Seed Money

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/   

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.  

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.  

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.  

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.  

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.  

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.  

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.

Podcasting and fundraising don't seem to have much in common until you've done both. On the surface, each looks shiny and glamorous. But behind the curtain, they're two of the hardest things to stick with, and that's why most people quit before they ever see results. What makes them work isn't polish or perfection, it's the grit to keep showing up, the systems that keep you from burning out, and the ability to let your voice evolve as you go.  Success comes not from the pitch deck or the perfect script, but from momentum built over time. After a year of podcasting, I've seen just how closely the lessons mirror the fundraising journey. Today, I'm pulling out the biggest insights, the ones that surprised me most, that every founder raising capital should hear. What metrics actually matter in both fundraising and podcasting? How do you shift from a short-term mindset to thinking of the long game?  In this episode, I share 8 lessons I've learned from podcasting and why they mirror raising money for your business.    Topics Covered: Why consistency is more important than charisma The only metric you should track at the start How to embrace progress over perfection  The underestimated role of authenticity in getting investors to lean in The sanity-saving role of systems and processes in keeping you on track Why marketing yourself matters  How your voice evolves (and why that's a good thing)     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.  

When you're getting ready to pitch investors, it's easy to get caught up in saying all the right things. You want to sound polished, credible, maybe even impressive. But in trying to be professional, you might be dialing down the one thing that matters most in the room: your passion. And I don't mean hype or over-the-top energy. I'm talking about real conviction, the kind that shows up in your voice, your body language, and the way you talk about the problem you're solving. Because at the early stage, investors aren't just investing in your business. They're investing in you. They're human, they respond to energy, and your belief gives them permission to believe, too. But here's the tricky part: your belief can get buried under performance or the "professional" tone you think you're supposed to use. So what are the small things that make your pitch lose its punch? How do you actually convey passion, without overdoing it? In this episode, I'm breaking down what it really means to pitch with passion. I'm sharing how to make sure your energy, your story, and your personal connection to the work come through clearly, confidently, and with just the right amount of fire. Topics Covered; How to bring more passion into your pitch without veering into hype Why your "professional mask" could be diluting your conviction What it really means to pitch with energy and urgency The subtle cues that make your pitch feel timid or defensive One mindset shift that instantly changes the power dynamic in any investor meeting   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.  

When you're building a company, it's tempting to obsess over tactics. What to put in your deck, who to pitch next, which lever to pull. But that's not what separates the founders who break through from the ones who burn out. It's not tactics, it's tolerance. Your tolerance for risk, rejection, ambiguity, and delayed wins is the true edge in early-stage entrepreneurship. When fundraising is slower and the pressure's higher, your ability to keep going without quick results is everything. The founders who survive and grow are the ones who can hold their nerve when things get messy or quiet. How do you determine how much risk and uncertainty you can handle? How do you overcome the fear of wasting your time? In this episode, I'm sharing 3 simple but powerful questions to help you build that tolerance muscle, shift your mindset, and keep showing up even when it feels like nothing's working. Topics Covered; Why "risk" is subjective, and how that shapes your entrepreneurial journey The two types of risk founders must weigh How surviving failure once eliminates the fear of it happening again How to lead with borrowed belief and the most important asset in a pitch The emotional cost of inaction     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.  

You're doing all you can to reach out to investors, showing up, pitching, and doing everything right, but you're still getting no's… or worse: crickets.  Like many businesses, fundraising slows down in summer.  Feeling in limbo is one of the worst feelings, and can be super discouraging. Investors are on vacation, inboxes are quiet, and momentum feels like it's evaporated.  Unfortunately, when investors leave you hanging, you start to question everything.  One of the hardest truths about early-stage fundraising is this: rejection and being in limbo are part of the deal.  It's normal to feel like you're putting in the work and not seeing results.  But there are steps we can take to stay grounded when we're not getting the feedback or traction we hoped for.  So, how do we stay mentally sharp when progress feels invisible?  In this episode, I'm sharing 8 ways to deal with rejection, silence, and the feeling of being stuck in fundraising limbo.   Topics Covered; Why not hearing back is more discouraging than a "no" How to mentally handle the summer slowdown  How to normalize rejection and slow responses  Why tracking pitch volume matters more than tracking outcomes What to do when rejection hits or you feel stalled The importance of finding your founder community Why celebrating micro-wins isn't optional, it's a mental health strategy   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.  

