# S01E11 · Transcript — Anita Grant Full transcript of [The Useful Podcast](https://useful.ventures/podcast) Episode 11, a founder-to-founder conversation between host Gokul Bala and Anita Grant, founder of Hello Hair. Back to the [episode page](https://useful.ventures/podcast/anita-grant-hellohair). This transcript has been lightly edited for readability. Filler words and false starts have been removed and the meaning has been preserved. Any errors are mine, not Anita's. ## A house of dreadlocks and perms **Gokul** Your own story starts with almost a beautiful contradiction. Your dad loved his dreadlocks, your mom permed her hair constantly — she was a perm conformist. Paint me that house. What was it like living with two such different dynamics? **Anita** We're going all the way back, I love that. My mom and my dad are complete opposites, but together they were dynamite. He had his own strengths, she had hers. My dad is the rebel. He doesn't conform, doesn't believe in a lot of the structures that are in place, and was really heavy on education and ownership — yes, you have a support system, but you need your own, and you have to keep self-educating outside of school. That always drove that spirit of being a lifelong learner. With his locks, the Rastafarian movement — if you know anything about it — they're very grounded in who they are and very prideful in what they believe, and education is a core pillar of that. **Gokul** What is Rastafarian, for people who don't know? **Anita** I wouldn't call it a religion so much as a movement out of Jamaica. They believe in peace, wellness, clean living, and the beauty of freedom and liberation — being your whole self. Locks are a connection to the spirit. The hair isn't just hair, it's your spiritual connection, your guide. It's biblically connected to Samson and his locks and Delilah — he lost his power once he cut it. So they don't cut their locks. That's from my Jamaican roots. My mother grew up in England, so very different — I'll say the word posh. Very clean-cut, very detailed, everything taken care of, from the clothing to the home to event planning. That's why she permed her hair — that was the social norm, that was how you got accepted and got a good job, having straight hair. So you have one parent who says I don't care what anybody thinks, this is who I am, and another who says this is what you have to do to show up. It's crazy that I lived in the same household. It's mind-boggling. **Gokul** What do you think that did to your own view? **Anita** It expanded my mind. It let me flow through my own hair journey with a lot more grace. I didn't feel like I had to be one certain way — upstairs my mom was like this, downstairs my dad was like that. So for me it became: find your own. Whatever works for you. ## Twenty years to natural hair **Gokul** What was your own hair journey like growing up? Did your mom teach you how to care for it? **Anita** Because my mom was in the perming stage, natural-texture hair education just didn't exist in our house — I never had a direct relationship with my own curls and coils. I grew up getting my hair plaited every Sunday; I had three sisters and one brother, so it was a lineup, boom, boom, everybody gets their hair done. My first real experience with my own hair was once it was permed. I have three sisters with full, thick, coarse hair, and I was the one with finer, more fragile hair. I'm second-to-last, so by the time it was my turn to get permed it felt like the natural progression. But my hair didn't turn out like theirs — it needed more life, it was boneless. That was my first real experience of not liking my hair, even permed. My eldest sister was a hairstylist, so I always had the newest weaves, the newest wigs, my hair always done — but zero relationship with my actual hair. A blessing and a curse. **Gokul** It took you more than twenty years to embrace your natural hair. What actually made you fall in love with it? **Anita** I'll be honest, I'm still learning to fully love it in its natural state, without manipulation. But the real moment was when I had to dissolve my first business, Fleeky. I did a lot of deep reflection and realized I'd been building from a place of lack — using that business to mask my identity. I'm enough because I have this business. Everything was rooted in that. That was during COVID, when the beauty industry took the longest to reopen. I was home with no events, no workshops, nothing — so I reconnected with my hair. Natural hair takes time to set and process, and for once I had the time. Once I actually explored my texture, I started to love it — wow, this is mine, in its natural state. That was the moment. And then I found out I was expecting my daughter, Tiana, and that's what made me go all in: she is not going through what I went through. At the very least, I'm going to teach her the beauty of her crown. ## The nickname that started it all **Gokul** You've said you want to raise your daughter with unconditional love for her own body and herself. When did you know that was something serious you wanted to instill in her? **Anita** When I really dove into where