Hey Reader,
Do you have a pipeline problem or do you have a nerve problem?
More specifically, are you more comfortable emailing 20k cold leads via some LinkedIn automation than asking your network for help?
The answer to almost all of your early-stage questions - maybe late-stage too - is likely in your contacts. And before you start trying to find more cold imaginary leads that kinda match your ICP and put them in some sort of doom funnel, why wouldn't you text your contacts? All of them.
More explicitly, why wouldn't you text all your contacts introducing what you're doing, explaining what you need, and giving them a chance to be part of the solution?
I know the answer. Cringe. I've talked about it before, the spotlight effect. You might call texting your entire contacts cringe, but what you mean is that you think the people who get the text will think you are cringe. Maybe, but those people who choose to think less of you for hustling, for asking, for putting yourself out there, weren't going to help you anyway so who cares.
I know the other answer. I don't have the contacts, I don't have that kind of network, I'm not privileged like that, I'm not a tech bro like that, I don't have angels or CHROs or AI engineers in my contacts. Maybe. But it feels like an insane assumption to believe no one in your contacts is one degree away from anyone.
Isn't it ridiculous? You started a startup you believe in deeply enough to risk everything, but you won't text the people who already know you?
You think asking your network for help is weak, but asking some rando via cold outreach for 15mins and to book time on your calendly is strong?
Someone's mum, dad, sister, cousin, boyfriend, wife. Friend they play soccer with. Fantasy league buddy. You don't know who people know. You undervalue what's sitting right in front of you.
Your first instinct right now is to think about segmentation. Which contacts get which message, who's relevant for what. It's just procrastination disguised as strategy.
I was putting off texting my 8,000+ contacts about my book that got published (that was the ad!) for lots of totally valid reasons. I couldn't imagine sending to my ex-employees who didn't leave on great terms, opposing counsels, people who screwed me over, people I probably owe apologies to, my kids' kindergarten teacher, the parents of the AYSO team I coach, my plumber.
The thought of exporting to CSV and doing some spreadsheet thing for 9 years made it too much effort. It was either send to all or none... That would have been the old way...
So I built a thing in Cursor this morning. Takes my entire contacts file, shows me each contact one by one, and I can skip, send, or add a custom message. Click yes, it sends my template text via iMessage. That simple. (yeah, some extra stuff to make sure I don't send twice to the same number, some logging, and a progress bar for my sanity).
I had to create rules for who to SKIP - not based on weirdness or time passed. At first it was obvious. People who if they replied would make me puke a little. Then I realized I didn't care either way. The only real rule was if it would be deeply inappropriate.
Built in about 2hrs. Sent 1,076 today (skipped 153). Some of you probably got it...
Then... my old neighbor, whose last text was asking if FedEx delivered a package to me by mistake, sent a screenshot of his purchase saying "of course" and congrats. A dad I co-coach AYSO with said "done, had no idea." My old boss at SAP, who's now CEO of a pretty massive org, said "done, look forward to reading" and wanted to catch up. It kept going. Old friends, from different lives. A mega old connect who is now a big time startup lawyer, another who sold his company last week for $155m. Every reply made me smile to reconnect and for them to CHOOSE to support and for me to restart conversations.
The awkward feeling disappeared. Yes, a few "who 'dis" messages, one "unsubscribe," and Erika the stylist who somehow got in my contacts - we still don't know how, but she bought the book anyway.
That's it. That's my message. This is not a cringe email, or a get over yourself email, or record the TikTok email, or overcome how others look at you email. No way. This is way more mechanical.
Text your contacts. Do that. Now.
The message I sent:
Hi. If you are getting this text you're in my contacts. That means this message is either welcomed, overdue, misplaced, or awkward.
Either way, I wrote a book: Starting A Startup. It's for entrepreneurs ready to build real things.
Pre-orders matter. If you'd consider ordering a copy, it would be massive.
If you want the app to swipe through your contacts and send from your actual iMessage (not some random service number), and you're on Mac, lmk and I'll put it together.
The most uncomfortable action is often the one that changes everything.
If I can be of service, feel free to grab time.
LFG.
-- James
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