Episodes

  • 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
  • How Much Should You Really Spend on a Pitch Deck?
    Oct 7 2025

    If you're raising money, one of the first questions you'll run into is whether to DIY your pitch deck or hire someone to help. And trust me, it's not as straightforward as it sounds.

    I've wasted money on "professional" help that didn't move the needle, and I've also seen founders burn months trying to DIY when they should have just invested a little upfront.

    That's the real challenge. It's not just if you can design this yourself. It's knowing when your deck is strong enough to stand on its own.

    Here's where it gets even more confusing: the number of "pitch deck services" out there promising the world. Some quote a few hundred bucks, others want tens of thousands. And it's not always clear what you're really paying for. Are you getting strategy and feedback that sharpen your story, or just a prettier version of the same weak slides?

    In this episode, I break down the reality of pitch deck pricing. You'll learn how to figure out if you should do it yourself, what to look for in outside help, and how to avoid wasting time and money on the wrong solutions.

    Topics Covered;

    • How to tell if your deck is strong enough to DIY, or if it's time to hire

    • The red flags that your pitch isn't landing with investors

    • What freelancers, mid-level designers, and agencies actually deliver (and what they don't)

    • The real price ranges and what you should expect at each level

    • Why overspending too early can waste money, but underspending can cost you months

    • The hybrid approach that gets you professional polish without blowing your budget

    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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    21 mins
  • The Brutal Truth About Scaling Your Business (Things Will Break) w/ Josh Hatter
    Oct 1 2025

    When you're building a business that appeals to investors, you have to show that you can scale and stabilize at every level.

    But here's the thing - scaling isn't clean or painless…it's not supposed to be. It almost always means that things will break. Systems will strain, processes will collapse, and the business will feel unstable.

    This is inevitable. Growth will always stress the business.

    As a founder, your mindset shouldn't be preventing stress; it should be preparing for it.

    Every stage of growth demands that you adapt, fix what cracked under pressure, and put new structures in place that can carry you to the next level.

    And part of that structure isn't technical at all, it's human. Your inner circle has to be balanced. Too many yeses and you'll miss the weak spots. Too many nos and you'll never take the risks growth requires.

    What should early-stage founders be thinking about as they grow? How did my guest turn a $30K loan from his 401K into 20+ million in real estate and a $10M a year company?

    In this episode, I'm joined by entrepreneur, mentor, short-term rental expert, and investor, Josh Hatter.

    We unpack why scaling is supposed to feel uncomfortable, how to treat breakage as proof of progress, and why curating the right mix of voices around you might be the most important system you ever build.

    Topics Covered
    • How Josh turned a $30k 401k loan into $20M+ of real estate assets and $100M under management

    • How childhood chaos became his greatest entrepreneurial strength

    • The real reason rental arbitrage is dangerous (and what to do instead)

    • How to survive a once-in-a-lifetime industry collapse like COVID in hospitality

    • Why scaling means breaking your systems on purpose

    • The hardest balancing act in entrepreneurship

    • Why owning the real estate your business operates in is one of the smartest wealth moves you can make

    • How Josh formalized his mentorship group into a nonprofit

    Guest Bio

    Josh Hatter is a Short Term Rental (STR) and Bed & Breakfast (B&B) expert investor and entrepreneur. After working in Corporate America, Josh bet on himself to grow a $30,000 401 (k) loan to $20M+ of assets in 12 years of real estate investing through his principles of information arbitrage. He helps high achievers exit corporate America and reach financial independence through hospitality real estate. Visit https://www.joshhatter.com/, send an email to josh@joshhatter.com. To learn more about the mentorship program, visit https://keyscollective.org, and to stay at Josh's rentals, visit staycvp.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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    47 mins
  • Why Your Pitch Deck is Important (It's Not About Stuffing in Every Detail)
    Sep 17 2025

    A lot of founders go into fundraising with the wrong idea about pitch decks. They think the deck has to include everything, every detail about the product, every market stat, every bio. But that's not what a pitch deck is for.

    The real job of your deck is simple: get you to the next step. It's not supposed to win the deal on the spot. It's supposed to grab attention, tell your story clearly, and make investors want to keep talking to you.

    Think of it like a billboard. If it's cluttered or confusing, people drive right past it. If it's sharp and clear, they remember it, and that's all you need at this stage.

    When I was raising money for my first company, I didn't have connections, a big name, or a track record. What I did have was a short, clear deck that told the story simply. That's what got me meetings, credibility, and eventually, funding.

    Done right, your pitch deck shows you can communicate like a pro and makes the whole fundraising process a lot easier.

    In this episode, I break down why pitch decks really matter, what most people get wrong, and how to build one that actually gets you in the door.

    Topics Covered;

    • Why your deck should function like a billboard, not a book

    • How to tell a cohesive story that flows logically and keeps investors engaged

    • The overlooked role of timing, why investors want to know "why now?"

    • How your deck doubles as a tool to force clarity in your business thinking

    • The professionalism test: how fonts, colors, and flow influence investor trust

    • Why tweaking a deck doesn't mean adding slides

    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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    30 mins