From Deliveroo to deliverance: Entrepreneurship lessons with Jonny Burch, NearFuture AI

0:00Welcome to Strategy and Tragedy. I'm your host, Stephanie Melodia. If this is your first time tuning in, then a very big warm welcome. And if you are tuning back, then it's great to see you. If you haven't already, you know what to do. Please hit that follow, subscribe button, wherever you're listening to this. Now, the purpose of this show is the name indicates strategy and tragedy is to bring you the raw, real, authentic stories from entrepreneurs who have been there, done that. And of course, my next guest is no exception. Johnny Birch is a serial entrepreneur, early delivery employee, exited founder and now runs Near Future, an AI transformation consultancy for product and design teams.

0:38As a designer for nearly 20 years, Johnny is the founder of Progression, a career platform for which he raised over$6 million and exited in 2024 before exploring the AI transformation space by day and tinkering in his product studio by night. Johnny, welcome to the show. So, Jonny, I purposely modified your intro. I've noticed that you always go by designer first. So like your LinkedIn headline, what you sent over to me for how to introduce you is very much like I am a designer. And even here, like five minutes in the studio, you've already started talking about design. why is that especially given like entrepreneurship is like so glamorized and I feel like anyone would like cling to have that like entrepreneur exited founder label why is the design thing still very strong for you?

1:29That's such a good question you got straight to the heart of me yeah I mean I've been designing since I was four probably I didn't really know what it was designing and trying to make things work it takes it's now been 46 years since that moment 36 years hang on your skincare routine it's fantastic um uh it's been 36 years since that moment but i have i now realize looking back that's what i've been trying to do for my whole life is trying to make things work yeah and so that might be a business it might be a piece of design or it might be something coded or something else in the world but I think being a designer I think is just so deeply embedded in me and maybe in all designers is very much a vocation sometimes it's too much of your personality as a designer but yeah I mean I have been a founder I am a founder I will be a founder again I'm proud of being a founder and it is a lot of what drives me I've realized that my personality type requires me to make a dent in the universe for better or for worse but the way by which I will always try to do that is with the design skill set that I've cultivated over all that time yeah I can tell like knowing what I know of you it does feel like it really is like in your DNA it is part of who you are and again I just thought it was interesting how you always kind of lead with that first and foremost how close do you think the definitions are between designer and entrepreneur um well i think both sound a bit pretentious as titles maybe uh as an entrepreneur you're a problem solver as well design as differentiates from an artist maybe you are primarily a problem solver it may be visual it may be something else but you're trying to design your way out of a problem or into a solution um and as an entrepreneur boy it's it is just one long journey of it's like a big puzzle that you have to solve in fact a friend of mine a fellow founder who is running a company that is currently going to the moon so he knows what he's talking about he described the the act of founding a company a venture-backed company is being given a load of money to solve a puzzle and how fun is that and actually when you're inside it feels a lot more than that the puzzle is existential um and um all-encompassing and becomes your personality and the challenging in many ways but ultimately you know it's like a rubik's cube i've please may i have a million dollars to solve this rubik's cube and if i do we all get rich but it's got um 16 faces and 42 colors you know it's it's a very very difficult puzzle to solve.

4:27If you like that, and I have always liked that, it's my personality to enjoy that. There is unfortunately nothing else you can do once you've done it. So I'm a founder and an entrepreneur. If you're tuning into this right now, then first of all, a big heartfelt thank you. I really appreciate it. And secondly, there's a very high chance that you're on your own entrepreneurial journey right now. So whether you're a first time founder, and you're figuring things out, and you feel like you're on your own, or if you've done it before and realised that actually this whole entrepreneurship business is a lot easier said than done then I might be able to help you if you feel like you vibe with my energy and feel like you need some of that professional big sister direction support and advice then I'm opening up a few select spots for that one-to-one coaching mentorship and growth strategy for ambitious founders there's a link in the show notes so check it out and I would love to hear from you all right let's get back to the episode going back to the puzzle analogy which I love and you're like maybe on the inside doesn't quite feel like that but like when you are on the inside especially a venture-backed company it's more like a masochistic escape room with that 16-sided rubric's cube and the timers on and the temperature's going everyone's watching and everyone's watching exactly i love that a quick one just on this and we'll get on to like your delivery chapter your business with progression and what you're doing now these exciting topics i'm really keen to dive into but just before we do you mentioning about you know obviously besides them being both wanky titles entrepreneur designer of course at the heart they both share the problem solving one of the most common traps especially for first-time founders is build and they will come so given it's such a natural strength it's such a wonderful skill set that you have in design do you think that that ability puts you more at risk of falling into that same first time founder trap in some ways yes because the dopamine here especially now with all the tools you have I mean I can on the train this morning I built something in in an app that I'm working on in two hours that probably would have taken me actually so long I wouldn't have bothered to do it in three years ago and I can write code but I would have been like that's I need an adult to do that for me I'm not going to try and do that myself and instead me and Claude just sort of worked it out you know these stories are everywhere that's not an unusual story yeah but what it does is every problem starts to look like Claude's Claude's problem to solve and it starts to look like a build another feature type exactly yeah I do think designers really good designers have a good sense of the user and they do stay problem focused and they can smell bullshit basically so if given something or if they created something and it doesn't feel good i think a good designer will always get nervous if they haven't validated what they've built yeah but so that i think unlike i mean engineers are sort of obviously the canonical example of the build in build in your bedroom for five years and then get surprised when no one wants what you've built um i've done that but i i i hope that what i'm doing by building a lot is building to tear down and building to exactly so it's a validation process rather than like exactly more stuff on top exactly every time what about the perfectionist trap like i know so many wonderful designers who are just like they will not release it from their claws until it is perfect and of course perfect is never achievable yeah yeah i mean i think um there's lots of different types of designers actually uh and some are more into the craft and and uh it's incredible and you see incredible work from them and actually in this new world that craft and creating truly sort of novel visual things is going to be very important um i'm not one of those designers i'm very much a like build the first version test it somewhere it's a sort of 80 and i've got like a good design so it's not it won't look broken yeah but it'll be a basic enough to test like there'll be a little bit of brand work there'll be like the colors will be sort of matching but it's not going to blow anyone's hair back yeah yeah yeah and that then is the point at which i'll be like i don't want to spend more time on this until it's until i know that there's point spending time in it good good that's just that's just i think the process that increasingly people are going to be moving towards yeah i hope especially embracing that entrepreneurial thinking the line beta now better later comes to mind honestly johnny there are 50 000 more where they came from when you've lived in startup land for a decade and a half everything's a hashtag everything's got a saying yeah okay all right let's kind of move move over to the next chapter early deliverer employee how exciting so what was the year what was your role paint the scene and especially take us to the small office in was it soho with will yeah take us there yeah sure um so i had been uh the first employee a small startup bank in 2012 i think i joined okay um would we have heard of it what was the yeah it's called osper bank for kids it's like a precursor to the monzos and and in fact a lot of osper alumni ended up at the other fintechs uh but it's great fun i mean i I joined literally the founder.

