Stacey Wong

founders that have only ever worked within a large company tend to be empty vessels. the most valuable skill at a big company is identifying who has (or could soon have) power and then aligning with and advocating for their ideas as if they were your own. take a spin through the recent YC class and you see a pattern of big company mids all founding the same AI for xyz... its not really their idea, it just sounds good. the board meetings will be especially painful. founders acting like they work for the investors, seeking approval, lost in the woods. there are exceptions. but they tend to be founded before zirp. when founding a company was hard and low prestige and there wasn't capital at every turn. an empty vessel doesn't jump into the abyss without first raising a $5m round from the 9 figure 'seed firms'. 

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Your early-stage startup ARR isn't a scorecard. It's a learning tool. Founders: bring the story behind the numbers to your board. Not just the numbers. What matters more: - Customer interview takeaways - Why people renew (or don't) - How fast you iterate on feedback - Progress toward product-market fit The real question isn't "did you hit $50K ARR?" It's "what did you learn while getting there?" The best investors/boards care more about the latter.

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Founders with capital that refuse to hire or add resources to alleviate constraints aren't preserving runway -- they're sabotaging growth velocity. I'm seeing this pattern more frequently: 20+ moths of runway, strong customer demand, a product that's delivering ROI but a founding team clearly spread too thin resulting in self-inflicting issues and paper cuts. I think founders feel that by doing everything you're evoking resiliency and capital discipline. Sometimes that's lauded. However, I think it's founders optimizing for control and comfort rather than scale and delegation. From the investor seat, here's how I'm trying to understand this behavior: (1) Avoiding 'role evolution.' - It's hard to graduate from scrappy founder that has to do everything to scrappy founder with the ability to delegate and deploy resources. Hiring means transitioning from building - - > manager - - > leader (2) Control-minded orientation - We naturally feel more accomplished when we can measure our own output (Ex: sales calls made, lines of code written, support tickets resolved, etc...). When you take time hiring and then ultimately unload these tasks, you have to reinterpret your own productivity and be okay with anchoring towards somebody else's. In reality, runway is not the lens to view your business. If capital is sitting idle on your balance sheet with clear use cases for deployment, all you're doing is suppressing momentum and growth. I care less if you were ultimately wrong where you deployed capital rather than running your business to optimize for more runway. Investors implicitly trust your judgment so just have a more growth-oriented mindset 🫡 🚀 .

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6 Comments

Stripe has an annual tradition of releasing a letter to the ecosystem, detailing our progress over the past year (see the letter in the comments). High-Level Highlights: - Businesses on Stripe processed $1.9 trillion in total volume, marking a 34% increase from 2024, which is roughly 1.6% of global GDP. - Stripe now powers over 5 million businesses directly or through platforms, including all top AI companies, 90% of the Dow Jones Industrial Average, and 80% of the Nasdaq 100. - Remarkably, 25% of all Delaware corporations are now created with Stripe Atlas. Agentic Commerce: We remain excited about the future of agentic commerce. To clarify our vision, we've outlined the "5 levels of agentic commerce." - We are building the foundations in this space: - Agentic Commerce Protocol (ACP): Co-developed with OpenAI, this open technical language enables AI platforms and businesses to transact across different providers. - Shared Payment Tokens (SPTs): A new primitive that allows agents to initiate payments securely without exposing a user's sensitive credentials. - Agentic Commerce Suite (ACS): A single integration for brands like Etsy, Anthropologie, Coach, Urban Outfitters, and Kate Spade OKC to sell across multiple AI interfaces. We are energized by our users' growth over the past year and the innovations we have planned to support their continued success.

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From early hire to CBO, Art L. shares how Brex scaled from a corporate card for startups to a global spend platform built for enterprises, with lessons on building trust, navigating M&A, and leading through change. Catch it all on the latest Sourcery drop 🎙️⬇️

