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How to Cold Email Investors [video] (ycombinator.com)
309 points by sahin-boydas 22 days ago | hide | past | web | favorite | 86 comments



As a VC, I strongly agree with all of these tips except for the one about tracking opens. Like most people, I don't love being tracked.

I especially agree with the first tip about a cold email's goal being to pique enough interest to get a positive reply. The goal is not to convince someone to write a check on the spot by writing a 10-page email -- that's an unattainable goal and no one is going to read a cold email that long.

To use an analogy, a cold email should be like a movie trailer -- or even a movie poster. A movie poster doesn't give you a long summary of a movie, but it gives you enough info to decide if you might be interested. (I wrote a little about this analogy a few years ago: https://www.codingvc.com/what-movies-can-teach-you-about-pit...). A good rule of thumb is to list ~3 bullet points that you think make your company stand out the most. These could be about the team, the product, the traction, or anything else.

It's also good idea to mention your company's stage. Lots of emails don't mention what round they are trying to raise or how far along a company is, and most investors operate in a narrow band. Roughly speaking, pre-seed investors are a fit for <=$1.5m, seed for $1.5m-$4m, and Series A beyond that.

If you send emails from your startup's email address and use LinkedIn, add the email address to your LinkedIn profile so that people can search by it. If your name is not unique and your company name isn't in your LinkedIn profile, people won't be able to look up your background and experience.

Finally, light personalization helps, faux personalization hurts. Light personalization could be a sentence like "It looks like we both went to Dartmouth!" (human connection) or "I saw you invested in companies A and B, which help accountants and lawyers bring their paperwork online. Our company is helping auditors bring their paperwork online." (shows effort/research). Faux personalization is stuff like "I did some research and based on your investment thesis I think you'd be a great fit" (intentionally vague and can be sent to every investor) or "I see you invested in MediaStartupA and SaaSStartupB, so I think you'd really like my RoboticsStartup" (name-drops startups, but the startups are random and completely unrelated).

FWIW most of these tips are not specific to emailing investors, and they can apply to cold emailing anyone.


The irony of a VC saying he/she doesn't love "being tracked" is the whole controversy over the Superhuman tracking pixels. IIRC most of the defenders of the company's practice were VCs (both investors and not)...


I think aggregate tracking is interesting because it can be informative without violating privacy. For example, for a sales or pitch deck it might be interesting to see if certain slides captures a lot of attention or don't resonate at all. But I don't like individual tracking where it feels like someone is looking over my shoulder while I view a deck. I don't like that Superhuman did that kind of tracking by default, either.


As a VC, how to you balance the cost of the search for profitability against the unknown costs of harm to the user in the future from certain profitable models?


Do you mean would I invest in a company that's bad for the world but can make lots of money? I try very hard to avoid those. There are more than enough companies that can make money doing good things.


>As a VC,

Have you ever invested - transfer has cleared, they have the money - into a company that cold emailed you?


One so far (a company called Pex, the founder's HN handle is doh). Always looking for more. :)

We've also done a decent number of investments through accelerators that were not YC. That's somewhere between cold inbound, cold outbound, and warm intro.


At YC we do this all the time. Its our bread and butter :)


This is the real question, I would like to see VCs here commenting on investments they made that were not through their network.


a higher chunk of cold email i get don’t bother explaining what the company actually does. please don’t do this.

when i do see an interesting company, i want to read more immediately. when a deck or something isn’t included, it kills that momentum. you don’t have to include everything, just give something.

i skip everything that has clicktracking on links. it usually means that it wasn’t a targeted email and was sent out by a mailing list.

edit: another thing people do is have a “VP of fundraising” or someone external send the email. this is also a bad look. it should be from a founder or the CEO.

edit edit: i will honestly review your pitch if you email me and reference this thread. generally i don’t give negative feedback because i don’t think most founders really want it.


> a higher chunk of cold email i get don’t bother explaining what the company actually does. please don’t do this.

PG had a recent tweet that touched on this in response to someone pitching an intentionally ridiculous product (at least, that's how their tweet read to me):

"Believe it or not, this is not the worst pitch I've received. It's (a) concise and (b) I can tell what your product is. Those two alone may push it into the top half." [0]

It's apparently harder than it should be to succinctly explain what the company does before explaining why it's a good investment or why you need investment.

[0] https://twitter.com/paulg/status/1175837682242609157?s=20


Perry-Air! Damn, I never realized how many good ideas are hidden in sci-fi movies!

But then people are selling glacier and iceberg water in bottles or ice cubes, so...


