Talking Failure, Feminism and Funding with Shabnam Aggarwal, Author of ‘Freedom to Fail’
Shabnam Aggarwal is sharp. When she’s seated across from you, you sense you need to bring your A-game. It’s not a judgmental or expectant vibe — it’s inspirational. And that’s why the founder of three companies has written her book, Freedom to Fail: Lessons from My Quest for Startup Success: to inspire others to take risks, even if it means failing by conventional metrics — to “walk out of this boxing ring with our heads held high, our chests puffed out, and our fists up ready to fight the good fight again,” she writes in the introduction.
The interview has been edited for clarity and length.
The Swaddle: In the spirit of your book – are you a failure?
Shabnam Aggarwal: (Laughs) Yes, definitely, and proud of it.
The Swaddle: Your book takes us on a journey from when you were young, to the very recent past, spanning your childhood and education, to your professional life as a founder and leader of three companies. It becomes clear that your father had a big influence on both. How much of your choices were rooted in a desire for validation from him?
SA: A large percentage. I think actually for a while it was probably 100%. Choosing engineering as an undergrad degree was partly being pressured into and partly wanting to make my parents feel proud. So I think that idea of being validated and finding things that made my community and family proud of me, was probably the motivating factor in the beginning.
The Swaddle: It seems like that lessened over the years, as it does for many people as they grow up. Or is it still a driving force for you?
SA: You know, it’s something I battle with. The minute I’m aware of it, I try to hedge a little bit and pull back from it, because I think that if decisions are too dependent upon external validation, then you’ll never be satisfied, or you’ll never feel ‘happy,’ with what you’re trying to get done.
The Swaddle: Speaking of early life influences, you had a female entrepreneurial role model in your life from a young age, in your mom. But you chose a very different version of the entrepreneurial path. How did her experience and watching her build a business influence your choices?
SA: She looked at her career in such a different way from so many parents that I saw. Even my own father. I think she sort of thought of it as, ‘Even in my free time or on the weekend, I should do things I’m passionate about, and if I can make a career out of it, that’s wonderful.’ Definitely it was influential – a lot. But I don’t think I was like ‘Oh my mom’s an entrepreneur, and I want to be one, too.’
But as I got older, and as I progressed through my career, I noticed myself sort of gravitating towards a lot of the same stuff as she did. I was an engineer, too; she was an engineer. [Later] she moved into the education industry, and I had sort of the same trajectory. The only big difference is that I thought of entrepreneurship as a chance to affect millions of people, and she thought of entrepreneurship as an opportunity to deeply affect a few people. But, we both are really interested in helping kids grow and teaching them.
The Swaddle: It seems like, for a previous generation of female entrepreneurs, society was like: Ok, you can build your business, but everything at home has to be done also. Does that feel different now, in terms of what you expect for yourself, in terms of what is expected of you?
SA: I think in my mom’s generation it was a lot more difficult to stand up and be a sort of righteous feminist and wear that on your sleeve. In our generation, I was brought up in the US, where it was a lot more encouraged to be who you are, be a feminist and be a rebel, to some extent. My mom went through an arranged marriage, then came to the US and didn’t have any family other than her husband and his family. So, she didn’t really have a choice to be a rebel and work against what the system said. She sort of did it in her quiet way, which was going and getting a Master’s degree, and starting to work, and sure, still do all of the chores at home – cook, clean, manage everything, raise the kids.
But now, she has sort of found her own corner of space, and she talks about how she handles all of the finances in the house now, whereas she and my dad first got married, she couldn’t spend money without his approval. So, it’s shifted over time. And I’ve intentionally chosen partners who — my partner today would never ask that of me, that stereotype or gender bias. I’m in a situation where I can demand equality, and it’s very happily given.
The Swaddle: It is a different world for women, today, but your book does speak to more obscure inequalities in the female experience, especially the female entrepreneurial experience. There were two parts of your book that spoke to this: One, your first investor pitch. You’d planned to wear a pink dress, and you felt really confident in it, you’d practiced your pitch in it, and were really excited to go into the meeting specifically wearing it, because it was such a part of the plan, of who you are. And then the organizer made you put something over it.
SA: A black polo over it, yeah.
The Swaddle: Yes, and the pitch didn’t go well. And later, you’re having an investor meeting, and you’ve been told, ‘Oh the investor is quite traditional, you should probably wear a salwar kameez,’ and you write about feeling uncomfortable and not true to yourself. These trade-offs in authenticity, how common is this to the female entrepreneurial experience?
SA: It happens all the time. Every female entrepreneur I’ve ever spoken to, we’ve all had to hide our feminism and our femininity in some way, especially in India, where being female is uncomfortable for men in power, often. I noticed that the less and less I was feminine, the more comfortable people felt with me. You know, if I wore ill-fitting clothes, or if I didn’t wear my high heels, and things that made me feel proud and comfortable in my body, people — men especially — felt a lot more comfortable with me. And being feminine – that doesn’t always mean high heels. Just, for me, that was what made me feel confident.
But there was this weird assumption that women can’t be good at tech. There was this idea that, to be great at tech, you have to be more masculine in some way.
I sort of did it because there is that power dynamic where you feel, as the entrepreneur, you need to succumb to what investors – and this is true for both men and women, I’m sure – that you need to bend yourself to what investors expect of you, and how they think of you, what their perception might be of you.
The Swaddle: And did that bending affect the vision and success of what you were trying to do?
