Would you say no to a million dollars? I mean, imagine if your business was minutes away from securing a huge investment boost, only for the founder to turn it down. What could possibly make someone say no to such a big payday? A nose ring? Doctor Katrina Wallace founded Flamingo AI, which became only the second women led company to list on the ASX. And yep, she turned down one million dollars because of a nose ring. But we'll get to
that soon. Kat also happens to be one of my favorite people in the world and has been my friend and business mentor for over a decade. In this very honest chat, Kat tells me about how she dealt with some incredibly blatant sexism during her time as the founder and CEO of both a private and then publicly listed company, the most important lessons that she has learned about leadership, and we even get into talking about experimentation into psychedelics.
My name is doctor Amantha Imber. I'm an organizational psychologist and the founder of behavioral science consultancy Inventium, and this is how I work a show about how to help you do your best work. If you've met Kat, well maybe you've seen a photo of her, you'll probably have noticed her nose ring. But what you probably didn't know when you saw that nose ring is that it cost Kat one million dollars.
So I was with my female chair and board directors of Flamingo Ai AI company. We've just listed on the ASX as the second ever only woman chairwoman CEO to list on the ASX, so being a woman with a bit of a novelty. We were in Melbourne and we were presenting to a whole room of all male investors and we did a pitch. We did a good pitch, and then we're in the airport lounge on the way flying back to Sydney when one of the investors rang one of our board directors and said we would love
to invest a million dollars into the business. And we overheard that we were very excited about it. And then I could see the blood draining out of my director's face as he was listening to the rest of the call. And the rest of the call was the investor who represented the team of investors giving the conditions by which
they would provide the million dollars. So I heard that there were some good conditions, so I said to the director standing behind him, Oh, look, if it's revenue targets or reducing the cost of customer acquisition or reducing the burn, just let us know what those targets are associated with the million dollar investment. Anyway, you see more blood draining out of the director's face. And he got off the phone and he said to me, right, well, they do
have a condition. And I said, okay, well, you know, revenue profit, what is it? And they said no, the condition is we will invest the one million dollars into the business if the female CEO takes her nose ring out. And we went, what, like what it's a joke, right, and he said, no joke, They're deadly serious. There's a million dollars on the table if you take your nose ring out.
Wow, what did you do? Haha?
I sort of half laughed and cried and then just looked at my chair and said, there's no way we'll take that money and there's no way there's nose rings coming out. And so we I told my director, who was really not too happy, to decline the offer. And then the very next day I went to Gleab Markets and bought a much bigger nose ring and put it in.
Wow. Was there a point where you considered taking your nose ring out?
No, but there was plenty of people it did say to me, look, it's a million dollars. You do more than you do less for a million dollars and take a nose ring out. But for me, what I had already learned having been around the investment fueled for a little while, was it's about the type of investor you get into the business. It's not so much the money
that you get is the type of investor. And if we were starting off with investors who were most concerned about my physical appearance, then that was all going to go downhill after that. So I was wise enough to know this would not be good money into the business.
I know that you experienced a lot of sexist behavior as a female leader of a tech company. What were some of the low points or the low things that happened.
Yeah, So there was a big challenge I believe by the main of the investment community, and this is mainly the capital markets to the public markets, much less so in the venture capital markets. Really challenged to have a woman who is also a mother. So I have five children, so two step sons and three of my own who've
all grown up together. And so I did have investors say to me, can you please tell us how you can possibly run an ASX listed company that's based in Sydney and New York and raised children and I was a single mother at the time. To them, that was all in impossible package. And in fact we had I saw messages on chat groups where people say, oh, we'd really love to invest in this business. However, the founder of the CEO is a woman and a mother, so't
we're not going to invest. So there was definitely that perception that if you not us to a female, but in particular if you're also a mother, let alone a single mother, then there's no way that you could actually be a reasonable CEO.
Wow, what did you do to overcome those perceptions?
Yeah, Well, what I had to start to deal with is not be defensive. So there's a lot of personal work. I had to do a huge amount of personal work because in being in the public eye, everything you do, you say, you look, everything is scrutinized, and then on a thousand chat rooms and in the media and everything. So the first thing was me to just build up internal resilience to just not have these constant criticisms affect me or for me to feel that I had to
be defensive all the time. And my way of doing that was that was my step into deeply working in mindfulness. So having a practice every day of mindfulness, yoga, exercise, I read a lot around mindfulness. So that was a real savior for me as getting resilience to handling the criticism. And then it was really just not to take it personally. You know, I'm there to do a job. It's not personal. Even though it was highly personal, I wouldn't take it personally.
