A startup founder wears many hats: Leader, ambassador, visionary — and, of course, fundraiser. But Robbie Crabtree’s company Founder Fundraising coaches founders as they don one more: “Chief Storytelling Officer.”

Robbie, a serial entrepreneur and former litigator, sees the fundraising process as akin to a courtroom trial.

A prosecutor’s opening statement is a concise introduction to the case, similar to a founder’s first call with an investor. An attorney’s closing argument “pitches” to 12 jurors like one might pitch a deal to all the partners at a VC firm. The average trial lasts one or two weeks — which mirrors the typical timeline when persuading investors to fund a startup. 

But to pitch well requires understanding the different stages of fundraising and what each step entails, Robbie says.  

“You have to understand the rules of the game,” he adds. “Because you deal with investors differently before the first meeting ... at the first meeting ... in between the first and second meeting, at the second meeting — it's very similar to a sales process.”

All hands on deck: Pre-meeting pointers

Like a resume and cover letter, your deck should be tweaked and tailored to the opportunity. Sometimes it’s even worth developing multiple decks for a single pitch, each designed for different purposes. 

In addition to your core pitch deck, consider a text-heavy “explainer” version to use as a follow-up tool. Often, investors pitch to their partners, so they need to be able to clearly articulate your value proposition on your behalf. Your role as a founder is to “equip them with the information to be your champions; to get to that next meeting,” says Robbie. “Sometimes we've got to take information, put it in a nice, concise way, and let them do the storytelling.”

Meetings, from first impressions to term sheets

Robbie considers the first meeting with an investor to be about “building connections and having conversations,” not asking for money immediately. Initial meetings should create rapport; if that happens, “your chances for a second meeting go way up,” he says. 

Focusing on money at the outset “creates this transactional, cold relationship dynamic, and humans just don't operate that way,” Robbie adds. 

A few more first VC meeting musts:

👉 Chat about your mutual connection 

You probably already have something in common with the VC you’re meeting — you both know the person who introduced you. Start there: Ask how they know your mutual acquaintance and make sure you reinforce the fact that your warm intro came from a trusted source; therefore, a level of trust already exists.

👉 Get curious and learn their story

Storytellers don’t just share their own narratives; they also listen to others. Ask investors to tell you their stories. 

“It creates a sense of reciprocity,” Robbie notes. 

People love to talk about themselves. If you give an investor a chance to tell you how they came to be in their current role and about their accomplishments, you put them in a good mood. It also helps them “feel like a normal human instead of just a source of capital,” says Robbie. 

👉 Pop some questions 

Meetings with investors aren’t just occasions for presentations. They’re opportunities for dialogue. 

“Tell your founder story, tell your vision story, and then have some questions,” Robbie says. “You can go back and forth.” It’s a conversation, not an audition. 

👉 Understand the investor’s process

Every firm is different. In some firms, it takes unanimous consent. In others, one person can lead the deal. 

Use those earlier meetings to learn the specific VC firm’s process. When you understand their process, you can build your strategy accordingly. For example, you might know that even if one decision-maker dislikes you, it won't sabotage the deal. Or you might know that if one doesn't like you, it’s a problem. If that happens, Robbie suggests reaching out to your champion — the person who can provide backup and guidance.

👉 Ask for a second round

Don’t assume (or expect) investors to ask you for a second meeting. “You have to ask the question,” Robbie advises. Say something like: Hey, it feels like there's some alignment here. I've really enjoyed this conversation. Would it make sense to go ahead and set up a second call so we can dive deeper to see if it's a good fit?

Of course, the three possible answers are yes, maybe, and (unfortunately) no. 

“There's a decision tree based on all those ... but founders have to be willing to ask,” says Robbie. “Many of them get to the end of a first meeting or first call and finish with Okay, well, this was great. Well, you'll just let me know.”

If you don’t broach the subject before leaving the room, it’s a missed opportunity “because investors want less friction,” Robbie points out. “You have to ask them: What are the next steps? How do we move this forward?”

Best-case scenario: The investor is happy to meet again. More likely, they’ll tell you something like, We'll talk it over internally and get back to you. And sometimes, you’ll just get a “no,” but at least you have your answer. This strategy leads to a “ridiculously high increase in conversion to a second meeting — just by asking that question and doing it in a non-pushy way,” Robbie notes. 

