Email Hacks for Founders and Entrepreneurs

Last week, a founder messaged me... "I've sent 200 cold emails to VCs. Zero responses. What am I doing wrong?" I felt the pain. Because here's what nobody tells you about cold emailing VCs... Your response rate isn't 1%. It's 0.001%. Even with solid traction. Even with growing MRR. Even with a killer pitch deck. Why? Let me share what I learned after 4+ years of helping founders with fundraising. VCs get 500+ cold emails per week. Your perfectly crafted email? It's competing with 499 others. And most partners don't even check their inbox – their associates do. But here's the real kicker... The founders getting funded aren't playing the cold email lottery. They're using a completely different playbook. Instead of spraying emails everywhere, do this... 1. Find 3 competitors who recently raised 2. Look up their investors on LinkedIn 3. Identify mutual connections 4. Ask for warm intros through those connections Don't pitch. Help first. Share a market insight their portfolio company could use. Point out a hiring opportunity for their team. Send a competitive analysis they'd find valuable. Build the relationship before you need it. When you DO send that email (warm or cold), structure it like this... Line 1: Traction metric that makes them lean in Line 2: Why this matters NOW (market timing) Line 3: Who else is interested (create FOMO) Example: "We hit $50K MRR in 6 months. With AI regulations coming in Q3, we're positioned to capture the compliance market. Currently in discussions with [Notable Angel]." Most VCs won't invest if they've already backed your competitor. So stop pitching to investors who funded your competition. You're just giving them free market intelligence. Instead, find VCs who... -Missed out on your competitors' rounds -Have portfolio companies that could benefit from your solution -Just raised a new fund (they NEED to deploy capital) Remember, Fundraising isn't about sending more emails. It's about sending the RIGHT emails to the RIGHT people at the RIGHT time. What's your biggest fundraising challenge right now? --- Hi, I am Nidhi Kaushal, founder and CEO of Team Flexbox. We offer end-to-end fundraising support to founders at all stages from pre-seed to IPO. If you're struggling with investor outreach, sometimes you just need fresh eyes on your approach. Check the link in my bio or DM me to book a 1:1 call. Let's get you investor-ready!

I've closed deals worth $200k+ in a month, matched 10x talent with multiple companies, and raised money - all by writing better emails. Here's what I've learned after sending 1000s of emails to prospects, VCs, and candidates (that actually get replies)... Prospects receive: - Generic "I can help grow your business" pitches - Templated messages with wrong company names - Vague value propositions without proof - Sales emails that sound like... well, sales emails VCs receive: - 100+ decks weekly with no context - Copy-paste pitches sent to 200+ investors - Asks without understanding their thesis - Cold inbound from unknown founders Candidates receive: - "Great opportunity" with zero details - Salary ranges hidden until final rounds - Job descriptions that could be any company - Recruiters who clearly didn't read their profile How we stand out with a couple of tweaks to the old playbook 90% follow: 1/ For prospects: Share value upfront Instead of the same generic "Hey, I can help you hire better/faster," we send: "Hey, I dound these 10 candidates who match your senior developer role. Here are their complete profiles + contact info. No strings attached." 2/ For VCs: Warm intros only We never cold emailed VCs. Our hierarchy: Already invested investors (ask for intros) > Portfolio founders (natural connectors) > Friends & acquaintances (personal vouching) > Non-invested VCs (last resort, through warm intros). 3/ For candidates: Full transparency Most recruiting emails hide crucial info. We include the exact salary range (for e.g., $120-140k base + equity), complete JD, why they specifically fit (reference their background), and team structure/growth stage. TL;DR, - Research thoroughly (spend at least 10 minutes/email) - Lead with value, not ask first - Be super specific - Attach some proof of work - Make it very easy to say "yes" What is your framework for writing emails that convert?