And I also knew I was representing other women and women who were to come after me. If I could help just kind of push through some of those boundaries and those perceptions, then that would be useful. So I was inspired to do it for women other women as well.
So what does your daily practice look like around mindfulness and exercise and yoga.
Yeah, so it's definitely something I try to do every day but do not always manage to do it. So I used I was originally used Sam Harris's mindfulness training here called Waking Up, and I just do that every day. And then I got into a bit of stoicism, so following stoic practices then Cohen's koa n and just started
to bring these practices into my daily life. And so I would spend possibly an hour a day between meditation, some gratitude and reflections, journaling huge thing for me, journaling, and then movement so yoga or running or stretching or something like that. So if I can do that an hour a day, not necessarily an hour together, it really is the foundation for my mental, physical, spiritual, emotional health, and I'm a much better leader as a result of it.
What do you do though, when you just don't feel like it? And I say this from personal experience, Like I've tried to have a mindfulness practice. I'm pretty good with my exercise practice and that's very habitual, but when I've tried doing bouts of mindfulness, it's like there are so many days it's like I can't be bothered. Like, what do you do when you're feeling like that? I mean, it's obviously having great long term benefits, but in the moment, it's not like you feel the benefits instantly.
I'm assuming Yeah, So I would say, don't be bothered if you're not bothered, Like on a day, don't be bothered and don't tach yourself about it. So if it's just not going for you for that day, then just acknowledge and be mindful about Hey, I'd like to meditate today, but I don't feel like it, Like my mind is crazy all over the place. I've got I'm tired, or I'm emotional, or there's too much work. But I'm mindful that right now, I'm not going to sit in my practice.
But what I would like to do is i'd like to do that tomorrow. And so I think you just bring that mindfulness about not being mindful. Don't touch you, just don't touch yourself because the more you pressure yourself, the less likely you are to do it. So there are plenty of days where I wake up and I just go, nope, not feeling it, not feeling it. But I'm conscious I'm not feeling it. Why am I not feeling it? Oh, I've got pressure. Where's that pressure? That
pressure is here? Okay, that might be something I need to look at later today.
I want to come back to the sexism, and I mean in terms of not getting defensive when you are met with these ridiculous comments and perceptions. I get that you've got this almost foundational routine that helps, but what do you do in the moment, because I can imagine it would be so easy to just get defensive and respond kind of impetuously.
Right, yes, so often what I would do. So I'll give you an example. So there was a time when I was doing a presentation to a whole bunch of investors and one of the investors came up to me afterwards, and an older man who said to me, look, I've got some criticism about your presentation. And I said, oh, okay, sure, happy to hear it again. You know, it's the numbers
not quite right, or I'm missing anything. And he said, the dress that you're wearing, it's too sparkly, and I'm my attention was on the dress and I couldn't focus on your presentation, and it was like gold smacked obviously, but it was like, ah, I see okay, And so then it's just like, oh, so I hear that perhaps you were distracted because of the dress that I'm wearing
and you weren't able to focus on the presentation. And the incredible amount of financial details that I provided in that presentation is that what you're missing and he said, yes, that's right. And so instead of like then ridiculing him, because obviously it's the most ridiculous thing I've ever heard, I just sit and there were people standing around me watching,
like how is she going to handle this? And I was just very kind and said, I hear that you weren't able to concentrate and that that's a shame because there was really rich stuff in the presentation. So what I'll do I will email you through that presentation and there you won't have me in the spar luckly dress to distract you, so you could just focus on the numbers in the presentation. How would that sound? And he said, oh, that would be very good, and I said that's great.
We'll make sure that happens. And so for me, instead of going oh, you idiot, like, well would you say something like that, it's very much like obviously this is a person that has absolutely no awareness that what he said was entirely sexist and inappropriate. But for me, I believe I needed to assist him in understanding how to kind of handle things rather than dismiss him or be rude or anything else. And I do have other younger women who are always with me, because wherever I go
take women with me. And I was also just watching them kind of watch me handle these situations should I have time and time again. So I've learned to actually just be very empathetic. I believe my role as a woman leader is also to assist those who struggle with women leaders understand how to interact with us, rather than dismissing them and being angry with them and marginalizing them.
