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93 | 5 Things to Do This Summer So Investors Take You Seriously This Fall

Seed Money · 2026-06-09 · 20 min

0:00--:--

Key moments - from our scoring

Substance score

22 / 100

Five dimensions, 20 points each

Insight Density6 / 20
Originality4 / 20
Guest Caliber4 / 20
Specificity & Evidence5 / 20
Conversational Craft3 / 20

Recognizing that investor responsiveness drops during summer months, Siciliano frames this period as a strategic reset opportunity for founders who didn't achieve their fundraising goals in previous seasons. Rather than stalling, she prescribes a five-part toolkit designed to transform raw customer conversations and early traction into investor-ready evidence. The core insight running through all five recommendations is that organized founders with data win credibility: instead of vague claims about market size or customer enthusiasm, investors want to see tracked customer feedback on specific problems and willingness-to-pay, clear traction dashboards showing signups, retention, or revenue metrics relevant to your business model (whether SaaS metrics like active users or consumer product metrics like retail velocity), and use-of-funds statements that tie capital directly to measurable milestones rather than spending categories. Siciliano also emphasizes the often-overlooked practice of customer interview tracking at the earliest stages - even pre-revenue founders can compile data that demonstrates validation. For those starting sales conversations, she recommends charging for products this summer to prove market demand. The investor research list and pitch feedback rhythm round out the toolkit, addressing both the spray-and-pray pitfall of mass LinkedIn outreach and the mistake of avoiding presentation practice until fall arrives. This episode is most valuable for bootstrapped or pre-seed founders in their first serious fundraising attempt, or those regrouping after a slow spring.

Key takeaways

  • →Track specific customer interview data (problems identified, pricing willingness, current alternatives) in a spreadsheet or Notion and present this evidence to investors rather than making vague claims about customer love.
  • →Create a traction dashboard tied to metrics that matter for your business model - whether SaaS (signups, active users, retention, demo requests) or consumer (waitlist growth, repeat purchase rate, retail inquiries, margin improvement).
  • →Connect every dollar in your use-of-funds request to a specific next milestone (e.g., '50K to reach 10 retail partners,' not '50K for sales staff'), helping investors understand trajectory, not just spending.
  • →Spend summer weeks researching individual investors thoroughly - their portfolio, stage focus, industry expertise, geography, and interests - before any outreach to avoid wasting time on misaligned pitches.
  • →Practice pitching weekly to friends, family, or business contacts (not necessarily investors) and ask only 'What's confusing about this presentation?' to identify gaps and build presentation confidence before fall season.

In this episode

  1. 1Introduction: Summer Preparation for Fall Fundraising
  2. 2Customer Interview Tracker and Data Collection
  3. 3Traction Dashboard: Measuring Key Proof Points
  4. 4Use of Funds Worksheet: Connecting Money to Milestones
  5. 5Investor Research List: Doing Your Background Work
  6. 6Pitch Feedback Rhythm: Practicing and Refining Your Presentation

Mentioned

Jayla SicilianoMark CubanShark TankJerryLinkedInNotion

Topics in this episode

Market segmentationCustomer interview trackerTraction dashboardUse of funds worksheetInvestor research listPitch feedback rhythmWillingness-to-pay validationPitch deck refinement

Questions this episode answers

What customer data should I be tracking in my pitch deck if I don't have many customers yet?

Track who you're speaking with, what problem they experience, what they use today instead of your solution, their willingness to pay, and the language they use to describe their need. Even a handful of interviews compiled in a concise format shows investors you're doing validation research rather than guessing, and something is better than nothing.

What traction metrics should I include in my pitch if I'm pre-revenue?

For SaaS, track signups, active users, retention, demo requests, and pilots. For consumer products, track waitlist growth, pre-orders, conversion rates, repeat purchase rate, and retail inquiries or conversations. The key is showing velocity and proof that people want what you're building, not just vanity metrics.

How should I structure my use-of-funds in a fundraise pitch?

Connect each dollar amount to a specific next milestone you'll hit (e.g., '$30K to launch with 5 retail partners' or '$50K to improve product retention from 40% to 60%'), not to spending categories like 'sales' or 'development.' This shows investors your capital path to growth.

Why is investor research important when I could just pitch widely on LinkedIn?

