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In this month's episode, Gui Costin sat down with Tim Dolan, a 15-year Dakota veteran, to cover the 4 core principles of The Dakota Way and a handful of habits that separate the fundraisers who consistently fill their pipeline from everyone else.
Here are ten of the most important takeaways from the conversation.
10 Habits Every Fundraiser Should Have
1. Automation Cannot Replace a Trust Business
Gui opened with a story about a Dakota customer success manager who spent weeks coaching a young fundraiser, by hand, on how to write cold emails that book meetings.
The approach worked. Meetings started coming in. Then the fundraiser asked if he could automate the process. The answer is no, and the reason matters: investing is a trust business, and allocators can tell within a sentence or two when they are being AI'd. Every allocator Dakota talks to has said the same thing: if outreach feels automated, they will not take the meeting.
2. Avoid the Law of 18 Months
Most sales cycles in this business run 9 to 18 months. Most fundraisers do not realize how little time that leaves them.
If you spend the first 6 months without a plan, without a real database, and without regularly scheduled meetings, you have already cut your runway from 18 months to 12, or from 9 months to 3. By the time your boss asks where the pipeline is, the math no longer works in your favor. The fix is building a plan of attack on day one, not month six.
3. Plan Your Fall Pipeline in the Summer
Tim's hack of the day: you should be planning September, October, and November before Labor Day, not after it.
Decisions rarely get made between Thanksgiving and Christmas, which means fundraisers effectively have September, October, and the first half of November to get meetings done before the calendar works against them. The fundraisers who wait until after Labor Day to start scheduling are already behind. Book early, and use the first two weeks of December to close out what is left before shifting focus to booking January through March.
4. Set Expectations With a One-Page Sales Plan
Core principle number 1 is set expectations, and it starts with a simple document: a one-page plan that defines what success looks like and how you will report on it.
That means agreeing with your boss upfront on a target (raise $100 million this year, $500 million, whatever the number is) and then showing progress against that plan every week. The goal is alignment, not a status report your boss has to chase you for. As Tim put it, the worst outcome is your boss asking, "What's Tim doing? I haven't heard from him in a while."
5. Know Who to Call On: Product Structure Drives Channel Coverage
Core principle number 2 starts with defining your total addressable market, and the fastest way to do that is by working backward from your product structure.
A mutual fund or ETF points you toward the wealth channel: RIAs, multi-family offices, banks, and broker-dealers. A 10-year lockup private equity fund points you toward institutional allocators with a smaller slice of the wealth channel. Chasing big-name allocators who will never invest in your strategy wastes time that should go toward your actual best-fit buyers.
6. City Scheduling Gives You a Reason to Reach Out
Once your TAM is defined, city scheduling turns cold outreach from a chore into a structured campaign.
Tim recommends keeping 5 cities active on the calendar at any given time, with meeting slots at 9, 11, 1, 3, and 4:30 so you avoid gaps in the day. Emerging managers without a travel budget can still run this as an account coverage model: cover the metro with the right email, and if enough prospects respond, then justify the trip. It also gives you a natural reason to reach out: "I'll be in town with our PM, can we meet?"
7. The Cold Email Formula That Actually Books Meetings
Gui's email structure has not changed in years, and it still works: a subject line that says "Meeting Request" plus a date and time, 1 to 2 sentences on who you are and why the recipient should care, and a specific call to action.
Cold outreach solves two problems at once. It asks for the meeting, and it markets your brand even when the recipient does not respond. If your asset class is clear in the first sentence, allocators can file your email straight into their large-cap growth folder, their private credit folder, or wherever it belongs, and you have made a brand impression whether or not they ever reply.
8. Master the First Two Minutes, Then Get to Q&A Fast
Core principle number 3 is becoming a master messenger, and the meeting is won or lost in the opening.
The first two minutes should cover the check-the-box facts: AUM, founding year, ownership structure, team size, whatever anchors your strategy for the listener. As soon as that is done, ask one question and let the allocator talk: "Walk me through your investment decision-making process." From there, the target ratio is the allocator talking 70% of the time and you talking 30%.
9. Ask the Two Tough Questions Before You Leave the Room
The single biggest mistake fundraisers make is leaving a meeting without knowing where they stand.
Before the meeting ends, ask the two tough questions directly: does this fit your asset allocation mix? If yes, do you anticipate a search in the next 12 months, or can you make the next close date? A no gets you an honest answer and a mailing list placement. A yes gets you real next steps: meet the PM, fill out an RFP, whatever comes next. Gui banned the phrase "great meeting" at Dakota in 2011 for a reason: it tells you nothing about where the opportunity actually stands.
10. A Killer Follow-Up System Runs Through Your CRM
Core principle number 4 is 10x leverage through a CRM, and it starts with getting every meeting, call, and opportunity logged, not just remembered.
Call notes are the piece most fundraisers skip, and Claude has closed that gap: dictate your notes right after the meeting, and Claude writes them up, whether you copy them into Salesforce yourself or route them through Slack automatically. Opportunities should never sit blank. Current status and next steps come directly from the two tough questions above, which is exactly why asking them matters.
Put These Habits to Work
Every one of these habits maps back to the same 4 core principles: set expectations, know who to call on, become a master messenger, and build a killer follow-up system.
None of it depends on market timing or natural talent. It depends on doing the unglamorous parts of the job (the cold email, the city schedule, the CRM entry) with more discipline than the fundraiser down the hall. That is the actual differentiator, and it is fully within your control.
If you want to see how Dakota Marketplace can support your go-to-market strategy across institutional and intermediary channels, book a demo.