Oh my gosh, what a story.
I wasn't always like that much.
Were there any sort of like key moments that you look back on and think that that changed me in terms of how I think about responding to these ridiculous comments.
Yeah. So I had another really intense situation with one of the investors who had put a lot of money in the business, and it was at a time in the business the share price had dropped and so he'd on paper he'd lost a lot of money. He was very angry. He came and he wanted up meeting with the board directors. So he came in and we sat down, and he was fuming. He was furious, and he was aiming all his quite vile anger and fury towards me
and was saying things like you should be sacked. I'm paying, and I pay for your children, and I pay for your standard of living. In all of this. It was just horrendous. And all the board members were just like, which are all male other than me, We're just like, what did we do? And then they were trying to be aggressive to him, and it wasn't what he was just making him more aggressive, and I realized, like I realized, man, he is just in pain because he has lost money.
And I'm the CEO. It's my responsibility. So I'm just going to own this shit right here, and I'm actually going to say how sorry I am. And so I got a bit emotional and I said that to the guy. I said, look, I'm really sorry. I hear that you're in a huge amount of pain because you've lost money in this investment and that's really really bad and it must be causing you all sorts of grief at home. And I'm the CEO. I'm responsible for that, and so I just want to say to you that I'm incredibly,
incredibly sorry for the pain that my leadership has caused you. Anyway, all the other directors going don't say that, doesn't it. And I just hailed him, and I was like a few tears in my eyes, and he immediately softened, and he immediately softened, and he was then emotional, and he walked around the table, came over and just gave me a big hug and said that's all I wanted to hear. I went, oh, my god, Okay, great, great, and then I walked him, you know, downstairs and out the door.
And when I came back, my chairman, who was a very experienced chairman, he said, I've never seen anything like that in my life, never seen anything like that. And I said, well, that was my genuine truth. I'm genuinely sorry that he was in so much pain, and his anger is coming from a place of loss, and I'm
responsible for that, so I'll own that. And so that was a really profound moment for me to realize to not just do all the corporate the way we're trained, which is much more a masculine way, which is don't admit anything, never be sorry, never show weakness, never be emotional. And I dropped all that because that would never work, and just was my genuine self and I was genuinely sorry that he was in pain. Genuinely sorry for all investors that lost money in any adventure that I've been in.
Also very happy for the ones who've made money pretty much I've been in. But for the ones who've lost money, you know that I really feel that. I take that as a personal a personal thing.
Yeah, as a female leader, I know you have got a lot of female mentors, and you have been one of my female mentors, one of my most wonderful ones for the last ten years or however long we've known each other. What have been some of the most valuable lessons you've learned from the people that you look up to.
Well, it's interesting that I haven't actually really had a mentor as such. I don't know why I do now that I'm working in these other fields that hopefully we'll talk about a little bit of time where I am being trained and mentored in a particular practice. But interesting enough, I didn't really have mentors in business, and that is probably because I was one of the early female entrepreneurs in Australia and we didn't really have that many mentors available.
I did have good mentors for a little bit of time through Springboard Enterprises, which is a great women led business. But I think for me, what I have learned just from around the field as a woman entrepreneur is knowing your numbers and finances are very important and it's something that women traditionally may not have had a lot of time in training and learning. It's very different now. I think there's a lot more women who were deeply trained
in finance. But that is extremely important. I think it's also to be women leaders is just to truly own our own power. So many years ago, as you would know because you're involved in it too, was the Australian Financial Review winner of the Entrepreneur and Business Women of Influence and so that was like, wow, great, Wow, I'm acknowledged as a woman of influence. And then I went, why am I only influential? And I looked at what the men's awards were, and the men's were the men's
Westpac Men of Power. So you had the AFA Women of Influence and the men of Hell the fuck what? No, Like, why am I not powerful? And so I looked at that and I looked at the definition. So influence is the ability to indirectly affect change, and power is the ability to directly affect change and so from that moment there, I was like, oh, no, we can't always just be
about influence. We women have to be about power. So for me, it was very much how do we move into positions of power, and that is in being directly able to affect change in our own businesses and other people's businesses. And so I have made sure then I've gone into roles such as I chair a venture capital fund now so I can have significant say in what we do and how we do it, and that's going
really well. And so I really learned that not just to be of influence, but really to own power and to do that in the way we women do it, which is again very different to a traditional masculine or patriarchal way. And I think women's power comes much more with caring, nurturing, support, community engagement, for doing things for purpose, doing things for meaning. And I think that's really what I've learned, what I try and share.