Spray-and-pray outreach wastes your time and investors' time, reducing response rates and credibility. Researching their portfolio, expertise, stage focus, and interests lets you personalize your pitch to their actual focus, increasing relevance and making better use of your fall pitching window.

When should I start practicing my pitch if I'm not fundraising until fall?

Start now - aim for once-weekly practice presentations with friends, family, or business contacts over the summer. This builds comfort, identifies confusing elements before you talk to investors, gets your reps in, and gives you time to refine based on feedback before fall season.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

6 / 20

The episode delivers five broadly familiar fundraising-prep tips (customer tracker, traction dashboard, use-of-funds worksheet, investor research, pitch practice) with no genuinely novel claims per minute. The content is heavily padded with filler, self-deprecating asides, and repetition of the same points across the summary section.

you should have some evidence of this and I really think it's going to help you out as well
Get some reps in this summer. Don't wait, don't sit on the sidelines and just do nothing with your pitch deck

Originality

4 / 20

Every piece of advice is a standard early-stage fundraising cliché - customer discovery, traction metrics, use-of-funds, investor research, pitch repetition. There are no contrarian positions, first-principles arguments, or counterintuitive frameworks anywhere in the episode.

This whole like just finding someone on LinkedIn and sending them a quick DM. It is a waste of brain space. Stop spamming people.
write down the amount of money you want to raise and connect every dollar to a measurable next milestone

Guest Caliber

4 / 20

This is a solo-host monologue with no guest whatsoever. The host's own credentials are briefly name-dropped (Shark Tank, Mark Cuban deal, angel raise) but the episode draws almost nothing substantive from that experience in terms of practitioner depth.

the lessons I've learned from going on Shark Tank, getting a deal with Mark Cuban, closing down my company, and later building a lifestyle business I love
I did not do this you guys, in the very beginning. And it took me a long ass time to raise the money I needed to raise the angel funding.

Specificity & Evidence

5 / 20

The only concrete figure offered is the host's own $500k angel raise; all other 'examples' are generic hypotheticals (e.g., '50 retailers, 50% willing') with no named companies, real timelines, or verified data points to anchor the advice.

The 500,000 to get off the ground
I've spoken to 50 retailers. 50% of those are willing to take it in. Like, what's the actual data behind the traction?

Conversational Craft

3 / 20

The episode is an uninterrupted solo monologue with no guest, no follow-up questions, and no opportunity for productive disagreement or probing. The delivery is meandering and repetitive, re-summarising each point in the closing segment with little added value.

Might sound like a lot. So figure out, you know, which one of those things do you think you're missing the most?
So that's what I would recommend in a nutshell.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A97%
  • Speaker B3%

Most-used words

money19summer17investors13funding12research12product12pitch11important11deck10start9data9fall8investor8raise8show8market8

Episode notes

If your fundraising momentum stalled this winter or spring, summer is not the time to disappear. It is the time to fix the gaps before investors start paying attention again in the fall. In this episode, Jayla shares a simple 5-part summer reset plan to help early-stage founders turn customer conversations, traction, numbers, and investor research into a stronger, more fundable opportunity. You'll learn: Why summer can be the best time to regroup before your next fundraising push How to turn customer conversations into real investor-ready evidence What traction investors actually want to see in your pitch How to connect your use of funds to milestones, not just expenses Why random investor outreach does not work, and what to do instead How to practice your pitch before you are in front of real investors Have questions specific to your situation? Join Jayla's FREE monthly Seed Money Office Hours call to ask your real funding questions and get more clarity on funding strategy, investor materials, pitching, finding investors, and how to close. Save your spot: About Your Host Jayla Siciliano is an entrepreneur with 25+ years in consumer brands, product, and marketing.

