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Patsy quit her job. Susannah quit the city. Now they’re on a quest to find the path through the wobbly middle of their careers. This podcast is for every woman who’s asking “What now?”.
Hosted by Susannah de Jager and Patsy Day, The Wobbly Middle features interviews with famed city superwomen, dazzling entrepreneurs and revolutionary midwives and doctors who reveal what they’ve learnt through their own wobbly middle experiences.
[00:00:07] Susannah de Jager: Welcome to The Wobbly Middle, a podcast about women reinventing their careers by Susannah de Jager and Patsy Day.
[00:00:21] Patsy Day: Hi Susannah.
[00:00:22] Susannah de Jager: Hi, Pats.
[00:00:23] Patsy Day: How's your wobbly middle?
[00:00:24] Susannah de Jager: I'm really thinking about community this week and how important it is in so many ways. If women are often characterised as good at creating social community. Then men, by contrast, are often characterised as better at creating work networks. This can have interesting impacts for both and I believe that just as men need social groups and communities to guide them through difficult moments in life, women need both informal and formal networks and community focused on their careers and careers and their development in that domain. We spoke recently to Helena Morrissey who made this point about the wonderful impact of the Diversity Project programme and how important the community element had proven for participants. We're about to speak to Debbie Wosskow who's built a female network in the past in AllBright I'm really hoping that The Wobbly Middle will be a source of community for those going through changes and career wobbles so that women can be supported across all areas of their varied lives. How about your wobbly middle?
[00:01:25] Patsy Day: I'm feeling very invigorated after diving into the world of Debbie Wosskow. She's pretty dazzling and in an earlier call with Debbie, she really challenged us to identify our mission for The Wobbly Middle and you speak about community and I think that the goal is to energise women to pursue fulfilling working lives, whatever that looks like for them and to help them navigate and explore how to get there. So to that end, we're really interested in stories about women in their midlife. What they're struggling with, what's inspiring them, and if they're through it, what tips they have for us. So if anyone's listening and wants to share their story with us, please drop us a line. Our email address will be in the show notes and you can also find us on Substack at The Wobbly Middle.
[00:02:18] Susannah de Jager: As we've mentioned, in this episode, we're interviewing Debbie Wosskow, OBE. A dynamic force in the world of entrepreneurship, investment, and advocacy for women. Debbie had her first taste of success selling scrunchies in her teens, then opened her first business, a marketing and communications agency in her twenties and sold her second business, Love Home Swap, for a whopping £53 million in 2017. Not one for resting on her laurels, she then co founded AllBright, with the aim of creating a monster global sisterhood of women in business who could connect, so that then we could change the world, she said. With a different business for every decade and now 50, Debbie has co founded The Better Menopause, which aims to empower women at midlife with science backed solutions. She is also currently serving as co chair of the Invest in Women Taskforce and is a non executive director at Channel 4. Debbie is an angel investor, investing in women led businesses, showing that she truly embodies her own philosophy, that the sisterhood works. I can't wait to hear more.
[00:03:26] Patsy Day: Debbie, thank you so much for your time today. I've heard you say that my life has been the story of women. I'd love you to tell us about your working life through this lens.
[00:03:35] Debbie Wosskow: I think as we get older, we have a bit more time to be reflective around why we are the way we are, why make the decisions that we make in our life, in our careers and looking back, there are two things that have helped me get more perspective. First is writing a book and so when I co-authored Believe, Build, Become: How to Supercharge Your Career, you have to lock yourself in a room and think about yourself, which we generally as women don't have any time to do and the second thing, frankly, is doing therapy where you have to delve into patterns and life choices and pivots and my story is a story of women, it really is. I grew up in a matriarchy in a reasonably typical Jewish immigrant family where the women ran the household and they ran businesses. my mother ran a business with my stepfather and all of this seemed entirely normal to me and it's only when I entered the world of work that I realised that work life wasn't really like that and I think throughout my life, the women that I've met along the way have changed my life as business partners, as part of the sisterhood, as network, as investors and I've got lots of sisters and I think for that reason, I always seek out female company and female partnership and it's only now as I hit 50 that I realised that that's been the soundtrack to my life, that without the women that I've met along the way, life would be profoundly different. It would be much less fun, I'd be much less successful and I think female role models for me and just women who make me laugh are a big part of the joy that I get in life.
