The Diligent Observer Podcast

Episode 42: "Just Fix My Pitch Deck" | Power To Pitch Founder Kat Weaver on Why Communication Beats Perfect Decks, Creative Financing Options for Founders, and the “Founder-First” Investment Philosophy

• Season 1 • Episode 42

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Today's episode explores three ideas that caught my attention:    

  1. Pitch deck ≠ the pitch. So many founders think their deck is the main thing standing between them and funding. It’s about so much more than the deck. 
  2. Corporate grants are legit. I think often about government grants, but have minimized the importance of corporate programs. But these organizations regularly write $10K-$50K checks with no equity dilution – and that is massive for a young business. Plus, the process of applying forms the founder in a powerful way. 
  3. Ghosting sucks – we must be better about this. #1 way to create founder trauma is to never respond. 

I explore these ideas and more with Kat Weaver, serial entrepreneur and Founder of Power To Pitch. She built her first company straight out of her college dorm room and successfully exited after scaling with six figures in pitch competition winnings. Her systematic approach to winning 22 out of 23 pitch competitions revealed that most founders fail not due to bad ideas, but poor communication - insights that led her to launch Power To Pitch, where she's now helped founders raise over $50 million in capital. As both an active angel investor and fundraising coach, Kat brings a rare dual perspective on what works (and what fails) on both sides of the investment table. 

During our conversation, Kat shares: 

  • A systematic approach to corporate grants that delivers $10K-$50K in non-dilutive funding within months - including the exact questions these applications ask and why they're a great alternative to government grants for early-stage founders.
  • Why grant applications are actually founder communication bootcamp - explaining how the constraint of answering core business questions in 100-character limits forces clarity that transforms how founders pitch to all stakeholders.
  • Red flag investor behaviors that signal poor partnership potential - from inappropriate questions to female founders to strong-arming business model changes without collaborative discussion.

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Kat Weaver: [00:00:00] If I had a dollar for every founder who said, all I need to do is fix my pitch deck, I'd be on an island somewhere.

Venture is not for every founder, and not all money is good money. There's no exact path or perfect book on raising. They didn't teach me that in entrepreneurship either. When you refine that language, you're gonna realize that it made you think about the business differently from the way you currently pitch it.

She finally gave in, she has a total now of $155,000 in non-dilutive funding.

I was under contract for my first business four times, and the third time fell through the week of my wedding. You're not gonna go implement every single bit of feedback you hear.

You will drive yourself crazy.

Andrew Kazlow: Welcome to the Diligent Observer, where we help angel investors see what most miss. I'm your host, Andrew, and every week we explore what works, what doesn't, and why through conversations with experienced startup investors and operators.

My guest today is Kat Weaver, serial entrepreneur and founder of Power to Pitch, where she's helped early stage founders raise over [00:01:00] $50 million in capital after winning 22 out of 23 pitch competitions that she entered with her own startup, Kat, discovered that most founders don't fail because of bad ideas.

They fail because they can't effectively communicate the value of those ideas. In this episode, we explore the communication gaps that kill deals, why founders should pursue creative financing before going the VC route, and what founders really think about angel investors behind closed doors. I hope you enjoy learning from Kat as much as I did. 

Kat, thanks for being with me today.

Kat Weaver: I'm super excited to be here. Thanks for having me.

Andrew Kazlow: Okay. So Kat, what are you most excited about right now?

Kat Weaver: Okay, so we just crossed the over 50 million raised in capital from our founders, which has been super incredible and I'm gearing up. I'm most excited 'cause my next personal milestone and for the community, obviously our founders is a hundred million raised, so I'm more than halfway there.

Andrew Kazlow: [00:02:00] And how many founders is that, that, that are underneath that?

Kat Weaver: You know, I'd have to go check. Honestly, I'd be making that number up.

Andrew Kazlow: Okay.

Kat Weaver: know it, but I, we just had 480K closed from one founder and a 15K angel check this morning. it's hard to keep track of which is a good problem. But I, I wouldn't be able to know that number off the top of my head, honestly.

Andrew Kazlow: That's okay. I love the focus on knowing what the most important numbers are for you and for the business, and that is one of those is capital raised. So Kat, maybe walk me through kind of the founding story for what you're doing. I've seen you present on a number of occasions and I see your content all over LinkedIn.

Gimme the story on how you got to this seat and then I'd love to ask you a few questions.

Kat Weaver: Of course, so I like to say I'm a two time accidental founder. Started my first company in college, no network. Thought I was gonna go into medicine and I had people knocking on my dorm room door for this consumer product, a wearable wrist wallet that I had created. Then it kind of took off in a, [00:03:00] in a small way, right?