The marketing is done for you. All you have to work on is the tech.


yes. a LOT of them go for a cure teaser.

i simply jump to the conclusion that the founder is bad at communicating if they can’t get this one detail across.


cure -> cute


It is extremely difficult. And extremely important. Until you can succinctly explain what a company does, you don't understand the problem/customer/solution well enough.


> generally i don’t give negative feedback because i don’t think most founders really want it.

As a founder, I strongly disagree. The feedback I care about most is negative feedback. Negative feedback helps me improve.

If I don't agree with your negative feedback, next time I'll communicate better why. If I agree, that helps me address the flaws in the business sooner. I'll be grateful, not upset. Just like with user/customer interviews.

The legal risks that dissuade employers from giving feedback to job applicants don't apply for investors. If you're trying to keep your options open to invest later, I'd rather return to someone who pointed out a flaw that I then fixed which led to success.

I realize most people in general don't react well to negative feedback, so maybe this is just me, but I imagine there are others out there like me.

" If you can trust yourself when all men doubt you, But make allowance for their doubting too; "


There isn't as much of a legal risk, but it's definitely mitigated.

In addition, the feedback they gave is now written. What if the founder lacks social etiquette and tweets "VC Y said my idea sucks because Z [some charged topic]"? If you look at the missed out on investment X/Y/Z emails that VCs sometimes release (anti-portfolios), you'll notice almost aways the releasers asks for permission first. VCs network effects largely need to be polished and appear to be knowledgeable about sectors -- giving feedback to a random startup that might be horribly wrong would hurt that reputation.

It makes sense as to why many VCs don't give feedback.

That being said, the answer is to never ask for direct feedback. Instead, you should have a middleman and backchannel. Ask the middleman to find out why they didn't like X -- this generally works. The middleman is impartial and can be objective (versus the founder who is often defensive) and is able to extract truth.


unfortunately, engaging deeply after i have decided i'm not interested is too expensive in terms of time.

if i think i might want to invest later then i am much better off spending the time fixing it or understanding it better now and then invest now.


A lot of people say they want negative feedback, but most of those people are human, and they react the same way most people react to negative feedback.


Re: tracking - I don't have a huge problem with email marketing tracking aggregated opens in theory, but unfortunately, it's far too easy to use the same technology to track personal emails, which does bother me. So I turn off images. Really wish there was a better way to manage this that made it simpler for the layperson to understand the tradeoffs.

I don't really have a problem with click-tracking anywhere, but as I work through the logic, I can't really tell you why. It isn't really any different than open tracking. Thinking more about it, I guess I'm ok with tracking that I landed on a URL via a referrer or UTM, as this is tracking how someone arrived at your property and is ostensibly less personal, not whether or not they read the letter you sent them. I'm less ok with tracking that person clicked link in email you sent them. Again, speaking specifically about 1-1 communication, mass email is a separate issue (that I have some problems with, but they're not equivalent to me).


specifically, don’t love the mass email pretending to be specific 1-1 email. mostly i dislike the asymmetry of people to do a very little work and give me a bunch of work (having to review the company.) i am much more likely to do the work if i think they were talking to me specifically, especially since that means there is a much greater chance that it is a match. much the same as spam, i guess.

the tracking itself doesn’t bother me too much. i do type in my email to docsend decks which is also tracked. i do not like the fact that the docsend decks disappear though. i suppose that is a different issue.


> specifically, don’t love the mass email pretending to be specific 1-1 email.

In the context of an email soliciting a 1-1 interaction, I completely agree.

I'm ok with a marketing email personalizing itself to me ("Hey <name>, from <name> at <company>.")


How to cold email investors:

1. Don't.

1.a. Self fund and co-develop with a team that understands that if your company is the point where you have to cold email investors, you're going to be so strapped with shitty contracts and lose so much equity that you're absolutely never going to make any money on an M&A event and you should start over.


If you don't mind my asking, what sort of terms can you expect to get with an angel investor? What ownership stake vs funding levels are normal, and is there a point at which you revoke funding, or is it delivered all at once?

Do angel investors typically fund startups that don't have great capital expenditures?

Is this type of investment sought in the initial bootstrapping, before VC funding?

How much of a prototype is expected? A fully working product with customers?


Angels come before VCs. Offer 10 to 30% understanding that in the end they will come out with 5/10%.

The amounts are smaller so anything under 200k you will probably get it all at once.

Angel's fund companies they believe in.

No investing before a bootstrap product unless you have a background or more to offer.


