Data sourced from Dakota Marketplace, the global LP and GP intelligence platform trusted by thousands of investment professionals. Learn More | Book a Demo
Hosted by Gui Costin, Founder & CEO, Dakota and Tim Dolan, Vice President, Institutional Sales, Dakota
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Executive Summary:
Gui Costin opens this session by reminding fundraisers that the four core principles aren't theory, they're twenty years of pattern-matching that Gui and Tim Dolan first documented internally in 2011 and finally published as The Dakota Way in February 2025. The two walk through all four principles start to finish, spending the most time on two habits that separate top fundraisers from the pack: reporting a written sales plan to your boss every single week, and closing every meeting with two questions most salespeople are too afraid to ask. They close by tying Core Principle 4 back to Claude: dictate your call notes in the lobby immediately after a meeting, before the 24-hour clock erodes 60% of what you'd otherwise remember.
Show Notes
Products Discussed in This Episode
The complete allocator intelligence platform built by fundraisers for fundraisers. Covers institutional and intermediary channels in the US and globally. Real-time updates on job changes, fundraising news, and allocator activity. The Metro Areas feature lets you pull every qualified prospect in a city by channel — the backbone of city scheduling discussed throughout this episode.
↓ Download the Platform Guide
Free for Dakota Marketplace subscribers to connect. Gui and Rob discuss using it to dictate call notes straight into Slack or Salesforce, and to ask questions across historical fund presentation decks that would otherwise take months and thousands of dollars to analyze.
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Resources & Documents Mentioned
The Dakota Way by Gui Costin
The only book written on investment sales: 4 core principles for fundraisers. Available on Kindle and softcover on Amazon.
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Be Kind by Gui Cosin
The companion workbook to this episode. Use it to build your sales plan, TAM, city scheduling cadence, and opportunity pipeline report. Available on Kindle and softcover on Amazon.
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Stacy Havener — Allocator Meeting Masterclass
Referenced in Core Principle 3. Stacy delivers a clinic on how to structure an allocator meeting: centering the conversation in the first two minutes, getting the prospect talking 70% of the time, and asking the two tough questions before you leave. YouTube | Spotify
The Dakota Way: 4 Core Principles
Core Principle 1: Set Expectations with Your Boss
The whole system sits under one umbrella: focus on what matters most. In practice, that starts week one on the job with a written sales plan, agreed upon with your boss, that spells out what you're doing daily, weekly, monthly, and quarterly, along with your KPIs. Report back against it weekly, or every other week at the outside. Gui compares it to hiring a personal trainer: you show up because you know you're accountable. Tim reports to his partners every Monday and calls it a forcing mechanism, it's uncomfortable to show up with no updates, so the habit itself drives pipeline activity. Fundraisers get roughly 18 months to prove themselves in a new seat; falling behind in the first 6 to 9 months puts you behind the eight-ball for the rest of it.
Core Principle 2: Know Who to Call On
Establish your TAM, your total addressable market, before you do anything else. Product structure drives channel focus: mutual funds and actively managed ETFs point you toward RIAs, banks, and broker-dealers, while private structures (hedge funds, private equity, private credit) point you toward institutional LPs, foundations, and endowments. Dakota Marketplace breaks investors out by asset class and sub-asset class so you're not guessing. Once your TAM is set, run a city scheduling cadence: always keep five cities on the calendar, booking meeting slots at 9, 11, 1, 3, and 4:30, and backfill as each city's day of meetings clears.
Cold outreach email format: subject line reads "Meeting Request, [date and time]." One sentence max on who you are and what you do. Keep it clear enough that the recipient can drag it straight into the right asset-class folder in their inbox, that's not just scheduling, it's brand building. Close with a direct ask: can you meet at 3 o'clock in Chicago on May 3rd?
Core Principle 3: Be a Master Messenger
The first 30 seconds of a meeting are pure checkbox: who you are, what you manage, how long you've been around, where you're based, AUM. Skip the small talk. Then, before diving into Q&A, ask the question most fundraisers never think to ask: walk me through your investment decision-making process. Once you understand how they decide, get into Q&A and aim to have the prospect talking 70% of the time, an interaction, not a monologue.
Close every meeting with two tough questions almost nobody asks: (1) Do you see this strategy fitting in your asset allocation mix? (2) If yes, do you anticipate a search in the next 12 months, or, for a private strategy, can you make a specific close date? A "no" here saves you weeks of chasing a meeting that was never going anywhere. A "yes" tells you exactly what to do next to keep the process moving.
Core Principle 4: Have a Killer Follow-Up System
This is the 10x leverage principle, built entirely around CRM discipline (Dakota's team uses Salesforce). Start with logging every call and meeting as an activity, so a one-click past-activity report never lets a relationship quietly go cold for two or three months without you noticing. Do 100 meetings in the first nine months of the year, which isn't a stretch if you're running the city-scheduling cadence from Core Principle 2, and there's simply too much information for memory alone; the report is what keeps you honest about who you actually talked to and when. Tie call notes to those activities: dictate them within minutes of walking out of a meeting while it's fresh, ask Claude to turn the dictation into clean notes, then copy them into the CRM. Wait more than 24 hours and the amount of detail you actually capture drops by roughly 60%.
The second half is opportunities: every real opportunity (not a prospect, an actual live conversation with due diligence underway) needs two fields that can never sit blank, Current Status and Next Step. Those two fields only get filled in if you asked the tough questions in Core Principle 3. The resulting opportunity report is what you review weekly with your boss, closing the loop back to Core Principle 1.
Bring The Dakota Way to Your Team
Gui closes by opening the floor to teams: he's happy to come in and speak directly to younger fundraisers about the four core principles from the book. If interested, reach out to gui@dakota.com.
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