I spent $600k on coaches (so you don't have to)

Do coaches actually get results?

This is the written version of this week’s bonus Youtube video. The video is the full, unedited, chaotic version. This is the good bits, organised by taking the transcript and having an AI tool (Claude Fable) clean it up. [Watch it on YouTube]

A few years ago I paid someone $100,000 to spend two days with him in San Diego.

By the end of the first day, he’d told me I shouldn’t even be running my company. The day after those two days ended, I had a pretty huge panic attack. And it was still some of the most profound coaching work I’ve ever done. I’ll explain in a minute.

Since starting my business in 2011, I’ve spent somewhere in the range of $550,000 to $600,000 on coaches, mentors and masterminds, and that’s before counting the flights, the hotels, and sending my team along too. So when people ask me the question I was asking myself ten years ago, “is any of this actually worth it if you’re running a small business?”, I think I’ve earned the right to an answer.

Below are three of the roughly 25 coaches and mentors I’ve worked with, the three most impactful recent ones: what each one cost, what they told me, and what happened to my business when I just did what they said. I’m using these 3 as a way to kind of tell my story around the value of coaching and to keep the story grounded VS vague.

The nuggets (if you only read one section, read this one)

1. The ROI of a great coach is usually one conversation, not the whole package. My first ever call with Sam Ovens lasted about 20 minutes, and my audio was broken the whole time. What he told me in those 20 minutes became the template for a program that has since made over $20 million.

2. Just do what they say. If someone is more successful than you in your exact domain, don’t debate them, just try it and see what happens. People in the mastermind kept saying “this wouldn’t work in my industry” or “this wouldn’t work in Europe.” I’m European, I was selling corporate training, and I just tried it. It worked.

3. The most successful people in the mastermind showed up the least. They’d appear once every six months, ask one question, get their answer, and disappear to execute. The people on every single call were knowledge gatherers, not action takers, and they were the ones struggling.

4. Coaches are for seasons. Sam was right when I needed hypergrowth. Blake would have been useless to me then, and Sam would have been wrong later. Figure out what season your business is in before you figure out who to hire.

5. Don’t try to extract every cent. The people who got the least out of these communities were the ones grinding to get their money’s worth on every call, annoyed whenever a topic wasn’t relevant to their business.

6. Paying for expensive things teaches you to sell expensive things. We paid Blake $100,000 for two days. We came home and started charging €100,000 for two days with us, and sold four of them in the first 12 months.

7. No coach will take you from 0 to 1. If the business barely exists yet, save your money. You still have to be a person who can just do shit.

Okay. The three coaches.

Sam Ovens: the $36,000 mastermind I barely used

Around August 2020, our biggest course at the time was making 130-something K a month, but it was plateauing, ad prices were climbing, profit margins were down to 15 or 20%, and I could see it slowly falling apart. The business was also getting really stressful to run.

Then a designer friend of mine, Ran Segall, messaged me: “Do you know about Sam Ovens’ Quantum mastermind?” The concept was $36,000 per year for a weekly group call with 15 to 20 other entrepreneurs, plus four trips a year to LA to hang out with Sam. I’d never been in a mastermind and didn’t really get it, so I asked Ran for his logins (hope it’s okay that I keep telling this story, Ran) and binge-watched the recording of Sam’s most recent three-day virtual event.

Myself and Laura at Sam Oven’s office in LA

Something clicked. We were 20-something people making 2.5 million. Sam had a very similar business model with nine people making 12 million. Our system was incredibly complicated, ten funnels, tons of content. He had ONE funnel and made basically no content. Something was going on there.

So I joined. My first call with Sam went like this: my audio was broken, there was a big echo, and I sat there going “hey Sam, hey Sam, hey Sam” in front of everyone while he stared back with zero facial expressions (he’s not unfriendly, he just doesn’t do facial expressions). Then he gave me about 20 minutes of information: the VSL funnel, his Facebook ad system into a call booking setup, and the pricing structure he’d use. My team and I executed on exactly that, and it was the beginning of the hypergrowth stage of my business. The facilitation business fucking exploded. Two years later we hit our peak revenue, $6.3 million with a 50-something percent profit margin, after being plateaued for about a year.

That pricing suggestion became the template for Workshopper Master, which is still the most successful product we’ve ever made: 903 active members, $5,000 to $7,000 to join, over $20 million cumulatively since 2020.

Here’s the funny part. I stayed in Quantum for two years, spent at least $120,000 all-in (we even sent our sales team to hang out with Sam’s sales team), and almost never showed up to the calls. The other thing Sam gave me had nothing to do with funnels: watching him coach 30 people at a time while keeping his energy low, not performing, just staying his slightly weird self, is a big part of why I can make videos like this one at all.

You can’t join Quantum anymore, by the way. Sam shut it down while we were still members to go build Skool.

Bryan Franklin: becoming a sailboat captain

I met Bryan through a stranger. Someone recognised me at a conference breakfast in Nashville, we got talking, and I asked him the question I ask everyone: what’s been the biggest thing for growing your business lately? He said working with an executive coach called Bryan Franklin, and I asked for an intro on the spot. (It then took ages to arrange the first call. Bryan, I love you man, but you are busy as fuck.)

Bryan is an actual executive coach, the only one of these three where coaching is the real job. His website says he’s helped 12 startups reach 1 billion, and I don’t doubt it. We paid him around €75,000 a year for two years: a one-on-one call every two weeks for me, the same for Laura, plus occasional full-day in-person sessions at something like $15K a day.

