Seed Money

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/

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: [email protected]

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.

Many founders have a killer product, a passionate team, and traction, but they don't realize that investors are really betting on THEM.

The truth is, your projections don't need to be perfect, your deck doesn't need to be perfect. But you need to do the things that most people won't do to stand out. You need to show that you are strategic, thoughtful, and aligned with your growth narrative.

In this episode, we dive into what actually matters to investors and how early-stage companies can use financial storytelling to build trust and get funded.

I'm joined by Mike Sherbakov, former Marine, serial entrepreneur, and General Partner at The Veteran Fund, an early-stage venture firm investing in founders from the military community.

We talk about how founders should approach pitching investors at the seed stage, how different industries require different metrics, and why, at the end of the day, investors are betting on the founder, not just the numbers.

Topics Covered:

• Why veterans make great founders

• How The Veteran Fund evaluates early-stage opportunities

• How to project your financials without a finance background

• Why entrepreneurship isn't for everyone (and how to know it's for you)

• Top tools and resources for startup benchmarks

Guest Bio

Mike Sherbakov is the CEO of Greatness Ventures, supporting impact-driven leaders and brands. He has led the business accelerator to thousands of investor members and hundreds of companies in their impact portfolio. Their venture philanthropy arm has built homes in underdeveloped communities since 2014 and continues to lead impact trips open for the community to join. He serves as General Partner at The Veteran Fund, a pre-seed venture capital fund in Silicon Valley, and Director of San Diego's Founder Institute, the largest early-stage startup accelerator in the world. Mike has previously founded three startups (HMS Fitness, Karuna Towels, Greatness Media), helped grow two companies from 0 to $ 20 M+ valuations (Wildfire and NurishMe), and consulted with large companies including Fitbit, lululemon athletica, Equinox, and Qualcomm. He served on active duty as a United States Marine, graduated Magna Cum Laude from San Diego State University, has traveled to 58 countries and counting, and believes that our greatness is not what we have but what we give. To learn more, visit https://veteran.fund/.

Resources

fi.co/benchmarks

https://www.linkedin.com/in/peterjameswalker/

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.