Full transcript

20 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Welcome back to Seed Money. It's Jayla Siciliano here, your host and your I'm gonna say friend today because I love anybody going through this process and even though we have not met, I know that you have the ambition that I just love and respect. And unless you are a complete psycho, I'm guessing if we met, we would be friends. So I am calling us friends through this fundraising process, which can be brutal. We all know. So what we're going to talk about today is extending on last week's episode talking about what to do this summer. Investors aren't going to be as responsive. So how can you maximize the summer months so that you can go into fall really strong and ready to get the funding you need to make your company grow? So whether you didn't close the funding you were hoping to, you know, this fall, winter, spring, or maybe you didn't get as far far, or you didn't push as hard as you wanted to, or you've been sitting on the sidelines, maybe you talked to a couple investors last fall and you just kind of went ah, ah and backed off. It's okay. This is a chance to kind of regroup, take the summer months, reevaluate where you're at and be ready to push in the fall. So what I'm giving you today is a five part toolkit that early stage founders need to turn customer conversations, traction, numbers and all your investor research into a raise ready opportunity. Because when investors start asking the hard questions, you guys, the founder with all their evidence, the most organized gets taken seriously. Let's get into it. Welcome to Seed Money where everyday people learn how to raise capital and get the seed funding you need to finally turn your idea into a reality. If you're struggling to get people to believe in your vision, whether it's a product, an app, or even a real estate deal, this show will give you the insight, confidence and tactics to take the next steps. We're sharing the real side of entrepreneurship and the lessons I've learned from going on Shark Tank, getting a deal with Mark Cuban, closing down my company, and later building a lifestyle business I love. You'll get all the inside secrets on funding, pitching, investors, finding non money resources, and the mindset it takes to get all of that done without big connections or moving to Silicon Valley. Now let's get into the latest episode. Okay, let's dial in and talk about the five things that you can do this summer to prepare yourself to be able to go out and raise funding in the fall. Okay, so we're Going to go through the top five things and we'll kind of break these down a bit. And again, if you have questions about your specific situation, click the link below for office hours. You can hop on the call and um, we can talk through kind of where you're at and you know, if you have any questions on any of these things as it relates to your specific situation. Because again, we're talking about kind of general preparation here, but everyone's situation is a little bit different, a little bit unique and you really need to make sure you are doing the right thing, thing for you. So, okay, the first thing we're going to talk about is a customer interview tracker. And I know this is one of those things that uh, you guys, I hate doing this stuff. I won't lie. This is not my favorite part of business. I like the get in there, figure it all out, put the puzzle pieces together. The second it gets into the like nitty gritty of like tracking and stuff like that, it's not my favorite thing to do. But a gap that I am consistently seeing in pitch decks is customer feedback from a data perspective. Okay, I will see some like quotes and some blurbs and you know, my customers love it, but there's no real like data behind it. And uh, data doesn't mean you have to have a giant, giant, you know, sample set. You can provide data in your pitch deck with not a ton of customers, but something is better than nothing. So what I recommend, okay, is if you are, again, I think most people listening to this, you're very early stage. You either just have no customers, you're pre revenue, or you've got a few customers. But you know, you are not in ramp up stage at this point. Maybe you are, maybe you do need funding for that. And if you do, I'd hope you're already doing some of this stuff. But uh, what you want to make sure you're doing is even if you're not at that higher, you know, ramping up point, make sure you're capturing this information and presenting this to investors. It's going to go a long way to making them feel more comfortable with where you're at. So using a spreadsheet if you want, or notion or whatever the heck tool you want to use, really start tracking, who are you speaking with, what problem are they experiencing? Because again, a lot of us start these things. Uh, I did not do this you guys, in the very beginning. And it took me a long ass time to raise the money I needed to raise the angel funding. The 500,000 to get off the ground. If I had done more of this, I would have learned so much more. Early on I was really creating the product that I wanted and I saw the gap and the need in the market, but I wasn't. I did focus groups. I guess I did do some of that, but I don't think I really was honest about how well I was tracking it. And I think it would have served me really well. So whatever you're doing, talk to customers this summer, take advantage of that, Compile that information. Is the problem they're experiencing what you think it is, what are they using today in place of your solution? I know some of this stuff is like basic. Yes, yes, yes. But again, tracking it, getting it on paper in a concise way that you can show investors you've done this research, what would they pay for? I think this is a really big one. Are you pricing your product on how you believe it should be priced or how the market believes it should be priced? This is a huge, huge, huge piece. So what would they pay for and what kind of language you know would they use? So you don't want to be guessing what your customers want and you don't want investors to think you're guessing and you don't