- Girls Into VC
- Posts
- The VC Playbook
The VC Playbook
Strategic thinking for aspiring investors + upcoming webinar!
🚀 Upcoming Webinar: Picking the Right Rocket Ship
We’re so excited to announce our next Girls Into VC webinar
Choosing the right startup can define your early career—but how do you know which one is the right bet?
Join us for a conversation with Andrea Corleto, the first hire at Skylight who helped grow the company from $2M to $200M in revenue, scaled it across 34 countries, and served as VP of Growth and GM of International. Now a founder building a female-first longevity startup, Andrea will share her insights on:
How to evaluate early-stage startups
What red flags to look out for
What she learned scaling a company from scratch
What she wishes she knew before joining
This is a must-attend session for anyone thinking about joining a startup—or dreaming of founding one someday.
GIVC Fellowship Session Highlight: Go-to-Market Tech & AI Investing with Maha Malik (Bessemer Venture Partners)
Maha Malik, an investor at Bessemer Venture Partners in NYC, focuses on vertical AI, SaaS, and consumer AI applications, especially within early-stage startups. Drawing from a decade in consulting and dual graduate degrees from Harvard Business School and Harvard Kennedy School, she brings a structured, impact-driven lens to venture capital.
During a discussion on Go-to-Market technologies, Malik emphasized the importance of tools like ChatGPT and Claude for early-stage teams, especially in content generation, research, and strategic planning. Survey insights highlighted ChatGPT as the most commonly used GTM tool due to its flexibility across tasks from sales call prep to data analysis.
🧠 Her Key Investment Insights:
Product > Founder: Malik prefers to evaluate product traction and user value over personality-driven founder narratives, warning against bias in the “founder-first” mentality.
Organic growth is the signal: Her analysis of two decades of Bessemer deals revealed that word-of-mouth-driven growth is the most predictive sign of long-term success.
Efficiency beats hype: She’s skeptical of capital-heavy fundraising, noting that the best startups often scale profitably with minimal burn, especially in AI.
Defensibility in AI: comes from execution, integration, and deep user understanding not just proprietary models.
🧭 Advice for Aspiring VCs & Builders:
For aspiring VCs: Develop sourcing differentiation and deal judgment. Learn to recognize early traction, commercial efficiency, and retention. Tools like ChatGPT can accelerate your learning curve.
For consultants: Use the industry to build conviction and get comfortable making decisions with incomplete information.
For mission-driven professionals: Combine impact and innovation by becoming a founder, joining an impactful team, or investing with values in mind.
Main Takeaway: The best startups don’t need a lot of money, they need deep user understanding, sharp execution, and the ability to build fast
👋 From Our Team
This week we’re unpacking investment strategies in venture capital not just by stage and fund size, but in how deals are structured. Tools like SAFEs, convertible notes, and tranches shape when and how capital flows, helping demystify venture dealmaking for aspiring investors or founders.
Understanding the Landscape: VC Investment Strategies
📈 Stage‑Based Strategies
Seed and Pre‑seed – Small checks, often via SAFEs or convertible notes—fast and flexible.
Series A–C (Growth) – Priced equity rounds with detailed term sheets, preferred shares, board seats.
Late‑stage / Mega‑rounds – Strategic/institutional investors backing high‑traction companies with complex valuation and governance.
🧩 Deal Structure Mechanics
SAFEs – Early‑stage, YC‑launched, convert into equity at priced round with cap + discount, no maturity date.
Convertible Notes – Debt that converts later, with interest and maturity timeline.
Tranches – Disbursed in stages based on milestones; common in biotech/deep tech.
Pro‑rata Rights, Liquidation Preferences, and Pari Passu - terms further refine investor protections and return dynamics.
🏆 Top 3 VC Mega‑Rounds
🧠 Deal Deep Dive: Databricks’ $10B Series J
Just two months after OpenAI’s October raise, Databricks set a new record for a priced equity round, raising $10 billion in December 2024 to accelerate its AI-native data infrastructure.
Company: Databricks - Provides a unified data and AI platform (based on Apache Spark and “lakehouse” architecture) that helps enterprises process, analyze, and deploy AI on massive datasets.
Amount Raised: $10 billion (December 2024)
Valuation: ~$62 billion post-money
Lead Investor: Thrive Capital
Others: Andreessen Horowitz, Iconiq, Insight Partners, Ontario Teachers’ Pension Plan
Structure: Priced equity (Series J)
🔸 What Made This Deal Unique?
Clean Term Sheet
Unlike other mega-rounds, this was a straightforward priced equity deal, reflecting Databricks’ maturity.
