Seed Money

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.  

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.  

Why do handshake deals in business go bad? I get it, it starts with good intentions, you're grinding to raise money, and when a friend or family member shows interest, it feels like a lifeline.  So you say yes. Sometimes that verbal commitment feels rock solid. And then a surprise cash injection seems too good to question. But this is exactly why handshake deals in business go bad: no clear expectations on either side are written down.  It happens, founders move forward based on trust, without clear terms, contracts, or accountability.  And when things go sideways (which they often do), you're left with confusion, tension, and potentially a serious mess. In this episode, I'm joined by entrepreneur, CEO of Strive 11 International, and host of The Mindset Cafe Podcast, Devan Gonzalez.  He's sharing his personal experience with handshake deals, explaining why handshake deals in business go bad, how to protect yourself, and what to do if you're already in one.   Topics Covered: How to use recap conversations to protect yourself How to formalize a handshake deal Why podcasting is a powerful networking tool for founders Mindset secrets of highly successful people  Guest Bio Devan Gonzalez is an entrepreneur, the CEO of Strive 11 International, and the host of The Mindset Cafe Podcast. Strive 11's mission is to help improve fitness enthusiasts' lives beyond their personal health and fitness. The Mindset Cafe Podcast is your go-to source for growth mindset development and overall personal development, and transformational content! Visit https://www.devangonzalez.com/ for more information.      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 ask investors what the most common mistake in seeking funding is, you might be doing it without even realizing it. That mistake? Being so focused on raising capital that you forget to keep building traction in your business. Yes, it's easy to do when you "feel" like you need the funding to get to the next step, but you cannot stop pushing ahead. It could take you 6-12 months to close the funding you need, especially at the pre-seed/seed stage, and it's extra important to get creative and continue showing real traction during this time. This "raise money now, build later" mindset can be a major red flag for investors. They want to see driven founders with great ideas, but they don't want to see you more fixated on the check than progress. So, instead of putting all your energy into capital and fundraising, make sure hitting the next milestone despite capital constraints is a top priority and point of conversation during your pitch. What other mistakes do founders make in seeking funding? What is Seed Strapping, and why is it a better strategy for founders today? Why do so many founders feel disillusioned after a successful exit? In this episode, I'm chatting with startup founder, advisor, investor, and creator of the viral Seed Strapping framework, Josh Payne. He shares common mistakes in seeking funding that keep investors like him from writing that check. Topics Covered: Seed Strapping and why it might be the best option in 2025 Why investors want a founder with skin in the game  Why prioritizing fundraising before traction is a red flag Why Josh felt disillusioned after his exit (and how he overcame it) How to balance family with running a demanding startup  Guest Bio Josh Payne is a Speaker, Advisor, Author, and General Partner at OpenSky Ventures. He invests in, advises, and builds capital-efficient, high-growth, profitable SaaS and Consumer businesses. OpenSky Ventures has invested in Levanta, Siena, Intro, Reactiv, Magic Mind, Fishwife and more. Josh is also the founder of Onward, a company that helps brands provide a premium customer experience at no cost. Connect with Josh 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!   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.

Finding an investor and getting the funding you need is a huge win, BUT it's not the whole story. There can be red flags in investor deals that founders need to watch for and navigate. The truth is: not every investor is right for you, and not every deal will favor you. Some investors might do more harm than good and even screw you over in the end. Some deals come with hidden strings, controlling terms, and long-term consequences that can derail your business. To sniff this out, you have to get good at spotting red flags in investor deals and conversations. And most importantly, always fully understand what you're signing up for. The good news is that investors with the wrong motives are often easy to spot (if you know what to look for). It comes down to what they say (or don't say) or how much control they want in exchange for their check. Sometimes, spotting a bad-fit investor or red flags in a deal is as simple as trusting your gut and listening to that little voice saying something isn't quite right. What are some immediate signs that working with an investor would be the wrong fit? How do you make sure you're not signing a deal that will screw you over in the future? In this episode, I share some warning signs to look out for when you meet with investors and questions you should ask every investor who expresses interest in your business.    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.  

As much as I avoid real life drama with all my might, I've been guilty of falling into some of these White Lotus character traps in business. Yes it's a show about people who are conflicted and struggle through their emotions and relationships (among other many things), but it actually has some solid lessons that can be valuable in the startup/fundraising process. From Belinda desperately holding onto an investor's maybe, to Saxon who wraps his whole identity up in his business. Ahem… sound familiar? There are some moments that hit close to home.  Why is it so dangerous to zero in and “hope” one investor will come through? And how do you avoid that?  In this episode, I share 2 valuable lessons that popped up watching what is arguably one of the best series on MAX. Well, that is, if you like that cringey, luxury, drama, murder, kind of 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.  