[00:05:14] Patsy Day: You mentioned pivoting. A lot of the women who'll be listening today are pivoting in their life. Some have chosen to step away from existing roles. Some have had change forced upon them. I wonder if you could tell us about a time in your life where you've had change forced on you.
[00:05:33] Debbie Wosskow: II've built three businesses to exit and now I have a portfolio career, but I'm also the biggest shareholder in a business called the Better Menopause, which is science driven supplements for perimenopause and menopausal women. All of my businesses have, I think, done two things. The first is that I'm a very simplistic entrepreneur, so I need to be able to get excited about the business and feel like I'm a customer of the business in order to turn that thing from a moment of I've had an idea to actually doing it and scaling it. So for Love Home Swap, I was the woman with young kids that wanted to swap her home, having watched the movie, The Holiday, if I wanted to swap my life when my kids were small. For AllBright, I was the woman who knew that networks mattered, who was driven by building better networks, better access to funding for women, for The Better Menopause, that's where I'm at in my life. I founded the business, off the back of being in perimenopause and recognising that there weren't solutions for women like me.
So part of it is around being able in a To Kill A Mockingbird type way, to put myself in someone else's skin and walk around in it. But the other thing is necessity is the master of invention, right? When I founded Love Home Swap I had no money and I was divorced and my kids were tiny and I don't think we talk enough as women about pivot, if you like, which I use, but change and reinvention and newness for me has always been driven by the fact that I've had to do it and I think we need to frame that conversation a bit more when we think about why women have different choices to take throughout their life. Sometimes it doesn't feel like a choice, right? And Love Home Swap in many ways was amazing, it was the business that made my fortune, that gave me financial security, but I mean, blimey, like the clock was ticking on making that happen.
So I think it's those two, the push pull for me has been vision and I can and I will and the test for me is always when I've had an idea, is it giving me goosebumps, am I obsessing about it, but the thing that I think we need to have the conversation about is sometimes darkness is as motivating as light. I've got to have the sunlit uplands, but I've also got to have needing to do it and a little bit of a kind of FU list as well, I need both and so for that reason, I think it's taken experience and it's taken knocks and I think from the outside, everything can look very glossy, can't it? But it hasn't been and I think if one can reframe the conversation, which may be part of the pivot into the crappy stuff makes us who we are and that sounds really trite, but for me, all of my best ideas come when my back's against the wall and it's always been like that for me. So in a way, if we can embrace the unexpected twists and turns that life takes, I think the ability to do that is what makes a successful entrepreneur.
[00:08:31] Patsy Day: You speak with such energy about that capacity to bounce back, reinvent and regenerate and I've heard you speak about the positive power of personal reinvention, which is, I suppose, what you're talking about now as well.
[00:08:45] Debbie Wosskow: You know, it's just fun. I get bored really easily and I do see it as a gift. I think the chameleon like ability that we have as women. That the natural biology of our life takes us on because at every stage you have to be someone different, learn how to do new things, embrace a different balance or series of priorities in our life, I find that terribly energising. I don't want to sound like Pollyanna because, there are days when it feels just shitty and annoying, but I think I do have a capacity, even when it is shitty and annoying To see the different chapters of our life as a gift, every decade of my career has been different and I think it's a combination of neuroplasticity. So, it's important to learn new things. I like learning new things and it's important to be around new people, although there's a red thread through my career where I've worked with a lot of the same people for a long time, those relationships and that continuity is important, but combining those two things I find hugely energising and that's why, I still continue to bounce out of bed 25 years into an entrepreneurial career.
