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📍 SF Bay Area | 💰 Check Size: $500K - $2M | 🎯 Stage: Pre-Seed to Seed | 🏢 Focus: Developer Tools, Infrastructure & AI
Heavybit is a seed-stage fund focused exclusively on developer tools, infrastructure, and AI companies. With 85+ portfolio companies, they are known for their hands-on approach. They run structured programs with founders including messaging sprints, weekly check-ins, and tactical go-to-market support. Their model is simple: invest early, work intensely with founders for 12-18 months, and help them build the foundation to raise their next round successfully.
Jesse Robbins from Heavybit breaks down what early-stage investors are really looking for when evaluating founders and why most of the advice you've heard is probably wrong. He breaks down his specific, tactical insight from someone who's spent decades operating and investing in infrastructure companies.
✓ Why market size is the ultimate gate, even when everything else looks perfect
✓ The co-founder dynamic that predicts success or failure
✓ Heavybit's complete investment process from first meeting to term sheet
✓ Jesse's biggest pet peeves that kill fundraising conversations
✓ What happens after investment: the structured 12-18 month program
"Potential is the ultimate arbiter of whether or not Heavybit will make an investment." — Jesse Robbins
You can have the best team, the most compelling product, and strong early traction but if the market isn't big enough, Heavybit can't invest. Jesse is brutally clear about this: it's not a venture-scale business if the addressable market won't support a meaningful exit.
The trick is that founders often misjudge market size by focusing only on their entry point. Jesse uses LaunchDarkly as the perfect example: feature flagging looked like a small market for software development tools. But Edith Harbaugh (LaunchDarkly's founder) reframed it as business configuration management, a tool that lets companies manage product changes in real-time across their entire organization. That shift took the market from $10B to potentially unlimited.
The question Heavybit asks: "Is this something that has global scale potential? Can it be bigger?"
"When founder relationships fall apart, it is the most value destroying, destructive thing that can happen to you professionally." — Jesse Robbins
Jesse watches co-founder interactions obsessively during meetings. He's looking for "turning towards responses". Do they support each other, even in conflict? Do they yes-and each other's ideas? Are they having fun together, or is there tension beneath the surface?
The Founder role isn't easy and the people you do that with need to be people you genuinely want to work with through the hardest moments. Red flags show up fast: founders cutting each other off, defensiveness, lack of mutual respect.
When Jesse sees a team that clearly likes each other and will support each other through adversity, that's a strong signal. When he doesn't, it's often a deal-breaker, no matter how good the idea is.
"They would have personal grit, meaning that they are able to just grind in absence of positive feedback or stimulus for a really long time because they're driven out of a sense of purpose that comes from the inside." — Jesse Robbins
If Jesse could design the ideal founder in a lab, he'd dial up two traits: personal grit and a strong sense of self. Grit means being able to push forward without external validation for extended periods. It means recognizing that every day you'll be running the largest company you've ever run and no one is going to say thank you.
But you don't need to be a Type-A extrovert to succeed as a founder. Some of the most effective CEOs are introverted, thoughtful, and deliberate in how they operate. What matters isn't your personality type—it's whether you have resolve, personal determination, and an internal drive that doesn't depend on constant external validation.
"Do not send me a doc share thing that I cannot download an artifact from. Send me a thing because I need to download something and share it in advance." — Jesse Robbins
Jesse has specific pet peeves that signal founder judgment:
Don't spam LinkedIn connection requests. Most VCs don't respond to cold LinkedIn pitches from founders. It signals you're taking shortcuts instead of doing the work to get a proper introduction. Use the channels that exist for a reason: attend their events, fill out the contact form on their website, or get a warm intro through your network.
Don't send pitch decks in view-only formats. Investors need to download your deck, mark it up with notes, and share it internally with partners to build a case for you. If you send a DocSend link they can't download, you're adding friction to their ability to champion your company.
Don't lead with your elevator pitch. When you meet an investor at an event, introduce yourself naturally, mention how you know each other or what brought you there, and be conversational. Don't launch into a rehearsed pitch in the first 30 seconds
Don't confuse SAFEs with term sheets. If you tell an investor you're expecting three term sheets this week and those turn out to be YC handshake deals for SAFEs, you've lost credibility immediately. A term sheet is a priced round with specific valuation dynamics. A SAFE is bridge capital. The distinction matters.
"We meet every two weeks minimum for an hour for partner meeting time. That is one-on-one time where we're working at the highest level on helping you succeed." — Jesse Robbins
Heavybit's post-investment model is genuinely different. Within a week or two of the wire clearing, they kick off a structured onboarding process. You meet the entire team, get their personal contact info, and start working on a customized roadmap.
They meet with founders every two weeks minimum. That's 10-20x more frequently than typical VCs. The first 12-18 months involve working through structured programs: messaging sprints, launch planning, pricing strategy, executive leadership development. They're helping you navigate one-way-door decisions that will define your trajectory.
Over 150 hours together in that first year isn't unusual. The goal is to get you into a state where you're ready to raise your next round easily. Founders sometimes focus only on the outcome without acknowledging all the work that went into positioning, messaging, and building traction that made that outcome possible.
Jesse is clear: they take board seats frequently, they're direct (not soft) in their feedback, and they're there for the long haul. You're not just getting capital. You're getting a partner who will help you navigate every hard decision for the next decade.
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