Laura and Bryan cheersing after a successful coaching sesh in Austin

On our very first call I told him: dude, I am so bored of running this company and I don’t want to do it anymore. We’d hired so many people that everything just worked, I didn’t know what my job was, and I was 33 and wanted stuff to do. He gave me an analogy some of you will have heard, but I hadn’t, and it landed at exactly the right moment. You spend your 20s like you’re on a speedboat, foot down on the gas, burning as much diesel as possible, running on fear and status, and that fuels the company’s growth. But now you’re the CEO of a multi-million euro company, and you need to become a sailboat captain: let the wind and the momentum that’s already there push you, and calm down.

The thing that made Bryan so valuable is that I could never predict what he was going to say. I have ADHD, I’m always guessing someone’s next sentence, and if I guess right I’m bored. I’d come to Bryan with “here’s my problem, there’s option A and option B, which one?” and he’d show me there were ten other options, many of them better than anything I’d thought of. The best coaches give you the courage to do the thing you already knew you should have done in the first place.

One example. Laura and I met him in New York for a one-day session and presented every direction we could take the company, because Workshopper Master had been running for two years and we thought it was basically done. He looked at our numbers and said: you’ve struck oil. This course is the oil. All you need to do for the next two years is build new and more efficient refineries and drills to get that oil out. Stop thinking about everything else.

It was so relaxing. I always have 30 to 50 ideas, and he gave us permission to drop almost all of them. He was right too: there was still probably 10 to 15 million left in a program we’d mentally written off. That one day cost $10,000 or $15,000. You can guess the ROI.

Blake La Grange: $100,000, two days, one panic attack

The most recent one, and the most intense. Blake’s deal was $100,000 up front plus a share of any growth in the business on top, and most of that 100K was those two days in San Diego. We went in with a very specific goal: take Facilitator from $6.3 million to $10 million a year over 18 months.

At the end of the first day he said: Jonathan, you don’t seem like the type of person who’s the right fit for having even a six point something million euro company. You seem more like an artist. He’d noticed the only time I got excited was talking about my music and art projects, and whenever I talked about growing the business I closed up and went into what he called “German mode” (I live in Germany, he enjoyed that one). And Laura, my fiancée, who runs the businesses with me and was sitting right there, said: yeah, that’s true.

The mad and mysterious Blake with Laura in San Diego

That’s the thing the best coaches do: they see what you really want but won’t allow yourself to do, and they keep digging until you admit it. Blake told me I’d never like running the company the way it was, that I’d always be fighting my own personality, and that we should stop the 10 million journey entirely. Pursue the creative projects wholeheartedly and they’ll make a lot of money. Banging our heads against 10 million would just be an unpleasant burnout waste of our time.

The day after those two days, I had a pretty huge panic attack. It was that intense. And then over the next two to three years the business transformed massively, all of it traceable to that one weekend. We recorded the “future of AJ&Smart” video that’s still on our homepage, repositioned the whole company around bringing joy and creativity back to your OWN work, and finally used facilitator.com, a domain I’d bought but had been too scared to use. We killed the internal rule that every product had to make at least €1 million. I started Already There, the digital detox art retreat I’d wanted to go on myself for ten years. And Blake basically invented our “guides” model: instead of me being the face of everything and hiring more and more facilitators, the top people in our community now pay a yearly licensing fee to be trained by us and take on client work on behalf of AJ&Smart. That became a whole business in itself.

One more thing. Blake sold us this $100,000 deal in a Google Doc, on a call, no polished proposal, and I remember thinking “this is so janky for such a big deal.” Then I thought: well, if he can do it, we can do it. We came back to Berlin and created the Two Day Growth Jam, two full days with me and Laura at the AJ&Smart office, €100,000, jumping straight into your biggest growth blockers. We sold four in the first 12 months, and closed one of them over a call and text messages. Spending big money on yourself unlocks the cheekiness to charge it.

Even the thing you’re reading right now comes out of the Blake reframe. In the old AJ&Smart, an hour-long unedited video would have been the stupidest possible use of my time. Now, if two of you read this, connect with it, and in two years come to an art retreat or a business thing I run, that’s already worth it.

So, is it worth it?

For me, obviously, yes. But I’m not selling you coaching (I don’t offer any, and two of these three don’t anymore either, one of them is off making a movie, so this is not an ad and there’s no affiliate anything). Here’s the actual nuance.

You have to be coachable, and a lot of people just aren’t. The format matters less than you’d think: Sam was group calls, Bryan was a formal call every two weeks, Blake was hanging out on the beach for 18 hours straight. What matters is picking someone who’s ahead of you in the exact season you’re in, doing what they say without ego, and then going home and executing, because nobody, at any price, will do that part for you.

And if the money feels scary, that’s partly the point. Paying the 36K made me take it seriously: when Sam said something, we just did it.

Cheers,
Jonathan

P.S. The full video version of this is on the YouTube channel, with the actual screenshots, the pricing breakdowns, and me getting interrupted by a wasp nest situation on my balcony. If you know one business owner who’s been going back and forth on hiring a coach, send them this.

P.P.S. Blake has actually been on the show. If you want to see what he’s like, search “a personal talk with my mentor” on the channel. He kind of coaches me on air. Fascinating guy.