This article originally ran in Term Sheet, Fortune’s newsletter about deals and dealmakers. Sign up here.
Upfront Ventures partner Kara Nortman is innately curious.
It’s why she listened to Tinder’s Sean Rad when he told her he had a dating app idea. It’s why she constantly asks her portfolio founders to evaluate her effectiveness. It’s also why she has a Gen Z mentor.
Nortman, who has been a founder, an executive, and a venture capitalist during her career, regularly consults with a 21-year-old tech entrepreneur to better understand the Gen Z demographic.
She casually mentioned this to me during our 30-minute conversation. “It started just because I wanted to be helpful to a young woman who I knew was talented,” Nortman said. “At some point, I realized I was learning more from her than she was from me. It constantly reminds me not to be ageist or industry-ist.”
Nortman’s mentor Tiffany Zhong told Term Sheet that they talk about everything from the personal (should Nortman get her kids smartphones?) to the cultural (do not use excessive hashtags on Twitter) to the professional (discussing the psychology of a teen consumer).
In a conversation with Term Sheet, Nortman discusses her career trajectory, what she looks for in founders before investing, and why she thinks empathy is a competitive advantage.
TERM SHEET: You were only 24 years old when you first served on a company’s board. You’ve said that a high EQ made up for your lack of experience. What did those early experiences teach you about being an effective board member?
NORTMAN: I got my first two board seats when I was 24 and 25. In one of them, I was doing everything. I was literally given the instructions to go in there, fire the CEO, make all sorts of changes, and make sure it survives. I had never done any of those things before. Very simply, I applied the golden rule of “Treat others the way you want to be treated.”
So you go in and you look at the income statement, figure your what the burn rate is, figure out what the revenue is, and figure out how to extend it and survive. A lot of it is about listening and having empathy, which is stuff that didn’t always seem like a competitive advantage. In the last year, it seems like it is.
How has empathy become a competitive advantage in venture?
NORTMAN: I think a lot of people in venture think that being kind and being tough are mutually exclusive. I actually believe that when you figure out how to put those things together, you are the most effective. Start with a compliment before you tear in to someone. Once you’ve been tough with someone, give them some hope.
I experienced this when I worked for [IAC/InterActiveCorp Chairman] Barry Diller. When he had lost faith in you, there was no more yelling. There was just silence. Anyone who spends the time to be tough cares, so how you wrap that present and deliver it is what actually makes the impact.
Speaking of IAC, you were the executive who recruited Sean Rad & gave him his first business plan. What did that initial business plan entail?
NORTMAN: Sean had already started two companies in L.A, and I had some really strong references on him. It was not easy to recruit founders into IAC because the equity they would receive was tiny compared to what they would do on their own. But Sean and I hit it off, and he had just come out of a hard startup situation, so he was looking more for purpose and connection than money at the time.
The original plan when I recruited him was for a company called Cardify, [a local rewards program.] I did it to save CitySearch [a city guide] because CitySearch was one of the businesses that I was running at IAC. Its data set was corrupted, and all these things were going on with it.
We were essentially going to build a loyalty product — the Uber for loyalty. It would use location data and know that a person showed up to the same restaurant, and the next time they showed up, we’d just say, “Oh we already have your table reserved in the corner.”
And then Sean came in and said, “Hey, I can use the exact same backend tech to know that one person showed up at a Clippers game one night and another person showed up at a Lakers game, and they’re one step removed on Facebook — maybe they want to date.”
It was pretty controversial at the time because this was being incubated essentially out of CitySearch, and there were two other projects being incubated out of Match and out of corporate that were trying to do the same thing. It was this covert, quiet, like “Why is CitySearch incubating a dating project” type of thing.
You’ve invested in companies like Qordoba, Strive Talent, and Parachute. What are the key elements you look for in a founder before you invest?
NORTMAN: When I started in venture capital, I made a checklist so I could try to be as structured as possible on this because I’m an optimist and I get incredibly enthusiastic when somebody inspires me. My checklist is vision, domain expertise, and a really big one for me is — are they in it for the right reasons? Are they a natural leader who can balance conviction and constant learning?
To flip it, what are some elements founders should be looking for in VCs before deciding to partner with them?
NORTMAN: I think it’s different at different stages. At the institutional seed or Series A stage, it’s about the psychology of the founder. In the process, are you anxious every time you’re talking to the investor? Do you walk away from conversations feeling inspired or energized or nervous? Do they say what they’re say going to do? Just the very basic question of how do interactions with this person make me feel is so important because it’s never better than when you’re being courted. It’s only going to get worse, so if you’re not feeling great at the beginning, it’s going to get worse.
Many founders think that VCs are great for helping with introductions or recruiting, and they over-prioritize those things. It’s not about how many introductions you make, but about how helpful those introductions have been to the founder. I ask my entrepreneurs all the time — ”What’s my batting average? How many of the people have been useful and how many have completely wasted your time?”
You recently tweeted that 50% of the companies in your personal portfolio are led by a female CEO. Industry-wide, though, female founders received 2% of all venture funding last year. What needs to happen for this stat to change?
NORTMAN: We need to get more women into venture funds. You come into a partnership, you see a female face, and you have someone you feel you could reach out to.
Another one is really pushing yourself as a VC — men and women included — to look at the world and recognize there’s a huge advantage to funding people who are of different ages, different stages, different places, and different parts of the world. Think about the people come in and pitch your partnership. Think about the way you manage communications. Think about how much it requires for an entrepreneur to pitch you exactly the way you want them to.
You are part of the group of 34 senior female investors who created All Raise, a nonprofit organization dedicated to diversity in funders and founders. Why do you think an organization like this needs to exist in VC today?
NORTMAN: It grew out of a dinner series [Cowboy Ventures partner] Aileen Lee organized in 2017 as a way for us to look forward. But this wasn’t a dinner group that sat around lamenting the status quo. From the beginning, we focused on driving concrete programs to increase the percentage of female venture-backed founders from 15% to 25% in the next five years and female venture capitalist partners from 9% to 18% in the next 10 years.
An organization of this type has been necessary for a long time, but the key is that it is also now possible because women and men feel empowered to dedicate both the time and money to changing the gender ratio as a core part of our jobs. It’s not a side project that we do twice a year or tweet about and forget. All Raise is something that each of us are dedicating hundreds of hours to across firms and it’s something we work on every week if not every day. While the mission drives us, the opportunity around the economic impact is being full understood by men and women for the first time. Firms who want to compete and thrive in the next decade cannot afford not to care.
What’s the best business advice you’ve ever received?
NORTMAN: When you stop learning, you perish. It’s a cliche thing to say, but I really think it’s an advantage. For me, I was in this crazy article in The New York Times about how I have a Gen Z mentor. It’s actually true, but it started just because I wanted to be helpful to a young woman who I knew was talented. At some point, I realized I was learning more from her than she was from me. It constantly reminds me not to be ageist or industry-ist.