On every Shark Tank episode, one of the most intense moments is when the founder and the investors start talking valuation—how much the company's worth and how much equity the founder's willing to give up. Figuring out how much equity you should give up in a seed round is a huge decision, and with it comes some serious consequences. No wonder it's nerve-wracking, especially if you're facing it for the first time. On one hand, you want to snag that funding and land a solid investor, but on the other, you don't want to give away too much control too soon. You want to prove your business has value, but not so much that it scares off a great investor. Plus, you need just the right amount of investment to get the ball rolling, but still leave room for future funding rounds. It's gets tricky! AND… there are ways to avoid setting a valuation all together which is the best option when you're able to do so.  If you do have to set a valuation, what's the right balance? How much equity should you give up in a seed round? Can you dodge the whole valuation talk until later?   In this episode, I'm diving into how much equity you should give up in a seed round, how to settle on a valuation, and when to defer that valuation discussion till later. -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- 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/

What do Postmates, Airbnb, and Twitch all have in common? They're wildly successful startups that got a major boost by joining accelerator programs. Now, you don't need to be chasing unicorn status to benefit from an accelerator. There are countless programs out there, each with different benefits, requirements, and growth expectations—so finding the right fit for your business is key. So, why join an accelerator? The short answer: being prepared is the best way to get funded. Accelerators push you to get your ducks in a row—fast. In today's episode, I'm sharing what I've seen founders do well (and not so well) when it comes to joining and making the most out of accelerator programs. I've been through an accelerator myself, and I've mentored at several across Southern California. I can confidently say that the right accelerator, paired with real effort, can change the game for your startup. A good program should offer: Strong mentorship Access to seasoned founders and industry experts A direct line to investors Bottom line: if you're serious about growing your startup and raising money to grow, joining an accelerator might be the best decision you ever make. In this episode, you'll learn:

If you're pitching investors and you're struggling to get the response you hoped for, you might be approaching them the wrong way. Or maybe you're gearing up for a big pitch and want to avoid missteps…  There are common mistakes I see entrepreneurs make all the time, and today we're discussing the top 7 things NOT to do when pitching investors.  Some of these mistakes might seem minor, but they can make a huge difference between getting the funding you need or missing out on a valuable opportunity. Listen closely and stay tuned until the end, because these tips could save your next pitch. Remember any missteps will make you lose time, momentum and most importantly, investor interest. Taking the time to perfect your approach makes it more likely that you get your desired outcome: dollars to drive your business forward.  So what mistakes will derail your investor pitch? How do you make a great first impression and ace the due diligence process? What character trait do all investors want in an entrepreneur?  In this episode, I'm diving into how not to approach investors and sharing 7 things that will definitely sabotage your success in the pitching process.  -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- 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 it comes to getting investors to fund your early-stage startup there are some key funding mistakes you want to avoid. Many founders fail to make progress because they miss the mark at the ground floor and they lose critical momentum in those early investor discussions.  Seed stage VC's are evaluating numerous factors and some of them are surprisingly basic. From tracking financial metrics to basic paperwork, investors are looking for a founder who can clearly communicate where their company is at and the vision of what their company can be. What red flags will get your pitch deck shot down instantly? What do founders need to know before they go out looking for funding? What financial metrics are Seed Stage VC's looking for?  Today, we're hearing straight from a VC investor who evaluates tons of startups. Triet Nguyen the Principal at Render Capital shares his story and what makes a startup a compelling investment. Topics Covered; Triet's journey to becoming a Venture Capitalist (it's not the usual story)   How to de-risk your startup  What makes VCs replace a startup founder  How to build trust through transparency  -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- Guest Bio Triet Nguyen is the Principal at Render Capital. He is a former founder turned venture capitalist who focuses on investing in early-stage startups that democratize emerging technologies for legacy and traditionally underserved industries, particularly those outside the major tech hubs of New York, Boston, and San Francisco. Visit https://www.render.capital/ and email triet@render.capital.    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.  

Investors invest in progress not ideas. When an investor is evaluating hundreds - even thousands of pitch decks, this critical piece could be just the thing that makes you stand out.   An investor is more likely to fund a startup if it's poised for growth and it clearly shows in the pitch deck. That's where milestones come in - most founders miss this piece and it could be just the thing that prevents you from getting that critical follow up meeting. An investor needs to see right away that your startup is a smart investment, so your pitch deck needs to include a clear snapshot of an upward trajectory (wait let's clarify that, it needs to be an ambitious yet realistic upward trajectory). The idea is important but more important is showing what milestones will lead to an increased valuation over time.  The milestones you put on your pitch deck need to show scalability, risk reduction, and evidence of traction. In this episode, I share why milestones matter, and which milestones you need to put on your pitch deck to appeal to investors.  -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- 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 of us are starting our companies, we're laser focused on the financial goals, finding investors and getting start-up capital. Yes we might be passionate about the product, but we don't necessarily take the time to consider if this business actually aligns with our personal goals, and what we want our lives to look like.  But I've learned from experience that focusing on the business goals and not the life goals will come back to bite us later. We'll build, build, build and then once we're far down that path, we'll realize “wait a minute, this isn't what I wanted..”  What if we could avoid this from the start, and build a business that intersects with our ideal personal life from day one? It's much harder to switch gears down the road, so if we take tactical steps to figure it out on the front end, we save ourselves a lot of stress later.  How do we answer that question, if we could do anything, what would we do? How do we avoid setting business goals that will negatively impact our personal goals?  In this episode, I share the process and tactical steps that helped me figure out what I really wanted my life to look like, the strengths test I took to figure out what I'm good at, and how I built a business that works with my strengths, interests and most importantly, my life.    -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 --   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.  