Most founders follow up too much. Or not enough. Here's the sweet spot (so you can 3x your response rates) First, 85% of follow-ups fail because of: • Generic "just checking in" DMs • Following up daily (desperate energy) • Copy-pasting the same message • Giving up after 1-2 attempts Most investor DMs get deleted or forgotten after 15 seconds. It’s just the way it is... Follow-up solution: The 3-7-14 method: If your first message gets ghosted, wait 3 days. Then launch this sequence. DAY 3: Share Relevant Industry Insights "Saw this analysis of AI startups' unit economics. Reminded me of (relevant application) ... " No response to that? Bide your time until 7 days after the initial message. DAY 7: Offer Specific Value: "Saw your recent post about enterprise sales. We’ve interviewed 5 CIOs this week. Here are 3 surprising findings..." If you hear crickets after this, don’t stress. Give it another week. Then slide in with an update: DAY 14: Update On Progress: "Since our first message, we've (Specific Outcome Unlocked) and signed XYZ client. Still interested in connecting?" You can use a simple tracking table and create specific follow-up templates in a tool like Notion to track this. No need to go overboard. Tips to run this strategy smoothly: • Add calendar reminders for each follow-up • Track response rates by message type • Follow their social media for conversation starters • Give without asking for anything If you don’t hear back after this, give it two weeks, then circle back with another update. Benefits of the 3-7-14 method: • Non-pushy relationship development • Regular investor feedback loop • Top-of-mind positioning • Stronger network over time Persistence without pestering is an art. The difference between funded and ghosted often comes down to follow-up strategy. Make yours count. ____________________________ Hi, I’m Richard Stroupe, a 3x Entrepreneur, and Venture Capital Investor I help early-stage tech founders turn their startups into VC magnets

As a General Partner at Vibranium.VC, I see almost 100 messages a day from hopeful startups. Let me share some patterns I've noticed – and how you can stand out: ❌ First, what NOT to do: - Long-winded Emails: Your novel is your passion, but in my inbox, brevity wins. - Comedy Club Pitches: Humor is great, but clarity and focus are what I'm looking for. - Cliché Greetings: "I hope this email finds you well" is the quickest path to the archive. - Spray and Pray: Mass emailing is to networking what fast food is to fine dining. Just don't. - NDA Front Gates: Trust is a two-way street; let's have a conversation first. ✅ Now, for the wins – your DO's for higher open and reply rates: - Be Direct: A short, sharp message with investors name, fund, and focus catches attention. - The One-Pager: One page that sings your startup's story is music to an investor's ears. - Align Our Stars: Ensure your startup's focus matches my investment thesis. - Persistence with Grace: A thoughtful follow-up shows determination, not desperation. - Data Talks: Specific numbers and milestones speak louder than buzzwords. Personalized outreach is an art. As investors, we're looking for that perfect blend of passion, precision, and potential. Nail that, and you'll not only get your email opened – you might just get the desired call. #StartupTips #InvestmentOutreach #VCAdvice #Entrepreneurship #VibraniumVC

Founders: 90% of your fundraising cold emails suck. Here’s how to write one that actually gets a response. 👇 I’ve helped 400+ founders raise over $1B in follow-on funding and I still see the same mistake every week...spray-and-pray emails that read like this: "Dear [Investor], we’re building the future of [buzzword]. Let me know if you’d like to connect." No context. No hook. No chance. If you’re reaching out cold, your job is to make it as easy as humanly possible to say yes. Here’s the structure I recommend (and I promise it works): ✉️ Subject: Your Name (Startup Name) <> Their Name (Firm) → The Why Start with why you’re reaching out to them. Did they invest in a similar space? Say so. Did they write something that resonated? Tell them. → The Hook In 1-2 sentences, what are you building and why is it exciting right now? Say it in plain, simple language that even a child could understand. → The Proof Drop 2-3 bullet points that highlight traction, team, or any other credibility or momentum that the company has. The Ask → “We’re kicking off our pre-seed round and would love to set up time for an intro call to share more about what we're building." Bonus Tip: Be personable and human. It gets you A LOT farther than you think. P.S. Want me to review your cold email? Drop it in the comments or DM me a Google Doc. I’ll pick a few to edit live. 💜

