Will Dayble On Why Starting A Social Enterprise Is A Terrible Idea

Image credit: Leo Flander

Image credit: Leo Flander

Will is a teacher. He’s consistently failed to get a real job, instead working in tech companies for most of his debatably professional career.

He learnt to code in primary school, and has since founded and sold multiple companies, is an award winning lecturer and speaker, and sits on the board of a handful of businesses and non-profits.

He lives in Melbourne, with a neuroscientist and two cats, and plans to retire on Mars.

In his spare time, Will doesn't have any.


Will shares his journey into the world of education & social enterprise, providing insights into dangerous thinking (and doing) habits of social entrepreneurs, as well as asking questions to help people find their feet and purpose.


Highlights from the interview (listen to the podcast for full details)

[Tom Allen] - Could you please share a bit about your background and what led you to working in the social enterprise and education sector?

[Will Dayble] - I wasn't very good at high school. I did a really poor job of paying attention and being a good student and all that kind of stuff. I was convinced I was going to be a social worker when I was a teenager, but I didn't get the grades, which for those of you who know about the grades necessary for social work, it's funny. I don't know if it is the same now, but there's this thing where if you get a really low score when you exit high school they don't even tell you what it is, if it's that low.

I think it's 30% or below or something. I don't know what it is. I had terrible marks so I couldn't do any of that, and so I actually jumped on a plane and went to London just because it was a place to go. I started a web design company in my off hours while I was working at another company. I worked for it when I came back to Australia, so I was working British hours while living in Australia, living in pounds while living in Melbourne. It was really weird, and it didn't work and it was a bad idea and I went broke.

It led to me meeting a co-founder that became my best mate and he and I started a social good tech company together. Does that make sense?

Totally. It sounds like you were learning from those failings.

Yeah. It's funny. How's this, let me give you a roundabout comment on that. I was listening to Freakonomics or Radiolab, one or the other, a podcast, and they were talking about courage, and the whole thing of people that will leap into a burning car to pull out somebody who might die, or they'll jump in front of a charging bear or something, like crazy courage. They were looking into the psychology of courage, and it turns out that all those "courageous" people; they weren't courageous, they just weren't really thinking.

They weren't like, "This is really hard and I'm going to do it." They just did it, and if you asked them, "Why did you do it?" They were like, "I don't know. I was just there and I just did it." There's not really much thought going on. I think I had a very similar thing. There's a fetish these days around failing forward, and failure and all that kind of stuff, and I don't think I even considered it. It was just like I started a company because I was kind of unemployable. It wasn't a really deeply thought thing.

Image credit: Mark Lobo

Image credit: Mark Lobo

Well, I bet it's taken a lot of courage to found Fitzroy Academy. Tell us more about this venture, Will, and what is this platform? How does it aim to support social entrepreneurs?

Cool. This is a tricky one. Maybe I'll give you a really brief history and that might answer the question.


I started teaching at a university here in Melbourne back when I was a tech geek. I had a horrible experience. Just dealing with the administration and being a teacher is horrific. Much love to all the universities. They try their best, same with high schools, it's just, for whatever reason administration within that kind of institution is really hard. It's a really tricky thing. From that experience, I think maybe it was because I'd never been to uni myself so I didn't really know how to operate within that world.

I had from my point of view a really negative experience, and I came out the other side with that classic like, "Man, this system is broken. We need to build a replacement and it's all going to... Disruption. Rah!" I was really excited about that. This is earlier than five years ago. Five years ago I revisited this idea when I got bored of running a digital agency. I was over the internet. I just geeked out on education. I just sat down and read about it a lot, and talked to a lot of teachers, talked to a lot of people that had good and bad education experiences, and just stumbled my way through how teaching works. I found it fascinating.

It's just the most interesting thing ever. It's really hard to explain. For example, if I were to say, "Hey, Tom, your phone sucks. This phone that I've got is better than your phone. Do you want to try this new phone?" You'd probably be like, "Well, I don't care. It's a phone. I have feelings about my phone, but I'll try your phone and then if it's better I'll upgrade." It's very easy for us to upgrade a phone. If you were to go to somebody and be like, "Hey, the way that you think and the way that you've been educated to operate for the last 18 years of your life is wrong. I'd like you to do something else," that's hard.

