How to get investors interested months before you raise - with the exact emails to send ?

Guide to turn AI into Second Brain & Does Fundraising Size Impact Unicorn Odds?

👋 Hey, Sahil here — Welcome back to Venture Curator, where we explore how top investors think, how real founders build, and the strategies shaping tomorrow’s companies.

• How to Get Investors Interested Months Before You Raise - Plus the Exact Emails to Send.

• How Fundraising Size Impacts Your Startup’s Unicorn Odds.

• How to Turn AI into a Second Brain?

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📜 DEEP DIVE

How to Get Investors Interested Months Before You Raise - Plus the Exact Emails to Send.

Imagine you plan to raise a funding round in six months. The rookie move is to wait until then to approach investors. The savvy move is to start now – building relationships and keeping potential investors in the loop well before you ask for a check.

But how? It’s not just about showing up at events or spraying cold emails. There’s a much smarter, proven approach.

It’s called the Pre-Raise Update Strategy.

The Pre-Raise Update Strategy is simple: send regular, concise updates about your startup’s progress to potential investors in the months leading up to a fundraise.

Instead of only contacting investors when you’re raising (or worse, when you’re low on cash), you court them in advance by sharing your journey over time.

Why bother? Because investors often “invest in lines, not dots”, – they want to see a startup’s progress as a trajectory rather than a one-time snapshot.

Startup Trajectories (By Venturz)

By receiving periodic updates (“the line”), an investor can build conviction that you execute well and hit milestones, making them far more likely to say yes when you finally pitch.

In fact, startups that keep investors updated regularly are 3× more likely to raise follow-on funding - According to NFX survey

Image Source: NFX (Importance of updates)

Consistent updates build familiarity and trust: you stay on an investor’s radar (in a good way) and demonstrate momentum and discipline. Remember, investors fund momentum, not just potential. If you show steady progress and the rare discipline of actually sending updates, you’ve immediately set yourself apart (the majority of founders promise updates and never deliver, so those who do are in the top 5% for investor communication

Courting investors early with updates de-risks your raise.

They’re not scrambling to understand your business under pressure; they’ve watched it unfold. Or as one seasoned investor described backing a founder he followed for two years: “I wasn’t taking a risk – I was placing a bet I’d watched them earn over time.”

So, how to start and send the updates?

1. Build a focused target list

Don’t just create a giant spreadsheet of every VC email you can find. A shotgun approach wastes everyone’s time. Instead, curate a list of investors who are actually a fit:

• Look at who has backed startups similar to yours, especially at your stage (pre-seed, seed, etc.). Tools like Crunchbase, venture databases, and newsletters are useful here.

• Focus on alignment: sector, stage, check size, track record. If you’re a fintech seed-stage startup, a biotech Series B fund is irrelevant — cut them out.

• Check activity: Is the fund actually writing checks? If they haven’t invested in 18+ months, they may be dormant.

• The goal is not “the biggest list.” It’s a qualified list — the people most likely to say yes.

2. Segment and qualify your leads

Once you have your list, break it down into useful tiers:

• Tier 1 (“reach” investors): The dream firms or angels you’d love to bring on board, usually well-known names in your sector.

• Tier 2 (“priority” investors): Still good fits, maybe smaller checks or slightly less perfect alignment, but worth engaging.

Also, segment by connection type: who can you reach via a warm intro versus who will be cold outreach? Warm leads always go first.

Pro tip: Use your network to expand the list. Ask advisors, mentors, or founder friends to suggest relevant VCs.

“I know a healthtech founder did this and landed 50 warm introductions in a single weekend.”

And treat this like sales. Use a lightweight “investor CRM” — even a spreadsheet — to track:

• Who’s in your funnel

• Where the relationship stands

• Notes on conversations

That way, no warm lead slips through the cracks.

3. Find the right people at each firm

Don’t just write down firm names; identify individuals. At the seed stage, associates or junior VCs are often the best entry points.

• Associates are literally incentivised to scout companies early and build relationships. They may not sign the check, but they can champion you internally to partners.

• Don’t overlook angels and micro-VCs. At pre-seed and seed, a syndicate of well-connected angels can be just as valuable as a big-name fund.

• Segment your list further by type: angels, seed funds, strategic investors, corporates, and tailor your approach to each.

By the end of this research and filtering, you might have, say, 50–100 solid prospects who could invest in your round. Now it’s time to warm them up – long before you officially pitch.

Warm-up campaign: reach out and get on their radar

Once you’ve built your target list, the next step is simple: start the conversation.

