0.33 – Bend the Learning Curve by Consistently Putting Yourself into a Place You’re Uncomfortable — Kathy Keating

We’re joined this week by guest co-host Diana Pfeil to interview Kathy Keating —  Kathy is a Colorado based Startup CTO who has helped build several successful technology startups, founded her own technology consulting business, guided product strategy for companies and implemented many complex software applications.  

Join us for the first episode of StartupCTO.io in 2017 to discuss Kathy’s approach to building a startup from the ground up, data & analytics, being involved in the community, mentorship, and creating great software teams.

Favorite Quotes

  • If I build great relationships with people in the community, I learn from them and they learn for me.
  • Learning to say “no” is as important, in some ways more important, than saying “yes”.
  • Great entrepeneurs consistently put themselves in a place where they’re uncomfortable.
  • How can I put my team in a place where they’re comfortable being uncomfortable?
  • I really believe in building trust within an organization.  We each have career goals & aspirations.  We all deserve to be challenged to grow on a daily basis.
  • We’re all mentors and we can all bring out the best in each other.
  • I believe in respect & inclusion.  Everyone has ideas, it’s really important to listen, everyone should be able to give input.
  • Leave everything better than you found it.

[Bonus] – Hire Engineers that are Smarter Than You Are w. Jud Valeski

(review this episode on iTunes)

This week’s episode is from the archives.  It’s an interview with Jud Valeski.  Jud was co-founder of Gnip (acquired by Twitter), a real-time data portability software initiative. From client-side consumer facing products, to large scale back-end infrastructure projects, he has enjoyed working with technology for over twenty years. He’s been a part of engineering, product, and M&A teams at IBM, Netscape, onebox.com, and AOL. He has played a central role in the release of a wide range of products used by tens of millions of users worldwide.

Find Jud on twitter at @jvaleski and at http://one.valeski.org/.

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0.32 — Engineering Values Roundup

We ask each of our guests what their engineering values are. What we love about this question is that the answers boil down the brass tacks of leadership into 2-3 minutes of fundamentals.

We’ve got a fun little thematic episode this week, with 5 answers to this question “What are your engineering values?” jammed packed into a 15 minute episode.

In order of appearance:

  • Nader Akhnoukh– CTO of Kapost
  • Travis Kimmel — CEO of GitPrime
  • Julia Austin — CTO of Digital Ocean
  • Manuel Mattke — Chief Innovation Officer at Opportunity Education
  • Maria Gutierrez & Glenn Vanderburg — Maria is VP Engineering at FreeAgent and Glen is VP Engineering at First.

0.31 – Advancing Your Career is like Playing Great Chess w. Chris McAvoy

We are joined this week by Chris McAvoy to talk about growing your people & their careers.   Learn why advancing your career is like playing great chess; It’s not about having a great strategy; It’s about playing positional chess so that you have all of your pieces in place so when an opportunity presents itself you can take advantage of it.

Chris is a technology leader with a passion for open source communities, innovative products, software and architecture.  He is presently a mentor at Techstars and the VP Engineering at Cognizant QuickLeft.  

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0.30 – Great Engineering War Stories

Last week, @owocki’s startup released a new product — The battles last week during this release reminded us of some of our favorite engineering war stories. We ask every CTO on our show “What is your favorite engineering war story?”, and this episode we’re going to play 4 of our *favorites*.

These four stories are ordered by scale.  We’ll start with “just a guy in the garage with a product” to a war story from a large venture scaled startup.

In order of appearance:

  1. Patrick McKenzie – independent software developer
    1. Story misplacing your pager and being unaware of your outage
  2. Travis Kimmel – CEO of GitPrime
    1. Story about after launch the dance of cleaning up your early assumptions and building new features
  3. Jay Zeschin, Lead Architect at ello
    1. Story of “blowing up”, getting tens of thousands of users, and VC funding all at once.
  4. Jud Valeski – CTO at GNIP, acquired by twitter
    1. Story about screening your customers for success


0.29 – Building Successful Distributed Teams – Gevorg Hovsepyan

Gevorg was the Co-Founder/CTO of LionSharp, where he led development of Gesture and Voice controlled systems.  After he left Lionsharp, he became an Agile product / project manager.  Join Gevorg as we chat about collaborative leadership, agile teams and organizations, customer engagement, and delivering business and customer value at breakneck speed.
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0.28 — Rethinking Education from First Principles w. Manuel Mattke

Manuel Mattke is an innovator, entrepreneur, tech product guy (and from time to time developer), with a background in finance, technology and innovation consulting.

This week is an extra special episode.   Manuel was Kevin’s CTO mentor at the last startup he founded, and Kevin is super excited to share some of the insights that Manuel shared with him, with all of you.

When he’s not mentoring up & coming CTO’s, Manuel is building his own startups. He has founded and built several startups, including an enterprise software company, a mobile app company and an innovation consulting firm, and likes to focus on combining business strategy, innovation and design thinking, and technology products.

Manuel is currently designing and implementing relevant & engaging learning experiences for teens in the US and in the developing world. Education models around the world have seen limited innovation over the last 50+ years, and are ripe for significant new efforts.  Learn about Manuel’s work as Chief Innovation Officer disrupting education at Opportunity Education in this week’s episode. 

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[bonus] Quantifying Engineering w. Travis Kimmel of Gitprime

We’re taking this week off; If you’re in the US, you’re celebrating Thanksgiving.  If you’re not in the US, you can still give thanks — Listen to one of our favorite episodes from the archives:  Quantifying Engineering w. Travis Kimmel of Gitprime.

Travis Kimmel is the CEO of GitPrime.  GitPrime analyzes a team’s codebase to quantify engineering progress. They make it easy to identify engineers who are stuck or bogged down with refactoring, and quantify the amount of effort spent paying down technical debt.

Find Travis on twitter at @traviskimmel.

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0.27 Scaling the Rocket Ship w. Julia Austin of DigitalOcean

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

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0.26 Web Security for Startup CTOs w. Andrew Useckas

Andrew Useckas is the CTO of Threat-X; a 10 person startup based out of Colorado that provides Web Application Firewalls as a Service. Join Andrew as we discuss the most relevant threats to software startup companies today and we learn how he and his team built a next-gen security company.

Find Andrew on twitter at https://twitter.com/daronin and Threat-X at https://threat-x.com/

Favorite Quotes:

An engineer has to be a self starter. I look for someone who can really take initiative; someone who can take a project and make it their own

A quality I look for in hires is ability to pivot as necessary. What tool you use depends upon the task. Things always improve and you have to be flexible.

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