Blog

How often investors should think about dilution: not much at all. We give our take on the more important metrics you should focus on instead.

What should founders do if they have no traction? Eric Bahn (co-founder and GP at Hustle Fund) insists that even early-stage startups with no paying customers have some level of traction to consider. After listening to 100,000 pitches over the course of his career, here are the signs he looks for from stellar founders.

Turner Novak built Banana Capital by backing repeat founders building category-defining platforms. His investments in Linktree, Substack, and Replit reveal a focus on growth efficiency, network effects, and companies that could become infrastructure. For early-stage investors, his approach offers tactical lessons about evaluating deals and building valuable portfolios.Retry

Megan Quinn built her Spark Capital portfolio by backing deeply technical founders solving infrastructure problems. Her investments in Databricks, Snyk, and LaunchDarkly reveal a focus on bottom-up adoption, technical depth, and products that become mission-critical. For early-stage investors in B2B infrastructure, her approach offers tactical frameworks for evaluating technical founders and infrastructure markets.Retry

Julia Hartz, co-founder and former CEO of Eventbrite, applies her operational experience to invest in marketplaces, small business tools, and companies with strong female leadership, focusing on founders who understand unit economics and can actually execute rather than just pitch. Her investment strategy emphasizes sticking to markets where she has expertise, betting on operational excellence over just growth metrics, and providing hands-on value through her experience scaling a company from startup to IPO.

Oprah's portfolio shows a disciplined focus on mission-driven companies where she can add real value beyond capital. Through her family office OW Management, she's built a portfolio that prioritizes long-term relationships over quick flips—turning expertise-driven investing into generational wealth. Discover why her approach works when most angels lose money.

Serena Williams isn't just dominating on the tennis court. She's built one of the most interesting investment portfolios in venture capital, and her approach offers crucial lessons for early-stage investors. Through Serena Ventures, she's deployed over $111 million across 80+ companies, focusing on underrepresented founders not as charity but as smart, contrarian investing.

Dustin Moskovitz co-founded Facebook and Asana, and his investment approach reveals crucial lessons for angels. He focuses on infrastructure over apps, decades over quarters, and technical excellence over growth hacks. His portfolio includes deep tech, B2B software, and companies solving real problems. For early-stage investors, his anti-hype positioning and operational focus offer a proven alternative to chasing trends.RetryS

When I asked seasoned investors the best way to get good at investing, they all say the same thing: start a syndicate. I sat down with Brian Nichols, an investor (and my colleague) who runs two successful angel syndicates that have helped 70 startups raise $25m in funding from around 2,000 investors. Here are some of his learnings around starting and running a syndicate.

When Charles first approached LPs for his fund, he thought he had everything he needed to be successful: extensive VC experience and a good idea. But he couldn't raise any LP money for the longest time. He sat down to re-think the framing of the fund and discovered the missing piece.

Explore key characteristics and strategies that define modern angel investing and how to thrive in the evolving startup landscape.

Unicorns are not just rare creatures; they are pivotal for the VC ecosystem. Discover their significance and what they mean for investors and startups.

Complete guide to pre-seed investing for angel investors: funding amounts, valuation methods, due diligence checklist, success metrics and common pitfalls to avoid.

When should a startup raise debt capital rather than equity? Elizabeth Yin shares the difference between a debt round vs an equity round and how first-time raisers should think about approaching their fundraising.

Sean Parker went from building Napster at 19 to backing Spotify and Facebook. His investment strategy focuses on paradigm shifts over incremental improvements, founders with deep product intuition, and companies with strong network effects. Here's what early-stage investors can learn from studying Sean Parker investments and his approach to backing winners.Retry

A profile of Satya Patel, co-founder of seed fund Homebrew, tracing how stints at DoubleClick, Google (AdSense), and Twitter shaped his thesis to back “bottom-up economy” platforms that empower individuals and small businesses. It highlights Homebrew’s early bets on Chime, Plaid, Gusto, and SaaS-enabled marketplaces, and Patel’s hands-on, product-driven approach to helping founders find PMF, build distribution, and scale teams

Since launching Sandberg Bernthal Venture Partners in 2021, Sheryl Sandberg has quietly built a portfolio that includes one unicorn (Pigment) and multiple billion-dollar companies (Maven Clinic at $1.7B, Guild Education at $4.4B). Her secret isn't chasing hot sectors—it's investing like an operator, not a financier. After 14 years scaling Meta from $150M to $116B in revenue, she applies platform-building insights to spot companies that become infrastructure others depend on. From her concentrated 4-company portfolio to her network-driven deal flow, Sandberg proves that the best VCs aren't just capital allocators—they're operators who recognize execution patterns that pure financiers miss.Retry

Reshma Saujani built Girls Who Code before becoming an active investor focused on the care economy and companies serving underrepresented communities. Her approach proves that mission-driven investing doesn't mean sacrificing returns. This breakdown reveals how backing founders solving overlooked problems can generate both impact and profit.

Reid Hoffman didn’t just spot patterns—he authored them. This piece shows how LinkedIn’s network-effects blueprint became his Greylock thesis, powering early conviction in Facebook, Airbnb, and Aurora, and now a broad AI bet. The lesson for angels: hunt for platforms where every new participant compounds value, blitzscale to lock the moat, and think in decade-long arcs.

