Relationship-First Prospecting

Hello Predictable Revenue community,

An ask for a friend: a friend is looking to run customer development interviews with folks that are vibe-coding, doesn’t matter if you come from an engineering background or not. If you’d be up for an interview, hit reply and I’ll make an intro.

VClist update: I took it out of “waitlist” mode because some users weren’t getting the invites. If that was you, registration is now open —> vclist.co. There are ~10k investors with investment activity in the last 90 days that I just added.

Community update: our next GTM club is Feb 13th (next next Friday) at 930am PT, hit me back if you’re interested in joining.

Onto the newsletter…

Cold outbound doesn't work like it used to.

Send 200 cold sales emails, you might get 1 positive reply if you're lucky. Then that person has maybe a 5-10% chance of entering your pipeline. That's 2,000 to 4,000 emails just to get one real opportunity.

The math sucks.

Why Cold Outbound Is Dying

Buyers are saturated. Everyone gets the same "quick question" and "just checking in" messages. More volume doesn't help anymore. It just makes you easier to ignore.

And when your outbound is driven by pressure, it shows. The messaging gets transactional. You skip rapport and go straight to asking. You try to force a conversation the buyer isn't ready to have.

That doesn't make you stand out. It makes you blend in with every other desperate vendor.

How I Stumbled Into Something Better

When I started writing the book, I wanted to interview more founders and hear their journeys. So I invited them on my podcast. I even incorporated a few of their stories into the book.

In the process, I noticed that some of them needed my help. So at the end of the recording, I'd ask if they were struggling with outbound and if they'd be interested in 30 minutes for me to show them some stuff. No strings attached.

I started because I genuinely wanted to be helpful.

What happened was that people started asking about my services, entering my pipeline, and eventually buying from me.

I'd accidentally discovered something: relationship-first messaging works because it doesn't matter if the person is in buying mode right now. You earn the relationship by doing something valuable for them. 

Instead of pitching your product, you lead with something valuable:

• Invite them to your podcast

• Write a blog post or social media post about them

• Invite them to a private roundtable (not a mass webinar)

• Ask for feedback on what you're building

All of these asks start the conversation off on something that isn't about your product. That's the magic.

My best campaign got a 19.4% reply rate. My worst got 6%. To be conservative, let's say you get 5%. Send those same 200 emails and you'll generate 10 conversations. That’s 10x better than blasting out cold emails. 

The upside is clear: more conversations.

The downside? You need to do more work to turn those conversations into pipeline.

People look at this and think, that'll take too long. But here's the thing: the person who would have replied to your cold outbound is likely to also reply to your relationship-first message. So even though you're trying to go slower, you're also picking up random opportunities in the process.

How It Actually Works

Once you're on a call with them, they might ask you what you do. Or you might find something relevant from your professional library (blog, newsletter, podcast) that you can share with them.

The core idea: start the conversation off with a relationship-first ask. Then, if it's relevant to them, ask them for something. Could be as high level as feedback on a new feature or as direct as an offer to take a look at your software.

Critical: you must treat the ask from your initial email as the only thing that matters and the ask at the end as a bonus. The initial ask can't just be a means to an end or people will feel it and feel bait and switched.

The Nurture Problem

Only about 5% of your market is ready to make a change at any given time. That means if you talk to 20 perfectly qualified prospects, maybe one is ready right now. The other 19? They're relationships. And two or three of them will be ready next year.

If you don't have a plan to stay engaged with folks that might be buyers but aren't ready yet, you're going to miss out.

Here are some things I do that build relationships:

1. This newsletter. You're probably not going to buy from my company and I'm totally okay with it. You could buy my book right now if you wanted to. Especially if I said please? There are two new reviews at the bottom of this email if you’re not convinced. 

2. Free monthly Q&A. I run a free Q&A every month for any founder that can't afford my help or can and just wants to learn for free. There's no pressure to buy. My goal is to help people and have a place I can invite folks that might buy from me to hang until they're ready. Sound interesting? Reply with “I’m a freeloader” and I’ll add you. Just kidding, say “GTM club”. Next one is Feb 13th. 

3. Follow Up Fridays. Every Friday I send 5 nurture emails to lost opps that I haven't talked to in more than 90 days. If you want to make this super easy for yourself, pick a monthly theme, write a standard follow up message on that theme, and send it out for each of your Follow Up Fridays.

Why This Feels Wrong

I get it. This feels slow. It doesn't produce instant pipeline.

And if you're not careful, it does feel like bait-and-switch. You say you're doing an interview, but you're really just trying to sneak in a pitch. That's not authentic. That's manipulation.

There's also an emotional tax. You have good conversations with smart people at great companies. They like you. They thank you for the feature on your show. And then... nothing. No next step. No deal. Just a name in the CRM.

But those 19 non-ready buyers? They're not failures. They're future pipeline.

One well-executed relationship-first campaign can create dozens of long-term relationships with people who will remember you when their situation changes. That's not a consolation prize. That's compound interest on trust.

The Real Question

Would you rather force conversations or earn them?

Forcing doesn't work anymore. And earning takes time.

But at least it's real.

Collin

PS - Big thanks to W and Nathan for their recent review (check them out here).

Me too Nathan, me too…