Keeping Your Aperture Wide

Hello Predictable Revenue community,

Book update: 122 pre-orders! Thank you to everyone that got their orders in last week, I continue to be blown away by your kind words and encouragement.

Investor list (again): In case you missed last week’s email, I've updated my VC & PE list, but this time, I went and looked at the investors themselves, found a list of their investments, boards they sit on, and categorized the types of investments they've made. There are ~25k investors all based in the USA.

You can order the book here. Email me your receipt and I'll share the sheet with you. If you've already sent me your receipt, just reply back—I know who you are 🙂 

Now to today’s email…

One of the biggest mistakes I see early founders make in sales is jumping to conclusions too quickly—whether it's falling in love with a name on the list and imagining them giving you money, or looking at someone's website and thinking "there's no way this is a real prospect." Whether you’re building a prospecting campaign or trying to close a few deals, if you haven’t closed many customers, the honest answer is: you don't know yet.

The Unexpected Wins

When I was growing Carb, I treated every reply like gold. Every lead like it might close. I had just come from my previous startup attempt where leads were non-existent—a reply from a prospect was like a cold drink of water in the middle of the desert. I did this not because I believed they all would close, but because I had no idea which ones would. I "manufactured serendipity" by showing up fully and working each opportunity to the best possible outcome. Some of the best deals came from places I didn't expect.

I once had a prospect where I was confident our product wouldn’t work in their market so I told them so. Intellectual honesty in the sales process is a non-negotiable for me. They disagreed with me and still wanted to try it. Say what you will about salespeople, but this one will tell you the truth, even if he’s wrong. And in this case, I was wrong. Super wrong. This client ended up beating all our benchmarks, turned out to be our first case study, and was one of our longest running clients.

On the flip side, I've seen founders get burned by doing the opposite—writing off prospects before they even get on a call because they didn't fit a super narrow ideal customer profile, or because their first message didn't land. 

Evidence = Confidence in Your Entire Sales Motion

Now zoom out: this isn't just about how you close—it's about how evidence drives confidence across your entire sales motion. The more evidence you have, the more confident you can be in two critical areas: who to target and how to message them (your prospecting pipeline), and how to qualify and prioritize the opportunities you create (your sales pipeline).

Here's how this plays out:

In your prospecting pipeline: Evidence tells you which prospects are worth pursuing and what messaging will resonate. Early on, you cast a wide net because you don't know yet. As you collect data points—which titles respond, which industries engage, which pain points hit—you can narrow your targeting and sharpen your messaging.

In your sales pipeline: Evidence tells you how to qualify opportunities and where to invest your time. Without historical data on what good looks like, every prospect seems equally promising (or equally risky). With evidence, you can spot the patterns that predict real deals versus tire-kickers.

The continuum works the same way in both:

High evidence = high confidence decisions. Your targeting can be laser-focused because you know your ICP. Your messaging can be direct because you know what resonates. Your qualification can be strict because you know what good opportunities look like.

Low evidence = wide aperture required. Broader targeting because you're still learning who cares. Multiple messaging angles because you don't know what will land. Generous qualification because you can't afford to miss the unexpected winner.

The Shift

This shift isn't just tactical—it's philosophical. The evidence you have (or don't have) should fundamentally change your approach:

High evidence = Direct Response: "Here's what we do, here's why someone like you needs it." You can make assumptions because they're based on patterns from actual closed deals.

Low evidence = Relationship First: You need to invest in creating value and relationships before you ever try to sell anything.

The Relationship-First Mindset

Here's what most early-stage founders miss: relationship-first prospecting takes more work than direct response. The deals take longer to enter your pipeline, and you have to actually invest time in creating real relationships. Whether it's interviewing them for customer development, inviting them on your podcast, or finding something else you can do together that creates genuine value for them.

The relationship-first mindset has a specific goal: establish a relationship with a future prospect and either let them opt-in to the sales process naturally, or ask them at the end of your first value-creating interaction—not at the beginning.

