How Women Lead With Julie Castro Abrams

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TSP Julie | How Women Lead

Episode Summary:

How do women lead? In this episode, Julie Castro Abrams, Founder and CEO of How Women Lead, joins John Livesay as they talk about propelling women’s leadership forward and shifting the world’s frame. Julie shares her journey through the years from social worker to spearheading a network of women leaders and general partners in a business firm, she has done them all. Julie and John discuss the significance of having a network as they dig deeper into how Julie helps women and entrepreneurs, in general, to be resilient and find their true identity. Tune in and learn the importance of having grit and how you can get your shot to success.

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How Women Lead With Julie Castro Abrams

Our guest on the show is Julie Castro Abrams. She has a huge background in everything from being a social worker to creating her own investment firm. She gives advice on the importance of grit and you need to show grit in order to be successful as an entrepreneur. She talks about you’re not going to win everything you pitch or try to do so you must learn to be resilient. Finally, she talks about this concept of replacing your identity by telling yourself a different story. Enjoy the episode.

Our guest is Julie Castro Abrams who’s the Founder and CEO of How Women Lead. She is an expert in board governance and building diverse boards that are a strategic advantage. She is an experienced nonprofit CEO and entrepreneur. Through her consulting practice, she supports leaders to build high-performance boards, breakthrough performance for the leaders and high performing multicultural teams. She’s the Chair and CEO, as I mentioned of How Women Lead, which is a network of over 10,000 women dedicated to promoting diverse women’s voices and propelling women’s leadership forward as well as the Managing Partner of BoardLeaders, where she places leaders on corporate boards and supports them to build inclusive and high-performance boards. She’s an active investor and advisor to startups and sits on the advisory boards of FinTech startups like LENDonate and The New Search Collaborative. She’s the recipient of many awards, including the More Jobs Genius Award, the Morgan Stanley Innovation Award and has been featured in four books including Scrappy Women in Business. Julie, welcome to the show.

Thank you. I’m glad to be here.

You have such a diverse impact on the world in many ways that you inform and start things. If you don’t mind, let’s go back to your own story of origin. You can go back to childhood and school. Where did you decide that you wanted to have an impact in the world and saw some injustice happening that you wanted to be part of solving?

When I was growing up, Title IX was just passing, that was the law that said you have to spend as much money on girls sports as boys sports. I was an athlete in which the data is pretty clear that the majority of CEOs and leaders in this country, women leaders in particular have been serious athletes at some point in their lives. That was formative for me, but it was paired with some interesting things that were happening. My mom had some family money, her dad died and left her some money. She had to get my dad’s permission to spend her own money. I was around at this moment of big change. I remember when I was going to college, it was this moment when all of these guys left their wives for the 24-year-old secretary and these women were destitute. This was before there was the requirement that there would be a 50/50 split. It’s this moment in time right before an important justice was happening. I thought economic stability, women having economic power is essential to them being able to have a voice in their own families and their own communities. Those were the big influences for me that kicked me off.

I went to Northwestern University. I get into racial and gender justice in a much deeper way. I was challenged for my white privilege and all kinds of other things that were super formative for me. I spent my life designing and defining frames around how I want change to work. Early in my career, I defined this frame of a strength-based approach to poverty alleviation. When you have somebody, a woman in particular, I spent most of my life working with women, but I also worked at a music conservatory for low-income kids for seven years. It’s one of my first big job as the deputy director there. What we knew is if kids were coming from public housing, for example, in this environment, they were the violinist. They weren’t the kid from public housing. They reshaped their self-definition and it changes everything.

You're not going to win every time, so pick yourself up and try again. Click To Tweet

I ran a microenterprise and microfinance program for low-income women. I helped over 6,000 women start their own companies. If somebody is a domestic violence survivor, it’s wonderful and essential that we have emergency services that we have places for them to be in therapy, etc. If you came to my organization, you were the CEO of your own company. You were no longer defined in that space, in that moment as the domestic violence survivor. To me, that’s an essential way of thinking about how do you shift our world’s frame. As we’re dealing with all of these racial upset in this country, we need to shift the frame of who’s a philanthropist, who’s an investor and what does leadership looks like. That’s what I’m up to. We launched a venture fund. As we looked at who our investors were, the majorities were women of color. It’s first in the country. We’re all about doing campaign is like, “This is what an investor looks like. She’s brown. She’s black.” These are women who are highly educated, extremely successful and have made some wealth. They want to play a role in defining the future of our companies and what leadership looks like.