9:50So, you know, that had been three and a half years of my life. And I'd interviewed this guy and he was great, a designer. And we made him an offer and he said no. I was gutted. And I was like, where's he going? He said, I'm going to this place Deliveroo. Hadn't heard of it. Went on the website and it was like non-responsive and there was grass along the bottom of the website. Like it was, I mean, and I'm sure Will and others would admit now wasn't well designed. So I was like, why is this designer going to this? It looks really crummy, frankly. And we're this cool, we just got millions from Index and we're like the cool, the cool FinTech on the block at the time.

10:36And he went over there and then a year later, I had decided, I think I'd sort of started to realise that Osprey wasn't, going to win the market and I wanted a change and I started looking around and at that point Deliveroo had in one year gone from under 10 employees when he joined to I don't know 100 odd something like that and so he interviewed me and I said yes that's so funny how did that feel with the tables being turned um it's great I mean I knew I wanted to work with him anyway yeah so and actually in the year between we'd gone for coffees that's so nice how do you build a design team and how do you you know just like general startup design yeah cool so we'd stayed in touch a little bit um so it was a no-brainer really but i um interviewed in an office in noho uh that they good street was it i can't remember where they hadn't moved in yet so i i got interviewed in an empty office and um and simon my boss said you know we're gonna move in soon and then this is a big enough office our current office is too small so this will be our office and three months later after i worked out my notice period i moved in and they were too big for the office that they had not moved into three months earlier jesus so i was roughly employee number 150 wow so fairly early um definitely in the first sort of flush the culture in that place was um i mean testament to that culture is that a lot of the people i worked with then we still talk daily wow that's amazing yeah we're in alumni slack channels and things like that so it's like really powerful built really through food i think yeah uh lunch is coming in every day we were the biggest dog fooders of our own product will were is an american like uh he's kind of a like broey slightly bro-y culture so it was like food eating contests and people would be playing music from their speakers while other people were trying to eat as many hand rolls as possible and so it was like you know it was a specific culture and I think every early stage startup to be successful needs an opinionated culture as soon as you start trying to cater to everyone then it's important but you do start to lose a little bit of that focus yeah and it's okay for different companies to have different cultures.