want investors to think you're just building this for yourself. So you need to show proof that you've been actually doing some customer research, you're compiling some data and, and then you can present that. And even if it's not like blatantly in your deck, it's a backup slide, it's a follow up answer, you know, that kind of stuff. Um, but you should have some evidence of this and I really think it's going to help you out as well. So that is a really great thing to do this summer to help not only nudge your traction forward, but to help validate where you're at and your idea and your product and your strategy, all that good stuff. Quick interruption. If you're sitting there questioning how to move forward in getting your company funded, that question can feel so overwhelming. You can listen to all the podcasts, read all the books, and still wonder what the heck actually makes sense for your company and your life. That's why I'm now offering seed money. Office hours. This is a place where you can get out of your head, where we can talk through and strategize your specific situation. So whether you're pre launch, bootstrapping, exploring, angel funding, or mid raise, but not getting where you want to go fast enough, you do not have to figure out your next step alone. Go to seed moneypodcast.com or click the link below. Look forward to seeing you in there. Now let's get back to the episode. Okay, the second thing that I am going to recommend you do this summer, because I am still seeing this in lots of decks, the traction is just not clear. It kind of breezes over that there might be some users or customers, but it is not clear. And it feels like you're either hiding something or again, glazing over it. Neither of which are good. So attraction Dashboard will help you to really focus on what investors are going to care about. So choose the proof points that matter for your business. So might be different if you're a tech founder versus consumer product founder. If you're tech, you know, maybe it's like signups, active users, demo requests, retention pilots, conversions. You should have some of that at the very least, right? Even if you're not charging, which you should be charging, if you're not charging for your product this summer, you need to charge for your product. If you're not getting the funding you need and you're not charging for your product, you need to start charging and prove that people are willing to pay for it. So what's the traction that's important. Start that dashboard and start tracking it. And then that needs to go into your pitch deck or into your investor presentation. For consumer products, it might be like if you haven't launched yet, wait list growth, pre orders, conversion rates. If you're selling online, you know, repeat interest. Like if you only have a handful of stores or 10 stores, like, what's the velocity that you have? Retail inquiries. How many retailers have you spoken to? Like, I've spoken to 50 retailers. 50% of those are willing to take it in. Like, what's the actual data behind the traction? You know, that you're, you're presenting margin improvement. Like, hey, we started off our costs were here, but now we've got our costs down to here and our margins improved and at such uh, and such scale, our margin will improve even more. These are really important things to prioritize, present for you to one think through and also to make sure you have these answers. So attraction Dashboard, because I am seeing way too many decks that leave really the traction out altogether. Or it's just like a little brief something, but it's way too loose and it just is really hard to take it seriously. And it's, it creates more questions than you want it to as an investor is going through and skepticism, which is not good. Third thing, this is so important, a use of funds worksheet. And I don't just mean how you're going to spend the money. Again, we talk about this a lot. I think the term that's used is use of funds, but it should be, I don't know, a fancy smooth term for it, but something like, you know, milestones we will hit. That is really what you want to do. So write down the amount of money you want to raise and connect every dollar to a measurable next milestone. So not, how are you going to spend the money? How is the money going to allow you to hit the next milestones? And what milestones are they? So, you know, maybe it is like number of retailers. That's one of your milestones. This amount of money is going to help us do that. Maybe another milestone is launching a secondary product or whatever. This amount of money is going to help us do that. So we're not. It's not spending money on software or spending money on development or spending money on marketing, you know, or sales. It's spending money to get to this next milestone. That's what you want to lay out. Really important one again. Okay. The fourth thing is an investor research list. So you want to take some time this summer. And again, I talked about this in the last episode. Happy, I'm going to go through this also in the next episode in more detail. But you really need an investor research list and you need to take this seriously. This whole like just finding someone on LinkedIn and sending them a quick DM. It is a waste of brain space. Stop spamming people. Stop just the spray and pray. It is not good. You gotta do your research. So this is. There are tons of people starting businesses and it's the people who do the things that other people don't want to do who are going to get more results. It's just the way life and business works. There's tons of stuff I hate doing and I do it anyway. So you got to do your background research on anyone you're getting ready to talk to. You have to take the time to do that. You know, I, I get pitched all the time for things that I have a no clue about. And it's like, what on earth would make you think that I would, um, invest or want to be involved with that product or space or category? I have no experience there. So do your research. Okay? It's really, really important. So if you have a focus list of angel investors, you know, do they align with the stage that