Willow Spotlight: Alex Lebenthal on the Power of Female Entrepreneurship & Mentorship

A passionate supporter of women in business, Alex Lebenthal is a legendary woman of Wall Street. She was named one of New York’s 100 most influential women by Crain’s New York Business, one of the top 50 Women in Wealth Management in 2009 by Wealth Manager Magazine, and included in Crain’s New York Top Women Owned Business list in 2011. She is a frequent commentator in the media.

After a storied career on Wall Street, Alex noticed that women founders weren’t building relationships with their investment bankers at the same rate or depth as male founders did. So she decided to change that.

She currently leads an initiative at investment bank Houlihan Lokey to support female-led and female-founded companies to develop those key banking relationships. This in turn helps women better scale and grow their businesses and be better prepared for an exit strategy. “It’s tremendously exciting,” she told Willow, “to be at the culmination of much of what I’ve done over my own life and career.”

We sat down with Alex for an exclusive interview, where she shared her insights on topics like:
  • How women can support female entrepreneurs
  • Why it’s important for women to be financially savvy
  • The personal finance advice she’d give her younger self
  • How women can better advocate for themselves (and what she’s still working on herself)

Read the condensed and edited interview below, and follow us on Instagram for exclusive video clips from our interview.

How the role of women has changed in the workplace and the boardroom

When I look back to when I first started working in 1986, a great amount has changed. There are women who are running huge businesses at banks and at companies. The number of women in the boardrooms, certainly over the last 5–6 years, has grown significantly too (there is still more room to grow, though).

One of the things that I noticed, which to me is tremendously exciting, is there’s an understanding on the part of the men who’ve been running things that it can’t continue. They recognize the need for change. They don’t necessarily know what the answer is! But the fact that they are recognizing this is not okay, and that we need a lot of different voices to shape the new dynamic going forward is perhaps the most significant change in the right direction.

It used to be women banging on the door to be let in, and knocking it down. But how different and wonderful it is when you’re getting to the door to knock it down and somebody says, “Hey, come on in! We don’t necessarily know what to do when you get here, but we can figure it out together.”

Two ways we can use our collective power and influence to support female entrepreneurs

I’m so excited about how female entrepreneurs are changing so much of the way we live and function. One thing I’m super excited and totally intrigued by is the whole FemTech world. Many young women have said, “I don’t want to have to be secretive about doing things that are a normal part of being a woman. So let me create a new product and way of doing that.” I mean, that’s tremendous. That’s even changing the landscape for the older generation of women.

Two ways we can support female entrepreneurs:

  1. Buy women-owned: I cook with many things that are women-owned, and I even started purchasing toilet paper at CVS that’s women-owned. So being conscious of buying products that are from a woman-owned company is a way that we can definitely continue to make our voice heard through the power of our wallet.
  2. Invest in women: There has been an enormous explosion on the part of female angels and venture capitalists looking for female-founded companies. You do need a certain amount of money [for direct investment], so that’s not necessarily something everyone can do. But with Robinhood or other platforms, you can find women-owned companies, either through an ETF or individual stocks, to invest in.

The most surprising thing about female entrepreneurs

It’s something I’ve seen so many times: no matter how successful the woman is, invariably, she will always make time to help other people and other women. It’s just how she functions. Rare is the occasion when I’ve encountered a woman who wasn’t willing to help.

I think that every woman who’s successful recognizes that it was a lot harder for her to get there than it was for her male counterpart to get there. So when she sees other women encountering those same challenges who are a few years or steps behind her, she’s able to say, “Yes I will help you. I want to move you along, because I know once you get here, you’re going to do the same for the ones behind you, too.”

Why her grandmother was one of her most influential mentors

My grandmother started our company [Lebenthal & Company] in 1925 and worked until she was 92. I worked with her when she was 91 and I was 23. I didn’t think of her as a mentor at the time because I’d grown up with her.

But as I became more senior and a CEO, and even in the last several months, I’ve realized more and more what a mentor she was to me. Because of seeing her and hearing her talk about barreling through regardless of obstacles, I realized I learned that whatever rules and limitations women feel they have, I always felt like those rules didn’t apply to me, which I think enabled me to move forward and bring others along the way with me.

I wish that more women and girls didn’t feel like there is anything that should be holding them back. There are so many amazing women—we just talked about Whitney Wolfe, Founder & CEO of Bumble—and so many companies, that there are enough role models to show that you should not be held back.  

How women can better advocate for themselves

Make sure that people know what you’re doing and know your achievements. Women can sometimes assume that it will be like it was in school, where the teacher will say, “Well, I know Alexandra knows the answer,” and they know how smart you are.

It doesn’t really work that way. You have to be able to say, “Hey, I did this, I made this happen, I have this relationship.” The important thing though, is to do it in a way that really fits your own personality. If I just walked around saying, “I brought this account in, and it wouldn’t have been successful if not for me,” that would not fit with my personality. So it’s about ensuring you find an authentic way to communicate what you have done.

The area where I think I sometimes fall down on the job is ensuring that you get credit for it. It’s one thing to say, “I did it and everybody knows it” and it’s another to then say, “And therefore you should give me XYZ.” Usually with a dollar sign in front of it!  

Working with a coach as a 31-year-old CEO

Working with a coach was a very meaningful experience for me. Here I was, the third generation of a family business with a larger-than-life father, and made CEO at 31.

I felt, “I guess I’m supposed to know all of it, now that I’ve been put in this position.” And at the same time, I felt insecure because I didn’t know everything. But I ended up pushing ahead and making a couple of decisions that were actually very contrary to who I was as a person, because I felt like, “Well, this is what I’m supposed to do.” It turned out to be a full-fledged disaster.

At that point, I realized I better go out and get help. Because this is not going to go well if I don’t figure out how to be a leader while being me at the same time. So I worked with a coach. She was so great in helping me understand my personality traits and how that translated into leadership.

She was also really helpful in giving me perspective on how to deal with people who were older and more experienced around me. So I think it’s an incredibly valuable thing to have, if only to understand who you are and why you operate the way you do.  

The personal finance advice she’d give her younger self

Both personally and from a business perspective, I would advise understanding debt and its impacts. There are times when you can’t avoid it, and there are times when it could actually be beneficial to you, but understanding the cost of borrowing is so important.

For example, I don’t think we spend nearly enough time talking about credit card debt. Or teaching young kids about what that plastic thing is that seems to get you whatever you want. Teaching what that interest really is and how that compounds and builds every month is so valuable.

On the business side, when you’re building a company and you believe in it, you’re going to do whatever you need to. But knowing what debt can do to a business—in terms of the interest costs, the structure of the debt, whether there’s a personal guarantee—that’s crucial.  

Why it’s important for women to be financially savvy

Women who are divorced or widowed are often trying to figure out how to manage money or even have enough money to function. So it’s crucial to have that education and empowerment—things like, ensuring that you’re conscious of what you’re doing with your money, spending thoughtfully, having money to save and invest, understanding the long-term power of compound interest and tax-deferred investing, and understanding what all of that means for you.

That means not just understanding facts and figures, but also what it means for you to be able to live your life and your dreams and goals that you have for you and your family.

Over the course of my career, I’ve spent a lot of time working with women and talking to female investors. And the thing I can’t figure out is why girls and women grew up somehow feeling like money wasn’t a topic that they were supposed to know or understand or be involved in. But the sooner that a girl develops financial literacy, that’s the making of a successful investor, of a successful business woman, and of a woman really feeling like she can do anything that she wants to.  

Note: The views and opinions expressed in this article are those of the subject and do not necessarily reflect the opinion or position of Willow.