13:03This one was quite a, you know, like, you know, which is great. And, you know, lots of memories in the pub and everyone used to go to the local pub and then lose their laptops every week. And then they had to say, you can't take your laptop to the pub because there was so many laptops lost. I don't want to sound like one of those founders that loves in office and blah, blah, blah, but there was something about being in a room, working on a problem that was very far away from being solved. everything on fire numbers through the roof you know we would go down every sunday if it rained on a sunday we were knackered because our infrastructure wasn't anywhere near able to cope with the order numbers oh so we just grew so fast wow it took me a sec to connect the dots on the raining i was like right new office whatever like if it's raining on a sunday everyone stays in and orders do you know there's a correlation between the temperature and hind soup sales right so for every drop of degree centigrade the hind soup sells by whatever percentage yeah it doesn't surprise me same here with deliverer in the rain yeah so it would just like go through the roof every time it makes sense yeah we you know uh like a lot of companies at that time we were trying to work out personalization and recommendations and how can we know what people ultimately want uh by showing them something on the feed so i was looking after all of the mobile apps at the time uh design of them uh and um working out you know what do you show someone and i think there was a bit of research i have vague memories of this it was 2016 or something when we were doing this work but um but we would watch people browse all of these interesting and unusual restaurants and then order nandos like every single time it's like the person i want to be versus the person i am this obscure sushi restaurant that you know looks really interesting i'm getting a lemon and herb wrap i just can't and it was decision paralysis you know it was the classic that's interesting if you give me five things versus 25 things yeah i will i will more likely order fight from the time interesting were there any other more sort of psychological insights that you learned from that experience at delivery delivery oh yeah i mean there's so many stuff uh a lot because i worked on the consumer products and so it's effectively a funnel like you're working people from opening the app yeah ordering ordering yeah um a lot of that was like small changes making big impacts when you're dealing with 100 000 orders a night or a week or whatever it was um you get data back fairly quickly about even a small change um one of the most interesting projects i worked on was you know on the other side of ordering once i've ordered immediately i'm nervous like i'm like come on i'm i'm hangry basically i'm waiting to for my phone to tell me when my order's coming where is it nowadays you see this in all the apps they all have the trackers yeah and you know you know where your driver is all the time none of that existed anywhere no one had that so we started to build all of that technology in and interesting stuff like the first version of the tracker you could see a map the moment you ordered but then people get really annoyed because they'd be like my my driver's not moving for ages and ages of course not they're still cooking the food but they'd be like going on the complaints line and being like it's going to be late even though it wasn't even late at that point yeah so we ended up hiding the map until the point and it sounds obvious now but at the time you're rolling this stuff out and sort of feeling your way through it this is so interesting it's so interesting to like be that close and seeing how users actually interacting and again before all these other like little nudges and little psychological little user interface features existed funny you mentioned about the map and the tracking because i was exactly just about to ask you true or false because this is like room around startup land that's just come back into my mind talking to you now is it true that delivery did the wizard of oz behind the scenes or the mechanical Turk is the other term for it where somewhere your order's being prepared your order's in the kitchen it's on the way it's was there somebody manually behind the scenes doing that i don't think so that was a rumor that circled around i think maybe dominoes did that oh dominoes had the first ever tracker they had that face and i think they still have a face i think that was because i remember looking at that when we were talking about ours it was it wasn't a map or anything it was just it had the four stages yeah you could sort of yeah the face would light up or yeah yeah so interesting suspect there was a certain amount of mechanical turk in that yeah yeah but yeah that was a rumor that circled around and and interestingly what i learned from rory sutherland on the psychology the user psychology on that tracking is the same with uber which is i actually don't mind so much if it's an extra few minutes or whatever i just need to know it's just the certainty so it's that same sort of frustration that you talk with the map and like yeah even like use of color like what color you make things as people have very different reactions to that yeah we built a whole load of stuff this is before ai and you know any of that um effectively like menus in the app where you could drill down into exactly what was wrong with your food after it arrived too cold missing item etc etc and that was a way for people to automatically solve their problem rather than get on a call or get on a live chat so great user experience yeah but it also allowed us to model um what complaints were and who were serial complainers so we could say if you've had 10 orders and you've not complained about anything we probably will just give you some money if you complain because you're probably telling the truth yeah if you start doing it more often right we'll we'll change how we react yeah yeah makes sense being much more data driven there so all that kind of stuff it all happens you know you think and i find myself thinking this it's just an app why they're 150 designers working on it um you know with all these things and it's so complex it's the tip of the iceberg moving things along our next chapter following delivery was you launching your own business progression so tell us what progression is was and crucially why did you want to go and set up your own thing yeah so i uh was had been talking to a couple of friends who i'd worked at osper with actually while i was at delivery and we had this little slack channel back when slack was fairly early and you got an unlimited um message history on the free tier so we just had this like slack channel where we were like wouldn't it be cool if wouldn't it be cool if and we were sort of edging towards starting something together so in 2018 we all quit um a friend sile who had been at uber and my friend who'd been at palantir and me and we came together and we were like right we have a plan we have an idea within a couple of weeks we'd invalidated that idea so we were like okay well next idea uh what was this first idea it was actually uh income smoothing for gig workers so i don't know at that time that was when the gig economy stuff was really all over the papers yeah and makes sense with your role at delivery being close to it yeah exactly so um we went off to do that and sort of couldn't that first idea wasn't a goer but we we kept moving and we went through probably five or six different ideas where we spent a month we built something basic we went and did some validation with potential customers and we got to a point I think it was probably four or five months in where another idea we'd been like some of us had been hot some of us had been cold and um i was like i think i am possibly the problem here basically like they were quite often more aligned than i was so i was like i think even if we find an idea that we all agree on initially this might i might not be helpful to them and i might not be i might not enjoy myself loads so i decided to bail um and the day that i decided to bail was the day they started the next iteration of a company that is now called metaview very very big um hiring company uh they they run basically ai interview transcriptions and you do interview intelligence and learn about how this is for um hiring so um i'm watching them do amazing things but at the time that then left me with like a blank sheet of paper i was like i could say that was interesting and go and get a job could even probably go back to Deliveroo if I wanted to but that felt not like the right move so went on holiday and floated around in a swimming pool in Italy for a week and the day I came back I built a one-page website in a day progression.fyi it was like a thing in the back of my head I'd found annoying at Deliveroo we'd built this career ladder in Excel and it had taken ages you know tons of people involved goodness knows how much person time hours cost we'd incurred like expensive people in a room talking about one sentence for an hour right um all for it to fall a bit flat on its face and this was the goal of this document was to help people understand how to grow in their design career and then ultimately um in their whole career and it sort of hadn't quite worked I was like I bet other people do this as well so this website was basically a list of the public ones see what happens I was doing it alongside a couple of other things I was also playing around with yeah but it just it popped um as they say uh-huh uh and so I was like oh okay well I suppose I'll do this then and it was just pulling a thread for the next year um how are you defining it popping what happened I posted it on LinkedIn and a few other places and it sort of did the rounds I don't know um Hacker News and various other websites I'm not a good good at like promoting I don't have a strategy for any of this stuff like I'm just like once I put it on LinkedIn and Twitter I'm out of ideas basically at that point so if something does well then that's like a little bit of a signal to me it still is so I was like okay well I'll carry on doing this without a plan no co-founder no money just like I'll just do some consulting while I work out what this is And can I just ask, sorry, at this point, you mentioned no money.

23:32I was going to ask this before anyway. When you previously left your job, was it just savings that you guys all had together just to kind of have that run away? Yeah, I'd given up two years of delivery stock two years before they IPO'd. Oh, let's not dwell too much on that one. Yeah, yeah. I don't, to be honest. Good, good. I don't, I'm very much a no regrets person. Love it. Okay, fantastic. But yeah, like I have a history of questionable financial decisions. you're an entrepreneur of course it's like oh you gotta just follow my heart to the end but yeah anyway so this turned into like keep pulling the thread i built this like weird bad product that i sold to monzo and a couple other people as like a one-off sale just basically people who believed in me and were like you can do this i'll buy this from you i think and sort of validated it basically and by the end of 2018 i was like i need to build a proper app this needs i know what this needs to be it needs to be sass with recurring revenue i don't know how to do that so i went to find a co-founder and found neil on a forum uh and by april 2019 we had built a first version we had our first customer first paying customer uh and we bootstrapped for the next year until in the throes of covid decided to go and raise money so we then raised money 2020 and 2021 and built a team and sort of went from there.

