How do you know it's time to quit? 7 founders on life-changing career pivots

There's some part of you that goes when I'm no longer the CEO on debt, like that's my identity. And I sort of asked myself the brutal question, it's like, does my presence here change the trajectory in the answer? It was like no. Because it was like my baby in some sense, yeah. And he was like, "Hey, this could be a generational company. You should be thinking hard about this." One of my best friends in the world challenging me to say, "Get in the game. Get off the bench and get in the game." When I rang Robin Danholman, said I wanted to step down, she said, "You realise you cannot come back." And I said, "Yeah, I know. I'm happy. I'm done with time. It's fine." The most tragic companies aren't the ones that fail fast. They're the ones that succeed just enough to trap talented founders for years, making enough progress to stay alive, but never achieving escape velocity. We're approaching the end of the year when people reflect and look ahead. So to honour where your head might be at, we decided to revisit moments from seven different episodes where founders made life-changing career pivots. Now to fess up, I have a particular personal interest in this topic, having made the decision to step back from the company that I co-founded applied a few years ago. I remember it as being an agonising call to make, and I've always been curious how others have navigated their own versions of change. In particular, how they square the decision with their own identity, which has often become inextricably linked to the company itself. Every founder in this episode made a life-changing decision to stop what they were doing and make a change, whether it was a founder leaving the CEO role, selling their business, making a major business pivot, or walking away and completely changing the industry they were working in. This is a new format for us at Wild Hearts, and we would love to know what you think of it. We've got over 100 episodes in the archive, so if people enjoy the format, we have a large body of content to potentially dig into. So let's get started. Did EA co-founded Culture Amp, which was in Blackbird's very first fund, and was it CEO for about 15 years? Earlier this year, he handed the CEO role to his COO, Caroline Rollinson, or Carro, and became its executive chair. In this clip, you'll hear him reflect on when the job has come, who you are. How do you know when it's time to hand over? You were at the helm of Cotchamp for 15 odd years. The decision to step back a CEO, talked me through what was behind that call and how you made it. I think it's a difficult thing for any founder to go through, because you're like in some way, a some part of you that goes when I'm no longer the CEO on debt. That's my identity. I had actually gone through in my own personal work, people asked, "What's the questions that you're grappling with? What's the deep work that you're doing?" One of the questions I've been asking myself for the last year, maybe year and a half, is how do I disentangle my own personal identity from the identity of the company that I found it? Because for me, they're synonymous. It was doubly so because I was a CEO in my previous company too. I've been a CEO for five years at Rising Some Pictures and then founded Culture Amp and so on. I've been a CEO for 20 years. Who am I when I'm no longer the CEO? I'm still trying to figure that out. That process of thinking about it, trying to figure out when's the right time. It's like little seeds, I think. Several years before, probably four or five years ago, I was at a Morgan Stanley conference and I had the benefit of hearing Jim Donohoe, Bill McDermott and Brad Smith. Jim Donohoe at the time was the CEO of ServiceNow and then he went on to run Nike. Bill McDermott was then the CEO of SAP and he went on to run ServiceNow and Brad Smith was the had been the CEO into it and they were all the third or the fourth or the fifth CEOs in those companies. It was actually really interesting to look at it because I remember thinking I can't conceive of the world when I'm no longer the CEO but then you see these incredible leaders who've inherited from somebody else and you realize them talking about legacy that if you're going to build anything enduring, it has to outlive you and so it's really interesting and it actually made it into this painted picture that we wrote a culture where I had a line where I was talking about the future and I said I think my successor's successor has just joined the company and it was just getting me to start thinking about like at some point I'm going to hand over what does that look like. It's beautiful. I mean we were both in San Francisco a few weeks ago and I think we got into a conversation about what is permanence in this world, this sort of huge juxtaposition I think we've got right now which is that AI and the technological revolution behind AI is changing faster than we have like arguably the psychology to be able to internalize but at the same time you mentioned sort of legacy and out living you know a company out living an individual and some of the best companies in the world have done that many times over. I'd love your perspective on how you think about permanence and how like your association with culture amp has changed as a result of that. Oh such a deep question. I had the fortune I had an executive coach who was Steve Jobs' executive coach. Wow. I'd always struggled I've had a few coaches but I found them a bit too reflective so they're just passive in a way and I'm very good on my feet and so what would happen is they'd ask me a question about something and then I'd answer it and then they'd let me get away and I'm like no no no no you got to push me harder than that because I didn't actually I said enough to not have to answer the question properly. Be better I'm bullshitting you. Yeah exactly exactly but one of the