Thanks! That clarified my understanding. :)


ok my inbox asplode even more than usual. oof


Sorry in advance. Thanks for offering this to us.


What do you know, maybe you got a million dollar idea in there


Sending an email your way!


Please revive Delicious.


Pinboard owns Delicious now.


it is only one step on the way to owning all of us. never compete with pinboard.


I sent you my pitch :)


Please don't track opens and don't use the 'confirm receipt' flag. Both of these trigger many spam filters and your mail will possibly not get through.


And maybe just me but I doubt it - It leaves a REALLY bad taste in my mouth getting the alert that the email read receipt is being tracked.


this is so egregious to me i didn't realize email tracking like this existed.


It can be a useful tool in appropriate situations. It's not inherently bad.


It should always be opt in


What spam filters do these trigger? I have never seen any evidence of open tracking resulting in spam flags.


That's because you count them as part of that overwhelming "never opened" group.


Same. Server side and client side seems to not care.


Even those "image-based" opening trackers? I do agree that the 'confirm receipt' flag is not a good idea.


Block it.


Was half expecting this whole article to be "don't"


It's always surprising to me how many people in tech need to seek investment. Saving some scratch over a few years of paid employment, then bootstrapping, seems like a seldom-traveled route.


I tried that once, and it works for a certain kind of business and a certain kind of developer.

Basically, it works if you're building the kind of thing that you can build, and take to market, in 50% of your time with minimal or no assistance. The other 50% of your time will be on business development tasks. Such an approach works when you're a great software developer, and a great businessperson, and disciplined enough to know what you can do as a single person with a small budget.

These are things like small websites, small apps, little doodads that can be manufactured via contracting with someone else and sold on Amazon, ect, ect.

There are plenty of interesting businesses that can be built that way, and plenty of interesting businesses that can't be built that way. (Just try to build something that needs hard capital for tools, like a chip fab!)


Anecdotally, I've seen (2) companies fail because they refused investment money. The usual avenues of failure are:

- You have a few major clients monopolizing your time, and you can't afford additional resources to break out of the pattern.

- You prove the viability of the product and create a market, but a venture-backed/larger competitor eats your dinner.

I'm not saying it's always correct to accept funding, but it's pragmatic to consider it.


> Saving some scratch over a few years of paid employment, then bootstrapping, seems like a seldom-traveled route.

Probably because most people don't in their wildest dreams have the kind of spare cash left at the end of the month to do something like this.


Indeed; I should have been more specific in referring to people already working in the Bay Area technology scene, where salaries are quite high.


And cost of living in the Bay Area is quite high to go along with it. Unless you're single with no kids, it's probably not very feasible for most people.


Very few people with kids to support should try this no matter where they live. When it just you (a supportive spouse with a day job can be helpful, but supportive is key) the worst case can get pretty bad: you can sleep under your desk in the cheapest roach apartment in town, eating beans for dinner - living on less than 1000/month for everything (you are taking a risk that you won't need the insurance you are skipping). This allows you to live for a long time on very little cash flow. Your bankers will wonder how you can run a business with so little money in the bank but you will always be on time for your minimal bills. It won't matter that you can't afford activities, because other than your daily 30 minute exercise in the local park you won't have time for any activities (even this is optional, but for your health I recommend it). Hopefully the business takes off after a couple years and you can settle down to a more normal schedule.

Once you have kids to support it gets harder. Not only are there more bills to pay, spending so much time on business means you miss many once in a lifetime opportunities to see the kids as they grow.


"Once you have kids to support it gets harder. Not only are there more bills to pay, spending so much time on business means you miss many once in a lifetime opportunities to see the kids as they grow."

The Torah confirms:

"... a man should build a house, plant a vineyard and then marry a wife” (Sotah 44a).


You’re not going to see a post from a seed accelerator on said seed accelerator’s hosted forum about self-bootstrapping without investors hands in the mix though.

You’ll get all sorts of responses leading the other way:

“no one has money to bootstrap a business!”

Or

“An investor has special capital and asset powers you need it”

Which is nothing but FUD.


you are failing to see half of the equation -- capital supplied companies can make moves that are not an option for boot-strap, and those moves are used aggressively in many cases. Secondly, capital is abundant in the West (perhaps too abundant) .. those seeking return on that capital are making the paths that lead to this system.


Using other people’s capital has better EV and a better worse case outcome than completely self-funding. Not that every company needs to be venture backed.


There are a couple of reasons

A) They have some ideas they want to launch NOW; not 3-5 year down the road.

