Building your support network, picking the right projects, and why eng leaders make good investors w/ Amit Gupta #272

SPEAKER_1 (0:02)

The CAFE's framework is a definition framework for what constitutes high quality context. The first dimension C is for clarity. Clarity asks whether the agent can interpret the request the way that it was intended. A request can reasonably be read more than one way. So that is something that can feel obvious to the person, right? It can feel obvious to us because we wrote it, and we bring everything that we know into reading it. Say you ask an agent to clean up the old feature flags. The agent is going to read old, let's say as something that has not been touched in six months across the entire repository. So it will go and remove the flags in other team services too.

One of them might be a kill switch, which is supposed to sit there and be untouched until the day you need it. But because the first step was wrong, everything after it builds on it. So one ambiguous line can turn then into hours of very confident but wrong work.

Jerry Li (1:05)

Stay tuned for a little bit in this episode to hear more from our friends and sponsor DX on their new Cafe's framework and follow the link in our show notes to download the paper for yourself.

Amit Gupta (1:17)

There are people in your organization that can give you tremendous leverage that might not have been either given the opportunity or they're up and comers that if you feed them more, they will grow into that. They may not know how to do exactly the job, but if you feed them enough context and making them 10-minute data dump, I want you to go look at this or look at that, then they come back to you with like, here's what I found, here's five people I reached out to, either in the org or outside the org. What do you think about this? And all of a sudden, you're getting a very different kind of leverage versus I got to find the person who's had to solve all the problems. Finding those people in the organization or hiring some of those people that you know give you tremendous leverage is super powerful.

Patrick Gallagher (1:53)

Hello and welcome to The Engineering Leadership Podcast, brought to you by ELC, the engineering leadership community.

Jerry Li (2:00)

I'm Jerry Li, founder of ELC.

Patrick Gallagher (2:02)

And I'm Patrick Gallagher, and we're your hosts. Our show shares the most critical perspectives, habits and examples of great software engineering leaders to help evolve leadership in the tech industry.

Jerry Li (2:15)

Amit, thanks for joining us today, and we're really excited to have you come in to do this podcast recording with us and to learn from your journey, both as an engineering leader and also an investor. To start with, can you tell us a bit of your background?

Amit Gupta (2:25)

Yeah, thanks Jerry. I'm pumped to be here.

Amit Gupta, I still have been an engineer, I'd say, but started my career in 1998 I was at Qualcomm, did a ton of stuff there as an engineer, was in IC, became a leader there, worked on a bunch of projects. Then I did three serial startups, one in London, two in San Francisco. That's where I became CTO, VP of Venge, had to run the whole show. We'll talk about that quite a bit today. That's probably where I got the most scars. After doing that, I called that Act Two, Act One was at Qualcomm. I transitioned where I am now, combining the best of what I enjoyed in those first two acts with investing. I wanted to help more founders, more leaders than I could do one at a time over three serial startups. Then so I started doing basically fractional work, I called it operating partnership work, brought that into companies few at a time at most, and then marrying that with investing, and then that manifested itself into partnering up with the founder of Lookout Mobile Superior, the second serial startup that I did. We run a venture fund called SNR Ventures, which invests in technical and domain expert founders at the very earliest stages, pre-seed-to-seed type founders, and that's where I spend all my time now.

Jerry Li (3:35)

Your career path is relatively unique among the new year leaders. Like, if you post it in your world, what do you do? Do you become an entrepreneur or retire or become an investor and put all the learning and insights and energy back to building? So, here's one from your transition from Qualcomm, your Act One to a couple of startups. What is some of the first moment that you realized that what you learned at Qualcomm is no longer valid?