Most CEO stories start with an Ivy League credential and a tidy career ladder, but this one starts with a blackjack table.

Before Natalie Wolfsen was running Orion, she was dealing cards to pay for college. At the time, she had no idea that the lessons she was learning on that casino floor would follow her all the way to the C-suite.

In this episode, Natalie opens up about the chapters that don't fit neatly on a résumé and why she believes those are often the most important ones.

Listen in to hear:

• How she parlayed casino marketing into a career in finance
• Why she walked away from a thriving role at American Express to try entrepreneurship
• The startup that failed in 8 months and why she'd do it again in a heartbeat
• How saying yes to "inconvenient" opportunities compounded into a career she never could have planned

More about Natalie Wolfsen:

Natalie Wolfsen joined Orion Advisor Solutions as CEO in October 2023 and is a member of the firm’s Board of Directors. She is the former CEO of AssetMark and has nearly 30 years of financial services industry experience. For over 25 years, Natalie has served independent advisors (RIA and broker-dealer affiliated) with more than a decade of working with independent and insurance broker-dealers. Prior to joining AssetMark in 2014, Natalie previously held digital and investment platform development, investment solution management, strategy and marketing roles at First Eagle Investment Management, Pershing, Charles Schwab and American Express. Natalie has an MBA from University of California, Los Angeles and a Bachelor of Arts degree from University of California, Berkeley.

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Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap

Every allocator asks: “What makes your boutique different?”

And most fund managers default to something like, “Our people are great!” or “Our process is best-in-class!”

Which is fine. It’s just… also what everyone else says.

In this episode, Stacy explains why saying “We’re better” in meetings won’t do you any favors and why being different (even if it’s uncomfortable) is the best way to stand out to allocators.

Listen in to learn:

• Why you don’t want to make up differentiators in the moment

• Why trying to be polite is the fastest way to blend in and be forgotten

• The Truism Test (a fast way to spot a “differentiator” that’s actually table stakes)

• The prompt that reveals where you’re out of consensus with your peers (and why that’s your edge)

• Why the best differentiator often takes a little courage to say out loud

This is Story Snacks, a bite-sized, jam-packed series for fund managers who are ready to master strategic storytelling in under 20 minutes a week.

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Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap

“Ugh… I’m going to sound like a broken record.”

If you’ve felt that in a 2nd or 3rd meeting, you’ve probably had the urge to “freshen up” your story just to keep it interesting.

In this episode, Stacy breaks down why that instinct can backfire.

She’s digging into what actually matters in follow-up meetings, especially when new people join, when the sales team thinks “we already covered that,” and when you’re tempted to improvise a whole new version of your story.

Listen in to learn:

• Why “repetitive” might be a you problem (not a them problem)
• Why you don’t want your story to shift too much between meetings
• The simple test for whether you should “run it back” (even in a 3rd meeting
• How to tee up repetition without it feeling awkward

This is Story Snacks, a bite-sized, jam-packed series for fund managers who are ready to master strategic storytelling in under 20 minutes a week.

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Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap

Most founders lead with the team because they’re trying not to sound egotistical.

But allocators aren’t sitting there thinking, “Wow, great org chart.” They’re thinking: “Do I understand this firm yet?”

In this episode, Stacy breaks down what allocators actually want in the first meeting and why you’re better off leading with a crisp origin story (even if the founder isn’t in the room to tell it).

Listen in to learn:

• How to tell the founder story without it sounding like “me, me, me”

• What to do when you’re not the founder (or the founder isn’t there)

• How co-founders/co-managers can stay aligned on one clear version of the story

• Where to place team so it builds trust instead of overwhelming the opener

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Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap

If your meeting goes off the rails, it’s not because your prospects are “unruly.” It’s because no one’s driving.

And with the right moves, you can take the wheel fast without making it weird.

In this episode, Stacy breaks down how to prevent unhelpful tangents before you ever walk in the room (hello, champion prep call) and what to do in real time when someone hijacks the conversation.

Listen in to learn how to:

• Prep with your champion so you walk in knowing who’s who in the zoo (and who might go rogue)

• Use a simple meeting prep doc so everyone stays aligned on the goal, flow, and roles

• Redirect tangents — whether they come from the prospect or your fund manager — without anyone feeling embarrassed (we don’t kick people under the table around here)

• Be the Jimmy Fallon of the meeting who breaks the ice and keeps things moving without making it awkward sauce

This is Story Snacks, a bite-sized, jam-packed series for fund managers who are ready to master strategic storytelling in under 20 minutes a week.

---
Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap

Ever felt the urge to tidy up your story before sharing it? You scan the room, see the impressive bios and the blazers, and think: “Oof... maybe I should skip that part.”

You’re not wrong for feeling that way, and you’re definitely not the only one.

In this episode, Stacy opens up about her London panel debut, where she felt that pull to edit out the messy parts of her story on the fly. She’s explaining why she chose to dig in her heels and tell the raw version, even though it was nerve-racking (and why she recommends you do the same).

Listen in to learn:

• Why you shouldn’t prepare multiple versions of your story, pitch, or deck for different crowds
• How to adjust your story to fit the room without sacrificing authenticity and clarity
• The “still me, just work-me” approach that will help you tweak your delivery without losing the vulnerable parts of your story that make you memorable

This is Story Snacks, a bite-sized, jam-packed series for fund managers who are ready to master strategic storytelling in under 20 minutes a week.

---
Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap

If you’re still following the traditional sales funnel framework in 2026, your firm’s growth is sure to stall.

Because the “inverted triangle” view of a funnel is oversimplified, and it’s starting to feel like the fundraising version of that tired investment process slide that makes everyone want to poke their eyes out.

It flops because not everyone in your funnel needs the same thing, and “just checking in” isn’t a follow-up strategy that actually moves people forward.

That’s why in this episode, Stacy’s breaking down what actually works to keep your funnel healthy.

Listen in to learn:

• Why the funnel isn’t a simple inverted triangle (and what it really looks like in practice)
• What people at the top, middle, and bottom of the funnel actually need from you
• The real job of the middle of the funnel (and why most teams ignore it)
• Why filling the top of the funnel is harder than closing deals
• Creative ways to get in front of new prospects (without spammy outreach)
• Why LinkedIn works so well for this when you share the right kind of content

This is Story Snacks, a bite-sized, jam-packed series for fund managers who are ready to master strategic storytelling in under 20 minutes a week.

---
Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap

You thought you nailed the meeting. The conversation went well, heads were nodding, and everyone seemed engaged. Then you followed up with a thoughtful email and… crickets.

Or maybe you got hit with the four words every fund manager dreads hearing: "We’ll watch you."

Most people take either of those as signals to retreat and move on. But what if they're actually something else entirely?

In this episode, Stacy explains why hearing "no" (or radio silence) doesn't always mean your deal is dead.

She's also sharing the high school soccer philosophy that changed how she handles rejection in sales, plus the exact move that turned a "we'll watch you" into a $50 million yes.

In this episode, you'll learn:

• What "maybe" really means and why it's probably not what you think
• How to spark the honest conversation that could actually save the deal
• A meeting-prep strategy that helps you avoid ghosting before it ever happens

This is Story Snacks, a bite-sized, jam-packed series for fund managers who are ready to master strategic storytelling in under 20 minutes a week.

---
Running a fund is hard enough.
Ops shouldn’t be.
Meet the team that makes it easier. | billiondollarbackstory.com/ultimus

- - -
Thinking about expanding your investor base beyond the US? Not sure where to start? Take our quick quiz to find out if your firm is ready to go global and get all the info at billiondollarbackstory.com/gemcap