Fundraising is brutal.
You’re setting meetings, dealing with rejection, and operating in an environment with no feedback loop. You’ll send 200 emails and hear nothing. Walk into meetings blind. Grind for months and feel like you’re getting nowhere.
At Dakota, we’ve lived that. We've raised over $40 billion for our partners since 2006 by staying disciplined to a system that removes emotion and replaces it with process.
That system is The Dakota Way. It simplifies the chaos of fundraising into repeatable actions you control. It’s about structure. It’s about doing the work.
In this article, we’ll review the top 10 fundraising best practices from our founder and CEO, Gui Costin. By the end of this, you’ll have a better understanding of these and takeaways to put into action to help you win more meetings, have better conversations, and ultimately raise more capital.
1. Embrace the Job: You Are a Professional Meeting Setter
No one went to school to cold call and get ignored. But in fundraising, 50% of the job is just that: setting meetings. If you don’t own this reality, you’ll burn out. The best fundraisers know that success isn’t luck. It’s repetition. Outreach. Dials. Emails. Every single day.
Embrace the role. Be the dog, not the tail.
2. Set Clear Expectations With Your Boss – Weekly
If you don’t know what success looks like, how can you hit it? You must create a one-page sales plan that outlines your outreach goals, meeting metrics, and follow-up cadence… and report against it every week.
No more quarterly check-ins. They’re a disaster. Weekly check-ins drive urgency, accountability, and clarity.
3. Know Your TAM: Only Call the Right Buyers
You can’t sell apples to orange buyers. Define your Total Addressable Market (TAM) and stick to it. Mutual funds and ETFs? Go RIA, private bank, wirehouse. Private equity Fund III? Talk to family offices, consultants, institutions.
The minute you start guessing who to call on, you’ve lost control.
4. Use City Scheduling to Build Pipeline Momentum
City scheduling turns chaos into order. Every investment sales person at Dakota always has five cities in play. We stack meetings at 9:00am, 11:00am, 1:00pm, 3:00pm, and 4:30pm to build focused momentum.
Each return trip to a city unlocks more relationships, more allocators, and more opportunity.
5. Send Cold Emails That Actually Work
Mass emails do not work. Cold outreach only works when it is personal, specific, and clear. The Dakota Way formula:
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Subject: Meeting Request – [Date & Time]
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Two crisp sentences on who you are and what you do
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A specific ask: Can you meet Thursday at 3:00?
Never ask “the week of.” Never send marketing fluff.
And when possible, personalize the email with one sentence about a podcast, article, or quote from the prospect.
6. Open Every Meeting With a 2-Minute Positioning Statement
Small talk ends. Then what?
You have two minutes to establish who you are, what you do, and why they should care. Do not make the allocator figure it out. They won’t.
Your positioning statement sets the tone. It de-risks the conversation. It tells them exactly what to listen for.
7. Ask the Most Important Questions First
Before you dive into your pitch, ask this: “Can you walk me through your investment decision-making process?”
That question changes everything. It tailors your pitch. It aligns you with their evaluation process. And it prevents you from giving the wrong presentation to the right person.
8. Let the Allocator Talk 70% of the Time
You’re not there to perform. You’re there to listen. Fundraising is a 70/30 game: allocator talks 70%, you talk 30%.
Ask smart questions. Listen actively. Turn the meeting into a conversation, not a monologue.
9. End Every Meeting With the Two Tough Questions
Never leave a meeting without asking:
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“Do you see a strategy like ours fitting into your allocation mix?”
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“Our final close is [insert date]. Is that a close you could make?”
If they say no, take the loss and move on. If they say yes, now you’ve got a real prospect. No more ghosting. No more ambiguity.
10. Use a CRM or You Will Fail
Without a CRM, you’re at 1x productivity. With one, you’re at 10x. Why? Because your brain cannot track:
- Next steps
- Follow-ups
- Open loops
- Pipeline status
- TAM segmentation
The fourth principle of The Dakota Way is having a killer follow-up system. That means you use your CRM religiously. Period.
Final Takeaway
Fundraising isn’t about charisma. It’s about doing the work every day with discipline, process, and resilience.
Here’s the Dakota playbook in four bullet points:
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Set expectations (with your boss and yourself)
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Know who to call on (TAM and practice city scheduling and cold emails)
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Know what to say (positioning, questions, storytelling)
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Have a killer follow-up system (CRM)
You follow this every day, city after city, and you will win.
Book a demo of Dakota Marketplace to join the thousands of fundraisers using it daily to help raise capital!