B) Saving money won't make a dent in what's needed

C) They don't have access to rich family or friends.

In my local startup scene I've noticed a lot of founders coming from well-paying backgrounds. Ex-Finance, consulting, and such - usually they have pooled money with co-founders from similar industries. Often times in combination with loans or similar from family or friends.

Or even more often than that, you have already successful founders that are spending money from previous sales / exits.

In either case, those tend to be the people with hundreds of thousands to spend.

For regular folks with normal salaries, it's cold-calling every investor under the sun.


Also in the US for profit healthcare costs are prohibitive unless employer supported.


But is cold emailing worth it? Most investors claim that they (and most others) never respond to cold emails. It's been said that reaching an investor through their network is a kind of mandatory IQ test.


I've mailed VCs as a first-time founder and got a response or follow-up meeting.


In what year though? I feel like a lot of VC's have adopted this trend of forcing you to befriend random people they have funded before, to introduce you in. Not because it is actually a good method, but because they saw a few popular VCs were doing it and jumped onboard.


ditto


Almost as bad as not telling what the product/service is, is explaining it in very generic terms. "We provide life as a service" or "Integrate across multiple platforms" or something.

And, don't defend yourself if someone points it out! (Food is life as a service, get it? That's what food is!)


From the outline I miss: Stroke their feathers.

I have quite a few interesting discussions with people in academia whom I've never met before but work in something I'm interested in at that point in time. Quickly explaining what you've read and why (hint: their articles!) I feel helps in moving from "homework"-question to might be interesting. I always figure that most professors mainly meet people in their circle and not a lot of people outside, so in the basis are happy to explain something to someone that comes across as authentically interested.


One way to think about this is the "barbell strategy" due to Nassim Taleb. Make emails incisive and direct; decks should be contextual and comprehensive.


I built a machine which is now being prototype-tested by a government in Europe (law enforcement). How do you go about raising cash to build more machines and reach out to more governments in other countries?


Get in on one of the many EU startup programs. There are some people who specialize on filling up the papers exactly as the bureaucracy wants it. I don't think the money comes with any strings attached (other than having to show you spent it on what you said you were going to spend it on), but do your own research.


How do you determine market size? It seems like it's an inflated best guess for a relatively unique product.


Good advice, but one question. Is there a list or consistent way to reach out to various investors easily?


a video about how to do email? what’s next, an audio lesson on how to send a fax?

what’s worse than no docs? video docs.


Something I wrote about how to approach investors. Not looking to promote the place it is at. Anyway...

1. Build bridges with investors before you may need to cross them, ie. Don’t go to them when you need the money. There are a multitude of angles to use, but each angle has to come from a core place of self-less and selfish interest. Know what they want and need, know what you want and need. Each angle will also dictate how early you can / should get on their radar.

2. If you are introducing your startup to them, then around 6 months. If your angle is to aid startups in their portfolio, introduce startups to them (filter them, don’t send them any and all), or introduce family offices looking to put funds into a pool; then you can contact them a lot earlier.

3. There is another way that you can connect with investors, “get an intro to us via someone in our network”. With some investors this will be the only way.

4. Note the investor landscape, find out their investment thesis. See if their portfolio has any that could be competitors, any synergies, etc.

5. Find out the required milestones (for your current stage and the next one). This can be a difficult one to find out, for it can pin some of them down a bit too much, especially when they take so many other things into consideration. If they don’t mention it on their site, and there is nothing in Crunchbase et al, you’ll have to ask them down the line.

6. Find out more about the appropriate partner at the VC firm whom is involved in your niche. If you can’t find the appropriate partner, aim for the top, and have them point you in the right direction.

7. Acquire information about the partner and use it to formulate an email that is about them. I will typically provide a few of my thoughts on something they said in an article. They will be genuine thoughts. No brown-nosing, no compliments for the sake of it, etc, etc.

8. Find out the firms current position in the fund life-cycle: are they open to new investments, only open to portfolio synergies, only follow-on funds left, etc.

9. If the investor’s portfolio has competitors and/or synergies find out where they stand on this. Some will be open to funding competitors, some won’t. If so, find out how things are kept ethical and above board.

10. Find out what their investment approval process is; stages, duration, etc.

11. Ask them for their due diligence (DD) checklist, and work on that organically. Until then, use this one: https://seraf-investor.com/compass/article/seraf-toolbox-due...

12. DD goes both ways, so find out what you can about them, what they are like after investment.

13. Prepare a presentation deck, not a pitch deck, and present it to your team. Let your team know beforehand, and to attempt to trap and flummox you as you walk them through it.

