January 02, 2025
If you’re in investment sales, you already know the truth:
Nobody loves cold outreach.
Sure, we love the idea of meeting new people, making connections, and bringing in the big bucks…
…but hearing “no thanks” (or worse, crickets) can make even the most confident salesperson want to hide under their desk.
So how do we overcome this harsh reality and actually build momentum?
With one simple, consistent practice: 25 Asks a Day.
Yep, it sounds basic. But this rule is powerful.
Why 25, you ask?
Because it’s enough to build meaningful traction in your pipeline without turning your daily outreach into a painful endurance test.
By embracing 25 asks a day, done with just the right approach, you’re going to build momentum, conquer your dread of rejection, and set yourself up for long-term success.
And the secret? Do it day after day, city after city, with the right email that gets straight to the point.
In this article, we are reviewing the importance of consistency with 25 Asks a Day. By the end of this, you’ll have a better understanding of why cold outreach is needed to continue performing your job.
First, let’s address the elephant in the room. We all know why people resist cold outreach: nobody likes rejection. People don’t want to be ignored or hear “no.” And if you’ve ever spent serious time crafting an email – perfecting the subject line, getting every word just right – only for it to disappear into someone’s inbox forever, you know exactly how frustrating it can be.
But here’s the reality: rejection isn’t your enemy. It’s just part of the game.
I get it; cold outreach isn’t easy, and it probably never will be. But 25 asks a day helps us take the sting out of each “no.” It’s a volume game, where even the ghostings and flat-out rejections are paving the way for an eventual “yes.” When you’re consistent, rejection doesn’t feel so personal; it’s just a necessary step toward getting where you want to go.
And hey, if you feel like you’re the only one hearing “no” out there, trust me – you’re not. The “no’s” are just stepping stones to the win.
Now, here’s the thing: if you’re only asking sporadically, every rejection feels like a body blow. Suddenly, it’s all “What did I say wrong?” or “Should I change my approach?” But once you commit to 25 asks every single day, things change. One “no” doesn’t matter nearly as much because you’ve got 24 other asks going, and you know tomorrow you’ll have 25 more.
Consistency is more than just doing the work; it’s about creating unstoppable momentum and building real relationships.
When I talk about city scheduling on Rainmaker Live!, I’m not kidding. With five cities in rotation on your calendar, sending out those 25 asks keeps you on track and gives each day’s work a clear purpose. Today, you’re focused on New York; tomorrow, Chicago; after that, San Francisco. This steady rhythm keeps you productive and, most importantly, helps you create a network over time.
Here’s the magic of this consistency: each ask isn’t just about getting a yes or no today. It’s about building familiarity so that when your prospect is ready to move, they think of you. Every outreach, even if it’s ignored now, is strengthening name recognition. Over time, even people who don’t respond start to know who you are, what your firm stands for, and what value you bring. It’s not transactional; it’s about building long-term value.
That’s what we do at Dakota.
Every ask you send out is one more step in building a true network. So stick to it and stay in front of people consistently. When the timing aligns, you’re the one they’ll reach out to because you’re already in their mind.
Just because you’re sending 25 emails a day doesn’t mean they can be thrown together. Quality matters, and there’s a structure to crafting emails that get responses.
Here’s my go-to approach for writing emails that hit the mark:
This formula works because it’s respectful, professional, and easy to read. When people open your email, they see exactly what you’re asking, and they can decide quickly. Trust me, clarity is respected, and it’s why people respond.
If 25 asks a day are the foundation, then city scheduling is the structure that holds it all together. Instead of firing off emails randomly, city scheduling is about being purposeful in your outreach.
Let’s say you’re focused on Boston today, Dallas tomorrow, and Miami the next. You’re not only putting in the asks; you’re making it easy to follow up in an organized way, and you’re setting yourself up for efficient travel when it’s time to meet face-to-face.
At Dakota we call this “purposeful asks” for a reason. When each day’s 25 asks are focused on a specific place, it’s easier to stay on top of your pipeline and keep everything moving. You’re building a rhythm that’s efficient, intentional, and designed to keep you productive without burning out.
If you want lasting results in this business, start with 25 asks a day. Stick to it, make every ask meaningful, and let rejection lose its sting. By sticking to this routine, you’re doing more than setting meetings – you’re building a network, a pipeline, and a career that lasts.
Cold outreach may never be glamorous, but with 25 asks a day, it’s doable. And the real win? You’re building a pipeline as steady and reliable as you are.
And trust me – when you keep showing up, day in and day out, success is inevitable.
Gui Costin is the Founder and CEO of Dakota.
