Episodes

  • Why Your Pitch Is Falling Flat: The Power of Story
    Jan 20 2026

    Numbers won't make them care—your story will. In this episode, you'll learn how to grab investor attention with a pitch that actually connects. If you're tired of wasting time and getting minimal responses, this is your wake-up call. Hit play to learn how to stand out.

    Topics Covered;

    • Why your founder story matters more than data at the early stage

    • What investors are really evaluating when you don't have traction yet

    • The three elements that make a founder story credible instead of pitchy

    • How to tell a problem story that creates trust in under 60 seconds

    • Why investors back conviction before they back certainty

    • The biggest storytelling mistakes founders don't realize they're making

    • How emotion builds credibility without sounding dramatic or rehearsed

    • Why skipping your personal "why" quietly weakens your pitch

    • How to structure your story so investors want the next meeting

    • What makes an investor believe you won't quit when things get hard

    About Your Host

    Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!

    Connect:

    Website: https://seedmoneypodcast.com/

    Instagram: https://www.instagram.com/jaylasiciliano/

    Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/

    Subscribe, Rate, & Review

    Please rate, follow, and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show!

    Disclaimer

    The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.

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    19 mins
  • This Exercise Can Predict If Your Fundraise Will Work in 2026
    Jan 13 2026

    It's 2026, and it's a good time to refresh your fundraising mindset. Budgets are fresh, investors are considering where to put their money, and LinkedIn is buzzing about how "now is the window."

    If you position yourself correctly, you could have closed your funding round by June.

    But no matter how much motivation you have, or how fired up investors are, founders are still being held back by basic, really simple gaps in their approach. Gaps that seem minor but quietly cost you momentum, meetings, and ultimately the funding you need.

    Most founders don't lose deals because the idea isn't good enough. They lose them because of what's missing in their strategies (even if they have a great business or idea).

    So before you send another pitch deck or book another investor meeting, there's a simple exercise you can do to make sure you're not getting ruled out before the conversation even starts.

    What are investors noticing that you're too close to see? What might be quietly stopping them from ever responding?

    In this episode, we walk through a simple but confronting exercise every founder should do before sending another pitch.

    Topics Covered;

    • Why most pitch decks fail before the first meeting even happens

    • The exercise that exposes hidden deal-breakers fast

    • Why paragraphs, jargon, and over-explaining silently kill investor interest

    • How to clearly answer the real question investors care about

    • The credibility gap founders underestimate and how to close it without revenue

    • How unrealistic valuations signal self-awareness problems, not confidence

    • The difference between how founders think investors evaluate deals and how they actually do

    • The true barrier to fundraising (not market conditions)

    About Your Host

    Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!

    Connect:

    Website: https://seedmoneypodcast.com/

    Instagram: https://www.instagram.com/jaylasiciliano/

    Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/

    Subscribe, Rate, & Review

    Please rate, follow, and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show!

    Disclaimer

    The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.

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    22 mins
  • The Fundraising Advice Founders Never Hear (But Desperately Need) w/ Shefqet Avdullau
    Jan 6 2026
    Getting an investor to fund your business isn't just about your idea, industry, team, or even your business model. What can help or tank your efforts often comes down to how you show up in the room. Your mindset, how you handle the power dynamics, and whether you actually see yourself as the one offering value, not asking for it. The truth is that many founders operate from a place of desperation, and investors can sense it immediately. You lose sight of the fact that you and your business are the prize. You treat the investor like a boss, not a peer, or you say your schedule is completely open. You come across as overly eager or grateful for the opportunity. These are all things that quietly make an investor pull back, even if the idea itself is strong. If you walk into investor conversations acting like you're asking for permission instead of offering an opportunity, getting funding is harder. This is something founder-turned-angel investor Shefqet Avdullau knows all too well. As a super-connector with deep experience on both sides of the table, he brings a rare perspective shaped by building, exiting, and now backing companies. How should founders actually show up in investor conversations? How do you know when an investor will help you build something, or quietly make things harder? In this episode, we unpack the parts of fundraising no one puts on the pitch deck: why desperation is detectable (and deadly), why treating investors like they're above you destroys leverage, and why confidence is often what really moves a round forward. Topics Covered; Why fundraising fails before the pitch even begins How to avoid looking desperate to investors The subtle signals investors read instantly, including desperation and lack of leverage How to engineer FOMO using calendar density and scarcity Why "owning the elephant in the room" builds more trust than perfect metrics ever will The soft-commit strategy founders should use before officially opening a round Why a bad investor is often 10x worse than no investor The SAFE agreement mistake that can cost you your company Why easy yeses are a red flag, not a win The "two-week vacation test" reveals if you've got a company or a stressful job How founders accidentally become bottlenecks About the Guest Shefqet Avdullau is a founder, active angel investor, board advisor, and "super connector," primarily in the tech ecosystem. He has made 17 investments in the last four years, with two successful exits. Today, he backs advisors and mentors tech startups, using his experience to help new founders navigate the challenges with strategic funding and real-world guidance. Having started his career as a software engineer and later founding, scaling, and exiting his own ventures, he brings an operator-first perspective to early-stage investing. For more of Shefqet's insights, find him on LinkedIn. About Your Host Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality! Connect: Website: https://seedmoneypodcast.com/ Instagram: https://www.instagram.com/jaylasiciliano/ Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/ Subscribe, Rate, & Review Please rate, follow, and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show! Disclaimer The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.
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    46 mins
  • I Listened to 16 Founder Pitches: Here's What Most People Miss
    Nov 25 2025

