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Geeks Who Lead Podcast — Software How-To
Geeks Who Lead Podcast

Hear the inside stories of the “geeks who lead at scale” – Directors, VPs and CTOs running software engineering orgs at larger companies with 100+ engineers, and interviews with domain experts who can help those leaders to manage their engineering orgs more effectively.

I’m your host – Peter Bell, I’ve been helping senior engineering leaders to connect with and learn from their peers since 2010!

This podcast is designed for engineering leaders who want to learn the latest good practices from their peers who are way too busy operating to write an article or publish a book!

Running a software engineering org at scale is hard! You need to manage stakeholder expectations, attract and retain top talent, align and structure your org effectively and keep up with the latest processes and tooling. And that’s before we even try to make sense of the potential impact of LLMs and GenAI on managing technical teams.

Our podcast and weekly newsletter provide you with access to hard-won wisdom from top engineering leaders and relevant domain experts. Learn more at https://geekswholead.com/

Copyright: © 2020 CTO Connection, LLC

Latest Episodes:

Building for Massive Scale w. Tim Jenkins, CTO of SendGrid Mar 30, 2017

Show notes

Today's episode is from the archives.
We are honored to be joined by Tim Jenkins, CoFounder & CTO of SendGrid. SendGrid solves problems for companies sending transactional e-mail. Tim is currently involved with back-end development, operations, and support, and has worn many hats as SendGrid has grown from 3 team members to over 300 over the last 8 years.
Join us to hear the founding story of one of the most successful email deliverability providers on the web, take a journey through the ebb & flow of a CTO’s responsibilities as a company scales massively, and learn about how SendGrid’s culture has been defined by the 4 H’s: honest, hungry, humble, and happy.

Find a Niche and Be The Best w. Courtland Allen of IndieHackers.com Mar 23, 2017

Show notes

Our guest this week is Courtland Allen; MIT graduate, Y Combinator alum, full-stack web developer, and professional designer. He’s spent over 8 years building, designing, and marketing web-based products and companies, and is currently running IndieHackers.com.
This episode is for you if you’re into bootstrapped businesses, side projects, and community.
Favorite Quotes

I’ve been doing startups ever since graduating from school.
The idea behind Indie Hackers is that it’s completely transparent. Everyone shares their revenue. They share their strategies for growing and marketing their business. We built community through transparency.
You can go on Techcrunch and you can hear about the Snapchats or Ubers of the world. But you can’t learn about Joe the Hacker who is running a $2k/ month business.
The cultures could not be more different (bootstrapped vs VC backed).
Instead of worrying about raising money from VCs and building a billion dollar company, you could instead focus on your product and solving for a need that your customers will pay money for.
A lot of startup founders don’t achieve their goals because the bar is set so astronomically high. In a VC funded startup, sometimes if you don’t reach that goal, your expected value goes to zero.
Indie Hackers community has a lot of people who are making $1k or $2k/mo per side project while working a full-time job. That’s basically like giving themselves a raise.
I wish more people knew you didn’t have to do this crazy all or nothing thing.
The tech press is incentivized by what gets the most eyeballs, which is inevitably going to be the craziest most flashy stories with the biggest numbers possible. The unicorns are what they call them now. This venture capital narrative is fed to everybody.
There are binary outcomes with VC funded companies. They tend to either fail spectacularly or succeed spectacularly. They give you advice and resources that push you to those binary outcomes. I wish people were aware you could build businesses in more of a traditional way, getting revenue from day 1.
Having all of our interviews be transparent was an important value from the start. I wasn’t going to publish any interviews where the founder wasn’t going to be transparent about how they build the business. I was building Indie Hackers for myself, thinking of the time in which I was trying to build a side business myself.
I get inspired by putting myself in the interviewees shoes and seeing the kind of decisions they made to get to where they are.
If you want to start a company, start a company in an area you’re interested in or want to learn about. I need to read books, I need to learn about business, marketing, growth if I want to be able to curate good interviews.
‘I’m a developer, I’m pretty confident in my programming skills. I’m not a great writer, or marketer, or salesperson.’ But what people don’t realize is that you just need to know the basics. Learning how to code is a lot harder than learning how to do a lot of these skills at a passable level.
One of the things I’ve learned about Marketing is the importance of targeting a niche: A specific group of people who share qualities and characteristics who ideally will use your product.
If you target a small specific group of people that you have almost no competition. You can build features that only they care about.
A niche isn’t a group of features your product has. You need to describe an actual existent group of people.
Having a monopoly is important. Whatever target market you’re targeting, you want your audience to look at you as the best possible solution to their problems. Is the market I’m in super humongous? No, there’s not billions of

People First Organizations w. Dave Zwieback Mar 16, 2017

Show notes

Our guest today is Dave Zwieback, the author of Beyond Blame: Learning from Failure and Success and an engineering leader in various organizations in & around New York City.
Dave does workshops for organizations looking to build People First cultures. If you’re interested in hosting a highly-rated, practical, hands-on workshop based on the book at your company, please contact workshops@mindweather.com. You’ll learn the theory and, most important, get to practice conducting Learning Reviews, a critical new practice for building resilient, people-first learning organizations.
This episode is for you if you’re interested in learning about soft-skills, career, or management.

