Our First Check Wasn’t a Startup (April '26)
Note from the Founders 👋
The Girl Math of Alternatives: Getting Real with Real Estate 🏠
Deal Spotlight: WhatIf Legal ⚖️
Investor Resource: How to Use Claude More Effectively 💻
Media & Press: Investment Banking to Startup Founder 🎧
What's Coming Up: Whole Health Summit 🧠
Note from the Founders 👋
GM ☕ from Serena, Porter, and Emma, the co-founders of Girl Math Capital! Last newsletter, we tested out a new writing style where we leaned into personal updates and a more conversational tone of voice, and we got stellar feedback from you (team NO AI SLOP!!!). We always appreciate hearing what kind of content resonates with our audience, because ultimately, we want to write things that you all can learn from, but also have fun reading.
With that, here’s what we’ve been up to this month: Emma just crossed the finish line at the Boston Marathon with a new PR (it'll be another few days before she can walk normally up the stairs again, but she earned every bit of it 🎉). Serena wrapped up Wharton’s Venture Lab Accelerator, VIP-X, with a stellar demo day presentation, and is now studying for exams (LOL) before diving into full-time GMC work this summer (!!!). Porter is somewhere between her last ski run in Sun Valley (maybe still recovering from yeeting off a jump on her Instagram story 😂), a crypto conference in NYC, and back home in Austin before she's off again. We’re in awe of her energy and slightly exhausted just reading her calendar.
Meanwhile, things have been cooking at Girl Math. Since our last newsletter, we've closed not one but two SPVs, which means our members have been writing checks, and we've been doing the work to make sure those checks can be a part of those rounds. If you've been watching our deal flow from the sidelines, consider this your nudge to join us for Cohort 4 😉.
We're also deep into the Real Estate unit of Cohort 3, which felt like the perfect excuse to dedicate this month's newsletter to one of our favorite asset classes. Real estate has been part of Girl Math's DNA since literally day one, and we can't wait to tell you that story today.
Happy reading! 💸
The Girl Math of Alternatives: Getting Real with Real Estate 🏡
Read time: 6 minutes
Before we were running SPVs into Ghia and OpenAI, our very first deal at Girl Math Capital was a house flipping opportunity in Louisville, Kentucky.
It was the fall of 2024 during our pilot cohort, and our Vanderbilt friend and early GMC supporter Ammar Ahmed - the co-founder and managing partner of real estate fund Strand Bridge - brought us an opportunity most of our members had never considered before. It wasn’t a stock, mutual fund, or a startup. It was a single-family home that needed a full renovation in order to be sold. The developer was looking for financing via short-term lending, which Strand Bridge was providing. Ammar generously offered GMC members the opportunity to invest in the opportunity alongside him, even though our checks were smaller than the typical real estate deal LPs.
That deal introduced our earliest members to something powerful: you do not need to buy a property to invest in real estate.
Now that we've moved into our Real Estate unit in Cohort 3, we wanted to dedicate this month's newsletter to breaking down how this asset class works, because if you've ever thought “I want real estate exposure but I'm not trying to become a landlord,” this one's for you.
1. Debt vs. Equity: Know What You're Buying Into
The first thing to understand is that when most people think about real estate investing, they picture owning the property: being the landlord, collecting rent, dealing with a broken pipe at 11 pm 🥴. That's equity investing: you own a piece of the asset, you share in the upside (and the downside).
The other way in is debt investing. This is what the Strand Bridge deal was. Instead of owning the property, our members were acting as the lender. Ammar's business provides short-term loans (called hard money loans) to experienced home flippers who need fast capital to purchase and renovate properties. Investors typically earn a fixed 9% annual return, paid out monthly as interest distributions, with capital returned at the end of the 6-month period.
As a debt investor, your return is fixed and your position is more protected - you're earning a set rate regardless of what the house sells for. The tradeoff is that you don't participate in any extra upside if a buyer swoops in with a bid way higher than expected and impossible to say no to. It's a different risk profile, and for a lot of people - especially us, who were just getting into investing at that point - a much more approachable entry point.
2. The Landscape: More Ways to Access Real Estate Than You Think
The Strand Bridge deal is one example of the many ways you can get real estate exposure without a mortgage. Here's a quick lay of the land:
Hard money lending / private credit (like the Strand Bridge deal) - you're the lender, earning fixed interest on short-term real estate loans. Lower minimums, shorter time horizons, monthly cash flow.
Real estate syndications - a GP (general partner) pools capital from multiple investors to acquire a larger asset (think apartment complex or commercial property). You're a passive LP, earning distributions and a share of the upside at exit. Similar structure to the SPVs you've seen in our angel unit.