If you're walking investors through your pitch deck slide-by-slide. Hiding the biggest risk in your business until the very end or treating meetings like job interviews, you're making the same mistakes that keep founders stuck in the endless cycle of "we'll pass for now."    Fundraising isn't just about your traction or your vision. It's about breaking the pattern-recognition bias VCs use to filter out anything that doesn't look like their last big win.    If you want to raise serious capital, you have to show them why you're the outlier worth betting on.    Alexander Wulff has raised over $20 million (including an $8 million seed round) by doing the opposite of what founders are usually told. Today, he's building Nume, an AI CFO built to replace the spreadsheet chaos founders like you deal with every week.    Why do we need to work hard for warm intros? Does presenting our pitch deck actually work against us?    In this episode, Alexander shares what actually works when you're raising capital, especially when your model doesn't fit the mold. You'll learn how to lead with your biggest risk (instead of trying to hide it), and how to reframe the pitch deck as a teaser.   Topics Covered; How Alexander raised $20M+, including an $8M seed round The "tech plus service" strategy that scared off most VCs What 100+ failed VC pitches taught him about objection-handling Why cold outreach almost never works (and how to get warm intros fast) How to structure a pitch that starts with your biggest risk Why "average energy" founders rarely win VC money Why passion, performance, and "controlled craziness" matter more than polish Smart ways to use AI to make financial ops proactive, accurate, and founder-friendly Guest Bio   Alexander Wulff is the co-founder and CEO of ScaleUp Finance, which began as a CFO-as-a-Service platform combining technology and human expertise to help startups manage their financial operations. Today, that vision has evolved into Nume—the world's first true AI CFO, built to eliminate the spreadsheet chaos and reactive reporting that holds founders back. Alexander's entrepreneurial journey started early. He published a bestselling book at just 19 and launched his first venture at 20, turning dormant university-held patents into a funded startup. His experience spans fundraising, fintech innovation, and scaling high-growth companies, and he brings a unique mix of operational insight and bold, contrarian thinking to everything he builds. Visit https://www.scaleup.finance/ to learn more and connect with Alex 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/   

You're not "too busy" to fundraise, you just have too much on your plate.  If you keep telling yourself you'll start pitching investors "next month," but that month never comes, this episode is for you. Because let's be honest, fundraising isn't something you accidentally find time for. It's something you make time for.  And if your calendar is packed with tasks you shouldn't be doing, you'll never get the breathing room you need to raise capital. How do you shift from "I'll do it all myself" to "Who can do this so I don't have to?" In today's episode of Seed Money, I explore the overlooked reality that most founders don't talk about: how trying to do it all keeps you from doing the one thing only you can do. Dan Sullivan's game-changing book Who Not How helped me a lot, and now I'm sharing what it actually takes to free up your time (and brain) so you can raise money without burning out.   Topics Covered; How over-functioning founders sabotage their own growth Why you need to be the one pitching (and what you shouldn't be doing) How to start small: offloading just 1-2 tasks to open up bandwidth The perfectionist trap and how to escape it   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.  

There's nothing that crushes your confidence quite like staring at your bank balance and realizing you might not make your bills in a few months.  Your savings are dwindling, you've got a life to pay for, and there's still no funding in sight.  At the same time, you still have to step up, sell your vision, and pitch your startup like everything's fine.  You're not alone, so don't feel bad.  This happens to entrepreneurs everywhere, and it happened to me.  People don't talk enough about the most gut-wrenching parts of entrepreneurship: raising funding while financially hanging by a thread.  Struggling to make ends meet, sacrificing short-term stability for the long-term win.  How do you keep going when the financial pressure mounts? How do you make sure you can still pay your bills?  In this episode of Seed Money, I'm getting real about one of the hardest parts of raising capital and how to keep walking the tightrope between chasing your vision and paying for your life.   Topics Covered; Focus on the outcome, not the path  How to stay fundable when you're broke The Side Hustle Survival Playbook  How to reframe struggle as proof of grit   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.  

If you're in the early-stage and struggling to find the right investors and feeling lost in the startup maze, we totally get it, we've been there. It's no easy task to leave that comfortable job with big dreams but zero roadmap. When I first started my entrepreneurial journey, I had no clue how to network, who to talk to, or where to even begin building the connections that could make or break my startup. I'm guessing this sounds familiar. Even with today's abundance of startup resources, knowing where to start and who to talk to can feel overwhelming. Today's guest, Neil Bloom, lays it out to help you navigate the startup and funding landscape and how to find a village to support you on your path to getting funded. Your Guest: Neil Blum From aerospace engineering to startup investing and community building, Neil has seen what works (and what doesn't) when it comes to fostering innovation outside Silicon Valley. As CEO of Rising Tide Partners, he's helped countless founders navigate the funding landscape while building sustainable startup ecosystems. Ready to stop spinning your wheels and start building real connections? Hit play and discover how to turn your local ecosystem into your competitive advantage.   Connect with Neil Bloom Here: https://www.risingtidepartners.co/ https://interlock.capital https://www.linkedin.com/in/nealbbloom/ Have a question for future episodes? Connect with Jayla on LinkedIn https://www.linkedin.com/in/jaylasiciliano/ or email hello@seedmoneypodcast.com    