14. Update the deck and send it to a few of the investors, and use them as data points. The reason it’s not a pitch deck is because the deck should explicitly state that you’re not looking for funding at this moment in time.

15. Send it to ones you either have good relations with, and ones that do not fund in your geographical area. There are some gems out there who will go out of their way to aid you and to give you feedback. Granted they may not know the launch country market, but they will know the startup niche. Basically work your way inwards to the set of investors you are targeting, using the feedback to hone and refine startup / deck.

16. If you don’t want to slice by geography, or want to start closer to home, slice the investors into tiers. Can be based on many things, niche relevancy, track record, connections, dumb or smart money, etc. Work your inwards from the ones you least want.

17. Once you get to the set of investors you are interested in, same thing, not looking for funding yet. If it’s a decent startup / deck you could be asked to come in for a chat, or to keep them updated as to your progress.

18. If you are going to go down the path of external funding, then investor pre-validation is vital.

19. Keep them informed as to your progress, monthly update is fine. Keep it short and to the point. Be brutally honest, so good and bad, hits and misses.

20. Even if your angle of approach is for your own startup, keep an eye out for any startups that you think they would be interested in. Same thing with investors and family offices, some of them go solo (or dedicated fund manager), some want to put their funds into a pool.

21. When you are ready, send the pitch deck.

One last thing, no one ever got funded off a pitch deck. Napkin maybe. but not a deck. It's a foot in the door at best. Besides, founder(s) of an early stage startup, they're investing in you.


Serious q: What's the best way to track opens?


Praying to beelzebub that the reader has “download images” enabled in their email client.


How this typically goes. Congratulations, you got past my filter. deleted

I doubt tracking opens would be a useful metric at all.


Serious a: Use something else than e-mail.


I'm sorry, based on my personal experience I consider this bad advice. Investors don't cut checks to companies that cold email them. It's a waste of time.

If you are really committed to doing this, there is one way you can do this. Concurrently and genuinely make a company2 and try to raise money for it. Send cold emails only for company2. It doesn't matter how great company2's business plan is, of course. You'll never raise money for it this way. On the last slide list other companies with similar initial growth propositions, the logo and name are enough: Facebook, Uber, Company1 etc.

While the investor will throw your pitch deck in the trash, regardless of how great it is, as they do so they'll probably get out their checkbook for Company1 without even talking to them. (Based on your last slide.)

Investors behave a bit like sheep, I'm afraid.

At any rate: don't cold email them but if you must this is the only way I would ever go about it.


Don't forget the importance of negging.


What do you mean?


Its the practice of insulting someone to achieve the reaction you were originally looking for.

It is a manipulative practice that aims to break down the self esteem of someone that would otherwise dismiss you, so that they want to validate themselves to you to remain attractive in their own head. All while you just wanted the attention to begin with. A little different from trolling, where you rile someone up just so they embarrass themselves. With negging, you want them to want validation from you and you want a relationship with them.

It is a gender-neutral pick up art, more commonly taught by men in communities that want to meet women. Try not to fall for it. Try not to be manipulative. It also works.

The pick up art community overlaps with the NLP community which applies their speech hacks in professional and career settings.


OP is probably referring to a conversational technique where one person tries to gain rapport with another by (sometimes slightly) insulting them. It's more common in the hookup scene, "pickup artist" scene, etc, FWIW.

I'm not aware of its usage in VC pitching, but does not sound like a good idea.


It’s a reference to this scene from Silicon Valley:

https://youtu.be/N6Zz-Nkkaxc


Ah got it. I had forgotten about this. What about bsack slamming? Does it work these days?


What percent of tech investors enable "Display Remote Images" for their email?

Being frank on the subject, I'd look down on anyone who claims to be knowledgeable about technology yet enables remote images, i.e. open tracking.


Why is that? I f you work at a company where you are constantly emailed screenshots, even if you are aware that image tracking is not in your best interest are you going to bother with this inconvenience?

Constantly switching email format modes is super annoying to clients and everyone you work with.


> Why is that? I f you work at a company where you are constantly emailed screenshots, even if you are aware that image tracking is not in your best interest are you going to bother with this inconvenience?

Email includes the ability to incorporate attachments[1] including images that are displayed inline. Those show up just fine. This is specifically in regards to remote images.

Having the images in the actual email also has the advantage of keeping a record of the assets associated with the conversation. As opposed to having them disappear from the remote location at some arbitrary point in the future.

[1]: https://en.wikipedia.org/wiki/MIME_attachment




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