my own "I'm not enough" started. It predates the business, predates the perm — it's a childhood nickname. My siblings called me Big Eyes and Baldy: big eyes, so I must be bald too. It was a joke to them, but I was the kind of kid who dwelled on it quietly in my own corner. It created a limiting belief that my hair would never be full, voluminous, thick, beautiful. Realizing that made me understand this doesn't happen in someone's teens or their professional career — it happens in the home, and it happened to me around six or seven. So it's not something you wait to address later. I have to fill her up now, because I won't be in every room with her — she needs the language to understand that a negative comment is not a reflection of her, and how to let it go. ## From 90s magazines to a book **Gokul** You had Black hair magazines in the house growing up. What did that kind of content actually do for a young Black girl in Canada? **Anita** It was the best thing ever. Flipping through those magazines was my first view of the versatility of our crowns — any occasion, any style, so much creativity. But there was a limitation too: if my hair couldn't replicate that look, it made me feel less than. And a lot of what was in those magazines was straight hair — a perm or a weave, an enhancement. I don't think there was intentional harm; perming was just the trend, that's what everybody did. But it was important for me to see the beauty of our hair in there, and I loved sitting with my girls, flipping through, talking about styles, trying to recreate them. It brought a lot of joy. **Gokul** Is that the reason Hello Hair started as a book? **Anita** Exactly that. When I went on that deep dive into my childhood — what was good, what wasn't — I found photos where I could point to exactly which magazine a style came from. My sister's a hairstylist, so we were always pulling looks from those magazines. I thought about where that had all gone, how much goodness and celebration was in there. So when I designed the book, I intentionally mirrored those actual 90s Black hair magazines — I went searching for old ones in the house. It's rooted in and inspired by them. **Gokul** Why a book, and not an app or a product line — the more modern route? **Anita** Great question. My previous business, Fleeky, was chasing tech because tech was trending — I'm an entrepreneur, I like beauty, but I thought I could scale faster, the margins were better, it checked every box for getting funded. That's what I was tied to with Fleeky. With Hello Hair, there was genuinely no intention of leaving my household. The book wasn't supposed to become what it is today — the brand was never part of the original plan. I say business is my passion, but Hello Hair feels like purpose, because it kept guiding me in ways I didn't plan. "Books don't make money, authors don't make money" — so why would I write a book, you business mind? I call it the mustard seed. It started because people in my entrepreneurial circle asked what I was working on, I shared the book, and the reception was so positive I would've been selfish not to share it with the world. That shifted my whole lens: I'm not doing this for money, I'm doing it because I know the impact it can have, and that matters more. ## From book to dolls to a movement **Gokul** From the book to the styling dolls — was that leap planned, or the natural extension of teaching people to actually style hair? **Anita** It was the natural progression into education. Hair can be traumatic for some, or a total first-time learning experience for others, and the last thing I want is to create new trauma in a child. Children aren't going to sit still and let you practice detangling on them — it takes time and grace. A styling doll lets anyone, wherever they are in their hair journey, learn the fundamentals before they ever touch a child's hair. It reduces new trauma, reduces frustration for the adult. Cosmetology school has rooms full of mannequins — not everyone wants to become a cosmetologist just to care for their own hair. So it was really: how do we make something that already exists more accessible to the everyday person? **Gokul** Was that also coming from your own journey as a mother — realizing you might need this yourself? **Anita** Oddly, I've always known how to braid — I couldn't even tell you where I learned it. But talking to my sister recently about why she never learned, she said she just hates getting her hair done, so she never tried. So it wasn't really about me personally — it came from enough conversations with other people to know they'd need a tool before jumping straight into styling a child's hair. **Gokul** From books and dolls, you've now got community centres, six-week programs, police officers as mentors — a whole conversation about identity, safety, and worth, not just styling. How do you think about that shift? **Anita** It's funny — the styling is actually the last part of a Hello Hair workshop, because to me it's never about the style. The style is the final product. The journey is discovering who I am, understanding what's happening inside that affects the health