Getting on an investor's radar, perfecting your pitch, and ticking all the boxes to get funded feels like a tall order for early stage founders. You need to have a story that cuts through the noise of thousands of other startups. You need to build a network of potential investors who align with your business and industry. You need a competitive pitch that wows investors. Because there's so much involved in getting funded, the earlier you can plan your approach, the better. It's never too early to start looking at who can fund you and nailing your pitch…but where do you even begin? For a startup founder, it can be hard to figure out which facet of getting funded comes first. That's where Foundersuite comes in. This platform pulls all the resources you need into one place, and makes each step of the fundraising process more efficient. In this episode, I'm joined by the founder and CEO of Foundersuite, Nathan Beckord. After raising $21 billion for other entrepreneurs, he knows a lot about what it takes to get funded. Nathan shares strategies and hacks that will help you get funding faster. Topics Covered; The current state of startup fundraising  How to pitch your startup via Zoom  Why you need to have a teaser pitch  How to get funded before you even pitch -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- Guest Bio Nathan Beckord is an entrepreneur, CEO of Foundersuite and Fundingstack and host of How I Raised It. As a startup funding expert who has raised over $21 billion, Nathan has helped startups, VCs, and advisors raise capital faster. Visit https://foundersuite.com/ for more information, and listen to the podcast on your platform of choice.    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/ 

If you're a startup founder, the last thing you need is a dumpster fire of a digital workplace. You can't find critical documents. You're missing important emails.  You constantly find yourself double booked. A lack of digital organization isn't just a minor annoyance, it can really slow your business down.  How do you create a sense of digital peace and efficiency?  The Google Workspace ecosystem is a low-cost way to solve our digital chaos. Most of us are familiar with the Google Tools that we use in our day-to-day lives, but we might not realize all the things Google can do for our startups.  What are some Google tools that help entrepreneurs run their businesses efficiently? In this episode, I'm joined by Google Tools guru, Adrienne Farrow. She shares how to use Google to save precious time in our businesses.   Topics Covered; How to set up your email for maximum efficiency  The power of Google Workspace  How to use Google Slides for pitch decks  -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- Guest Bio Adrienne Farrow is a Google Specialist, Digital CEO and Digital Product Specialist. She is passionate about helping entrepreneurs and online business owners leverage technology to work smarter, not harder. Adrienne believes that with the right systems and knowledge, you can transform your Google Workspace from a digital jungle into a productivity powerhouse. Her mission is to ensure that you're not just working in your business, but letting your business work for you. Adrienne is here to help you systematize, optimize, and innovate using Google tools, so you can focus on what truly matters – growing your business and living your best life.    Website: https://www.adriennefarrow.com/ Free Resource: https://shop.adriennefarrow.com/drivehacks/    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.  

Running a startup? I bet you feel like a human Swiss Army knife sometimes—doing everything from marketing to operations, while trying not to lose your mind in the process. But here's the thing: doing it all yourself? That's a fast track to burnout city. Enter: Virtual Assistants (VAs). These people can help lighten the load, but there's an art to finding the right one and making sure you're getting the most out of them. So, how do you hire the perfect VA? How do you hand off tasks without feeling like things will fall apart? And, more importantly, how do you free up your time to focus on what really matters—like scaling your business? In this episode, we're diving into how to build a killer virtual team that's got your back. I'll break down how to figure out what tasks to delegate, where to find the best VAs, and how to get them up to speed so they're basically running things while you do the big picture stuff. -- Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- 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.  

Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- In entrepreneurship, success isn't a straight line. Even the most successful business owners have had to deal with losses, failures and pivots along the way. Building a business from the ground up is hard. Having what it takes to keep going when it gets tough is even harder. You might struggle to raise money, have to build your business in a recession with no revenue, or have to walk away from a company you poured your heart and soul into. How do you push through these times? That's where resilience comes into play. Instead of dwelling on a loss and giving up, resilient entrepreneurs turn their biggest failures into fuel. They understand that things going wrong is actually a necessary part of the journey, and they've built up their muscle for falling down and getting back up again. How do we build our resilience as entrepreneurs? How do you avoid giving up when we face challenges? In this episode, I'm joined by an inspiring entrepreneur and speaker who knows a thing or two about resilience. John A. Brink grew up in war-torn Holland, but found his way to Canada with $25 in his pocket and built a highly successful business and today is an author, philanthropist, serial entrepreneur, motivational speaker, and competitive body builder. In this episode, he shares his story, and how we can become more resilient as business owners. Topics Covered; John's journey from war-torn Europe to Canada  Why ADHD is a superpower  The role of resilience in entrepreneurship     Guest Bio John A. Brink is a serial entrepreneur, podcast host, ADHD Advocate, mentor, speaker and America's oldest competitive bodybuilder. He commenced his lifelong forest industry career in Holland. In 1965, John arrived in Canada with $25.47 in his pocket. His vision for a prosperous new life burned brightly as he made my way to Prince George. 10 years later, John founded Brink Forest Products. The Brink Group of Companies is a portfolio of companies focusing primarily on lumber remanufacturing and real estate development. Through passion, work ethic and the right attitude, John continues to lead his company, focusing on the production of value-added wood products.  Podcast: https://www.youtube.com/c/JohnABrink Instagram: https://www.instagram.com/john.a.brink/ Book: https://johnabrink.com/book/     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 Apple Podcasts and Spotify! 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.

Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- Creating the perfect pitch deck is probably one of the biggest challenges for entrepreneurs seeking funding. Investors see thousands of pitch decks, so how do you make sure yours actually stands out and gets your point across? How do you avoid getting dinged for formatting? How do you show the numbers while also telling a story? It's A LOT to think about, but there are simple strategies you can use to craft a great pitch deck that ticks all the boxes. From the start to the end, it's important to make every single slide count. You want your pitch deck to include all the key details about your business while still making it easy for an investor to scan through. In this episode, I'm going to show you exactly how to do that with a live review of a pitch deck an entrepreneur sent to me.   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://www.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 Apple Podcasts and Spotify! 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.  

