How to Capture an Investor's Attention with Rebecca Kaden

INTRODUCTION: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Rebecca Kaden. Rebecca is a partner at Union Square Ventures in New York. Rebecca, it's great to see you here.

Rebecca Kaden: Thank you so much for having me.

Matt Blumberg: So my question to you is, I think probably true of any venture firm, but certainly top tier firms like USV. You all must get thousands upon thousands upon thousands of business plans.

Rebecca Kaden: Yes.

Matt Blumberg: Or whatever form those take. I realize no one does a business plan anymore, but thousands of inbound, unsolicited, Hey, here's what I'm doing. Here's my teaser, here's the deck, here's my PDF, and if only you would listen to me talk for a little bit and hear my pitch, you would of course fall in love with my company and want to invest in it. So my question to you is how do you narrow that list, the infinite list down? So what are the few kind of best ways that founders get your attention?

Rebecca Kaden: Yep. It's a question we think about a lot because as you mentioned, the volume is really large and our goal is to sift through that noise and try to narrow it to the best alignment for what we are focused on. And for our thesis, which doesn't necessarily even mean the best companies, it really means the best alignment for us. And I think about that when I look at these. So the three things I would point to on how we sift through the inbound to figure out our focus is... And the advice I would give to stand out in that noise is first, this may sound obvious, but it's actually the most important. Lead with what you are actually doing. You would be surprised at the number of emails and decks that share a lot of information and background and context. And it is very hard to figure out what is the company, what is the problem that they're solving and what are they building? And if I can't get that very, very quickly, it's the easiest thing to move on. So in a very concise way, what are you building and why are you building it?

Matt Blumberg: Okay.

Rebecca Kaden: That is definitely number one. Sounds obvious, but matters a lot. The second one is, as quickly as possible, get specific on why it's a fit for the specific firm that you are targeting. There's a lot of information out there about firms, USV and others these days. The stage we focus on, the sectors we focus on. For USV, there's actually even more information. The theses we focus on, we try really hard to be very public about what we are looking for. And as a founder, you can help connect the dots and say, here is what I know you're interested in. Here is why what I'm working on is a good fit for that. That really helps to stand out. And simultaneously, if as you're reading about firms, USV or otherwise, you realize, hey, this firm has never invested in something like me before. Either this stage, this sector, this category, it's unlikely that they're going to break the rule right now. Obviously crazy things happen, but it's an anomaly. And as a founder, I think a lot about, your goal is your time and to really protect your time, that's a huge asset. And so spend your time on the firms and the people that have the most alignment. And there's a lot of public information to find that. So I would start there and then make it clear to the person you're targeting why there's alignment.

Matt Blumberg: Let me ask a quick follow up before you get to your third one. Matter by partner or just for the firm? I know at USV, Albert does climate stuff and you and Nick do some crypto stuff.

Rebecca Kaden: So it really depends on the firm. At USV, I would say, actually the vast minority of companies that come in, wind up being led by the partner they came into. We have a quite a good system on passing things around. I'll see something and I'll say, Hey, I actually know Nick's really pulling that thread right now, or Andy's been interested in that at this moment, and I'll just pass it along and we'll pretty quickly get it to the right person. We're also all generalists. So in truth, actually, we've all led climate investments, healthcare, fintech, education, marketplaces, and we do that very purposefully. So USV, it doesn't matter really that much who you come to. Certain firms, it matters a lot, right? They operate in a much more siloed way. That's just how the firm works. And so you really want to make sure you're getting to the right person. I kind of mean that on two regards. One is as a category and a stage, and the second is as a decision maker. You've raised a bunch of money, you know this. Target the people that can make decisions at a firm.

Matt Blumberg: So lead with what you're doing. Make sure that you are finding the firm with the right fit and explaining how you feel like you fit and what's your number three?

Rebecca Kaden: So the third is, all else being equal, think about the pathway in. Cold email, there are examples in the USV portfolio and others of fantastic cold emails that have resulted in great investments. But as we started by, there's a lot of noise in that funnel. And if you can stand out, if it's an option, think about who is that intro and how to get in front of the people that you want to get in front of. And I think about the hierarchy there. The number one goal is do you know any founder in their portfolio or someone that may work at one of the companies in their portfolio. The second is other operators, other founders that might know the firm. The third might be other investors, you know, can work down the list. If not, cold email is totally viable. We know that it happens, but stack the deck in your favor if you can figure out a way to do so.

Matt Blumberg: So quick follow up on that before we wrap up. How do you all think about bias in the selection process as it relates to that? Because it may be that some of the cold emails are people who don't have network.

Rebecca Kaden: Yep. It's super important. Yeah. Look, I think that's important for us to be heavily aware of it, and we are. And we work on lots of systems to make sure that the deal flow coming in and the companies we're seeing reflect outside of our existing network and we try to be very conscious about it. At the same time, do we pay attention to founders in our portfolio sending us investments? We just do. And so I always like founders, or potential founders, to be aware of everything they could do to stack the deck in their favor and to play the right cards while really we take responsibility and believe we need to be very cognizant to make sure we're as network- expanding as possible.

Matt Blumberg: All right. Three great tips for founders on how to reach your VC of choice. Rebecca Kaden from Union Square Ventures, thanks for being here.

Rebecca Kaden: Thank you.