The goal here isn’t to ask for money. It’s to get on their radar and earn permission to keep them updated.

Start with warm intros

Warm introductions beat cold emails every time. Investors get buried in inbound, but when a trusted contact forwards your note with “Hey, you should meet this founder,” they’ll pay attention.

• Warm referrals typically see a 20–30% response rate, compared to <5% for pure cold outreach.

• Look for mutual connections through fellow founders (especially those in a VC’s portfolio), accelerator peers, or advisors.

• Tools like LinkedIn are useful for spotting 2nd-degree connections. When asking for an intro, make it easy by writing a short forwardable blurb that your contact can simply copy-paste.

Don’t fear cold outreach

That said, cold emails aren’t worthless — especially with smaller funds, solo angels, or “super-connectors” in your industry. Many investors do respond if you keep it short, relevant, and personal.

The key is not to open with “we’re raising.” Instead, try a softer approach: ask for permission to send updates as you build. It’s a low-commitment question that’s easy to say yes to, and it starts the relationship without pressure.

One SVB advisor calls this the “permission email.” In just a few lines, you:

• Introduce yourself and your company

• Show why you might be relevant to their thesis

• Ask if you can include them in your progress updates

Most investors will say yes, especially if you’ve done the homework to ensure they’re a good fit.

Example – The Investor Update Invite Email: Below is a template you can adapt when reaching out to a VC (perhaps an associate) you haven’t met yet.

The goal is to introduce yourself, highlight why they might be interested, and get their OK to send updates:

Subject: [Your Company Name] – Updates for [Investor Name/Fund]

Hi [Investor Name],

I’m [Your Name], the founder of [Company], a [brief one-liner describing your startup]. I’m reaching out with a quick ask: we send a short monthly update on our progress and milestones, and I’d love to include you (BCC’d) on that email.

We haven’t officially kicked off fundraising yet, but based on [why they’re a fit – e.g. your focus on healthtech], I thought our journey might be relevant to you. In the past few months we’ve [mention one recent achievement, e.g. launched our beta with 100 users], and over the next quarter we’re aiming to [upcoming goal, e.g. expand to 3 pilot customers].

If you’d prefer not to receive these updates, no worries at all – just let me know. Otherwise, I’ll be excited to keep you in the loop. Thank you!

Best,
[Your Name]
[Your Title], [Company]
[LinkedIn or Website URL]

A few important notes about this approach: keep it short and factual. You’re not attaching a deck, you’re not asking for a meeting. You’re simply asking, “Can I send you updates?” That’s an easy yes for most investors; it costs them nothing until they decide they’re interested.

You’re also dropping a subtle signal that fundraising is on the horizon (“haven’t kicked off fundraising yet”), so they understand the context. Mentioning a recent win plus a near-term goal gives them just enough to see momentum without overselling. And when you start sending updates, always BCC your list, don’t put investor emails on display, and keep the note feeling like a direct message from you.

By doing this, you accomplish two things:

1. You get on an investor’s radar in a positive, non-intrusive way.

2. You set yourself up to send consistent, more substantive updates over time.

Most founders are surprised at how high the hit rate is. Early-stage VCs and angels almost always reply with a quick “Sure, go ahead.” Why? Because it’s literally their job to track emerging companies. Or as one Techstars mentor likes to remind founders: “Build your network before you need it.” That’s exactly what you’re doing here.

Once someone agrees, they’ve moved from a cold lead to a warm one. Now the job shifts: send updates that are worth reading and make them want to keep following along.

Crafting your pre-raise investor updates email

So you’ve got a list of investors who’ve agreed to receive updates. Now comes the big question: what do you actually send them?

The guiding principles are simple: keep it concise, keep it high-signal, and keep it consistent. You’re not writing a press release or a novel. This is a short, scannable email that lets investors see your momentum and your thinking — in under two minutes.

Frequency

Monthly is the sweet spot.

• Frequent enough to show momentum, not so frequent that it’s annoying.

• If your business moves slowly (deep R&D, hardware, etc.), bi-monthly or quarterly is fine. But don’t stretch beyond that.

• The real key is consistency. If you commit, stick to it. Sporadic updates erode trust, while regular updates build it.

Think of it like brushing your teeth: set a recurring reminder and get it done on schedule.

Length and format

Keep it short, simple, and skimmable. A few short paragraphs or bullet points.

• Use headers like Highlights, Challenges, Asks.

• Bullet lists > big blocks of text.

• Investors don’t want a board report; they want a quick sense of how things are moving.

