based on everything you’ve told me, this is exactly the kind of thing we help with. These two challenges? That’s what we excel at. This third one honestly isn’t our strong suit.”

That last part matters. Saying what you’re not great at makes everything else believable.

Phase 3: Turn the tables

If you’ve done phases 1 and 2 right, they’re now curious. So instead of launching into a pitch:

“I’m not sure how much you actually know about us. Do you have any questions?”

Now they dig the information out of you: what’s the service, how long does it take, what does it cost. You answer only what they ask. No case-study carpet bombing, no PDF on screen. If they have no questions at all, you’ve lost them. But you’d have lost them with a pitch too.

Two hard rules here:

• Never bring up price until they ask. Price tends to end the conversation; let it arrive on their timeline. (When they do ask, answer plainly. Don’t dodge.)

• Talk less than the customer. If you’re talking more than them, you’re explaining things they don’t care about yet.
  

Phase 4: Close the loop

They’ll eventually say “so what are the next steps?” Tell them you’ll follow up with a short summary email, and book the second call before you hang up. Not “I’ll send some times.” Booked, in the calendar, within seven days.

Corporate deals close on call two, three or four, never on call one. The first call has one job: being the person they want a second call with.

One uncomfortable extra

Clients will never tell you “halfway through, I got a weird vibe from you.” But that’s what loses deals, not your competency. What they’re really deciding is: will this person make my life easier, or be one more fight?

The only fix I’ve found is paying someone (a mentor, a coach) to tell you honestly how you come across on calls. Nobody in your life will volunteer it. I learned I came across as flippant and barely listening, and I’d never have figured that out alone. Knowing it (and naming it upfront with clients) changed more than any script. A great therapist could also work for this.

Do this on your next call

1. Open with the brain-dump question. Take notes.

2. Repeat their top three challenges back before saying anything about yourself.

3. Say one thing you’re not the right fit for.

4. Ask “what questions do you have?” instead of presenting.

5. Don’t say a price until asked.

6. Book the follow-up call before ending this one.

That’s it. The script isn’t clever. It just makes you the rare person on the call who actually takes the lead but also listens!

Cheers,
Jonathan

P.S. Watch this video if you want even more juicy sales nuggets:

After a long weekend camping with the family combined with a hospital visit… how do I still find the time to record a show?

In this episode I talk about how I still get content out there even when I really don’t feel like it.

Cheers,
Jonathan

Cheers,
Jonathan

In this episode you will learn the absolute best way to improve your sales and marketing, and it’s NOT something you hear a lot of people talk about.

Enjoy and let me know what you think!

Cheers,
Jonathan

This week talk about why I haven’t sold my company yet, whether I’m thinking about it and a huge offer I turned down.

Hope you guys enjoy the show!

Cheers,
Jonathan

Enjoy!
Jonathan

And the podcast has a new look and feel this week (if you watch on Youtube anyways!)

This week I talk about the plan to get Unscheduled as a brand to its first million in revenue. It’s going to be a long road, but it’s exciting to start something new again!

Oh, and you can write into the show now too (more on that in the episode).

Enjoy!
Jonathan

This week’s episode of unscheduled is about my new focus at AJ&Smart… or outside of it. Lot’s to discuss and lots more in the coming weeks!

ENJOY!

Cheers,
Jonathan

Get notified when a new episode drops:

https://unscheduledceo.com

My active companies:

AJ&Smart: https://www.ajsmart.com
Facilitator.com: https://www.facilitator.com
Studio: https://ajsmart.com/studio
Partners: https://ajsmart.com/partners

Not in the mood to do a full pod this week so I recorded this little voicenote for you on my drive home today.

Hope it tickles some of you.

Cheers,
Jonathan

I’m a moody, inconsistent, chaotic motherfucker.

But… I still get shit done. A lot of shit! Isn’t that weird?

It’s even weird to me!

Anyway, this episode is about how I actually manage to get myself to do stuff even though I barely know anybody lazier than me.

Cheers and love,
Jonathan

P.S. leave a comment so I know you’re paying attention you cuties!!!!

I recorded a poddy about something I do that makes my life easier. A lot easier! Like… 23% easier i’d say.

Enjoy!
Jonathan

Summer Camp Mastermind Tickets: https://ajsmart.com/summercamp

Get notified when a new episode drops:

https://unscheduledceo.com


My active companies:

AJ&Smart: https://www.ajsmart.com
Facilitator.com: https://www.facilitator.com
Studio: https://ajsmart.com/studio
Partners: https://ajsmart.com/partners

What I do know is that it’s STILL my job to make sure my company both survives and thrives through whatever happens.

Here’s my plan to deal with it.

Summer Camp Mastermind Tickets: https://ajsmart.com/summercamp

Get notified when a new episode drops:

https://unscheduledceo.com

My active companies:

AJ&Smart: https://www.ajsmart.com
Facilitator.com: https://www.facilitator.com
Studio: https://ajsmart.com/studio
Partners: https://ajsmart.com/partners

In this weeks episode of the Unscheduled CEO I show off my very simple system for turning strangers into clients.

I also review some new water and talk about videogames.

Oh, and I announced Summer Camp 2026 which you can get tickets to right here: https://ajsmart.com/summercamp

Today between 3-6pm CET, i’ll be running a live, free crash-course on how to generate leads and close deals.

You can register and join with this link.

Though it’s focussed on getting Facilitation clients, it’s going to be relevant to anyone looking to sell anything essentially.

It’ll be a fun, info packed, informal 3(ish) hour session. You can join late and just hop in if you’re seeing this after 3pm…. annnnd…. well that’s it? SEE YA.

Cheers,
Jonathan

P.S. there won’t be a recording, so if you miss it, i’m sorry :(

This week I talk about the biggest problem i’m seeing with CEO’s using AI tools. Hint: THEY’RE MAKING LESS MONEY BECAUSE OF IT.

But it’s even worse then that, because while they make less money, they get more and more lost in the AI-HOLE.

Listen or watch on Youtube for the full breakdown.

After over 5 years of therapy and COUNTLESS other approaches, I finally faced it last week.

This episode is about what happened.

Oh and also I review a can of sparkling water.

Thanks to everyone for listening to this absolutely useless nonsense. I love you all.

Cheers,
Jonathan

Let’s chat about our first ever Experimental Creative Retreat…

Cheers,
Jonathan

The only question is: what will I do with my new found fame?

Let’s find out!

Cheers,
Jonathan