Tigress Ventures hosted a monthly speakers series featuring thought leaders and industry experts, and provided private consultations with individual clients.

Ita also served as Venture Partner at Plum Alley Investments, where she oversaw investment opportunities and pipeline for high-growth female-founded and gender-diverse startups.

Previously, Ita held product management roles at TravelClick and American Express. She began her career at Goldman Sachs as an analyst in Credit Capital Markets and then as an institutional trader of preferred stock. Ita holds an MBA in Marketing and Entrepreneurial Management from The Wharton School, University of Pennsylvania; and earned a Bachelor’s degree in Psychology, with a certificate in Finance, from Princeton University.

What is GingerBread Capital?
Our mission at GingerBread - we are a venture firm carved out of their family office, the Roberts family office, and our mission is to invest in that next generation of women entrepreneurs that are building high growth, venture-backable businesses. And one of the things that we do is that we are making sure that you need the capital, and then you need access to those networks and the other people that help you advance your business along. From our standpoint, we're not leading rounds, right? So we are not going to be leading a round. But we are going to be the one where we get a lot of calls where people are like, "we'd like to collaborate with your team," because we bring that to the table of access to networks, and access to our cells as well.

We're all former bankers and operators on the team and we're happy to give that without having to necessarily have a board seat to the companies that we invest in. That's what we're bringing to the table. And we're also wanting other women to be investing in women. So this asset class of the private equity world in general, venture capital in particular, has been dominated by men, as we all know, both from the sides of who's deploying the capital and who's receiving it. And that's one of the things, as capital is moving over from men to women and the transition over these next few years, we want women to know that they should also be having access. And thinking about when they get disposable income that gives them that optionality, to consider investing in female founders, whether directly in companies or if they don't have the time to do that all the time, through funds as well.

So that's the team Linnea started. Katherine, another fellow Partner, Olivia, Principal, we are the four investing members of the Investment Committee, and then we've got our Executive in Residence, Cary, and the woman that makes us all sound wonderful, Jeanie Barnett. So that is Team GBC. One of the interesting notes about GBC, we were always a virtual company. I'm based in New York. Olivia is now temporarily sort of here in New York as well. But mostly everybody else was in the Bay Area, and even pre-COVID, we were a remote team. So it's kind of like the rest of the world works the way we do.

Who do we invest in?

We have CPG companies like Goodles - if you're a mac and cheese fan and you want to better tasting mac and cheese, I highly recommend it. I was converted. It's delicious. Everything to content management and content stack, and then healthcare in between. What we are trying to say in our thesis is that you can't pigeonhole what women are doing. Women are innovating in great ways across the spectrum. And that's reflected in our portfolio.

And in the state of 2022, I saw this recently. It was a piece put out by Christoph Janz at Point Nine talking about the state of SaaS funding in 2022. Every year, they kind of put out this napkin of SaaS funding. And this is particular to SaaS funding, but you can extrapolate some of these learnings if you're doing a consumer CPG, or product. He talks through and they looked at the beginning of 2022 when it was still a little bit frothy, up through to around the end of July when the markets really started quieting down and shutting down, and how the bar has changed. The bar of what it takes to raise pre-seed, seed, series A, and series B has shifted from the standpoint of valuations have come down. Not so much as the pre-seed stage, when you're looking at SaaS companies, they were still in that range of 3 to 12 million , but definitely things that you were seeing from some of these series A or series B, where they were things like 500x revenue, were getting these valuations. So those days for the moment are done. And I was laughing with Dee before because women were not getting those kinds of crazy valuations to begin with.

What are investors considering in 2022 and beyond?

But in this moment, as investors across the board have batten down the hatches, it has gotten that much harder. And the key thing is being able to tell a compelling story of why you're standing out in this market, and then traction now more than ever matters a lot. So that ability to tell a crisp story and show traction is the key to really getting from that seed to the A stage, where you're going from your first 0 to 1 million at that seed stage to at least getting towards the million, almost towards like 3 million, is the new standard of wanting to be seen for that series A check. And the valuations anywhere between that 25 to 75 million in round sizes between 6 to 18.

So the check sizes are coming down, the valuations are coming down. But the expectations of what people want to see, and the time horizon that it takes, has gone up. And I think female founders have always been sharp on this, so I don't think that this is going to be any news to you guys.

