Guild's CEO and co-founder Ashley Friedlein has been interviewed in a fascinating three-part video story about his journey to becoming a serial entrepreneur. Charles Thiede, CEO and co-founder of Zapnito, guides Ashley through his story from university days to setting up Econsultancy, to ultimately what it's been like to create Guild.

The first part tells us about Ashley's very first ventures during his youth, and the second reveals what he believes to be the best advice for new entrepreneurs at the beginning of their journey, as well as what qualities he feels one might need to follow in his footsteps. The final part hears him discuss Guild's future plans in detail, including how to achieve a £100m revenue business.

The videos are no longer available but you can read the transcripts below.

Video transcripts

Part I

A video panel discussion with Ashley Friedlein. CEO and co-founder of Guild and Econsultancy.

Charles: Hi everybody. It's Charles Thiede, CEO and Co-Founder of Zapnito. I'm here with Ashley Freidlein, who is the Guild founder and former Econsultancy founder. Hi Ashley.

Ashley: Hi Charles.

Charles:       Hi, so tell us a little about you, and where are you right now?

Ashley:         I'm at home. You mean in my career?

Charles:       No, just where are you in the world?

Ashley:        Where in the world. I'm at home in Hertfordshire at the moment and it's very nice sunny day of the year I think, but yes.

Charles:      Yes pretty powerfully rare day in London. Ashley tell us, tell me a little about, tell everybody a little about kind of you and your background, and maybe what you are up to?

Ashley:       Yes, so don't know how far I want to go back. But, I did languages at university. Left. Couldn't find a job. Having studied languages doesn't qualify you for anything. Decided, tried to get a career in TV. Failed at that, but then saw the internet coming in the late 90s and thought "Aha, this is the ways forwards because there's no broadcaster, there's no one controlling the gateway to the audience.” So, I found that kind of exciting, and luckily it turned out to be a good decision to get into the internet, rather than TV.

Ashley:      That was the late 90s. Worked for a digital agency which is now digitized LVI, but went through various incarnations. So, I did a whole kind of dot com boom, and subsequent bust thing, and wrote two books.

Charles:     I was there. I remember that

Ashley:      Yes. When it's two books doing, that's time about essentially about how to launch a large scale commercial website, and then how to market it, and web analytics, Sierra, and content management systems, and things based on my experiences.

Ashley:       Then I set up Econsultancy in 1999. It was called Econsultancy, not because it was a consultancy, it's just a domain name I bought back in 1996 when everything was either Etoys, Ebay, and I managed to get, and thought I'd just sit on it, and then sell it, you know, to KPMG or Accenture at some point.

Ashley:      Anyway, ended up using it to go with the companion website to my book initially, and that started to build a community of people. It was free, but you had to register to get access to some of the content. Then I basically turned that into a business. So I launched it in 1999, but in 2002, I'd come back from a sabbatical and writing a second book. Got some angel investment and turned it into a business, and grew it from there over the next 10 years, and focused on teaching marketing people about how to do digital marketing and eCommerce.

Ashley:      We had some free content, some paid, some subscription member access, and then added events and training over the years, and opened up offices in New York, Singapore, and we did have offices in Dubai and Sydney as well at one stage. So, I grew the business, sold it in 2012 to Centaur Media PLC, which owns Marketing Week, and New Media Age which got folded into Econsultancy, and I'm still there. But, only a day a week now. So, I've sort of gradually wound down the amount of time I spend at Econsultancy or Centaur. But, I'm still there as the founder. But, now involved in other things.

Charles:     Cool, thanks. Let's go even further back to when you were a young boy. Well, so I kind of think entrepreneurs, there's sort of three types – this sort of my take on it – but, there's sort of entrepreneurs that almost are forced into entrepreneurship from adversity, you know, and really have to overcome a lot of odds. There's a second type which is they're kind of, they sort of, exhibit entrepreneurial mind sets from early childhood. They have the lemonade stand empire, or you know, selling Pokemon maybe – although maybe that's before your time?

Ashley:       No, I'm old enough for that! And Tamagotchi.

Charles:     And then there's a third type which is kind of the one that, sort of, creates or decides that's something that they want to do. And maybe there's a fourth type in your case which is, sort of, it's by accident. So, I guess I was wondering what, you know, as a kid, did you kind of display that spirit, or is it something that came on later?

