WORKWEEK

With only 24% of leadership roles in financial services held by women, we still have a ways to go to achieve gender parity at the top.

However, some women have been in the game & holding the door open for decades.

Liza Landsman, CEO of Stash, among them.

This is her story.

Liza is an inspiring innovator, powerhouse operator, and esteemed VC investor all wrapped into one. 

The choice to bring her on as Stash’s new CEO in February of this year was a no-brainer. 

And like many of us, Liza didn’t start out in fintech, rather she found belonging through a series of fortunate events.

Early in her career, Liza started out working at a literary agency. But she soon caught the ‘digital bug’ and made a career move to working in deep tech. 

She had a lot of friends during that time who worked in finance, and at first she totally did not get the hype. 

She thought, boring Wall Street types in suits and heady financial jargon? Not for me.

After a while, she decided to get a job working at Citi, believing it would be a good gig to have while raising her young children. 

Then something unexpected happened. 

She discovered behavioral economics and started to get really compelled by the notion that the way people spend, save and invest their money is in fact the purest expression of their values. 

This fascination turned what Liza assumed would be a short sprint in finance, into a marathon. 

After working at Citi for ten years, (8 years longer than she expected to), Liza went on to lead as: 

• Managing Director of Digital for BlackRock Global 
• Chief Marketing Officer at E*TRADE Financial 
• President of Jet.com 
• General Partner at New Enterprise Associates (NEA) 
• A SquareSpace Board Member 

And now, Chief Executive Officer of Stash. 

In my podcast interview with Liza, I asked her why she left the TradFi sandbox to play with the cool kids in fintech (cause let’s be honest, that’s where access is happening). 

Liza shared with me that after working in executive leadership in several different prominent financial institutions, she began to see the cracks in the larger operation. 

Liza observed that structurally, all of these businesses were set up to serve the mass affluent extremely well, while the vast majority of households that didn’t meet that criteria were left dramatically underserved and with so much less made available to them. 

This logic never made sense to her.

She saw what small scrappy tech companies in other categories were doing to push the envelope in terms of access, and was ready to truly yield the power of technology as a disruptive force in finserv.

So when Stash called, Liza gladly picked up the phone. 

Stash promotes an easy way for anyone to get involved in the capital markets by investing a small amount consistently over time in a diversified portfolio. 

The app now has over six million customers, and manages $3B in assets. Tell me again how direct-to-consumer fintech is dead? 

Because it seems alive and well to me. 

Beyond the economic proof that this type of investing works, Liza fell in love with Stash because its model also psychologically understood investor behavior. 

She explains that Stash’s founders modeled the fintech after Weight Watchers, understanding that as humans we easily get overwhelmed by major changes in our behavior–especially anything that feels restrictive. 

Just like Weight Watchers breaks down the idea of losing 30lbs at once to just losing 1lb at once for its users, Stash proposes that you don’t need $3000 dollars to invest, but rather as little as $5. 

Stash does the work for its customers of constantly rebalancing its Smart Portfolio based on market conditions, so all investors need to succeed–truly–is to invest a small amount of $ over time. 

With Liza as CEO, Stash and its core mission are in excellent hands. 

Beyond sharing her incredibly impactful story, Liza also dropped some serious wisdom in my conversation with her that all of us looking to lead and innovate in this space need to hear. 

Let’s cover some of the highlights. 

1. Doubt is for other people 

When I asked Liza about navigating doubt, her response was when you are part of a leadership team of a startup, you shouldn’t let doubt in the room. 

Yes, there should be space for intellectual curiosity, but “if you don’t have complete conviction in the mission of your business, you probably should invest your time elsewhere.”

2. Hope isn’t a replacement for planning 

Liza believes there is nothing more hopeful than creating a product you honestly believe will make the world a better place for you and for others. 

However, she warns that hope isn’t a replacement for sincere planning and intention. 

“Give people a plan and a set of actions to do that lead them to that better future, don’t just hope for it.”

3. I repeat: Consumer fintech is not dead

As long as we believe that consumers are going to want to buy and sell stuff in order to have money later in their lives–no matter what the capital markets are doing–then this criticism will remain a fallacy. 

There are billions of underserved people who don’t have access to financial services–the power of fintech is its ability to bridge this gap. 

Case closed. 

4. It’s always easier to be cynical than it is to be aspirational

The scarcity mindset is deeply ingrained into all of us. 

Why? Because it’s fundamental to our culture’s ability to keep people afraid of what is possible for ourselves. Especially those of us historically left out of opportunities to build wealth.   

Liza confirms that one of the biggest obstacles to getting people engaged in investing, is overcoming the initial ‘fear of the dark.’ 

People don’t invest in their retirement because they don’t intellectually understand the benefits, more likely they refrain from investing because they:

1. Don’t have the money and therefore are afraid they can’t afford it
2. Don’t know how to do so properly and are afraid they will look stupid or make a mistake 

Direct-to-consumer fintech companies are responsible for finding the right way to lead the public safely into the dark, so we can begin to turn on the lights. 

5. Keep snowballing women into the room, because its working 

When I asked Liza about the challenges of being a woman in this space, she said “It’s not as good as it could be, but it’s far better than it was, both in terms of representation and just openness.” 

Though it’s a slow painstaking process, each woman who breaks through that glass ceiling creates more momentum, and leaves the window open for others to follow. 

6. Don’t concern yourself with critics on the sidelines

With all the obstacles ahead, particularly for women, Liza emphasizes the importance of only listening to those who actually have skin in the game and are participating in the process of making our economic system more democratic. 

She’s not interested in the opinions of those criticizing her from the sidelines, and we shouldn’t be either.