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July 31, 2025
As a founder of a SaaS business I have spoken to so many cool, smart and talented private equity investors. Recently I was writing a blog after recording an episode of the Dakota Way Sales Coaching and I got a question:
“Do you think in person versus Zoom is better?”
“From an efficiency standpoint”, I said, “Zoom hands down. From a relationship perspective and the prospect of winning business, in-person 100% of the time.”
I have done 100’s of calls and meetings with private equity firms and I can say the one that resonated the most were in-person.
I believe one way to win in the age of AI is through relationships. How do you get those relationships? Face to face, building them.
That’s the topic of this post. I have done it since 1997 and I can tell you it works.
AI can write emails, scrape founder databases, and score leads faster than any BD rep ever could.
But AI can’t sit across from a founder, look them in the eye, and build trust.
And in private equity, trust still closes deals.
That’s why in this world of automation and scale, the smartest thing a deal sourcing professional can do is go the opposite direction:
Get in the room. Shake hands. Have the conversation.
Enter: City Scheduling, your system for building in-person relationships at scale.
Sure, AI can help you identify which founder to reach out to. It can even write the outreach email.
But when a CEO decides whether to respond, whether to take the meeting, and most importantly whether to partner with your firm?
They’re not choosing based on an algorithm.
They’re choosing based on trust, rapport, and gut instinct.
And nothing builds trust faster than being there in person.
City Scheduling is a tactical approach to deal sourcing where you proactively book 4–6 meetings in one metro area on a single day, and you do it in person.
You sit down with CEOs. You hear their story. You look them in the eye. You ask real questions and share real perspectives.
Zoom is great. We use it every day. But when it comes to building long-term founder relationships, nothing beats face-to-face.
1. Founders Want to Know Who They're Dealing With
They're not selling a product, they're selling their life's work. Being in the room signals you take that seriously.
2. Trust Is Still A Human Emotion
Trust isn't built through automation. It's built through listening, eye contact, tone, and presence. In-person conversations go deeper, faster.
3. It's Your Differentiator in an AI-Saturated World
Founders get templated emails from 50 funds a week. But only one or two fly in, show up, and spend 30 minutes really getting to know them.
That's you. That's your edge.
We built City Scheduling into Dakota Marketplace with private equity deal teams in mind.
The Metro Areas tab in the web app breaks down:
Want to target every logistics and supply chain tech company in Dallas run by a founder?
That takes less than 60 seconds.
Need to line up five CEO meetings in Chicago next month?
Filter by Metro, shortlist companies, pull contacts, and start emailing today.
With Dakota Marketplace, the hardest part of City Scheduling, research and list building, is already done.
1. Pick 5 High-Priority Cities
Start with metros that align with your industry focus and TAM. Dakota's Metro tab shows where the density is.
2. Block One Day for Each
Plan five meeting slots: 9 a.m., 11 a.m., 1 p.m., 3 p.m., and 4:30 p.m.
3. Email ~30 CEOs Per City
Use a simple, respectful, direct approach:
Subject: In Town - Meeting Request Oct 9 @ 11am
Hi [First Name],
I’ll be in Austin on October 9 and would love to meet for 30 minutes. I’m on the BD team at IronCliff Partners—we focus on founder-led software and services businesses doing $5–30M EBITDA.
Not calling with an offer—just hoping to introduce myself and hear more about your journey. Would 11:00 work?
4. Run 5 Cities at a Time
While you're meeting in one, you're booking the next four. It's a constant, disciplined rhythm of outreach and travel.
Every PE fund is getting more efficient. Every CRM is getting smarter. Every BD rep has access to the same lists.
But very few are consistently sitting down with founders.
City scheduling gives you the structure to make in-person meetings part of your system, not just a lucky one-off.
Because when a deal is on the line, the founder won't choose the best algorithm.
They'll choose the firm that showed up, listened, and built a relationship.
Private equity is still a people business.
Yes, use AI. Use automation. Use Dakota Marketplace to work faster and smarter. But then...
Get on a plane. Walk into the office. Have the meeting.
That's how you stand out. That's how you source better. And that's how you win the deal.
Book a demo to see how Dakota Marketplace helps fundraisers schedule meetings!
Gui Costin is the Founder and CEO of Dakota.
