This past year, Camperoni raised its pre-seed round. As a startup founder, and particularly as a female founder, I have been the lucky recipient of a LOT of advice about raising early stage capital. Some of this advice has been hugely helpful. Other advice, not so much. But time and again, moments during the fundraising process reminded me of a time in my life I try hard to forget: dating. The uncertainty, the anxiety, the ghosting, the search for that person / investor who thinks the sun rises and sets with me / my company. So having come out successfully on the other side (of both fundraising and dating), here is my advice to the founders coming after me.

Don’t Obsess

You’ve just sent your pitch deck to a few target VC firms, and now you sink into the familiar limbo of anticipation. Every day you revisit your inbox and check your Streak email tracking to see who has opened your last message. Are they interested? Are they indifferent? Did they come back to read it again? You’re left to speculate, overanalyze, and second-guess. Should you follow up? How soon is too soon? Will you come off as too eager or too disinterested? Stop it! Staring at your inbox is just as useless in fundraising as checking for a new text message from that great date last week. Your time and mental health are better spent getting back out there and meeting new people. Cast a wide net; there are plenty of fish in the sea.

Leave Them Wanting More

The dreaded first date — whether it’s with a potential investor or a new love interest, the stakes are high. You want to make a good first impression, but you don’t want to come on too strong. You hope the vibe is good and the conversation flows naturally.

At your first pitch, a lot of dating advice is strangely relevant. Be yourself. This is hopefully the beginning of a long relationship, so you don’t want to pretend to be something you’re not and end up in a match that just doesn’t work. Let the other person talk. Just because you’re the one pitching, doesn’t mean you should be the only person talking. Keep the initial pitch short to leave plenty of room for conversation. You will both learn a lot more about each other. Leave them wanting more. The goal of a first date is to see if you’re intrigued enough to spend more time really getting to know this person. The same holds true for a pitch. Pique their interest. Get them excited. Answer their questions. Then leave with them eager to set up the next date.

Are You Hot or Not?

In both dating and fundraising, animal instincts kick in: the more desirable you are to one party, the more desirable you become to others. It’s the classic case of social proof — if one VC is interested in your startup, others are bound to take notice.

In the early stage fundraising world, this is also true of the latest buzz words, verticals and business models. Don’t let it get you down if your business is not square in the middle of all the latest VC fads. Remember, there’s someone for everyone. True, those other startups are sexy now, but their hotness will fade. Find yourself a VC that looks past the fads and sees you for the solid, timeless, brilliant business you are.

Sometimes, He’s Just Not That Into You

You’ve been seeing a VC for months, but the relationship doesn’t seem to be going anywhere. Maybe he seems noncommittal and just keeps asking for more and more information. Maybe he’s ghosted you. Maybe you think the “yes” is coming any day now, but every time you bring it up, he seems to dodge the question.
He’s just not that into you. There, I said it. There might be a good reason and there might not be, but either way, he’s just not that into you. Maybe he likes you a lot, but you’re just not his type (enterprise SaaS, early revenue, with a FAANG founder) and he can’t get over it (they never do). Maybe he’s not looking for anything serious (and doesn’t actually have any capital to deploy RIGHT NOW). Or (gasp) maybe there’s somebody else (one of your competitors), and he’s just using you to learn more about the space. Whatever it is, he’s just not that into you. Accept it, and move on.

It Never Works Out, Until It Does

If you’re dating to get married, all relationships fail until one doesn’t. Failure is part of the process. Rejection is just part of the game. The same holds true for fundraising. You will not be the right match for the majority of potential investors you talk to. Industry, business model, team, timing, market size, deal structure, capital availability, and so much more needs to align to get to a yes. Luck plays a large part in whether you meet your match early on or after countless no’s. Stay positive and keep up that contagious optimism founders are known for.

When you do find the right match, sometimes you need to close the deal with a little pressure. In the dating world we hate calling it an “ultimatum,” but let’s call a spade a spade. Why would someone commit and eliminate options until they have to? This is why timelines can be helpful. Set a closing date and a deadline to get on board, then keep moving forward and execute.

Love and Money

In the crazy world of startups, VC fundraising is not for the faint of heart. Much like dating, it can be a rollercoaster ride of emotions, with exciting highs and gut-wrenching lows. So, as you start out to secure funding for your startup, remember this: love and money may be worlds apart, but the lessons learned from one can often be applied to the other. And who knows? With a little bit of luck and a whole lot of perseverance, you just might find your perfect match.

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