Software Misadventures Ronak Nathani, Guang Yang

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 two of this conversation, we dive deep into Kelsey’s experiences learning in public and writing “Kubernetes: Up and Running”:
The biggest barrier to getting started with learning in public and a step-by-step guide to overcome it
Cautionary tale of the “JavaScript sucks” guy
Developing the skill of crafting good analogies
The business and economics of writing a book
Much more
 
Segments: [0:01:12] Writing and learning in public.
[0:10:58] Writing "Kubernetes: Up and Running."
[0:16:05] The business and economics of writing a book.
[0:21:27] Why your first book should not exceed 100 pages.
[0:23:36] What prevented Kelsey from giving up on the book.
[0:26:15] Being intentional about building an audience and the cautionary tale of the "JavaScript sucks" guy.
[0:36:44] Authenticity does not guarantee success.
[0:39:09] Developing the skill of crafting effective analogies.
[0:47:47] Advice for engineers to leverage their technical skills outside of the nine-to-five.
 
Show Notes: 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
 
Stay in touch: 👋 Make Ronak’s day by leaving us a review and let us know who we should talk to next! hello@softwaremisadventures.com

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
 
Segments: [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.
 
Show Notes: 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
 
Stay in touch: 👋 Make Ronak’s day by leaving us a review and let us know who we should talk to next! hello@softwaremisadventures.com

As a self-described “gainfully unemployed data person”, Josh Wills is an angel investor and has worked on and led data teams at Slack, Cloudera, WeaveGrid and Google. We discuss:
How to get started with angel investing without a ton of $$
Attributes that define great engineering managers
What’s it like transitioning from management back to IC
Challenges in Climate Tech from a software perspective
And more
 
Segments: [0:01:35] Transitioning from management to individual contributor (IC).
[0:10:19] Emotional intelligence and its role in engineering management.
[0:25:21] Contrasting the hard power of management with the soft power of senior individual contributors.
[0:37:18] Addressing challenges in climate technology.
[0:51:34] The importance of practicality and how to assess it in interviews.
[0:56:01] Josh's journey into angel investing.
[1:12:59] Criteria used by Josh to evaluate whether to invest in a startup.
 
Show Notes: Josh on Twitter: https://twitter.com/josh_wills
The “Touchy Feely” course at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics
Jason Calacanis’s book on angel investing: https://www.amazon.com/Angel-Invest-Technology-Startups-Timeless-Investor/dp/0062560700
 
Stay in touch: 👋 Make Ronak’s day by leaving us a review and let us know who we should talk to next! hello@softwaremisadventures.com

Known for coining the term “Data Scientist”, DJ is a renowned technologist with a diverse background spanning academia, industry, and government. Having led product teams at companies like RelateIQ and LinkedIn, DJ was appointed by President Obama to be the first U.S. Chief Data Scientist where his efforts led to the establishment of nearly 40 Chief Data Officer roles across the Federal government, new health care programs as well as new criminal justice reforms. We discuss:
“Dream in years, plan in months, evaluate in weeks, ship daily”
High school misadventures that shaped DJ’s world view
Under-hyped opportunities in AI
Building with the customer vs. “if you build it, they will come”
Do we need more regulations on AI?
Much more.
 
Segments: [0:01:48] Picking locks in high school.
[0:07:15] How can we make it easier for others to take a risk on us?
[0:11:29] How do you decide whom to take a chance on?
[0:14:24] The 70-20-10 framework for choosing what to work on.
[0:17:49] "No rules, only guidelines."
[0:24:09] Developing personal ethics.
[0:30:52] Building with the customer versus "if you build it, they will come."
[0:34:51] "Dream in years, plan in months, evaluate in weeks, ship daily."
[0:43:56] Ideas should be considered in terms of momentum.
[0:46:11] Under-hyped trends in AI?
[0:51:53] How does AI need to evolve to operate in fields that require very low margins of error?
[0:56:09] Concerning advances that lack sufficient guardrails?
[0:58:55] Do we need more regulations on AI?
[1:02:48] "Failure is the only option."
 
Show Notes: DJ Patil on Linkedin: https://www.linkedin.com/in/dpatil/
The card that DJ carried in his notebook: https://twitter.com/DJ44/status/819316928623902720
DJ’s interview series with thought leaders in Data Science: https://www.linkedin.com/learning/data-impact-with-dj-patil/data-science-how-did-we-get-here
 
Stay in touch: 👋 Make Ronak’s day by leaving us a review and let us know who we should talk to next! hello@softwaremisadventures.com

Erica is a former VP of Engineering at LinkedIn. Having almost dropped out of college, Erica’s journey in tech is a testament to her perseverance and dedication. In addition to leading engineering teams at LinkedIn, Erica founded WIT (Women In Tech) to empower women within the company as well as the broader tech community. We discuss:
How to create incentives for diversity-building work.
Building your personal “board of directors”.
Balancing mentoring work vs sprint tickets.
Structuring a community for long-term success.
Much more.
 
Segments: [0:18:04] building women-in-tech and the importance of leading by example
[0:21:17] creating incentives for diversity-building work
[0:23:30] examples of building better products with more diverse stakeholders
[0:29:48] how to spot red flags during the interview process
[0:32:51] do men and women bring different skill sets to the problem or it's all individual based?
[0:35:34] building your personal “board of directors”
[0:40:21] how to ask people for mentorship if I’m shy?
[0:44:21] exploring new projects
[0:53:32] how to hold yourself accountable when there’s no structure?
[1:03:17] how to structure a community for long-term success
[1:10:22] how to balance mentoring work vs sprint tickets
[1:14:57] journey to being on the advisory board for SJU
 
Show Notes: Erica on Linkedin: https://www.linkedin.com/in/ericalockheimer/
 
Stay in touch: 👋 Make Ronak’s day by leaving us a review and let us know who we should talk to next! hello@softwaremisadventures.com

Mitchell co-founded HashiCorp in 2012 and created many important infrastructure tools, such as Terraform, Vagrant, Packer, and Consul. In addition to being a prolific engineer, Mitchell grew HashiCorp into a multi-billion-dollar public company. We discuss:
How to structure large projects to avoid demotivation or burnout
The "A.P.P.L.E" framework for diffusing tense situations and handling trolls
How to decide what to work on
Mitchell's unconventional transitions from CEO to CTO and then back to an individual contributor (IC)
The quality that Mitchell values the most in an engineering team.
  Segments: [0:14:19] Impactful lessons from working at the Apple Store in college
[0:22:26] Origin story of HashiCorp
[0:26:08] College side project that turned into Mitchell’s first financial success
[0:31:25] Why infrastructure?
[0:39:50] How individual products came about
[0:44:17] Challenges of fundraising as a company with an umbrella of products
[0:48:20] Balancing being the CTO and writing code: “I didn’t want to be that CTO that just produced technical debt”
[0:53:09] Transitioning from CEO to co-CTO
[0:57:26] From CTO to Individual Contributor
[1:06:03] What’s next?
 
Show Notes: Mitchell’s blog: https://mitchellh.com/writing
The “APPLE” principle that has guided Mitchell throughout his career: https://mitchellh.com/writing/apple-the-key-to-my-success
Mitchell’s Startup Banking Story 😂: https://mitchellh.com/writing/my-startup-banking-story
 
Stay in touch: 👋 Make Ronak’s day by leaving us a review and let us know who we should talk to next! hello@softwaremisadventures.com