questions that we used to keep coming back to is what am I trying to prove to him. I think part of what made this a good time to step down to CEO and take on the exact chair role is I'm still working two days working culture amp it allows me to be there to focus a support I obviously to support Cara and help her she's the first time CEO she's incredible she's been in the company for a year and so I got to know her knew what she was capable of and I'm really excited to have her in the role work with Chris on the product but more than anything it allows me to go deep on AI because I think we are in this window right now where the world's changing at an exponential rate and I didn't realize it until after I stepped out but having stepped out and then starting to spend three days a week just reading coding listening talking learning I don't know how anybody who's got a full-time job can keep up with what is going on and so I couldn't have picked a better time because the problems that I'm fascinated by even the problems the culture amp was set out to exist to create a better world of work are deeply deeply impacted by what's happening on an AI and by being the exact chair I can actually do more of that than I could as the CEO which is also a humbling thought. In October 2025 my colleague Maddie Gess spoke with Michelle Battersby. Michelle co-founded Sunroom a creator platform for women and non-binary people with Lucy Moore and spent five years building it. As you'll hear in this clip making the decision to sell her company was a very difficult one for them both. Sunroom was acquired and Michelle has since become president of peanut a social platform for women focused on fertility pregnancy and motherhood. What stood out in this conversation was the central dilemma when the business is working but just not well enough to achieve escape velocity how do you know that it's time to call it quits. You have said before that Sunroom is a business that objectively works but that never quite reached escape velocity what do you mean by that? Yeah it's something that Lucy and I have spoken about and I think we overestimated the size of what this market could have been it ended up being much more niche than we could have predicted and that still helped us build an incredible business like we raised money three times we could grow up until a certain point and then it felt like we had almost maxed out of our category and this is something that we've seen happen to other platforms in our space as well like there was another competitor of ours called fan house and they attracted a whole bunch of gamers and then it was like they couldn't quite get beyond that and maybe it's because that's what they became known for and so it's a really interesting place it's kind of a hard place to get to with the business because you have all these early signs of success and all this amazing early growth where you're growing month on month you know at a pretty good rate and then it stopped in our case like we kind of just got to this level where it was really quite flat and we kept trying to break out of this pocket that we had discovered but nothing we were doing was working and it was very frustrating from my perspective because I'd be sitting there thinking you know if I could get all these women and they can achieve X why can't I just go get a thousand more you know like if they could make it work why can't all these other people like Lucy and I so many of so many times we would kind of get to this point of thinking you know maybe this is it but then we'd be like but it can't be it because we did this and I still haven't really worked through those thoughts yet I will truly believe we left no stone unturned like there was absolutely nothing more we could have tried do you want me to read the LinkedIn post yeah okay we're talking about context we were talking about a LinkedIn post that was really good before we got a mark so yeah okay so this LinkedIn post says the most tragic companies aren't the ones that fail fast they're the ones that succeed just enough to trap talented founders for years making enough progress to stay. alive but never achieving escape velocity. And it hits pretty heavy. Yeah it does and I'd never really been able to describe how it felt and to your point and like Lucy and I spoke, we've spoken about that LinkedIn post so many times and like reminded each other of it because we were both like oh you know trap talented founders for years and how previously I was talking about that very frustrating feeling of like if all these women over here are doing it why can't we just go get a thousand more you know and that is kind of like what comes up when I when I read that because I would often think would it how would it have felt if this just never worked at all you know like if we raised money and it failed within a year and we had absolutely no success what would that feel like compared to what we ended up going through well I kind of came to the conclusion that even being trapped for years quite on quite like I just kind of look at this outcome now and where I'm able to take my career next and I'm like God it was so worth it like it was so worth the struggle and it was it was really hard like Sunroom was hard the entire time like it was a grind to grow and those like you know eight back-to-back creator calls a day like constantly searching for these people that would find success on our platform and I relate to that you know I relate to I think she says the most tragic companies and it's weird and like I don't know if I should admit that this but it it does like really kind of yeah like it really resonates and for me to say it really resonates but for me to say I'm so happy and grateful and glad I had the experience I think maybe says a lot that even though it was really hard it was it was so worth it and I definitely do it again and I would you know put myself through the same sacrifices over