Hosted by Gui Costin, Founder & CEO, Dakota and Rob Robertson, President, Dakota Marketplace
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Executive Summary:
Cold outreach drives everything, and Gui Costin opens this episode by reminding fundraisers why: a referral is great, but the consistency of cold email is what markets your brand and gets you dragged into the right due diligence folder. Gui and Rob Robertson also share three new initiatives coming out of Dakota, an 8-category breakdown of what the highest fundraising firms have in common in their presentation decks, a new Rainmaker of the Year awards program voted on by the due diligence community, and a Dakota-backed recognition for financial advisors who don't make the Barron's or Forbes lists. From there, the two walk through all four core principles of The Dakota Way, and close with the ultimate cold outreach hack: do a little homework on your prospect before you ever hit send.
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
Private fund performance benchmarking built by people who use the data themselves every day. Affordable, customizable benchmarking available now inside Dakota Marketplace.
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.
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
Dakota News: Three New Programs
What Winning Decks Have in Common.
Dakota's 6-person research team, working with Head of Product Pat Tighe and the Claude connector inside Dakota Marketplace, analyzed thousands of manager presentation decks collected from public pension funds over seven years. The result is an 8-page report identifying 8 categories that separate the highest-performing fundraisers' decks from the rest. It's available now inside Dakota Marketplace and will be emailed to all customers.
Rainmaker of the Year.
Inspired by a suggestion from customer Mark Tower, Dakota is launching Rainmaker of the Year: 10 categories, voted on by the due diligence community rather than proposed by Dakota, recognizing the top fundraisers investment professionals actually work with.
A Designation for Financial Advisors Who Don't Make Barron's or Forbes.
Dakota is building a way for fundraisers to nominate and write up the financial advisors they call on and value, most of whom will never appear on the Barron's or Forbes lists (which cap out around 1,200 advisors each). It's a way to deepen those relationships and give advisors a credential of their own.
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:
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Do you see our strategy fitting within your asset allocation model?
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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.
The Ultimate Cold Outreach Hack
To close, Gui ties it back to where the session started: before you send a cold email, do a little homework on the prospect. Check whether they've been on a podcast or written an article, and mention it authentically: "I listened to your podcast with so-and-so, I loved the comment you made about X. I'll be in Boston, can you meet May 4th at 3?" A little research turns a cold email warm.
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