Listen as Jay reveals the strategic approach he took that led to a successful pre-seed funding round in just 4 weeks! Jay Kriner, a Shark Tank alum turned tech entrepreneur, shares his methodical 9-month strategy for building investor relationships before ever making an ask. His approach centers on authentic networking, professional preparation, and timing—spending months connecting with VCs, angel investors, and wealth management professionals on LinkedIn without revealing his funding intentions. By the time he launched his official raise, he had built a network of 1,000+ qualified connections who were already familiar with his name and progress. The result? A funding commitment within weeks of launching his campaign. Jay's story demonstrates that successful fundraising isn't about cold outreach—it's about relationship building, consistent value delivery, and strategic patience that pays off when you're ready to make your move. The episode is packed with Jay's real stories—the good, the messy, and everything in between. If you're tired of hearing the same old "perfect your pitch deck" advice and want to know how relationships actually get built before you need the money, this one's for you.   Connect with Jay and learn more about Gale Project here: Gale Project website: https://www.galeproject.com  and Linkedin: Connect with Jay on LinkedIn: https://www.linkedin.com/in/jayktx/   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/   

Want to know the hard truth? Today we have Shaun Gold, a polymath and entrepreneur with extensive experience in pitch decks and fundraising (oh and bonus, he's hilarious). He shares killer insights on the common pitfalls you'll face when making pitch decks and pitching investors to raise seed money. With plenty of humor, he talks about the importance of clarity, concise storytelling, and understanding the competitive landscape. He also shares how NOT to approach investors, giving you strategies for investor outreach and highlighting the need for genuine connections and personalized communication. The one is filled with practical advice, humor, and real-world examples, to help you improve your chances of securing funding and building a successful startup.   https://www.linkedin.com/in/shaungold/ www.shaungold.com Topics Covered: -Challenges and pitfalls of creating pitch decks -Importance of self-awareness in entrepreneurship -Common mistakes founders make in pitch decks -Effective strategies for investor outreach -The significance of concise and clear communication in pitch decks -The role of storytelling in pitching to investors -Building relationships with investors rather than treating outreach as a transaction -The necessity of tailoring pitches to specific investors -The impact of design and presentation on pitch deck effectiveness -Advice for practicing and preparing for live pitches   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: seedmoneypodcast.com  LinkedIn: https://www.linkedin.com/in/jaylasiciliano/  Subscribe and watch on YouTube @seedmoneypodcast   Timestamps: Common Pitfalls in Pitch Decks (00:02:35) Shaun discusses frequent mistakes founders make in pitch decks, emphasizing the importance of self-awareness. Effective Pitch Deck Strategies (00:09:01) Shaun outlines key elements of a successful pitch deck, including brevity and strong signals. The Reality of Fundraising (00:12:53) Shaun addresses the challenges of fundraising and the need for continuous capital in startups. The Importance of Practice (00:17:15) Shaun stresses the necessity of practicing pitch presentations to ensure clarity and confidence. Common Mistakes in Investor Outreach (00:18:02) Shaun identifies frequent errors in cold outreach to investors, emphasizing targeted and personalized communication. Investor Relationships (22:24) Stresses the importance of building relationships with investors for future opportunities. Understanding the Game (23:06) Explains the unique challenges of fundraising that founders often overlook. Designing a Pitch Deck (26:13) Discusses the importance of a presentable pitch deck without excessive focus on design. Realism in Claims (28:08) Advises against over-embellishing claims about innovation and competition. Competitive Positioning (29:06) Highlights the need for clarity in differentiating from competitors without exaggeration. Investor Expectations (33:19) Discusses the importance of being realistic and sane during investor interactions. Preparing for Fundraising (40:19) Advises founders to be ready and demonstrate traction before seeking funding. Using Open VC for Investor Connections (00:41:39) Introduction to Open VC, a platform for connecting founders with various investors. Networking Strategies for Founders (00:43:08) Advice on leveraging local startup events and online platforms for networking. Effective Communication with Investors (00:44:49) Tips on how to approach investors without overwhelming them with information. The Importance of Personalized Outreach (00:46:23) Emphasis on the need for thoughtful and researched communication when reaching out to potential investors. Navigating Investor Expectations (00:48:39) Discussion on managing investor expectations and the importance of being realistic. Building a Supportive Network (00:53:03) Insights on the value of cultivating a strong network for ongoing support and advice.