In an exciting enough way where I switched my major, but then, shortly after starting the business, I had lost everything to a fire and I was back to zero, had nothing, no family money. I was playing tennis, uh, in college. And so that was my job. And then I had a professor say, you should do a pitch competition.

I had no idea what that meant, but that ended up being one of the biggest inflection points for me, 'cause at first pitch I did, I won $7,500 to kickstart the business. And I did 21 more. So my claim to fame is winning 22/23 pitches I applied for. So I realized there was a system to it. It was not an accident.

Uh, It was something that once I got that communication down, it worked over and over and over again. And so I started helping founders on the side. 'Cause I realized, you know, I saw these other amazing entrepreneurs and businesses. But they weren't getting capital because the business was bad. It was because their communication was awful.

And so after six years I'd used that funding. It was six figures in free capital. Actually. I used it to scale and exit, and I wanted to help [00:04:00] founders better communicate to raise funding. And so that's what Power to Pitch was born out of. And to date, we're over 50 million raised. As I had mentioned, we have two core programs, one for grants and non-dilutive funding, and another for getting investor ready for Pre-seed through Series A Capital.

Andrew Kazlow: Amazing. Well, I know that is something that has been so meaningful to so many founders because I've been in just a few of those conversations with some of the founders that have been through your program, and they just speak so highly of the rigor, with which you force them to think through how they're communicating their, their business.

I wonder what are some of the common themes or the common challenge areas that you just see over and over with a founder who has a real business or a real idea, a real thing that they're working on, but it's just struggling to communicate in the right way. What are the common kind of roadblocks that you see?

Kat Weaver: Okay. So, if I had a dollar for every founder who said, all I need to do is fix my pitch deck, or will you just look quickly at my pitch deck thinking that it's gonna be some magic bullet to solve all their fundraising [00:05:00] problems and it's gonna unlock every check. I'd be on an island somewhere, and I think so many founders put this focus on this pitch deck, like it is going to be this magic bullet when in reality it's nothing to do with the pitch deck.

It is everything to do, especially at the early stages with the founder themselves and how they're communicating. And I would be doing them a disservice if I just looked at their pitch deck because I have no idea how they're actually communicating in a conversation. And so I'm constantly, every day educating founders of like, that's not actually gonna help you. It's not the reason. Here's what to think about instead, what to focus on. And you talked a little bit about the rigor, and this is why I vet, every founder in our program is because it is hard work. Venture is not for every founder, and not all money is good money. I wanna make sure that a founder is gonna be coachable in the sense of I'm not gonna touch their pitch deck until I see their pitch.

That is first and foremost, and I would say the second thing is so many founders see the title of someone that says Investor on LinkedIn or whatever platform, and they do [00:06:00] automatic outreach. I'm raising, here's my deck, here's all these things, let's chat. And they don't do the research if that investor is going to be strategic for them. Or if they even invest in their stage or in their industry. And I see founders get desperate and are more lazy. And those are some of the core things. I mean, we could be here all day talking about those, but those are the really, really big pieces that I see on a daily basis.

Andrew Kazlow: It sounds like a lot of your initial work is just helping provide basic education for founders on how this ecosystem works, how they fit, how to think about raising from investors or from grant funding, organizations. Let's say someone is in your program, they are a good fit.

This is a startup. This has some kind of legs to it. Once they're at that stage, what are some of the major over and over and over again, challenge areas for founders as they are doing their best to reorient.

Kat Weaver: That's a great question, and it's not a one size fits all. I will [00:07:00] say I don't think founders, at, even at that stage consider all of their financing options. You see this TechCrunch and Forbes article and it's like, oh, I gotta go the venture route, or I'm gonna take on angel investors. I always recommend a combination of capital no matter the stage.

From calling it like, customer financing, pre-sales, all the things before you're ready, and then you've got. Various forms of debt. Debt is cheaper than equity, and I think it's a red flag when a founder doesn't wanna consider alternative options, or even they're in the consumer product space and they haven't considered inventory or PO financing. You're gonna give up a lot more equity on your cap table versus thinking about some other creative options and lowering the amount that giving up.

Even from like, you know, the credit card route is now for everyone, but it's like if you can leverage little bits here and there to get over some humps instead of waiting on capital, the grant route, if you're under a million ARR. There's so many things, and I even like, some of the other investors that I know.

I say, ask about these options. Suggest them to the [00:08:00] founders because it's not natural to know all these things. It's not super clear. There's no exact path or perfect book on raising. They didn't teach me that in entrepreneurship either. Like I just had to figure it out and hack my way through the system and share that with others.