REITs (Real Estate Investment Trusts) - publicly traded funds that own income-producing real estate. You can buy them through any brokerage account like a stock. Highly liquid, but you trade some control and upside for that accessibility.
Crowdfunding platforms (Fundrise, Arrived, etc.) - lower minimums, passive, but generally illiquid. A good on-ramp if you want exposure with limited capital.
The common thread between all of these is that someone else is doing the operational heavy lifting, but you’re able to participate in the asset class. You might not have the time to manage a property, the money to make a purchase, or a combination of both. These strategies let you get in at a lower price point for your time and your pocket.
3. Why Real Estate Belongs in Your Portfolio
A lot of our investments have been in high risk, high return companies, where the time horizons for capital returns are uncertain and long term. With real estate, however, you can expect a very different set of benefits than early stage startups.
Monthly cash flow. Unlike most early-stage startup investments (where you're waiting years for a potential exit), many real estate vehicles pay along the way. The Strand Bridge deal paid us interest every single month.
Uncorrelated to the stock market. Real estate values and returns don't move in lockstep with the S&P 500, which means it can stabilize your overall portfolio during market volatility.
Inflation hedge. Real assets tend to hold their value (and then some) in inflationary environments. Rents go up, replacement costs go up, and so do property values over time. Bad for your monthly rent in NYC, good for your real estate portfolio.
Attractive in a high-rate environment. Higher interest rates have cooled parts of the real estate market, but they've actually made debt vehicles like hard money lending more attractive; borrowers pay higher rates, which means lenders earn more.
Tax advantages. One of the reasons real estate remains such a popular wealth-building tool is that the tax code tends to reward ownership. Rental income can often be offset by expenses like mortgage interest, property taxes, insurance, and repairs, which can reduce taxable income. There’s also depreciation, a non-cash deduction that lets investors write off the value of a property over time, even if it may be appreciating in market value. When it comes time to sell, strategies like a 1031 exchange can allow investors to defer capital gains taxes by rolling proceeds into another property.
The Takeaway
Real estate is one of the oldest wealth-building tools in the book, but when we started Girl Math, it felt inaccessible to a group of young women without a down payment or a real estate license. The reality is that the landscape has changed, and the structures that have existed in institutional investing for decades are now available to everyday investors.
We started with a house in Louisville, but we are constantly looking for new real estate deals for our members. If you have real estate opportunities that you think might be a fit, we’d love if you shared them with us via our pitch form. And if you’re selling a villa in the French countryside, we’ll gladly take it off your hands and turn it into a Girl Math retreat (the girls can dream 💭🏡).
We're also incredibly lucky to have Liz Faircloth and the Real Estate InvestHER team as a resource for our community as we go deeper into this asset class. They're on a mission to empower women to build wealth through real estate, and they just led our second Real Estate session for Cohort 3. If you want to keep learning, they're a great place to start.
Deal Spotlight: WhatIf Legal ⚖️
ICYMI: Each month, we'll share a few of the deals our community has backed, not to give investment advice, but to show you the breadth of opportunities Girl Math members are exploring and spotlight some epic founders.
Lilli Donahue is a great friend, motivated entrepreneur, event co-host, and guest speaker to GMC. But before any of that, she was someone I (Emma) sat next to at a lunch hosted by mutual friend, Alex Chung.
We got coffee almost immediately after, and and from our first real conversation, it was clear she was building something deeply personal. Her parents went through a six-year divorce without a prenup that ended in bankruptcy and eviction. That experience is the origin of WhatIf, and the way she tells it has a way of making you feel the mission before she ever gets to the product.
That November, Lilli joined us for a prenup education session that our members still talk about. When she came back in February to pitch, it felt like a full-circle moment, and not one, but five (!) Girl Math members wrote checks.
WhatIf Legal is an AI-powered assistant for family lawyers that automates client intake, integrates financial data, and generates attorney-ready draft agreements, making prenups faster for lawyers and more accessible for couples. Prenups are just the wedge; the same architecture extends into postnups, wills, trusts, and broader estate planning.
GMC member Nikki Nissan invested because she was moved by Lilli's “why” - “her conviction to empower others through education around a traditionally taboo topic”, and her drive to “rethink a process that's long overdue for change.”
WhatIf came out of stealth this month, and the best is yet to come. Follow WhatIf on Instagram, and check out the Prenup Podcast here.
Investor Resource ✏️
How to Use Claude More Effectively: Notes from Our Anthropic Round Table 💻
Not technically an investing resource this month, but we wanted to share some takeaways from our most recent Round Table, a monthly series where our members lead discussions around the relevant investing and professional topics. Considering how much Slack banter we’ve been seeing around AI, we figured we’d let the experts, Rads Mehta from Anthropic and Becca Wihl at Google, give us the inside scoop.
