Founder-Investor First Meeting Dynamics, Pitching Preparation & Navigating The Conversation Framework - E317

Shiyan Koh, Managing Partner of Hustle Fund, and Jeremy Au dissect the intricate dynamics of initial founder-investor interactions. Here are the three main themes:

1. Initial Engagements & Decision-making Dynamics: Shiyan and Jeremy stress the value of the first meetings. For investors, it's a chance to see the viability of the partnership, gauging not just the business's potential but also the founder's vision and adaptability. For founders, it’s an opportunity to understand the investor's decision-making process. They share that both parties should have a set of clear expectations and an understanding of the next steps. They also see the first meeting as a helpful way to build trust, align visions, and ensure that both the founder and investor are on the same trajectory toward a potential long-term collaboration.

2. Technical Aspects of Pitching: They discuss the significance of the preparation for the pitch. Practicing their pitch, testing their tech setup, and even recording themselves to check for any issues can make a big difference. A smooth meeting exudes professionalism and respect for time.

3. Navigating the Conversation Framework: Jeremy and Shiyan talk about how conversations between investors and founders can focus on various topics such as the business model, its overarching strategy, specific industry or vertical, or even personal qualities of the founder and how it’s vital to know which "frame" the conversation is in. They point out that while various questions might arise, the underlying query remains as to whether the two parties are capable of collaborating over the next decade to build a successful company.

They also talk about pitching horror stories related to poor technical setups and how bad audio can ruin a good pitch, the art of striking a balance between high-level overviews and in-depth discussions during pitches, and the value of building rapport in the first meeting.

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Jeremy Au: (01:44)

Morning, Shiyan!

Shiyan Koh: (01:45)

Morning, Jeremy. How's it going?

Jeremy Au: (01:47)

Just had to consume my morning water, hydration, energy rituals, whatever you call them, so here I am. How about you, Shiyan?

Shiyan Koh: (01:54)

Is it like PM's magic water? You know, when you sip from the cup, suddenly you can become multilingual.

Jeremy Au: (02:00)

I wish it was true. I am primarily okay with English and I'm going to say conversational in Chinese. So no language switching is possible. Shiyan, I understand that today we wanted to talk a little bit about conversations about what you're seeing with founders and how to coach them. Could you share a little bit more about what you're thinking about?

Shiyan Koh: (02:16)

Yeah. I had a number of conversations the last week or so that made me think this could be a useful topic, and it really centers around how do you run a meeting when you're going into pitch. And I think there are many different components of the meeting, right? How do you open? How do you keep everyone on track? How do you close? But it might be useful to start with, what is each party trying to get out of the meeting. Because I think that context is useful for thinking about how the other person is behaving in the meeting. And mostly, I think.

It's the sort of mystique or mysteriousness of like why is this VC asking all these questions? I'm going to get to it later in the deck. Like why don't they just let me get to my slides? or you know, how do I get them on track when it doesn't seem like we're super aligned on what we're talking about? And oh, no, it's a 30-minute meeting and the clock is ticking down. And I feel like my chance to communicate what I want to communicate is slipping away.

So, we had just done a coaching session for our portfolio, and I played the entrepreneur, the hapless entrepreneur, and my partner, Elizabeth, played the annoying VC, and, she kind of like, jumped all over me and asked questions, didn't let me get through my slides.

I think the context is, as an investor, when you go into a pitch meeting, what you're trying to figure out is, do I want to spend more time on this opportunity? That's what you're trying to figure out. And so, if you have a 30-minute slot and it feels like the founder is taking too long with fluff slides up front, you just want to get your questions answered. So you just start asking them because, by the end of the meeting, you want to make a decision like, Hey, do I ask for more materials? Do I follow up? Or do you say like, Hey, thanks. Probably not for us. And so how do you think about this as a founder going into pitch? Which is like, how do I get that person the information they want? But how do I also communicate my story the way I want to communicate it?

Jeremy Au: (04:09)

Yeah.