Pro tip: Some founders even mirror the structure of post-raise investor updates, just leaving out sensitive details.

What to include

Most strong pre-raise updates have some version of these sections:

• Quick overview A one-liner upfront: “Strong month: grew 20% and launched [X].” Think of it as your subject line in sentence form. Investors skim — don’t bury the lede.

• Key metrics Share 1–3 metrics that matter: revenue, GMV, users, engagement, churn, burn/runway. Add the change vs. last month/quarter to show momentum. Example:

  • MRR $15K (+10% MoM)

  • Users: 8,000 → 9,500

• Highlights/wins: A few bullet points of recent wins:

  • +$50K in new bookings from 3 pilots

  • Hired a senior engineer from Spotify

  • App featured in Product Hunt’s newsletter

• Challenges/lows Be real. Acknowledge what’s hard — churn up, launch delayed, hiring bottleneck. This builds credibility and often invites help.

• Next steps/priorities: What’s coming next? Keep it short, e.g.:

  • Launch beta with Partner X

  • Hire 2 sales reps

  • Target $20K MRR by July

• Ask them how they can help. Be specific. Examples:

  • Referrals for frontend engineers

  • Intros to HR leaders for beta testing

  • Advice on B2B SaaS pricing

  Specific asks turn passive readers into active allies.

• Closing note End with a quick thanks and sign-off. Something simple like:
  “Thanks for following along — appreciate the support. Until next time, [Your Name].”

Subject lines & delivery

• Stick to a consistent format: [Company] Update – [Month Year]. Easy to search later.

• Optional: add a teaser (“March Update – 3× Revenue Growth”) if you want to drive opens.

• Always BCC your list, don’t expose emails, and keep the tone personal.

Many top founders swear by this formula of concise, regular updates. It keeps your company at the top of investors’ minds and shows that you operate methodically.

As one VC survey found, the majority of great founders communicate at least monthly. And if you’re wondering whether investors actually read these emails – they do. In fact, some investors will look forward to your updates if you consistently share interesting insights and progress; they become emotionally invested in your journey. You’re effectively turning prospective investors into an audience rooting for you.

Subject: [ABCD] – September 2025 Update

Hi everyone,

It’s been a busy month at ABCD! Our focus this past month was on scaling our new mobile app and boy, did things move.

Key Results: We grew to 15,000 users (25% MoM increase) and landed 2 pilot customers for our B2B platform. Revenue hit $8,200 MRR (+18% MoM).

Highlights:

• Product: Launched the Android version of our app, which now accounts for 30% of new signups.

• Sales: Signed a 6-month pilot with MegaCorp Inc. (our biggest client to date!).

• Team: Brought on a UX designer (ex-Google) to polish our onboarding flow.

Challenges:

• App churn ticked up slightly this month – we’re analyzing user feedback to address retention.

• Hiring for Head of Sales is moving slower than expected; looking for more candidate leads.

• Our AWS costs spiked unexpectedly (perhaps a good problem – usage is growing fast!).

Next Up: In October, our goal is to launch the Team collaboration feature (waitlisted by 500 users) and reduce churn back below 5%. We’re also gearing up for our first industry conference demo in late October.

How You Can Help: 1) We’re hiring a Head of Sales – please send any great SaaS sales leader referrals our way. 2) Seeking intros at enterprise HR departments; we want 2 more pilot customers by year-end in that space. If you know any HR execs open to innovative solutions, we’d love an intro. 3) Any recommendations for optimizing AWS costs at our stage? Tips welcome!

Thank you for reading and for all the support. Several of you responded to last month’s update with helpful advice – hugely appreciated! As always, feel free to reach out any time.

Until next time,
[Your Name]
CEO, AcmeCorp
[LinkedIn] | [Email] | [Company Website]

The example structure above is just a guide. Your updates can be shorter or vary in format — the important thing is to include the core ingredients: a friendly hello, quick recap of focus and wins, a couple of key metrics, highlights, challenges, what’s next, and clear asks.

Keep the tone transparent and grounded, not hypey. If something’s off-track, say so and show how you’re fixing it. Investors value honesty more than spin. And remember: some of your audience isn’t yet an investor, so don’t overshare sensitive details like exact cash in bank — top-line numbers and qualitative progress are enough.

There’s also a hidden benefit for you: writing these updates forces reflection. You celebrate wins, confront problems, and sharpen your story month by month. Many founders later realise their updates became the backbone of their pitch deck — proof they said they’d do X, then did it, then built momentum toward Y and Z.

In short, updates aren’t just about keeping investors warm. They make you a sharper, more disciplined founder, too.

