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Fundraising hasn't gotten harder, says Dakota founder and CEO Gui Costin. The phone just never rang, and the only way in has always been cold outreach.
That's the starting point of the latest episode of The Dakota Way Sales Coaching, where Gui goes solo to walk boutique-firm fundraisers through the four core principles of investment sales: set expectations, know who to call on, be a master messenger, and have a killer follow-up system. Here are 10 takeaways fund managers can put to work immediately.
1. Put yourself in a straitjacket and run a one-person sales shop
Without a distribution leader, Gui says, you have to supply the structure yourself. Think of yourself as "Sam Smith, Inc." and build every element a big sales organization would have, even when no one is watching. That means your workday belongs to three things only: cold outreach, meetings, and following up on your pipeline. Website and marketing materials are pre-8 AM and post-5 PM work.
2. Write a sales plan and report against it every week
Sit down with your boss, agree on the channels you'll focus on, your top 250 accounts, and what success looks like, then build in a 5 to 10 minute weekly check-in. Gui pushes back on biweekly or monthly reporting: it lets you get away with murder, and any boss who doesn't hear from a salesperson assumes they're playing golf. With 9 to 36 month sales cycles and an 18-month evaluation clock, falling behind in months 6 to 9 is hard to recover from.
3. Let your product structure pick your channels, then start close to home
A private equity fund points toward large RIAs and multifamily offices, while a long-only mutual fund or actively managed ETF points toward RIAs, banks, and broker-dealers. Gui's advice to an emerging manager in St. Louis: draw concentric circles, cover every family office and RIA in your home city first, then expand to drivable cities. The Northeast Corridor from Boston to DC alone holds roughly 40% of the US total addressable market for RIAs and family offices.
4. Keep five cities scheduled at all times
City scheduling is the essence of fundraising. Always have five cities in motion (ten if you want to be more aggressive), circle meeting slots at 9, 11, 1, 3, and 4:30, then pull your prospects by city and channel and start sending emails. Gui's first line in the book says it plainly: no one went to college to be a professional meeting setter-upper. Accept it, gamify it, and keep going. Email beats phone, since allocators are rarely at their desks.
5. Treat every cold email as a marketing email
Use three parts: a "Meeting Request, [date and time]" subject line, one to two sentences on who you are, what you do, and why they should care, and a clear ask. Gui still opens every email with that subject line, even the ones from AI tools. Keep it tight enough that an allocator can drag it into their private credit or private equity Outlook folder, and each email quietly builds a database of ideas on their end. Every return trip to a city also warms up your brand: "it's the third time this person has been in town in three months, they must be legit."
6. Pick the date and time for them, and reference something real
End the email with a specific ask, like "Can you meet in Chicago May 4th at 3 o'clock?" Asking an allocator to suggest a time makes them do your work, which Gui calls disrespectful, and they delete. His bonus tip: after your two sentences, mention something you found on the prospect, such as a podcast appearance or white paper. It shows you care and, he says, raises your close ratio dramatically.
7. Center them in the first two minutes, then ask how they decide
When the allocator says "tell me about your firm," you have two minutes to land who you are and what you do so they know exactly what they're listening for. Before walking through your strategy, say you've researched their firm but couldn't find their investment decision-making process, and ask them to walk you through it. It sets the stage for the rest of the conversation.
8. Aim for the allocator to talk 70% of the time
A Q&A beats a monologue. Gui echoes Stacy Havener's goal of getting the allocator to do 70% of the talking, and cites pitch coach Keith McDowell's rule to give the short answer first so the exchange turns into a conversation. It rarely happens exactly that way, but when it does, the whole game changes.
9. Close every meeting with two tough questions
This is where most fundraisers fall down, because it's emotional, not hard. First: based on what you've learned today, do you see our type of strategy fitting within your asset allocation mix? Second, if yes: for an open-ended strategy, do you anticipate a search in the next 12 months, or for a private fund, can you make our final close date? A "no" at either step gives you an honest answer for your boss and puts the contact on the mailing list. A "yes" tells you exactly what information to send next. For bonus credit, follow Stacy's lead and ask to book a 10 to 15 minute call right then to get their feedback on the meeting.
10. Let your CRM do the remembering, and dictate your call notes
Log every scheduled meeting so you can run 90-day and 180-day lookbacks. Then, as soon as you walk out of a meeting, find a corner of the lobby and dictate your call notes into Claude, ChatGPT, or Copilot, asking it to pull the participants from your calendar invite. Wait 24 hours and the detail you capture drops by roughly 60%. Create an opportunity only when a meeting turns into a legitimate one, and run a pipeline report sorted from closest to close down. Include two custom fields that are never blank, Current Status and Next Step, and review the report with your boss every week.
Dakota Marketplace gives fundraisers the account and contact data behind principle number two: knowing exactly who to call on within your TAM, updated in real time across every institutional and intermediary channel. See how it fits into your sales plan, book a demo.
