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CTO Lunches (ctolunches.com)
149 points by mooreds on Sept 16, 2018 | hide | past | favorite | 60 comments



We had/have a group like this in my city. It's kept to a minimum of interactions as it usually descends into war-story exchange quickly. It's a great way to open up some backchannels that might come in handy, but I didn't get anything more valuable out of it that reading some in-depth blog articles wouldn't have given me.


One of the things I do to avoid that in this group is to keep the email list discussions active with monthly discussion threads and updates on member activities. People put a lot of effort into their responses because they know it's a closed group to engineering leaders, so the discussions are amazing


Sounds like it was a social group were people enjoyed having some peers chatting with. Not a research group on cutting edge technology issues. Contentwise the real world can rarely compete with the internet...


Oh indeed it was, it's just that at this point I can take any group of friendly devs to chat and don't need much CTO glitz around it.


Stopped reading at "Group sponsorship by developer focused companies", this sounds so bad when just before they said "no recruiters, no sales people, no gimmicks." => pick one of these two, can't have both at the same time!


I have been a member of the Boulder group for over a year and the sponsorship is relatively new. Before then there was no website, just an email list, and lunch was just pay as you go (which, with 15 people, was a bit of a pain when we got the check).

As far as I can tell, the influence of the sponsor is limited to a thank you at lunch and a shout out on the website. But I understand your concern about the tension. This is something that every volunteer organization or meetup group struggles with:

1. It usually costs money to put on an event worth going to. Not a ton, but food, beverages and space aren't free.

2. People prefer free (and tech people tend to expect free).

I know another meetup that struggled for years trying to solve this problem, and never found a satisfactory answer.

The answers I have seen work for groups are:

1. Find sponsors and thank them

2. Charge a membership fee

3. Only do free stuff (meet in the library, or a park)

4. Have the meetup organizer pay out of pocket (a different kind of sponsorship)

5. Be lucky enough to have already acquired some kind of income generation (typically an older established gepup like a fraternal order)

It's a tough problem.


These are all ostensibly people with high-upper-quintile incomes at minimum. Is it really out of line to just have everybody pay their own lunch check?


No, that's fine, and how things operated for years. Not sure how free lunch really helps attract more folks. However, that doesn't help with other infrastructure like the website, unless you want to ask organizers to pay out of their pocket.

You'd have to ask Miles (who commented above) why he made the switch to sponsorship.


I replied directly above, but the other reason sponsorship is attractive is because it's hard to host a group of 20-30 people for lunch usually.

We've lucked out in Boulder & Denver where we can make a reservation for that big, but a lot of places I've talked to want event fees, so I'm still going to avoid that, but it'd be nice to have the option.


I would give up "free lunch" to have the sponsorship funds going to improving the community interaction. Lunch is ephemeral yet peer mentorship is priceless.


What funds are required to "improve the community interaction"?


It's definitely not too much to ask for people to pay their own bill at lunch, but my goal is to continue to add value to the group, which I think will become easier if there are more resources at the group's disposal. More cities, more engineering leaders to get advice from or make connections to, etc.


How is the Boulder group? I've been meaning to come that way - I'd pay at this point to have strategic rather than consistently tactical technology discussions. Every other meetup group devolves into frameworks, "cool tech", language talks, devops, etc.


There was a good discussion on impostor syndrome at one of the lunches. And once we had a great roundtable lunch discussion on Security (I learned so much that day).


Someone else mentioned"war stories" and I have definitely heard some. But I have found it to be stimulating and interesting conversation, with some different perspectives (for instance on hiring).

However, the best bang for the buck, in terms of strategic insight, is probably the email list.


I'd agree about the email list. The lunch format is great for non-awkward socializing, but people are busy and travel a lot, and the email list gives a way for people to write out long form advice and experiences to give to the group.

That's a big part of what I'm trying to help scale for the group.


I’m pretty sure the model is something like listen to a five minute intro from a sponsor in exchange for a bunch to free food.

That’s pretty much the basic concept behind every professional networking conference, doesn’t seem very controversial.


Why would you want free food? Can't CTOs pay for their "lunch" at a restaurant?

I often have lunch or drinks with other people in our domain, and I don't see why we would ever want a sponsor, we just go out together to eat and/or drink, talk about stuff, you know, just like that.


I try to avoid the 5 minute intros, which is actually well received by the first sponsor I have, because it's less genuine.


This is definitely something I thought a lot about before accepting sponsorship. Right now we only have 1 sponsor, and they picked us because they want to be authentic, without pitches and marketing to the group. So I'm trying to be ultra selective of which sponsors I work with to maintain the genuine connections this group has.


How do you expect to continue to maintain that distance from sponsors under the pressure to grow?

Could CTO Lunches remain small?

Are you organized as a 501(c)(3), a charity where donations are tax-deductible and therefore must not be used for commercial purposes? (That would be effective but is almost certainly too much overhead.)

(Cool project, btw.)


Thanks!

Since you asked, and I started this project simply to benefit the community, I'll dump my thoughts on scaling here (would appreciate any feedback!)