So I get that it's not natural, but I always say like a combination of capital, no matter that stage is something like going, the creative financing route is more realistic than just going pure venture.

Andrew Kazlow: I love this concept of creative financing. You know, it's so common to see a founder that's applying to an angel group or sitting down for coffee and they've not raised any capital yet. They have no outside financing and their response when asked why, what I've heard commonly, I'd be curious to hear how often you hear this, is, oh, well, I'm too early for traditional financing.

None of those other options are available to me yet. How often do you hear that and where do you point people to start? Maybe the grant route? Pitch competitions probably one of your [00:09:00] favorites.

Kat Weaver: Yeah, and well, I asked like, why haven't you started a wait list or pre-sales? That's first and foremost. Before you do anything else, what's your hesitation? What is your problem with perfection usually is what we're like trying to unpack in there. And then the second is I love corporate grants. So government grants are very different beast. They are typically a lot more money, but it's more of like a credit system. There's a lot more strings attached. It takes quite a bit longer. And I know a friend who secured a $5 million government grant and regretted it 'cause he had to hire three people just to manage the process and hopefully get paid out eight months later when they submit you know, for reimbursement and all that kind of stuff.

So I love the corporate grant route for founders under a million because, and it's not like consistent reoccurring capital. But it's meant to be a small cash boost. It's not a loan, you don't pay it back. It is pure cash in the mail. A peer grant is, and it also comes with PR, credibility, potential mentorship.

You don't have to give up any equity. Even the past month, we had three founders win some smaller grants and they had been trying to raise for over a year with [00:10:00] no luck. They secure this grant, it got them over this little bit of a hump, got them some PR, another advisor. And then use that to end up successfully completing their full raise.

And so that, becomes a little bit of a boost in so many ways. And I hear all the time, it's like, I don't have time for that, or they're only for nonprofits, or you know, it's not worth it. I'm gonna get rejected. They're too competitive. None of that is true. Actually there in our grant program, we share 200 plus grants every single month.

There are so many out there. I had someone win 25K yesterday morning, who had never won anything before. And so there's a system to it, but I would say if you're not at least trying it, you're missing out because there's so much more that can come from it outside of just the pure cash basis, and I'm a living testimonial of that.

Andrew Kazlow: So, so speaking from. And maybe looking from the investor's perspective, we're co-investing alongside a lot of this kind of capital from these different grant organizations. Maybe give [00:11:00] a quick primer for, let's say I'm a, I've been angel investing for a year. I'm in a few deals looking for a few more, getting a little smarter.

Explain to me the corporate grant process at a high level. Like who starts these? What are they motivated by? Where do they land? Like how does it work? And maybe differentiate that a little bit more clearly from the government grant, which is often a little bit flashier, bigger dollars. A lot of the time it has these interesting, performance elements attached to it.

Kat Weaver: Sure. I, I also, I break this down really in depth on my YouTube channel at Kat Weaver, but at a high level organizations like FedEx, Verizon. We had a founder win $50,000 from Progressive last year. Others, they get tax incentives. It is also PR for them. They drum up a ton of business and insight and data from these types of applications.

And then a year from now they wanna do PR on you and brag about you of how much they impacted you in the business. And so it's a win-win for everyone around. [00:12:00] They want someone who will represent them well. Of course that makes sense. And the check sizes on average are between a thousand to 200,000 even plus I will say it probably rounds out around the 10 to 25K that come a bit quicker.

You can get paid out in a month or less. Sometimes it's a few months, but that's still quicker than the government cycle, which might take a year or two.

Andrew Kazlow: Sure.

Kat Weaver: There's grants for every industry in the corporate world practically. From, I'm, I'm an idea to all the way of like something super niche or local chamber of commerce has them, like. you name it, I haven't not seen an industry represented. And then on the government side, I will, I typically see it's more health-oriented, government defense, super deep tech, things like that. So it's not as supportive from an industry perspective. And then even on the corporate grants side, like lifestyle businesses, some smaller folks and on the government side typically have to be a little bit more developed. And I think that the, on the corporate side too, the [00:13:00] expectations are, you know, oh, it's gonna take too long or I need a professional. Can take anywhere from an hour to two hour doing it right and batch applying. So it's so doable.

There's absolutely no excuse for a founder to not set aside one or two hours biweekly even to be able to secure and get enough insight from that. And I always say, an opportunity to pitch is never one wasted because on the corporate grant side, you can ask for feedback and it's helping you organize categories of the business where the government grant, that application is gonna take you days and you're gonna pay someone to do that for you.