Founder learnings part 10 - how to get world class email open rates in 5 easy steps! 6 months ago we knew nothing about email - now we send more than 100k emails per week and have maintained a 67% open rate for the last 3 months straight (industry standard is 18%) while holding sub 0.3% spam rate in postmaster. Here's what I wish I'd known 6 months ago, all manual builds + no klaviyo! : 1️ - Mail warming actually matters way less than you think in 2025 - because your score is way more linked to the domain/IP combo than just the domain, so, if you're using a 3rd party mail warmer and then switch across to klaviyo or some other sending tool, it basically won't matter - you've lost the score rep you built on the warmer. This is why we roll our own. 2 - Every send should be transactional: As in - every email you send should be triggered based on user interactions within your ecosystem, no cold-sending. Hitting their inbox at the exact moment they’re most likely to engage makes all the difference, put hooks all over your site/app/extension/anywhere else you can, watch for form entries, then trigger sends based on that - WAY better than blasting 100k out all at once from something like mailchimp. 3 - Pre-check for bounces – Sending to invalid emails hurts your sender reputation and increases spam filtering. Use services that check if an email will bounce before you send it, so you’re only reaching valid inboxes. This keeps your list clean and improves long-term deliverability. 4 - Prune your cohorts – This one should be obvious but most email lists have dead weight that drag down performance. Set up automated scripts to constantly remove unresponsive users and refine targeting based on engagement levels. The more dialed-in your segments are, the higher your open rates will be. 5 - Ramp sends REALLY slowly – There is no way around this. Even if your list is solid, blasting too many emails too fast will tank your deliverability, you have to be so slow and steady with this. Industry standards say 15% per day but we go slower and have done 8-10% on warmed domains to avoid spam filters. A slow, steady ramp ensures you build sender trust and maximize inbox placement.

I’ve sent 1,000,000+ cold emails. These 10 tips actually got replies: Here’s what works in 2025 (and what to do when it doesn’t) 👇 1/ Subject line = first impression – Keep it under 50 characters. – No clickbait - people are smarter than that. If it’s not working: → A/B test 5–10 subject lines per campaign. → Test clarity vs curiosity. → Subject lines with clarity see 18–22% higher open rates on average. 2/ Nail the opening – Show you understand their industry. – Mention a real pain point. If it’s not working: → Add a personalisation token (e.g. “Saw you work with fintech startups”). → Personalised openings can increase replies by +32%. 3/ Get to the point – No intro essays. – 1 sentence: who you are + why they should care. If it’s not working: → Cut intros to under 15 words. → Best-performing intros are under 10 seconds to read. 4/ Make it about them – Focus on their goals. – Then say how you help. If it’s not working: → Emails where “you” appears 2× more than “I/we” get +21% more replies. → Use job-specific outcomes (“hiring manager” ≠ “founder”). 5/ Offer real value – Be specific: “We cut onboarding time from 14 days to 3.” If it’s not working: → Add a hard number: revenue, time, headcount saved. → Templates with quantifiable outcomes = +44% reply rate increase. 6/ Keep it under 100 words – Best-performing emails: 60–80 words total. If it’s not working: → Remove every “fluff” word. → Reading time over 25 seconds drops replies by half. 7/ End with a real question – Instead of “Let me know your thoughts”, try: “Would you be open to a quick 15-min call next Tuesday?” If it’s not working: → Add a calendar window. → Questions with time-specific CTA = +27% increase in conversions. 8/ Follow up smart – Wait 3–4 days between follow-ups. – Send no more than 3 total. If it’s not working: → Follow-ups drive 60% of total replies. → Change subject lines after the first email. → Use new angles: results, case study, or question. 9/ No attachments, no jargon – Attachments = 2.5× more likely to trigger spam filters. – Jargon reduces trust, especially in first touch. If it’s not working: → Run your copy through a 6th-grade reading level checker. → Emails at this level have +40% better engagement. 10/ Test relentlessly – Subject lines, intro, CTA - all fair game. If it’s not working: → Test 1 variable at a time (A/B logic). → Top-performing clients test 3+ variants per campaign. → Small tweaks often lead to >2× reply lift. If you found this helpful, follow me for more cold email tips and behind-the-scenes experiments. Also check out Outreach Today - First Hosting for Cold Outreach, the tool powering results like these.