of my hair, what I actually have access to, what's affordable, whether a hair regimen even fits my income. There's stress, there's the water in your environment — so many factors affect your hair beyond just doing "the things." I've done so much trial and error with styling and products over the years that I knew we needed something new. So Hello Hair isn't really about hair at all — hair is just the entryway, because we all have a hair experience, and it's gone beyond just the Black hair experience at this point. We've talked to enough people to know there's a huge gap for a lot of us; we don't actually know what we're doing with our hair. It's like sports — everybody's in the room regardless of background, culture, religion, gender. Hair can unite people the same way if you root it in science. We use hair as the entry point because we all care how we look and feel, and once you're in the room, we go deeper: how do you see yourself, what are your roots, are you proud, what are your health concerns, what's your access — and then we get to styling, because that's the end result, not the starting point. **Gokul** What actually happens in the room? **Anita** We have four pillars that are always signature to Hello Hair. Roots is history — the cultural importance and significance of your hair, pre-colonization, your pride. Research is where my lead hairstylist comes in — I spent three years looking for the right person, and she's a trichologist before she's a stylist, someone who focuses on the science of the scalp and hair from the inside out before she ever gives a styling recommendation. That's where we go into the whole-body systems and the actual structure of hair, because I think science is the huge missing gap. Then Journey is when the dolls come out — the styles, the tools, the products, the ingredients. And Growth is the psychological, social, and emotional piece: the societal and political pressures, the quiet emotional labor people carry around their hair, and — whether or not you have textured hair yourself — a safe space to let go of that weight, through affirmations, breathing exercises, coping mechanisms. Your hair doesn't define all of you. It's part of you, but not all of you. ## The Peel Police partnership **Gokul** Where does the police partnership come in? **Anita** That started with Peel Police, actually with an event called Fades, Nails, and Badges with Malton Neighborhood Services — a community pop-up. One of the officers there had seen my Dragon's Den episode. He wasn't from the Black community, but he has textured hair himself — I believe he's Egyptian — and he reached out because the episode resonated with him. That was interesting to me too, hearing that from a man specifically. He invited me to another event as an activator, and I love that space — if you can pour into youth with free services, I'm there. That relationship grew into a six-week program funded by an organization called ProAction Cops and Kids, which supports programs pairing youth with officers. We had three or four partnering schools in Mississauga plus the Boys and Girls Club on the youth side, and officers volunteered their time to literally be hands-in with the dolls, styling, learning everything alongside the kids. It breaks down walls for the youth. We also folded in internet safety and awareness around human trafficking and how police services can support you. It's a safe space to just be, and realize cops are people too — sometimes we're intimidated when they show up in uniform, but over six weeks you watch that relationship build into something safer. ## Dragon's Den, and the tooth **Gokul** How was the Dragon's Den experience for you, even just preparing for it? **Anita** Honestly, I grew up watching Dragon's Den, so I was geeked about it — but I also grew up really shy, most of my friends thought I was mute. I admired anyone with the confidence to do it, but I never thought it would be me. Someone in a program I was in told me I should audition. I still wasn't confident enough to go in person, but I sent in a video, quite theatrical, and they asked me to come in. Going in, I wasn't thinking about an investment at all — we didn't even have the dolls launched yet, just the book, and I thought asking for investment on a book was reaching. For me it was a childhood milestone: I'm on this journey of finding Anita again, and just walking in there was already a win. Then I unexpectedly connected with a mentor who loved Dragon's Den and Shark Tank, and she pushed me to actually firm up the pitch and go for an investor, not just the experience. What wasn't in the aired cut: right before we walked into the den, my daughter Tiana was tapping my leg while I was doing my final pre-interview on camera. I told her I was on camera. She kept tapping, and I looked down and she was grinning — she'd had a loose tooth for six months from a school accident, and it chose that exact moment to fall out. She started crying, the producers panicked, my husband offered to take her out, and the crew said I might have to go in without her. I asked her how she was feeling. She wiped her tears, held up one finger, then