In a competitive fundraising environment, traction is everything. Investors want to see proof that people care about what you're building, and few signals are stronger than an active, engaged community. When customers gather around your product, share ideas, support each other, and drive word-of-mouth growth, you're not just building a loyal user base. You're creating an ecosystem.  And that makes your startup far more attractive to investors. A well-built community is proof of demand, trust, and staying power, three things investors look for before they write a check.  It shows that people aren't just buying your product. They believe in your mission, engage with your brand, and want to be part of what you're building. In this episode of Seed Money, we're joined by Ash Lennar, founder of Odd Circles, a cutting-edge platform that helps startups and brands build high-impact communities at scale.  Odd Circles has powered more than 300 communities worldwide, including one used by none other than Seth Godin. Ash shares how founders can use community as both a growth engine and a credibility signal, especially when fundraising isn't going to plan. Topics Covered: How Odd Circles grew to power over 300 real-world meetups The biggest mistakes founders make when pitching to investors Why bootstrapping might beat fundraising in a competitive market How to build a community even if your product isn't "community-based" What consumer brands, SaaS startups, and even food companies can learn from Ash's approach Leveraging community to generate revenue and investor traction How to grow community engagement beyond social media noise   Guest Bio Ash Lonare is a speaker, the Founder and CEO of Odd Circles, and host of The Founders Podcast. Odd Circles streamlines community and event management with world-class support, making it easier for you to monetize your events with direct payouts at a fraction of the cost. Connect with Ash 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!  

Patents, trademarks, trade secrets, and copyrights: if you're building a startup, these aren't "nice to haves," they're mission-critical. Locking down your intellectual property protects your ideas, your company, your product. And it makes your startup more attractive to investors. Whether it's your brand name, your technology, or your trade secrets, different types of IP protection help you avoid costly legal pitfalls, prevent copycats, and preserve your company's value as you scale. Too many founders wait until they've gained traction to think about IP. But that can be a costly mistake. Without the right protection in place early, you could lose rights, get hit with a cease and desist, or scare off potential investors during due diligence. In this episode, we break down the essential types of IP, what they are, why they matter, and how to make smart, early decisions to protect what you're building. I'm joined by Ray DiPerna, a veteran IP attorney with over 25 years of experience helping startups and high-growth companies protect and monetize their intellectual property. Ray shares why founders should think about their IP as early in the process as possible, and how to avoid costly mistakes. Topics Covered: What counts as IP and what investors expect to see protected The real cost (and strategy) behind patents and "patent pending" Trademark pitfalls that can derail your startup's brand How to handle IP created by employees and contractors How to monetize your IP through licensing or enforcement How to protect trade secrets, source code, branding, and more What to know about copyright for websites, images, and creative assets How to prioritize legal spend when funds are limited   Today my guest is Ray DiPerna, who is an IP attorney admitted in California and New York. The views expressed in this podcast are for informational purposes only and do not constitute legal advice. Listening to this podcast does not create an attorney-client relationship. If you need legal advice regarding a specific situation, it's always best to consult with a qualified attorney who can evaluate your specific facts and circumstances as each case is different. Ray works with clients in a variety of industries. If you're interested in learning more about IP law or his work, you can find more information at the below contact information. This communication may be considered attorney advertising under the rules of certain jurisdictions. Guest Bio Raymond DiPerna is the founder of DiPerna Law. After over two decades of representing high profile clients in their intellectual property matters at prestigious law firms, including his role as a long-time partner at a prominent IP boutique, Ray founded and transitioned his practice to the DiPerna Law Firm, P.C. This enables Ray to take on a wider variety of projects and advise his clients more cost effectively. Coming from Biglaw at Sheppard Mullin, Ray works closely with specialized counsel in other law firms to provide his clients with high quality legal services in the areas of IP, data privacy, and corporate law. More specifically, Ray advises corporate clients, startups, and individuals with regard to product development,  protection, and enforcement in the software, computer, mechanical, and electrical technologies. These technologies include the fast-growing and increasingly prominent areas of AI and machine learning. Ray's practice includes advising clients with respect to all areas of IP, including patent, trademark, trade secret, and copyright, as well as data privacy. Ray's practice also includes drafting and negotiating license, ownership, and technology transfer agreements, as well as collaboration agreements and NDAs. ​Ray has 25 years of experience in preparing and prosecuting patent applications, including utility and design patents, both domestically and internationally. Visit https://www.dipernalaw.com/ for more information, and connect with Raymond on LinkedIn.  E-mail: info@dipernalaw.com Phone: 858-987-4228    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.