Goodfin Wire - Vol. 10

Ten editions. Still here. Still early.

When we sent Vol. 01, we didn't know if anyone would open it. Now you're reading Vol. 10 and this newsletter has become the signal layer for a community that doesn't settle for surface-level takes on private markets.

So before we get into it: thank you. Not the generic kind. The kind where we mean it. You opened every email. You showed up to firesides at odd hours. You voted in polls, replied with feedback, forwarded the Wire to people you thought should be here. That's how a community compounds.

Now, back to work. A new QSBS feature is in the works. Events are stacked. And this edition has a lot to unpack.

Let's go 🚀

→ Jerry Weitzman unpacked the Databricks playbook—turned down a $20M deal to protect the roadmap, scaled $15M to $2B ARR, and shared the operator signals most investors miss entirely
→ Event recordings are now live inside the platform—catch up on past firesides and webinars on-demand, right from the community page
→ Gatherings Edition 4 goes Valentine's Day—dream dinner guests, ultimate escapes, and what makes us human in an automated world
→ QSBS Essentials with CapGains—advanced strategies session on the One Big Beautiful Bill Act, Section 1045 rollovers, and real-world scenarios
→ QSBS is coming to Goodfin—a new opportunity for tax-free gains on startup exits and investments. Request early access now.
→ Boston Innovation Mixer—an intimate evening in Cambridge connecting the Goodfin, Harvard, and MIT communities over tech, AI, and private markets
→ Member Poll: Are we living through an AI bubble—or just the beginning?

We're four editions deep and the energy keeps building. This time, we're stealing Valentine's Day back from the greeting card aisle and pointing it at something better: the conversations that actually stick.

Three prompts. One community. Just you and a room of investors, founders, and operators getting real about: whom you'd want across the table for a once-in-a-lifetime dinner (and the one question you'd ask), where you disappear to when everything gets loud, and which human quality becomes more valuable the more we automate.

45 minutes. Bring your drink of choice.

The tax code just handed founders and early investors a new set of cards. Most haven't looked at them yet.

Jonathan and Carolyn from CapGains, Inc. are walking us through what changed—and what it means for your next exit. We're covering the One Big Beautiful Bill Act expansion, how Section 1045 rollovers are creating fresh opportunities, capital loss strategies under Section 1244, and live Q&A on the edge cases nobody talks about publicly.

If you hold startup equity or investment in early-stage companies—or advise anyone who does—this one's non-negotiable.

We're hosting an intimate mixer in Cambridge designed to connect forward-thinking people working and investing at the edge of innovation.

An evening of thoughtful conversation, new connections, and community across the Goodfin, Harvard, and MIT ecosystems. Whether you're building, investing, or exploring what's next—this is a space to meet great people shaping the future of tech, AI, and private markets.

Open to Goodfin members, Harvard & MIT alumni, students, and faculty. Investors, startup founders, and operators in tech are all welcome. Light food and drinks provided. Registration is subject to host approval.

Jerry Weitzman didn't just watch Databricks scale. He built the go-to-market engine that took it from $0 to $2B in ARR. Now, as a venture partner at Cascade Venture Partners, he backs Anthropic, OpenAI, Ramp, CoreWeave, and Vercel.

The standout moment: Jerry shared how Databricks' CEO turned down a $20M deal from one of the world's largest banks—a deal that would have doubled the company overnight—because building for on-prem meant building for the past. That discipline defined the company's DNA and is still intact at $5.4B ARR with virtually zero executive turnover.

On building conviction, Jerry doesn't invest from a data room. He embeds as a GTM advisor for months—sometimes years—before writing a check. By the time an allocation opens, he already knows the politics, the BS, and the real story behind the numbers.

On the SaaSpocalypse: legacy SaaS companies built on per-seat pricing will struggle. But the idea that agents will replace Salesforce or Workday overnight? Far-fetched. Enterprise software is more than lines of code—it's governance, security, and decades of embedded workflows.

His sharpest take for private market investors: stop comparing every company to Cursor. Those are one-of-one outcomes. The real signal is sustainable growth—low customer concentration, repeatable deals, and a credible second act beyond the first product.

Imagine turning your startup equity or investment into a tax-free windfall. Qualified Small Business Stock makes that possible—letting qualified investors exclude up to 100% of capital gains, potentially saving millions.

We're building something around this. And if you want in early, now's the time to raise your hand.

Be the first to know how to access pre-vetted QSBS-eligible opportunities and maximize every dollar of your early-stage returns.

Missed a session? Select firesides and webinars are now available on demand inside the platform. Jerry's operator playbook, Eric Satz's Self-Directed IRA breakdown, past member webinars—all in one place, ready when you are.

No more hunting through email threads or asking for replay links. Just log in, hit play, and catch what you missed.

Goodfin is growing the engineering team. Two roles, both in SF, both high-impact:
→ Staff AI Engineer
→ AI Engineer

Know someone who'd be a fit? Referrals that lead to a hire get $20K—as a Goodfin investment or cash. Your call.

The signal that matters surfaced for you. Here's what our AI pulled from the noise this week:

→ Apptronik raises $520M at $5B valuation for its Apollo humanoid robot. Google, Mercedes-Benz, and John Deere are backing the bet. Total Series A now tops $935M. The humanoid race against Tesla's Optimus is heating up. Read more

→ Figma partners with Anthropic on "Code to Canvas." The new feature converts AI-generated code from Claude Code into fully editable Figma designs. A bet that agentic coding won't kill design—it'll make it more essential. Read more

→ Render raises $100M at $1.5B valuation. The cloud platform now has 4.5M+ developers and 100%+ revenue growth. OpenAI's Codex lets users deploy directly to Render. The AI-native cloud layer is forming fast. Read more

→ Databricks and Replit team up on enterprise app development. Developers can now vibe-code data-aware apps in Replit using natural language and deploy directly to Databricks—with full governance and security baked in. Read more

We got more signal waiting for you inside Goodfin.
Sign in to the platform and never miss a beat.

Vote and you're automatically entered to win exclusive Goodfin merch. We'll randomly select voters and send you something special.

Until next time,

Sharath Kuruganty
Founding Community Lead
Goodfin

P.S. – Have feedback on Goodfin Wire? Hit reply. I read everything.

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