Join the wait list for my spring 2025 Get Ready to Pitch workshop where you'll get the coaching, tactics, and materials to be ready to pitch any investor! https://www.seedmoneypodcast.com/waitlist2025 -- A big part of nailing an investor pitch is making sure it's not just about numbers. Metrics matter, but investors want to feel connected to your business on an emotional level, and customer feedback is key to that. Lately, I've been noticing that a lot of pitch decks are missing this crucial piece and honestly, it could make or break your pitch. Sharing customer testimonials, reviews, or even a quick Instagram shoutout brings your business to life and shows investors how it's impacting real people. In this episode, I'll show you how to weave customer feedback into your pitch deck in a way that's short, sweet, and super effective, so you can hook investors and get that funding!   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: http://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.

One of the hardest things about pitching to investors is keeping your cool when they ask questions. It's really easy to get flustered and thrown off your game when they're hitting you with really hard questions about your business.  What if they ask you a question you don't know the answer to? How do you avoid fumbling or rambling your answers?  With the right framework and practice, you can crush any investor question and boost your credibility and get funded. How do you stay calm and professional under pressure?  In this episode, I share the framework I use to answer investor questions, how to handle the toughest questions without losing composure and the right way to answer questions.   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! Website: seedmoneypodcast.com Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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.  

The process of raising capital has so many moving pieces, even the most motivated entrepreneur can find themselves overthinking what they need to do.  The challenge is: overthinking often leads to stalling and procrastination, which then makes us lose the precious momentum we've built along the way.   Learning to push through our own overthinking is a key skill we have to develop. Whether you're stalling on reaching out to an investor, following up with someone, or finishing your pitch deck, it's really easy to find reasons not to take action.  But this is where action is needed the most.  What should we do when we find ourselves overthinking, procrastinating and stalling? In this episode, I share how I push past overthinking and take action.    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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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.  

For consumer products, packaging plays a huge role in your ability to raise money and get onto shelves. Investors and retailers are looking for traction, so you need to have packaging buttoned up before you even approach them.  But here's the challenge: great packaging is expensive, and cheap packaging is very easy to spot and can tank your marketability. Every founder wants their product to be the “best dressed” without breaking the bank, but how do you actually achieve this?  From a packaging perspective, there are a few key things you can do to make sure your product looks good, catches the eye, and stands out on shelves. From branding to form factor, there are plenty of cost-saving strategies that don't compromise on quality.  How can we use limited time offers to get some initial attention, buzz and traction? How unique should our packaging be?  In this episode, I'm joined by packaging expert and President of Global Enterprise at AE Global, Elizabeth Corbett. She shares how CPG founders can set themselves up for success from a packaging perspective.  Topics Covered; How to get your packaging dialed in before approaching investors How to make your packaging sustainable without breaking the bank Why startups should leverage limited time offers and collabs Groups/events that startup founders should join/attend    Guest Bio Elizabeth Corbett is a CPG packaging expert with 25 years of experience, startup mentor/advisor and President of Global Enterprise at AE Global. AE Global (AEG) is a custom packaging design company and supply chain solution provider servicing the Natural Products, Health & Beauty, Cannabis, and Wine & Spirits industries. AEG's innovation lab develops custom packaging products, including EZ-Lock™ and Amplify™, and CuraLeaf's Select Squeeze bottle. With sustainability as a core value, AEG launched Ocean Recovery Group, a joint venture with 4G Recycling, which collects, cleans and recycles ocean-bound plastics. Connect with Elizabeth 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: seedmoneypodcast.com Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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.  

Getting investors or bootstrapping? That's one of the hardest decisions founders have to make. On one hand, raising capital has many benefits - you have a longer runway, more resources, and more cash to hire people and pay them well. It provides enough cash to get through the competitive hurdles to bring your product to market.  But outside capital comes with strings attached and having to please others and conform your business to the expectations of investors. That's why many founders choose not to go down the path of raising money and deliberately decide to bootstrap instead.  While it means you're operating in a resource-constrained environment, you get to retain more control and flexibility in the long-run. Bootstrapping your business means you have to be scrappy and do things a little differently, but it can work.  What are the things you need to stay on top of when you're bootstrapping? Why is product validation so important? How do you determine which funding model works for you?  In this episode, I'm joined by speaker, angel investor and founder of Product Plan, Jim Semick. He shares why he chose to bootstrap instead of taking the venture capital route and how to self-fund successfully.  Topics Covered; How to stay on top of your finances in a bootstrapped business Why it's critical to validate your product first  How to hire and pay developers as a bootstrapped business  Low-cost marketing strategies that don't need a lot of capital The value of having co-founder with complementary skills The right time to bring on an outside CEO   Guest Bio Jim Semick is a Product Management Expert, speaker, leader, angel investor and founder of Product Plan. He has over 20 years of experience turning ideas into real products that customers love. Jim's passion is identifying and launching successful SaaS products using a proven market validation process. The products he has helped launch continue to generate over $1 billion of revenue annually. Today Jim writes, lectures, and coaches on entrepreneurship, product management, and career decisions. To learn more visit https://www.jimsemick.com/ and connect with him on LinkedIn.   About Your Host Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!  Connect: Website: seedmoneypodcast.com Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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.  

