From Syndicates to Scale: My Journey in Venture and Why I’m Still Betting on Outliers
My Journey and Insights
When I sat down with Adeo Ressi at Decile Group, I didn’t expect the conversation to turn into a nearly hour-long deep dive into everything I’ve learned (and unlearned) across 200+ startup investments. But that’s what made it special — we peeled back the curtain on what it really takes to build a top-decile venture firm in today’s environment. This is a reflection of that conversation, from my perspective.
From Big Tech to First Checks
Before venture capital, I spent a decade in finance, followed by years building AI-powered martech, adtech, and salestech startups. I led the AI category at AWS and launched the SageMaker Marketplace, then ran the Azure Marketplace at Microsoft. I scaled startups at Microsoft. But somewhere along the way, I realized I enjoyed working directly with founders more than playing corporate politics.
So I started investing — first as an angel, then as a syndicate lead on AngelList. That evolved into Team Ignite.
I didn't launch with a massive fund. My first raise was a rolling fund for YC startups. Then I launched a proper seed fund — and with each fund, I’ve learned just how hard (and rewarding) this job is.
The First $10M of Mistakes
There’s a saying: “It takes $10 million to become a VC.” That was true for me. My early investing strategy was flawed. I wrote $25K checks too early, with little structure. I didn’t budget for optionality or reserves. But I was willing to make mistakes and learn quickly.
Now, I tell new investors: if you’re serious, budget to make 100 investments over 3–5 years. That’s not because every deal will hit. It’s because venture is a power law game — and statistically, to give yourself a 95% chance of backing a unicorn, you need that volume.
Team Ignite: Our Strategy & Belief
At Team Ignite, we invest in pre-seed and seed-stage startups globally — B2B SaaS, AI, fintech, marketplaces. We make ~150 investments per fund. It’s high-volume, high-discipline, and high-support.
Why that strategy? Because I assume I’m average.
If I’m average at picking, then I have to work harder, invest more broadly, and add more value. If it turns out I’m great, returns will reflect that. But I don’t start from ego. I start from probability.
And so far, it's working. Fund I and Fund II are both top-decile according to Carta benchmarks.
AI Is Changing Venture (and Everything Else)
I’ve been building AI systems since 2013. Today, we use AI in every part of our firm — from sourcing and screening to writing deal memos. The latest OpenAI models are effectively our full-time PhD analysts. I’ve built an internal system that reads decks, transcripts, and data rooms, scores them on our 20-factor rubric, and flags the best 10% for human review.
But AI doesn’t replace my intuition.
The best startups are often non-consensus — ideas that look weird or dumb at first. And AI, by design, reflects the consensus. That’s why the final decision still comes down to gut, to judgment, to reading the founder’s ambition, clarity, and chip on their shoulder.
That’s not automatable. Not yet.
What I’d Do Differently (And What I Still Got Wrong)
Raising a fund is hard — even with a great track record. I’ve made nearly 50 investments before YC. I’ve backed companies before Insight, Benchmark, and First Round. And yet, Fund III has been a slog. Why? Because we’re generalists. That makes it harder to resonate with LPs who want focus.
If I were starting today, I might launch a vertical fund (e.g. AI-only) — not because it performs better (I still believe generalist funds do), but because it’s easier to raise. Platforms like AngelList and Carta don’t help much either — they cross-market your LPs. I’d partner with a firm like Decile from the start.
And I’d always reserve capital. In Fund II, I didn’t. SPVs are soft right now. If you can’t fill them, you miss your pro-rata. Lesson learned.
Final Thoughts: The Only Way In Is to Start
VC is one of the few careers no one gives you permission to enter. You just have to start. Start writing small checks. Start building your network. Start helping founders. No one's going to open the door unless you create your own path.
I didn’t come from a famous firm. I’m not a celebrity operator. But I built Team Ignite from nothing into one of the most active seed-stage investors globally. That came from discipline, systems, and relentless hustle.
If you're trying to get in, don’t wait for approval. Just start.
And if you're building something weird, ambitious, and possibly world-changing — come find us.
Want to pitch us or read our full framework? Visit teamignite.ventures or subscribe to Ignite Insights.