Mission Driven Tech w. Zack Bomsta, Owlet Mar 09, 2017

Show notes

Our guest today is Zack Bomsta, CTO of Owlet, which produces the Owlet Baby Monitor. In addition to growing the team, he is involved in electronic hardware design and miniaturization, manufacturing, firmware, and embedded systems development. Join us to hear war stories from the founding story of Owlet.
Owlet is hiring engineering leaders in UT.

Scaling the Rocket Ship w. Julia Austin of DigitalOcean Mar 02, 2017

Show notes

Our episode today is from the archives. Julia Austin is the CTO of DigitalOcean and a Senior Lecturer at Harvard Business School of Entrepreneurial Management. Hear about her experiences scaling at rocket ship speed leading DigitalOcean’s engineering and product teams.
Find Julia on Twitter at @austinfish and find DigitalOcean at DigitalOcean.com

Understanding People is a Superpower; @rands, VP Engineering at Slack Feb 23, 2017

Show notes

Michael Lopp (also known as @rands) is a Silicon Valley-based engineering leader who builds both people and product at companies such as Borland, Netscape, Palantir, Pinterest, and Apple. While he’s not worrying about staying relevant, he writes about pens, bridges, people, poker, and werewolves at the popular weblog, Rands in Repose. He works as the VP of Engineering at Slack in San Francisco where he’s furiously working on helping teams reinvent work.
Michael has written two books. His first book “Managing Humans, 3rd Edition” is a popular guide to the art of engineering leadership and clearly explains that while you be rewarded for what you build, you will only be successful because of your people. His second book “Being Geek” is a career handbook for geeks and nerds alike.Michael plays hockey, mountain bikes, tinkers with drones, and drinks red wine in the redwoods of Northern California whenever he can because staying sane is more important than staying busy.

From Startup CTO to Acquired by Google — Anant Jhingran, CTO @Apigee Feb 16, 2017

Show notes

Anant Jhingran has been in the tech industry for 27 years and has a Ph.D. in Database Systems from Berkeley. He’s been at IBM, CTO of Apigee, and then after Apigee was acquired, at Google.
Apigee manages an API & data layer for various large enterprises. They look at the data exhaust of those systems and understand patterns so people can improve what they’re doing through the APIs. Apigee was recently acquired by Google, and Anant is working on integrating its technologies into Google’s infrastructure.

From Zero to Sphero w. Ian Bernstein, CTO @Sphero Feb 09, 2017

Show notes

Our guest this week is Ian Bernstein, CTO of Sphero. Sphero is creating a new category of toys called “Connected Toys” that take the best of what kids and adults love about their smart devices and fuse it with our robots that exist in the real world.
Ian’s passion is in electronics and robotics. Ever since he was 12 years old he has been building robots. Learn about how he parlayed his love of robotics into one of the most successful robotics company in the country. Sphero is a robotic ball that can be controlled with a smartphone. The company also makes the BB-8 toy robot featured prominently in Star Wars: The Force Awakens.

Reinventing the Organization w. Dan Kador, CTO of Keen.io Feb 02, 2017

Show notes

Dan Kador is the co-founder & CTO of Keen.io. He’s responsible for building the technology and team responsible for analytics via APIs (among a million other things) at Keen — a leader in the analytics space. Join us to learn about the growth of Keen.io at 3, 10, 30, and (soon) 100 team members; and Dan & his co-founders journey to building a different type of organization — with a team that’s got the autonomy, purpose, and tools they need to deliver great analytics software.

Building for Massive Scale w. Tim Jenkins, CTO of SendGrid Jan 26, 2017

Show notes

Today we are honored to be joined by Tim Jenkins, CoFounder & CTO of SendGrid. SendGrid solves problems for companies sending transactional e-mail. Tim is currently involved with back-end development, operations, and support, and has worn many hats as SendGrid has grown from 3 team members to over 300 over the last 8 years.
Join us to hear the founding story of one of the most successful email deliverability providers on the web, take a journey through the ebb & flow of a CTO’s responsibilities as a company scales massively, and learn about how SendGrid’s culture has been defined by the 4 H’s: honest, hungry, humble, and happy.

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