Shiyan Koh: (04:10)

So, I think from a founder's perspective, thinking about you're not going to convince someone to invest in the first meeting. No, one's going to pull out their checkbook and be like, okay, I'm ready. So that's not your goal in the first meeting. Your goal in the first meeting is to get somebody to think, hey, this is pretty interesting. I want to dig in. And I want to spend more time learning about it. So how do you get them to that point? So if you know that's your explicit goal, how do you get them to that point? I'll pause there. Jeremy, agree? Disagree?

Jeremy Au: (04:33)

Yeah I think what I liked most especially was that point of view, which is I think investors thinking to themselves, whether they want to spend more time because at the end of this whole investment discussion and so forth, across multiple meetings. We believe that we're gonna make an effective team together and we're going to go out and try to build a unicorn or 100 million company together over the next 10 years, right? And that's a really difficult proposition. So I think the first meeting is so key, and I agree with you that a lot of founders really under-prepare for the importance of that first meeting in terms of being very clear, very direct, and also building the trust needed to kickstart the start of what could be a beautiful relationship or could the end of a one time call that doesn't really go anywhere.

Shiyan Koh: (05:15)

Exactly. So I guess we just start from that context which is like, do I want to spend more time digging into this opportunity? Am I intrigued? All this sort of stuff. There's a bunch of things that build up into that, so I think one is like, just the business. Do I understand this business? And I feel like it is shocking how many meetings I take where I have to repeatedly ask, who's the buyer? What's the problem? I feel like we should get to those up front. I should try to understand whose problem you're solving at the beginning. And when people say, " everyone", that's always very distressing for me because it's really expensive to serve everyone.

And so just having some sort of really concise snippet on like, hey, my customer is the CIO of a company that does at least 50 million in revenue and has 2000 employees or more. Then you're like, okay, I understand your segment. This is their problem. These are their current solution options. This is why it's not good. Here's why ours is better. Here's proof. That's why we can do this. You've said all of these things in under 60 seconds and you still have 29 more minutes. So I think you're trying to help somebody build up in their head a picture of what's going on. And you might say, oh, well, I already sent them my deck. How come they didn't read it? It's possible you already sent them their deck, but your deck wasn't made clear. So even as they had read it, or your deck was one of 100 decks they had read. And the meeting got scheduled 10 days ago and. They can't remember, right?

So I think you just need to think about your audience and how to get to those points. And so who am I selling to? How am I going to make money? Even if you don't make money now, what is my theory of making money? What are the unit economics of that? And what are the current things that you're really excited about or working well and, what are the sort of known risks you're going to work through? I think having a good balanced picture is useful, but I think an interesting point that you made, Jeremy, is talking about building rapport.

Jeremy Au: (07:03)

Yeah.

Shiyan Koh: (07:03)

How do you think about building rapport? in a first meeting?

Jeremy Au: (07:06)

I think the truth is that before the first meeting, you are who you are, right? You've been building your life experiences over 20, 30 years, 40 years, that timeline that you have you have been building this company idea for a year, two years. In the back of the head, you have some professional experience. You're bringing this into this. So I think you come in as who you are and that's okay. And I think rapport is a function of who you are as a person. That's one. Two is what your strategy is, and that's your actual approach. The third is like what you said, which is how you conduct the meeting in terms of the pitch and what materials you prepare.

And I think one thing I noticed in that conversation is that obviously if you have a great pitch, that implies that actually, you have a pretty good, great strategy, if that makes sense, which implies that you're a strong founder who is able to think through about what the counterparty wants, but also what the clarity or the hard trade-offs of their decisions would be as well.

So I think a good pitch is like a combination of three very intentional dynamics. The tricky part is that when the pitch doesn't go well, In other words, the rapport isn't built, the trust isn't built as a function of what you said, the meeting itself is not optimized, or is it the strategy is poor or needs further work, or is it that the founder themselves may not have found the market fit, or they may not be the right person, or they're not thinking clearly, or frankly, they're not a strong founder.