👉 Handle any answer with aplomb

Rejection happens for numerous reasons — many of which are simply circumstantial. But you can make lemonade from lemons by leveraging your meetings to grow your network. 

Robbie’s script in reply to a “no”?

I appreciate that. We know we're not for everyone. It seems like we had a good conversation. I would love to just stay in touch. And if there's anyone you think would be interested in this, I would love for you to introduce us. If not, no worries.

👉 Put it on the calendar

What about a “yes”? Well, congratulations! As soon as you hear that magic word, nail down the next meeting: Offer a variety of days and times right then and there. If they say Yes, but I need to check in with my team, you can take one of two routes. Say, Hey, would it make sense to just set a call on our calendar? We can always change it if it doesn't work for your team. Or reply with something like: That makes total sense. When should I expect to hear from you? 

Sometimes investors drag their feet. Sometime next week isn’t much help. Persist in drawing out and/or clarifying their answer if need be: If I don't hear from you by Monday, I'll reach out with some times on my end. Or ask, If I don't hear from you by Wednesday, can I assume it's not a good fit? 

You're not forcing their hand, but you’re putting a bit of gentle pressure on them. That’s the only way to ensure clear next steps and expectations — and preserve your mental health.

The “maybe” is the toughest answer to deal with. But Robbie recommends an approach similar to that last one: OK, that makes total sense. I know you have a process and you need to discuss it with other people. When should I expect to hear whether you want to move forward?

The second meeting

Round two is where your interactions with VCs dip into make-it or break-it mode. 

When new people arrive in the room, finding out what they already know (or don’t know) is essential. 

“We don't want to assume anything,” he says. He suggests asking a new contact (who works with the investor you’ve already met) something like: I want to make sure we have a productive meeting. I know John and Robert. But I'm curious what Robert already told you about myself as a founder and what we're building here at Founder Fundraising.  

That way, you can learn how familiar they are before you proceed with the conversation. Perhaps you won’t need to share your company’s vision story, but you should share your founder story — or vice versa. Then you ask them for a short version of their story and tell them you’re happy to answer any questions. 

Essentially, these tips focus on “maintaining proper meeting dynamics,” says Robbie. “[You’re] gathering information, yet leading the conversation and allowing the investor to feel like they're in control of the conversation, so it's not one-sided.” 

In a second meeting, founders should be ready to answer any questions, including the toughest ones.

“You have to be prepared. You should understand what your positioning is and what your framing is ... You should know your numbers really well, especially financial numbers like your CAC and LTV. You should certainly know your go-to-market and [other] strategies.”

Your answers should be short and sweet. A rambling reply suggests you’re not a hands-on leader. 

“This is your moment to shine, to show you came prepared to deliver, that you know yourself,” Robbie adds. “When you're asked questions, pause before answering them. Give yourself two or three seconds to think them through ... and deliver them in a confident but approachable manner. I call it ‘approachable expertise’: I know I'm the expert, but I invite your conversation and questions. 

Three (or four or more) time’s a charm?

By the third or fourth meeting with an investor, you might walk into a room with 10 other people, including all of the VC firm’s partners. It’s inevitably stressful because it’s difficult to be conversational with an audience glaring at you. 

Preparation is poise. Composure is confidence in knowing your stuff. A good founder should internalize all the answers to investors’ questions “because they're the real answers,” says Robbie. “We're not making up false answers. We're just packaging what's there in the most compelling and clear way.”

The tactics Robbie shares here can help you put your best face forward. But there’s an even more fundamental strategy you can put in place: 

“I just had a client close a seed round,” he says. “The biggest change we implemented was not the story. It was not the process. It was actually mindset and how that founder was feeling about it ... mindset creates energy ... it allows an investor to feel that a founder has that it factor.”

Operating from a scarcity mindset is operating in fear, Robbie adds. 

“We want to be operating from a place of confidence and abundance — that there's plenty of money out there; there are plenty of investors ... that we're building a huge business and people want to be involved. That attracts the same energy back to us.” 

For more of Robbie’s tips on meetings with investors, check out this recent article.