[00:09:54] Patsy Day: What surprised you about being in your forties? And what did you learn about yourself through that period of real change for us in our bodies, but also in our sense of self?
[00:10:05] Debbie Wosskow: I mean the forties were my AllBright years, really, you know, I sold Love Home Swap in 2017, so I would have been 43 and then the rest of my forties were spent building a business, which was the first business that I'd built in partnership with another woman, so Anna Jones, who's my partner in crime, although she has very grown up job, she's CEO of the Daily Telegraph. So I think there was a lot in there about sisterhood. You know, if you ever came to an AllBright then written in neon and the entrance halls were sisterhood works, that I think was a very important part of what the business stood for. They were the pandemic years,scaling a business, hanging on to a business in 2020, where a vast part of what it stood for, and frankly, a vast part of its revenue was around physical space. It was an international business, so I learned some very hard lessons about commuting to LA twice a month, which I wouldn't recommend, which is pretty grim, and how to motivate yourself in the hardest commercial position I've ever found myself in, where our revenue went from scaling, supercharging turbo to zero, , overnight, and I couldn't get on a plane and I learned a lot about how deep I could dig, I learned a lot about doing it with someone else, so doing it with AJ, but I'm proud of what we did. I'm also proud of the fact that we could be there for our community because we were all locked in our homes. We saved the business and we kept it going, we got a good outcome for the business and for the investors and the team, but it was hard. It was the hardest thing I've ever done I learned about humour, you really, in those times, yes, you knew people with skills and bear in mind, our whole team was hired to do a completely different thing, so we're having to re orientate everybody from our living rooms, but you just want to be around people, for whom the glass is more half full than it's half empty in those times and I've always sought those people out, sought those women out and they remain the sort of soundtrack to my life and the light of my life. So my forties were about that. They really were about prioritising relationships and recognising that that's how we keep our cup full actually, is the relationships that happen outside our home.
[00:12:29] Patsy Day: You have the entrepreneurial skills, confidence, resilience, these are all things that people see in you and assume that they are just your natural gifts. But in your book, you speak about how everyone can develop these and they are things that can be worked on and built.
[00:12:45] Debbie Wosskow: Yeah, I think all of those attributes can be learned and I think they're muscles that need to be worked and I think if I look across my female entrepreneurial cohort, who I'm lucky enough to call friends after so many years, we're really different from one another, in the whole conversation about female founders, we need to make sure that we don't think one size fits all cause it doesn't. So, just thinking about people I've known over the years, yes, you've got people who are natural extroverts like I am, I get my energy from being around other people, I like selling, I'm good on my feet. But you get plenty of women who are profoundly different. Who are unbelievably skilled, who have to work on other things, just as I have to work on other things. So we're not just a cookie cutter model. The second point to that is all of those attributes that I talk about in the book, confidence, resilience, entrepreneurial mindset. I'm minded of it because I gave a talk at my daughter's school on Friday of last week to the new lower six about all of this and in a show of hands, at least right now, very few of them thought they wanted to be entrepreneurs and in a way that didn't surprise me because it's generally not seen as a career path for young women and also it doesn't matter because all of those attributes are important, whatever you do and I think you can train yourself and one of the things I talk about in the book and I live every day of my life is this sort of quiet companionship of routine, you know, when things have been really tough and they have been really tough and I'm minded of it, because I would say to my mom, like, don't read the comments when I have a piece of press, cause they're always absolutely awful, but I did do an interview with the times a couple of months ago about burnout, which has been a factor of my late forties and the comments were so awful I mean they were horrendous, minded to say something because there was a theme throughout which was, what do you know about stress or pressure or an ordinary woman's life? You know, when Anna and I co-founded AllBright the press again and the comments was very much focused on our rich husbands, which was ironic because I didn't have a husband and I love AJ's husband, but he wasn't rich. So, I think that there are just the pressure that we can put on women telling their stories and recognising and acknowledging that it is hard, but this is their way through it. That's why podcasts like this are important, right? Because every woman's got story and difficulty, but I think we can all exchange honest, authentic stories about how we do it.
