Can someone help me understand what is going on with the mods or the ranking algorithm here? This post was on the front page this morning, dropped from #19 to #50 within in one minute.

Then it reappeared on the front page for a good two hours, now mysteriously dropped from #9 to #50 within one minute.

It's like there is a bot or mod that is flagging it down to #50. I'm beginning to suspect I'm cursed or someone has it out for posts from this domain! Kind of disappointing since I worked really hard on this piece. I've read how the ranking algorithm works but I don't have a voting ring and there is no flame war happening here. Sad face.

Great series. One thing I'm missing though, but it could just be me, is that being the CTO in my experience is often a lonely job.

Everyone else is focused on either business or tech. You're usually the only one that sees both. There's nobody to spar with on the whole picture, you have to make decisions with far reaching consequences on your own.

That's definitely not true where I am. Probably half our devs care about the business side. My co-founder and I are both techies who care about business, so we spar often.

On the far reaching consequences side, I didn't realize how important the choices we made in the first month were. Some of those are still with us.

I can only follow on arohner. We discuss business with all of our developers all the time. Totally depends on the people, but in our team we specifically select for people who see the bigger picture and want to talk business as well.

Especially the first hires need to understand all parts of the business, not just their specifics

That really depends on the company. I see a lot of instances (in SV) where the executive team mostly cares about the technology and product and tunes the business side accordingly.

I'm confused that none of them expressed fear of being the target of a serious DDoS attack. Is it regarded as such a black swan event that it's not even in the radar?

That's one of those 'good problems'.

step 1) worry about how to get big enough that people even know who you are, and think that DDoSing is worth their time

step 2) worry about how to deal with the DDoS

completing step 1 is much, much harder :-)

There's not a lot you can to do prevent your site from being targeted by a DDoS attack.

If you are unfortunate enough to get DDoS'd you probably have enough money to pay for a service like Prolexic, etc that will shield you almost entirely from DDoS attacks. DDoS protection services are used to people signing up during an attack, so they are usually pretty quick to implement. The downside is that services like this tend to be expensive and can mess up regular traffic (especially if you are providing an API).

That's what the CTO of Stanford Hospital listed as his biggest fear, interview #3 in the series (not in this post, but the one before it).

Great insights here. I think there is a common pattern - one that I've experienced as well. Growing a new piece of technology with no customers to an evolved product that scales and has a growing engineering team behind it introduces lots of new issues that have to be dealt with. I'm not necessarily a process freak, but from my experience, having a few solid processes really goes a long way and should be put in place early. Especially revolving around communication of issues and development priorities. When there's a major fire or conflict on teams, there's a big microscope that should be looked through in order to add improvements that will help a company get past future stages of growth more smoothly.

That pattern is called the Red Queen Syndrome and can be paraphrased thus: solving problems uncovers other problems.

Great series! This is my first year as a CTO and I can relate to most of their stories already. It is hard to move away from your comfortable technical zone and have to start to worry more about the non-tech side of the business. A big challenge are the soft skills... once you become CTO you have to deal with a lot more people than with computers. The technical side is a huge challenge as well, but these are fun issues to deal with, although some do keep me awake at night :)

I'm learning a lot reading these interviews, so a big THANKS to the author!

Nice interviews. I really enjoyed reading the answer of Alex Haro to the last 2 days worries. It definitely conveys the fact that technical issues are one component of the job, the others being often more human-related. Software engineers often their have strong opinions (and usually for the best) and making all work together, without going in a techie fight, can sometimes be a real juggling act.

Alex Haro (CTO / Life360) here. Very excited to be a part of this series. Happy to help any way I can. alex@life360.com

Do you have a list of technologies/projects that are your "Yes, we want that, but not right now." list? How do you decide when to flip their do-it-now bit?

Loved your thoughtful responses!

In people's experience, how big does a non-tech company have to be before you can expect the CTO to be really wrong or behind with current practises, hardware and so on?

Great interview. Now can we get an interview series with founders/business owners and ask them what business problems/pains they wish someone could solve for them? :)

Ton's of great content in this series. Really interesting to hear how much CTO's think about company culture.

Really liking this series, a great read. Would love it if you guys made more of them.

Thank you!! It's a slow process, but I'd love to make more. Some ideas I have are: Stories of massive growth/scale, Stories of horrific bugs/failures, Stories of mistakes/regrets, Stories of introspection (realizing something about yourself that changes the way you approach work). I'm particularly interested in stories of conflicts and mistakes -- I feel like people don't share them enough and they can be really fascinating, valuable, and relatable.

fantastic, really like this series that shows people going beyond the early "i have a technology insight that'll work well" to leading the business.

thank you.