
How to Cold Email Investors [video] - sahin-boydas
https://blog.ycombinator.com/how-to-cold-email-investors-michael-seibel/
======
lpolovets
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...](https://www.codingvc.com/what-movies-can-
teach-you-about-pitching-to-investors)). 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.

~~~
myguess
>As a VC,

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

~~~
lpolovets
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.

------
joshu
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.

~~~
mushufasa
> 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; "

~~~
jeffshek
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.

------
jacquesm
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.

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

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

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

~~~
human20190310
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.

~~~
chrisseaton
> 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.

~~~
human20190310
Indeed; I should have been more specific in referring to people already
working in the Bay Area technology scene, where salaries are quite high.

~~~
dave5104
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.

~~~
bluGill
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.

~~~
rsync
"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).

------
halfway
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.

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

~~~
threwawasy1228
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.

------
omarhaneef
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!)

------
wjnc
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.

------
acgan
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.

------
dt3ft
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?

~~~
icebraining
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.

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

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

------
techslave
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.

------
Ace__
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...](https://seraf-
investor.com/compass/article/seraf-toolbox-due-diligence-checklist)

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.

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

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

------
badadvice
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.

------
vernie
Don't forget the importance of negging.

~~~
objektif
What do you mean?

~~~
ralmeida
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.

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

[https://youtu.be/N6Zz-Nkkaxc](https://youtu.be/N6Zz-Nkkaxc)

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

------
koolba
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.

~~~
chapium
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.

~~~
koolba
> 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](https://en.wikipedia.org/wiki/MIME_attachment)