Let’s start with the impact that sports give people as a learning tool. If you’re in a sport, you learn team building. As an investor in startups, everyone who I’ve ever interviewed has always said, “We invest in the jockey, not the horse and the jockey is the team.” If you don’t have any framework of being a team player and cheering for the team even if you’re not on the field or whatever it is, you don’t have a concept of that. Let’s talk a little bit about what lessons you think people can take from sports into being a good team player whether they’re the CEO or not in a startup.

One of the other important things is you’re not going to win every time. How do you pick yourself up and try again and keep having incremental goals? That is essential as we think about, how are we incentivizing and supporting people to innovate, to take risks and move things forward.

We’re going to make that a great tweet. You’re not going to win every time so get some resilience. That’s one of the characteristics that investors like you look for in people. Tell me a story of a time you got knocked down and had to pick yourself back up and how fast did you get knocked down.

Grit is the number one thing that results in entrepreneurial success. Where do you learn grit? I learn it when I was a swimmer. I learned it in the swimming pool. It’s like you work all season. They do something called tapering where you rest for two weeks. If you’re more mature as an athlete, you finally get your best times. What if you have the flu and one day when after the whole season you finally are ready to perform and you can’t because you’re sick. What life lessons do you get with that kind of moment? It’s critical.

I’m a former competitive swimmer myself. I was a lifeguard in the suburbs of Chicago. You train and train in case you ever need to save somebody. Most of the time, you’re blowing the whistle, telling kids not to run on wet cement. When you see somebody drowning, you can’t start going, “What am I supposed to do, reach, throw, row, tow or go?” You’ve got to know it. That’s the same thing as a startup. When you’re getting up in front of an investor to pitch, you’ve got to know your story, your numbers. You can’t be grasping at straws. You need that preparation that is required to be an athlete. It serves entrepreneurs well.

TSP Julie | How Women Lead

How Women Lead: Women having economic power is essential to being a level voice in their own families and communities.


Taking off on that comment, the theory in venture is you see 100 deals and you will fund 3%, 97% of the people get told no. If you’re a woman or a person of color, you get no far more than that. It is unfair, unacceptable and I’m out to change it. In the meantime, pick yourself back up, get out there and do what you’ve got to do.

There’s a documentary out on HBO called The Weight of Gold, which shows Michael Phelps holding all the gold medals on him and all these other Olympic athletes. Who am I if I’m not an Olympic athlete anymore? They lost their identity. As you said, what if on the day I’ve been training for four years and I hurt myself or I get sick and all that perception? When I gave my TEDx Talk called Be the Lifeguard of Your Own Life!, which is all about resilience, I was fortunate enough to have the woman speak before me. Her name is Bonnie St. John. She’s a woman of color. Do you know Bonnie or know who she is? Have you heard her story of when she was in the Paralympics? She had to have surgery when she was a young girl. They removed the lower half of her left leg. She went on in her twenties to do downhill skiing with a prosthetic leg in the Paralympics. She talks about going down in two mountains. The first one, she was in first place. Everybody had to go down a second mountain. They’re going to take the average of you two times. This mountain was much icier and everybody was falling. She also fell. They averaged the times and said “You only came in second place. Why? You’re the fastest going down. In the first hill, you weren’t the fastest person to get back up.”

What a great little micro lesson of how fast we get back up. We’re all going to get knocked down again. How fast do we get back up? Anytime I get to share her story and you’re the perfect person to share it with, I love promoting her story of resilience. She’s had a lot of challenges and it keeps going. The other thing that jumped out at me was your background in music. There’s a whole connection between music and math. Sometimes women listen to music when they’re pregnant. The way music is structured fits into the way things are coded in math. I want to also say this concept of reshaping our identity, “I’m no longer my past or my color, my race or my sexual preference. I am the French horn player or the violinist or whatever it is.” At that moment, I don’t carry all the other baggage with me. How can people start to learn how to reshape their identity if they’re not in sports or not playing music? What other tips do you have for them?

It can be in anything. All of us have stories that we need to unlearn, stop listening to. Someone told you something at eight years old and for some reason, you’re still hanging on to that dumb story and it’s not relevant anymore. You need to let it go. What are you going to replace it with? We all have a choice every single day. What is your new story? You’re going to believe about yourself and you’re going to get reinforced. It’s easier said than done, but it takes focus and discipline. The sky is the limit. There is nothing we can’t do. I’m a social worker. Nobody has given me permission to become a venture capitalist, but I raised a bunch of money. I set up a structure. I’ve got an amazing team of people around me. I am the general partner of a venture fund and one of the most innovative and unique funds around now. You get to do that too. You can say who you are, where you stand on the world and whatever definitions you have that you still might want to carry with you or you might want to let go. We get to choose.

