OPERATORS: Heidi Zak (ThirdLove) on the Leadership Skillset and Refusing to Fail

by Joseph Bien-Kahn in December 14th, 2020

Great companies start when a creative founder identifies a thorny, but solvable problem. For Heidi Zak, it was one she faced every morning while getting dressed. She had 12 bras in her drawer and not one of them fit. She had shopped for years at Victoria’s Secret — why did she have to go to the mall to buy underwear and why was it so hard to find a comfortable, correctly fitting bra?

It quickly became clear that the problem was that the market-leader was selling bras and panties to husbands and boyfriends instead of the women who wore them every day. She also realized the people writing checks in Silicon Valley weren’t convinced that women would want to buy underwear online. Zak knew better and so, in 2013, she started ThirdLove with her husband David Spector and experienced bra designer Ra’el Cohen — in 2019, a $55 million round of funding brought the company’s valuation to over $750 million.

Startup stories — even for the ones who reach ThirdLove’s success — are never without bumps in the road. For Zak, the obstacles taught her to trust her gut, actively commit to her growth as a leader, and never forget the mission. 

We called Zak for our OPERATORS series because we wanted to know how to keep focused on the problem you set out to solve, how to grow thoughtfully, and how to make the terrifying decisions that turn you from a founder to a boss. 

To go back to the start, what were you hoping to disrupt when you started ThirdLove? 

Heidi Zak: This was back in 2012 so it was a while ago now, but basically, the bra and underwear industry really hadn't evolved in 30 years. The big player was — and still is today — Victoria's Secret, and they created this idea of selling lingerie to men instead of women. Women are the ones who wear it every day and generally are wearing it to be comfortable, to look good in what they're wearing and to not think about it. So, it was really this idea of flipping the focus and trying something totally radical (I'm joking): making an incredible product and selling it to women instead of men. And then also doing it online. 

I had shopped at Victoria's Secret for twenty years, and I was working at Google at the time and going to the mall, and I was like, "I can buy everything online — why am I in this mall at a store?" This is before direct-to-consumer (“DTC”) was a term — that history didn't exist. So, that was somewhat radical and when we were pitching our seed, even early investors would ask, 'Are women going to buy a bra online?' That was one of the questions we got. That's how long ago this was.

The initial ideas are such a romantic notion in startup stories, but the true make-or-break moments often come months or years after the initial spark. Were there any specific strategies you and your founding team had to hold on to that initial focus to make sure it could serve as a kind of a motor?

Zak: What we were able to prove out within the first two years was that we could make a better product. We had this one bra that was like our hero product — it still is, it's like 30% of sales in one style, which is a lot for an apparel brand. So, we knew women love this bra. The problem was: we didn't have enough customers and people weren't trying it. So, I think knowing we had the product and knowing we had a brand that stood for something is what kept us going. But we didn't even know we were going to be successful until late 2015. So, it was three years of near-death for us. It was really bad.

Was there a plaque on a wall in the office or something to remind you: this is why we're doing this and we need to keep doing it?

Zak: Well, our mission is core, right? Our mission at ThirdLove is to help women feel comfortable and confident. And we knew we had the product and we knew we had the brand. If Dave and I had any motto it was: “Failure is not an option for us as founders.” Either I would say it to him, or he would say it to me, but we just didn't consider the fact that we could fail or would fail. We had moments — each of us individually, not at the same time — where we did say, 'Let's quit' before we raised our A. But deep down, we knew we were building something that was important for the world and going to help change the world in a small way. Somehow, we just didn't really ever think we would fail, as crazy as that is. 

That's kind of key though, right? It's such a crazy, quixotic pursuit to go start a company. So, you have to have that faith. 

Zak: Absolutely!

Was there a moment you realized that you'd gone from founder to boss? And what was difficult about that transition?

Zak: It's a very interesting question. I've actually never had that question in all the bajillion interviews I've done. No one's ever asked that. But I guess it happened when we were like 10 or 12 people. We were still early, and I do remember thinking, 'It's different now.' At the beginning, there's a bunch of you in a room — we were in a coworking space and there were maybe four or five of us in one conference room. You work that way for a while and it's really all hands on deck. Nobody's anybody, right? 

Then, all of a sudden, you have 10 or 15 people and you have more junior people who you hire, and they're looking at you like they expect you to know what you're doing. You realize that you maybe don't know what you're doing and that you haven't actually led that kind of bigger, cross-functional team ever before. So, I don't know that there was an exact moment, but it was probably sometime after we raised our Seed when our team grew. 