    We spend so much time stressing about pitch decks…the formatting, the stats, and the perfect slide order. But honestly, that's not what trips most founders up.

    The real issue is way simpler: a lot of us just aren't telling investors what they actually need to hear. Not because our ideas are bad, but because the way we explain them ends up hiding the good stuff.

    Last week I listened to sixteen founder pitches in a row. Different industries, different personalities, and different business models.

    And while every single one had real potential, almost all of them shared the same 5 blind spots.

    What stood out wasn't the mistakes themselves, but how shockingly easy they are to fix. The founders who nailed just a few simple things immediately came across clearer, more confident, and honestly… way more fun to listen to.

    The difference between a forgettable pitch and a memorable one usually isn't a full overhaul. It's tiny tweaks, and once those clicks happen, the whole pitch lands differently.

    In this episode, I go through the 5 common mistakes I see in founder pitches, and why correcting them will get (and keep) the attention of investors.

    Topics Covered;

    • Why most founders bury the most important part of the pitch

    • How jargon kills investor confidence, even when the idea is great.

    • The "single-takeaway rule" that instantly makes your deck clearer and more persuasive

    • What investors actually want to know about your funding ask

    • Invisible deal-breakers: lack of passion, weak projection, and low energy

    • How to present traction even when you don't have revenue yet

    • How to communicate a credible 18-month plan investors can believe in

    • Verbal, visual, and emotional signals that matter far more than data points

    About Your Host

    Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!

    Connect:

