Term Sheet -- Wednesday, May 9

5 Qs WITH A DEALMAKER

Good morning, Term Sheet readers.

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. Read the full Q&A here.

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.

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 reaching 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.

Read the full Q&A here.

THE LATEST FROM FORTUNE...

• Why Reddit, Pornhub, and Many Other Websites Are Going on 'Red Alert' for Net Neutrality (by Mahita Gajanan)

• Telecom Tycoon John Malone Is Scaling Back His European Empire (by David Meyer)

• Why Elon Musk Is a Superstar in Iceland

• Walmart Has Beaten Amazon in the Battle to Buy Flipkart

VENTURE DEALS

• Owlet Baby Care, a Lehi, Utah-based health tech company, raised $24 million in Series B funding. Trilogy Equity Partners led the round, and was joined by investors including Eclipse Ventures, Broadway Angels, Enfield Ventures and Pelion Venture Partners.

• SafeBreach, a Sunnyvale, Calif.-based cybersecurity company, raised $15 million in Series B funding. Draper Nexus led the round, and was joined by investors including PayPal, Sequoia Capital, Deutsche Telekom Capital Partners and HPE Pathfinder.

• Fictiv, a San Francisco-based manufacturing platform, raised $15 million in Series B funding. Investors include Intel Capital Global Summit, Accel, Intel Capital, Bill Gates, FJ Labs, Tandon Group, and the Stanford-StartX Fund.

• Avaamo, a Los Alto, Calif.-based provider of AI technology focused on conversational computing in the enterprise, raised $14.2 million in Series A funding. Intel Capital led the round, and was joined by investors including Ericsson Ventures, Mahindra Partners, Wipro Ventures and WI Harper.

• At-Bay, a Mountain View, Calif.-based cyber insurance company for the digital age, raised $13 million Series A funding. Investors include Keith Rabois of Khosla Ventures, Yoni Cheifetz of Lightspeed and Shlomo Kramer.

• Xnor.ai, a Seattle-based artificial intelligence startup, raised $12 million in Series A funding. Madrona Venture Group led the round, and was joined by investors including NGP Capital, Autotech Ventures and Catapult Ventures.

• Rootility, an Israel-based developer of root-focused plant breeding methods, raised $10 million in Series C funding. ADM Capital’s Cibus fund led the round, and was joined by investors including GreenSoil Investments and Middleland Capital.

• Wellist, a Boston-based provider of integrated patient experience solutions, raised $10 million in Series A funding. Summation Health Ventures and .406 Ventures led the round.

• Sckipio, an Israel-based provider of Gfast products, raised $10 million in funding. MegaChips led the round, and was joined by investors including Intel Capital, Pitango Venture Partners, Genesis Partners, Gemini Israel Ventures, Amiti Ventures, Aviv Ventures, CIRTech Fund and Axess Ventures.

• Drishti, a company that applies action recognition to digitize human activities, raised $10 million in Series A funding. Emergence Capital led the round, and was joined by investors including Andreessen Horowitz and Benhamou Global Ventures participated.

• Murj, Inc., a Santa Cruz, Calif.-based digital healthcare company, raised $8.5 million in funding. Longitude Capital led the round, and was joined by investors including joined by investors including True Ventures.

• HousingAnywhere.com, a Netherlands-based operator of an accommodation platform for international students, raised 6 million euros ($7.1 million) in Series B funding. Vostok New Ventures led the round, and was joined by investors including Real Web and henQ.

• Luna DNA, a Solana Beach, Calif.-based community-owned genomic and medical research database, raised $4 million in funding. Investors include Illumina Ventures, Arch Venture Partners, Bridgelink Capital and Hemisphere Ventures.

• SHOP, a Seattle-based blockchain-based ecommerce startup, raised $2 million in funding. The investor was Reflective Venture Partners.

• AI.Reverie, a San Jose, Calif.-based provider of data to train machine learning algorithms, raised seed funding of an undisclosed amount. Investors include Vulcan Capital, Compound and Locke Mountain Ventures.

HEALTH AND LIFE SCIENCES DEALS

• CStone Pharmaceuticals, a China-based biopharmaceutical company, raised $260 million in funding. GIC Private Ltd. led the round, and was joined by investors including Sequoia China, Yunfeng Capital, 6 Dimensions Capital, CITIC PE, Taikang Insurance Group, ARCH Venture Partners, Hillhouse Capital, King Star Capital, 3W Partners, AVICT, and Terra Mafnum Capital Partners. Existing investors Oriza Seed Venture Capital , Boyu Capital, and WuXi Healthcare Ventures participated.

• Genprex Inc, an Austin, Texas-based developer of immunogene therapy for non-small cell lung cancer, raised $10 million in funding. The investors were not named.

PRIVATE EQUITY DEALS

• Mayfair Private Equity acquired GCI, a U.K.-based independent telecoms and data services company. Financial terms weren't disclosed.

• Simplura Health Group, a portfolio company of One Equity Partners, acquired Keystone In-Home Care, a Lancaster, Penn.-based provider of in-residence care services for seniors. Financial terms weren't disclosed.

OTHER DEALS

• Lumni acquired Paytronage, a New York City-based direct-to-consumer marketplace for income share agreements. Financial terms weren't disclosed.

FIRMS + FUNDS

• Linden Capital Partners, a Chicago-based private equity firm, raised $1.5 billion for its fourth private equity fund, Linden Capital Partners IV.

• Female Founders Fund (F3), a New York-based seed stage venture fund that invests exclusively in female-founded companies, raised $27 million for its second fund.