Ashley:             Yes, I think I'd be your second type. I always had – I mean my father had his own business. He was an entrepreneur. So I think that was always normal, you know. So, I think that you're in a family where you see entrepreneurship happening that's just normal. So, it's not weird, unusual, or a strangely risky thing to do, to have your own business. My two brothers, my middle brother, also has his own business. I think that probably rubbed off a bit. But, yes, I always had schemes, you know, money making schemes, or various things, you know, at school and at university.

Charles:     Perfect.

Ashley:       So, not really, to be honest, there's never necessarily about the money per se. It was just about the opportunity and the idea, and then there comes a point where you feel compelled to actually do something about it because you think you can do something better or differently from what is being done.

Charles:     Yes, okay. So you sort of grafting early on, and trying stuff out and getting your friends to pay you money, basically?

Ashley:       Yes, I don't know whether it was on the whole, friends or possible friends and family. But, yes, I had various – at university I ran a band and at university I suppose one of the themes in life I think for me. I was definitely the worst musician in that band. But, I was good at finding the talent and putting it together and marketing it, and turning it into something. I kind of did it because I wanted to be in band. I probably wouldn't of gotten in a band otherwise.

Ashley:       But, then I also created a directory which I sort of sold to people. People had to pay I think it was £2 or £3 to be in this directory... It was a listing of musicians. So, if you paid your money, you got to be in the directory, and then you got to find out who the other musicians are. So, if you are a guitarist and you're looking for bass player, a drummer, or a singer, whatever, this is a way to do it. It was sort of an early publishing business really. A directory.

Ashley:        But, the real reason I did it – apart from making some money, because, you know, it was reasonably profitable if you got a few hundred people signing up – was because I wanted to get and find out who the best people were before anyone else did to form my own band. So, there was actually an ulterior motive.

Charles:      Nice, I like that. I'm going to stop actually on that piece. I'm going to come back to maybe the next part around the journey, and then will get into Guild. So, I'm going to stop there.

Ashley:             Okay.

Part II

Second part of the panel with Ashley: discussing super powers and super weaknesses.

Charles:          I'm back with Ashley Friedlein, who is the founder of Guild, and former founder of Econsultancy. Ashley, thanks for covering off your story and who you are, and the grafting you've done in the past. I guess your music empire never took shape, but it was a good story.

Charles:          I guess I wanted to hear a couple things about your journey as an entrepreneur. What are some of the things that you've overcome? What are the biggest challenges that you've overcome as an entrepreneur, just for others to hear about that?

Ashley:           I mean, there's so many. I don't think I've necessarily overcome anything that anyone else hasn't. But there's the simple things. Finding the money, finding ... Actually, that's the somewhat easier part. Finding and keeping good talent I think is hard. Early on in the journey, you're also selling a vision or a dream, which you've got to take people on with: that's staff, that's customers and prospects and things. That can be quite hard. You've got to have that energy, and keep having that energy, keep believing in that vision and dream, even through the inevitable tough times.

Ashley:           And then you get curve balls. The times where you almost run out of money. The time where I got phoned up by Google and threatened to be sued, just when you're trying to sell the business – when your blood runs cold. I think entrepreneurs know that.

Ashley:           Then also, just juggling being an entrepreneur with your family life, or your personal life, is hard, because you've got lots of responsibilities. You've got lots of things on your mind. Trying to do justice to all those things at the same time I think is hard.

Charles:          Okay, cool. I guess people like to hear about the pain, you know? I think it's helpful for people to hear it. I guess, what advice would you give to ... This is your second, I guess they say big rodeo, if you will. This isn't your first rodeo, which is a terrible analogy. But what advice would you say to first time entrepreneurs, and maybe even second time, in your case?

Ashley:           Don't do it! It's crazy! Hah.

Charles:          Hah don't do it?!

Ashley:           I mean, I think the thing is, it is a pretty brutal thing. I don't know whether it's like, obviously, I haven't given birth. That is incredibly painful, but people do do it a second or third time, and somehow they forget what it was like. Maybe it's like that with businesses and things.