We will be back with Kat speaking very candidly about the huge difference between being a CEO of a private company versus the CEO of a public company where every word you say is under scrutiny. If you're looking for more tips to improve the way that you work. I write a short, fortnightly newsletter that contains three cool things that I've discovered that helped me work better, ranging from software and gadgets that I'm loving through to interesting research findings.
You can sign up for that at Howiwork dot code. That's how I Work dot co. I want to talk about the difference between being the CEO of a private company versus a public company. And let's start with just what's the difference between a private versus a public company.
It's massive, it's a massive difference. It's just so different, it's pulls apart. So let's just go through the basics. So in a private company, you can have your financials, you can have your clients, you can have your stuff, and nobody really needs to know about it other than your own internal investors. So it's very private. When you're
running a public company, everything is public. So everything you do, so every client that you have, every trial that you do, every success you have, every failure you have, every dollar you spend, everything you do on social media, everything you do in the general media, it's all in the public domain and on public record, and so that makes it enormously difficult and the real challenge I found. So we were one of the very first tech startups on the AX,
so we were very young, we were pre revenue. We're based out of New York and so the Australian capital market didn't understand artificial intelligence, American business nor startup so that was a big challenge. And the statistics are now that eighty seven percent of all AI pilots never go into production, so that will turn that around and you have one in ten pilots will ever go into into production. So we would use to announce things on the Mark stock market from our big clients in the US, so
Liberty Mutual, we've just won a pilot with them. Now, normally a private company would never have to announce that they've done won a pilot pilot. You don't announce pilots with a one in ten chance, only that it's going to succeed. So we would announce that. We'd have to announce that we had the pilot, even though our clients really didn't want to announce it, and then if it didn't go ahead, we'd also have to announce that it
didn't go ahead. And the moment we announced that we'd lose thirty percent of our share price, which could be tens of millions of dollars off the share price, And so it was this terrible roller coaster of we've won something, we've lost one, which is very very normal in a private setting where no one would have to know about it, but in a public setting then it would be all through the media. Everyone would be trolling us on social media,
and it was enormously difficult. So it really just is the public nature of everything you do, and it also is me as a CEO, I would have spent thirty percent of my time least on managing investors, the media, all of the reporting that you have to do for disclosures, and I should have really ideally had that thirty percent running the business more effectively. So it's a very challenging environment for a young company, and I don't think it's a suitable place at all for startups.
I could imagine from everything I know of you like you're just you're so who you are and you don't censor what you say. But then I could imagine being the CEO of a publicly listed company and having everything under scrutiny would be so challenging. How did you balance
your like just your authenticity. I hate that word. It's so overused, but I feel like you embody it with what is expected and what will be documented and what will be you know, influence share price and what comes out of your mouth.
Right, Yes, So that was a big which I had to make, and I really had to tone myself right down, and anything I said publicly sometimes the board would have to oversee it. And if I did say something where I, you know, was a little bit on the edge, then sometimes the board would reprimand me. And so that was all like, wow, this is like really challenging. And then when I so we sold the company two years ago, and then when I went back into just being in
private business, oh it's so great. So example, when the federal government election was recently on, and just beforehand, the liberal government came out and said, oh, we're going to do a tech round table and I went, well, a tech roundtable?
Oh?
Is that it is? That your tech policy? And I'm on social media? And then the next day Labor released their one billion dollar tech fund. I go, oh, and Labor's going to do a one billion dollar tech fund. Okay, who you know, how's this going to go? Everybody a tech round table or a billion dollar fund for technology who thinks they know what the hell's going on? And so now I'm just in social media all the time.