and over and even though and I guess you know we're also talking about Sunroom from the perspective that I think it would have felt very different if we didn't raise capital and we weren't looking at all of our achievements on a venture scale that's also the weird thing that I've been toying with is like this was a successful business that made loads of money but it didn't reach that venture scale so you do feel like oh we didn't achieve what we set up to achieve yeah so it kind of like messes with your sense of pride perhaps because we did have much bigger we thought we could take it so much further we thought it could be an only fans competitive we thought it could be you know it's like you're a you're a creator you're an Instagram you're on TikTok you've got a link tree you've got a sunroom you know we kind of thought it could be that piece of a creator's ecosystem of the the platforms that they use and so there's that side that's like oh we couldn't do it but then there's the other side but it's like that's like but we did it for so many women you know and so many we had creators earning like half a million dollars on sunroom we had creators quitting their jobs putting themselves through college paying their rent their car insurance we had messages all the time like this product means so much to me and in the aftermath of selling it like we've had creators cry to us about how sad they are to see it go and that's really meaningful so this is why I'm in I'm in a very torn yeah I feel a whole range of different things about it in July 2026 I spoke with Mick Lubingskis Mick had spent more than 20 years in Australian tech he led global marketing at Kazaar co-founded Polynesia and Muraday and was there at the start of start meet in 2017 living in the US working on Muraday and approaching 50 he got a one line email from an old basketball teammate that pulled him into climate tech he went on to start climate salad now community of about 800 climate tech companies the change Mick let's us in on was all about how he didn't get daunted by starting again in a whole new field mid career you've hitched your considerable brain and energy behind the climate challenge and it's challenged that you know is so big so contestable that you'd be in human if there weren't occasional times when you didn't want to throw in the towel every now and then I'd love to know why you chose climate I would have considered most of always someone who I think if you asked me before 2016 I would have said yeah I really care about the environment and I do as much as I can and probably more than most you know kind of I'm doing it above average in that area and then I actually moved to the US with the Muraday program and was living in the US and the US appointed a brand new president and in 2017 like first day pulled out of the power of agreement and in terms of the thousand really lucky privileged things that have happened in my life one of them is I met a guy who was playing basketball with as a teenager named Nathan Fabian and he ended up quitting his big corporate job and going to do international relations about 20 years ago and started working in sustainable finance well well well in advance so if I feel like I'm a veteran in nine years there are people like Nathan has been doing a long time anyway I messaged Nathan and we used to play state league basketball together and I said hey this really sucks your job just got harder that was my dig dig back at him and and he said yeah maybe it's time you got in the game and that was it it was like a one-line email and I'm like in the game what do you talk about like I'm a geeky nerd what am I supposed to do he's like we need 10,000 innovations to get back to sustainability and he just attached the recent IPCC reports famously a great nighttime read those IPCC reports such such good nighttime reads so you know I open up the big full report and then I closed open up the summary and then I closed that and I open up the executive summary and then I was just reading through and it I think the combination of factors like it came in a time I'd move to the US and given up lots of my board seats in Australia a lot of my community roles I just had this space in my life my kids at the time was sort of two four and six so I was I was just like this new dad being a parent I was also approaching 50 years of age and I was like okay I've spent since eight years old in technology this incredible combination of like I'm a little bit bored I'm a little bit midlife crisis II don't quite want to buy a red sports car and here is this really you know one of my best friends in the world challenging me to say get get in the game get off the bench and get in the game because we need 10,000 innovations and I'm like this is a whole new area this is science and deep tech and this is really hard and it's actually policy and it's complex and there's billions of negative of dollars and going negative against it and and partly it was kind of like I felt like I had to do it because I've got my kids and you know the day before I would have said I'm going to leave the world in a better place I'm working my butt off I'm going to give them good education good home good lot to love and like that's going to be great and then I read this reports and I'm like maybe I'm not maybe maybe I'm not and maybe I do all those things and the world sucks because we couldn't get our act together and get back to sustainability and then you look into it and we hit negative sustainability like we started consuming more resources than the earth can naturally replenish between 1979 and 1975 like when I was born so I'm kind of like this is in my lifetime this is in my lifetime this has happened if any if I back myself at all as someone who has capability and influence and the entrepreneurial talent to just start things get things done and this is a big challenge and I want to work for another 20 years of my life and I want