The Dakota Way Sales Coaching is a monthly show hosted by Gui Costin covering the 4 core principles of investment sales — and every episode is backed by the intelligence inside Dakota Marketplace, the global private markets platform used by thousands of investment professionals to research LPs, GPs, and private companies. Built by fundraisers for fundraisers, Dakota Marketplace delivers complete, accurate, and daily-updated intelligence across every allocator channel — from family offices and RIAs to sovereign wealth funds and public pensions. Learn More | Book a Demo
Ryan interned at Dakota in 2013 and joined full-time in 2014. Over the past 12 years, he has been on the front lines of capital raising, marketing equity, fixed income, and private strategies to allocators across the country. In this episode, we covered the 4 core principles of The Dakota Way, what it takes to last in this business, and a few practical techniques that separate top fundraisers from everyone else.
Here are ten of the most important takeaways from our conversation.
1. The Market Is Moving Right Now
Ryan opened with a clear read on current sentiment: money is in motion.
His team was in four different cities the week before we recorded. Allocators are making decisions, particularly in international equity, where Ryan is seeing genuine interest in differentiated ideas. On the private side, capital has started flowing again after a prolonged hold period. The second half of 2026 is setting up as an active fundraising environment for managers who are already in front of the right people.
2. You Are, First and Foremost, a Professional Meeting Setter
I gave this advice to a young professional exploring a career in fundraising recently, and it is worth sharing directly.
The unattractive truth of investment sales is that before you can be a great storyteller in the room, you have to be a relentless meeting setter. That means 20 to 25 cold emails a day, city scheduling on a rolling basis, and a constant focus on finding new allocators. The job rewards people who can treat that grind as a sport rather than a chore. Gamify it, make the most of it, and remember that finding a new allocator is its own kind of win.
3. Cold Outreach Is as Much Marketing as It Is Meeting Setting
Every cold email you send is a brand impression, whether or not the recipient books a meeting.
Even when an allocator does not respond, they now know you exist, what you manage, and where your strategy sits. Ryan noted that at our annual sales conference, multiple allocators confirmed they forward well-written cold emails directly to the analyst who covers that asset class. A tight, clear, one-to-two-sentence email that identifies who you are and what you do becomes an investment idea in their inbox. That is the secondary value of cold outreach, and most salespeople miss it entirely.
4. Do the Job for the Allocator
Ryan shared a specific example of the follow-up work that gets noticed.
He was working with an RIA on behalf of a manager running an international growth strategy. Rather than simply presenting the strategy in isolation, he pulled Morningstar data and built a one-page narrative showing exactly how the manager complemented the RIA's existing asset allocation model. The analyst's feedback: "You just did my job for me." That is the level of preparation that accelerates a relationship from introduction to serious consideration. The goal is to make it as easy as possible for the analyst to present your strategy to their investment committee.
5. Your TAM Has to Match Your Product
Knowing who to call on sounds obvious. Most salespeople still get it wrong.
If you manage a mutual fund, your TAM is the channels that buy mutual funds. If you run a private credit strategy, your TAM looks different. The discipline is to build a target list that reflects actual product fit, not brand recognition or name familiarity. As Ryan put it: we sell apples to apple buyers. That list should be specific enough that you can report against it every week and focused enough that your cold outreach has real conversion potential.
6. City Scheduling Gives You Purpose Every Single Day
The mechanics of the go-to-market plan matter as much as the strategy behind it.
I recommend always having five cities on the calendar at any given time. City scheduling creates structure around cold outreach: you are sending emails because you are going to be in Boston on the 14th, not just because the pipeline needs filling. Each city block targets meetings at 9, 11, 1, 3, and 4:30. The cadence keeps you moving forward and makes cold outreach feel less abstract. You are not just sending emails into the void; you are building a trip.
7. Your Email Subject Line Does Heavy Lifting
The subject line, the opening sentence, and the call to action are not decoration. They are the entire email.
The subject line should read "Meeting Request" plus the proposed date and time. The body should be one to two sentences covering who you are, what you manage, and why it might matter to the recipient. That is it. No throat-clearing, no extensive background, no attachments. Close with a direct call to action: a specific date and time, or a link to pick one. Do not make the allocator work to figure out what you want.
8. The First Two Minutes of a Meeting Set the Tone for the Next 58
Core principle number 3 is about being a master messenger, and it starts before the investment discussion begins.
The opening of any allocator meeting should accomplish four things quickly: who you are, what you manage, how long you have been doing it, and where your strategy might fit in a portfolio. That two-minute centering lets the allocator know what they should be listening for throughout the rest of the conversation. Ryan's goal is to get the allocator talking 70% of the time. To get there faster, ask one question early: "Can you walk me through your investment decision-making process?" The answer will tell you how to steer everything that follows.
9. Ask the Two Tough Questions Before You Leave the Room
Most salespeople walk out of a meeting without ever knowing where they actually stand.
Ryan and I both point to this as the single most common failure in investment sales. After going through the full meeting, before you close, ask two direct questions: Does our strategy fit within your asset allocation model? And if so, do you anticipate conducting a search in this asset class in the next 12 months? The answers will save you months of guessing and misplaced follow-up. We literally banned the phrase "great meeting" internally because it communicates nothing. Ask the questions, get the current status, and know where to categorize the opportunity.
10. Claude Has Eliminated the Most Painful Part of Call Notes
The last core principle is having a killer follow-up system, and the biggest recent upgrade to that system is AI-assisted note-taking.
Ryan and his team now dictate call notes immediately after leaving a meeting, straight into their phone. Claude takes the dictation and writes the notes. If the setup is connected to Slack and Salesforce, the notes flow directly into both. Even if it is not, a quick copy-paste gets them logged in under a minute. The data point that sealed the habit: call note quality drops by 40% if you wait 24 hours. Getting notes into the CRM same-day, with Claude doing the rewriting, means every meeting is fully documented and every opportunity pipeline report reflects what is actually happening.
The Bottom Line
Everything we covered in this episode comes back to the same principle: focus on what you can control and focus on what matters most.
The 4 core principles of The Dakota Way cover 16 total subprinciples, and every one of them is fully within a fundraiser's control. Product quality matters, but you do not need to be the best. You need to be in front of the right people, with the right message, following up with discipline, and reporting progress consistently. That combination, practiced daily, is what separates the top 10% of fundraisers from everyone else.
If you want to see how Dakota Marketplace can support your go-to-market strategy across institutional and intermediary channels, book a demo.