It's just like and you know, because I'm big on the metaverse, now it's like calling out the metaverse providers, calling out government, pulling up the politicians if they're saying something I don't think it's authentic. Really working with it was a great minister Dominello, Victor Dominello when you south was who's just I reckon? He's a champion, So you know, I can say really good positive things about him, the
stuff he's doing. It's so much better and easier being not being in the public I'm still a public eye, but not representing a public company where the share price, the share price would go up and down based on what I said.
God, how like I've heard from some CEOs of public listened companies that part of the challenge is trying to detach yourself and your decisions from a fluctuating share price. I imagine that was probably key in your role. How did you do that?
Oh?
That was really difficult.
So we would have to look at the share price every day and monitor it every day. And initially I would get very very stressed to be up to be down, and that it wouldn't make sense. We'd do a really good announcement and the share price would drop, and I had to learn the dynamics of the share market because that would mean simply that some people knew the share price is going to go up, so they would sell out to get a lift on what they'd brought in on.
It wasn't actually that everyone thought that was a bad thing, that we'd want a piece of business. So I had to learn the patterns and the cycles of the share market and the share price, and that was that's quite a skill, and there's a real science in there. And then sometimes it's completely unpredictable, and then other times it depends what's going on in the US market, depends on some other tech stocks just crashed, and so we get the wave of that. So that was, yeah, it was difficult.
It was hard not to take it very personally to start with, and to be just following it all the time. And also in the chat room, so there's this terrible place called hot Copper, which is the day trader's chat rooms where they just dissect everything, and often I would look in there, and they'd just be horrendous things being said about the company or about me or my team, and eventually I would just just not look at that anymore. Just don't look at it, don't pay attention to it,
don't take any of it on. Just focus on the business, ignore the share price to a degree, and just focus on improving the business is the only way through it.
Now. Something that you have started experimenting with is psychedelics, and I think we need some disclaimers upfront before we talk about that, if you will, Kat.
Yes, of course. So I mean in the country of Australia, most psychedelics or psychoactive plant medicines are illegal and they are also not suitable for everyone. But there are other countries in the world, some of which I travel to, where psychedelics are indeed legal and have come from traditional communities and environments as part of their either spiritual path or their medicine or their healing path. So often they're not called psychedelics, They're called plant medicine or medicine.
I'm curious as to how you've gone about kind of learning about essentially what is a whole new world for you, And you mentioned you know perhaps there might be some mentors in that space, even though perhaps there's been a lack of mentors in the entrepreneurial and.
Tech space right, So yes, let's just dive into it. So I am working with a number of plant medicines, and these are traditional sacraments that come from the earth, so that could be Ayahuascar is one of them, and Buffo alvius, which is the Sonora desert toad medicine is another one. And psilocybin, which is mushrooms. So these medicines I am being trained by guides who have been trained
for decades in serving these sacraments around the world. And my entry point into working with plant medicines actually many many years ago. So I spent time in North America with some Native American people and an elder in New Mexico where I was brought into sort of their family and trained for about a year and a half between
Australia and the US in indigenous spirituality and medicine. And so I started my journey around sort of a shamanic approach to life many many years ago and then have picked it up recently actually after on the day I sold the company, the public company that night, I traveled a place and it had a deep dive with Ayahuascar and it was a dark night of the souls. It
was the most difficult experience I've ever had in my life. Essentially, I described that I journeyed to meet my shadow self and it was the most horrendous experience I've ever had in my life.
It was terrible.
But really, then when I reflected it later, I went, oh, no, she kind of got it right. Yep, you know all of that that came out for me. It is like your ego driven, your identity driven, You're disconnected. You know, there are people you love that you're letting down. You know, you sometimes tell lies and it's like oh really no, oh yes, right, okay, yeah, I got it right. And
then I had to clean all that up. And they say that seven hours of aiahuascar is like seven years of psychotherapy, and that was very much what it was for me. And so since then, which was some years back, I've started to study and be trained and be mentored by guides in carrying these medicines so that I can understand the benefits for people and particularly leaders, in what psychedelics and these medicines can offer.
What did you do personally after having that night and uncovering these like this shadow side of yourself? How do you go about dealing with what you found?