to leave the world in a better place for my kids like for me there was no other choice there was there was really really no other choice the only thing after that which I'm really really fortunate is that I'm massively driven by wanting change in my life so for me it was kind of like it was 99% unknown and that was like a really good thing I really wanted it and it was high purpose and it was going to get me busy and it was going to be great for my kids it like ticked all the boxes and I wanted the challenge and then I just got started Charlie Gearside co-founded Eucalyptus or Yuc the consumer health company behind pilot and Jupiter as creative director he made the ads for products where there's a stigma about talking about health especially the less comfortable elements of it he left at the end of 2024 and Eucalyptus is $1.6 billion exit came after he'd gone he spent about a year working out what to do next and he set up a YouTube channel about Australian ambition and build Australia which he helped to launch I spoke to him just before that launch in this episode we released a few months ago Charlie talks candidly about knowing when the company knows longer needs you and what it looks like to rebuild who you are after it. You left you because I found a end of 2014, 2024 I should say and you know as I said earlier this year February the sort of exit happened. Can you tell us a little bit about the decision to leave? I'm sure it was a hugely emotional one that you took at the time you said the company is moving into a quote more stable place which you know for a guy who's who lives in stigma feels a bit like PR speak for like I love the 0 to 1 and it's gotten a bit big for me. Can you share a little bit more? It was PR speak. It's definitely a case of me sort of realising as I get older that I'm built for I'm wide for building and not managing. In fact I'd say that I've been slow to get up the curve as a manager definitely getting better at it every day but you grew at such a rate that I sort of like looked around the company was several hundred people. I looked around this sort of border of environment and realised that there was many more capable people than me and I sort of asked myself the brutal questions like does my presence here change the trajectory of equipments with team and the execs and the broader team and the answer was like no. It takes a degree of self-awareness to like even want to ask yourself that question let alone be open to what answer comes from it. Have you always been capable of asking yourself those hard questions? Is that in Denmark and you? I don't know. I think there was an extremely painful period because like you tie your identity to a start-up and that's a feature not a bug and then eventually like you work so hard and then eventually when it comes comes time to pay that toll. The unpicking of your identity from the company is hard. When did you learn for anybody who might go through it? I think it's surprised to everyone but if you're feeling stuck movement and forward motion is the best often the best antidote and a lot of people I think it's enter and analytical phase and introspective phase but honestly sometimes you sort of just have to like exit a situation. There's a world where I've stayed at equipters but I definitely think that for both equipters and myself there's a lot more. I've really enjoyed this period and would have helped me with what I actually made that that first step you know. What is the mission? Like what is Charlie Gearside's like you know motivating mission post-Uk? I suppose to explain how I got there. I've actually as you said I've had sort of 12 months after I left equipters to actually think about things. I wanted to spend more time with my young boy and my wife which I'm you know I needed to spend some time there and in that sort of creative wandering period so to speak I realize a couple things. One that I enjoy work I'm not I'm not someone that wants to sort of lie on a beach that kind of thing and then I guess two was that once you do a health care startup a consumer health care startup your standard for like a mission needing a mission to sort of get you out of bed every morning becomes a prerequisite. Was that new for you like do you think that came because of you or was that always a part of what you were looking for? I think it's it's almost like the hierarchy needs like I think first you want to sort of get your family in a and a good enough position financially. I think everyone should be honest and open to that I certainly am and then now that you've sort of earned the right to do anything what what are the important things and so full respect to be to be sourced but I'm not gonna go and do a bit of a sourced right that's not gonna get me out of bed so I was on this journey of thinking like what are the things that are concerning me I sort of I've had kids now I can see where Australia is heading you know Australia sort of comfortable with an economic decline you can talk about the details of that later but but the specific part I felt like I could start to make an impact in and I was most concerned about was the media and and how modern post internet media is is a something that everyone consumes but it's it puts people in this sort of heightened emotional state we're consuming headlines we're being cast against each other a lot of the news that we consume both traditional and in social media is extremely negative you've got a situation where politicians fixate on what the media is going to say what they might say and none of this is really good for Australia and so from there I was like okay is there an opportunity to do something in media I certainly believe for Australia get better we need ambitious stories we need optimistic stories positive stories that we're just not getting there's no incentive for the media to really tell those stories I used to use the right to blog years and years ago and I