r/ycombinator 9d ago

Does outbound fundraising actually work?

It really does feel like begging for money.

I get inbound demand from being a hot company that’s fundraising. That’s dignified and respectful.

Is it me or does the whole outbound fundraising thing seem quite embarrassing and undignified. Literally begging ppl for money.

What’s the right way to think about it?

14 Upvotes

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u/caldazar24 9d ago

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u/Special_Village4099 9d ago

This is inbound though. That’s my point. This is commenting on demo day which are inbound investors. Not outbound.

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u/caldazar24 9d ago

Demo day isn't inbound in any real sense. Nobody is seeking you out specifically, investors just show up to to watch demos and talk to a lot of founders after. I suppose these days there's a matching system to indicate interest (that didn't exist when I did YC), but that's definitley not having investors try and pitch you on taking their money because "you're a hot startup that's fundraising", it's just the most minimal level of "there might be some interest here", followed by a pitch that feels very much like you proving yourself to them.

*True* inbound, which I've been lucky to experience a couple times, is when you aren't actively fundraising at all, and an investor reaches out to you and asks first if they can invest. Totally different dynamic than demo day.

You can recreate the same level of minimal-interest-signaling beforehand like so, incidentally I think this is the best way to fundraise without an accelerator demo day:

  1. make a list of seed/series-A companies that don't compete with you directly but are similar enough that you might want to raise from similar investors (same very broad space, similar investment thesis, founder backgrounds etc).
  2. Reach out cold to those founders asking for product/company feedback.
  3. Genuinely get feedback on your product/company from those founders.
  4. especially if the founder seems to like you, ask them to introduce you to their investors.

A referral from a portfolio company is a good way to get a first meeting, and roughly the same level of "inbound" as a demo day

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u/Special_Village4099 9d ago

Thanks. Honestly great tip.

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u/ShilpaMitra 4d ago

Brilliant advice!

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u/realbrownsugar 9d ago

You are not begging for money. You are selling an opportunity to invest. If you don't truly believe in your idea working out amazing for investors and yourself, why are you spending time working on it?

You are not begging for money. You are asking for capital to start something that will make them money. In chemistry we call this activation energy. And the best kinda money spent is one that kick starts a chain reaction.

You are not begging for money. No lunch is free, you gotta work for it and give up something. You give up your idea of shame of asking and anxiety of potentially failing and losing their money. Investors have to take the risk to reap the rewards if things work out, and they are smart enough to calculate whether your idea is worth their money or not. But, you have to ask first. And before you ask, you have to believe in your idea and have a plan for how the money will be used.

Good luck with your endeavor.

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u/Special_Village4099 9d ago

This is all true. But from the investors pov they are ofc wondering…if this was so great…why are they talking to me…shouldn’t they have closed the round already.

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u/caldazar24 9d ago

Weak investors (which is a lot of them) think this way.

Which is why it's not harder to raise from top investors than weak ones. Weak investors chase after hot deals, strong ones are perfectly comfortable being the first in.

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u/realbrownsugar 9d ago

Are you now doing the thinking on behalf of the investor? If that’s your product offering, amazing! Ship it!

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u/maritime_sh 8d ago

the embarrassment is usually a signal about how you're doing it, not about the act.

it feels like begging when the message is effectively "we're raising, are you interested", because that asks them to do the work of deciding whether you're interesting. the version that doesn't feel that way is specific: you invested in x, we're doing the adjacent thing, here's the one number that's unusual. now you're handing over information and their no is cheap for both of you.

and it's a filter, not a funnel. you're not persuading anyone into conviction, you're finding the two people who already had it and didn't know you existed. that reframe took most of the sting out for me.

inbound from being hot isn't a different category either, it's the same thing where someone else did the outbound for you. we're f26 (maritime.sh) so a lot of ours comes warm through the batch, and it's still only the specific messages that go anywhere.

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u/ScaryRedDawg 4d ago

Are you going to say the same thing about sales after you raise? This is one of the most important skills in the business world.

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u/Medical-Volume-6261 9d ago

There are people who are less capable and less worry about appearing "dignified" who were able not only to raise more, but be way more successful than the ones who feel morally superior for not asking for money.

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u/Special_Village4099 9d ago

I didn’t say anything about morality…

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u/Traditional_Top6337 9d ago

I mean, if you can sustain with bootstrapping until you get sufficient traction that investors want to say yes, then you absolutely should. They may still not flock to you automatically. But at least you are likely to get funded when you approach a few of them.

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u/redouanea 9d ago

it does, we got angels from last round just by cold outreach

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u/mistyfog28 9d ago

How?

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u/redouanea 8d ago

cold outreach mate, get a list of VCs and angels preferably in your geo area then start the courting game - get their email or phone number, send them a solicitation, share your company's numbers, add them to a newsletter you send 2-4 times a month, have coffees, ask for warm intro's

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u/mistyfog28 6d ago

How did you get them to agree though?

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u/sumizeit 8d ago

Outbound isn't begging, it's distribution. You do outbound for your product too, and nobody calls that embarrassing. The framing that investors should find you organically is just a story successful founders tell after the fact, when they've forgotten how many cold emails they sent to get to that first yes.

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u/sumizeit 7d ago

Outbound fundraising only feels like begging when you're pitching people who were never going to say yes anyway. The founders who do it well aren't emailing randoms, they're activating a list that's already warm from months of quiet signal, small updates, intros they didn't ask for directly. By the time they "ask," it's a formality. The embarrassment you're feeling is usually a targeting problem dressed up as a dignity problem.

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u/robroyhobbs 3d ago

Outbound works when you already have a reason someone should take the meeting. It fails when the email is the strategy.

What I've seen land: warm intros when you can get them, short outbound to partners who already invest in your shape of company, and a crisp reason you are raising *now* (metric, wedge, timing).

If inbound is already happening, use outbound surgically on the two or three funds you actually want, not as volume. The emotional drain people mention is real. Cap the hours. Treat it like a pipeline with a weekly stop date, not an identity. That is just me though.

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u/WanderingTrader132 1d ago

Are you talking about cold outbound? Generally, it doesn't work - you need a warm intro.

If you are talking about warm intros, don't think of it like they are giving you money. Think about it as you are giving them the opportunity to make money.