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, VP Investment Sales
Watch on YouTube | Listen on Spotify
Executive Summary:
There are no shortcuts to booking meetings, and the July 2026 episode of The Dakota Way Sales Coaching opens with proof of it. Gui Costin and Tim Dolan tell the story of a customer success manager coaching a client through cold outreach by hand, email by email, until the client started booking meetings, then asked if the process could be automated. The answer is no. Allocators can spot AI'd outreach instantly, and the moment they feel automated, the relationship is over. From there, Gui and Tim walk through all four core principles of The Dakota Way, a market read on the busy second half of 2026, and the hack of the day: book out September, October, and early November now, before Labor Day, because decisions rarely get made between Thanksgiving and Christmas.
Show Notes
Products Discussed in This Episode
The complete allocator intelligence platform built by fundraisers for fundraisers. Real-time updates on job and role changes, fundraising news, and allocator activity across institutional and intermediary channels in the US and globally. The Metro Areas feature lets you pull every qualified prospect in a city, broken out by channel, the backbone of the city scheduling process discussed in Core Principle 2.
↓ Download the Platform Guide
A natural language report builder native to Salesforce, built inside Dakota Marketplace. Run reports on accounts, investments, contacts, and more just by asking. Available now for Dakota Marketplace users, coming soon inside Salesforce logins. Learn more at dakotajo.ai.
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. Request a signed copy
Be Kind by Gui Costin Gui's leadership book on lessons learned. Available on Kindle and softcover on Amazon. Request a signed copy
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
Market Check: Second Half of 2026
Tim's read on the market heading into the back half of 2026: busy, and getting busier. Search activity is heavy across public pensions and consultants, and it's spanning every asset class, alternatives, private credit, long-only both domestically and internationally, and fixed income. Dispersion in the market means opportunity for new managers and new mandates. Summer is naturally a little slower, but the team is already planning the fall.
Hack of the Day: Book out September, October, and early November now. Labor Day falls late this year, so plan to be on the road the week of September 9th. You have roughly nine weeks (Labor Day to Thanksgiving) to get meetings done. Decisions rarely get made between Thanksgiving and Christmas, so use that six-week stretch to book out January, February, and March instead.
The Dakota Way: 4 Core Principles
Core Principle 1: Set Expectations with Your Boss
Sit down with your boss, or your PM or CEO, and agree upfront on what good looks like: a one-page sales plan covering where you'll focus and what success means, whether that's $100 million raised this year or $1 billion. Then report progress weekly, always sharing good news and status, so your boss never has to ask what you're doing. This is how you avoid the "law of 18 months," the trap where a new hire spends 6 months without a real plan or pipeline, and now has to raise money on a 9-to-18-month sales cycle in half the runway.
Core Principle 2: Know Who to Call On
Define your TAM. Product structure drives channel coverage: a mutual fund or ETF sells to the wealth channel (RIAs, multifamily offices, banks and broker-dealers), while a long-lockup, QP-only private equity fund sells largely to institutions. Execute against that TAM with city scheduling: keep 5 cities on the calendar at all times, filling time slots at 9, 11, 1, 3, and 4:30 (start with 11 and 1 to avoid a midday gap). No travel budget doesn't mean no coverage, city scheduling still works as an account-coverage model even if every meeting converts to a call.
Cold email format: subject line reads "Meeting Request," with the date and time. Body is 1 to 2 sentences on who you are, what you do, and why they should care, followed by a clear call to action ("Can you meet May 4th at 11 AM?"). Every email is also a brand impression: if it's clear from the first sentence what asset class and strategy you manage, the recipient can file it, forward it, or remember it, even if they don't take the meeting.
Core Principle 3: Become a Master Messenger
The first two minutes of the meeting are for centering the conversation: the check-the-box facts (AUM, firm history, ownership structure, number of PMs) so the prospect knows exactly what they're listening to. Then ask one question: "Walk me through your investment decision-making process." That's your cue into Q&A, where the target is the allocator talking 70% of the time and you talking 30% (most fundraisers run the opposite).
Never leave a meeting without asking the two tough questions:
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Do you see this strategy fitting in your asset allocation mix?
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Do you anticipate doing a search in the next 12 months (or hitting a specific close date, for private equity)?
If the answer is no, you know where you stand. If it's yes, ask what the most logical next step is. "Great meeting" is banned at Dakota, it tells you nothing. Know your status before you walk out the door.
Core Principle 4: Have a Killer Follow-Up System
Get every scheduled meeting and call into the CRM, both for your own recall (two months feels like two weeks) and so you can hand your boss a clean activity report. Get call notes in too: dictate them right after the meeting, ask Claude to write them up, and send them into Slack or straight into Salesforce.
Opportunities need two fields that are never allowed to be blank: current status and next step. You can't fill those in unless you asked the two tough questions in Core Principle 3. Build a simple opportunity report with status, next step, account name, opportunity type, metro area, contact, and notes, organized by sales cycle stage, and that report becomes your daily follow-up list. Dakota uses Salesforce, though any CRM works as long as it captures the activity you're generating.
August’s Coaching Session is at 1pm on August 27th, 2026
30 mins. Practical tactics. No pitch. Build for boutique investment firms raising capital without the budget of a large firm.
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