And so I think those are the interesting dynamics about what it takes to build rapport. For me, I often think to myself a little bit, which is, at least from my personal perspective if I'm having the first 30-minute meeting, I'm trying to optimize a bit less for the pitch deck itself. I'm really trying to understand who they are and what the strategy is, and I think I've had instances where honestly the pitch deck is poor, or the presentation is not very strong, but I would sit down and really think about it. It makes more sense to me because I'm listening to what a person is saying. And one thing I often find myself saying is something like, what you said is not what's on the deck, or it's not the storyline that you came prepared for. And I think you should go with what you're saying verbally in response to my question rather than the way that you think it should go and it's nothing to do with just a bunch of feedback. So I think trying to listen to where I find the most rapport is when I get the deep sense that the founder is a strong founder who understands the strategy or the trade-offs they have to make. They understand clearly who the customer is and so on and so forth. And then I can close one eye because at the early stage, you know, you're not necessarily going to have a strong deck always. So I think that's how I think building rapport is super important.

Shiyan Koh: (09:23)

Yeah. So I think that's true. The tighter your presentation is, the easier it is. But I was actually even thinking about super basic things up front, which are like if you're pitching on Zoom, I think people sometimes underestimate how much energy you need to show online relative to being in person. And so sometimes people come across as super flat and low energy, even though they're not necessarily that way in real life, and they might not even perceive themselves to be that way. And you might be like, why does this matter? And it's like, oh, I talked to this founder and he seemed weirdly unenthusiastic about his business and was really energy the whole meeting.

And so I think tactically. I think online, there's one thing, which is just, that you need to amp up your energy at the beginning and think about how that comes across. Also, I think there's just that sort of initial, 1, 2 minutes where you're doing intros and trying to connect with the other person where you, your body language how you lead into the conversation can all send sort of subconscious cues to the other person. So I think sometimes people look super tentative like they're very closed in on themselves. And they nervously are like, please refer to slide 1 and then they just click click, start going through it.

And I think that's something just to practice, like how to do that lead in and a more casual and natural way and set the other person at ease and be like, Hey, do you want to do this conversationally? Would you prefer to go through the deck? And you as the founder, I think you want to your preferences for whatever you're better at, whether you're good on your feet and you want to do it conversationally, or you prefer the structure of the slides. But then, you want your slides to be good and tight. I think all those things you want to think through in planning your fundraising meetings.

Jeremy Au: (11:01)

Yeah, I agree with you. I think a lot of folks obviously are nervous about fundraising and getting up time set up to pitch and so, so forth. It's important to get everything set up. So that Zoom meeting, the first 30-minute meeting that you had, I think you gave the time limit. It's very tight, obviously, but it's not a requirement to go through the whole deck if that makes sense, but really get the clarity around what the problem is, what the solution is why you can trust the founder, why you as a person, are trustworthy to run this approach. And I think some basics, for example, is that making sure that you're set up in an environment that you're comfortable with. A coffee shop, not running here and there, and yeah, if it turns out that it's the only time available, feel free to reschedule or find another time that you'd be comfortable with because you get one first meeting and then you never have a first meeting with that person ever again.

And so that first impression is so important. Humans are psychologically wired for first impressions. So it is what it is, and then making sure that you have good audio equipment, making sure that you have at least done some practice sessions and you've recorded yourself. How about what you look like? I think that's a good, important thing. Have someone just do some dry runs with somebody. Just say, let's record this thing. I'm going to pitch you and then, I think it can be another founder. It can be a friend. It can be a cofounder. It can be a teammate. But the goal is just for someone to have that thing, that 30-minute thing solved and that's so solvable because 30 minutes is actually, I don't know, to me, I think it's like an interview. It's, you can do anything in 30 minutes, you know, so, you can prepare for anything that's 30 minutes long.

What are some instances of pitches that you felt could have done better if it wasn't for something like technical or an avoidable mistake?