AI Fluency
Rads opened with a framework she calls AI fluency. The idea is that getting value from AI is less about knowing every new feature and more about building a smart relationship with the tool. Four D’s:
Description: Define what you actually want.
Discernment: Evaluate the output, and do not take it as fact.
Delegation: Decide what is worth handing off.
Diligence: Make sure the final product is actually good.
Claude is predicting the next most likely word based on patterns; it is not “thinking.” So the quality of what you get back usually comes down to the quality of what you give it.
Which Product Should You Use?
Claude Chat: Everyday use. Writing help, brainstorming, research, summaries, quick questions.
Co-work: Multi-step tasks that need real output, like decks, spreadsheets, planning, recurring workflows, automations.
Claude Code: Building things. Apps, tools, agents, prototypes.
Not sure which to use? Ask Claude which tool makes the most sense for the task.
Prompting Better
Give Claude a role. The more precisely you define the perspective, the more useful the output. (e.g. "Act as an experienced angel investor who specializes in CPG and has evaluated hundreds of early-stage deals.").
Provide context around goals, audience, budget, timeline, tone, etc. (e.g. "I'm evaluating a pre-seed [sector] startup. Here's their pitch deck / one-pager / what they told me: [paste it in]. My main concern going in is [X]. I'm trying to decide whether to take a second meeting / write a check / pass."
Tell it what kind of output you want - a structured memo, a quick gut-check, a list of questions, a red flag scan. (e.g. Give me a structured evaluation covering team, market size, moat, business model, and risks. Flag anything that would be a dealbreaker for a [sector] investment. Then give me the 5 sharpest diligence questions I should ask the founder in my next call.)
Iterate. This is where most people stop too early. After the first output, ask probing questions (e.g. "What are you most uncertain about in this evaluation?", "What would have to be true for this to be a great investment?", "What's the bear case?" or "What questions did I not think to ask?")
For this example, here’s the full prompt in one shot:
"Act as an experienced angel investor who specializes in [sector]. I'm evaluating a pre-seed startup - here's what I know: [paste materials]. My main concern is [X]. Give me a structured evaluation covering team, market size, moat, business model, and key risks. Flag any dealbreakers. Then give me the 5 sharpest questions to ask the founder. Be direct - I want your honest read, not a balanced summary."
The last sentence matters more than it looks. Claude defaults toward balanced, hedged analysis. Explicitly asking for a direct, honest read pushes it to actually take a position rather than list pros and cons and leave the conclusion to you.
Other Example Use Cases from our Presenters
Rads runs a scheduled task every day at 5 pm that scans her inbox, flags priority emails, and drafts responses automatically.
Becca built a GMC-specific investment diligence Project that she uses to inform her investment decisions. She loaded in her investment thesis, organized questions by bucket (market, team, business model), and added sector-specific red flags.
She also helped a friend build a full wedding planning framework in Notion using Claude - automating everything from task management to seating assignments to website FAQ updates.
We love an AI agent with depth 🤓🫰💍
For more tips like this, consider joining our next cohort!
Media & Press: Investment Banking to Startup Founder 🎧
This month, Emma sat down with Karen Elders on the Launch Career Strategies podcast to share her journey from her first investment banking role at Bank of America, to Uber, to starting a community for women in alternative investing. Listen on Spotify or Apple Podcasts, and let us know what you think!
If you're a young professional navigating your career path, Karen and her team are worth knowing. They offer 1:1 coaching on everything from resume and LinkedIn optimization to interview prep and networking strategy, and you can book a free 15-minute consultation here.
What's Coming Up: Whole Health Summit 🧠
For our community members, we have two events coming up next week in NYC - check our Slack or the GMC calendar for details 🍎.
For all of our readers, Emma will be speaking at Luminary's Whole Health Summit on May 14th in NYC (also available virtually). It's a full-day event covering women's health across the physical, mental, financial, and professional spectrum - the kind of day that leaves you feeling like you can tackle anything. Tickets are available in-person and virtually here. Come say hi! 👋
Lastly, follow us on LinkedIn, Instagram, or TikTok so you don't miss a thing.
Closing Note 💌
Girl Math Capital was born from the frustration that deals were shared in some circles and not in others. This newsletter is one more way to make sure those conversations and opportunities reach more people, and in particular, more women. If you know someone who'd love this newsletter, pass it along. We believe alternative investing isn't just for finance and tech bros - it's for women who want to get smart, build community, and build generational wealth. See you next month 💸💅
The Girl Math Team
If this got you curious, submit your information to join our next cohort, or apply to be a community member here