    Website: https://seedmoneypodcast.com/

    Instagram: https://www.instagram.com/jaylasiciliano/

    Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/

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    13 mins
  • Pitch Battles, Warm Intros and Demo Days Are Dead: The New Way to Raise Capital w/ Robert Harary
    Nov 24 2025
    For years, there was a formula for raising money from VC's: perfect your pitch deck, polish your twelve slides, practice the elevator pitch, and hope someone in the limited VC circle gives you a shot. But that formula worked in a different era, when venture capital was still a close knit club and the same 1,200 people decided which ideas got funded. Those limited rules don't apply anymore. And this shift is not only relevant in VC but also when pitching angel investors. What Robert Harary has lived firsthand is that the investors who matter today aren't looking for perfect companies. They're looking for founders who are honest, self-aware, and willing to build in the open. The people who win now aren't necessarily the most connected; they're the ones who are real, transparent, and building relationships instead of performances. Robert's story is a perfect example of that shift. He raised his first million at 17 with zero network, went on to back more than 300 startups as a VC, and is now building Raisi.ai, a platform that automatically connects founders and investors, no warm intros required. In this conversation, we talk about why the old "pitch-only based" era of fundraising is over, what he sees as a new partnership-driven model, and how authenticity has quietly replaced access as the most valuable currency in venture capital. Topics Covered; Why the old fundraising playbook stopped working, and what replaced it How to raise capital without a network, connections, or pedigree What investors now value most in founders (and why "perfect" is a red flag) How to shift from perfect pitch-based to partnership-based fundraising The rise of platforms like Raisi.ai and what they signal about the future of venture How transparency and imperfection can actually strengthen investor trust What the post-2021 "venture reset" means for early-stage founders How founders can build investor relationships months before raising a round The subtle red flags that turn investors off before a single slide is shown Guest Bio Robert Harary is an early-stage VC investor, founder, and lifelong believer that access to capital shouldn't depend on who you know. He found his first deal while sitting in high school detention and has spent the decade since working to make fundraising more transparent, efficient, and equitable. Today, Robert is the #2 at Evolution VC Partners, a leading firm with 300+ portfolio companies in the Culture Tech space. Robert co-founded Raisi, a platform that automatically connects founders and investors, matching great ideas with the right capital every eight minutes. Raisi is built on a simple belief: founders shouldn't have to rely on elite networks or endless introductions to get funded. The company is redefining how startups raise money by making investor access smarter, faster, and more inclusive. Collectively, the companies Robert has worked with have raised more than $1.2 billion from firms like Sequoia, a16z, Accel, YC, and Village Global. Sign up for https://raisi.ai/ and mention The Seed Money Podcast to get a discount. Connect with Robert on LinkedIn. About Your Host Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality! Connect: Website: https://seedmoneypodcast.com/ Instagram: https://www.instagram.com/jaylasiciliano/ Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/ Please rate, follow, and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show! Disclaimer The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.
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    47 mins
  • This Non-Alcoholic Brand is Winning Investors and Defying the Beverage Odds w/ Vanessa Royle
    Oct 28 2025

    Starting a beverage brand might be one of the hardest things you can do in CPG. The margins are thin, the logistics are brutal, and most investors will tell you not to even try.

    But Harvard Business School grad Vanessa Royle and her co-founder did it anyway. They built Tilden, a ready-to-drink, premium non-alcoholic cocktail from the ground up. It all started with kitchen experiments, then they raised their first friends-and-family round with intention, and structured their seed raise to last.

    From the start, they made one simple but rare choice: to build for profitability, not hype, to grow slowly, stay intentional, and do things on their own terms.

    But that gets hard once the feedback starts rolling in. Every investor has a different take on pricing, strategy, and what success should look like. Somewhere in all those opinions, even the most confident founder can start second-guessing themselves.

    Vanessa eventually learned that sometimes, you really do know your business better than any investor. Feedback can be helpful, but it doesn't mean you have to change direction every time someone tells you to.

    So what did she figure out along the way? And what should CPG founders really look for in an investor?

    In this episode, Vanessa shares how she tuned out the noise, made the right calls for her company, her unexpected mini Shark Tank moment, and what's next for Tilden as the brand keeps growing.

    Topics Covered;

    • Why most investors discourage founders from entering the beverage industry

    • How to structure a friends-and-family round that sets you up for long-term success

    • The simple way Tilden kept their cap table clean while bringing dozens of early believers on board

    • What founders get wrong about feedback, and how to know when to trust your instincts instead

    • Why chasing growth too fast can backfire (and how profitability became Tilden's secret advantage)

    • How to prepare for a seed raise when investors keep moving the goalposts

    • What it really takes to stand out in a crowded non-alcoholic category

    Guest Bio

    Vanessa Royle is a Harvard Business School grad and co-founder of Tilden, a ready-to-drink, premium non-alcoholic cocktail that redefines how we celebrate without alcohol. After quitting drinking in 2020, Vanessa was frustrated by the lack of sophisticated non-alcoholic options. So she set out to create her own premium ready-to-drink cocktail that's low sugar. She has broken through the initial push and is currently selling in hundreds of stores. To learn more, visit https://drinktilden.com/, follow @drinktilden on Instagram. If you want to learn more about investing, send an email to vanessa@drinktilden.com.

    About Your Host

    Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!

    Connect:

    Website: https://seedmoneypodcast.com/

    Instagram: https://www.instagram.com/jaylasiciliano/

    Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/

    Please rate, follow, and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show!

    The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.

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    48 mins
  • Your Small Brand Could Win Big in CPG Right Now, Here's Why
    Oct 21 2025

    CPG products are notoriously hard to launch, fund, and get onto shelves. That's why the failure rate is so high. But what if right now is actually the best time to do it?