24:53Wow incredible my goodness so there's a few things that stood out to me a lot about that story one was actually going through the validation process that's where I reacted live in the moment because like the amount of founders who are just again fall into that common trap that I mentioned right at the top of this interview which was like I've got this great idea I've got this vision I'm going to launch it out there and again build it and they will come but actually putting it to the test yeah and I feel like you sort of blew past getting the validation for progression i mean one thing is putting together an mvp but what were some of the other signals so you said okay you got picked up by some pr which is fantastic yeah um your first paying clients as well is is phenomenal can you is there anything else you can break down on the validation manual i worked my network i had you know i was i'd been running a design team in london so i'd done some conference talks and you know i had like a bit of a network to sort of show first versions to very much like i'm not trying to sell this to you please tell me if i'm wasting my time basically yeah um trusted people so there was a bit of that there was a bit of like trying different things i could sell so actually workshops and like very much not products where i could just get in a room with a bunch of designers yeah um at the time and and be like here's career paths what do you think about them like let's talk more yeah building credibility myself but also try not understand the edges of this problem and i think i think if you think about the very specific thing you've built as a thing to validate then i think that's going to be hard but if you have a thesis about the world yeah and you're loosely held about what you've built or what you even want to build and you just think i think that this problem exists let's find out if the problem exists first of all do i believe in two years time this problem will be solved by someone what evidence do i have that that might be true like people are already paying for things or there's some pull from someone in the market like i can point at someone who is paying money to solve this somehow if you start there rather than start from i built a thing um then uh then it's a at very least it's a healthier a way to go about and you won't just completely burn out after you won't just throw away the whole thing baby with the bathwater if that first month doesn't go well yeah the other big mistake i'm see people making is quitting their jobs and like cutting off they're like i'm going all in month one is i'm going all in and then by month six sort of things have got quiet and then they get another job and it's sort of you have to think of it as a long game um you can go and raise money but you shouldn't assume you can and once again fundraising is lumpy today for sure like if you tell the right story you'll raise too much money and if you tell the wrong story you won't raise any so um i'm a little bit out of the fundraising cycle at the moment but definitely talking to other people i get the sense so assuming it's going to take you a while work out sustainability how can you work two days a week which at least pays the rent so that you don't have that fear all the time that's like palpitation in your heart um thinking i'm making a fool of myself here and i'm just gonna have to go crawling back to my job and then no i hope no one will have noticed you know yeah um and that that will come a certain amount but i think being able to just go i love this problem i think i'm going to spend a lot of time with this problem over the next year and if it turns into something that credibly I could build and excites me and I can get other people excited about then great and sort of leaving it there I think is a healthier way to go such wise words Johnny I love that pearls of wisdom that was gold dust absolutely spot on absolutely spot on with all that I couldn't agree anymore you mentioned fundraising what can you share on your fundraising journey with progression obviously bearing in mind like a big caveat to this is like time and place so this was a different time especially the fact that you were building this b2b sass company which was like the magic words that like all the investors were like jacking off to in like 2020 and 21 right it was like b2b sass given to me the same way we're now living in in ai right so we can draw some parallels but what struck you the most about the fundraising journey oh boy what was like easier harder