Shiyan Koh: (12:32)

Yeah, one that comes to mind is sometimes investors come in with some pre-knowledge, like they know something about the industry or they've had an investment or a failed investment in the space. And so they actually have a very specific view of the world that you live in, and they want those questions answered and they might open with those questions, which is like, hey, great to meet, blah, blah, blah. You know, I'm pretty familiar with this. The things that I'm most interested in are A, B, and C.

Jeremy Au: (12:58)

Yeah.

Shiyan Koh: (12:58)

And not answering the question directly, and then just trying to railroad the meeting down the slide format, I think can be very off-putting. Because it's wasting everyone's time, right? The person already said, I want to talk about these things, and you're like, huh, and then I went and did something else. So I think the meta point is listening to what that is and trying to like, you can answer it in a short way, say like, hey, here's the quick answer. And I actually have slides that address this point in more detail. At least answer the question 1st, before you try to get into the detailed thing. And so I think listening is a key thing that helps you to avoid being derailed.

And then I think the other thing is when you're thinking about what the other person wants is, you're basically trying to get them to align on a few key assumptions of your business. And if you aren't aligned on the key assumptions, you're not going to have a good conversation. So those slides where it's like, " and it's trillions of dollars. And I've projected all of these things that are going to happen." Okay, great, but not that useful because your projections are a work of fiction generally in the early stage, and it doesn't really matter. What is the heart of, like, do we believe this problem exists? Yes or no? Do we believe this is a big problem? Do we believe that people will pay for this problem? Do we believe that you can make the product that fixes this problem? Those are the things you're trying to figure out, right? And every industry has specific quirks to it, like, oh, this industry is incredibly fragmented, and here are the challenges that other people have faced in this space, or, these people are incredibly sticky for some weird structural reason, and here's why people so like, how do you plan to solve those things? That's where you want to focus the conversation on. You need to sort of tease out what the other person is thinking about your assumptions so that you can drive the conversation in a more fruitful way. And if they don't say anything at all, I think you want to try to elicit some response because then, you don't really know what they're thinking. And so that's where the sort of conversational aspect comes in, which is like, here's what we're seeing. This might relate to a company in your portfolio in this way, blah, blah, blah. It also shows that you've done research on their portfolio and, their investment preferences, things like that. I think you want to think about it less as a one-sided broadcast and more as a way to figure out if this person is going to be a good potential partner for me because we are aligned on the opportunity and the assumptions.

Jeremy Au: (15:12)

Yeah, I think it goes back to the part about, do we trust each other to have a deep strategic question about the underlying business model approach of the company? And I think it happens because founders get too sticky to the format. don't think it's over-rehearsed, but they're fragile in the sense that they have a certain narrative of how the meeting should go versus what the meeting is going right now, right? And I think that's a very important moment of discussion. And like I said, 30 minutes, it's very solvable. It's very preparable. And the questions that the investors are going to ask, even if they already know the space from before, it's going to be pretty straightforward. Just Hey, I believe that the margin just space is very difficult. For example, how do you think about maintaining and building margins and having a profitable business in the space? That's going to be a no-brainer question that hopefully you think about. How do you come across as somebody who's a mature person? Who's understanding the space, but also aware of what experiments and learnings needed to be done in order for you to succeed? mean, it could be a wonderful moment of truth for both sides, I think one interesting conversation I often have, and sometimes I end the 30-minute conversation is like, Hey, this is how I would improve the pitch. But the more important question is, these are the questions that we have about the business. You have a business and I have about a business.

So the question then becomes like, how do we prove, not necessarily who is right, although it can seem like that, but what is right? What is the right path? What's the right assumption? And I think that's also a good way to wrap up the 30 minutes is kind of saying like, hey, Jeremy, I understand that you think that margins are, let's say, difficult in this space. And you're skeptical about it because of past failures in the space who haven't been able to do it with this approach. What I'll do is, why don't we discuss this? For example, let me circle back with you. And let me talk to you about how I think margins can improve over the next six months and then let's discuss further about it. But I think wrapping up that meeting with a strong sense that it's okay to have questions. It's okay for the VC to have questions, outstanding questions because you can't solve questions in 30 minutes, but neither can the founder finish them as well. So how do we keep that next step going is actually a key way to tie off the 30 minutes as well.

