31 Comments

Thanks for the alternative perspective. All the other leadership and agile media tell me, as a product leader, that I am supposed to delegate and keep my hands out of the day to day. But the messy, markey part is what I love. Making something impressive out of nothing is a rare joy. Best of luck on your course!

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Thanks rachel! Was the same for me "delegate everything", but maybe it should be "delegate the things that dont make you special"

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I always deeply appreciate the transparency and humility you speak with. Also the recos. Genuinely can't wait to listen to those episodes for example!

Immediate question that came to mind was, what do you wish you knew way sooner when you started as an entrepreneur?

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I think the only thing I wish I knew earlier was how to deal with feelings of anxiety, what causes them etc. That definitely slowed me down. Everything else, all the other mistakes, I'm glad they happened!

I guess if my mind and body were more healthy in my 20s i'd be more successful now.

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Wow. That tracks with me. Thank you.

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Great episode Jonathan! Really cool that you've enjoyed getting back into the nitty gritty of projects! Nice to be in the position where you can do the bits you love and have talented people around you to take care of the stuff you don't enjoy as much. Interested to hear more about the strategy behind going back to in-person training! My guess would be it's a great chance to get more corporates involved to then sell in bigger training packages to them...? Assume as well there will be loads of amazing content generated by it as well....really I don't know though haha. Thanks for the recommendation to Founders - listened to the first 15 minutes and LOVE IT already.

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Ok it's not that deep of a strategy but here it is:

* You're right that when a company sends an employee to a training with us they almost always book bigger training packages afterward

* The pricing of the events is so premium that it's positioning us closer to something like Stanford D School than something like IDEO. This is something I think will help anchor the pricing of al our other products.

* Speaking of which, our online courses (always known to be the most premium priced on the market) no seem cheap compared to this training. Again positioning and anchoring

* Lots more but I think those are the main.

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Nice, that's really cool. I love how you focus on working out how to increase prices rather than just chasing new clients etc which seems to be what most people focus on. Makes so much sense if you think from the perspective of making more money vs time spent.

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I think it's about that but also constantly wanting to push myself to create something that's "worth" more money than before. It makes it more interesting to me personally

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That's great - I could be wrong but I don't think a lot of people are wired that way! Does the pressure get to you at all sometimes where you think 'Shit now i've got to deliver this thing!' or do you love that?!

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i DO feel the pressure and i do feel worried, and sometimes i do say "why the fuck am i doing this????" but it always produces the best work

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I hadn't thought I was an adrenaline junkie until reading this comment. I've been thinking -- today even -- why don't I just let myself have only a couple of smaller projects going on at once? Is it just because I want to do it all and can't decide. No, it's because it's boring otherwise... Why? Oh... this... I love the feeling of getting to the other side of "why the fuck am i doing this????"

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Ok that's good to know!! Thanks Jon!

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It sounds a bit crazy, but I find it somehow comforting to listen to you. Your brutally honest. Do you ever bite your tongue afterwards? Anyway, I have found being able to give authentic compliments to be the best hack in working with employees. Not too much, but enough.

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Hey! Interesting question.... I don't listen to the episode before I post it (which is why I never know if it's going to sound good). I never edit it (too lazy). But yes, I do worry that some of what I say will come back to haunt me one day - same for when I do coaching calls that are recorded. STILL: it's a fun creative outlet and I wanna keep doing it.

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It reminds me of when a parent actually says that they are having a hard time with their kiddos. It's difficult to say your kids are driving you crazy. Partly because it's more socially acceptable to say everything is rainbows. But I think it's probably more because much of their behavior is on you as a parent. It's like announcing you failed in some way. But the reality is, with all the factors, you're going to fail in some ways. And it's comforting to hear other parents actually talk about it. I think talking about business failures has become more popular/easier, but I feel like you are pushing the boundaries further with talking about employees. And, like with parenting, it's much more comforting to hear (rather than cringy) when you take ultimate responsibility like you do.

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Founders is a great podcast, Jonathan. I’ll turn my focus to those episodes you mentioned.

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Its so amazing!

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I listen to this podcast!

Hahaha

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oh shit

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I enjoyed this episode. Your radical candor is refreshing.

It’s obvious you and the team are brilliant at “productization” and “starting”. Starting is such a big part of what and how you sell.

I’ve finally made it to corporate refugee status. It had to happen this way. WM/IC paved the way for my exit of the corporate world. I’m hoping my ability to sell myself to corporates aids me in selling my services to them soon. Nibbles of interest are coming in.

This is the only podcast I listen to on Substack ATM.

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Hey Jonathan,

Thanks for sharing your journey! It's highly valuable.

If you don't mind me asking,

You shared the story where you delegated everything to the team and then came back to operations.

I'm super interested to understand what the 2-3 key lessons you have from the process of delegating everything.

Is it about finding the right product and a predictable process to deliver to each customer?

P.S.

Love your podcast!

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Hmmmm this is a big topic! here's one off the top of my head though"

* It's very hard to scale "taste" and "intuition". I feel, as a leader I either have to be "completely out" or "completely in". Being half involved in project just irritates me so it's best that I choose which things i'm going to 99% ignore. An example of this is sending invoices to clients, doing sales calls or doing any sort of paperwork.

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So, you would say it's more like a choice which you make and then build a team who do everything. Have I got it right?

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The way it works for me in practice is something like this:

* there are things i will delegate very quickly once ive set the basics up. one example is "creating invoices".

* i wont check in on these things for months, even years, unless they actually break

* other things like this are sales calls. Ill do them myself for a new product until ive mastered them, then i hand them over and dont check again until we start making less sales.

* there are other things which i care about and don't fully delegate, these are things where i think my intuition is important. Things like my podcast, the general direction of our content, designing new products, naming products, pricing our products. These things i will micromanage and never fully delegate.

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Thank you! Super Helpful.

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Dude this is my favourite podcast out of the 100+ I subscribe to. Never miss an episode. I think I like it because it has a good balance of funny / interesting/ useful. I might even get an eight sleep mattress - a guy I work with has one and says it’s the best thing he’s ever bought.

I’d like the Rodecaster to come back with the cheesy intro music.

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Thanks Iain! Rodecaster is still in the mix :D

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Thanks for another inspiring podcast Jonathan. I like that you share insights on running AJ&Smart as well as personal insights in life. I'm a solo entrepreneur and listening to your podcasts does give me a sense of someone coaching me or at least pointing me in certain directions I have not looked into before.

What I'm curious about is if you struggle or have found great ways to balance micromanaging and leaving things (since you can't do everything by yourself right...). My challenge being 'solo' is balancing those things I'm interested in and find fun to do (right now I'm building e-mail marketing funnels) and hiring others to things for me. I recognize what you say about seeing things you would do differently and others who may not see or feel the importance of it.

Great if you keep on creating these podcasts sharing your opinions and perspectives on life in general (just like you recently did when sharing your thoughts about people living from vacation to vacation) and your 'adventures' being the CEO at AJ&Smart.

Always great to see an email coming in saying you uploaded a new episode.

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I think im going to read this question on the next episode because I want to elaborate! Thanks Rody!

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Thanks Jonathan, looking forward to the next episode.

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