14

1 Comment

The single most valuable thing I learned at YC has nothing to do with fundraising, product-market fit, or growth hacking. It's a skill that 90% of founders are terrible at. When you walk into a YC partner meeting, they ask one thing: what does your company do? And then they rip your answer apart. "Simpler." "I still don't get it." "Pretend I'm your mom. Try again." I remember pitching my YC startup with some convoluted explanation about workflow automation and AI-powered insights. I thought it sounded smart. A YC partner looked at me and said, "I have no idea what you just said." Their entire program is obsessed with one principle: if you can't explain what you do in one sentence, you don't understand it well enough yourself. That lesson stuck with me. And when I started Mesa with my co-founder Oliver, I applied it from day one. Every product description, every sales call, every investor update — I ask myself: can I make this simpler? The answer is almost always yes. It took us months to compress our value prop into one line any engineer gets in five seconds: GitHub was built for humans writing code. AI agents write most of the code now. Mesa is the platform built for that world. That sentence is worth more than any pitch deck we've ever built. If you can't explain your company to a stranger in under 10 seconds, that's not a marketing problem. That's a clarity-of-thinking problem. Fix the thinking. The words follow.

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Dayna Grayson is a leading VC who has “sat in every chair” at a young age. She founded Construct Capital with Rachel Holt, an early leader at Uber. Together, they are tackling the digitization of industry. Dayna will discuss macro trends, what it takes to be a founder, and the potential for AI. She is one of the few who have successfully blended a career of operations and investing.  Check out our discussion at: https://lnkd.in/eYBUGjbW #leadershipdevelopment

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"Out of the last 3 years, I've been fundraising for 2.5 of them." A fellow emerging VC manager said this to me last night. Not as a complaint. As a statement of fact. The landscape is genuinely complex right now. Here's what every emerging manager is navigating: You're not just benchmarked against Sequoia and a16z. You're benchmarked against ex-partners FROM those funds — spinning out with instant credibility, warm LP relationships, and a brand that opens doors before they say a word. And then there's the macro: 🥇 Gold at all-time highs. Liquid. Simple. No J-curve. No 10-year lock-up. 📉 LPs who deployed 5 years ago are still waiting on distributions. They're disciplined about new commitments until they see real liquidity. 🔒 Venture is inherently illiquid — and in today's environment, that's a harder conversation than it's ever been. The managers who win in this environment aren't the ones who ignore these realities. They're the ones who understand them deeply and build their approach around them. 1. Invest in relationships long before you need them. Trust built under no pressure is the most durable kind. 2. Let traction do the talking. SPVs, angel deals, co-investments — proof of judgment in action is worth more than any deck. Show the work. 3. Speak their language. A family office and a FoF operate in completely different worlds. The managers who take time to understand each LP's mandate are the ones who earn real consideration. To those who've been through it — I'd love to hear from you. What's one thing that actually shifted your fundraise? Drop it below. There's a whole community of emerging managers who will benefit from your experience. 👇 #venturecapital #fundraising

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Publishing Part 2 of my deep dive into the $42 billion #chargeback problem that's eating into merchant margins and triggering payment processor shutdowns. This one gets technical. I break down the actual dispute lifecycle, the new VAMP rules from Visa that have blindsided merchants, and what startups are building to fight back. Some highlights: → Fraud chargebacks resolved via RDR now count against your ratio → Merchants exceeding 0.9% dispute rates risk termination by acquirers → Post-VAMP, some vendors saw 300%+ spikes in inbound → The space is shifting from "chargeback ops" → payment intelligence platforms Also shared my take on where this market is heading — and what it’ll take to build enduring platforms in the space. Link in comments

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I've met with hundreds of founders over the last few years. The ones who win share one trait. They are convicted, but flexible. The pace of product iteration right now has blown me away. How fast things are able to be built now is unlike anything we have seen before. Build, deploy, learn, iterate, repeat. The cycle keeps getting shorter. This changes what I look for in founders: Sense of urgency matters more than ever. So does the ability to adjust by learning from actual data. You have your idea of what the solution is. You get out there and you learn from the data. Then you say, “Okay, I had my idea, but I better adjust what my ideas were.” You have to be willing to go, "Huh. Interesting. I might have been wrong." That is what convicted but flexible means. • You have conviction on the persona that is having the problem. • You have conviction on what the problem is. • But you stay flexible on what the solution looks like because you can test and iterate and build new things so quickly now. This is not about being wishy-washy. It is about being honest with yourself when the data tells you something different than what you expected. The founders who hold their ideas too tightly get passed by. The founders who abandon their conviction too quickly never build anything meaningful. The best founders sit right in the middle. Convicted but flexible.

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2 Comments