• 142: From BlackRock to Boutique, Ellen Bockius of JLAM on Career Pivots, Boutique Building, and Overlooked Markets Big Funds Ignore
    Mar 25 2026

    What do a Notre Dame finance degree, a brief detour into ninth-grade teaching, a Merrill Lynch internship, and 20 years at BlackRock have in common?


    They’re all plot twists on the road to finding exactly where you belong.


    In this episode, Stacy sits down with Ellen Bockius, Head of Business Development & Marketing at JLAM, a boutique real estate investment firm focused on the Mid-Atlantic coast, an area big institutional money often overlooks.

    Ellen shares what it’s like to build a career by raising your hand and moving across businesses… and then suddenly have the “scaffolding” that held your career together at a big shop disappear. She doesn’t gloss over that chapter. She walks right into it.


    Listen in to learn:

    • How Ellen went from “maybe I’m meant to be a teacher” to getting recruited into BlackRock (back when it wasn’t a household name)
    • What it was like to be a right-brained creative in a sea of left-brained people at BlackRock
    • What happens when the company that felt like your identity is suddenly no longer part of your story
    • Why moving from a big shop to a boutique is harder than people think
    • JLAM’s edge: operating experience + overlooked secondary/tertiary markets where big funds won’t even pick up the phone

    This one is for anyone who’s ever wondered if the push they didn’t ask for might actually be the gift they needed.

    More about Ellen Bockius:

    Ellen Bockius is the Director of Business Development & Marketing at JLAM, where she leads investor relations, capital raising, and strategic partnerships. She previously spent 20+ years at BlackRock in senior marketing and client leadership roles, including Managing Director and Head of Institutional Client Marketing.


    A native Delawarean and proud graduate of the University of Notre Dame, Ellen is also deeply committed to education and community service. She serves on the Catholic Diocese of Wilmington School Board and has been actively involved in various industry and philanthropic organizations. When she’s not helping shape the future of JLAM, she’s raising four incredible children with her husband, Troy, her most rewarding and fast-paced role yet.


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

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    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

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    55 mins
  • 141: The VC Model Was Built for Tech. Healthcare Needs Something Else. Buffy Alegria of Loud Ventures on building what’s missing.
    Mar 18 2026

    What if the questions you ask say more about you than the answers you give?

    Two weeks before graduating from college, Buffy Alegria walked into a bank job interview knowing basically nothing about banking.

    But she did walk in with four pages of questions on a yellow legal pad.

    They hired her before she finished the first page.

    That moment set the tone for everything that came after.

    Today, Buffy is the co-founder of Loud Ventures, a healthcare-focused venture capital firm built on a simple (and kind of radical) belief:

    The traditional VC model was designed for tech, and Healthcare doesn’t play by those rules.

    After years in commercial banking, negotiating remote work way before it was normal, raising a women’s health fund entirely virtually during COVID, serving on a rural health board for more than a decade, and learning firsthand (as a patient) what happens when systems break down… Buffy and her co-founder Navin decided to build something different…

    Venture capital for healthcare, by healthcare.

    In this episode, you’ll hear:

    • The interview move that changed her trajectory (and why four pages of questions is a power play)


    • How she negotiated remote work postpartum before remote work was a thing


    • What it was really like raising a women’s health fund as a first-time manager… on Zoom… during COVID


    • Why “underserved” isn’t a buzzword at Loud Ventures (women’s health + rural health as a serious lens, not a niche)


    • What it actually means to be loud and active beyond the check


    • A real-world example of innovation meeting reality: pediatric anesthesia in dental offices, reimbursement pathways, and why “great idea” isn’t enough


    • Buffy’s diligence philosophy: why qualitative signals like curiosity and adaptability can matter more than early numbers

    If you’re building in healthcare (or allocating to it), this one will make you think differently about what “good” looks like.


    More about Buffy Alegria:

    Buffy Alegria doesn't just invest in healthcare: she's lived it. From the NICU to the boardroom, her path through banking, women's health venture, and hospital governance taught her that real progress takes more than a check.

    As Managing Partner of LOUD Ventures, she’s proving that healthcare venture can be done differently by building alongside founders with capital, clinical depth, and operational grit.


    When she's not building the future of healthcare, she's skiing, hiking, or water skiing in the Pacific Northwest with her two dogs. Oh, and wearing her newest hat: dedicated college campus road-tripper cheering on her athlete daughters.



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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

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    1 hr and 13 mins
  • 140: From the other side of the bond desk to $270M AUM. Meet Sweta Singh, Co-Founder of City Different Investments.
    Mar 11 2026

    What if the secret to building a firm people know, like, and trust wasn’t a slicker pitch deck… or a better track record?

    What if it was the audacity to just be yourself?

    Sweta Singh didn't wonder. She just built it.

    Before she was a founder, she was on the other side of the desk entirely, issuing bonds for the State of New York, watching how public money moves through communities, hospitals, schools, and retirement funds. Most portfolio managers never see that side. Sweta did. And she never forgot it.

    Twenty-five years later — Wellington, Income Research, Thornburg — she took the leap. City Different is what happened next.


    In this episode, Stacy Havener sits down with Sweta to talk boutique building, muni bonds, and why being "boring" in the right part of the portfolio is actually the goal.

    Listen in to hear:

    • Sweta’s backstory – From India to full scholarship to Albany bond issuer
    • How she got hooked on finance (and why the policy/markets/human behavior collision lit her up)
    • What issuing bonds before managing them taught her about how muni debt connects to real voters, real communities, and real consequences
    • The City Different origin story: why the name is a love letter to Santa Fe (and a reminder to stay different)

    More about Sweta Singh:

    Sweta Singh is a fixed-income portfolio manager and co-founder of City Different Investments, with more than 25 years of industry experience. Her desire to constantly learn and adapt has been her greatest gift, and the thread that connects every chapter of her career.

    After immigrating to the U.S. and earning degrees from the University of Massachusetts (summa cum laude), the University of Texas at Austin, where she was awarded the Barbara Jordan Fellowship, and SUNY, she began her career in New York State's Debt Division, learning every aspect of bond issuance from the ground up.

    That other-side-of-the-desk foundation carried her through roles at Wellington Management, Income Research and Management, Breckinridge Capital Advisors, Thornburg Investment Management, and Wilkins Investment Counsel, building expertise across municipal bonds, corporate credit, agencies, and treasuries along the way.


    Sweta believes investing is dynamic and that its future belongs to the best of both human and machine. It's a belief she brings to life every day at City Different Investments.


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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

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    1 hr and 9 mins
  • 139: She dealt blackjack to pay for college. Now she runs a $5 trillion company. Meet Orion CEO, Natalie Wolfsen.
    Mar 4 2026

    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

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    1 hr and 4 mins
  • 138: What to Say When Allocators Ask “What Makes You Different?” | Story Snacks Series
    Feb 25 2026

    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.


    ---
    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

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    10 mins
  • 137: How to Keep Your Story Fresh in 2nd + 3rd Meetings | Story Snacks Series
    Feb 18 2026

    “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

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    11 mins
  • 136: Founder First, Team Second (Here’s Why) | Story Snacks Series
    Feb 11 2026

    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

    ---
    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

    Show more Show less
    9 mins
  • 135: Be the Jimmy Fallon: The Secret to Meetings That Don’t Go Off the Rails | Story Snacks Series
    Feb 4 2026

    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

    Show more Show less
    15 mins