Hosted by Gui Costin, Founder & CEO, Dakota and Ryan Creighton, VP Investment Sales
Watch on YouTube | Listen on Spotify
Executive Summary:
Fundraising is a grind — and the best firms build systems that make the grind sustainable. In June 2026's episode of the Dakota Way Sales Coaching, Gui Costin and Ryan Creighton walk through all four core principles of The Dakota Way: setting expectations with your boss, knowing who to call on, mastering the allocator meeting, and running a killer follow-up system. Ryan shares a real example of doing the job for the allocator — building a one-page Morningstar narrative that made an RIA analyst say "you just did my job for me." The episode closes with one of the most practical CRM hacks in the business: using Claude to dictate call notes from the lobby immediately after a meeting, cutting a 40-minute task down to 30 seconds.
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
17,000+ RIAs, 46,000+ verified contacts, CIO bios, investment preferences, and 13F holdings data. The primary channel for city scheduling outreach covered in Core Principle 2.
↓ Download the RIA Capital Raising Guide
4,000+ verified family offices, 8,000+ decision-maker contacts across 91 countries. The second primary channel for city scheduling discussed in Core Principle 2.
↓ Download the Global Family Office 2025 Report
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 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.
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
The Dakota Way: 4 Core Principles
Core Principle 1: Set Expectations with Your Boss
The most overlooked discipline in sales. Write a one-page sales plan with defined goals, then show up for a five-minute weekly check-in. Report what you did the prior week, where the pipeline stands, and what the next steps are. Bosses who aren't in the loop assume nothing is happening. Bosses who are in the loop share the good news with their partners and create organizational momentum behind your efforts. The frequency is everything: weekly beats monthly every time.
Core Principle 2: Know Who to Call On
Start with your TAM — your total addressable market. Let product structure drive channel focus. Mutual fund managers call on RIAs and family offices. Private credit managers focus on institutional allocators with alternatives allocation history. Once you know the universe, build a city scheduling cadence: always have five cities on the calendar, book meetings at 9, 11, 1, 3, and 4:30, and send 20 to 25 cold emails per day.
Cold outreach email format: subject line reads "Meeting Request — [Date and Time]." Body is one to two sentences covering who you are, what you manage, and why it's worth 30 minutes. Keep it tight enough that the analyst can forward it directly to whoever covers that asset class. Every email that doesn't book a meeting still plants a flag — you're seasoning the market on who you are and what you do.
Core Principle 3: Be a Master Messenger
The first two minutes of every meeting are spent centering the conversation. Hit the easy checkboxes fast: who you are, what you manage, how long you've been around, where the strategy fits in a portfolio. Then ask the question most salespeople skip: "Can you walk me through your investment decision-making process?" It's not on their website. The answer tells you exactly how to steer the next 58 minutes.
Close every meeting with the two questions most salespeople are afraid to ask:
- Do you see our strategy fitting within your asset allocation model?
- Do you believe you'll do a search in this asset class in the next 12 months?
Ban "great meeting" from your vocabulary. Get a real answer before you leave the room.
Core Principle 4: Have a Killer Follow-Up System
CRM discipline is the leverage point that separates a good fundraiser from a great one. Every scheduled meeting goes into Salesforce. Every opportunity has two custom fields that can never be blank: Current Status and Next Step. Opportunity pipeline reports are how you report back to your boss (Core Principle 1) and how you generate daily sales activity.
The call notes hack: dictate your notes in the lobby of the building immediately after the meeting. Claude rewrites the dictation into clean, structured call notes. If your stack is set up, those notes flow from Claude into Slack and straight into Salesforce. If not, copy and paste takes 10 seconds. Research shows that if you wait 24 hours to write call notes, the detail count drops by 40%. With Claude, there's no waiting.
July’s Coaching Session is at 1pm on July 23rd, 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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