1. Each city has a captain, who is responsible for setting the time & place of each monthly lunch (and possibly for facilitating monthly local email threads / activity updates). A good captain is key to keeping that small, local community feeling going. <<< This is the main answer to your question.

EDIT: I think it's super important to reiterate that each local captain is an engineering leader themselves. It's not some marketing person from a dev-oriented company.

2. Sponsors -- we only have 1 sponsor right now (name.com), and it's about a month old. I met them while organizing Boulder Startup Week because they were volunteering to help organize BSW too. They're headquatered in Denver, so 1 person from the company comes to the Boulder & Denver lunches (they don't give pitches, they just eat lunch and mingle). I still need to talk with name.com if they're interested in continuing to sponsor the group world wide, which would be cool because they're great at video content and they hate timeshare pitches as much as we do. But if they'd like to keep it local, then I think all sponsors should be local. I know in each startup community there are small to mid size companies doing cool, valuable work and not being jerks about it. Those are the types of sponsors that would be valuable to the group, so that's what I'd help focus on.

3. Even more value -- I really haven't thought this through, but I'd love it if I could spend all of my time providing more value to the group. Outside of the time I've spent being a CTO & co-founder of a VC backed company, I love writing books, doing interviews (Kevin & I did StartupCTO.io, a podcast for a while), putting on events, and building little SaaS tools to help people. I'm not sure how to support myself financially to do that (maybe there's a paid premium membership that's optional for people? But the email list & in person event would always be free! Maybe sponsors help me with that?), but that would be amazing.

Oh and structure of the email list: * Everyone * Colorado * Texas * ...

where members can always email just their local group, but they have the option of participating in or starting discussions with the international community.


For a digital version, the Rands leadership slack is a nice virtual community.


I'm a member of Rands too, and I do think it adds some value, but I started this group as an email group because I generally don't think Slack works well for communities. It's one thing for Slack to be used at the workplace where people are usually "always on", but for a community, it's hard to have high value, long form discussions.

The email list discussions have blown me away. People will literally write 10 paragraph emails about their decades of experience, and because it's not in a chat format, all members can check their email whenever and see the thread.


I am member of rands and for breadth of membership and discussion it is impossible to beat. I have met up with folks from that slack a couple of times in the real world and that has been fun. But it's been occasional, for understandable reasons.


Is this for real CTOs, or "CTO"s of companies of 1, just out of bootcamp?


It's for engineering leaders. We don't have anyone who is the "CTO of a company of 1, just out of a bootcamp", but here are some of the profiles of people we have:

1. CTOs & VPs of Engineering of VC backed, bootstrapped, or publicly traded, companies with employee counts of 10-5,000. This makes up the bulk of the members (probably 90%).

2. Engineers who have started their own companies as CEO. They're engineers, have been their entire life, and still do some coding because they love it, but now they happen to also be responsible for other stuff. (5%)

3. CTOs of new startups, out of an accelerator (usually Techstars, Boomtown, or YC). They're teams > 3, so this type of CTO still does a fair bit of coding, but also manages a few resources (either FT, PT, or outsourced) to get engineering done. Their goal is to learn from all the experience in the group. (5%)


This is a better definition, the role of CTO changes dramatically as the company grows. Steve Kleiman (NetApp's CTO) used to joke that a CTO was just a VP of Engineering who failed at Managing people. And while it is funny its also got a hint of truth.

But when you look at Engineering leadership, when you're small (one engineering team) that means the CTO can talk to any engineer and understand and advise them on the technical goals of the product and the processes by which that product is being produced.

As you get larger the CTO needs to be able to explain to a customer's technical staff why their product is the way it is, and how that relates to what the customer wants to do with it. At this point you are probably mentoring more people than managing them, having hired managers for the day to day.

Larger still and the CTO is not only helping customer's see the value, they are watching the changes in the technology that are going to make the current products obsolete in 3 to 5 years. They spend a lot of time looking forward so that they can warn the engineering leadership when it is time to swerve.

Once you're an "Enterprise company" there are now lots of people who are the CTO of this, or the CTO of that. But the actual CTO is an integral part of the executive staff who is keeping the enterprise value up by, most likely, working with the M&A team to acquire companies that will shore up gaps in the strategy.


I know what you're getting at, and there does tend to be a difference between corporate CTOs of non-technical companies, start-up CTOs and CTOs of large tech companies. However, they're all very much real (but different) roles. You can't just throw any developer into a CTO role and expect it to work. Certainly developers do move into CTO roles (myself included) but there's a lot to learn/do beyond writing code.


No, calling yourself "CTO" of a 2 person company does not make you a CTO. You might be a manager, a founder, or some other title, but you're absolutely and unquestionably not a CTO.


That's like saying you start a company by yourself and you can't call yourself a CEO. CTO, at any size, still has a lot of concerns that aren't just code level, so the title is valid.

However, context is very important. Anyone that looks at someone's resume and sees that they're the CEO of a single person company will understand that they're on a different level than the CEO of a publicly traded company.

EDIT: the other thing that gets conflated here in these title discussions is non-technical founders thinking they need a CTO, when really they just need a lead developer. That definitely muddies up the conversations.