That's asking people to unknit the way that they were taught to think at a really fundamental level. It suddenly becomes really interesting. To continue the history, so I just geeked on it. I geeked out on education, and this turned into running a very poorly thought out, but very fun one month long social enterprise accelerator. This is like five years ago before social enterprise acceleration was cool. The idea was it was an accelerator for normal people, kind of like the same way that you can volunteer at Greenpeace and you don't need to have any particularly special skills, you just have to need to be like hyped and want to help, and they'll figure out a way for you to help. It was like that.

It was just like, "Let's just get normal people and help them build a company or build an idea or whatever else." It was great and it worked really, really well. We had 40 teachers, 25 students. It was a month locked in a basement of a building in the city in Melbourne together. Really intense experience. It taught us a lot about how almost alternative education works, and just the process of pulling it together meant that a whole bunch of really interesting people came out of the woodwork to lend us their time and energy and ideas and stuff.

We had one of the founders of The Pirate Bay just fly himself over and hang out for a couple of weeks. We had an entrepreneur from, where was he from? I think he was from Czechoslovakia, literally just flew down and rented a house for a month to hang out with us. I think it was because at that time it was a new and exciting idea and people were willing to do anything. The process of running a physical teaching programme taught us really quickly that physical teaching self optimises towards expense. Any really good teaching that's done physical generally runs upmarket and becomes really expensive, really quickly.

If you look at all of the design schools and General Assembly and those physical, even if they're teaching new things, they're teaching it in a physical classroom style model, it gets really expensive, which makes it really inaccessible for the average human. Does that make sense?

Yeah. Totally.

Cool. We learned a bunch of stuff through doing that. I learned that I really love teaching. I really like hanging out with people and being a part of them learning something new and trying it out. That's a fun thing for me now. It's funny, it took me the next five years to go from, "I think this is interesting," to identifying as a teacher, like having that be part of my psyche. We did that really dumb thing where we were like, "Well, if physical education has a bunch of flaws, let's just do online because online will be interesting."

With zero knowledge whatsoever about video or online teaching or anything, I found this lovely guy who made a video for my old punk band 15 years ago. He had actually gone to LA to make feature films and dive into the movie biz over there. He came back to Australia and decided he hated the movie biz and he didn't want to have anything to do with cameras ever again. I convinced him that he should make some videos with me. We basically just dove into trying to do video education, and then three or four years later we are where we are now. It took us that long to figure out how to do it because it's really hard.

What have been some of the key challenges then in setting up Fitzroy Academy and how are you working your way around them?

Good question. Key challenges. I reckon that one of the big ones is that video education sucks until it doesn't. There is so much trash out there. Again, in the entrepreneurship space there's a lot of trash out there, because you have people that ... I'm sounding really negative.

The classic thing that happens is an entrepreneur has some kind of success, they get really excited to help other people experience that success in a really giving, positive way, and so they lay out a roadmap that was their story and they say, "Do my story. Copy paste my experience onto yours and everything will be great."

People buy into that and they spend a lot of money or time or energy on doing that and then it doesn't work, and it feels really weird.

There's a lot of stuff that doesn't work in the entrepreneurship education world. Universities and schools trying to do video education almost never works, because a boring lecturer on video is just a boring lecturer on video. I guess the big challenge for us was I underestimated just how hard it would be to do good video. It's movie making, it's education.

Here's a fun word for you. I didn't know this word existed until recently, it's andragogy.

Unpack that word please.

Pedagogy, as in pedo, child, teaching children. Andragogy, as in andra is teaching man or teaching adults. Adults just learn fundamentally differently to kids. Adults have context and experience and loves and fears and traumas and stuff that makes them motivated to live their lives, really, really different to teaching a kid how to brush their teeth.

We get a lot of really weird things where even in tertiary education we teach young adults like they're kids, and then we wonder why they don't respect the teaching.

Then you add the added difficulty of doing that in video, and we have this thing of like... One of the core fundamental things of andragogy, teaching adults as compared to teaching kids is that it really has to be about the person doing the learning and their context, and their lived experience, and solving the very specific problems that they're coming up against in their particular experience of life.

That's hard to do as a fundamental and it's triply hard to do via video, because it's a one-way interaction. I underestimated how hard all of that would be.