[00:15:26] Susannah de Jager: I think that one of the great benefits of being an entrepreneur is that you can create a workplace that is built for you, for women from a female perspective and you have been able to do that multiple times over and I wonder if you could speak to maybe, if you see there being any core tenets that you really try to create in your businesses?
[00:15:49] Debbie Wosskow: This stuff isn't easy, right? So at AllBright, we had a very, very big workforce that was 98 percent female and we bridged every part of a woman's health and economic journey, early 20 somethings through to IVF, through to pregnancy, through to young newborns, through to school age, through to menopause, like we had lots and lots of existential questions around maternity, paternity leave, flexible working. It was amazing, it was a privilege, it was hard, really hard because in the end, what's the balance with all of that and with the opportunity to create culture? You know,there was a massive confusion, sometimes in the marketplace and sometimes with talent that we were hiring, that because we were female founders and because we had youngish kids, it would be run a certain way, we existed to make money and I think where it gets complicated is when profit and purpose combine and what I don't want to do is to gild the lily and I see it firsthand at the moment because I'm a founding advisor to an amazing woman in private equity, Brynn Kennedy, who's raising a fund for net zero and climate tech called Smart Society Ventures. She's invested one fund, she's on her second and she's due to have her first baby in December and I'm watching close at what she's doing and I've been her, right? I've flown until the last possible day I can fly, I've worn a dress and a pair of heels and stood up and pitched for money at eight months and three weeks pregnant to a bunch of men who've been like very worried I'm about to go into labour, like I've done all of it. My children are nearly 16, nearly 14. I think there's been some culture shift. In other words, I never, ever talked about my children when they were small at work, ever and I certainly would not have talked about them to a room full of men and I think a few things have changed and some things haven't.
There are more high profile female founders and investors than they were, but believe me, the data is bad and in fact, the data's got worse, 2023 to 2024, so feels better, but it's not really that much better.
I think you've said something else interesting here about obsessing about an idea and that that's how you sought, the wheat from the chaff of what's a good idea. Can you talk a little bit about that process? Because I think people listening might be really interested of how do you test something other than just your own interest, because we often read about people being told no a hundred times and I said this to Patsy the other day, I feel like if I got told no a hundred times I would have stopped already and so how do you have that self confidence to keep going and how do you sense check it maybe elsewhere?
I think I've probably grown up a bit with this stuff through experience, but the process for me in as much as it is a process is the first thing is that you have to be open to ideas. All of my moments have been moments in my life on a plane, watching the movie, The Holiday with a doctor telling me that I was in perimenopause because my gut health was so rubbish and I'm like, there's a thing and what's that about? I think that's mindset and I think it's being open to the universe or that kind of stuff. I mean, I'm not like full cosmic ordering or anything, but I think you have to be open. So I think that's one. Two, there's data. So what happens to me is I have the idea and then I obsessively look at the market for like a week or two. Is it a good idea? What's out there? You know, cause I'm a nerd really and my businesses tend to be digitally driven. I look at the data and some of it's a bit technical, like, is there enough search to buy, what does it cost? What does the economics look like? And I've got people that I've worked with for a long time who are different collaborators, AJ being one, my brother, Ben, who I worked with at Love Home Swap, Chris Watson, my very long suffering CTO, and they're quite used to me doing, I've had this idea, what do you think? So I do some of that and I think what's the growing up bit? AllBright definitely became, partly because of the pandemic and partly because of the market, a brilliant thesis and a fantastic community in want of a business model. It was clubs, then it was digital platform, then it was commercial partnerships, then it was education, it was such a beast because we were always chasing the money.