two, put her hand down, and said, "Mom, I'm ready." I get emotional every time I think about it — if she's ready, I have to be ready. Once we were in there, it didn't feel like pitching or proving myself. It felt like a conversation. I was just being Anita Grant. Both of my goals — being proud of myself, having my daughter stand beside me — happened, and I got an investment on top of that. It validated that this children's book is enough, that the story is enough, that this is going to impact millions. I don't think the dragons were looking at revenue, because there wasn't much yet — they saw the mission and the size of the opportunity, and I felt like I was the right person to lead it. **Gokul** How did the show change you as an entrepreneur, even after it aired? **Anita** It's still paying off. I tell people: do it for the exposure alone if nothing else. It gave us credibility — we're a VC-backable business, even as a children's book. For the Black community especially, seeing something like that from a mustard seed felt like a moment. I always say my wins are wins for my community, so it's less "I'm special" and more "this is possible for you too." **Gokul** A lot of people believe their business isn't VC fundable because it doesn't look like a traditional tech company. How would you want them to think about that? **Anita** I'm a big believer that if you tell yourself you're not, you're not — and once you tell yourself you are, you are. If I want something, I have to believe I deserve it first. If I'd walked in still thinking "I'm just a book," I wouldn't have prepared the way I did. That mindset shift changed how I pitched, how I gathered my financials, what I understood "VC backable" to even mean. I had to do a deep dive into my financials for the first time in my life. And on the show, I said clearly that the goal was to build a whole world — an animation eventually, not just a book. Preparing for that pitch forced that expansive mindset. Where you are today isn't where you'll be tomorrow, but you have to be able to tell that story. That's what makes you VC backable — not today, but what they can see you building. Everything's VC backable. Whether you take the VC is a whole separate conversation. Post-COVID, the VC world has changed a lot too — it used to be easier to raise and inject capital to grow. Now investors want a lot more proof of validation and product-market fit before the money moves. That shift is real, and you have to prepare for it differently than you would have a few years ago. ## A UK prison, and men who braid **Gokul** I wanted to bring it back to the UK — your dolls crossed into a UK prison, where incarcerated fathers learned how to braid. What brought that about, and what did watching it do to you? **Anita** That is so new, I'm still a little "whoa, what happened." What I've noticed in this journey is that I'll say I want to do something a year before it happens, and things just align. I went to South Africa last year, China this year, and with the tariffs and everything happening with the US administration, I decided I didn't want to limit myself to the North American market. My mom's from the UK, I have family and roots there, and when I think about how the UK relates to hair and identity, they really get it. I'd been following a company called Treasure Tress for a while and knew they'd be a great partner, because Hello Hair isn't just about selling books and dolls — the education has to come with it, and if I couldn't be there physically, a partner like them could carry that piece. So I cold-emailed them, sent some DMs, just to pilot the brand and test whether my assumptions about the UK were right. The timing turned out to be divine — they were already planning a workshop, and when I met their founder, she told me one of the most common pieces of feedback they got was: why are we styling straight hair when we're trying to teach people how to care for their textured daughters? It doesn't translate. Once we connected, it was obvious our gap and their gap were the same gap. The prison program itself was directly between Treasure Tress and the facility — we came in as the partner for the styling dolls. That wasn't our original partnership, but the timing lined up so well that they asked if they could use the dolls for the workshop, and I said absolutely. I saw the videos, the braids, heard the stories from the men, and I knew we'd have an impact — I just wasn't thinking about all the different angles that would open up. Credit to Treasure Tress for letting me be part of that. We've already gotten interest in what's next, which prison, which space — doing more of these workshops with men specifically is part of their initiative now. **Gokul** What does it tell you when men themselves are asking, "Is braiding even for me?" **Anita** It shows how deep the gender roles run. Mom, sister, auntie — almost always somebody other than dad or uncle is doing the hair. But gender roles are shifting; we're mostly two-income households now, and that has to include how we care for our kids. There's real desire from men to be included — they've just never been asked, so