You've spoken about the difficulty of setting these things up, and you've worked on a number of different projects to date. Thanks for sharing those challenges, but overall what have been some of the biggest lessons today that you've learned on this journey of yours?

Gosh. Do you know, it's funny, as I become a better teacher, I don't think I'm a good teacher by any stretch yet, but the more I learn about teaching and the better a teacher I become, the less likely I am to give platitudes and advice, particularly one-directional to a broad audience via a podcast. I really struggle with it. It's like, gosh. I don't know. I almost want to refuse to answer the question, which I know is not helpful. I don't know.

What's a question you'd ask then to a social entrepreneur or aspiring social entrepreneur listening that would help guide them on their journey in the creation or development of their own venture?

That's a really good one. I'm going to answer that question with a question, which I think might get-

We're good at that as teachers!

It might get us slightly closer to a question. You've almost, and I see what you're doing Tom. You've asked the classic newbie social entrepreneur question, which is usually a thinly-veiled version of, "I don't know what to do. Give me a template to follow so that I can feel like I'm progressing." That's one of the questions under the question. The classic follow up to that two-parter is what kind of social enterprise should I start. Should it be a profit share? Should it be a app? We leap to these fundamentals.

I feel like a much more useful question is what form of social entrepreneur are you, and what's your idea of good and bad? What are your values? Is tradition more important than novelty? Is beauty more important than function?

What's a question you'd ask then to a social entrepreneur or aspiring social entrepreneur listening that would help guide them on their journey in the creation or development of their own venture? [Continued…]

What are the fundamental things about the person asking these questions that drives them to do anything in the first place?

It's almost like, I don't know, spending a fair bit of time asking those questions, and maybe those questions are asked over a glass of wine, or they're better asked by doing some stuff and reflecting on the doing of stuff.

I feel like answering the questions about the person's personal motivations for doing stuff is probably a better question than ‘how do I start a social enterprise’, because for the vast majority of people, starting a social enterprise is a terrible idea.

Absolutely. Would you then be implying then that a great reflection for a social entrepreneur would be for them to deeply understand their drivers and where their passions lie, what success means for them, et cetera?

Yeah, like why did you get into this in the first place? What trauma are you working on, or what experience motivated you to get angry about something? It's funny, you see this come out in really confusing ways with some people, because you get particularly young social entrepreneurs at a pitch competition feel like they have to trot out some TED Talk style, "Once upon a time there was a kid who really struggled with problem X, and it turns out that student was me. Here is how I've gotten through it."

We almost want this story of redemption, failure and survival, like this real hero's journey thing. Often it's not that simple, and it's not that heroic. It's like what got you into the first place. For me it's just that I get real angry at dumb systems. I saw education and I was like, "This sucks. This is being done poorly." The efficiency geek in me got all grumpy about it. It wasn't that I had a deep desire to be a teacher or whatever. It's like I fell in love with the job through playing with it.

There's no beautiful creation myth around it, and I feel like for a lot of people if you can get around the creation myth and what ends up on the pitch deck, kind of storytelling through just, I don't know, do you want to make a tonne of cash? Is that the thing? What got you into this? That's a useful question.

I'm afraid of asking questions which then asks you for advice, but from your experience in working with a range of different social entrepreneurs, have you seen any really important traits that are consistent across those that are working really well in the space and actually achieving strong outcomes?

Yeah. Behaviours.

I would say that curiosity and humility, that combo seems to be a really good predictor.

People that are really great listeners; when you can see somebody cognitising as they listen to you, you can see them involving your ideas into their thinking and changing themselves as they listen, like you can see it when people do it and it's just great. You know they're just going to gobble up information that’s given to them and process it well, and then turn it into some kind of respectful, useful action. That's awesome.

I think the entrepreneurship world is really tired of heroes and really tired of visionaries. Humility is a really nice counterpoint to that. It's like listening and then very humbly thinking about something that can be done and going and doing it.

That's very generic, but it's a broad predictor I think.

Totally. Where do you then see social entrepreneurs most commonly going wrong? You've spoken about the danger of not having humility, and the trait of being a heropreneur, let's call them. Are there any typical elements that you think people really need to strongly consider?