AI-Native Infrastructure Focus
The raise was driven by customer demand for AI model integration.
IPO Optionality
This raise gave Databricks runway to delay a public offering while expanding aggressively.
💡 Why It Matters
Databricks proved that traditional equity rounds can still scale to $10B+ when enterprise traction is strong. The company’s infrastructure-first AI position made it a core pick for long-horizon capital.
🧠 Deal Deep Dive: OpenAI’s $40B Super-Round
Less than six months after its $6.6B raise, OpenAI stunned the market again in April 2025 with a $40 billion round, the largest VC deal of all time.
🔸 What Made This Deal Unique?
Record-Breaking Size
This was nearly 4× larger than any previous venture round, redefining what “late-stage” means.
Multi-Tranche Release
Capital is unlocked in phases based on key milestones like global enterprise growth, model capability, and chip procurement.
Private Round, Public Pressure
Despite raising at a massive valuation, OpenAI retained private status buying time before any IPO.
💡 Why It Matters
This deal wasn’t just big it was bold. Investors structured it to reflect both confidence in OpenAI’s mission and caution around governance risk. It shows how strategic capital now scales beyond traditional IPO timelines.
🧠 Deal Deep Dive: xAI’s $6B Hybrid Round
In December 2024, Elon Musk’s
xAI closed a $6 billion funding round (one of the largest ever in AI) designed to accelerate open-source model development and scale Grok, its real-time conversational assistant.
Company: xAI - Elon Musk’s generative AI startup focused on building real-time, conversational AI systems (like Grok), with a mission to develop “truthful” open-source general intelligence.
Amount Raised: $6 billion (December 2024)
Valuation: ~$45 billion (estimated)
Lead Investor: Andreessen Horowitz
Others: Fidelity, Valor Equity, Lightspeed, Sequoia, Morgan Stanley, Saudi VC, Nvidia
Structure: SAFE + tranches, milestone-based investment
🔸 What Made This Deal Unique?
SAFE Structure
The first $3B of capital came in via SAFEs with valuation caps and discounts, common in early growth rounds for speed and flexibility.
The remaining $3B was tied to adoption and technical benchmarks, including user growth for Grok and next-gen model release cadence.
Founder-Led Conviction
Elon Musk’s direct involvement helped secure major institutional support, despite the early-stage nature of the business.
💡 Why It Matters
This was one of the clearest examples of a hybrid AI financing: flexible capital up front, tied to strong conviction in Musk’s vision, and tranches structured to reduce risk for investors. It underscored how founder-brand and milestone alignment can shape mega-round design especially in mission-driven or technically ambitious startups.
Full Time Roles:
🔭 Telescope Partners: Associate (SF-Based Office) - Apply Here
🤝 Alumni Ventures: Senior Associate + Partner Roles (Boston + NY) - Apply Here
Internships:
🐎 Pegasus: Fall Venture Researcher - Apply Here
🪷 Alumni Ventures: Summer Analyst (New York) - Apply Here
💵 Alumni Ventures: Fundraising Intern (New Hampshire) - Apply Here
Events
🌆 Women in HealthTech Pitch Tank - August 14th (Virtual) - RSVP Here
🏋️♀️ Exercise Try It Yourself: Would You Invest?
💼 The Scenario:
You’re a venture investor evaluating a pre-seed round for Aisha, the founder of Bankless, a peer-to-peer credit app focused on Latin America.
She’s raising $1 million, and you’re excited about the team and vision. But you need to decide which deal structure to go with:
💸 Your 3 Options:
Option A: SAFE with a $6M valuation cap and 20% discount
Option B: Convertible Note with 6% interest, $7M cap, and 24-month maturity
Option C: Tranche structure: $500K now, $500K after hitting 50K users, at a $5M pre-money valuation
❓Your Task:
Which structure would you choose and why?
🧑🎓 What’s the “Right” Answer?
Option A (SAFE) is simple, clean, and widely used for early-stage deals. It’s friendly to both founders and investors, and avoids debt-related complexity.
Option B (Convertible Note) offers downside protection through interest and maturity, but adds legal complexity and a higher cap.
Option C (Tranche) helps reduce risk by tying capital to performance but can delay speed and strain founder–investor alignment.
✅ Conclusion:
Option A (SAFE) is usually the cleanest and most scalable route at this stage.
Option C (Tranche) can work well if the team is early and milestones are clearly achievable without slowing momentum.
💭 Final Thought
There’s rarely one “right” answer in VC just the best fit for your stage, goals, and team dynamic. Great investors know how to pick the right structure and the right founder to build with. See you next week!