So with Better Menopause, maybe this is my 50 something process. I did that, I've had an idea because I'm in with the doctor and then I came out, I called AJ and I'm like, I've had this idea, she's very used to this kind of conversation and then I went very specifically to where is the margin and the answer to where is the margin in the menopause market is subscription supplements and then I go to what I know, and I know subscriptions, my last three businesses and some of the stuff I back has got subscription at its core and and so does Anna because she's from magazines and so we could kind of get our heads around that to get together a 10 page deck. This is the opportunity, this is the brand, this is the business, this is the model. I tend to have like a very crappy Excel and Then I immediately go to network and I have got a very big, very high end network. I've spent bloody years building it, but that's kind of part of my pixie dust.
So I'm like, right, who do I know that I can connect in through this person and this person, I can get to a supplements manufacturer through this person and this person, I can get to some of the midlife talent, I can figure out whether they're interested. I can build a website like this. I can bring in a Shopify, so that I can hack with my money and Anna's money, a prototype and I can have a route to market and I can get somebody to help me scope a product that costs X and does Y and put my money where my mouth is and Anna's and then I've got a proposition that I can go and raise money to build. That probably takes me eight to 10 weeks. When I'm a maniac on a mission, I'm on a mission I have a network cause I've been doing this for so long, but LinkedIn is just a total gift and it's also why I have this kind of alter ego on LinkedIn, which takes quite a lot of time, but it's cause you're only ever a connection or two away from someone you want to get to, if you've invested in that and then the ultimate test for me is can I get people to back it? Can I tell the story in a compelling way with a route to market, to get people to come in alongside me? The expectation is always I will invest personally, people expect that and that's fine. you've got to start somewhere and the start somewhere for me is what's the thesis? What's the business model? Where's the margin? Am I prepared to write a personal check? And can I spend eight to 10 weeks testing and getting something together sufficient that it could be greenlit?
[00:22:51] Patsy Day: Told you she was invigorating.
[00:22:53] Susannah de Jager: Yeah. That was, I'm like, right, I'm gonna go do it now! So hopefully people at home feel the same way.
[00:23:00] Debbie Wosskow: I will say on all this, it can be for anyone, but it isn't for everyone. That's actually a really important point. So I firmly believe anyone can do it, I really do. I feel like anyone can learn the skillset, people can learn how to sell, how to execute, how to build a team, how to control their own financial future. I want us to see the great economic shift of capital to women, but it's not for everyone. It's a weird way to live. It's very, you've got to be comfortable with uncertainty and you've really got to back yourself and that isn't for everyone and I say this a lot because I think for the great gift of my career is that I started doing this when I was so young and I had nothing to lose. There are a lot of reasons not to do it as a woman in your forties, to do with everything that makes it risky. The quid pro quo is around, I'm not ever encouraging anyone to be reckless. You know, Anna can talk to this very, from her own lived experience, she was a grownup CEO of her, she had the corner office, she worked her way up, she was 41. But a big reason that she could run away and join the entrepreneurial circus with me is cause she'd save some money. If you haven't, it's a horribly stressful way to live because your financial future is very uncertain. The upside's enormous, but your earnings along the way, for your sort of audience will conventionally be less than they would be in a job and I think you've got to both get comfortable with that and be ready for that. So it is risky in lots of ways. It's less risky the older I get because I've got more of a track record and I've got nest egg and I'm now building out a career, which is different because I'm feeling like I want different things to scratch different itches.
[00:24:53] Susannah de Jager: You spoke there about being comfortable with uncertainty, or at least being prepared for it perhaps, and I think you've articulated very well the entrepreneurial journey and how that brings with it financial insecurity as well. But interestingly, I think that being comfortable with uncertainty is something that even if you want to go into a new career and pivot, not to running your own business, but something new, I do think that's something that women listening are going to have to resolve to risk and that that's something that decoupling again that you've spoken to from an identity, I'd love to hear if you've got any tips for how you navigated that because I think that lots of people go through that at different stages.