Ashley:           But I think that it is really hard. I've written two books. But sometimes you meet people and they say, "I've got an idea for a book". Or I meet people and they go, "I've got an idea for a business". I think, "Yeah, so what? Everyone's got ideas". Unless you do it – and I'm not going to make you do it – unless you feel compelled to do it, then you're not an entrepreneur, really. Just having ideas is easy.

Ashley:           I find that it's by some weird compulsion that makes people do it. Either you can or you can't. There is this debate around whether entrepreneurs can be made rather than born. I certainly think you can learn a lot of the skills, and you can be a successful entrepreneur by learning things. But I still think there's a lot of nature rather than nurture in it as well.

Charles:          Yeah, maybe it's personality type. Maybe it's a possession. You're possessed by this thing, and you can't control it, right? That's sort of what it is?

Ashley:           Yeah. I think as well, I mean I – for Jeff Bezos, his Regret Minimisation Framework, this idea he said – that when he was deciding whether he should leave his well paid Wall Street job to set up Amazon, that he imagined being an 80-year-old and looking back on his life, and thinking, "Would I regret not doing this?". Then that became his idea.

Ashley:           And I quite like that way of thinking. "I know this is going to be hard. It's going to be difficult. But if I look back on my life, if I make it to being old, would I regret not doing this?". Usually the answer is, "Yes, definitely".

Charles:          Yeah. I think that's kind of what drove me too. I think, "Now, do I regret doing it?". Hah that's a different -

Ashley:           Everyday!

Charles:          Just to end on this, I think it's great to talk about the journey. Then, what would you say is your superpower? Do you have a superpower? Maybe it's your memory? That you forget how hard it is?

Ashley:           Yeah, that's a good question. I think it's having good judgment. I know that's a pretty broad thing... But there's a whole series of decisions you're making all the time. Sometimes even having the judgment to know what is a big decision and what is a small decision is quite a hard thing to know in the moment.

Ashley:           Obviously as an entrepreneur or as a CEO or as a leader, you're making decisions all the time. Sometimes you have to think, "No, this I'm going to sit on for a while", and it miraculously goes away. Or you've got a really big and bad thing, and a lot of that's about judgment. That's a very hard and quite a nuanced thing, and I think quite hard to learn as well.

Ashley:           But on the whole – touch wood – I think that I have good judgment, and have so far been quite good and seeing the future. Or at least seeing to me what seemed to be bleedingly obvious, but which other people see as visionary.

Charles:          Right, okay. Yeah, interesting. I think that's a good segue to Guild, which we definitely want to talk about. Every superhero – let's say you're a superhero – has a super weakness. Do you have one of those?

Ashley:           I don't know. I think – again, because it's almost the power and the weakness is being quite good at most things but not necessarily super good at any one thing. I mean, creative vision, seeing the future maybe. There are certain things I've felt I'm weak at, which I've had to learn. About not being good sometimes always at explaining to people my vision, or stuff that's in my head.

Ashley:           Not being tough enough on getting rid of people quicker. As in, I've in the past I think been guilty of keeping people for too long. Which has been damaging for the business and other people around it. Because I felt bad or whatever, so I think I've gotten tougher on that. But that's something I've had to learn, areas like that. Things I've had to learn and get better at.

Charles:          Yeah, and that's not a bad thing. That's something you learn and you just, after a while I guess you just know when things need to move on. That makes a lot of sense. Okay, great. Well in the next one, we'll talk about Guild. Thanks, Ashley, for this part two of the journey.

Part III

Third and final part the panel with Ashley where Charles asks about new business Guild.

Charles:          Hi everybody it's Charles Thiede, CEO and co-founder of Zapnito, I'm here with Ashley Friedlein who is the CEO and co-founder of Guild and also the former founder of Econsultancy, which was sold to Centaur Media. Ashley, welcome.

Ashley:          Thank you.

Charles:         So this is the third part, where I'd really like to talk about your second – I used the term 'rodeo' – but your second baby if you will, which is Guild. I guess I'd be really interested to hear – at Zapnito and Guild we have really similar philosophies, we just execute those philosophies in a different way. I'd love to hear about your inspiration for Guild. In the last panel we talked about your sense of judgement in seeing something really obvious, so when was it time to pull the trigger on launching Guild? First, tell us a little bit about what Guild is?

