The $30B Sales Playbook

Welcome To The Orbit Marketing Newsletter 🪐 

This Week We’re Diving Into:

• 💼 Case Study: How Dakota raised $30B+ by combining cold outreach with a “D1 mindset”

• 🎙️ Featured Podcast: How to scale your business using other people's audiences

Read time: 4 minutes

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Case Study: How Dakota Raised $30B+ For Their Clients

Sales is hard for one reason: it’s emotional.

That insight has helped Gui Costin, Founder & CEO of Dakota, raise over $30 billion for boutique investment managers since 2006.

In this special episode of the Orbit Marketing podcast, Gui pulled back the curtain on how he built a scalable, thriving, emotionally intelligent sales machine.

Here are the key takeaways:

For beginners, rejection isn't a pipeline problem, it's an identity crisis.

Leaders who don't acknowledge the emotional weight of sales will churn through good people.

Gui's fix? Build a culture that supports resilience and removes the shame around silence.

Here’s how:

🍎 Sell Apples to Apple Buyers

Stop convincing. Start qualifying.

Gui's principle is simple: don't waste time persuading people who aren't a fit. If you're in the convincing business, you're in the wrong business.

📧 Content Is the New Cold Call

70% of buying decisions happen before the first meeting, especially with millennial buyers.

Dakota leans into this by making content that directly answers the questions prospects are already searching for.

Think:

• "Top 5 Family Offices in Boston"

• "Best CRMs for Investment Firms"

• “How to Integrate Salesforce with Gmail” (yes, really—it ranks #1 on Google)

The strategy? They Ask, You Answer.

🥇 Build the Right Team—From the Ground Up

Dakota hires almost exclusively former D1 lacrosse players. Why?

They're resilient. They're coachable. They don't take rejection personally.

🗺️ Cold Email + In-Person Events = Deal Flow

Dakota runs 7:45 AM huddles. Sales reps each name five cities they’re booking meetings in. That framework drives:

• Geographic accountability

• Event scheduling (via Dakota Cocktails)

• Full calendars, fast

Want meetings? Combine offline and online prospecting.

In Summary…

Dakota’s $30B playbook is surprisingly simple:

• Sell Apples to Apple Buyers 🍎

• Content > Cold Calls 📧 

• Build The Right Team 🥇

• Combine Offline and Online Prospecting 🗺️

📞 Want to build a sales-first content engine like Dakota's?

Book a strategy call with Orbit Marketing and let's build your flywheel.

PS: Watch the exclusive interview with Gui on our YouTube channel for the full breakdown.

🤝 Tyler Gillespie: Scale Your Business Using Other People's Audiences

In this episode, Tyler Gillespie, Head of Partnerships & SEO at Beehiiv, shares how service businesses can unlock massive leverage, scale through systems, and tap into other people’s audiences for exponential growth.

In this video, you’ll learn:

• 🔁 Transitioning from One-to-One to Systems-Oriented Models: Why staying in the “client hamster wheel” will stall your growth, and how to break free by productizing your services and simplifying your offers.

• 📈 Consistency as a Growth Hack: Why one traffic source, one offer, one funnel, and 365 days of focus beats 25 scattered ideas, and how Tyler’s “chop wood, carry water” mindset fuels compounding growth.

• 🚀 Activating 3,500 New Partners a Month: How Beehiiv’s partner program skyrocketed from 600 to 3,000+ new signups monthly by reducing friction and dialing in their weekly newsletter dedicated to the partner program.

Enjoying This Newsletter? Here’s Another We Think You’ll Love 👇

Whenever you are ready, here’s how we can help you:

1. Done-For-You Weekly Newsletter - Start a weekly publication to nurture your prospects on auto-pilot, build authority, and stay top of mind. Learn more.

2. Tune Into The Orbit Marketing Podcast - Actionable tips and insights on email marketing, directly from industry leaders. Listen now.

3. Join The Orbit Marketing Partner Program - Learn more about how to partner with Orbit Marketing. Get more info.