Engineer's guide to startup advising | Kelsey Hightower

We’re super excited to have Kelsey back on the show! Our last conversation was around his incredible career journey - from working at McDonald’s after school to starting his own computer store, to hacking on python infrastructure with the core developers, to meeting Satya Nadella for an interview.

In part one of this conversation, we dive deep into Kelsey’s experiences and expertise as a startup advisor:

• How to break into advising when you don’t have a lot of connections

• How to influence without authority

• Passive vs. active advising

• How to add value as an advisor

• Setting boundaries and expectations

• Much more

[0:01:53] Being a "junior retiree"

[0:11:00] How Kelsey got started with startup advising.

[0:17:43] How to avoid mismatches in advisory engagements?

[0:27:23] How to influence without authority as an advisor?

[0:32:58] How to establish boundaries as an advisor.

[0:38:29] Actions engineers can take today to prepare themselves for future startup advising roles.

[0:42:55] How to manage the balance between advising and your primary job.

[0:44:32] How to cultivate perspectives beyond engineering.

• Kelsey on twitter: https://twitter.com/kelseyhightower

• Our previous conversation with Kelsey about retiring as Distinguished Engineer from Google at 42: https://softwaremisadventures.com/p/kelsey-hightower-on-retiring-as-distinguished-057

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