they've never put their hand out, but there's no resistance to learning. And men have their own hair experiences too, which we tend to write off as a "women's issue." I've talked to plenty of men who genuinely don't know what to do, and it affects their self-esteem and confidence just as much. I want to create more spaces for anyone to learn and explore, and we'll be expanding Hello Hair to be more representative of men and young boys soon. ## Four years in, and a team of her own **Gokul** Congratulations, by the way — Hello Hair just turned four. Your team put out the anniversary post before you even could. What's it like watching your team move past you in some ways? **Anita** It was so special. With my first business it was really just me, maybe a contractor here and there. To be at a place where I can say I have a team — I'm still learning what that even feels like. I needed help, and it's not always easy to ask for it. My team is aware of the weight I carry, and to see them take some of it off me, and articulate our four-year anniversary so beautifully — Sandra did an incredible job putting that story into words, and I'll name-drop her because it's such a personal brand to write about. It felt like a reflection of growth, of leadership, of the ability to see bigger — I don't have to do this alone, and with the right people, this doesn't have to stay a small business. It can grow globally. That's where we've been in the last year: growth beyond what I can fully grasp on my own, which reinforces that we're on the right path and that I have a team behind me now. It brings a lot of joy, excitement, and peace. ## Mission and margin **Gokul** Hello Hair is essentially a social enterprise, and mission and money can pull in two different directions. How do you keep it alive as both a business and a cause? **Anita** That's something I'm just now learning to balance. In the beginning I did a lot of community work with no returns at all, and I burned out jumping from thing to thing with no structure — it took away from actually building the brand. I had to realize that having revenue and profit isn't selfish, and it isn't taking away from giving back. In order to keep making impact, I have to be able to sustain it. Without revenue or profit, I can't service anybody. So the first shift was in my own mindset — letting go of the guilt around money. I'm not a capitalist; I'm funding greater impact long-term so it's sustainable. The second part is that I've narrowed down to a handful of social partners I really trust — I know what to expect from them, how I'll show up, and I can stay consistent even when we're not seeing the profits from that work. That's far more manageable than being everywhere at once. And I've put systems in place so the book, the dolls, and the e-commerce side can run on their own, simultaneously. It's really about structuring what percentage is community and what percentage is revenue, and keeping both in motion — not one versus the other. ## The goal: just to be **Gokul** Your site talks about honoring the past, educating the present, and preserving culture for the future. If Hello Hair works out exactly the way you want, what changes for a young Black girl's relationship with her hair — or anyone's relationship with their hair? **Anita** Honestly, I think we think about hair way too much. My next book might just be titled that: why are we so obsessed with hair? I don't think we want to be — it just takes up too much real estate in our minds. I'm planning a hairstyle three months in advance, thinking about the weather, how I'm going to show up. It genuinely impacts your daily life. What I want is for people to just be. God made all of us perfectly — perfectly imperfect. You're enough as you are, so why are we trying to alter parts of ourselves that already exist as they should? I want us to get to the place where we can just exist, and for people who don't understand our experience to understand the harm in some of the language, and how certain rules and laws can limit us — while also honoring and passing on the knowledge so my children don't have to experience what I did, because I'll have already educated them, and they can pass that to the next generation, through practice and care, so it never feels like "going to school to learn hair care." It's just passed on. My real goal is to let us exist. I just want us to be. **Gokul** And have hair just not be a topic of discussion at all. **Anita** It's a part of me, but it's not all of me. There's so much more I want to share with the world — I don't want to be known for just this. I think there's a lot of pressure on how I show up because of it, and if I didn't have to think about that, you'd probably see more of my positive qualities. It's just a matter of letting us exist, and then we can focus on the beautiful traits we already carry inside, and share that with the world instead of carrying the weight of it. **Gokul** Thanks so much for coming on, Anita — it was great talking to you. **Anita** Likewise. --- Back to the [episode page](https://useful.ventures/podcast/anita-grant-hellohair) · [[podcast|All episodes]]