29:29uh i think you start from a point of view of like i want to raise money i don't know anyone at least i did i mean probably if you've come from a background of in venture or you've done one before which i would now i would have a black book but at the time i was like i know maybe one person that has done this and actually that one person's enough so if you have one person that has cut a few angel checks um or knows someone in vc and you're just honest about what you're thinking about and you don't say i'm fundraising you say i want to understand how this works i think that surprised me how generous so many people are with their time and i met some fantastic investors really early i was so lucky um i should call out someone sarah drinkwater who is now runs um a fund common magic she's a solo gp female solo gp is extremely rare she's an incredible person but she was so supportive from the very start she'd just like get on a call with me and i'd be like i don't even know if i want to fundraise just terrible stuff you shouldn't say that kind of stuff to an investor and i'd say it anyway and she'd be like okay well you know i've committed to investing in you um so i'll just pretend i didn't hear that um but yeah i i mean there is a story you have to tell and but it there's a chicken and egg you have to learn what story you need to tell by talking to people and them being kind enough and you being open enough to hear when they're saying i'm not going to invest here's why and you really internalize that don't ignore it some people will give bad answers like it's too early or like vague mysterious things cheering you from the sidelines is the big trope like they'll say we really believe in you but it's not quite right for us right now we'll cheer you from the sidelines fuck off um it's what they're saying basically but um the ones that give you feedback and i had i had a few uh investors that said no um first round capital i remember this was actually our second fundraise a guy called todd who actually runs an excellent podcast um but he was the most such a thoughtful no and i really tried to like listen to everything he said and make changes to the story and then those no's start to you know the first time it actually took us three months to fundraise um and the first month was like an absolute howler i mean i was asking i was like pitching to raise 150k at one point i was like i don't know what i'm doing literally and and it was only through the kindness of strangers where i turned what i was doing into something that looked credible and looked like something they should even listen to and ended up um with an amazing lead guy called Pietro from Connect who is like this effervescent Italian um just like so full of energy loves b2b sass oh my god this guy loves b2b sass so much uh so just like just energy match completely amazing um but yeah I think there is no doesn't you can listen to the podcast and you can read the books just have to start showing people what you've got yeah yeah and that classic line of if you want advice ask for money if you want money ask for advice right that's exactly this it's true believe that totally true so one last question on the fundraise before we get to a bit of a turbulent exit here is i mentioned earlier about sort of like the state of the world and how much sort of time and place sort of feeds into it headwinds and tailwinds how much now with hindsight obviously it's still difficult to say but with hindsight how much of kind of the market headwinds do you think had to do with the success of progression yeah well we were born in ZERP the ZERP era which is the zero interest rate that all the P stands for I can't remember but basically that time when it was you know low interest yeah every tech company was doubling headcount year on year yeah exactly it was just like everyone jobs for everyone you know this was the time when all of these big u.s tech companies completely overhired and now you're seeing them you know the other direction yeah exactly but that was great for us we sold by the seat we were effectively an hr product every time someone joined a team we get an extra seat quits in um and there was a lot of money for employee perks basically your your employees sticking around was the biggest piece of value you had as a company so from 2019 to about late 2022 that was true then russia invades ukraine all of the stuff starts happening in the world that effectively makes tech um less investable so interest rates go up so therefore all of those people that could have put money into tech could now actually put money into like four percent get four percent on cash or you know do do less risky things for their money um so less money going into tech these companies start shrinking all this starts happening at the same time as two or three big um much bigger hr tech companies than us started building progression like features into their apps so it was a it was a kind of uh pincer move where the hr team that previously would have bought us is being told you can only buy one tool so you need to pick the one basically with the most features and all of these companies started building all of the features of each other to start looking more like a platform and we were in the middle so what i spotted this well neil and i spotted this and um i think there's a certain amount that we couldn't do anything about it you know if you look at what we pitched in 2019 and you were to try and pitch it now I'm not sure you would raise money for it because I think it was a good idea then exactly genuinely and I'm not sure it's a good idea now yeah the way that we were building it um but I think there were things that we could have done and when I think of my um leadership journey and like all of the lessons that I've learned and I've had now a year nearly 18 months to reflect on on that time being decisive if I see something and I believe it to be true it doesn't matter if I'm gonna have to have a difficult conversation with an investor or I'm going to have to let some customers down or I'm going to have to tell the team that we're doing something different it's got to be done I am actually the person that knows yeah yeah I'm the person that thinks about this in my sleep as well as in the daytime yeah I'm the person that's told the story the most I'm the person that's met the most customers I'm reading all the tech news more than anyone in my team so really I should be doing this I suppose it's just a very big trust your gut yeah yeah have a more conviction right yeah and I think you know when I think about how lossy the world is because people when they know something to be true don't want to act on it it's extraordinary how how much is lost in years of people's lives where they're in the wrong job and they don't want to be there but they're worried about something or they don't want to tell someone a bit of news and they sit with it for months or years carry it yeah and that person meanwhile is causing chaos or unhappy themselves just there were there were moments there are a few moments like that yeah um but i hope if nothing else if i build a team again yeah but i will be able to practice a bit less ruinous empathy yeah so but all of that is to say i think when we saw in late 2022 what was happening we could have made a more decisive move at that point and actually what we did was we waited another year and at that point we still had lots of money actually and when we sold we were profitable and you know that there's a a healthy company and a going concern but it wasn't venture scale and as soon as we realized that our story was no longer a venture scale story once you've taken VC money then that is really what you should be aiming to do so we could have um I don't know what the pivot would have looked like necessarily but we could have done something more dramatic earlier and instead I think I was a little bit indecisive yeah yeah what basically what that resulted in was we kept going until when would it have been