Maybe even two people. Corporate grant is so simple and they all ask the same core questions. Your story, what are you gonna do with the money, your competition? So it does become a copy and paste process.

Andrew Kazlow: It is funny as you're talking, Kat, I'm reminded of my college application days and the scholarship process. This feels like the same thing, but in a totally different space. Is that a fair comparison? Where would you disagree with that?

Kat Weaver: Yeah, I mean, to sit down and like [00:14:00] write something out. Sure. But it's not one long pitch. It's like, all right, you have a hundred characters to give us your story. Then you have another a hundred characters to tell us your target market and your competition. And they purposely keep it short, maybe anywhere from a few questions up to 10, 20, or 30.

And you're answering it in piecemeal so it's not something super structured, but they really want like the story and that essence. And then energy from a founder versus something super curated. Like they can tell if you're using AI and it sounds so scripted. they, They want that like scrappy founder 'cause they wanna fuel that again and give you that little taste to kind of get to that next level.

That's what it's, meant for. That's how I would sum that up. The beauty is that, that language transcends across sales. Maybe pitching retailers on your website. When you refine that language, you're gonna realize that it made you think about the business differently from the way you currently pitch it. And that's one of my favorite exercises of why I say, don't go hire someone to do that, because you need to do that work to become a better founder and a better communicator.

And I'll give you one [00:15:00] example. We had one founder. She used the same core pitch. So a core of building out for a copy and paste is really like a five to seven minute investor pitch structure. You can break all those core categories out. And paste them into the majority of these questions. And she was kind of fighting us on this 'cause she was one of those of like, I just wanna send you my pitch deck.

And I'm like, not gonna happen 'cause I can't help you with that and I'm not the right fit if you're not gonna let me look at that language. She finally gave in and she won three grants totaling $90,000, huge PR. She's gone on to win. She has a total now of $155,000 in non-dilutive funding. And I would say that 155K is a little bit above average, but from the same pitch format.

So it's like another great example and we had one founder, four grants, $63,000 and all of that, the same core pieces. Just maybe moving a couple words, making sure you fit within the character or word counts that easy.[00:16:00] 

Andrew Kazlow: So if I'm an angel, I should really be expecting to see some non-zero amount of non-dilutive funding on just about every founder's story. If there is none of this, my question, which you point to earlier is why not? What have you done to engage these free or low cost sources of capital?

Kat Weaver: I would say it's not a requirement. I don't think that they're a lesser founder if they haven't tried it a lot. Don't know about it. But I would say that if they're in the really early stages, like pre-sales, they're under 10K MRR especially, and they haven't thought about alternative options versus just going the investor route, and they're probably a little desperate at that point.

That's why they're doing it. They're not as profitable. It's something to advise upon or ask. But again, it's, it's not super common. It's why I do what I do because the majority of founders I meet are like, I didn't even know that was an option. I had no idea about that. So I wouldn't use it as a judgment marker.

I would use it as an educational tool and a guide to really figure out maybe where some of their weak points are of like, why go the investor route when you could [00:17:00] get something a little bit cheaper and push them on that, to make sure that it's a, a good fit.

Andrew Kazlow: Well it sounds like even, Hey, go through the process. Fill out 50 grant applications. Then come back let's hear your pitch again.

Kat Weaver: Fill out five, it'll change your language. Fill out 10. Oh my gosh. We're in another dimension. Doesn't even need to be 50.

Andrew Kazlow: Yeah. I mean, it sounds like that the bigger value here that I see as an investor is in the refinement of the vision because what you're working them through is this capacity to articulate the vision for the organization in a concise, compelling way, which is exactly what they need to be able to recruit and sell longer term, which is, that's the job as a founder.

So, I love this. I think that's a hack that I'm for sure gonna add to my back pocket. Okay. I want to talk a little more about the, so the equity fundraising side. We talked a little bit about grants and different avenues there. I'm really curious to hear about the things that you hear founders talk about behind closed doors.

'cause I, Correct me if I'm wrong, but I see you as like the [00:18:00] fundraising therapist for a lot of founders. Like you're working, you know, founders are going and, and pitching. They're applying, they're talking to investors. Then they're coming back to you going, oh my gosh, it was, this went great.

Or, holy moly, this is horrible. Here's where I screwed up. Unpack for me and for our listeners, like what are some of the things that you hear founders share with you in that sacred space that angel investors just don't understand or don't seem to be getting the memo on. Like what are the things that they complain about from Angels again and again and again, that if you had a mic and you could talk to every angel investor in the world, you would tell them about.

