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How your ask “to chat” about CTO roles really sounds

I’m writing this out in hopes that it helps a wayward founder, or a technologist to forward this post to the founder who asked you about “working with them on an idea” or “is looking to hire a CTO and would love to get your advice.” (heyo, future me who will be linking to this)

Why HELLO, optimistic founder! Good on you, for having the audacity to believe in an idea so much that you’re willing to put humongous effort, we’re definitely talking years here, and with a extremely high likelihood of failure and all basic statistics pointing to the fact that you will, in fact, burn money and more importantly your time and energy on your idea. Still here? Alright then.

You’ve reached out to a technologist either a) directly asking them to kick in on your idea [with an implication that they’ll do it for the equity, because your idea is super great obviously and totally won’t fail at all] or b) asking for a meeting to “pick their brain”* about hiring and finding a CTO [who will do it for free, see prior reasons].

Direct Ask

This is sending an email directly to some web developer/software engineer you know and asking if they’ll join your project.

Probably don’t do this. In the event that you are interested in working with someone, not because they’re the only computer person you know, but because they are a computer person you know who you also hunch would be fascinated in your idea and interested in it, maybe you can do this.

Now, if you’re less technical (this is a way of saying you don’t know how to build things with computers), there’s also a high likelihood you have little idea of the specialties of the person you’ve emailed. Do they even do the things you’re looking for? Do you know what you need? Eh, I’m guessing you don’t.

But Pam, I have to find someone!

Right right.

Pay someone

If you aren’t willing to pay a contractor a few thousand to build a first version of your idea and start taking in revenue, I really don’t understand what you’re doing.

The beauty of “paying someone” as well, is that firms are willing to do “discovery” with you (sometimes with a fee, especially if you don’t know the shape of your project) to scope out your idea.

This discovery is worth the money, and if you do it with a reputable firm (which by the way, is a totally fine thing to ask your friend about – people love referring business to their network!), you will have an artifact you can even take elsewhere or work off of, should you decide to work with a different firm or freelancer.


You’re not asking directly, you’re “interested in talking about the idea and seeing if anyone in your network comes to mind.”

Unless there is a recruiting fee attached to this, you shouldn’t be asking this. Because what you’re probably trying to do is recruit the person you messaged anyhow, and it’s disingenuous to use this method as a way to the previous method. Gross.

General founder advice

Before talking to technical folk, I highly suggest joining a startups mailing list (the local for Philadelphia is Philadelphia Startup Leaders, they also have a Slack**) and read the archives.

Practically every question you have to ask has already been asked, and just like programmers use Stack Overflow (a site where people ask and answer tech questions) and ye olde Google to solve things, you, dear founder, should be doing your homework before determining you deserve another person’s precious precious free time.

Things never to say in an email about your pitch

This is directly one I got from a friend from college:

“You’re the only person I’m sending this to”

Because we are friends, I told them to never ever say this and why. This is the kind of phrase people see all the time (such as getting recruiter emails from “an up and coming start-up with significant growth opportunities,” like, ok, sounds like all the other 100).

What TO say

Phew it’s so much easier to point out things NOT to do than things TO do right? And I almost promise you’ll be disappointed in this one, cause part of it requires you to go back in time a bit (or resolve to do better now).

You should be care and feeding your network constantly, so that when you do have your brilliant spark and need help, you don’t have to reach out to the edge of your network and ask a lot of them when you haven’t been paying into that bank — give to your community and it will give back to you.

And if you already have your burning idea and it’s too late for that? Pay your contractor to build your MVP, get some revenue, and use that revenue to pay more contractor or to recruit a partner (turns out people are interested in businesses with a proven possibility of an upside!) and carry on.

Caveats and notes

Major caveat, founder – you’ve surely noticed that none of this rant talks about you with your angel investment money or VC money, or plan to get VC money. If you have angel money, you hopefully have the guidance to follow through with the pay-people-for-work plan, and if you have no money but “plan to get VC money” or angel money, invest in yourself first and (say it with me) pay the contractor.

Another caveat — if we are actually friends I probably didn’t send this to you. And if I did, it is only out of love to help you not look like a jackass in front of other people. And to clarify — if we are actually friends that means you know what’s going on in my life, we hang out or talk at least once a month and stay in touch, or perhaps every few if we previously established a close friendship. If you know me from a networking event or group, and we’ve never sought to spend time together outside of that, we probably aren’t friends.

* If you use this phrase, ever, I’m not sorry, I already hate you. Stop saying this and I am much less likely to immediately dock 50 points on my internal judgement of you as a human being.

** If you don’t know what Slack is, dear founder, definitely familiarize yourself as it’s an extremely common medium of the tech space. Apologies but “how to not look like an idiot when you first join a Slack” is a different post, but you’ll figure it out; it can be summarized in three major steps: Have a profile picture/name/fill out your profile, Explore the channels so you know which things are where, and to get a sense of the tone of the place (and post anything in the correct place for it), and thirdly Search the goddamn archives before asking a repetitive question as your first message.

One Reply to “How your ask “to chat” about CTO roles really sounds”

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