you're in? Are they in your market? Have they invested in companies similar to yours or in your space before? Geographically, where are they? You know, what's important important to them? Where are they at in their career? What are their interests like? Honestly, guys, these are important things you gotta like. And we have so much access to research now. Like, you can really typically find out quite a bit about people check their social media. It's worth doing the research. So an investor research list is number four, number five. A pitch, feedback, rhythm. That's a mouthful. But what I mean by that is that you, you do not want to be practicing your pitch and looking at your pitch deck a week before you start fundraising. And I know you're tweaking it all the time and you're probably practicing to yourself, but take the time this summer to reach out to even just like friends, family members, and just say, hey, here's where I'm at. You know, I know I need funding. I'm kind of hesitating to really put it in front of as many investors as I need to. And I just need to get comfortable presenting this information and getting feedback on what doesn't make sense. And anything that's confusing that right there, you guys, oh, my God, that will save you so much time. It's going to polish you more than you can imagine. So get in a rhythm this summer of like, okay, once a week, I'm going to just present this to someone and it doesn't have to be an investor. And I'm just going to ask them, I mean, maybe have it be someone who, like, has some business background, you know, but what is confusing them? That could be the only question you have to ask. What's confusing about this presentation or this pitch or this deck? You got to have people. I'm sure there's people around you who would be willing to do that and try to do that once a week and then take that feedback. Look for the trend. This is going to do two things. It's going to help you figure out where the gaps are, and, and it's also going to get you more comfortable, which is great. You're going to get your reps in before the fall. So just because you're researching investors, you know, over the summer and maybe not pitching as much, you should still be on some level presenting and getting some reps in and practicing. And again, if you want to do that during office hours, I'd love to have you click the link in, um, the show notes and you can join there. But you also have plenty of friends, family, Neighbors, co workers, anybody with, you know, half a business brain or just hasn't uh, understands your product need, whatever it is, and just get some reps in the summer. Don't wait, don't sit on the sidelines and just do nothing with your pitch deck and nothing with your presentation. Get some reps in this summer. It doesn't have to be in front of investors. So that's what I would recommend in a nutshell. Might sound like a lot. So figure out, you know, which one of those things do you think you're missing the most? You know, is it actual customer data in your pitch deck? Like are you like, oh my God, yeah, I don't have any actual data about my, like yes, everybody has the market slide. Honestly, uh, way too much of that. There's way too much of this high level, here's the trillion dollar market and there's not enough of this granular. Like here's what I've learned about my potential customer and my space and my slice of the pie. That is what's missing. So less of this big, big market opportunity because a lot of that people just glaze over. It's like everybody has that in their deck. It's over inflated pretty much for everyone. Unless you are like literally launching a company that is going to outer space or something, CR in AI whatever. Um, but for most people, way too much of this high level, you know, market information and not enough of the granular information around your customer, who they are, what they're willing to pay and all that good stuff. Second attraction dashboard. What matters for your business, what kind of traction is important and really start tracking that over the summer. You have three months right now. You can get some really solid data over the next three months on retention, percentage of people you've talked to, you know, that are willing to um, buy your product or sign up or pay for it, all that good stuff and make sure you get some sales if you can, a use of funds worksheet. As I said, super, super important. I'm also seeing that missing index, not how you're going to spend the money. Where is the money going to get you an investor research list that really hones in on information about that individual and um, as much as you can find. So you have, you can personalize your approach to them come fall time, end of summer, as much as possible. And just to make sure you're actually not wasting your time and theirs and you're talking to the right people. And then fifth most important, do not stop presenting and looking at your pitch deck over the summer. Get into a rhythm. Get some feedback. Ask that one question. What is confusing about my presentation or my pitch deck? Someone who knows nothing about what you're doing. You will get so much good feedback from that, so I hope that's helpful. Figure out which one of those or which two of those you think would help you the most in validating your company and where you're at so you can come out strong in the fall and have the best chance possible of getting the funding you need. That's it for today. If you want to join the office hours, click the link below and we'll see you there. Thanks for listening to Seed Money. And especially thank you for sharing the show with other people. Every time you share the show, you're helping someone turn their idea into reality. If you've enjoyed listening, uh, the best thank you is to rate and review the show on your favorite podcast app. It not only helps get give me feedback for what kind of information you need, but it helps the show reach more people just like you so they can start their business, raise capital, and get the funding they need. And stay tuned for the next episode of Seed Money.

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