Kat Weaver: Okay. I am so glad you asked me this question. This is a really good one. I think the first point of heartbreak is being ghosted, like at least not getting a "no". And The next level is giving 'em a little bit of a why. But when a founder gets ghosted, I see them go into a literal spiral. Like it is the most personal [00:19:00] thing, like a personal attack in a way of like, what did I do wrong?

What happened? This, this, this? And sometimes we're busy, we're seeing a lot of deals that happens, but it's the ghosting that really freaks people out. 'Cause I tell founders they're lucky if they gotta no. You got a direct answer. And I will say if it's a no, is it a no, not right now. Come back to me when you have X, Y and ZKPI.

Or is it a, no, I don't even invest in this industry. I don't know why you bothered to pitch me in the first place. I think that will save both sides time. And I know it's a lot of emails, but like the right founder should also be emailing you maybe five times, to try to get an answer? So if you don't want that to happen, give them a no.

And then the next frustration point would be not getting feedback like, oh, I pitched them and I didn't hear, or they said, no, it's like I would've loved a little bit of insight as to what turned them off or maybe what I can do better. And it doesn't mean that they're gonna take that piece of advice, because what I tell founders is, you're not gonna go implement every single bit of feedback you hear.

You will drive yourself crazy. You [00:20:00] log that feedback and when you hear the same thing two to three times at a minimum. Then you go implement those changes and you see the themes of like, I'm getting feedback on my three year projections, or my competitive analysis sucks, or whatever it is.

But if someone makes one tiny comment, yeah. Again, it's, you're not seeing enough people to get insight on that and it's, you're gonna go nuts. So those are the two biggest factors I hear. And it comes in a few different forms, but like those are, that's it.

Andrew Kazlow: That's so funny 'cause it's just such a, it feels like right, you we're here talking and it feels like such a low lift for an investor to be direct and to give a, give a response. But seeing, right, see, seeing the lives and knowing these angels, it's so often not intentional. It's purely, now that's not always the case.

Sometimes it is, I don't wanna own up and make a hard decision. Just get busy, get distracted, forget something else is more pressing. But investors, operators, anybody listening to [00:21:00] this, one of the kindest things you can do for every founder that interacts with your organization is just give a clear response.

Kat Weaver: I know some funds who internally, they have a pass and track, as in we're passing, but we wanna secretly watch them. Pass and no, as in absolutely not a fit. And then obviously like, yes, the deal you know, we're going into further diligence, but if it's passing track, tell 'em what you wanna see. That's gonna motivate the founder.

And then you can tell if they're coachable and when they come back to you, like, did they actually listen? What did they learn, achieve? It's a win on both sides. 

Andrew Kazlow: So you mentioned, another strategy, which I love about processing investor feedback of making sure you get, two, three plus situations where you're getting the same piece of feedback. What are the themes that you hear from investors giving feedback to entrepreneurs that's just like horrible advice because I, I know there's a lot out there and I have a lot of pet peeves about other investors giving horrible advice, but what are some of the themes

you [00:22:00] hear a lot from founders?

Kat Weaver: Uh, female founders have it the worst. I have a running list of actually some of the ridiculous things that investors have asked or said, female founders, and they're all anonymous. But from when do you plan to have kids? I hope you don't have more kids. What does your husband think about this?

The berating around the capability of the female founders still happens in his 2025.

That is so much more common than you think and it's really, really unfortunate. I've even had people tell me, oh, your content is only working 'cause you're cute to my face. And I'm like, well, I've helped founders do X, Y, and Z.

It has actually has nothing to do with that. I take my work very seriously and I've been given these comments and that guy means absolutely nothing to me. I want nothing to do with him, and it is what it is, but it's just unfortunate and shocking that some people feel comfortable saying what they say to female founders.

I will say too [00:23:00] is I've seen some investors get really aggressive on wanting to change a founder's business model. Instead of it being a conversation of like, have you thought about this in this way versus, I'm not investing if you don't do this, and the founder's like that wasn't even on our strategy plan.

That doesn't mean that both siders like maybe right or wrong, but it should be more of a collaborative conversation, not some strong arm opportunity, because out of respect for the founder and what they're doing, I would say too. And hopefully that founder is not desperate enough to take a check like that from someone wanting to stronger than them, but I do see it happen.

So that is one and the third I would say is from non-experienced angel investors. One of my founders in the program, she's really regretting accepting a, a, a big check from this guy years ago, and he calls her, forcing her to do certain product launches, telling her he just wants his money back, she needs to exit sooner, she needs to be bought out.

And she's like, I can't get this guy off my back. I'm trying to buy him out. It's just more expensive. And he wasn't a strategic fit for her cap table [00:24:00] to begin with, and that was on her and she needed the money and she made a judgment call that wasn't the right one at the time. But those in terms of that kind of force is something that no one wants to have to deal with at the end of the day.

