We review 400 to 500 deals a month at Redbud. There's a ton of inbound and even more outbound. And at that volume, data gets lost.

Links expire. Decks disappear. Context lives in inboxes. Calendar invites show up with no materials attached. A fund forwards you 10 deals in one email. A founder sends a Canva link, a pitch.com link, and a Google Drive folder — none of which flows cleanly into anything.

And then the data just rots.

About 75% of the deck links we saved over time eventually expired. We weren't going to convert and reupload every one. Nobody is. So we kept losing the deal data.

Most venture tools solve the wrong problem. Affinity is great for relationship tracking. Attio works as a CRM. But neither of them solves ingestion — and ingestion is the actual bottleneck. The part nobody talks about.

So we built Roulette.

Roulette ingests deals, updates, and materials automatically and turns them into a living, searchable intelligence layer for your fund. It's built around five things: ingestion, enrichment, retention, sharing, and synthesis.

You plug in your email. The system processes everything — decks, PDFs, links, data rooms, calendar invites, meeting minutes, forwarded deal bundles. AI reads each piece and builds a live data room per company in the background. If all you have is a calendar invite with a founder's name, it still gets added to your pipeline.

When a founder sends follow-ups three weeks later — updated metrics, a new deck, a data room — it all flows into the same company record. Nothing gets lost. Context compounds instead of leaking. And when you're ready to act on a deal, you can generate a one-pager, a deal memo, or a founder FAQ right inside the platform — without ever switching tools.

AI builds data rooms in the background — automatically, across every source

Pull in what you don't have — automatically

Your deal data, all in one place — yours to keep

AI-matched co-investors. Instant deal links. Full tracking.

Generate real deal outputs without leaving the platform

Connect everything. Own everything.

My team saves at least ten hours a week on data entry. But the real gain isn't efficiency — it's recall. We resurface companies we would have completely lost track of. We spot patterns across hundreds of deals because the data is actually there, clean and structured, instead of scattered across inboxes and dead links.

Deal sharing went from a 30-minute chore to a single click. Select a hundred companies, generate trackable links instantly, copy and paste. The system even suggests which investors in our network should see which deals — based on their actual investment profile, not a gut check.

The synthesis piece changed how we work deals. Instead of copying and downloading data out of Roulette and into Google Docs or LLM of choice to write a memo, we just do it inside the platform. One-pagers, deal memos, founder FAQs — generated from the data room we already built. You can also just chat with the AI against any company's data room, which is the fastest way I've found to pressure-test a thesis before a partner meeting.

The LP side is where it really clicked for me. Our pipeline is clean enough now that I'm genuinely excited to share it. We built an LP dashboard where investors can log in, see what we're evaluating, spot trends, and request intros to founders. A lot of our LPs are high-net-worth individuals — investing isn't their full-time job. When we bring organized, searchable deal flow to them with real context, that's a meaningful value-add beyond returns.

Portfolio monitoring got simpler too. Every time a portfolio company sends an update, it goes straight into Roulette. AI pulls out the KPIs I care about. When it's time to update LPs each quarter, everything's already in one place. What used to take hours takes minutes.

Roulette started as an internal tool. We built it because nothing else did what we needed. The CRMs tracked relationships. The deal platforms tracked stages. Nobody was ingesting the actual materials and making them useful.

That's the gap. And it's costing funds deals they don't even know they're losing.

The founder you met eight months ago whose deck expired. The deal buried in a forwarded email thread. The LP who would've backed a company if they'd known about it. It's not that the opportunity wasn't there; it's that the context disappeared before you could act on it.

Roulette fixes that. Every deal, every deck, every email, every meeting ingested, organized, and searchable. Your data rooms build themselves. Your memos write themselves. Your LPs stay in the loop without you doing the work manually. And your co-investors get the right deals in front of them at the right time.

We built this for Redbud first. Now we're opening it up.

If you're running a fund and you're tired of losing context — sign up to start saving precious time: useroulette.com

Originally posted on Roulette