Q&A: More Women Investors and Founders See Opportunity in the Caregiving Economy

Lisa Burton O’Toole, vice president of HearstLab, has two key pieces of advice for women founders. They both center around action.

First, “make the ask,” she says — of mentors, accelerators and your network. Ask for what you need. And second, there’s never a “perfect” time to start a business, so stop holding out.

Times of E reporter Skyler Rossi spoke with Burton O’Toole and HearstLab brand marketing fellow Michael Maerlender Sept. 29. 

The New York City-based Lab supports women-led startups. Its portfolio of 37 founders is 100% women-led and 41% founders of color. Burton O’Toole and Maerlender wouldn’t disclose details about the fund’s performance, in accordance with HearstLab’s policy.

Burton O’Toole was accepted to the HearstLab program in 2016 as a founder of marketing and advertising startup AdMass. But after her time there, she fell in love with the accelerator side of entrepreneurship. “The idea of helping so many different founders was very exciting,” she said. She’s became vice president at HearstLab in 2017. 

Responses have been edited for conciseness and clarity. 

What works best for supporting women the way that they’ll succeed?

Burton O’Toole: Key commercial deals go a really long way. So that’s a big focus for us, helping companies get some of those initial big contracts to get the flywheel spinning. I think it’s also important to have a really diverse network around you to be able to get help with everything from engineering to customer service to hiring. And I think that the founders I see as the most successful in leveraging programs are the ones that make really specific asks. We can usually infer what people might need. But I would say making the ask makes it so much more efficient and effective for us. And I think that goes not only just with our program, but with any founder that is looking to leverage mentors and sponsors around them.

What would you say is the largest barrier that women face as they grow their companies?

Burton O’Toole: Our whole investment thesis is that diverse teams are better to invest in. You see higher returns, you see faster exits from these teams. So I think there’s an opportunity there and not enough people see it. But you know, that is to our advantage. …  If you look at our portfolio compared to others that are at a similar stage, we’re outperforming the market average. And I think it’s because of that investment thesis that diverse teams, diverse founders, build diverse teams, and diverse teams build better products. So they’re thinking about the customer and the user in so many different ways, because there’s those different perspectives, thinking about the problem and the product. So of course, then it’s going to appeal to more people, you’re going to have better sales, better appeal, better engagement. And we see that in so many different industries across our portfolio.

Do you think we’ll ever get to a point where women are getting an equal share of funding? And if so, what might need to happen in order to get there?

Burton O’Toole: I am a hopeful person. So I say yes to that. I think it’s a long path to get there. But we’re seeing, again, more and more (people) focused on this, which is really important.  Of course, writing checks to women-led companies is a big part of it. But I think there’s a lot of other support systems that will help this move more quickly. There’s so much focus right now on the care economy and caregivers, and how the pandemic, especially, has disproportionately affected women. And I think many female founders that were balancing, taking care of parents or kids or other loved ones and careers have been put under even more strain than some of their male counterparts. So there are some exciting potential legislations in play. And there are real pioneers, and people — Melinda Gates is doing great work in this area — to help figure out different ways to support caregivers. And I think that will have a huge impact on seeing more women founded companies, women founded companies that are funded and successful. Let’s see.

Maerlender: Also if I may add, I think just sharing the success that we’ve had so far, and really proving that this is not just about social equity, but it is about good business. And proving that, you know, there are so many talking points that naysayers are trying to bring up , (saying) that it’s just for social good. And maybe it’s not good for business. And we are directly staring in the face of that and saying that’s not true. … I think people will feel more compelled regardless of their personal convictions to join us.

What is your advice to women founders who are getting started building their company?

Burton O’Toole: It’s interesting to hear a lot of our founders talk about their process of starting a company, because I think many of them went through a long period of waiting for the perfect time to do it. So let me wait until I get this promotion, let me wait until I have a certain amount of money saved up or I’ve finished this project, I think there’s never a perfect time to do it. So to not necessarily wait for everything to fall in line, but to make the jump. If it’s a problem that you’re thinking about solving day and night, and it keeps you up, and it gets you so excited to work on it, make the jump and do it. And that’s the best way to just dive in: Feet first, and indeed, go on with the company.

This story was adjusted after publication to correct Lisa Burton O’Toole’s name and the date of her promotion, and clarified to reflect the length of time she was at the accelerator; and that it was not the individuals’ decision not to reveal investment results, but rather the company’s policy.