But it's now more important than ever to be able to tell a crisp and compelling story. That's part of what we're going to talk about here is what is it in that story that I want to see when I'm looking at these pitches, because series A is the sweet spot that we like to look at, and what is it that needs to come across so that you stand out and can get the second meeting. Because the key - nobody gets funded on a single conversation. Maybe some people in 2021 actually did.

But these days, you're going to want to wet the person's appetite, so they say, "I want to take another meeting", and keep it going from there. And that key is storytelling, which I'm sure the majority of you guys know that. It's really honing it into being able to tell it from anywhere as short as 90 seconds, if you're just getting that dream investor in a room, to thinking about how you can take that and extrapolate it. But the elements of that are always the same.

So we're going to talk through what are the elements of that perfect pitch. There's never a perfect pitch, but you can get it pretty darn good. But these are the things that we want to see. So when you're thinking about that, it's the compelling backstory. It's the differentiated business model. It's the competitive landscape, scalability, and in my opinion, I always add this, it's the audience. One pitch does not fit for every single event, from investor to investor, and from investor to customer. You must know that you need to target and customize your pitch to fit the audience that you're talking to.

What makes a perfect pitch?

What makes the company stand out? What makes the company stand out when I'm looking at it? That compelling backstory. Everybody tells you this - if you're trying to raise money from somebody, what is that problem you're solving, and how big is the problem. If you are trying to raise venture capital, you need the big problem, the opportunity, to be really big. You need that total addressable market to be large. It has to have like a billion in front of it and larger to get the interest of a venture capital firm that would want to take a look. And that doesn't mean that that's the only way. And I want to be clear that you can use this to raise money from other sources, but if you're trying to go raise from venture capital, you need the problem and the opportunity that you're trying to solve to be really, really big. And then I always like to know what is making you uniquely qualified to tackle this problem. Did you just wake up and be like, "I want to do this today," or what we tend to see in our portfolio companies and our founders, is that they were either working in a field or hit some stumbling block and were just like, "This doesn't make sense, and I know how to do this, and I want to dedicate the time to try to make this better, faster, cheaper."

And so there's usually a reason that makes you uniquely qualified.

And I personally find it really compelling to understand why because it's going to tell me why you're going to stick with it when it's going to get difficult. Because inevitably it will, and do I feel like you are going to be the kind of founder that's going to stick with it throughout the course of this lonely journey that is being an entrepreneur.

Don't forget the business model.

And then of course, we need to understand your business model. So how is your company solving that problem, right? Hopefully, you're doing something that's, like everybody says, never been done before. But, you know, what is it that you're actually bringing to the market? And have you brought to the market? How much does it cost? How much is it costing you to make your product? More than ever these days, everybody's looking at the unit economics of companies and trying to make sure, is this one of these things that if at scale, you really will eventually become profitable? Or if your business isn't, like it could be unprofitable at the beginning because most are, but if as you think about it at scale, that moment never happens, you need to rethink your business model. In today's landscape of investing, everybody's looking at that part of, what is that moment that will make this company truly turn profitable at scale to break into those markets? And then part of that is, how long do you retain your customers? Is your product, something that people only use one-off? So you'll need to always constantly be acquiring a ton of people? Or is there a stickiness factor that keeps your customers coming back? And how long do you get to keep them? So the more you have people, especially in a SaaS model, where they're willing to pay you a subscription fee and you lock them into a year at a time using your product. Or if it's in the consumer space, and in a CPG product that people have a desire to use a lot and consume a lot of, that's the kind of thing that takes note in terms of the business model.

Never send a pitch without a competitive landscape.

People be like, "Oh I have no competition!" Somebody was doing something before you showed up, obviously, it was happening. So there is some kind of competition, even if it's just pen and paper, where some people are disrupting things that had been done manually and bringing it out digitally. Never do a competitive landscape where you're like, "There is no competition." That just shows that you haven't dug hard enough, and maybe you haven't understood the competition in your space, and you aren't quite seeing how you're differentiating, which is really important. When you can say, "Well, people have been doing this, this, and this, and when you when you do those grids, or like the slides across that show the circle full half quarter type thing, and you can show here's people have been doing and using and here's how we're different and how we meet all the needs and beyond in the landscape. That to me is one and Linnea. Always, if you're on a call with Linnea, if you don't ask it, she's going to ask it, what's the competitive landscape? So it's really important that you have that well mapped out.