wanted to get back into writing but I just think I mean sub-saxx are having a moment but in tech circles and I was like what so many people were just consuming video you know I'm not a huge tick tock or Instagram real sky so now I was like you know what I really like YouTube I can do my writing and then essentially turn to a camera and deliver it deliver that idea and so I sort of just started there knowing that it was going to be like the first video is going to be super uncomfortable and there was a lot of like fobias to get over yeah say more because I mean like the irony is like you you had this sort of career of like destigmatization and like you know you would have chosen loads of models and design loads of ads to have people be in the hot seat of like the awkward thing and now it's you yeah what what was that like yeah that was the scariest thing I've done in a while it's like you can hide behind a brand yeah but when it's you sort of you are the brand you are the brand and you but I'm getting more comfortable with the idea that like like I'm trying to be myself and then in a lot of ways it's very liberating to align your sort of things that you post from your person and I find it interesting that like in the future when there's so much like AI content and this you know it's like the humanity of content is actually going to be super important a mode as it were and so like being yourself with all the positives and negatives that brings the all the water and all is kind of appealing and important now is canvas first chief algorithms officer before that he's been about a decade at Netflix where his team's data science informed what the company made and how it marketed it and he later became CTO of the reading app Fable he left all of that behind to co-found mango AI and AI marketing start up with his friend and former Netflix colleague beneath not long after they launched their website canvas co-founder Cliff Obrecht approached them just as they were about to raise canva has since gone on to acquire mango AI the first section of this snippet is about where he left the comforts of executive life to founder company and the second is about the hard call to set founding aside for the opportunity to sell his company into one of the world's most ubiquitous platforms to big changes and to great reflections your co-founder was when he's who you first hired at Netflix when I chatted to him in advance of chatting to you he sort of said this interesting thing where he felt that the two of you explicitly or implicitly had always danced around this idea of like I'd be fun to found something at some time you know so I'm really interested in like you know by this point you were a storied you know machine learning leader you know c-suite all that sort of jazz what gave you the reason to leave like what was the reason to say now is the time we're gonna have a crack at founding a company yeah I mean I've always been interested in startups because you know I after Intel I was like let's go prior to startup and went to the health tech startup and so on so I think there's definitely a thread there in terms of like the excitement of a startup the excitement of you know doing something new and it's always very impactful you know in terms of startup right and so that was definitely there and yeah even after you know I left Netflix and we need left Netflix we stayed in touch and once in a while you know we'd get together to play tennis and you know start talking about startups and so forth so that was definitely there I think for me the thing that really helped was you know I've sort of over time I suppose as I'm getting older adopted more of a regret minimization framework so you know I think the idea is like you don't want to sort of 10 20 years down the line sort of feel like oh I should have probably done that right and like that's kind of a lens that you can use and we should have this leadership seminar at Netflix they still run it which is you know less about like leadership training it's more about like how do you think of yourself as a leader in the world and how do you think of yourself as a human in the world and so forth and you know you're reading like very deep stuff like your 12-story and you know Dr. King's like letter from the jail and all those kinds of things and having very deep conversations and one of those topics one of the questions they ask is what would your like 80-year-old self tell you now right and what would you tell your 19-year-old self now right and so we're all like you know sort of mid to late stage career if you will at that point and it's a very interesting reflection question right and so you apply that and that sort of a lens I try to apply more and like I would definitely regret not having founded a company you know 30 years down the line. And so that was definitely definitely part of it. And then I think this confluence of the tools coming together and, you know, just the sort of time that we're in, that felt like a good time to actually, you know, try something new. What was being a little bit more later stage in terms of like, you know, we're not fresh grads out of college trying to do something. I think definitely gave us a little bit of a cushion and, you know, financially as well as like, we have contacts, right, so we could go and approach people for trying to do a B2B thing. You can get pilots and so on and so forth. So we had the network in some sense to go try something and both of us were very much like, let's go do it. Let's see what happens. And, you know, it's either way we'll learn something and, you know, we're not fun doing it together. And so yeah, that's how it happened. Well, you've had an unusual journey since then because it was sort of, you know, sooner did you like create the website and make a public that you had acquisition opportunities coming at you. And obviously you've just joined the Canva universe as one of the sort of recent