Stripe’s Patrick and John Collison have turned infrastructure builders into infrastructure investors—quietly backing foundational tech that other companies rely on, from fusion energy to AI research. Their thesis is developer-first, global, and long-term: fund platforms that unlock new business models and compound over decades—a playbook for angels serious about real economic infrastructure.

A few weeks ago at Angel Squad Summit, investors Eric Bahn (Hustle Fund), Elizabeth Yin (Hustle Fund), and Mac Conwell (Rare Breed) heard two pitches from startup founders. The investors asked a few important questions before sharing whether they would or would not invest in these companies (and why).

Paul Buchheit created Gmail and became one of the most successful angel investors by backing Airbnb, Stripe, and Reddit early. His investment approach focuses on products that feel magical, technical founders who ship fast, and platforms over features. Here's what early-stage investors can learn from studying Paul Buchheit investments and his contrarian approach.Retry

A behind-the-scenes look at Marc Benioff’s Time Ventures reveals a platform-first playbook: back execution-first teams building foundational infrastructure—where network effects, high switching costs, and enterprise-grade delivery create durable moats. From fusion to hydrogen to carbon markets, the portfolio clusters into reinforcing themes, turning Benioff’s enterprise expertise into a compounding ecosystem advantage.

Max Levchin's investment approach reveals a focus on hard technical problems in regulated industries. From PayPal to Affirm, Yelp to Brex, his portfolio shows a consistent pattern: backing infrastructure plays disguised as consumer products. For early-stage investors, Levchin's "Hard, Valuable, Fun" framework offers a blueprint for finding defensible opportunities.Retry

Here's a controversial opinion about evaluating startups from investor Elizabeth Yin.

Logan Green—Lyft’s co-founder—has moved from operating to investing as a venture partner at Autotech Ventures, bringing rare, hands-on expertise in marketplaces, regulation, and fleet ops. His lens favors platforms that solve trust/safety, unlock network effects, and can scale across cities—spanning AV commercialization, EV infrastructure, last-mile logistics, and MaaS. The throughline: operator-grade rigor on unit economics and policy, resulting in mobility startups becoming real infrastructure.

Lachy Groom left Stripe to become one of tech's best angel investors, backing Figma, Notion, Ramp, and Lattice early. His strategy: invest in tools with bottom-up adoption, technical founders solving workflow problems, and companies in markets he deeply understands. Here's what his disciplined approach teaches early-stage investors.

Are media companies an overlooked opportunity? Most VCs don't invest for two main reasons: the revenue model and the exit potential. That said, the opportunity could be right if media company founders mitigate those concerns. Here's how.

Master investment syndicate platforms with our complete guide to collective investing, lead investor evaluation, and transitioning from member to syndicate lead.

What happens when you invest in companies within the same industry? Here are our best practices for investors on allocating checks, managing tricky relationships, and what to do after you invest.

Have you ever tried dating in a small town? the options are limited.

A friend of mine asked me to invest in her seed round. The only problem is that I don't have conviction in the business yet. But how do you say no to a friend? Especially when that friend knows you're an investor? I reached out to an investor friend for some advice and she shared the three buckets this opportunity must fit in before making any deal.

Brian Nichols (head of Angel Squad) and Shiyan Koh (co-founder and GP at Hustle Fund) share their four biggest tips to go from angel investor to venture capitalist.

Most people know Garrett Camp as Uber's co-founder, but his real genius shows up in his investment strategy. Through startup studio Expa, Camp systematically builds companies that become critical infrastructure for other startups. Look at the pattern: Convoy revolutionizes freight logistics, Radar provides location APIs, Fabric creates headless commerce infrastructure. These aren't consumer-facing products - they're picks and shovels other companies can't live without. With $350 million raised and 2 unicorns from 69 investments, Expa's concentrated approach beats typical spray-and-pray VC models. The tactical lesson? Focus on B2B infrastructure over consumer apps. Infrastructure companies have better unit economics and higher switching costs. When evaluating deals, ask: is this a company other companies will depend on?

Hunter Walk's Homebrew VC focuses on companies with "bottom-up adoption, top-down sales" - products users love that monetize through enterprise customers, like Plaid and ClassDojo. His approach emphasizes investing in missionary founders with strong product intuition and clear go-to-market strategies across three themes: new work tools, consumer-to-B2B products, and next-gen infrastructure.

Evan Spiegel's investment approach reveals how the Snapchat founder thinks about platforms, timing, and human behavior. His bets on camera technology, AR infrastructure, and creator tools show a willingness to be early on major trends. For early-stage investors, Spiegel's strategy offers lessons about building concentrated conviction in infrastructure plays.Retry

Hustle Fund just raised its third round of funding. Here's the exact pitch we used to raise $125 million since launching our business.

Dave Morin—early Facebook leader behind Platform and Connect, later founder of Path and Slow Ventures—now runs Offline Ventures, a $100M fund (with Apple as an anchor) backing “humanist technology.” His thesis: platforms and tools that enhance wellbeing and human potential—especially in mental health, health tech, creator infrastructure, and human-centered AI—beat growth-at-all-costs. Portfolio and past bets (Slack, Pinterest, Clubhouse) reflect long-term, design-driven, community-focused products.