From updates to fundraising: smoothly transitioning to “ask mode”

If you’ve been sending pre-raise updates for a few months, the next step is inevitable: raising for real.

The question is, how do you flip those warm relationships into actual funding conversations? The answer is: tactfully and directly.

It shouldn’t be a surprise to your update recipients that you’re planning to raise. In fact, you may have hinted at it already (“before we start looking to raise, I want you to know us,” or “we’re planning to raise in Q1 to fuel growth”). When the moment comes, don’t send a mass blast. Instead, prioritise the investors who’ve been the most engaged with your updates — the ones who reply, click links, or have already taken calls with you. Send them a short, personal note along the lines of:

“As you’ve seen from my updates, we’ve hit A, B, and C over the last six months. Now we’re raising a $X round to scale [business]. Since you’ve been following along, I wanted to reach out early to see if this could be a fit for [Fund].”

Attach your deck if appropriate, suggest a meeting, and make it clear you’re officially in fundraising mode. This way, the “ask” feels natural — it’s just the next step in a conversation you’ve already been having.

You can also mention your raise more broadly in an update (without a direct ask), e.g.:

“P.S. – We’ve begun preparing to raise our seed round in January. If you’d like details or know someone who might be a fit, let me know.”

This creates soft urgency. You’ll often find that even investors who never replied before will resurface now — nobody likes to miss out once momentum is visible.

The beauty of this strategy is that when you enter fundraising mode, you’re not starting from scratch. These investors already know your team, your cadence, and your execution.

When you finally sit down for pitches, you’ll notice the difference: instead of “so, what do you do again?” the conversation jumps to deeper topics.

Some investors may even feel emotionally invested (“I remember when you had 100 users — now you’re at 10k!”). That sense of shared journey often accelerates a yes.

But don’t get complacent. Warm relationships don’t mean automatic checks. Run a proper process: prep your deck and data room, set a timeline, and keep new investors flowing into the funnel. The difference now is you’re pushing on open doors.

Common mistakes to avoid

Even the best strategy can backfire if you trip on common pitfalls. Here are the ones that derail founders most often:

• Waiting too long to start: The #1 mistake is going quiet until you’re desperate for capital. If you show up cold with two months of runway left, expect tough terms (if any). Dig the well before you’re thirsty. One founder raised $1.2M, went silent for 14 months, and when he came back low on cash, almost every investor ignored him. Don’t wait for the “perfect milestone.” Start 3–6 months pre-raise, even if it’s just short updates.

• Inconsistent or sporadic updates: One update followed by silence kills momentum. Investors assume something’s wrong or forget you exist. Pick a cadence (monthly or quarterly) and stick to it. Even a two-paragraph note beats disappearing. Use a template and block an hour a month — this isn’t a 3-day writing project.

• Sending fluff instead of signal: Avoid vague cheerleading (“we’re excited and working hard!”). Investors want numbers, milestones, and context. Share meaningful metrics (“MRR up 20% MoM thanks to a new referral program”) and the story behind them. Honesty about challenges builds credibility; PR spin erodes it.

• Over-optimising and overthinking: Don’t hold updates hostage until you hit some magical milestone. Progress is rarely perfect — share it anyway. Better a simple, timely update than a polished masterpiece that never ships. And don’t over-worry about individual recipients. If someone thinks you’re too early, that’s fine. You’re writing for momentum, not perfection.

Wrapping up: your playbook for “warm” fundraising

Fundraising is hard. But it’s much easier when you’ve been laying bricks for months. The Pre-Raise Update Strategy is about turning cold outreach into warm conversations, and warm conversations into real checks.

To recap:

• Start early: Build your target investor list 3–6 months before raising.

• Ask for permission: Use a simple outreach to get on their radar with updates.

• Send consistent updates: Monthly is ideal. Include metrics, wins, challenges, next steps, and asks. Keep it short, honest, and useful.

• Engage replies: Respond quickly to feedback. That’s where real relationships form.

• Transition smoothly: When it’s time to raise, reach out personally to your most engaged contacts.

• Avoid pitfalls: Don’t ghost, don’t send fluff, don’t over-polish, and don’t break trust.

Done well, you’ll notice the shift: instead of convincing strangers, you’re inviting familiar allies to join your next chapter. For many founders, that difference is everything.

This strategy works — it’s the same rhythm many great founders use with their existing investors, extended to future ones. It costs almost nothing beyond an hour each month, but the payoff in fundraising efficiency is massive. Think of it as planting seeds: you invest in relationships today so that capital grows tomorrow.

