[bonus] Great Engineering War Stories

Todays episode is from the archives.  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


0.43 — Your Startup is a Pirate Ship w. Jack Dietrich & Ryan VanMiddlesworth

Our guests this week are Jack Dietrich and Ryan VanMiddlesworth of Fount Studio.   Join the partners of Fount as they explain The Pirate Code Of Startups how Pirates were doing workplace democracy before it was cool.  Awesome.

[bonus] Advancing Your Career is like Playing Great Chess w. Chris McAvoy

Todays episode is from the archives.

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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[bonus] Reinventing the Organization w. Dan Kador, CTO of Keen.io

Todays episode is from the archives.

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.
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0.42 — Optimize Your Learning Velocity w. Scott Carleton, Andela

Our guest today is Scott Carleton.

Scott has a passion for building communities and empowering self-growth through education. Scott is currently the VP of Technology at Andela, a global engineering organization dedicated to fostering the next generation of elite tech talent across Africa. Previously, Scott co-founded Artsicle as CTO, building a global community of visual artists now featuring over 6000 creators in 100 countries. His work on Artsicle’s discovery engine, which was able to create a personalized experience for passive users, earned NYER’s “Best Use of Technology” award in 2013. 

This episode is for you if you’re into #learning #hiring or #mentorship.

Favorite Quotes

  • You hear a lot that “its all about the people”, but you don’t really get it until it kicks you in the shins.
  • I think a lot about communication through a company in the context of dynamic systems and controls. You can have an input of information where someone’s unaligned or there’s some dissonance, and you’re not going to feel the full impact of that until it works it’s way through the organization.
  • In the early days, I felt like I needed the “best” engineers. That came out as needing Stanford Grads. But what I realized very quickly was that they had very different expectations and needs. I couldnt provide for them the right kinds of challenges because we were still hunting for product market fit.
  • I’ve found that in hiring I should look for “potential” and not “pedigree”.
  • We created a culture of really customer focused engineers. The engineers really own their parts of the product. They *really* care about it’s usability.
  • Friction rises in communication when information doesnt have a place to settle.
  • Chat is a tool. I’m sold on it. A tool is necessary but not sufficient. You need the tool to be able to create the behaviour you want, but you need a cultural change or a behaviour/belief change to use the tool effectively.
  • Chat allows us an always on meeting in its worst form. At best, it’s an asyncronous tool to keep everyone in sync.
  • On chat, my top belief is “Get everything into public channels”
  • The health of an engineering team is: How many issues are raised and resolved, and how fast is that iteration?
  • Finding out how to have the right focus for a conversation in a chat channel is important.
  • When I first started doing 1:1s, I totally didn’t want to do it. I’d make up excuses. Every 1:1, there were engineers who would complain and I just wanted to avoid that. But it turns out 1:1s are invaluable because you’ll always discover something important that you don’t know.
  • If you’re having problems in your organization, a 1:1 is like taking a knife to that problem and sinking it a little deeper.
  • When I first joined an organization with an existing engineering team, the first 1:1s were very much “clearing out the backlog” — Figuring out the existing problems.
  • I have a passion for developing peoples potential.
  • How do we measure someone’s learning velocity – how quickly they’re picking up new skills?
  • The killer problem with distributed teams right now is whiteboarding. It’s just *so* hard to do remotely.
  • Distributed teams are about trust. How do you get the information you need? How do you communicate outward & upward so that we have trust at all times? We need to know we’re all pushing in the same direciton.
  • Whats really incredible about sotware development is that the people who are building the applications have a lot more information about the problems thye’re solving than you do. You really want most solutions coming from the bottom up.
  • I focus on how I can expose business problems to the team. I tell them what we’re solving that quarter, and I put retrospectives on the calendar.
  • Zone of Proximal Development is the Goldilocks Zone for Learning — It isn’t too easy, it’s not too hard.
  • In learning science, you’re trying to “observations”. If you know a skill, you can observe whether an engineer has certain behaviours and beleifs.
  • Customer relationships and ownership of your work are really important for engineers.
  • The height of collaboration is really direct feedback.
  • The most generous thing you can do is give really good critical feedback.

[bonus] Building for Massive Scale w. Tim Jenkins, CTO of SendGrid

Todays 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.
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0.41 — Find A Niche and be The Best w. Courtland Allen of IndieHackers.com

Our guest this week is Courtland AllenMIT 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 Uberes 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 is what they call them now.  This venture capital narrative is fed to everybody.
  • There’s 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 programing 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 in it.  It makes sense to position itself as the one place you can get one specific thing first, then expanding into other markets.
  • I think virtual reality is super cool.  Maybe this time around we won’t hit on VR that works for the masses — portable and affordable, doesnt get us sick.  In the long run, it’s some percentage as good as the matrix.  Its the final frontier for bits taking over the world from Atoms.
  • AI is pretty cool.  What I think is cool about it is not that it’s going to replace what people do, but in many cases it’ll augment what people do.  It’ll work alongside them in a way that allows new business models to exist.
  • There are a lot developers on Indie Hackers.  One of the things you get as engineer is a ton of focus on what it means to be good engineer.  It’s very difficult when you tranasition to being an entrepreneur it’s very difficult to draw a line in the sand and say “OK some of this old advice I got only applied to Engineers as a profession”.  When you are a founder and have a business you have to worry about customers, learning from your customers, increasing sales, setting prices, building a sticky product.  You can’t focus as much as you could before on engineering best practices.  I’ve seen a lot of people build products that followed the best engineering principles; extremely well tested and reliable, but make $0.
  • You can’t be a perfectionist engineer if you’re going to be an entrepreneur (unless you’re building a library for other engineers).  You need to focus on the entire business, and bring yourself to not obsess over trivial technical details of your product.
  • Be flexible, don’t be tied to using the latest greatest technology.
  • It’s OK to massively screw up.  Almost every startup I’ve worked for has massively screwed up.
  • Reading is tremendous.  It helps you encounter problems others have had without having to go through that pain first.  But nothing quite sticks like actually having experienced something.
  • If you’re hesitating to do anything, whether it’s launching your own website or starting your own business, there’s no better way to learn than do it and fail.  Be forgiving with yourself and realize that failure is likely but you’ll learn a lot.
  • You need to be patient as much as you are ambitious.

0.40 — People First Organizations w. Dave Zwieback

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.

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0.39 – Mission Driven Tech w. Zack Bomsta, Owlet

Our guest today is Zack Bomsta, CTO of Owlet, which produces the Owlet Baby Monitor. In addition to growing the team, he is involved 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.

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[bonus] Scaling the Rocket Ship w. Julia Austin of DigitalOcean

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

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