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Lately, I’ve been thinking about how connection compounds — especially when it happens in person.

After years of virtual meetings and digital everything, the feedback has been clear: people miss being together. The energy, the ideas, the serendipity — it just hits different when you are in the same room.

You’ll see I have a few events cooking up under the Bear and the Bull banner, from art and capital in Los Angeles to proptech and innovation in Austin to casual happy hours when I’m on the road. Each one is designed to bring founders, investors, operators, and creatives together in real life — to exchange ideas, share stories, and spark new collaborations.

More to come, but I am excited to keep building this community and platform — one gathering at a time.

But first, an important piece of advice for founders deep in the throes of pitching. Read on to avoid these common fundraising pitfalls.

I’ve reviewed thousands of decks and worked with some of the biggest brands in the world. And yet, I could shout “storytelling” from the rooftops, and most teams still would not get it.

Founders often spend weeks perfecting their pitch deck design, tweaking product screenshots, or memorizing TAM/SAM/SOM numbers—but miss the single thing that truly moves investors: clarity.

Clarity of story. Clarity of purpose. Clarity of vision.

The irony is that early-stage investors are not just betting on what you are building—they are betting on you. Your ability to communicate why this company should exist, why now, and why you are the person to build it is what gets people to lean in.

To help early-stage founders avoid the same pitfalls, here are three of the biggest red flags I see over and over again—and how to fix them.

1️⃣ Rushed timelines.

Somewhere along the way, “create urgency” became startup gospel. But when a founder says, “we’re closing the round in a week,” I almost always pass.

Not because I do not believe in the business, but because conviction takes time. Real diligence—customer references, market validation, founder references—cannot happen in days. Venture capital is a long-term relationship business, and compressed timelines often signal misalignment or desperation rather than momentum.

If you want serious investors at the table, give them space to build conviction.

2️⃣ Lack of coachability.

At the pre-seed and seed stages, nothing goes exactly to plan. The best founders are adaptable, self-aware, and able to separate useful feedback from noise.

Coachability does not mean saying yes to every suggestion. It means being able to listen, ask smart questions, and pivot when evidence demands it. Investors pay attention to how you respond when challenged—it often tells us more than your traction slide ever could.

3️⃣ Overemphasis on product.

Your product matters—but your story sells.

I see too many technical founders who can demo every feature yet struggle to articulate why it matters or who it serves. Customers, employees, and investors all buy into your why long before they fall in love with your what.

At the earliest stages, clarity of narrative often outweighs technical depth. Know your product cold—but lead with your vision.

That is also why I started my narrative consulting practice: to help founders tell their story clearly and confidently. If that sounds like something you or someone you know could use help with, just reply to this email.

Great storytelling does not replace execution—it amplifies it. The founders who win investor conviction are not always the ones with the flashiest tech, but the ones who can clearly connect the dots between mission, market, and momentum.

If you know a founder who needs to hear this, forward this newsletter their way.

Why they matter: Armand, the founder of Redii, is building a global savings infrastructure that allows distributed teams to manage long-term savings and retirement benefits across currencies and jurisdictions. I have known Armand for more than a decade and could not be more excited about what he is building. After seeing firsthand the cracks in pension systems like Australia’s, it is clear that strong mandates do not always translate to strong outcomes. Redii’s model challenges that complacency by creating a more transparent, performance-driven framework for global retirement savings.

The opportunity: The global pensions and workplace savings market represents more than $60 trillion in assets, yet the systems that govern it were not designed for remote and cross-border work. Redii is positioned to capture a growing share of the $1.5 trillion in annual cross-border payroll and benefits flows by offering employers a unified, portable savings infrastructure. Its model bridges fintech and HR tech, creating the connective layer for a workforce that is increasingly global, mobile, and digital-first.

If you would like to connect directly with founders building the next wave of best-in-class fintech and retirement infrastructure startups, email me for my exclusive founder directory and gain early access to introductions and insights from across the Bear and the Bull network.

🖊️I explored how fintech platforms like Percent and Exaloan are reshaping retirement investing. By digitizing private credit and introducing transparency, shorter durations, and lower minimums, these companies are bringing an institutional asset class to individual investors. If you want a visual guide on how to move from feature to product, reply to this email.

👉 Read on Forbes

💭 I spoke with Nelson Chu, founder of Percent, on why trust—not speed—is the ultimate moat in fintech. Last time, I featured Claire Coder of Aunt Flow, who’s redefining workplace dignity. Both are reimagining systems we rely on every day, from finance to facilities.

👉 Upgrade to paid subscriptions for exclusive Q&A, events, and deal sharing

🎧 I released my first Spanish-language episode with Ximena Alemán, founder of Prometeo, to kick off the new Multilingual Money Memories series.
👉 Listen on NPR, Apple, Spotify, or wherever you listen to podcasts

If you know me, you know I love getting people together and seeing sparks fly. I’m excited to kick off two incredible events under the Bear and the Bull umbrella this December — partnering with some really great people along the way.

If you’re interested in sponsoring an upcoming event or collaborating on future gatherings, I’d love to work with you. Just reply to this email and let’s chat.

🎨 Culture + Capital | Los Angeles | December 3

An evening at the intersection of art, wealth, and creativity. Join us for Culture + Capital, a gathering that invites investors, founders, creatives, and culture lovers to explore what artistic practice can teach us about long-term value creation.

Who it’s for:
Anyone curious about how creativity shapes capital — from investors and entrepreneurs to artists, collectors, and design enthusiasts.

What to expect:
A private gallery walk featuring handmade scrolls by a renowned Chinese artist, followed by a hands-on workshop where guests will create their own scrolls.

Where: Santa Monica, CA
When: December 3 | 6:00 PM – 8:30 PM

RSVP Here

How Proptech is Reshaping Real Estate | Austin | December 4

Technology is transforming how we live, lease, and invest. Join us for How Proptech is Reshaping Real Estate, a conversation bringing together investors, founders, and operators driving innovation across the built world.

Who it’s for:
Real estate professionals, proptech founders, venture investors, and anyone curious about how data, AI, and design are reshaping the future of property.

What to expect:
Hosted in partnership with Joanna Hackney of Linea, this discussion features Jeff Hurst, CEO of Furnished Finder, and other leaders at the intersection of real estate and technology. The Austin event marks the kickoff of “Built In,” a new global series exploring how innovation takes shape in cities around the world that I am proud to partner with Linea on.

Where: Austin, TX
When: December 4 | 6:00 PM – 8:30 PM

Other happenings

📌Women’s Pay Is Falling Behind. Is the Return to the Office to Blame?

📌Laura Loomer’s Endless Payback

If you find this valuable, here are a few ways to support Bear and the Bull (most of which are free):

Till next week,
Ilona

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