founder-led prospecting

Good morning Predictable Revenue community,

Big thank you to everyone that volunteered to read the first draft. I don’t have an official Advanced Review Copy (ARC) because we’re still working on copywriting, checking grammar, etc… so expect it not to be perfect. I will send you an email today with a form that says I’m not paying you and all I’m asking for is a review, once you complete that you’ll get a link to the preview.

Oh, and more great news from last week: I heard back from Uber’s legal team, and I’m officially allowed to use their customer story in the book! TL;DR — when Uber launched Uber Eats, they hired us to book meetings with the top 25 restaurants in every new launch city. We managed a 33% meeting booking rate, which meant for every 1,000 emails sent, we booked 330 meetings. It was one of the craziest clients we’ve ever had. We proved the model for them, and they ultimately hired 100 BDRs to replace us. We were sad to see them go but grateful for the experience.

“You smell something Rabbit?” “Fear.” - Super Troopers

Do you ever get that nagging feeling your revenue might come up short this month or next? I do, and it keeps me awake at night. For whatever reason, this week felt slow so I spent most of it focused on creating pipeline for my consulting company (where I coach founders on how to find their first customers) as well as my side project (where I’m trying to book customer development meetings). 

The experience reminded me of my early days, when I was clueless about how to start real conversations with prospective customers. Maybe you’re in a similar spot: you have a company, you have some customers, but you’re not sure how to reach new prospects. I’ve been there, and I know that uneasy feeling in the pit of your stomach when you just can’t see a path forward. If that’s you, this email is for you.

Setting Some Ground Rules

I’m going to talk about building lists and reaching out—typically via cold email and LinkedIn. Your mileage may vary depending on where your customers actually hang out. If you’re unsure, just ask them. In your next customer development meeting, find out how they’d recommend reaching more people like themselves. If you don’t have a meeting booked, reach out to customers (or ex-customers) you’ve interviewed in the past and ask for advice.

Also, proceed with caution if you plan to send 30 or more cold emails a day from your main inbox. Occasional spikes up to 50 probably won’t hurt, but if you’re sending at that level consistently, I’d recommend setting up prospecting domains. If you’re interested in learning more about email deliverability, let me know—I’m working on an internal guide for Predictable Revenue and could share a polished version if there’s demand.

My favorite tools for sending are YetAnotherMailMerge (for low volume), Instantly or Smartlead (for high volume), and Dripify (for LinkedIn).

Why Outbound Can Be So Tough

Outbound fails silently: you do all this work and then get zero responses. It’s hard to figure out whether the problem is your audience, your channel, your messaging, or your product. For reference, a “good” cold email might see a 1% reply rate, while a “good” cold LinkedIn campaign might see closer to 10%. I’ve run campaigns that have done both far better and far worse. Let’s break down the main failure points:

Was the list good enough?
If you spot-check your contacts and at least 80% of them look like a solid fit, you’re probably fine. Don’t waste hours purging every minor misfit. We’re trying to scale your time; if you’re going to review every single account in detail, you may as well craft fully personalized one-off emails. Also, don’t fall in love with a prospect. I’ve done it, too: you see an account that’s “perfect” and start dreaming about that ideal deal. Stop! Just confirm they meet your criteria, add them to the list, and move on.

Does your audience use this channel?
I re-learned this lesson recently while targeting property management company owners on LinkedIn. So far, I’m seeing a 1.3% acceptance rate and a 0% reply rate. If a cold message falls in the forest, does anyone reply? (If you find a funnier punchline, let me know!) Acceptance rate is a decent proxy for LinkedIn usage; with email, you only really have reply rate as a metric.
Keep the math in mind: if you want 10 meetings at a 1% reply rate and you typically convert 33% of replies to meetings, you’ll need to send 10,000 emails. If each prospect gets three emails, that’s ~3,000 contacts for 10 meetings. So if you send out 100 cold emails and get zero replies, don’t assume the channel “doesn’t work.” You just haven’t hit the numbers yet.
(Side note: my goal for the micro-campaigns I sent this week was a 3–5% reply rate. More on that below.)

Did the message resonate?
The best test is to ask someone in your target audience. If you can’t, grab the nearest warm body, read them your draft, and see how they react. Even better if it’s a friend or partner who’ll give brutally honest feedback. If you’re struggling, revisit the MarketFit discussion from last week’s post.

What if 1% isn’t good enough?

Averages are just that—average. Some people see 10–20% reply rates; others get 0.000001%. Your product-market fit and value proposition have a huge impact on these numbers. Check out my previous post on how product-market fit influences GTM channels.

If you can’t (or don’t want to) blast out 10,000 emails this month, try micro-campaigns. Look for signals or events in the market that make your message especially relevant right now. Here’s one I used: speaking at a conference.

During a customer development interview, I learned I should target people who see themselves as leaders in their communities. So I found a conference happening in March and grabbed its speaker list. Here’s how I built the campaign:

Pulling Speaker Data
The first thing I needed was a list of the people speaking, their company, and the topic of their talk. I figured I could use the fact that they were speaking as the reason I was reaching out and what better way to connect than reference the title of their talk. I copy/pasted the page from Chrome into ChatGPT (4o seemed to do the trick) and asked it, “please output a tab separated list of the following attributes, speaker name, topic, company name, and job title. Here is the data: <paste>”. I like using tab separated lists because I can copy/paste right into Google Sheets. Yes, I say please to LLMs… sometimes I say thank you too. 

Finding Their Contact Info
Next, I needed to get their contact info. For this I used Clay (<-- referral link). I start by using Clearbit to get their domain from the company name (it’s a free enrichment), then I use the Google search function on any blanks, and I output the results into a merge field. At first, I used a different method and wasn’t getting very good results, I even was using GPT-01-mini to compare outputs to names, which isn’t very credit-efficient. Fortunately, starting with Clearbit and using Google for the stragglers provided a 100% hit rate after spot checking. 

Getting Verified Emails
Once you have a full name, company website, and job title, getting an email address is a cakewalk in Clay. I used their Find Work Email waterfall enrichment alongside our Zerobounce API key to find potential email addresses across multiple providers, validate them, and only output safe to send addresses.

Light Personalization
My last step was a little personalization. I took the topic of their talk and ran it through 01-mini (using Clay), asking it to complete the sentence, “I noticed you were speaking…”. This piece took some massaging but I eventually got a useful output. 

Yes, I spent more time setting up the Clay table than I might have by sending the emails manually. But now I can replicate this “conference speakers” playbook any time I spot a relevant event.

Putting It All Together

Having a collection of plays like this helps me cut through the noise. My current template could use some cleaning up before I share it publicly, so ping me if you’re interested. I’m also toying with the idea of building a paid collection of these templates with step-by-step guides for each. I could see folks paying $50–$100/month for access to a constantly updated library of “mini-campaign” ideas. Is that realistic or a terrible idea? I’d love your thoughts.

That’s all I have time for this week, let me know if you like these geeky tactical pieces. 

Collin 

PS - last weekend was a friend’s 40th birthday party and they asked me to “make a cocktail”. I used to be a bartender and love making drinks but didn’t want to get stuck behind the bar all night so I scaled up a Zombie into a punch. Here’s the recipe if you’re interested, make sure you mix it with plenty of ice and give it a good stir. The original recipe is from the book Cocktail Codex, which is fantastic. 

• 1.25 L Appleton Signature (rum)

• 1.25 L Gosling’s Dark (rum)

• 700 mL 151-proof rum

• 500 mL Donn’s Mix #1

• 750 mL Lime Juice

• 600 mL Falernum

• 83 mL Grenadine

• 90 mL Absinthe