🤙 Hey, I’m Ivan. I write about how top 1% startups raise capital and grow.
Welcome to a Fundraising edition.
This week’s sponsor is AI CRM Attio (raised $52M from Google Ventures):
Attio is the AI-native CRM for the next era of companies: Connect your email and calendar, and Attio instantly builds a CRM that matches your business model — with all your companies, contacts, and interactions enriched with actionable insights.
With Attio, AI isn’t just a feature - it’s the foundation. You can do things like:
Instantly prospect and route leads with research agents
Get real-time insights from AI during customer conversations
Build powerful AI automations for your most complex workflows
Fast-growing companies like Granola, Modal, Replicate and more are all experiencing the future of GTM with Attio. See it for yourself.
🌊 How not to raise money
“All I want to know is where I’m going to die, so I’ll never go there.”
- Charlie Munger
Reading “Poor Charlie’s Almanack” between sets this summer (full corelord).
One idea stuck: inversion.
And it hit me, this is one of the most powerful mental models for fundraising.
Because while fundraising can feel subjective, there’s a fixed set of moves that almost guarantee failure.
So, here’s the checklist on how to fail at fundraising:
Researching who to pitch to:
Never ask yourself if your business needs venture capital Vs other options.
Don’t spend time researching and targeting not just the fund but the specific investors that tend to invest in your space and match your vibe.
Never ask for a warm introduction through a mutual connection.
Never ask portfolio company founders from your target fund what it is like working with them.
Never personalise your outreach or deck.
Do not batch your outreach, target all the funds all at once.
Do not use an AI CRM and a process to keep notes, reminders, cadences and so on. Always ignore all b2b sales processes and tactics to ensure proper targeting, batching, and follow-up timing.
When you get a reply or someone requests a deck, always ask for an NDA.
Preparing your pitch:
Do not make a distinction between a first Vs second / third / IC meeting.
Assume that talking to an analyst is a waste of time. Believe that they don’t have any power internally to be your champion, and therefore don’t research them.
Never spend time understanding a VC’s business model, especially to know how they think and what their incentives are (from intern to GP).
Use as much text per slide as possible.
Use lots of confusing colours and shapes in every slide.
Give them the impression that you’ve spent more money and time on the deck’s design than thinking about what problem to solve.
Make the deck at least 30 slides, include a large appendix.
Don't spend any time preparing a good story explaining why you and your team are the right humans to solve the problem you are attacking.
Never prepare hard questions.
Do not practice telling a story about the market, the twists and turns it has taken, and which obstacles you are likely to face.
Be as unclear as possible on your engagement metrics slide. Make sure they don’t get a clear view on traction quality.
Bonus: Try including VAT in your MRR or exchanging “committed revenue” for your “deployed revenue” in your ARR.
Don’t include any information regarding your cap-table and any issues that would be uncovered when they ask for it.
Bonus examples: dead equity, “advisor equity with no skin in the game $”, excessive early dilution via accelerator / incubator etc.
Don’t share a solid data room or pitch deck ahead of time (don’t use this template for Series A in particular).
Pitching:
Always be way too early (especially in-person) or too late (especially online).
During the pitch, ensure you never provide the bottom line upfront.
Don’t try to match the energy in the room. Do not check the vibe and adapt your messaging / speed (especially during intros) / tone / focus accordingly.
Make sure to never summarise your problem and solution in clear terms.
Use complex language with lots of buzzwords.
Under no circumstances tell a good story.
Don't provide a clear and contrarian view of the world.
Never stop talking.
Make sure to spend most of your talking time on the least important slides (like market sizing).
Never talk about the hardships and issues the business may be experiencing, make sure you don't bring them up proactively. Wait for them to flag them.
Don’t share information on any of the following points:
Cap-table issues
Debt raised and its terms
Past or ongoing litigation
Burn and runway
Be defensive about hard questions. Do not take the opportunity to display your wit / understanding / deep knowledge of the problem and how you are solving it when confronted with tough questions.
At the end, ask a bunch of questions. You can fail in many ways here, its an interesting one. You can fail by asking questions that show you haven’t researched the fund and people around the table, that make you sound “too eager”, that make you sound like you are trying to generate FOMO (smells from a km away) etc. Ignore that its a delicate dance altogether.
Make sure the meeting runs overtime.
After the pitch
Be very pushy. Don’t seek any balance in your timing.
Always sprinkle FOMO on your follow-up emails.
Tell other funds that you already have the commitment from a fund that hasn’t actually expressed any commitment.
Upon rejection, always burn all bridges.
Forget that it is totally normal to get tons of “No”’s and (hopefully polite, humble) rejections, and do not carry on with grace.
After the fact, focus on resentment.
Do not own any of the outcomes.
Don’t get back on the horse. Immediately throw your systematic approach to your fundraising process out of the window.
What am I missing?
I’d love to hear from you and what you’d like more of on here.
Just reply to this email, I reply to every single one of them!
🤙
P.s. join as a premium subscriber to get these and back the work:
🔒 Fundraising Frameworks — 3 frameworks to tighten your pitch
🔒 Founder Compensation Benchmarks — salary data from top founders
🔒 GTM + AI — How founders are rebuilding sales in 2025
🔒 HubSpot’s 0-$100M Playbook — $0 to $100M ARR sales strategy
🔒 Agentic Revolution — Deep dive into the next tech platform shift
🔒 AI Voice Agents — Market map of where capital and talent are moving
Love it!
Treat fundraising as a single event rather than a process.