Shiyan Koh: (17:07)

I think that's right. The other thing is also, I think from a founder's perspective, you want to get clarity on the investor's process. And so make sure that you ask the question at the end, which is, like Jeremy said, Hey, it sounds like here are your outstanding questions. Here's my follow-up item. And then my question to you is like, what's your process? What are the next steps? How do you guys get to a decision? And what other information might you need from my side? So that you have a really concrete set of follow-ups once you get off the call.

Jeremy Au: (17:30)

Yeah. Yeah.

Shiyan Koh: (17:31)

Any horror from your side, Jeremy?

Jeremy Au: (17:34)

Yeah. I think the horror story on my end would just be a bad audio setup. It's just such a preventable error and it's such a shame. But you know, if you have a fan in the background and you have a lot of people running around the background, sometimes it's not avoidable, but I think if you take a giant step back here you're trying to make a first impression on somebody. And so you want to make sure that you can control the environment as much as possible. So, you can be the world's best pitcher, but if the other person can't really hear you and it's too distracting in the background about what's going on, then unfortunately, someone who's intelligible in the conversations, that's going to have a better shot, right? I think that's really important to really invest in, just a computer and the audio equipment.

Shiyan Koh: (18:14)

A computer.

Jeremy Au: (18:15)

And I don't, I mean, I've seen you know, people whose computer just couldn't really run. Again, I'm just saying like, that it can be a problem because, an example I think I saw, like a classic one would be I have a new browser, I have a Zoom, oh, I can't get my screen capture to work, I can't present my slides and be sent five minutes. you know, Watching you figure out and share your slides. And I'm just like, I did such a shame, honestly, because the time is precious. So, understandable when it happens, but I think we should try to minimize it. And that's where practice, like you said, really helps. Uh, Any last words of advice from your perspective?

Shiyan Koh: (18:48)

No, I think we covered it which is just like, think about what you're trying to achieve and think about what the other person's trying to achieve in the meeting and tailor your remarks to address those needs and practice. Because I think sometimes when you are too heads down, you kind of forget that what you think is really obvious about your business might not be so obvious to another person. And so it's finding the right level to have the conversation. Not too high level and not too weedy, but sort of striking that balance between like, hey, here's the core assumptions about why this is an amazing opportunity. And then there's like the deep dive into all the great work that we've done and why we think we have a glorious future ahead.

Jeremy Au: (19:22)

Yeah. On my end, my parting word of advice is to practice and record yourself because I think there's often a lot of practice that you're making ahead, but I remember that when I was a founder at fundraising, I think the difference between, somebody would put a camcorder back in the day and just be like, record me pitching. And it was a big struggle because then you start seeing your own, I don't know, body language, my eyebrow twitching. It's a very discouraging experience because I was like charming and presenting my points and then you watch yourself, you're like, beep, beep, boop, like clown thing that you're doing. And I think that gap is something that you had to close as much as possible. Again, nobody's expecting you to be like a super person in presenting your pitch, but there are so many things that are a lot more obvious when you put that person's eye on yourself, which can be very difficult to process.

On that note, I'd love to summarize the three big takeaways I got from this conversation. First thanks so much for sharing your perspective on the first meetings and how it's really important from the investor's perspective to make a decision about whether to keep going and keep investigating and exploring whether to work together as a team. And so it's really important to be thoughtful about how the founders should be structuring their time.

Secondly, thanks so much for sharing the technical point of view, which is how founders should prepare in terms of practice and recording ourselves, and making sure that there's a strong sense of understanding of what the investor may ask or could potentially ask.

And lastly, I think we discussed very much about what the different frames are. Are we talking about the business? Are we talking about a strategy? Are we talking about the vertical? Are we talking about you as a founder? So I think there are many different types of questions that can get asked, but at the end of the day, it's like, are we going to work well together, and should we spend a lot of time together in the next 10 years to build a lot of company together? On that note, thanks so much. All right. See you, Shiyan!