38:19very end of 2023 first month of 2024 Neil and I sat down and we were like what should we do and it was probably a year too late that we were having yeah we were like what should we do and we sort of made a decision we'd been exploring a pivot we were like it's kind of interesting but it's hard to go from a company with some decent revenue and a whole team built around it and all of this work to say we're just going to lose all that and just work on this tiny little thing that we don't even know if it even exists yeah um and to you know we had to tell the board about that and it was that was a whole thing so we were like you need 150 energy to activate something like that do we have that energy yeah uh and the honest answer was no basically yeah uh and we talked to our investors who are great throughout and we said right well we'll position the business for an exit we'll run it we'll position it for an exit and that was january um and can i just fact check here sorry because this is like you mentioned venture scale before so are these investors do you manage their expectations that like they're not gonna get like 10 times yeah roi a vc makes 10 bets and one needs to go to the moon and then three need to pay the money back and then the rest can die they won't get their money back so that is the math they're already doing yeah so you know you're you're so deeply emotionally involved in this thing that you're like oh my god right i think they might cry yeah yeah like in the nicest possible way they've seen it before yeah exactly you know you're they're probably talking to five other companies that they're on the board of having similar conversations at the same time so you know they care of course and they want they want what's right for you and what's right for the business but you shouldn't worry too much about them yeah exactly and so you fall into that middle bucket of like we're going to position for an exit we're going to get a return but it's just not we're not that one percent yeah yeah we're not but yeah exactly yeah yeah okay can i just also throw before we move on i want to just i just want to cut you a bit of slack on because i did want to talk about the leadership journey saying about how big the team had grown but there's so many other topics we need to get into so we will move past that quickly but on acting on the decisions that you need that you know you need to be making it does link back to what you said earlier about for all the podcasts you listen to and videos and other and chats and everything else until you're out there yourself a player on the field putting in the reps doing it for real this for you was your first time in this position this was the first ever time and not an excuse but also cutting you a bit of slack here because you've never been in charge of a team of this size you've never had your own investors this is uncharted territory and the fact of the matter is the market just doesn't give a crap right and so i think it's only a mistake when you don't learn right like you do it once you learn from it you move on but if you keep making that same mistake then you know it is a failure so you've learned from it move on but like completely you're fine i think it's a balance you know i don't lose sleep um because of decisions that i made at progression and we we treated our employees well like you know i like to think that we were it was a good chapter in everyone's lives yeah made new friends um i learned a ton and yes the market doesn't care absolutely you're right um it cared for a while and then it suddenly didn't care for us so that was a really interesting journey yeah um you'd be remiss to not try and take learnings as well like there's things that i did that yeah that i overemphasized yeah but i would not this time so yes I agree I agree with you but also you know if there are learnings to be had I'm gonna and a common theme like throughout this podcast and all these entrepreneurs that I've had the pleasure of interviewing as well it's like that has been a very clear commonality of just like not acting fast enough whether it has been laying someone off which I think you've been in that situation as well pivoting sooner uh going out there to sell your business sooner just moving quicker it's just and i think with and then when i've also sat down with like serial entrepreneur that have now got a few of those under their belt now that again where it's simultaneously been the most common thread throughout all these interviews i've done it's also been mirrored on the people who have got the reps under their belt to now just move quicker and quicker i think so i think but you need to go through it I feel like you need to go through because sorry just to your it is so uncomfortable and it's like it's so uncomfortable that we'd rather sit with that than confront the decisions that we need to make and so it's like you know you can tell a child don't put your finger in the flame it's gonna burn but until they do it there are just some things where you're like can you shortcut it it needs to be burnt into your memory there needs to be the scar tissue the personal right right okay so moving on to the exit chapter then so you started you had the awkward conversation with the investors more awkward for you than it was for them they're like it's fine so what happened what's your drama with the acquisition yeah so uh we our goal was to get the company to the point where it was uh potentially attractive to a strategic investor so that would be one of the big hr platforms where there was strategic value in slotting a tool like ours into their existing suite so you know think your your high bobs or your personios all of that that kind of crowd but we also wanted to explore the idea of selling to a another founding team that didn't want to start from scratch so we sort of had to like balance this what the company looks like um across both like healthy enough and great tech and and um team comes with and all of that kind of stuff for one group of people while also here's what it could look like run in a sort of skeleton way or or sort of rebuilt uh we learned a lot about that and ultimately we we found one buyer in i think about march april um we went through two or three months of due diligence with them uh they then turned around i think the day before we were meant to sign the terms and decided to half the price uh so i think we said something like no uh but let's stay in touch uh because you know when you don't have anything else on the table at the time you're like oh my god maybe that was our last one maybe that's what we should actually be you know expecting yeah um and then a second one came along um a european roll-up really nice company gotten really well with them um it was a healthier offer than even the first one had been before they halved it uh so we were like great back into due diligence with them validating uh and we got to the point where we're about to sign and then a guy calls me on the phone on friday night um i remember it vividly i was in my garden with my at the time two-year-old i think and um i i chat to this american guy who's no no in fact sorry no he i get an email to our info at progression.co uh something like um are you open to the idea of partnering from tech ceo um and i was like uh yes my number is this feel free to give me a call and while i was in the garden i was like this is going to be bullshit basically calls me up and um he was like yeah uh so tell me what's going on and i said we tomorrow uh or monday we're going to sign uh final papers to sell the business uh here's the number that you would need to say in order for us to tear that up and go with you and he said okay i'm gonna think about it and then he called me back later that night and he said we'll have an loi to you tomorrow morning i said it's got to be tomorrow and we've got to have some validation that this is real because i'm going to burn that bridge that's the the bird in the hand he said i understand and i said i think uh and i even like renegotiated 10 more or something like that um or no i i tweaked the um the package that neil and i would get after the sale to sort of sweeten that a little bit yeah and um i was like oh that was a mad 10 minutes uh and then he he came through next day uh and we had a uh an loi uh sent it to our lawyers and they said yeah this looks legit so we signed it and it's still scary because you go from you know full legals done quite costly through to back to square one and he said we'll get it done in a month and you know americans think you get everything done in a month it took us three months to then go through legal process again ended up being 100 grand in legals for the whole thing um but we signed uh and so you know i didn't have many true ceo moments i think in my journey a lot of being a founder is boring and not glamorous and you don't feel like the big man necessarily but in that moment i was like yeah i felt like sort of mad men or like um i don't know um just like like i'd sort of yeah exactly exactly i felt like i'd earned my title for just uh a few minutes there so johnny that is so crazy that is so great so this american randomly through our support you know through our support line how did he come across you i actually never i don't i don't remember if i asked but i can't remember this is the this is like every time my partner comes home after hanging with these and i'm like ask the first most basic questions like oh no i don't know i didn't even i'm like johnny that's like the first question i want to know is this marketer in me i'm like attribution yeah yeah where did they come so funny it's like my wife i'll go to the pub with my mates and my wife will be like, how are they?

49:13Exactly. I was like, didn't you guys talk? It's such a classic trope. So, but those are just so crazy with the timings here. The timings of it. So were the other guys pissed? They were incredibly gracious. Again, I think you go back to like professional investors. Yeah. They want to do the deal and they put time into it and they really did put time into it. But they also understand how this works. Yeah. and we had had up until that point a lot of tyre kickers so we had really we'd acted in good faith throughout and i did say to them you know it was like double what they'd offered so i was like did you have to understand that we have to take this and he understood did you give them an opportunity to counter offer yeah of course and they didn't yeah they couldn't match it wow yeah god that's so crazy i co-bought my last property in the same way i saw it on the friday went to see it got my partner in on a saturday the deal the offer was put in on the sunday and we were like yeah contract on the monday yeah it goes to show also going slightly off track and i know we need to keep things moving but when people this is another like big not just like in business but like life lesson and think like with anyone with anything when people want to like they'll make it happen yeah do you know what i mean it's like if you want to sell your company you'll take that call on a friday night if they want to buy your company do you know but like if people want to yeah and i i I don't know whether this is just more personal to me.

