Running a startup fundraising campaign in 2023

So you’ve decided you want to go find some equity investors for your startup? Excellent! Be aware that it will take you longer than you think, and it will be hard on your ego because you will experience a lot of rejection, so it’s important to use a structured process and approach it with intention. Let me give you my top ten tips for hitting the equity fundraising trail:

It’s a numbers game.

I recently had a call with a founder who told me he’d just closed a nice round of capital. Over the past year, he had more than one hundred investor conversations. Of those, forty-two requested more information, twenty-three requested a third meeting, eleven submitted the deal to the partnership for an investment decision, four issued term sheets, and two invested. These numbers are actually pretty decent. 

Play the long game.

The same founder also said that he kept investors engaged for many months—even those who had said “no.” Over the year, he sent out quarterly updates to every investor he talked to, circled back with them about concerns they had expressed, and kept them informed as milestones were achieved. Raising capital is a sales process, and the sell cycle can be long. You’re not going to pitch on Tuesday and have a term sheet on Wednesday. Play the long game, and you will succeed.

Don’t visit devils if you’re looking for angels. 

Angel investors will invest at the idea stage; VCs typically will not. I’ve seen founders waste a lot of time pitching to the wrong people. Research the right investors and funds beforehand. 

Solid economics are more important than ever.

Remove from your brain the mythology that investors will drop cash into crazy-ass ideas with no clear monetization. Investors today want to see opportunities where the founders have already proven the economic model and it’s ready to scale. It all comes down to CAC < LTV, baby (see Chapter 5). You may not have actual data yet, but you need to have a compelling story about how the economics will come together. 

Cold calls aren’t efficient. 

Every investor I’ve ever had in my career was either someone I knew socially or referred to me by someone I knew socially. Most VCs I know say they’ve never invested in a deal that came in over the transom. Focus your energy on getting warm introductions, and you will be 100x more effective in your fundraising efforts. Sending out cold emails is lazy and ineffective. Building relationships is difficult and takes longer but is far more effective. 

Ask for introductions. 

Here’s a secret hack: Let’s say you hear of an investor you think would be a perfect match for your startup, but you don’t know them and would like an introduction. Find out what other startups they have invested in (use Crunchbase or PitchBook), and then reach out to one of the founders and see if they’d be willing to have a call just to get input on your startup idea. At the end of the call, assuming they seem friendly enough, ask whether they’d be willing to make an introduction. The point is that, as I mentioned, warm introductions will always be more effective than cold calls, so find ways to get them. 

Ask for advice (get money). 

There’s an old expression: “If you want advice, ask for money. If you want money, ask for advice,” and this maps pretty well to my own experience. When you pitch an investor for money, they are likely to say, “No,” but then give you a whole lot of unsolicited advice that may or may not be helpful. Conversely, if you flatter an investor by asking whether they’d be willing to have a call with you so you can get their sage advice, they may well end the call by saying, “I like this thing you’re working on; are you looking for investors right now?” Human nature is what it is.

Don’t look for peaches in the berry store.

Don’t pitch your early-stage SaaS startup to a growth-stage biotech investor. Every investor has a stage and sector focus. If you have a social venture, focus on impact funds, not traditional venture funds. If you have a digital health startup, find investors who focus on that niche. Taking the time to understand an investor’s stage and sector focus will make your fundraising much more effective.

Double down on storytelling skills.

Every great entrepreneur has the ability to tell a crisp, clear, and compelling story about what they’re working on and why it matters. It The more you pitch, the better you get. The more you pitch, the more you learn. The more you pitch, the more opportunities you have to get a referral. It has always been thus (see Chapter 8).

It’s a sales process. Use sales tools.

The fundraising trail is like any other sales process, so utilize the great sales tools available to you. Use customer relationship management (CRM) software for tracking every touchpoint, consider upgrading to LinkedIn Sales Navigator for research, use DocSend when you send out your deck and then HubSpot for sending out updates and tracking opens. Treat your fundraising like a professional sales process—because that’s exactly what it is. 

You are going to hear a lot of no’s, and you need to refrain from taking them personally.  Startup investors want a diversified portfolio, so they may say, “No,” just because they already have a SaaS startup in their portfolio and now they are looking for an AI chatbot. Or a thousand other reasons, so don’t ever take it personally. 

As I was writing this chapter, I reached out to my friend Gleb who recently completed a successful seed-stage fundraising effort. I asked him what advice he would give new founders. He responded: “There’s only one answer: do the damn work. Research plus execution equals success. There are no shortcuts, unfortunately.  Increase the number of shots on goal to maximize opportunity.” Be like Gleb. 

Conventional wisdom once dictated that you should set a minimum investment threshold for seed-stage fundraising from angel investors. For example, you might say, “We’re raising a six-hundred-thousand-dollar round, and we’re looking for investors who would like to join with a minimum of fifty thousand dollars.” Today, however, seed financing rounds are typically done with SAFEs, so transaction costs are low—an investor sends you the money, and you just send them back a SAFE. This means that there’s really no reason to set a minimum. In fact, there are lots of upsides to having a bunch of excited investors at any monetary level. So, if someone is really excited about investing, and they want to put in five thousand dollars, take it. You never know who they might introduce you to. 

Running a startup fundraising process requires dedication and intention, and it will probably consume more of your time than you expect. Treat it like any other sales process: make sure you have the right tools, are pitching the right people, remain diligent in your follow-ups, and track every touchpoint. Play the long game, and build strong relationships. If you do that, you will succeed.