What is the name of this unique fund? I’m sure people do want to know.

It’s How Women Invest.

Grit is the number one thing that results in entrepreneurial success. Click To Tweet

You’ve said so much that’s so rich here. The focus and discipline that you get from being an athlete or a musician requires rehearsal, practice and workouts. The same thing is true for people who need to pitch to get their startup funded. If you know the odds are against you, be prepared. Practice your pitch. Don’t go in there and wing it. You need to know what they’re going to ask you about. The biggest mistake I see people make is they’re pitching it like they’re trying to get you to use their app or be a customer. You as an investor have so many other concerns beyond, “Do I want to use this app? Isn’t this cool how this works?” That’s not what you’re looking at all. Besides having a good team, would you share a couple of things that trigger you to be intrigued to go into due diligence? Remember the whole goal of a good pitch is to get the next date where you go into due diligence. What is it besides a good team that you look for that makes you intrigued to get into that, 3 out of 100 that you might want to fund?

The team is critical. The CEO is even more important. Believing that the founder has the discipline, integrity, and the gravitas that you believe. A lot of companies, you invest in them and then they pivot, and they’re a new company by the time you end up having an exit. Do you believe that this leader has the mental flexibility to be able to pivot? There are other things that you look at. I look at, is there an exit strategy that I can see? Can I see a 10x return? Some people will have a nice business that shows every year, moderate growth. If it’s moderate growth, you’re not a venture capital candidate necessarily. We’re looking for someone who could scale up quickly and then has a very large market, we call it a TAM.

Can I identify at least $500 million in the market for you? We all think we are and have the most unique thing ever. Being honest about what is in your competitive landscape, we need more than one of everything. You don’t have to be the only one. Be honest about it and be clear about how you’re differentiating it. If you can’t be honest with yourself and with us about those kinds of things, we’d see through it, and we don’t necessarily trust you. How are you going to exhibit both, all the technical stuff, have a great pitch deck but also show us that you are both responsive, honest with yourself and with us about what’s the real deal? Some people are so fake and you’re like, “I can see through that a mile away. I wasn’t born yesterday.”

When you lose trust, you lose everything. That’s why the due diligence is key that you haven’t said anything that they’re going to find out about in due diligence, where they go, “The deal is off because you lied to us about something.”

That has happened to me before. I ended up contacting a company that someone said was their beta test and they were going to have a big contract. When I contacted someone I knew in the company, they’re like, “No, we told this person to take us off their pitch deck and off their website. We’re not going to work with them again.” It was like it will never touch her with a 10-foot pole now. It was too bad.

I’ve heard investors say, “If you don’t have competition, you don’t have a market.”

TSP Julie | How Women Lead

How Women Lead: Venture capital is important and a good resource for lots of people, but it doesn’t have to be the right thing for everybody.


Maybe. There’s something called a Blue Ocean Strategy like Airbnb didn’t have real competition. It was hotels, but by the end of the day, Airbnb markets are so much bigger than the hotel. It created a whole new marketplace. That doesn’t happen very often.

During a pandemic, they’ve closed down all the public pools and even the condo pool I live at. There’s a company called Swimply, have you heard of this?

No. I’m a swimmer. I need to find this.

It’s the Airbnb for swimming pools. People who own their homes and have a private pool, you go on the website, you look at all the pools in your neighborhood and you say, “Click. I want to book from 10:00 to 11:00 and swim for an hour.” You send them the $45 or $60 or whatever it is, depending on how fancy the pool is and you never even see the person. They unlock the gate. You bring your own towel or you can have a little swim party for up to ten people. This is a genius of an example of taking a concept and having it work. Even if you don’t have “a lot of competition,” you’re that cutting edge, I do think you need to be able to express your secret sauce. That is where a lot of people don’t realize how important that is. It can’t be duplicated by a bigger company with more money and the ability to do that. Do you have a story of a favorite startup that you’ve funded that had a great secret sauce that made you go “That’s going to be something?”

This is something that’s very near and dear to my heart and just happened. I ran this microfinance organization and helped thousands of women start their own companies. One of them was a woman who is a domestic violence survivor from Malaysia. She grew up in a family of street vendors, which is the lowest of the low in the societal structures in Malaysia. She came to the US and escaped the abusive marriage and started cooking Malaysian food. We helped her turn it into a formal business. The Obama’s had dinner. We had her cater something. They ate her food. They came back two additional times during the time that they were the presidential family. I had a birthday and my daughter said, “I’m going to bring you dinner.” She brought me Azalina’s, this Malaysian food, which is so fresh and so good. You can’t find it anywhere.