50:39If anyone else relates, please leave a comment. But I find myself subconsciously and way too frequently making excuses for other people. And I thought I'd learned that lesson. But I keep, and I'm like, if someone wants it, like they'll, we'll make it happen. Yeah. And so it's just like things, they don't have to be so difficult or take so long. Or, you know, this narrative that I feel like we get fed sometimes. I think it's actually key, especially at the moment. But I think it's key a key skill to have as a founder or a leader to constantly be asking that question yeah there's this i think it's almost um cliche but if someone says this will take a week ask them genuinely how do we do this in a day and it may not be possible in a day but what you're really asking is do all of the things that you have assumed need to be true or need to exist do all of them need to exist let's go back to first principles right and really just like right work out how this can be done yeah yeah are these just like artificial blockers slowing us down you actually do you actually want this is this you actually committed what's and what's actually important about it versus what's just what we always did in the past and you'd be amazed how often people just build all of these towers for themselves yeah exactly where they have to do it yeah yeah and you're like why it's like an extraordinary waste of time yeah this is where like some people don't want the entrepreneurs like anywhere near like don't ask why don't ask questions and it's also why being i think being a founder sometimes is annoying yeah not entirely compatible with being a friend exactly to someone yeah exactly i think one of the things i struggled with a little bit of progression was i sort of was classic first time leader i was like i want to be able to go to the pub with everyone and we're all a team together and uh emphasizing that too much which meant it was too hard for me to then make decisions that weren't in their interest.

52:34Yeah, you're their boss. Moving things along, crazy story. I don't think I've, I mean, I've had my first share of like exit stories. And one of my very, very, very first early interviews was like the craziest exit story, which was, I don't know if you know, Nick Telson-Sillit of Design My Night. And any stories I've heard, and same with Nick here as well, is it was the other way around. it was the deal almost falling through on the buyer's side so it's incredibly rare at least from my vantage point it's incredibly rare that you had the power and that you had this incredible opportunity and how i just can't get over like i'm definitely gonna be processing this after we finish recording because it's like the months and months yeah and then suddenly like i know the same weekend all of all of the things that had not gone our way yeah led you to that moment but i'm also not good at like game theory yeah i'm not i'm not like a little brinksmanship if in that moment i didn't feel like it was a risk to say that i was speaking quite honestly i was thinking practically to blow through a sure thing what am i willing to risk what does it need to be worth and i just i just spoke plainly about that so you know i think if it hadn't been true if we hadn't had a deal I wouldn't have been able to say we've got you know and that is such a lovely virtual that you've got and something else that I've noticed for some really lovely successful founders like they really they have said that as well it's just another observation where they're just like they're just honest they're straight and it can be very refreshing in this field so moving along we have to cover the post-exit founder existential crisis so here you are you've been through trials and tribulations you've learned so many lessons along the way you've fundraised you've led the business through a pandemic you've hired this team you've grown you've taken it through this adventurous acquisition process obviously you've got your transition and your earn out but post that moment how are you feeling what's going through your mind yeah so I knew from other people telling me that after you've poured everything into something for a long period of time there is a sense of loss after you no longer do it and I didn't feel an enormous sense of loss about not working on progression anymore I think it was the right time but I did feel purposeless in quite a in a way that garnered me I think very little empathy from my loved ones I had I basically had made enough money to not have to work for a bit I had all of these projects and hobbies and things that I was doing instead of working I'd go to the pub with my friends and they'd be like so what are you up to and I'd be like not much and they'd be like what you know um and I reckon and there there would have been times in the past where I'd have thought how blissful that would be right and yet I think loss of purpose is like a really uh insidious thing you feel rudderless yeah and and and I think also just not like you can really explain it to anyone or tell anyone about it in a way that it would make sense because you can't even really explain it yourself like on paper it doesn't make sense so I took yeah I took up hobbies like I you know um built an enormous amount of stuff with AI like just you know any spare moment um worked on the garden and did some DIY and all the things that you do and ultimately was constantly in my head throughout all of this spinning my wheels I'm like do I do it again do I do it again if so what if so what who with who with all of this stuff um and the only reason i can say this it's now been where it was september we sold so let's call it 18 months since sold the business and 14 months since i stopped working for the business was only a four month um earn out which is really short yeah actually and a lot of entrepreneurs will be like and then i worked there for two years by the time i was able to leave i had my next idea anyway so it's a seamless transition yeah and that purpose is like you've got a sense of purpose because you're an employee for a little while um anyway uh so yeah 14 months i would say only since the beginning of this year have i started to be like oh hold on i think i sort of have a sense of what's next exciting so it's like a whole year of trying stuff trying like in december i launched a coffee brand oh i didn't know that a lot of my family were like what what's it called uh buzz cut it's yeah it's half-calf coffee okay cool so um yeah buzzcutcoffee.com if anyone wants to buy some half-calf yeah sorry um you got a code for my listeners come on if you're gonna plug it i don't i'll make one we'll put it in the show entrepreneurs need caffeinating as well um but all of this was like me trying stuff like what about this what about this what gives me energy and um just trying to be really honest with myself and let things go if they weren't working for me even if i'd launched them and told people about them if they were no longer working for me let them go again ai is at the center of of what i have been thinking about i mean progression started using ai and chat gpt3 before chat gpt we built ai features so we've been i've been using ai for for a long time um and helping other people to work out how to use it i became convinced that there's this gap between a few months ago this gap between what's what the capabilities are and what adoption looks like and that gap is fear and distrust and um and to an extent an application layer so like you need the uis to be able to interact with the thing but actually much more good old-fashioned change management and you know in a team what we scared about what tools do we actually need what are we what do we hold close to ourselves that we don't want to let go and what are we willing to let go these are complex conversations that involve people's emotions and so anyway that has formed the center of a lot of my work uh over the last few months i'm working with a guy called tom tom harman also a designer uh and we're running um a sort of boutique ai consultancy uh called near future nice name it is a nice name yeah i love it it's actually not live yet so but hopefully by the time this goes out it will be well this is the deadline it's got to be ready exactly could this be done in a day johnny uh probably could to be honest yeah yeah exactly thank you ouch yeah good call back um so and then alongside that i'm like just fascinated by the design process and how the tools of drawing rectangles on canvases which i've had to do for my entire career are crumbling and now we can start to question how design works very practically inside an organization which is both maybe a niche topic but also will affect an enormous number of people and how the tools we all use every day feel so yeah yeah it truly is disruptive it truly is like having this transformative impact across disciplines across sectors across industries so just like you were well positioned b2b sass in 2019 here you are 2026 ai just yeah i just ride the vibe that's all i do that is that is a legitimate entrepreneurial skill though don't you think of like I think another one of these famous founders also said something along the lines of you know you had that great quote before about you know entrepreneurship being a puzzle but there was another one which was like you're on a beach if you've ever surfed and you're just like there watching the waves and like waiting what's the wave I'm gonna catch because again to my earlier question on how much the market you attribute to the success of progression like you've got to be and that again is where that common trap of like the market doesn't give a crap about your idea it doesn't it's right time right place so it makes sense the the waves thing is a good analogy in the sense that the person that stands on the beach waiting for the right wave will never surf and the person that is in there surfing every wave that was being cringe about um like buying jpegs on the internet three years ago and is now into ai you know they're cringe uh but probably they're in the arena and they'll find something so there's a great quote which is everything you want is the other side of cringe yeah and i think that that is also true you have to put yourself out there you have to try stuff you have to be unafraid of what you're doing looking silly yeah yeah yeah yeah and my regular listeners i apologize because you're really sick of me saying this but the spotlight effect is so real it's a psychological phenomenon where ultimately no one gives a shit no one cares no one's paying as much attention to you as you are you were all walking around with the spotlight effect yeah everyone's just getting on with their lives completely if if your if your linkedin post doesn't pop no one noticed by definition so it's right literally it's like bad news no one saw it good news no one saw it you know johnny oh my goodness thank you so much for coming on the show I feel like this has just been like collapsing your wisdom and your entire career, including your entrepreneurial journey into just an hour nutshell here on a podcast.