Do you mean common pitfalls in things people do or are you thinking personality traits?

Things people do. It could be a mix. It could be a personality trait as well.

It's funny, because I feel like the personality traits are often more useful than what you do as a result of those traits. A lot of the big failures I see are, well, it's the opposite of the others of course. Arrogance is a really dangerous one.

The desire to have an impact is really different to the desire to make a dent. After you've worked with enough particularly young social entrepreneurs, it's really easy to see the people that are working from their own ego versus the people that are in service of a problem worth working on.

It's like falling in love with an area of the world that needs your help and figuring out how you can gently be of service in that area. It's not loud. It's not easily identifiable, so we don't see it much.

The big failure is the loud, "I want to make a dent. I'm going to change the world. Impact at scale, rah, rah, rah," kind of thinking. It's dangerous.

Are there any inspiring projects that you've come across recently then, Will, which you think are creating some excellent positive social change?

Yeah. I'm really excited about SHE Investments in Phnom Penh. It's an Australian-Cambodian partnership between a bunch of people over there. They're focusing on getting women-led micro enterprises in Cambodia that are making a bit of money, and they're helping them make more money. A wonderfully simple thesis. It's like if you're making money, and you make more money, then some good things will happen.

Of course bracketed around that is a whole bunch of cultural and financial and entrepreneurial complexity. The thing that I love about it is that Celia, a Melbourne woman, she went to the place where she works and she just shut up and listened for six months before she did a single thing, and really understood what was really causing some of the fundamental problems behind what she was doing, and then she gently introduced a few ideas, and then they started to work. I think the approach as much as the outcome, I think, is really cool.

She sounds like a great listener.

Yeah. Really good listener. Really good listener. When you speak to her you can see her checking her biases as she speaks. It's a conscious cognitive process. Actually, really similar to another mob that I really like is in New Zealand. They're called Ackama Group. They're basically technology geeks. They're on this mission to do small, not particularly visible technology change that helps a lot of people, so messing with medical systems, tax systems, things that disproportionately affect poor or marginalised people that we don't really care about or don't really notice much.

It's very New Zealand, really humble and in service. I'm excited about them. We're helping them come to Australia to work on stuff in Australia, and it's super-cool.

Wow. That sounds like a fun project! Will, to finish off then, what books would you recommend to our listeners? Do you read many books? Are you an audio book sort of person? Do you just geek out on online articles?

I'm going to give you another really annoying answer. I'm sorry. I'm big on podcasts. I'm a big fan of not only this podcast, but Radiolab is just my... It makes me really, really happy. Also, Julia Galef's Rationally Speaking is a joy to listen to.

I haven't heard that.

Really, really great. She gets really fantastic speakers and she has this marvellous practise at the end of all of her podcasts of asking her guest, "What is a book that you disagree with, that you don't like the book, but you would still recommend it as being well written or a good explanation of the thing you disagree with?" Not "let's stick an arrow in bubbles" and charge down our own well-trodden path. Like let's dig into stuff that we're uncomfortable about. I really like that.

Good, so let me interrupt, Will. What's a book that you feel uncomfortable about reading but you know it's good for you?

Wow. I've never asked myself that question. Do you know what, I would actually say anything by Peter Thiel. I think he's an ***hole. I think he's the enemy. Some of the most negative traits in entrepreneurship are collapsed into Peter Thiel, but I also think he's a genius, and he has a view on reality that is fascinating. I think it's dangerous to use it as an instruction manual, anything that he talks about, says or does, but really interesting as a way of just...

He's almost like, a lot of the things that have come out of Silicon Valley and a lot of things that are really wrong with capitalism are written in technicolour in Peter Thiel.

Image credit: Will Coverdale

Image credit: Will Coverdale

You've given us some excellent insights. I very much appreciate you sharing your experience and your time and your thoughts. You've challenged me, as well, as the interviewer today, Will. I appreciate that. It's helped me reframe some of the questions that I'll be asking in the future. Thanks again.

Thank you. I realise that we basically didn't cover any of the questions that you asked me in prep. I'm really sorry about that…

It’s a good excuse to talk again in the future!


You can contact Will on LinkedIn or Twitter. Please feel free to leave comments below.

Find other articles on social enterprise.