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Craft Ventures’ Lainy Painter on the two questions startup founders must answer.

Lainy Painter is a partner at Craft Ventures and holds previous experience at Battery Ventures, Gainsight, and Goldman Sachs.

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At a glance:

  • How Lainy Painter got a job at Goldman Sachs and excelled.
  • What she learned from working at a startup.
  • The two questions all startup founders must answer.
  • Lainy’s advice for conquering the chaos.
intheir20s: Lainy Painter

In college, at William and Mary, Lainy Painter barely knew what venture capital was, much less any desire to spend her life working in it. Fresh out of undergrad, Lainy landed a role as an analyst at Goldman Sachs.

She got the job by cold emailing her alma mater’s alumni. The one who ended up helping her get the job was explicitly on the “Do Not Email” list.

Through her time at Goldman Sachs’ San Francisco office, she received a crash course in Silicon Valley startup culture. Her time there gave Lainy an up-close look at the outsized impact startups can have on the world.

Lainy excelled at Goldman by being hyper-responsive and hyper-reliable. Being someone you can rely on to get things done well and on time became a massive differentiator for her.

After Goldman, Lainy joined a startup called Gainsight, creating a relatively new category called customer success software. It is easy to forget that software was sold as a one-time sale at one time, not too long ago. The move to SaaS created a new need for this type of software. This experience became Lainy’s masterclass in getting to watch a startup get built and grown out of seemingly thin air.

Lainy transitioned from a Fortune 500 company in Goldman Sachs to a chaotic startup environment in Gainsight.

Here’s what she learned:

  • Now you’re the expert. Finding answers to problems revolves around tracking down the right person with the right prior experience in a large company. In a startup, you may be the first person to encounter a particular problem. Then once you solve it, you’re the expert.
  • You can try on several different roles at once. So you started in marketing but now want to try something in product or started in engineering but are more interested in finance. For people looking to learn what they want to pursue, a startup is an expedited research project to determine what you naturally gravitate towards.

Lainy Painter ultimately began her investment career with Battery Ventures and then transitioned to Craft Ventures. As a venture capitalist, she works daily with incredible founders. As a gut check to see if the founder and the idea are ready for investment, she asks two key questions: why you? And why now?

Why you?

What is it about your past experiences and knowledge that gives you unique insight into this market?

Why now?

Why, 20 years after the widespread ubiquity of the internet, is this product needed now?

Hint* Lainy believes it’s almost always one of two reasons.

1. a technological breakthrough


2. innovation in distribution.

Lainy’s advice for conquering the chaos.

  • Writing everything down. Something so simple can have substantial positive effects on maintaining your mental bandwidth.
  • Asking for deadlines. By setting deadlines, you give yourself a picture of what to prioritize.

Even more:

Listen to the full interview with Lainy Painter.

Listen to inTheir20s most recent episode with Drake’s Jeweler, Jason of Beverly Hills.



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