“Raising cold doesn't work." It works. Your emails just get binned before investors open them. Here are 15 checkpoints for a cold email that gets opened by your dream investor: (Save this for later) 1️⃣ Avoid generic greetings, like "Hi there" or "Dear Sir/Madam". It's too generic and lazy. Find out who the spokesperson is. → Use the first name of your recipient e.g. "Hi John". 2️⃣ Don't call people Sir or Madam. It's stiff and outdated. In most cases it's perfectly fine to go by first name. → Use the first name, except with Dr titles (frequent in deeptech, biotech, medtech) 3️⃣ Don't apologize for sending an email. It's unnecessary and it weakens you before you've started. → Drop "I'm sorry to disturb you" and go straight to the point. 4️⃣ Don't outsource VC outreach. Investors invest in founders, not middlemen. → Especially at early-stage, the CEO should be sent from the CEO's email and signed by him/her. 5️⃣ Keep the email body under 1,000 characters. It's a universal rule: the longer the email, the less reply you get. → Cut everything until the body fits under 1,000 characters. 6️⃣ Don't ask if you can send your deck in the next email. The extra step just adds friction and delay. → Attach your pitch deck to begin with. 7️⃣ Don't add legal mentions to your company name like legal structure (Corp., SAS) or trademark (TM, ©). Tags like these make you read like paperwork, not a founder. → You are the CEO of LinkedIn, not LinkedIn Corp. or LinkedIn TM. 8️⃣ Use simple words when describing what your company does. Jargon makes investors work to understand you, and they won't. → "We are X helping Y in a Z way" - as short as possible. 9️⃣ Don't make vague statements like "the growth has been impressive" or "traction is encouraging". Vague claims read as hiding weak numbers. → Give numbers: "MRR has grown 25% MoM over the past 12 months". 🔟 Don't mention a 20x growth when you've just grown from 1 to 20 users. Investors won't be fooled and it's a sure way to lose your credibility. → Only frame growth in a way that holds up to a follow-up question. 1️⃣1️⃣ Never write long paragraphs. Walls of text get skimmed or skipped. → Write short paragraphs. 1️⃣2️⃣ Use bullet points. They let the VC quickly parse your email for the key points. → If you want to expand on 2-3 key points, put them in bullet points. 1️⃣3️⃣ Don't close with "I'd love to meet and exchange notes in the spirit of networking". A weak ask signals you don't believe in your own raise. → Try a confident close: "Looking forward to showing you how XXX will change YYY". 1️⃣4️⃣ Keep your signature short. A cluttered signature distracts from the message. → Cut the fax number and the five social accounts. 1️⃣5️⃣ Don't stuff the email with links and images. They distract the reader and trigger spam filters. → Keep it to 1 link (your pitch deck) and zero images. Get these 15 right and your reply rate takes care of itself.

Great emails fail for one simple reason, bad timing. Not the design. Not the offer. Just... poor timing. You can write the best copy in the world. But if it lands at 3 AM or during a busy workday? It gets ignored. Or worse—leads to unsubscribes. Let’s fix that. Here’s a proven timing strategy built for ROI. The Real Problem? Most emails are sent by gut. – Tuesday at 10 AM? A myth. – Sunday night hustle? Random. – Whenever your calendar’s free? A guess. What you need isn’t advice. You need data. The 6-Part Framework for Smarter Send Times 1. Audience → Know them like a friend. Ask: – What’s their timezone? – Are they a CEO or side-hustler? – Do they check email in bed or at lunch? Use tools like micro-surveys and lead forms. Start segmenting smart. 2. Timing → Test. Don’t assume. Run a 7-day send test. Same message. Different hours. Track open, click, and buy rates. Then do it again—by segment. Don’t sleep on weekends. Some buyers convert best on Sundays. 3. Data → Let numbers guide you. Monitor more than opens: – CTR – Conversions – Unsubs – Time-based heatmaps A/B test with one tweak per send. Then document it all. Weekly → Monthly → Quarterly. 4. Strategy Layer → Build for long-term. Don’t plan campaign-by-campaign. Plan lifecycle-by-lifecycle. New leads get instant value. VIP buyers get prime-time offers. Sleepy subs get weekend reactivations. Turn timing into a system. 5. Tactics Layer → Execute daily, tweak fast. Check heatmaps before you hit send. Watch real-time data. Double down on hot hours. Avoid cold zones. And don’t forget: Strong timing won’t save bad copy. 6. The Mind Boxing Model → One Framework to Rule Them All Think across 3 verticals: Audience. Timing. Data. ♦️ I work with early-stage founders who feel stuck. → Not sure what’s next → Can’t get past the plateau → Ready to grow, but not sure how If your finances feel foggy, or your biz feels flat... Let’s talk. I help you build clarity and momentum.