Ashley:          Yeah, sure. So Guild is a messaging app for running private professional groups, networks and communities. Some people call it "the WhatsApp for business". Or somewhere between LinkedIn meets WhatsApp. The idea goes back to something that I think I'm quite passionate about – similar to Econsultancy – that is, about people in their jobs, professions and whatever it is they do, sharing with each other, to learn from each other, to make useful connections and contacts.

Ashley:           Personally I'm less bothered by consumer social media. I find it a little bit pointless, or a bit vain, or self-focused. Whereas professional media, to me the point of that is that you spend a lot of time working obviously, therefore you should be passionate about your job. You should want to get better at it. You should want to win respect from your peers. You should want to, when you get more senior in your industry, you want to give back to more junior people, to mentor/teach them etc.

Ashley:          So Econsultancy was set up as a way for marketing or digital marketing people to share insight, tips, contacts, initially, and we built a business around that, a B2B media business. Then, the blindingly obvious thing to me was that the world was going mobile, and was more specifically was going into messaging. I was starting to see these professional communities which had already migrated away from threaded bulletin discussion boards online to Twitter and LinkedIn and things, were now migrating to WhatsApp, Telegram and various other messaging apps.

Ashley:           But that I didn't feel that those platforms which are designed for consumer use were really right or optimised for professional use. So there's no profiles, the search isn't good, you can't edit/delete, they aren't properly private, they're bringing in advertising. I didn't think they were right for engendering the right kind of capturing knowledge, building relationships and contacts in a professional context.

Charles:          Okay, cool. I guess going back to the WhatsApp for professionals metaphor... One of the questions I have is, how do you see you taking that off WhatsApp? Is that part of the strategy? A lot of people are still using WhatsApp for professional groups, it's a very simple platform, it does what it says it will do.

Ashley:           You know, the idea is to learn from – messaging has grown because it's easy, fast, bypasses email, and those sorts of things. So messaging as a medium? Great. And then, why not WhatsApp? You're right. The challenge for us is changing people's habits. If they're used to using it for personal stuff and now they're using it for business stuff, you know how do you change that.

Ashley:           There's a bunch of things there. For us, selling to businesses is not that hard. WhatsApp isn't GDPR compliant, they've got no access to the conversations, they've got no branding, they've basically lost control to Facebook – they don't really like that and would rather it wasn't that way. So for businesses it's not so hard.

Ashley:           But getting users to make sure they adopt it and use it, because they go "oh not another app" type thing, you know that's more of a challenge. That's about the branding, the look and feel, the features, the functionality.

Ashley:          Actually there's increasing evidence that people – not all people, but a lot of people – are getting overload from things like WhatsApp. They're getting confused between work stuff and home stuff, they're posting stuff about the school bus into the office group, so actually people want to split out their professional stuff from their personal lives.  

Ashley: In some ways we sometimes say "Guild is to WhatsApp, what LinkedIn is to Facebook" – but you could say why go on LinkedIn, why not just stay on Facebook? So we'd say yes you can do some of the things on WhatsApp but if there's a better optimised version for professional use, then why not use that for your work stuff?

Charles:           Yeah, I guess privacy, curation, all the things we've talked about as well. I don't know if you've heard the story about the soccer mom group that was infiltrated by someone pretending to be a soccer mom? Do a Google search, it's great, it's sort of like that kind of stuff – I don't even belong to groups because of the noise that's on WhatsApp you know.

Ashley:           Yeah, I find it frustrating to belong to a few groups and I don't know who anyone is. They've got my mobile phone number and I've been added into groups I don't want to be – you are somewhat at the mercy, and frankly, I don't really trust Zuckerberg and Facebook so I feel very uncomfortable about what's happening with my data.

Ashley:          And once they integrate it – now they're bringing in ads, too – but once they integrate WhatsApp with Instagram and Messenger which they're also doing, and I don't know if you've been on Messenger but I had to switch that off after about five seconds... So if that stuff starts coming through into WhatsApp, or vice versa, then I think people will want a flight to somewhere that has a bit cleaner, where there's no ads, there's proper privacy, it's a nice environment in which to do business and talk beyond just chat as well.

Ashley:           We actually have threading – conversations – in our platform rather than just chat. So that we've done deliberately. It's a different feeling – a different purpose, or point, to it.