Right? Yeah, well, so in the plant medicine world we talk about that the peak experience that you have is just the peak experience. Actually the work is in the integration. So it took me maybe six months to integrate everything that came out of that journey for me, and that was really looking at these shadow parts of my personality and then going into them and often behind them there
was some trauma. So for me, there was sexual abuse as a teenager that I then had to go into and I saw how that was playing out in how I was leading as well. My apprehension and wanting to act yes when there was an older male in the room or in the boardroom came from part of my upbringing and some trauma I had as a young woman, and so all of that the plant medicine helped me just really just get up. And because it's such a visceral experience that you go through, there's sort of no
going back from it. So you know you've met yourself, You've literally met yourself, and it's not good and so, and so it was like, Oh, if I do that behavior now, if I'm doing something out of ego, or if I'm doing something because it's identity driven, I would feel sick in the stomach. I go, I can't do that anymore. And so then I just did. I did a lot of counseling, a lot of journaling, a lot of meditation on the things that came out in these journeys.
And I've done that time and time again, and so really uncovered deep traumas that I just put down inside my psyche and had ignored. And yeah, so it's not an easy path, but it's an incredibly powerful path.
What's been your process for journaling your way through that?
Yeah, a big journaling. So I take a journal with me everywhere. I've got journals all over the place, in my handbagside my bed, in the car, and so I would just write down everything that came up for me and just really authentically, really honestly, you know, this has come up for me, or this is a trauma that I've experienced, I need to write about it. And I think once you've had these deep visceral experiences in the medicine, it's very easy to write. It just all flows out.
You've kind of got to get it out of yourself to get it out. So journaling is an incredibly, incredibly powerful tool.
And are you like almost writing like the narrative of what you've remembered or are you more writing about what are the emotions it's bringing up? Like what are you actually writing?
Yeah? Good, good question. So I would write initially the narrative, then I did this, and then I journeyed here, and then I saw this, and then I experienced this, and then that person appeared. So I do the narrative or my voice recorded, and then I'll pull out and that and go, okay, so this one was about this trauma that I had, and here are the feelings that I had. Okay, So I now need to go and sit and meditate, go back into that feeling and try and clear that
feeling that I have out of it. So I would then yet kind of analyze it and go through until I've really kind of nailed it, and then if I felt that I needed some therapy, I would go and do that. And I've got a couple of great counselors who are normal psychological counselors. And then deal with people who've had peak experiences.
That sounds like an amazing process for people that are interested in learning more where you might have picked their curiosity, what like, where's a good place to start?
Yeah, So this now because we're in what was what's called the psychedelic Renaissance, so we're seeing their arise of any interest in psychedelics all over the world. So all of the big podcast is so Sam Harris, Tim Ferriss or Remarcus, these guys, Joe wrote and all of these guys will be talking about it and they're really good
reference points. There's also Mind Medicine Australia, which is a not for profit which is particularly focused on the use of psilocybin and MDMA for therapy, and so they'll have also great resources. But because it's these substances or sacraments are legal in Australia, it is very difficult to have
any any real conversational access to things here. But certainly in Peru, so in any of the Amazon Peru, Brazil, some parts of North America, the Mexico, there's a lot of these practices are done there.
Okay. And finally, Kat for people that want a connect with you and the work you are doing. What is the best way for people to get in touch?
Yeah, so I'm really good on LinkedIn, in any of the social media channels. I'm like up there all the time on all of them. So, and it's normally just Katrina and Katrina spelled c at rio na, so it's the Gaelic spelling of Katrina and Wallace. So I'm across everything. So social media is really good for me, and I'm
super interested. Now my whole attention is being turned to the metaverse and responsible metaverse, so particularly anyone who's interested in Web three and the metaverse technologies, and for me, it's how do we build a responsible and a safe metaverse for women and the vulnerable. I'd love to hear from you.
I always feel so energized and inspired whenever I talk to Cat, even if I happen to be recording it for a podcast. What particularly stood out to me in this chat was the empathy that Cat's spoke about in relation to the blatant and quite extreme sexism she received as a woman leading a tech company. Thankfully, I've not been subjected to anywhere near as much sexism as Cat, but I am definitely going to bring more empathy to
those situations when they do inevitably happen. How I Work is produced by Inventium with production support from Dead Set Studios. The producer for this episode was Liam Riordan, and thank you to Matt Nimba who does the audio mix for every episode and makes everything sound so much better than it would have otherwise. See you next time.