Also, recently, we published an Investor Outreach Email Sequence Pack that includes 20+ proven templates used and approved by VCs

• Cold outreach templates that actually get replies

• Warm intro scripts that make people want to introduce you

• Follow-up emails that boost response rates by ~28%

• Post-meeting templates to keep momentum alive

• Real examples of emails that led to actual investments

• BONUS:

  • Fundraising CRM Guide for Founders

  • Fundraising CRM Excel Template

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📃 QUICK DIVES

How Fundraising Size Impacts Your Startup’s Unicorn Odds.

A new study from Stanford Graduate School of Business analysed how total capital raised correlates with a startup’s chance of hitting the $1B valuation mark, and the results are clear: money matters, but only up to a point.

Startups that raise small rounds rarely make it to unicorn status, but those that cross certain fundraising thresholds dramatically increase their odds.

Here’s what the data shows:

• <$20M raised → 0.3% unicorn odds. Almost zero.

• $20–40M → 1.2%. Triple the chance, but still low.

• $40–80M → 2–4%. The early growth lift begins.

• $120–160M → 5–6%. The probability accelerates.

• $160–200M → 8–10%. The sweet spot.

• $200M+ → 9.6%. Returns start to flatten.

Key takeaway: Raising more does increase your unicorn probability, but the relationship plateaus after ~$200M. Beyond that, capital alone doesn’t make you more likely to succeed.

For founders:

• Hitting $100–200M raised signals institutional belief and maturity; this is where scaling velocity, not survival, defines outcomes.

• But fundraising isn’t destiny. Execution, market timing, and compounding growth still drive whether those dollars turn into billions.

In short: Big rounds open the door to unicorn status. But what happens next depends on what you build, not just what you raise.

How to Turn AI into a Second Brain?

Most people use AI like a fancy autocomplete. They type a question, grab the first answer, and move on. But that only scratches the surface.

Hiten Shah shared a powerful thread recently 11 prompt structures that help you think better, uncover sharper insights, and build stronger strategies using AI.

Here’s the full breakdown:

• The Chain Reaction Method

Every answer is a building block. Instead of a single question, try “Summarize this” → “Now critique it” → “Now improve it” → “Now make it actionable.” One-shot prompts give surface-level answers. Chains go deeper.

• The Forced Analogy

AI connects the dots in unexpected ways. Ask “Explain this like a sports coach would”
or “Compare this to how chess players think.” Ideas become clearer when framed through a different lens. The best insights come from collisions.

• The Persona Flip

AI defaults to the dominant perspective. Flip it. Try “Explain this from the viewpoint of a sceptical CFO” or “Write this as if you are a customer who just churned.” Seeing through different eyes forces clarity.

• The Priority Filter

If everything is important, nothing is. Ask “Rank these in order of impact” or
“If I could only do one, which should it be?” AI helps filter out noise. The best decision-makers cut through complexity fast.

• The Gap Finder

You don’t know what you don’t know. Ask “What are three questions I should be asking but haven’t?” or “What’s missing from this strategy?”
Most people focus on what’s there. The real leverage comes from what’s missing.

• The Stress Test

AI defaults to clean, logical reasoning, but real-world ideas break under pressure. Try “Find three ways this could fail” or “Where would this idea collapse under real constraints?” The strongest strategies aren’t just good, they survive reality.

• The Break & Build

Instead of refining an idea, destroy it and rebuild it stronger. Ask “List all the weaknesses in this” then “Now reconstruct it while fixing those flaws.”
Most people iterate by polishing. The best iterate by breaking and rebuilding.

• The Extremes Approach

AI thinks in averages. Force it to think in extremes. Try “Give me the most radical version of this idea” or “Now strip it down to the absolute simplest version.”
You’ll uncover insights that never appear in the middle.

• The Layered Explanation

Great ideas work at multiple levels. Try “Explain this in one sentence” → “Now in one paragraph” → “Now in a full-page breakdown.” If an idea doesn’t scale from short to deep, it isn’t truly clear yet.

• The Style Shifter

A message is only as strong as how it lands. Ask “Rewrite this with more urgency” or “Make this more persuasive to an investor.” Great thinking isn’t just about what you say. It’s about saying it the right way.

• The Negative Space

People focus on what’s there. The best focus is on what’s missing. Ask “What isn’t being said here?” or “What’s implied but not directly addressed?” AI can surface gaps in logic, positioning, or messaging that you wouldn’t otherwise see.

You can check out 10+ prompts here in the Google Sheet.

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