“The most helpful thing I gained from being an operator was empathy.”

Meet Lainy Painter, Principal at Craft Ventures, an early-stage VC fund headquartered in San Francisco. Prior to joining Craft, Lainy was an investor at Battery Ventures and Goldman Sachs, and held an operating role at Gainsight, a top tech company focused on helping businesses retain and grow customers. We spoke to Lainy about how she translated her operating experience back to investing and what it’s like to help build an early-stage firm.

We’d love to hear about where you grew up. What was your childhood like?

I was born and raised in the Philadelphia area – not exactly the epicenter of innovation and tech, but a great place to grow up. Neither of my parents worked in finance (my mom worked at IBM and my dad worked in pharma) so it was unexpected that all three of their children ended up choosing careers in that arena. My sister works in public equities; my brother works in private equity.  

How did you find your way into the world of finance and tech from Philly?

I worked in investment banking out of college. I was given a seat at the table on day one, which is a credit to Goldman. It was the best training ground for me to develop foundational skills. I loved the mix of analytical and client work. When I moved to SF, I got the opportunity to work with the high growth tech companies that I really admired.

What learnings have you carried over from your time as an operator to your role as an investor?

I think the most helpful thing I gained from being an operator is empathy. My time at Gainsight was a crash course in understanding the challenges startups face. Sometimes duct tape really is the best solution, and sometimes it’s not! I learned how business units function and the tools they use. I used a lot of products that are an important reference point now as I learn about different industries.

What was it like joining Craft as a first-time fund?

The firm has the dynamics of both a fund and a start up, which really excited me. The fund is about a year old, and stands out today because of our combination of investor acumen and operational experience. At Craft, we believe that category-defining companies can be under our nose at any moment and the most important thing to get them to scale is to reduce friction. In my current role, I see this as fundraising friction, but it could also be in sales, supply chain, or another area. At Craft, there are advantages to being a small firm where we’re still able to do things that don’t scale – like drop everything when needed. This has allowed us to move quickly, win deals, and support founders in unconventional ways.

What innovation or change would you like to see in the VC industry?

I’d like to see more innovation in deal flow. Venture investors use existing networks and mental models to make investments. I am committed to bringing in deals from new and different ecosystems. If the pool of companies we consider investing in changes, then the whole funding system will change.

Who are/were your mentors and what did they teach you? Did you have any great female mentors? Do you feel that’s important?

Mentors have been helpful to me at every stage of my career. One of my mentors taught me to speak first in meetings. Sometimes I stress about finding something insightful to say in important meetings. Leading off with a comment is a great trick to take the pressure off.

Fire Round

What is an industry trend that you’re most excited about?

I’m really excited about the built world – real estate, logistics, construction.

What is a favorite or most interesting article you have read from the past few months?

I’ve been reading more about food and thinking through the challenge of how we will feed the next 2 billion mouths – the way we eat and the systems that support us are really interesting to me.

Who is a female entrepreneur or investor you'd most like to meet and chat with?

Ginni Rometty, CEO of IBM

What is the best piece of advice you have ever received?

Speak first. And never be afraid to be first in line for a buffet.

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Madeline Keulen