Andrew Kazlow: So on that point, maybe just to double click a little bit further, we talk a lot on the show about the difference between smart money and dumb money and how every investor ought to strive to only participate when they can actually serve as smart money. And that they really should only be given opportunities to invest in opportunities where they can serve as smart money.

Walk me through your framework of how you encourage your founders to make this assessment for themselves as their getting to know an, a potential investor. The best founders, the most compelling opportunities, I believe have their pick of the litter in terms of investors, and so the investor needs to win their rights to be able to deploy those dollars.

Walk me through your framework for how you help founders evaluate. Is this prospective [00:25:00] investor fit?

Kat Weaver: I love that you said that. So I actually just brought on a new founder this two hours ago because they had never thought about what an ideal investor profile looked like. They said we'd never heard of that. You're just pitching for any type of capital. And what we talked through was I believe, every single founder and I have a whole document in my program of what and how to build out an ideal investor profile.

In terms of stage, industry, who's in their portfolio that you want a connection to? Who can they make introductions for? They don't have to be a user of the product, but like where, what areas, what buckets do you want value in? Supply chain, marketing, retail, enterprise, whatever it is actually. Like list those things and if someone can't bring one of those to the table, you gotta filter them out and like you said, like I say, not all money is good money, right? Money is abundant, but the right money, that's a different story. And so building out that filter is so key because then now as the founder, you [00:26:00] hold the keys and you're going to do outreach differently.

Like I met a founder who has paid for a 15,000 person investor email list and sent the same email blast to all of them and shocking, not one replied.

Andrew Kazlow: Oh no.

Kat Weaver: You know what I mean? It's like I thought that would, that's obvious to me, but clearly it wasn't obvious to them. And so building out that kind of filter.

And I also advise against founders. I get offered equity a lot. And I don't think that's a good thing because they didn't do any diligence on me. We even had one call. I'm getting DMs, giving me equity for something that is unrelated to me. And so, if a founder approaches you and you're like, Ooh, I want equity and this and that, and all these things, or maybe a little bit of cash or whatever it is, a combination.

That should be a huge red flag. If they didn't try to diligence you first in that sense. And you know, I'd rather have a 100K from someone super strategic, even 50K, then someone who's not at [00:27:00] 250K. And the last thing I'll add around this is I see a lot of founders go after, try to do something like barter for services.

Or agencies of like giving up equity, a lower retainer, some cash. And I think that model is really dangerous because if you can outgrow an agency that fast, they're dead weight on your cap table. And so even like as an angel, when you look at a founder's cap table who's active, who's like serving like resources and has actual capabilities here versus who's dead weight.

And that's gonna tell you a lot about the founder and what they're willing to give up and how easy they can be coerced into something or haven't done the research.

Andrew Kazlow: I've seen that so many times. 'Cause it's so easy, right? It's like all you have at the beginning is an idea, a whole lot of dreams, and this precious little equity pool, and you're like, oh, okay, I can.

Kat Weaver: Only so many slices of the pie available.

Andrew Kazlow: Man, that that pie gets, sliced up really, really fast, uh, as you take [00:28:00] that approach.

I'm curious, Kat, like, I dunno, I just, I just think you're such a fascinating perspective. 'Cause I mean, helping so many founders raise 50 million, you've seen so many rounds, plus having been a founder yourself and winning on these pitch competitions. If you're sitting in the angel investor seat, what are some of the things you're poking at or asking about that maybe the average angel wouldn't think to poke at, like given that perspective, given your experience, like what are some of the things that you think are uniquely important that maybe you feel like the rest of the ecosystem doesn't give enough credit to or pay enough attention to?

Kat Weaver: So I actually, My husband and I had visited a company yesterday to potentially personally angel invest, and I had asked about the company's IP for their software. And they gave us some bs roundabout answer, an analogy that had nothing to do with their IP. So, I asked them again, have you [00:29:00] protected your IP? Another roundabout answer, and I look at the other, there's two guys there, and I look at the other one and I was like, so that means you don't actually have your IP protected? And he looks at me, he goes, no. So when a founder is trying to dance around the answer and can't me give me something direct and is trying to hide that in a way, or think that he is made some fun statement to like push me out of getting the actual answer, huge red flag. To me, like my eyes blaze over half the rest of the meeting. 'Cause I'm like, what else are they lying about? What else are they trying to finagle? Because that is what you're investing in and becomes actually valuable. So that was a huge red flag. And then the second is, your due diligencing a founder, right?