Should founders pay themselves? It's probably the biggest debate in the startup world. Many entrepreneurs believe sacrificing and struggling is necessary to succeed;  that we should put everything towards growth to our own detriment. Here's the truth: being in survival mode isn't the best state for a founder to be in. You can't think, be creative or strategize effectively if you're worried about covering your bills. In fact, not paying yourself could put you on the fast track to burnout. The good news: there is a way to build our businesses while setting ourselves up for financial security. From the idea we go after to the way we fund the business from day 1, we can succeed without sacrificing our own stability. Why is the concept of founders paying themselves so controversial? How do you build a business that feeds the life you want to have? In this episode, I'm joined by 3x bootstrapper, entrepreneur, and CEO of eWebinar, Melissa Kwan. We talk about why you don't have to build a business in survival mode.   Topics Covered; How to put yourself in the healthiest state as a founder  How to choose your business idea thoughtfully  The challenge with “blue sky startups”   Guest Bio Melissa Kwan is a 3x bootstrapper, entrepreneur, host of the Profit Led podcast and co-founder and CEO of eWebinar. She is a digital nomad who believes in life over work, happiness over revenue, and creative work over hard work. To learn more, visit https://ewebinar.com/ and connect with Melissa 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: seedmoneypodcast.com Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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 have a consumer product, getting picked up by a retailer is a HUGE win. There's nothing better than a stack of juicy purchase orders and a stream of customers lining up to buy what you created! But here's the challenge: there is a ton of competition for shelf space, and a lot of products clamoring for the attention of retailers. It takes a lot to get on the shelf (and stay there) but you can achieve it, even if you're in the early stage. While the ultimate goal for most entrepreneurs is that big box national retailer, getting your product picked up can get expensive fast. Luckily, there are other channels you can use to get initial momentum, validate your product and garner some early adopters.  How do you determine the right retail channel for your product? How do you build relationships with retailers and how do you pitch them? Once you get your product into a retailer how do you make sure it sells? In this episode, I share strategies for getting your product into a retailer, and the big mistakes to avoid as an early stage founder.   Topics Covered; The different channels for selling your product  Why you might want to hold off getting into a big box store  The downside of working with a distributor  What to say in a retailer pitch  How to use push and pull marketing to increase your sell-through   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

In today's competitive, capital-strapped market, getting your business funded is a lot harder than it used to be. Entrepreneurs have access to a fraction of the funding that was easily available just a few years ago. Investors want a sure thing, so founders are jumping through a lot more hoops to get capital. It's not enough to have an initial idea or a working prototype. You need to have significant traction, social proof, a reputable team, initial revenue, founder-market fit….anything to de-risk the investment. This sounds grim, but it doesn't mean you can't get an investor to write you a check, even if you're in the earlier stages. How do you make sure you still get funded in this environment? Is this financing freeze going to thaw? Why does content creation make it easier to get funded? In this episode, I'm joined by 7-time funded founder, startup advisor, Chief Strategy Officer at Startups.com, Ed Kang. He shares the challenges in the current capital-raising space, and how entrepreneurs can still get the funding they need.  Topics Covered; The EXTRA role founders must take on when capital is scarce How to give investors exactly want they're looking for How to self-fund and bootstrap while you raise capital Easy ways to build traction and gain social proof   Guest Bio Ed Kang is a 7-time funded founder, startup advisor, executive coach, author, Organization Development Consultant and Chief Strategy Officer at Startups.com. He helps aspiring founders and early and growth stage ventures with everything from launching, funding, and scaling. To learn more, visit https://www.startups.com/ and subscribe to the YouTube channel. You can also subscribe to Ed's channel.   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

Entrepreneurship is not easy, and even the most motivated entrepreneurs find themselves feeling uninspired from time to time. Instead of driving hard towards something, we find ourselves stuck in the mud, spinning our wheels and wondering how to get back into momentum. Whether you're trying to raise money or you're experiencing a lull between big projects, it's a natural part of the journey. For a lot of entrepreneurs, these plateaus can make us question if we're still on the right path. The good news is, it doesn't have to come to that. There are steps we can take to deal with the ups and downs of business and get fired up again. How do we stop spinning our wheels? How do we check back in with the goal we originally set and make sure it's still right for us? In this episode, I share 6 things I do when I start feeling unmotivated.    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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

A couple decades ago, being a startup founder meant packing up and moving to Silicon Valley. It was the only way to easily access customers, investors and advisors. Today, you can build a business from just about anywhere without sacrificing the vital resources you need to validate your idea and get funded. As a result, many entrepreneurship communities have sprouted and developed in different cities, and that includes Nebraska! The state has become reputable in the startup space, and entrepreneurs there have made meaningful inroads and gained a ton of traction. Why has there been such an uptick in people going after entrepreneurship? What are some of the key trends emerging out of Nebraska's entrepreneurship community? How do we build businesses that don't set us up for burnout later? In this episode, I'm joined by startup veteran, strategist and community builder and editor at Silicon Prairie News, Stefanie Monge. She talks about Nebraska's startup boom and why more early-stage entrepreneurs are recognizing the value of staying there.  Topics Covered; What are early stage companies doing to get funding?  The advantage of building your startup in Nebraska  Why entrepreneurship is the ultimate wealth-building opportunity How to prevent entrepreneur burnout  The danger of a “growth at all costs” mentality    Guest Bio Stefanie Monge is the editor at Silicon Prairie News. She is an Omaha native and startup veteran, strategist and community builder whose background includes 15 years collaborating with founders and startups across the globe, 12 years working for equity and access in STEM fields, 6 years as a startup advisor and board member. Stefanie is also the founder and executive producer of international leadership development retreats and conferences, including GETconf (Gender Equity in Tech Conference), Think Start Do Women's Entrepreneurship Series and Welcor Retreats. To learn more or work with Stefanie, connect with her 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: seedmoneypodcast.com Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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.  