acquisitions into Canva and its AI push. I'd love to know a couple of things. The first one is like, for someone who spent all of this time thinking at founding a company as a thing that I would love to have done. Did you feel like you got far enough in or was there any part of you that was like, oh, not yet, you know, it was so fast because people were so excited to think about the opportunity of bringing you in to Canva and I'm sure there were many other conversations that were happening in the background too. Yeah, it's, you know, definitely something that we still talk about. It's, you know, was it too soon, but- Because what was it? It's 18 months each, right? Yeah, by the time. And it was tricky for us because we were about to raise money. The thing that I would say we were very good at is, you know, actually hiring and, you know, getting strong talent and so on and so forth and, you know, done that in the past as well. And so we still, we still talk about it is like, we actually kind of got to that fun part, you know, we almost got to the fun part and like, you know, really good stuff and we kind of didn't get to do it. But, yeah, we were- there's also another aspect there, which is we were about to raise money and, you know, we had some friendly VCs. We were doing demos too and one of the first demos actually, very well known we see in the space. We had a really huge exit and, you know, a few years ago and so on. I don't know, 20 minutes in. He was like, "Hey guys, I want to fund you." You know, he was what we were doing. Like, tomorrow, you're here's the deal. And I was like, "Oh, I've been out ready for this." And, you know, and then at the same time, is when like the camera discussion started. And as you know, this person would have wanted to give you even more money even faster after you were like, "Thanks, but no thanks." Yeah, so, I mean, that was, he was- he was a good sounding board, if you will. You should really think hard about this." And, you know, like, we'll help you find other investors. Like, we can do this very quickly. So, it was a- it was an interesting time because we were definitely at that point where you know, we knew we could actually raise money and we knew we could go at this very hard. And the other hand, you have Canva here. And so, yeah, it was a- it was an interesting time and tough decision. What nailed it for you? Why- why path A not path B? I think, you know, a few things, I think Cliff was definitely very hard to say no to. It is a unique skill of his. Yeah, unique skill is a great founder, I think. But and for us, you know, we're both very impact- driven people. And, you know, we looked at the trajectory and we're like, "Yeah, we could build this out, but it's going to take us some time to actually have the kind of lot-scale impact that we want to have." And Canva was right there in terms of like very aligned, you know, in terms of what they wanted to do. They already have sort of massive use of base and trying to expand more than B2B. And so, like, impact wise, this would be, you know, much higher impact, much sooner. And so, that was definitely a factor. I think the other thing was definitely- the team we talked to, you know, everybody was great. And I think the mission of the company, you know, definitely appealed, right? You probably familiar with the two-step plan. You know, they think about, you know, what to do in terms of, like, good for the world, right? That definitely appealed to us as well. And so, like, all this seemed like, you know, a good thing to do. So, yeah, we felt good, I think, doing it. And, yeah, so here we are. Luke started safety culture in 2004 in a garage on the outskirts of Townsville. The company's now known as Midi. After almost two decades at the helm, he stepped back from CEO to executive chair. But about two years later, came back as CEO this year. This clip highlights why he left, why he came back. And what he's doing differently now that he's in the role again. So, you've come back as CEO. Tell us a bit about that. Let's talk about why I left first. Like, I was cooked. I'd been doing the job as CEO, probably not well for a long time, just trying to be all things to everyone. And I just couldn't keep doing it. It had taken too much of a toll on myself and everyone around me. So, I decided, you know, I rang the board up and said, I want to step down. And we already had Kelly Boss coming as president, working out of New York in the US market. And I rang Kelly and said, hey, you know, he'd been a CEO of a $50 billion Blackstone business. Do you want to be CEO? I think you'd be fine. And he said, sure. That's the most Australian offer I've ever heard. Do you want to take my business? Yeah. And so, you know, I moved to exact chair and work with Kelly. And look, I'd no one could see, I guess, the AI, you know, bond that was coming, there'd be dropped on everybody. And I think with all our product built in Australia still, and Kelly and his family based in New York. And it was never part of deal that he was to move to Australia. And we both understood that. So, he gave it a really good run. But it was pretty clear that we had to come back. And I had to rebuild the company essentially because I think the way we build now with AI is very different to how we did a year ago. And the opportunities bigger. So it made sense. So, you know, when I rang Robin Danholman and said, I wanted to step down. She said, you realize you cannot come back. And I said, yeah, I know. I'm happy. I'm done with time. It's fine. And then, you know, when we're chatting, she's like, hey, Luke, would you like to come back? You need to come back. And then, and then I'm like, you said that I couldn't come back. She's like, yeah, no, but this is, this is different to come back. So it's been great. It's been the best time in my career to build product. We can actually now build. And I've had this 10 year road map in my head. And for so