Amit Gupta, Partner @ SNR Ventures, joins Jerry to discuss his unique eng leadership journey and how that led him to his second career as an investor / coach. We cover some of the lessons learned throughout his time working as VP of various startups and how those experiences shaped his desire to start his own consulting business. Amit defines what a coaching tree is and his philosophy when it comes to mentorship, picking the right projects, and determining what a team needs to work effectively together. Throughout the conversation, we revisit why effective engineering coaching also includes mentorship around company building. Lastly, Amit discusses why eng leaders make good investors and how investing was a natural continuation off of engineering for him. 

ABOUT AMIT GUPTA

Amit Gupta has held leadership roles at multiple high-growth companies from early-stage through the public markets, including Qualcomm, INQ Mobile, Lookout, and Benchling. He combines concentrated, early stage investing with a passion for helping technical founders with company building. In some cases that materializes into a role helping in the trenches and in others a more passive, help as needed voice. Amit has helped countless companies directly and as an advisor to Y Combinator Continuity.

The CAFE(S) framework is a research-backed definition of context quality for AI agents.

DX collaborated with researchers at Capital One, Google, and UVic to give teams a shared standard for reviewing agent context by breaking it into five properties: clarity, actionability, fidelity, efficiency, and security.

Your agent is only as good as its context and the CAFE(S) framework establishes a shared language around context to help you better understand how & why agents go wrong.

Check it out here!

SHOW NOTES:

• Amit’s transition from Qualcomm (1:05)
• Talent acquisitions challenges faced when starting a company (4:58)
• Lessons learned from Amit’s time @  Qualcomm (8:24)
• Strategies for building a support networks as an eng leader (9:41)
• An example of effective mentorship in Amit’s career (11:00)
• Defining work-life integration & how that influences Amit as a coach (12:55)
• Transitioning from a second startup / starting his own consulting business (14:05)
• Why the work at Benchling wasn’t as hard as the first couple startups (16:21)
• Amit’s favorite behavioral interview question (17:40)
• Shared traits of great teams who perform well together (18:56)
• Frameworks for determining good leaders vs. good managers (20:38)
• Ways to feed your high-aptitude leaders (23:18)
• An example of a rewarding coaching scenario (25:25)
• Amit’s perspective on investing as an extension of building (29:38)
• Strategies for determining which bets will be successful (32:16)
• Considerations for the eng leader to investor pipeline (34:43)
• Rapid fire questions (39:53)

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/