1:02:29I would love so badly to like go deeper on each of these subjects, but it needs to keep things moving along. Johnny, anything else you'd like to share before I come to my traditional closing question? Oh, no, I know what this closing question is going to be. And I feel like I don't have a good, I'm not sure I have a good answer to it. So you now may be nervous. um and anything else i want to say no everyone should uh keep an open mind and avoid being too uh committed to any one opinion at any one time especially at the moment that's deep and i'm gonna leave that there on technology i'm not gonna double click on that one okay let's see that there johnny my show is called strategy and tragedy because often the best lessons come from the biggest mistakes aka tragedies what's one tragedy that's taught you an unforgettable lesson the first time i had to let someone go at progression i had been thinking about it for a month two months and i had been thinking is it them is it me am i being really bad at managing them we're not getting on very well and the work isn't great but i'm not sure what's going on it might be me and i talked to another founder who gave me a really good bit of advice or he just laid something out which was obvious in hindsight which is it doesn't matter like you can go to the ends of the earth thinking is it you or is it them should you change should they change ultimately you're lashed to the mast you can't fire yourself from this company so if it's not working they have to go and I'd had that conversation on like the Wednesday with this guy so I was like okay that was useful we're going to make the decision so I'd line myself up to have a difficult conversation on the Friday and then on Thursday my wife went into labor wow plot twist um and um so I was gone I mean I was you know doing more important things I had to ask my co-founder to do the deed and I felt so sad and ashamed that I had taken all this time and finally got to the point where I drummed up the courage and then I didn't even do it that sat with me and I think it just goes back to being decisive I mean I couldn't have planned for the the labor obviously um i actually also signed a term sheet for our second funding round holding my nine hour old son that was a single piece of admin that i did really need to do wow so i was on docusign in one hand um holding my son in the other wow didn't go down super well but i was like i'm sorry i'm here but i know i just need to do this one thing um so i didn't read the docs particularly closely but it's fine in the end um anyway uh just being decisive and not letting things linger would have been better for everyone especially me in that moment but um just yeah i mean it sounds like you've had a lot of other stories about these kind of hard decisions that involve humans and not wanting to do anyone a disservice you know it might have been our culture it might have been some other reason um this is a good person so but getting all in you know second guessing yourself all around in a circle ultimately if it's not working just not the best thing to do for everyone yeah um is make a decision yeah so yeah i suppose that is yeah it's not a tragedy but it's a little bit dramatic over here no that's a great lesson shared johnny thank you so much for coming on for sharing your stories of eating contests of fundraising amidst a pandemic oh so many other fantastic pearls of wisdom that you've shared so thank you so much thank you for having me it's been great and thank you so much for tuning in if you've enjoyed this and you haven't already please hit that follow subscribe button give us a thumbs up share a comment share this with a friend and episodes are weekly so hopefully see you next time thanks a lot bye bye so you always kind of i'm gonna start that again it's like the least smooth transition i think i'm so put off by you being high Mine was lame as well.

1:07:08This is so funny. Shall I start with a less weird greeting? I just don't think any guest has responded to me like that before. Hi. Hi there. Right. Hi, great to meet you. This is just corpsing now for an hour, isn't it? Oh, my cheeks. Okay. We're good. Hi. I don't know what to say that's different. I don't know if I got started. All right, don't worry. Let me just start with the question. It's all good. Oh, my God, my face. Okay, I need a second. Okay, I'll just do it. Hold on. I'll go. Hi, great to be here. No, it's not going to work, is it? Sorry, the classic is. What do people say? How do humans talk?

1:07:59I make sounds with my mouth.

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