In the world of food entrepreneurship, having a product that tastes GOOD is only the tip of the iceberg. Going from your kitchen to a store shelf comes with a ton of considerations, steps and potential snags. The margins are razor thin. Safety and stability are critical factors that can affect the viability of the product. Getting investors, retailers and co-packers on the same page can feel like trying to solve an impossible puzzle. To successfully bring your product to market, there are key things you need to have dialed in from day one. Even though the process can be challenging, it's insanely fulfilling for a passionate entrepreneur. And now is the perfect time to innovate and bring something different to the marketplace! How do you make sure you raise enough money to weather a lengthy production process? How do you deal with co-packers, investors and retailers? In this episode, I'm joined by Associate Director of the Cornell Food Venture Center, Bruno Xavier. He shares how food entrepreneurs can set themselves up for success and how they help them achieve their goals. Topics Covered; Why food entrepreneurs run out of money (and how to avoid it) How to navigate co-packers, retailers and investors  How to balance innovation with product viability   Guest Bio Bruno Xavier is the Associate Director of the Cornell Food Venture Center. A nationally-recognized food engineer and scientist, Bruno has a Ph.D in Microbiology (Cornell '08).  He is the Associate Director of the Cornell Food Venture Center, a major extension program of the Department of Food Science at Cornell University and a Scientific Fellow at the New York State Center of Excellence in Food and Agriculture. Dr. Xavier and his team develop outreach programs and extension activities to support new and established entrepreneurs, processors and farmers introducing new products into the marketplace, providing guidelines and assisting in regulatory issues to ensure the safety of food products. As a Process Authority, Dr. Xavier oversees the establishment of schedule process documentation to comply with federal and state regulatory requirements for more than 2000 products per year for companies throughout the United States. To learn more or submit your product, visit https://cals.cornell.edu/cornell-agritech/partners-institutes/cornell-food-venture-center.   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast! 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.

For an early-stage entrepreneur, strategic partnerships are a critical lifeline and launchpad for growth. They allow you to amplify your mission, gain brand awareness and get input from investors and potential customers.   In the world of purpose-driven consumer products, it can be hard to know where to find these collaborators, but it's often as simple as a cold email.   A lot of entrepreneurs are terrified to reach out to people, but what they don't realize is how many organizations are actually looking to champion what they're building.   For the founder of AGENCY Footwear, Mathew Drazic, this was the process and it led to a powerful partnership that aims to drive real change. How did Mathew create a sneaker brand for social good? What was his process for finding partners? In this episode, he talks about his journey, the story behind AGENCY and the bigger mission of his brand.    Topics Covered; -How Mathew secured the perfect strategic partnership  -How to amplify your mission and gain brand awareness -Why it's never too early to get feedback from investors   Guest Bio   Mathew Drazic is the founder and creative director of AGENCY Footwear. AGENCY Footwear was created to replace shoes activists and concerned individuals would otherwise have to buy in order to protect their feet from the overly concrete world we all navigate. The sneakers are built to support the desire to make change, starting with the brand identity. Change is hard work, so AGENCY Footwear is designed for comfort and versatility. General purpose sneakers with soft, stable platforms and all-terrain traction to conquer any obstacle activists might face. Change also comes from within, so AGENCY Footwear uses as many sustainable materials as possible and the shoes are made at leading facilities that meet or exceed the strictest fair trade, chemical handling and animal welfare standards. To learn more, visit https://agencyfootwear.com/ and follow @agencyfootwear on Instagram.   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast! 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.

So you've pitched your idea, an investor loves it and wants to give you resources to grow your business. Well done! You've just secured a big piece of making your vision a reality - and that's a huge feat.   Now it's time to close the deal and actually receive the funding you've been seeking. Remember, once you sign the dotted line and they wire the money, there's no going back, so this next part is VERY important.   Tying up the deal in a neat bow (legally and financially) can be intimidating. There are a few things you need to have dialed to set your investor relationship up for success. You have to make sure the story you told in the pitch actually matches the reality of your business. How do you avoid losing investor trust? In part 5 of the Stages of Funding, I give you a clear road map to successfully close the deal and manage the post-funding process.    Topics Covered; -The advantages of being polished and prepared -How to keep the excitement alive after the excitement of the pitch dies down -How to negotiate with clarity and confidence  -How to make the due diligence phase easier    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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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 entrepreneurs send a pitch deck to angel groups, they don't realize they have a short amount of time to grab the attention of investors.   Angel groups are evaluating hundreds of pitch decks a week, so you have as little as 2 minutes to pique their interest and make them want to respond to you.   There are some things entrepreneurs do that instantly get investors to tune out, and they are super avoidable. Founders also don't realize that these groups are also evaluating them as the face of the business. They will dig into your public profile as much as the numbers.   Well, today I'm joined by an angel group managing partner, and he shares what investors are really looking for. What are the things that will stop the investor from reading your pitch? How do you set your business up to be more appealing to angel groups?   In this episode, Seed and Series-A Stage Investor and founder of Los Angeles Venture Partners, Jonathan Myers. He shares what investors want to see before they give you any money.    Topics Covered; -What investors are truly looking for in a founder -The pros and cons of having contractors on your team -The top reasons a pitch deck grabs an investor's attention -Easy pitch deck red flags you can avoid    Guest Bio Jonathan Myers is a Seed and Series-A Stage Investor and the founder and managing partner of Los Angeles Venture Partners. LAVP is an elite community of leaders, innovators & experts investing in high growth startups in the US. They offer educational resources, networking and curated investment opportunities to our community. To learn more, go to https://la-vp.com/, send an email to jonathan@la-vp.com or get the latest updates 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: seedmoneypodcast.com Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! 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.  