And then thinking about that to that point, how are you going to win against them?

What are the proprietary intellectual property or strategies that are going to give you the moat that will keep you ahead of your competition? Is it that you're first to market in a new way, and then by the time others can catch up, you'll already own a bigger share of the pie than everybody else? Or do you have patents or things they can actually keep people or you can block people who do try to enter into the space? Competitive landscape is really key. And especially in this market, where it's tougher across consumer things with the iOS changing.

How are you standing out and trying to be seen?

And so that leads into your scalability. I need to understand how you go from your beta, with doing it with your friends and family, to really starting to scale beyond that. What is that go to market strategy? How are you planning and staging to do it? And what are the milestones that you're trying to get? Because, part of these decks, people will look at them over time, right? We'll see, what did you say you were going to do? And the next time you come back, you're going to be judged on, did you do what you were going to do? We know that 100% of the things won't happen because you know, life and things happen, but it sets the tone of how you think and how you execute if you are able to think about and talk about a go to market strategy, and then in a follow up, follow through on what you were trying to do. So part of that go to market is that cost of customer acquisition. Anybody that's doing a consumer product knows that when Apple changed the iOS things, it killed the whole Facebook game, the whole Instagram game, for a lot of people. So you had to start thinking more creatively, or a lot of people started paying up more, but they weren't seeing the same results that they saw before. In the last year or so, you've had to try to become more creative in how you're acquiring your customers without having your marketing budgets explode and spending all your money chasing people that you're not even sure you're getting. It's good to understand what are the key performance metrics in your product, in your service, in your industry. Benchmarking yourself against the competition and knowing what success looks like is important, because the more you can talk about that, the more it seems like, "oh this person is on top of it, they know what it takes to succeed in what they're doing. They're not trying to shy away from it, or like fudge it and punch it down the line."

When it's earlier days, it's the ideation phase, the beginning, you're not going to be hitting these numbers out of the park. But when you know you've got product market fit, that's when you start seeing the repeatability of some of these things and seeing those numbers start really gelling, that's when you know that you're onto something that's a potentially big idea. And I think it's always important to, whether it's in the beginning, talk about what the milestones you're trying to achieve. Or by the series A standpoint, you should be able to talk about, and you should have key milestones that you've hit that say, "I have gotten to this point with this next round of funding that gets me to put the fuel on the fire. I can take this business to the next level." If you don't have some significant milestones as you go from that seed to the A, you need to consider is this the right time to be fundraising or not? Have I actually hit the product market fit? Because with the series A and going forward, it's about saying, "Okay, I know what works, and now with more capital, so I can go more aggressively acquire customers or build out the additional functionality that customers are already wanting, I can continue to take this to the next level." Which in the SaaS speak is your ARR continuing to go up and up as you look at year over year growth.

And then my last thing is know your audience.

Do the Google, the LinkedIn, find the things that they've talked about, about who you're going to speak to to try to hone in why my firm. What is it about what we're bringing to the table that makes us special, other than we write checks? Because that's the kind of thing that makes an investor be like, "Oh, they want me for a specific reason. They've seen either the stage of the things we're investing in, the types of companies, the types of founders, and they think I would be a good fit for them because of this." It's so important. I'll get these emails, cold emails, and I swear I still get emails from all-male teams that are like, "We think you'd be a great fit for us." And it's like, if you couldn't even look to see that there's no women a part of your team, don't send me those. Those are like auto-delete. I don't respond to them. I do sometimes respond to cold emails. So the more interesting and more non-generic they are, I might respond. But we get a ton of emails. In sending cold emails, it's really important to try to speak to the audience language. Why is this important to me? What is in it for me that will make me be a value add for you? Because the better you have a relationship with your investor, the more it's one where you can come to them when things are going well, but more importantly, when things are going badly. And nobody wants that surprise call. So part of your job as the entrepreneur is sussing out, is this a person that I want to be in it with in the good times as well as the bad times, because these next 12 to 24 months are going to be super intense with the investor founder dynamic.

Find more great advice from Ita, by watching the MasterClass here: https://vimeo.com/manage/videos/754434761.