Looking back, if I've learned anything, it's that leadership is constant. Developing your leadership skills never ends. And then, as your company scales, if it's growing like this [moves her hand at a 45-degree angle], you need to be growing like that [moves her hand at a 65-degree angle], right? Basically, if you're scaling like crazy and you're hiring a ton of people, you better have an executive coach! Because your natural leadership development may not occur at the same speed that your company is growing. 

That's great advice! It’s so important to remember that leadership is a skillset. That it’s something you have to work on.

Zak: Totally! It's like anything. If you don't invest time and if you don't recognize your strengths and weaknesses, it can literally bring down your company. You see it all the time. Founders can be the best thing that's ever happened to a company or the worst thing that's ever happened. If you can't recognize your own strengths and weaknesses enough to understand what you need to learn, it can doom your startup. And that's why a coach is really helpful, because they can objectively identify your strengths and the areas that need growth.

Adam and Hari’s goal with AbstractOps is to outsource and simplify the back office. They like to say that it will let founders focus on their superpowers. Did you and your founding team know right away what each of you were best at? Did you have a process for outsourcing the rest?

Zak: Well, your hands are in a lot for a really long time. It takes until you raised a B where you're maybe slightly removing yourself. I mean, sure you're hiring people. But I think if you give up what you're good at too early, it's actually detrimental. But I do get what you're saying: anything that you're not good at or you're not passionate about, you should outsource or hire for ASAP. Early on, you should write down the three things that are your superpowers or the things you love doing, which tend to be the same things. 

What’s tricky is that at some point, you'll begin to hire somebody to sit in the roles responsible for the things you are really good at. Those are the hardest hires. I've seen it over and over. CMOs become CEOs and then they fire like three CMOs in a row. Sales is another one. A founder is really awesome at sales and they hire their Head of Sales and they're like, "This guy doesn't know anything." So, really understanding that if you're hiring for your core competency, you need to have a good relationship and that person needs to be open to you having input. Because if I'm hiring somebody to do something that I don't really know, then they can kind of run with it and I'm okay. But if I'm into marketing, and I hire a Head of Marketing, I need somebody who's really going to collaborate with me and bring me into the fold and answer all the questions that I have, because it's important, and I may be more involved. So, as you build your functional leaders, it's very important to understand those dynamics. Because if you don't, then you can get yourself into trouble.

That's fascinating. Looking back, I was wondering if you had one piece of advice you'd give to an early-stage founder that you wish someone had told you at that time?

Zak: The biggest thing I can say — and it's very hard — is that over time you get perspective that the little things that make you frenetic or completely stressed will be an insignificant blip on the journey of your company. But it's really hard, especially if you're a first-time founder, to not get sucked into those moments. And so, all I can say is that when something doesn't go your way or something goes wrong or the world feels like it's crashing in — which tends to happen like every other day as an early-stage founder — then you are best served by trying to have closure and move on. Because you can just catch yourself in a downward spiral. This also goes for early-stage employees, because they get into the downward spiral and it's very hard to get them out of it. 

Do you remember any specific Sky Is Falling Moments from ThirdLove’s early stage? 

Zak: Yeah, I definitely do. We were about 15 or 20 people and we hadn't raised our A yet. We had built our own frontend and backend, instead of leveraging a platform. It was a terrible idea, so we made the decision in 2015 to switch to Shopify Plus; we were one of the earlier customers on Shopify Plus and we're still on it today. Our engineering team at the time were really against it and were freaking out. They said, 'We're going to quit if you guys move to Shopify Plus,' and we basically made the really hard choice to say, 'We're moving.' They all quit and, over the course of a week, we lost half of our company — we went from something like 20 employees to 10. We were just like, 'Holy shit. This is crazy.' I mean, talk about feeling like your world's imploding. On top of that, there was the spiral effect of everybody else, even if they're not an engineer, thinking something's radically wrong. 

Reflecting back, it's one of the best decisions we ever made. But at the time, you're so worried, and you're so anxious, and you think, 'Maybe they were right,' or 'Maybe this is going to bring down the company, because people quitting will destroy the culture.' 

But it's just a moment. And you know what? We launched a new website on Shopify Plus, it stopped crashing, and it was great. It was a really good decision and we rehired different people and things were totally fine. It was a good decision. But while that was a really radical moment, there are so many things like that happen. So, my advice would be: if you make thoughtful decisions and you're patient, it all works out.