In this process of to invest. But if the founder hasn't made an effort to diligence you, and ask you questions and make sure that you're right fit, another red flag. So it's not just like, oh, about what you are doing. It's what lens are you taking that like the founder is doing and how responsive they are. [00:30:00] Don't give me any work. If you want my money, if you wanna figure it out, you gotta be the one putting in all the effort and sending me details, updates, expectations. I also thought it was a red flag, so when I was looking at this deal in particular, their data room was one of the worst I'd ever seen. It was so minimal, so unorganized. Not even a pro forma, no projections. And their excuse was, oh, we haven't touched that in over a year. And I'm like, you're claiming you're gonna have this $9 million plus contract and you're spending all this money and you haven't even mapped out what that's gonna cost or what that's gonna look like. I left that and I was like, I can't imagine investing in this company because of the disorganization and the lack of focus. And I know we're wearing all the hats. Like I give 'em credit to like, man, they're, it's like drinking from a fire hose, you know, and you're building and raising at the same time, but huge, huge, huge red flags there.

Andrew Kazlow: It makes sense. I would imagine, given that you're whole [00:31:00] business is about equipping founders to free as well, and helping them think through how to present information and get organized, get structured. I would imagine you have a very high bar for expectations on what gets talked about, how it gets presented and communicated in a prospective investment conversation.

Kat Weaver: Honestly, I don't have a super high bar for that because you know, not everyone can afford or like goes that route to get it kind of professionally cleaned up or in that right structure. I index heavily first on the founder and their ability, like if I feel that they're gonna be gritty, coachable, transparent, passionate, like they're those qualities, they've already got one big check in my book.

Like, are they gonna do right by my money? And I mean, I personally have to use and like the product or know how to support it. And in that sense, that's everything that I've invested in. I also love former athletes, so myself, I think they know how to sacrifice things a little bit differently. So actually two of, if not that could be the third, but for sure, two of [00:32:00] my angel investments have been former athletes.

And I just think they hustle differently, so it's not a pure requirement, but I'll index a little bit differently based on that. So yeah, I'm not gonna judge of like, oh, they've got this perfect pitch and deck and all that. It's what's the effort? What are they willing to sacrifice and what do they want from me?

And if they can do those three core buckets, we're in the next stages, essentially. 

Andrew Kazlow: Interesting. I'm surprised to hear that. 'Cause I would think in your shoes, I'd be like, oh no, it has to meet my super high criteria. But I love the thoughtfulness in the way that you are leading with the founder first component. I think that's super generous and fits the spirit of angel investing, which is

you can have all the best projections and data, and it all makes sense on paper. And if I have a bad feeling about you, I'm out. And that's a right call because this is a very intimate form of investing or vice versa. You could have all the wrong stuff over here and this is messed up, but if I like believe in this person, then it could be a great partnership and it's probably a fit.

Kat Weaver: Totally.

Andrew Kazlow: So maybe tell me a little more [00:33:00] about what, what does the future hold for you, for the business, for the ecosystem? Like, what are the things that, let's say you have a blank canvas, it's five years from now. What, What does the world look like that's different, as a result of what you're doing now?

Kat Weaver: Well, I'll be well past the a hundred million range, that's for sure. Uh, two is I've been working on our own internal pitch software, which I'm really excited about. Third is I'm definitely gonna write a book. I dunno what it's gonna be. Probably around this space. And I have some crazy stories, I was under contract for my first business four times, and the third time fell through the week of my wedding.

I mean, from losing everything up higher, like you name it, I've probably experienced it and I'm tougher because of it, but man in the moment was it feel like, it felt a little like it was over, you know?

Andrew Kazlow: Okay. Well, but, but can, can we hear the story now or do we have to wait for the book? Because I, that sounds horrible, but I'd love to hear the story.

Kat Weaver: Well probably, well parts will be in the book, but I, at a very high level, like I had a beautiful all cash [00:34:00] deal for my company. We literally was supposed to close that week and I was already prepping to move that inventory out. I was gonna be on my honeymoon and another one of the, their businesses went under and claimed they needed that cash to.

All of the bring the business back to life and all this, whatever, they could have made something up. I don't know. I that feeling of like, I'm about to have a rehearsal dinner in a few days and leave on Monday, what is happening? That was a soul searching moment if I've ever had one.

So, and Then I had a mentor who is no longer a mentor, say, you should sell your company for a dollar, just to say you sold it. And that fire inside me, like you would not believe.

Andrew Kazlow: Add that to the list of worsts. uh,

Kat Weaver: Right. It was almost a year later that I finally ended up selling. Like I held onto it and struggled for a bit, but

It was, it was worth it and can't believe all the mentors and advice you hear. I [00:35:00] had another, you'll love this, who said, you know, a few years from now I better not see you as the pitch girl. You don't always wanna be known as the pitch girl. You, You could do great in corporate. And I never talk to that person ever again.