I wrote a blog post about this, but I really think that you could follow either path (if you are successful): http://www.mooreds.com/wordpress/archives/2555

That said, I think that a CTO of a 2 person company and a 500 person company deal with a few of the same issues, but a lot of the same responsibility (tech leadership, the final arbiter of tech decisions).


In my case, I'm not even a founder of the company of which I'm CTO, actually I'm not even a director. I was appointed CTO by the board, of which I'm not a member, and the company is profitable.

I suggest you check your attitude.


The person was talking in general. They weren’t talking about you when saying you. They likely had no idea you were a CTO at all. How would they?


> They likely had no idea you were a CTO at all. How would they?

The comment "Certainly developers do move into CTO roles (myself included)" seems helpful there.


I wasn't talking about you specifically. The people I'm referring to are self-proclaimed CTOs of companies that don't have funding, nor a board.


Founder of CTO Lunches here. (Thanks @moreds for submitting)

Ask me any questions you have!


Not really a CTO when I only have 3 people in my team, should I try to join?


CTO is just a title. I'm not in these groups but I think (and hope) it's not about the title, but about the things you would talk about.

You could be CTO in a company of just 1 and having a lot of interesting things to bring to a discussion, and could be a CTO in a company of 10'000 and be dull and worthless in a discussion. You could even not be a "CTO" but a skilled dev with experience and a lot of interesting things to say.


Yes!


Would love to have a London group


Dude there is already a tonne of things like this. Just go on Meetup for London area (e.g. CTO craft London)

I'll be frank, most of the time these lunches / socials are a waste of time.

Why, well there are mostly two types of people that go to them:

* the wunderkids who are there to evangelize their amazing product that they built using Haskell and a C++ engine. They aren't really interested in anybody else (fair enough).

* the recruiters / poachers / ruby fanboys , who are there to get you signed up.

sorry Ruby fanboys/fangirls; I had to pick on someone.


Preach!

This is exactly why I started this group though, to try to avoid this. I try to avoid this with a few tactics:

1. Every social event for developers or nerds like me has been awkward as hell. No one wants to stand in the corner with a beer avoiding people, or shouting over loud ass music. The lunch format has helped avoid that. I've really found that breaking bread and sitting down with food in front of you makes a big difference in the social interactions and the people that feel comfortable coming. You end up making high value connections with the 1-2 people sitting next to you.

2. Local captains are engineering leaders themselves, and they hand curate the group, and kick people out if they're being all sales-y. I curate the Boulder lunch, and it's all engineering leaders facing the same problems. No one except engineering leaders are allowed to come. The only exception to that is our first sponsor, name.com, who sends their 1 community outreach person to eat lunch, chit chat (not a pitch to the whole group), and picks up the tab at the Boulder lunch.

3. The email list provides so much additional value to the group, and because it's email (as opposed to group chat), people love writing long responses and participating over time (sometimes hours, days, or weeks after the last email in the thread has been sent), not just participating in the fleeting moment of a group chat discussion.


Would love to join but the challenge being that I'm north of UK - would love to connect with CTOs outside of the UK to get a pulse of things around the world.


That's what the email list is for :)

Join the waitlist!


I know of two in London - a monthly dinner run by a local startup CTO, and the CTO Craft circles which meet weekly and are more formal (there’s a loose syllabus and a more experienced leader who runs the groups). Ping me via http://douglassquirrel.com and I can put you in touch with both.


Shoot me an email and we'll set it up!


Headed to London this week and wouldn't mind meeting up for lunch.


It would be great if this was open to people who want to make the leap to CTO. Sounds like a good opportunity to learn from others who are already there.


Apply with your background and we can take a look. That is one of the intentions though.


Hi all, Just posting to add depth to the dialogue:

I run a community called enrich (joinenrich.com), which connects CTOs/Engineering Leaders with their peers to form more real connections - so you can call folks on a whim.

Total focus is on developing more long-term, authentic relationships. No sponsorship. Ping me if interested.


Seems like a great idea. How often do people typically connect (weekly, monthly, etc)? Who does the matching (you, random, the requestor)?

FYI, the hamburger menu on your mobile site is empty for Firefox and chrome.


pardon the delay here! We do the matching - based on historical data on what makes a match "work." Groups formally connect monthly, but folks meet in between meetings at their leisure.

And thank you on the hamburger comment!


Let's be clear - CTO stands for Chief Technology Officer. If you break the title into sections you'll have a clear picture of what that means.

Chief -> Top, big cheese, main dude (or dudette)

Technology -> Like computers and stuff

Officer -> Simple definition: "Officers are responsible for the management and day-to-day operations of the corporation." You know, like making decisions and helping the company be successful.

If you fit into that description, even if you don't have that specific title, you are acting as a CTO. Lots of VPs of Engineering fit into that title. So do lots of CEOs of software companies.


Hit me up if you’re in Chicago.


Let's start a Chicago one :)


NYC group?


Shoot me an email!


Tokyo Group?


Shoot me an email and we'll get it going!




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