Congratulations! You just found an investor who believes in you and wants to fund your business. Now comes the next hard part - structuring the deal and setting up your startup paperwork.   For early stage entrepreneurs, the step can be confusing and overwhelming, but it doesn't have to be complicated.   In fact, you can get it dialed in quickly with minimal headaches. That's if you set it up right from day 1.   The key? Being flexible, growth-friendly and accommodating future changes.   What are the two setups you can use? How do you make negotiations easier? How do you build in your option pool, and make sure you do right by the employees who believed in you early?   In this episode - part 4 of the 5 stages of funding, I talk about the components of startup paperwork and the least complicated way to set it up.   Topics Covered; -How to set up your seed funding with terms that are flexible and future-proof -Why you don't want to have a valuation too early  -SAFES vs. convertible notes  -How to get into momentum faster -How to get legal counsel without breaking the bank       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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   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.

Coming up with a brilliant business idea and sharing it with the world.   Raising money and getting investors to fund said brilliant idea.   Getting your first customers and crossing the profitability line.   These are all stops along the entrepreneurial journey. Each of them can be hard enough to make you want to throw in the towel and go back to corporate life.   Not to mention the imposter syndrome that can come with trying to start your own business. Ultimately, what will keep us going is our mindset and the relationship we have with money.   Once we get our mindset dialed in, we can push through the fear and challenges and discover what makes entrepreneurship so amazing.   What struggles do entrepreneurs face in those early stages? How do we allow ourselves to believe in a bigger money goal?   I recently sat down with leading Transformational Money Expert, Shannah Game, on her podcast, Everyone's Talkin Money.   We talk about my entrepreneurial journey, lessons I learned along the way and how to beef up your mindset for the journey of starting your own business.    Topics Covered; -Where entrepreneurs often get stuck  -Some juicy details from my own entrepreneurial journey -How your relationship with money impacts your entrepreneurial journey -The importance of taking action    Guest Bio   Shannah Game is a leading Transformational Money Expert, Mindful Money Expert, Certified Financial Planner, Trauma of Money Expert, public speaker and author. Her podcast Everyone's Talkin' Money is dedicated to helping women (& the partners who love them) heal their relationship with money and build sustainable wealth! For more information, head to https://everyonestalkinmoney.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: seedmoneypodcast.com Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast   Please rate, follow and review the podcast on Apple Podcasts and Spotify! Hearing your comments and questions helps me come up with the best topics for the show!

In order to get funding for our businesses, we have to find and pitch to investors. Sounds easier said than done, right? This is one of the most nerve wracking and challenging steps you'll take, but it is worth it.   If you put yourself there and talk to enough people, you will get the funding you need. Even if you're an introvert. Even if you hate networking. Even if you don't have a large list of contacts in your industry.   As scary as talking to hundreds of people is, this is ultimately a test of your belief in your business. If you let your passion and belief fuel you, you can push past the discomfort that comes with this process.   Pitching to an investor sounds like a tall order, so I'm going to break it down into small steps and show how easy it is to get it done.   How do you start networking and build a list of invaluable contacts? What do you need to have buttoned up before the pitch? What are the most important things you need to include in your pitch? In this episode - part 3 of my stages of funding series, I share how to present the opportunity to an investor.    Topics Covered; -Networking tips for introverts  -The kinds of events you should be attending to build your network  -Mistakes entrepreneurs make during the actual pitch  -How to maximize conversations and leverage rejections  -Prep, pitch, delivery and follow up   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

Before we can go out and raise money for our businesses, there are things we need to have dialed in. The idea, the numbers, our pitch and the investors we're going after. This stuff is critical, but THE most important thing is the relationship we have with money.   Trying to raise money without dialing in our money mindset is a recipe for burnout, disappointment and regret. Being successful at fundraising and building a sustainable business and wealth starts with doing the inner work.   If we're not valuing ourselves, we can't expect other people to. As busy entrepreneurs, we tend to put off doing the inner work, but the truth is, we'll get to our goals faster if we do it first.   How do we find the seat of our own value before we go out to raise money? Why do we need to pair deep inner work with outer preparation? In this video, Money Therapist and Entrepreneur, Jennifer Love talks about what we need to get dialed in before we raise capital.    Topics Covered; -The challenges of raising money as a female entrepreneur -Overcoming money blocks at any stage in business -How to figure out your Wealthy Why -How to get to the root of your money mindset -Why your money mindset will always control you   Guest Bio Jennifer Love is a Money Therapist and Wealth Alchemist specializing in supporting impact-focused professionals and business owners (their teams and loved ones) to live their wealthy lives. She educates on wealth as it relates wholistically to personal well-being, business, and relationships. Qualified in Organizational & Human Behavior, Economics, Communication and Conflict Resolution, Jennifer is a career long entrepreneur who has built 5 businesses from the ground up. Over the past 20+ years she has helped hundreds of leaders do the same. Jennifer knows what it takes to build a sustainable business and what it takes to build a sustainable human. Rooted in all she has seen and experienced in her life, she feels a deep calling to offer safe experiential learning environments for wholistic financial, business, and inner growth. Jennifer believes that Financial Freedom, Business Success, and Personal Fulfillment can truly co-exist. To learn more, go to https://jenniferlove.com/ and follow @thejenniferlove on Instagram.   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast  