I said, “How do you even know about her?” My daughter works at Uber. She’s the chief staff of the design team. She said, “Mommy, we partner with her for Uber Eats. We have a video of her all over our company all the time. I buy from her all the time. It’s my favorite place to go. She’s been in the Twitter building on the bottom floor.” It was one of those things where it’s like, this was a fifteen-year journey. I haven’t talked to Azalina for a couple of years and here my daughter brings it to me for dinner. She’s got a cool product. She’s doing great. She’s scaled and ramped in. A lot of people know about her. To me, that was one of those things where I was like, “I knew her at the beginning of this journey and how beautiful is that?” It’s a very big company now.

Everyone has stories that you need to unlearn. Click To Tweet

It’s a play on words. It’s the secret sauce of what’s in the food and then the secret sauce of what makes your business so successful.

I have dozens of stories like that. There’s this woman from Australia. She came to the United States. She didn’t have a community. She was trying to figure out how to make a living. She started baking scones. She took me to the farmer’s market. She happened to come in the wettest winter that we had. Scones and water aren’t such great bedfellows in the farmer’s market. She was outside. She came to us. We helped her figure out how to put a business plan together, ultimately open up a location. She had this shtick she decided to do to get people to recognize her. She calls herself Bakesale Betty. Her real name is Alison, but hundreds of thousands of people know her as Bakesale Betty. She puts on a blue wig and wears this ‘50s outfit.

Her tables in her restaurant are old fashioned ironing boards. She’s created this whole shtick and she doesn’t do any marketing. It doesn’t even have signage. She puts butcher paper every morning that says Bakesale Betty’s on the window. The way you know about her is through word of mouth, or you see the line around the block. Every minute they are open, there’s a line around the block. They got one of the handfuls of contracts at the Chase Stadium that opened up. It is a great example of someone who is like dying in the vine there because financially in a million ways. She became very famous.

What you just said is something I love. It’s called the rags to riches story. That’s a storytelling genre that I teach people in my course when they want to learn how to sell better, whether it’s to get a startup funded or get new clients or customers. We have the image of her in the water, the rain, the scones and the farmer’s market. I spoke at the Coca-Cola CMO Summit. One of the people in the audience was the marketing person for Auntie Anne’s Pretzels. They’re sold in malls and airports. I said, “How did this company start?” He said, “She sold pretzels at the farmer’s market.” Now, look how successful it is. It’s that same journey.

TSP Julie | How Women Lead

Scrappy Women in Business: Living Proof that Bending the Rules Isn’t Breaking the Law (Scrappy Guides)

For everyone reading, think about what your story of origin is and what genre of the storytelling it is. When you have that going for you, you can pull people in. Everyone’s going to remember that story. What’s fascinating about that story is you don’t have to have a multimillion-dollar budget like Apple to have people stand in line to get your products. People think Apple is doing something right. They’ve created an emotional hook. What your friend, Bakesale Betty is doing, is creating ironing boards as tables. We crave new things and that’s why stories and visuals make something memorable and pull people in. This has been so much fun and interesting. Do you have a last thought, quote or book you want to recommend to anybody as we say goodbye?

If you’re thinking about starting a company or you have a company, and you’re thinking about getting venture funding. I like people to first read the book, The Founder’s Dilemmas. Be careful what you wish for because as a venture capitalist, we get to own part of your company. We get a seat on your board. It has happened with some frequency that people get fired from their own company that they founded for bad reasons and good reasons. It might have been appropriate that Travis Kalanick at Uber was asked to leave because there was some bad stuff going on there. It often happens that you don’t manage the dilution well. You can end up not making any money. The company can make huge money for its investors. Be careful before you start giving away your baby. There are lots of loan products and lots of other ways to grow and being disciplined about what you spend. Venture capital is important and as a good resource for lots of people, but it doesn’t have to be the right thing for everybody.

If people want to follow you, read more about you, what websites should we send them to? is our big network for 10,000 women leaders and is our venture fund. You can find them both on each other’s websites.

Julie, thanks again for sharing your passion, your wonderful stories, not only your own stories but about other women you’ve helped. We’re all inspired now. We have some great tips on how to tell better stories.

It’s my pleasure. Thanks for having me. Thanks for all you’re doing.


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Tags: Athlete And Entrepreneur, Grit And Resilience, How Women Lead, Women Entrepreneur, Women In The Corporate World, Women Leaders

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