When your targeting is wide (because you don't have evidence yet), direct ask messaging tends to fall flat. You're reaching people with varied needs, priorities, and contexts. Your assumptions won't always land. A CFO at a 50-person startup has completely different pain points than a CFO at a 500-person company, even if they both fit your firmographic filters.

Instead, use open-ended approaches that work regardless of their specific situation. Ask for feedback on your approach. Offer genuine value—insights, connections, resources. Invite them to a podcast or roundtable where they can learn something useful even if they never buy. Give them a reason to talk that isn't contingent on them being in-market right now.

The Math

Let me show you why this matters with real numbers. Let's say you're doing 500 prospects per month for 6 months:

Direct Approach:

• 0.5% reply rate, 30% positive responses

• 3,000 total outreach → 15 replies → 5 pipeline opportunities

• 2 weeks from prospect to pipeline

• 100 hours total time investment

Relationship Approach:

• 5% reply rate, 80% positive responses

• 3,000 total outreach → 150 replies → 120 pipeline opportunities

• 4 weeks from prospect to pipeline

• 750 hours total time investment

The relationship approach generates 26.7x more pipeline opportunities and is 3.6x more efficient per hour invested. Yes, it requires more time upfront. But for early-stage founders who need to learn from customers and create content with them, this is another win.

The direct approach gives you 5 chances to learn what works. The relationship approach gives you 120 chances—plus deeper relationships that compound over time.

When You've Collected Enough Evidence

So how do you know when to transition from relationship-first to direct response? It's simple: you look at your closed deals.

The transition happens when you've closed deals that match specific company and persona profiles. The more closed deals you have with similar characteristics, the higher your confidence can be. You start recognizing patterns: "We consistently win with X type of company facing Y problem."

This evidence comes from actual closed revenue—not just conversations, interest, or positive feedback. Until you have repeatable patterns in your closed deals, you haven't collected enough evidence to narrow your approach.

You can predict with reasonable accuracy which prospects will engage and which won't. Your messaging resonates consistently across a defined segment. You're seeing repeatable patterns in objections, use cases, and buying processes.

The Long Game: Earning the Right to Be Direct

Remember: this isn't about being inefficient. It's about being efficient at the right thing. Early on, your most important job isn't closing deals (though that's nice when it happens). It's learning fast enough to build something people actually want to buy.

The founders who win long-term are the ones who earn the right to be direct by first being generous. They collect evidence through actual closed deals before making assumptions. They stay relationship-first until they know enough to be selective.

The earlier you are, the more generous and open your approach needs to be. You're not selling yet—you're collecting evidence. You're learning what "good" looks like. This requires a particular kind of discipline: the discipline of admitting you don't know what you don't know.

Most founders struggle with this because it feels like weakness. We're supposed to have conviction, right? We're supposed to know our market inside and out. But there's a difference between having conviction about the problem you're solving and having premature certainty about exactly who has that problem and how they want it solved.

The strongest founders I know hold both truths simultaneously: unwavering belief in their vision, paired with genuine curiosity about how that vision should manifest in the real world.

So until you know—until you have repeatable patterns in your closed deals—don't narrow your view too early. Keep your aperture wide. Treat every reply like it matters. Show up fully for each opportunity. That's how you manufacture serendipity and earn the right to go direct later.

The most successful sales motion is the one built on evidence, not assumptions. Start wide, learn fast, then direct your fire when you know where to aim.

Until next time, keep your aperture wide and your assumptions in check.

Collin 

PS - bonus tactic time, the second-best part of establishing so many relationships early on is access to the right people. These are folks that can give you advice when you’re considering a pivot, can refer you to other folks that might be a good fit, and might one day become pipeline themselves. All it takes is a little spreadsheet and remembering to drop them an email monthly… That reminds me, I have a few nurture emails to send out myself today.