    The barrier to entry has never been lower, the consumer has never been easier to reach, and the path from idea to traction has never been more open.

    You can test, sell, and scale from your laptop without begging for retail space or burning through millions in capital. You can start lean, iterate fast, and build credibility through storytelling and traction. You can prove demand before you even produce at scale.

    Smaller brands are punching above their weight right now, building more influence, more loyalty, and more momentum than the legacy players. The big brands are getting squeezed, while upstarts are thriving in those small, high-end niches that used to feel impossible to break into.

    So the question isn't can small brands win; it's who's going to take advantage of this moment before the big players catch on?

    How do you make the CPG shift work in your favor? And if I were starting today, what strategy would I use to actually get funded?

    In this episode, we dig into what's really happening in the consumer product space and why niche, premium, mission-driven brands are quietly eating the big guys' lunch.

    Topics Covered;

    • Why this might secretly be the best time to launch a CPG brand

    • How small, focused brands are outpacing legacy giants

    • The smartest ways to test and build traction on a budget

    • Why "profitable and niche" beats "big and fast" every time

    • The story investors actually want to hear (and it's not about scale)

    • The mindset shift that makes entrepreneurship feel less daunting

    Startups Are Eating Big Food's Lunch

    About Your Host

    Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!

    Connect:

    Website: https://seedmoneypodcast.com/

    Instagram: https://www.instagram.com/jaylasiciliano/

    Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/

    Please rate, follow, and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show!

    The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.

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    17 mins
  • What Every CPG Founder Should Know Before Raising a Dollar w/ Debbie Wildrick
    Oct 16 2025

    When most people dream about launching a consumer product, they imagine seeing it on store shelves—but few realize what it actually takes to get there.

    The (painful) truth is, success in CPG isn't about having a great idea. It's about surviving the numbers. Most founders underestimate how much money, time, and data it really takes to earn that spot in a category. And in this business, "bootstrapping" isn't scrappy—it's risky. I've been there.

    Every year, 90% of new food and beverage products fail. Not because the products aren't good, but because they are under-resourced and lacking funding, velocity, or category dynamics.

    They try to scale too fast, too wide, or without enough proof. They don't know what it really takes to get into a retailer, or which retailers are worth going after first.

    And unlike tech, it's much harder to get an early-stage consumer brand funded. Investors want traction, not potential. They want to see that your product moves off shelves, earns repeat customers, and grows a category.

    So what do you need to know before you raise? What actually makes investors want to bet on your brand?

    In this episode, I'm joined by Debbie Wildrick, a food and beverage veteran who's spent 30 years leading brands like Tropicana and 7-Eleven. She helps entrepreneurs start small, test smart, and learn fast.

    We dig into why traction beats hype, how to prove velocity before pitching investors, and why data and storytelling go hand in hand when you're building a brand that lasts.

    Topics Covered;

    • Why 90% of new food and beverage products fail (and how to be in the 10%)

    • How to test and prove traction before raising seed money

    • The dangers of scaling too fast across multiple retailers

    • What "velocity" really means and why investors care more about it than shelf space

    • How much capital early-stage CPG brands truly need ($200K–$500K pre-revenue)

    • Friends, family, and angel rounds: how to network your way to your first investors

    • Why the path to profitability usually takes four years

    • How to use your "backyard" as the smartest first market test

    • The 10 Pillars of a Successful Company

    • Lessons from brands like Zico, Bai, and other billion-dollar exits




    Guest Bio

    Debbie Wildrick is an Executive Leader, Industry Speaker, and Sales and Distribution Expert. Widely touted as the Queen of Beverages, Debbie has been in the food and beverage industry for over 30 years. She is extremely influential, highly experienced, and a titan of the industry. Having been with 7-Eleven and responsible for making decisions that will place powerful industry-dominating brands on store shelves and move into consumers' mouths repeatedly, building store sales and profitability is invaluable. To work with Debbie, visit https://www.debbiewildrick.com/.

    About Your Host

    Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!

    Connect:

    Website: https://seedmoneypodcast.com/

    Instagram: https://www.instagram.com/jaylasiciliano/

    Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/

    Please rate, follow, and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show!

    The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.

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    44 mins