SA: It really affects you from a mental and emotional perspective. When you’re always changing and becoming a chameleon to whomever is sitting in front of you, you’re losing parts of yourself every single time. There was this well-defined human being, and you chip away at it, and it just becomes this blob. That’s exactly what I felt like at the end of the two years of running KleverKid [an online marketplace to connect families with extracurricular tutors, coaches, workshops and programs for kids], where I had just followed all of these other expectations of me from ten different investors, and advisors, and my parents, and my community, and my team. I wasn’t authentic to who I was anymore. I was a mess.
From a company and brand perspective, it can really affect the entire ethos of a company, because as a leader, if you’re not being authentic, your team sees it. And there’s just no way to hide that. It’s very obvious to the team that this person doesn’t have their own North Star and they’re following what other people are asking of them, or other people’s perceptions of them. That can really influence and trickle down into the rest of the business and the brand.
KleverKid is a good example. I did not want to grow to two more cities right away, but when we raised capital, our biggest investors said: You should grow. And I sort of said, ‘You must know more, and I must not know enough. And even though this doesn’t feel true to what I think we’re ready for and what we should do next, I’m just going to do what you say, because you just gave me a bunch of money and I feel indebted to you.’ As a first-time entrepreneur, regardless of your gender, I think that this is pretty common. You don’t have that confidence yet to believe you know more. Some people may have that confidence, but I think I really struggled in that area.
The Swaddle: Your book takes apart some of your business decisions very minutely and critically. But there is a fine line between self-reflection and self-doubt. Memoirs by male entrepreneurs seem to be more externally reflective, like ‘The market just wasn’t ready for me!’ Do you get a sense of that in the broader entrepreneurial ecosystem? When it comes to self-reflection, is there a gender difference there?
SA: It’s hard to say. I’ve not seen too many entrepreneurs talk openly about their failure in either gender. We’re a group that’s a little bit nervous about writing openly about our experiences, because we’re always thinking we might start another company, and we might need to fundraise again. What happens, then, when people know that I’ve failed, know that I doubted myself?
I’ve seen a few men write openly and candidly, more internationally, coming out of Silicon Valley, about their experiences as an entrepreneur. But, it’s sort of a blame game.
I think that’s natural right after a failure, though. Right after I failed at KleverKid, I did want to blame every external entity possible. I wanted to blame the investors, I wanted to blame the market, I wanted to blame the team. And then, slowly, you piece apart this onion – layer after layer – and you realize it’s actually not any one thing that you can blame, first of all, and also that there were plenty of things you could’ve done differently.
But I do think women are more comfortable pointing the finger at themselves.
The Swaddle: Was there self-doubt in the moment, about these decisions, or did the critique come in retrospect as you were writing the book?
SA: There was a lot of self-doubt in the moment, for sure. I was very doubtful and insecure about my own decision-making ability, but the power to reflect back on why things failed, or didn’t go right, requires distance from it, and time.
The Swaddle: And it doesn’t seem like the start-up experience allows you time.
SA: Not at all, exactly. You’re really going 100 miles per hour the whole time. It’s quite difficult also, because, when you’re in it, you’re very blind to [everything other than] the product that your building and the company, so it’s very hard to also see that this could be completely wrong.
A good example of this is, for a year and a half, I was completely convinced that our revenue model was sound, even though we weren’t making nearly enough money. And it became clear that this revenue model wasn’t going to work, but I was so deeply invested, so convinced, so tied to the idea that I really couldn’t see it.
The Swaddle: You appear to have used your partner for that kind of distanced, reflective perspective – as a sounding board or gut check. How important is it to have someone in your personal life, who is not involved in the start-up, who can fulfill that function?
SA: It’s super important. It’s pivotal. If it’s not your partner, it should be someone you pay, a therapist or coach. I’m a huge, huge advocate of therapy. I think every entrepreneur, every person, should be in therapy. Or have a co-mentor. I had a friend that I had met in a fellowship program for entrepreneurs, and she and I would call each other up every week and chat about our challenges in our companies.
Because you can never be completely honest with someone who is involved in the company. I can’t tell my investor that I’m frustrated with my investors. I can’t tell my COO that we might not raise a round of capital.
As an entrepreneur, you’re never thinking about yourself. You’re really thinking about your team, your investors, your company, your product. I think I should’ve spent more time working on my mental health, my emotional health, my physical health. And if I could go back, I would definitely do that differently.
The Swaddle: There is this perception that working for a tech start-up, like yours, is so glamorous and exciting. But what you describe sounds very much like a rat race. Did it feel that way? How caught up did you get in that?
SA: The reality is, as the entrepreneur, you’re often not doing the thing you set out to do. You set out to build a product, or a service, that solves some core problem. But the day-to-day of an entrepreneur and CEOs life is much more focused on keeping the company alive. There are times where you get these windows – either you’ve raised enough that you can survive and think about the product, the business – but they’re pretty rare and few and far between. For the most part, you are in this rat race, or treadmill of just trying to raise the next round and pay the bills. It’s pretty exhausting.
However, I wouldn’t say it’s not all worth it. If you’re super passionate about the idea, and you’re convinced this idea will solve a real problem – which at the time, I really was; I still actually think it’s a good idea! – then it all still feels worth it.
The Swaddle: If you could go back and do it all over again, would you?
SA: Yeah, I would. (Laughs) I would just do it a little differently!