[00:25:39] Debbie Wosskow: I'm not sure it's an overnight thing. So I think you have to take yourself on a bit of a journey, but I think life thrusts some inevitability at you and if you'd said to me, I've been divorced now for 13 years. Nobody wants that. My kids were three and one, like it was kind of a disaster. It felt personally a massive failure and most certainly not how I saw my life working out, but it made me, because I had a very uncertain future. I had an uncertain future financially and I had an uncertain future because my life had not taken the path I thought it would take and everything was up for grabs. Who I was, how I define myself, where I lived, how I worked, the only thing that was locked in was I had to go make some bloody money. and my story is maybe unusual because conventionally women don't get divorced when their children are that young, although it happens, but blimey, they do get divorced when their children are older right, and we know that, and we know it's going to be half of us.
So, our life is long and exciting and amazing and shitty and uplifting and depressing in equal measure, sometimes in any given day, right? But I think it's about what you do with it and I have one other rule that, just thinking about the how, that may be useful. I allow myself 24 hours to feel crap about anything. I'm like, right, you can wallow, you can punch the pillow, you can not wear your makeup, you can cry on your friends and your sister, for a day and then it's done and I'm pretty disciplined about that actually, but on the other hand, I'm not a machine. So I do feel it, of course I feel it and the other thing, my next sister down is a therapist. I absolutely avoided therapy for years, hated it. Did it when I had to, like couples counseling and all that, hated it. But my sisters really forced the agenda with me and that also helps you to manage uncertainty and change, because what I found were two things. One, my girlfriends in the main have been my girlfriends for 30 years and whilst they love me and I love them, you get a certain sort of point of view, one, and I think two, when things were really, really awful as they have been at some points in my life, I tend not to want to talk about it because I'm clinging on and I feel it's humiliating and I'm not really one to broadcast the failure or the despairand I think doing five o'clock on a Monday every week for a long period of time forced me to face up to some of this stuff and also gave me a faster track, I think, to processing some of it and to embracing change and to shaping my mantra which has been more joy and that's the test I run over anything, professional or personal, is it going to give me more joy? If not, then no and the extension of that in my work life is this triangle of have fun, make money, don't work with assholes and I've hugely compromised on number three during my career because I just had to, right? But now I'm old enough and ugly enough to go, fuck it, no, I don't want to work with that person, I don't want to take money from that investor. I just don't want to, so I won't and I think having a bit of a platform in my own funny work way to call that stuff out and to offer women some sense of how and solutions and a language for staying true to themselves. I see as part of my mission and this kind of goes back to the, if you can, you should, I feel that very strongly in this decade and that's why I'm doing a lot of the stuff that I'm doing to try and bring about change.
You have so many people coming to you asking for you to solve questions and how do you suggest we do this? How do you suggest we do that? What are the big questions you have? What are they? I mean, look on a day to day basis, I've got as many questions as the next person about what to do, about small things and big things, about what the point is, you know, a thousand and one questions around my teenagers, crikey. But I do tend to be clear about my why, even when it changes and I find that keeps me focused.
What's the big question? For me, it's about how to make a difference. I'm very focused always on productivity and I'm very output driven and I am someone who gets a lot of shit done, but is it the right shit? I guess that that's always my question, it's easy to be a busy fool, isn't it? And it's easy if you're motivated by crossing things off the list, which I still do every morning and I'm getting to the end of the weeks or the months now and saying. Is this the right stuff? Is it the right balance? Not in a work life balance type way, but if the big gift I've got to give is time, am I achieving the things that I want to and should be achieving?
[00:31:05] Susannah de Jager: I think that's a really interesting point. That you can be motivated by just ticks and boxes and again, I think that therapy or coaching can really help with this. It's taking a step back and working out what you want to have achieved in a year and then holding yourself to account. Am I achieving things? Do I still feel that the why is in the right place? Debbie, thank you. This has been just such a generous and informative conversation and I have really enjoyed it and I hope those listening have too.
[00:31:31] Debbie Wosskow: Thank you, thanks for having me, both of you.
[00:31:33] Susannah de Jager: Thank you for listening to this episode of The Wobbly Middle and Merry Christmas! We're going to take a short break so you can enjoy families and time, but we'll be back on the 8th of January for the final episode of Season One.