Charles:          Yeah and I guess what might be interesting to some of our customers, having a professional messaging app as a partner, how would you describe how Guild is different from Zapnito? You know us well, you're one of our advisors.

Ashley:           Well with Guild we only really want to be doing messaging – I mean Guild does exist as a web version as well as the app – but fundamentally it's just a native mobile messaging app. We don't want to do content, content management, we don't want to do events, it's just a messaging thing. Frankly that's hard enough to do.

Ashley:           There are a lot of interesting things on our roadmap, about how do we make that experience better. How do we create trust? How do we build reciprocity? We kind of want to create something which is much more human, which is why we've deliberately called it Guild – to go back to Medieval times really, where we think that a lot of human behaviour, tribal behaviour, hasn't really changed at all. Sharing and networks and peer respect. We're just trying to do that in a messaging way.

Ashley:           I think with Zapnito, I don't think you have a mobile app – I'm sure that the website is mobile optimised, but for me that's more a broader, larger, web-based platform for experts to share – where, yes, there are conversations, but there's content there, there's articles there, there's video panels there. It's a much more content-rich kind of platform, as opposed to only focusing on the quick conversations that suit a messaging environment. So I think they complement each other very well.

Charles:          Absolutely. I kind of see the world in 'jobs to be done', so the Guild job to be done is having the messaging app which is just focused on that, but Zapnito is – some people have said LinkedIn meets TedTalks as a platform.

Ashley:           So we get people asking a quick question or sharing a quick link, it's shorter form content as a whole. If it's longer form, you'd be able to link out to that. Like a video panel like this. We don't do surveys, you'd like out to that, event management, CRM, etc. We talk about the conversation layer that sits on top of, or around, other platforms like Zapnito.  

Charles:           Yeah, that's where the integration comes in. We did quite a bit of research around, we were considering building an app, around branding, white labelling, providing the branding for our clients, people are not downloading branded apps. The app thing is about having a function, and it's not about a brand on your phone. So that makes a lot of sense.

Charles:          I guess my last question is – where do you see Guild going? And what is sort of – what excites you most about the next year?

Ashley:           Well, I mean the next – we're still, we only went live 6 months ago, so it's relatively early days. There's a lot on our product roadmap which we will work on in the next 6 months. The feeling, the brand, we're still working on the little things which make quite a big difference.

Ashley:          Some of those are just features, like @ mentions, replies in threads, doing a search, analytics on the back-end for our admin people, so there's a whole load of stuff that we need to be getting on with. But the most exciting thing is that probably in late October/November time, we're doing a much bigger launch.

Ashley:           We've not really done a big marketing launch yet, it's been through people we know so far. And we have about 50 customers and thousands of users, so still relatively small obviously. Later in the year we will move to a freemium model where anyone can start using it for free.  

Ashley:           You can then upgrade to business or enterprise versions. More like Slack, where you can pay monthly on your credit card, £1 per user per month, so that's obviously much more scalable. At the moment we are having to sell it every time, much less scalable. We've already got good interest from around the world. We're starting to get the network effect, so when people invite other people in, they like the app, they contact us.

Ashley:          That excites me the most. If we can create an amazing product, which sells itself largely through marketing and that network effect, then we're laughing. Our vision for this is to have 100k businesses paying us £1k per year. Which is a £100m revenue business.

Ashley:          It's not having 1k businesses paying us £100k a year. I mean, who knows, we might pivot that way –

Charles:          – there's nothing wrong with that Ashley!

Ashley:          No, there isn't. The vision is a product which needs 10m users, not 1.7bn like WhatsApp or even you know Telegram is at a quarter of a billion monthly active users, we only want 10m paid-for users – but, that's still a big number. The product, the marketing, the freemium – actually focusing on user growth rather than revenue growth is our strategy focus on the back-end of this year and the beginning of next year.

Charles:          Cool, yeah I mean that's exciting that you're going after the WhatsApp model, but you're going to be bumping up against the Slack players as competitors, but I think focusing on the messaging and going after – people are using Slack and they're using WhatsApp, right, for groups, so that makes a huge amount of sense.

Charles:          Exciting times. We're looking forward to partnering, and as clients use Zapnito and then Guild, then potentially integration within our conversations which are focused within the network. Thanks Ashley, we'll be hearing more about Guild from you.

Ashley:              Great, thanks Charles.

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