long, it's been such a frustrating process to try and get it built out because it's too big. It's too hard. We've got three businesses in one. We've got insurance. We've got software. We have consumables and hardware. So, you know, that was my main frustration for probably the last decade. And now, just speed of deployment. Yeah, trying to, trying to solve these problems for our customers. And, and now we can actually get out of our own way and we can build the things that our customers want us to build. And we went from a generic platform where we didn't solve any one problem 100% well. People would adapt what we gave them to suit their business. To now, we could actually build vertical solutions where we can go all the way into quick service restaurants. And now we handle their inventory and their recipe ingredients. And we can tell you that three grams of mayonnaise goes on a burger and four grams of pickles. And when they sell it, that has to come off their inventory. We never did this sort of stuff before. And now we can, and we are. So it's an awesome time to be building product. Yeah, you can hear it in your voice. I mean, you sort of described like you were pretty burnt out. That was one of the reasons to leave. Like the kind of energy shift to like having this injection of energy as it were, it must be pretty fun. Like how do you feel about the role coming back in? Are you doing it differently? Very much so. I think the first thing is having the headspace to think and be creative again rather than being reactive. You know, as CEO, you have a million things coming to you. If you allow your job to be set up that way, which is what I've done. And I think having the headspace to be able to think deeply again about problems, about what I care about, what I think matters in the world, what I think could be better. That's a really valuable ability, I guess, or privilege. And when I came back, I thought, okay, I don't want to allow myself to get distracted with the day-to-day. I want to stay focused on solving the problems for our customers. And so, you know, I'm not in our exact meetings each week. You know, hey, Michelle, see how overruns those, and they pull me in as needed. But I run product, it runs strategy, I'm focused on that, and I work with our customers and our teams to be able to deliver it. So, it's very different. I think you look at, you know, I've seen the way Mel and Clifford Camber have done it for years. Mel has been, I guess, shielded in a way from a lot of the day-to-day stuff. So she could just focus on product and dream up the next version of Camber. And I think there's a really good example in Camber on how to do that. If you have a good partner, she had Cliff as a co-founder and husband. But I think I've had to figure out how to build that in the team and develop that. So, as a single founder, you know, there's benefits, I guess. You don't have a co-founder that you're arguing with, but the business managers, you don't have a co-founder you're arguing with, and that can help you. So, I think structuring it now to have, you know, a team that are able to take care of a lot of the day-to-day allows me to have the headspace to think about the big problems that we need to be solving. Delaney is co-founder and CEO of Anon, an AI assistant for busy parents. Blackbird first backed Delaney and her co-founder Mario for a different product, Brad, which was an AI agent to take project management off-soft for teams. A product very close to Delaney's heart. In this clip, you'll hear her not only discuss her decision to abandon her career as a physicist and instead work in tech, but also the moment that she realized that the first startup idea, Brad, was not going to work out. Painful as you can tell that call was, Delaney then goes on to share how they applied an experimentation mindset. It's ultimately opened up a whole new product and a new market and it might go on to being absolutely the best founded decision she's ever made. So you have a PhD from Harvard in physics and worked on a niche part of the Large Hadron Collider. Talk to us a little bit about what all of that look like with the Delaney of then have anticipated the Delaney of now and what translates like what about being a PhD level physicist has helped you become a product designer and a founder. It's funny because I met my husband on the first day of uni so I was like 17 and all I wanted to do was do theoretical physics and be a professor. And then he's like what happened to you? False advertising. Yes exactly. I think it's honestly like I'm probably an extreme example of like the reality of careers today which is like you just have so many opportunities and you don't even know about when you're 17. I was definitely not on the age you but I think you know and this was two years ago which it wasn't. Didn't exist. Didn't exist. I think the common I don't know what the common theme is other than like I like to work on very difficult problems and like I don't know I just like thrive off or feel happy when I'm like constantly challenged and probably feel a little bit stressed. I don't know if that's healthy but like my husband says you just like to play life on hard mode all the time. I think that's a compliment. I think that's a compliment but I think it stresses him out watching me sometimes but I think it's just like I like to solve hard problems and I like to think about problems that haven't been solved before which is what physics is like very first principle thinking and that's somehow I think how I ended up after even after in product management for so long wanting to a start up just like I when I'm thinking about something I have not done before it's just very exciting to me. I think that's the theme honestly and the everything in between is when I was doing uni here I want to be physicist and I didn't feel like there were that many other options and when I went and did when I went to Cambridge