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.

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 [email protected]

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/