When Anu Duggal returned to New York City eight years ago from India, the two-time founder and angel investor was shocked at how little venture capital was going to female-founded companies in the U.S. Duggal set out to bridge the gap by creating the Female Founders Fund. At first, the going wasn't easy; Duggal estimates it took her more than 700 meetings to assemble a $5.85 million early-stage investment fund--but she has since raised $27 million for her second fund. F3, as it's known, has invested in everything from highly valued consumer brands like wedding site Zola to upstarts like Tala, a mobile-based personal lending platform for the developing world.

Mentee Rhian Horgan knows finance from both sides. After her family emigrated from Ireland when she was a grade-schooler, Horgan went on to pursue a degree in finance and public policy and make her career at J.P. Morgan. When it was time for Horgan to help her parents retire, she found herself trudging through a 300-page tome on Social Security. "I thought to myself: This is crazy," she says.

After 17 years at J.P. Morgan, Horgan set out to create Kindur, a retirement advisory platform that acknowledges Boomers' digital literacy, 300-page doorstops be damned. Two years in, the 18-person, New York City-based startup has raised just over $11 million to help retirees manage their income and make sound financial decisions. Members can use Kindur's online toolkit to calculate retirement budgets and compare options for insured fund management. The platform oversees their retirement portfolios for them and even sends them monthly "retirement paychecks."

But Horgan's platform is only as good as the trust it inspires. Thankfully, Duggal is no stranger to getting people to put their money behind something new. --As told to Christine Lagorio-Chafkin

Horgan: Kindur was founded around the question: How do we help the modern retiree, who's really excited about living in retirement? For retirees, there are a lot of big, one-time decisions that have huge financial consequences: when to take Social Security; what to do with their multiple retirement accounts.

These are all new decisions--and taking Social Security at 62 versus 70 could mean a difference of $200,000. We think a lot about how to get the customer the right information and help them build confidence in making this decision that they can't really reverse.

I'm so curious: When you look at your portfolio com­panies, which have had to really build trust around high-consequence decisions?

Duggal: We are investors in a company called Tempest, a holistic platform for alcohol addiction. Ten percent of the people who go through the program become educators themselves. It shows that when people are really experiencing value from something, they want to share it. You can harness that.

One of the most powerful parts of what you're building is that there's an opportunity for the customer to also be the educator. Hiring people who are in your target demographic who can speak the language of someone their age or socioeconomic background can be really powerful.

Horgan: Yes! There's also a lot to be said there around what this more flexible work econ­omy is giving to this demographic. How do you harness the Boomer workforce? It's a great question.

I'm seeing conversations like, "I figured out Medicare, and I want to help you figure out the tricks too."

Duggal: How you build trust with your demographic is really important.

Horgan: It's precisely what we're working on two years in. We raised our seed round two years ago, hired a CTO, met with 40 insurance companies to find one that would build a no-commission product for us, and hired a general counsel. Now that we have built the right financial product for our customers, we are finding the best way to connect with them.

Duggal: I guess the question about finding customers becomes: How do you get interested people to convert in a way that is meaningful? So I'm curious: How are you guys thinking about that conversion process? Maybe I can offer some insight there.

Horgan: We use a lot of channels that you would expect people to use for slightly younger demographics. Facebook is our most successful channel. It's really wild to see how engaged this demographic is with one another. We advertise on Facebook, and then you see communities being built to answer one another's questions. We've decided not to insert ourselves, but rather to let it be really organic, with people who have cropped up as the "Medicare expert" and the "Social Security expert."

Still, it's really hard in a digital-only experience to get all the facts across. We can do a lot in a series of online FAQs, but does that really have the authenticity they are looking for? The peace of mind?

Duggal: If there is an opportunity to sponsor or host events, that could be really powerful.

Ultimately, the biggest challenge is, how do you gain trust? I think people want to hear about it from their peers. I'd do branded marketing, host cocktail hours--even in retirement communities.

And they've got to be seeing it everywhere: online, in retargeted ads, in person­--whether it's on billboards or TV, or even in mailers.

Horgan: A lot of the imagery that's targeted typically to this demographic is about life diminishing. It's about hearing-loss prevention or cutting back on spending. We're about more than just getting you through retirement--we're also about helping you live a full life through retirement.

One of the things that we really think a lot about is how bold we can be without risking people's trust in the brand. From your portfolio, which company is the boldest in its marketing and adver­tising, and how does it work? How edgy can we afford to be?

Duggal: Oh, definitely Billie, with its Project Body Hair. It showed pubic hair. It was like, "There's a first time for everything." You need to reset the norms and use that as your starting point. When you're targeting people in their 50s or 60s, that's very different than targeting someone who is 85.

You could tell real stories of peers from this generation doing amazing things--Maye Musk, for example, is still modeling and working phil­anthropically. I also know a woman in retirement who stumbled into Broadway and screen acting. This is what she's doing in her late 60s.

Horgan: I have a question: When would you hire HR?

Duggal: It depends on the company, but usually around the time you'd raise a Series B, or have about 40 to 50 employees. What does your hiring strategy look like?

Horgan: When I hired my CTO, I knew we'd had a meeting of the minds--but I couldn't tell if his code was any good. That's when I began leveraging the advice of our investors and advisers who had those bits of information I did not.

I've done the same every time I've hired someone for a different role that I don't have experience in. And now I have a whole network of other CEOs and experienced people to speak with and go to when I face a new challenge.

Duggal: And if you do make mistakes--just have the knowledge that nobody makes all the right decisions when it comes to hiring. That can be very comforting.

Finding and Funding Women-Led Startups

Anu Duggal has raised over $33 million from the likes of Anne Wojcicki, Melinda Gates, and Whitney Wolfe Herd to support the 37 female-led startups in her Female Founders Fund, including these buzzy consumer brands.

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Billie: Georgina Gooley's D2C shaving company uses unabashedly honest marketing to defy the "shrink it and pink it" convention for selling female products. 

Eloquii: F3's first big exit was the chic plus-size clothing company led by Mariah Chase, which sold to Walmart for a reported $100 million. 

Primary: No sequins, logos, or scratchy tags--Galyn Bernard and Christina Carbonell's kids' clothing company is projecting over $50 million in sales this year. 

Kin Euphorics: Jen Batchelor's alcohol-free herbal libations are chock-full of hibiscus, orange peel, and other herbs to help manage stress and support cognition. 

BentoBox: Designer Krystle Mobayeni created a platform to manage restaurants' online presence. This year, her company reached No. 305 on the Inc. 5000.