I am the glorified pitch girl and I am damn good at it, and I have made a lot of impact. I have no shame around it. Uh, And so I think some people take as some investors or mentors very literally, and I'm grateful that I was able to take this other lens of that doesn't sit right for me. I appreciate your time and

what you have to say, but not really. So thank you and I'll never see you again.

Andrew Kazlow: Yeah. I feel like as investors it's so easy to feel like the power it lives with you as a capital provider. And yes, the capital is valuable and there is for sure power there, but I feel like it's so easy to forget that the reason we're investing is that these founders and the [00:36:00] companies that they're building are the real value.

Like we wouldn't be investing here if we didn't believe that each of these opportunities could go to the moon, right? Like the power in this, the value in this ecosystem is in the founder and the businesses that they're building. And it stresses me out so much when I hear stories like this of investors thinking they have more power than they actually do without truly stewarding what is the most unique and valuable resource in that room, which is the person that they're speaking to and the businesses and the communities

that founder is building and cultivating as a result of their work like that is the value creation in this whole picture. And we can never forget that as investors. So I hate that that happened to you, but I am so glad that you have continued on and are

Kat Weaver: What do you mean? I'm glad it made me so much stronger and now I get to say like I beat those idiots and everyone else is capable of doing it too. So in the moment I absolutely did not feel like that, but because it happened, I am so much better for it and I'm so grateful that they came across my path [00:37:00] because that experience you can't pay for.

Andrew Kazlow: Hmm. I love it. Well, anything else? What else, 

Kat Weaver: More,

More capital raised. Uh, I would say like, I've always dreamt of making some sort of pitch standard more available to founders. Like Y Combinator has given the safe and Founders Institute has given the fast agreement for advisors and some of these standards. But, you know, you can Google all these pitch standards, but what if there was a pitch standard recognized by other investment groups in terms of pitching, and that education was more accessible for a founder to understand and

carve out in their own way. And that's something that I haven't formally put together, but I've been thinking through a lot of like, how can I build out a standard that becomes more accessible and widely known because it checks these core boxes and it's gonna give more opportunity to more people.

Andrew Kazlow: Hmm. And is that where this, this software platform that you're thinking on fits in or how does that all connect?[00:38:00] 

Kat Weaver: Part of it in some way. I haven't fully hashed it out, but I'll let you know in a few years. I'm sure I'll have it figured out by then.

Andrew Kazlow: Sounds good. Well, excited to stay in touch with that. Kat, final words of wisdom, words of advice you would leave for our angel investor listeners.

Kat Weaver: Trusting your gut on the founder more than the business itself is always the better bet. And the bigger bet I would say is because of that really early stage, the founder themselves are less replaceable 'cause they are the business at that point. So, if you're thinking about just indexing on their data room and their financials, I would highly encourage thinking about them and their qualities as a founder and their capabilities and what they're willing to sacrifice, because that is where the real founders make the difference in the shift and are gonna do the most right by your money.

Andrew Kazlow: Kat, this has been a pleasure. Thank you so much for joining. I very much look forward to the book and all of your content.

How can our listeners stay in touch with you? You have [00:39:00] recently been investing in quite a bit of content, so how can we stay connected?

Kat Weaver: Yeah, I share a ton of founder insights advice, so if you're thinking about a deal or a founder's not just there yet for you and you want 'em to have a little extra insight or get some insights yourself, I'm very active on LinkedIn at Kat, K-A-T, Weaver, W-E-A-V-E-R. And my new YouTube channel as well as Instagram, it's all there.

Like you said, I've been spending a ton of time there trying to figure it out and just not enough founders know about me yet. I do a ton of free trainings and I share them on all the social there for founders to get insights on pitching and or kind of a grants masterclass. It's all there. So whether it's for yourself or a future founder, I'd love to meet you there. Send me a DM, I open every single one of them and I'm just here to make some founder lives better than make the investors happier too at the end of the day.

Andrew Kazlow: Fantastic. Kat, thank you for joining me today, and I look forward to our next conversation.

Kat Weaver: Yeah. Thanks so much for having me. It was a great conversation. Appreciate it.

 Thanks for listening to this episode of The Diligent [00:40:00] Observer. I'm your host, Andrew, and if you're an angel investor looking for essential angel intel in five minutes every week, I think you'd enjoy my newsletter. I send my best stuff, interesting deals, and more straight to your inbox so you never miss a thing.

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