during PhD I was like my god all these people like building stuff and doing stuff what is the start up and that's when I really discovered tech and I was like this moves way faster than physics like it took me takes like a year and a half to write a paper right right one paper yeah and like five people read it and I'm like it's not where I and sometimes those five people are not even on their like Nobel Prize laureate list so you know it's not even like you can yeah a lot of phenomenal researchers out there expanding enormous effort pursuing the sort of intellectual frontier in a way that none of the rest of us appreciate exactly it's like it never makes it and like physics is like one of the oldest so it's like so narrow down and move so slowly and I probably learn something about myself in my early 20s of like I like things that move fast and so like when I went to med I was like okay this is the right pace for me it's like things move fast that was just like a learning I think about myself yeah and so applying like what I'm naturally good at to that pace landed me here I think you went through I think in my time at Blackbird at least one of the most extraordinary periods of what we sometimes refer to as like playing out in the idea maze you tried something like nine or ten ideas before you landed on an iron I really do want to get to anna but I think it'll be great to spend a little bit of time in how you went about the process of saying okay it's not braid got money in the bank great ideas a small crack team that we can do interesting things with where we can go with this like walk me through how did you start even the process of like filtering ideas yeah I mean I mean the first step was just acknowledging that we're going to pivot because I think you can have this like slow death and I think part of my co-founder is a second time founder because he co-founded Spriggy correct yep so Mario was like I don't think we have part of my faith I'm like okay and you're right because it was like my baby in some sense yeah and just being like okay we're going to clean stop we won't let it have a slow burn takes courage to do that I it was super difficult to kind of do it but actually like one of the way things like max was who is the partner we work with that blackboard was like really amazing about it like the first time we had the idea the concept of an idea maze was from him the process was once we had said hey we're going to pause or we're going to stop it was you know the idea is that we're going to have as many turns that having like a bat like the more chances you have the higher your likelihood of like kidding a homerun we had some guardrails around like hey what kind of things are we not good as a team what kind of things do we not want to do but everything else was kind of like game at some point we had like each engineer you go try this thing you go try this thing I'll help you and I'll help you like get it to market or go post on LinkedIn about it like I can I give you the face of it but we had each engineer almost like experimenting and running with an idea one of our engineers Arif actually built out one of the ideas we working on is AEOG of e-commerce which is one of the ones that was very promising because we had a bunch of small businesses who were interested and we had built out this experiment where they would get to the point of almost like paying for it and they'll be like oh send us an email and so we experimented through like 809 different ideas in like a five month period in like a five month period I mean that is the beauty of like where we are today you can build very fast that is mean you can build like a proper full on product but we were thought very carefully about what would what's the experiment that would get the signal that it was worth another two weeks or another month of our time let's get on to Anna so Anna is you know you might say like a sort of AI EA for parents correct and so your kind of pain point is is one shared by many I think take us a little bit into like where did the first idea for Anna come from out of you know you were trying ecom you were trying prompt products you were trying you even did a health care product I think for a little while yes I'm where did Anna come from unexpectedly it was like we were or everything we were trying was like B2B at that point and go go who's one of the engineers he's like a tech lead he built this little agent what's that agent for himself he has a family and he has a lot going on managing like life and work and he's like I use this agent and I'm like I need that and then and then I just like posted about it in a in a Facebook group because that's almost like the first level of like customer validation you can do and then I got such a response I was like hmm okay this is different from like I didn't really have to case customers for this yeah but that signal was so strong it was worth another two weeks of time and that's how it started and there was like two weeks mine two weeks mine two weeks mine here we are I hope you enjoyed hearing these windows into the minds and decision making approaches of some of our ecosystems best founders what they grapple with how they made sense of themselves as people and what it looked like to confront hard calls we'd love to know what you would think of this format leave a review on your podcast platform or reach out to us thank you so much for joining us for another season of wildhards if you want to learn more from other ambitious people building designing and creating the world that we all want to live in then please hit the subscribe and follow button it didn't mean the world to us the founders the operators and the investors who join us on wildhards this podcast is a labor of love from Blackbird team and our production team the show is produced by Joel Connolly of Blackbird a marketing genius is Laura coford and our editor is Andy Jones and I'm Kate Glazbrook.