When you know that you're an entrepreneur at heart but you're still working your W2 job, when do you jump ship? It's the age old question all aspiring business owners ask themselves.   On one hand, we can burn the boats and go all in on the business. You'll have way more time to dedicate to it and you can scale faster. Or you can get the business off the ground, build it up on the side and then quit when you've got some momentum going.    Most aspiring business owners have taken the latter approach - it's an easy way to start without pressure and test out the concept to see if it's viable. That's the approach Matt Floyd and Craig Gerulski took. For the first 3 years of their business, they worked full-time in their W2s but put a date to leave in place.   What steps did they take to prepare to leave their W2? How did they build the business with strong operations from the ground up? How can our W2 experience actually help us in business? In this episode, the founders of Stay Classy Homes talk about their journey, and how they went about walking away from their W2 jobs and going all in on their business.   Topics Covered; -The power of getting around people doing what you want to do -The mental challenge that comes with leaving a W2 -How to prepare to leave your W2  -How to find the opportunity in boring businesses and industries  -The best things about being an entrepreneur    Guest Bio Matt Floyd and Craig Gerulski are entrepreneurs and the founders of Stay Classy Homes. After staying at their first AirBnB's as guests in 2018 in Nashville and Breckenridge they quickly fell in love with this new concept of traveling like locals all around the world and creating genuine relationships along the way.  Those experiences inspired them to begin investing in Vacation Rentals while working W-2 jobs for large corporations. Matt and Craig were both passionate about reaching financial freedom through real estate investing and felt that Vacation Rentals provided the best combination of cash flow, appreciation, and tax benefits while also allowing them to visit their investments with family and friends and create lifelong memories. For more information, head to https://www.stayclassyhomes.com/.    Host Bio 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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

If you're anything like me, being an entrepreneur appeals to you because you can design the life you want and enjoy a level of freedom you can't get from a 9-5. The problem is: a lot of us build businesses that end up creating more stress and eat away at the freedom we got into it for.   Finding a business that meets your lifestyle goals is ideal. For me, right now, real estate investing and short-term rentals does that. It gives you more control over your time and a chance to build a business that fits seamlessly into your life. In fact: it has given me so much freedom, I run a business 3000 miles away from where I live (and have time to do things on the side like the Seed Money Podcast).   How did I go from the business I initially started, to a short-term rental business? How do I run a successful business from the other side of the country?   In this special episode, I was featured as a guest on Avery Carl's podcast, The Short Term Show. We talk about my entrepreneurship journey and how to run a thriving short-term rental business.   Guest Bio   Avery Carl is the Founder of The Short Term Shop. The Short Term Shop is the country's first and largest short term rental-specific real estate firm. They have offices and agents in over 20 popular vacation rental markets. The Short Term Shop (brokered by eXp), has helped over 5,000 investors buy and sell short term rentals (airbnbs) since 2017 for a total of over $3 billion in transactions, which makes it safe to say they are the most experienced Airbnb and vacation rental real estate agents in the country. The shop has been featured as a top 15 real estate sales team by Real Trends/The Wall Street Journal annually since 2020, and has been the top producing team at eXp Realty 3 years running. They have also been featured in Newsweek, The New York Times, Forbes, and Yahoo Finance.   Host Bio   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

For entrepreneurs, running fast and charging hard comes with the territory. But that could be doing nothing but running us into the ground.   A lot of the things we think are “normal” parts of building and running businesses are actually signs of burnout. So many of us are stuck in that “wired and tired” mode and we don't even know that we're well over the limits of our health.   We can only live in a state of chronic stress for so long before it turns into trauma and whirlpool of health issues. You can't create something magnificent from a place of anxiety, stress and hurriedness. If we want to build sustainable business and come up with great ideas, we have to protect our flow state.   That means putting balance at the forefront of every decision we make. What are those early indicators of burnout and what small steps can we take to make things better?   In this episode, I'm joined by clinical and holistic nutritionist, entrepreneur and TV host, Christa Orecchio. She talks about steps we can take to run ourselves like fine-tuned machines.   Topics Covered -How to prevent burnout  -A few easy actions to offset your body's stress response -What burnout does to your body  -Christa's experience selling 30% of her company to a private equity firm    Guest Bio   Christa Orecchio is a clinical and holistic nutritionist, entrepreneur and TV host. She is dedicated to helping individuals use food, soil and self-awareness as medicine so that they can heal from the root cause. Since 2005, Christa's passion has been helping people live optimally, with a focus on the role nutrition plays in overall wellbeing. In the last five years she's truly understood how childhood trauma, limiting beliefs, unhealthy mental emotional patterning and societal conditioning can be a primary root cause for myriad of health issues (because safety starts in the nervous system) and she is grateful to have been on that path myself so that she can now support others on theirs.   Christa founded and ran The Whole Journey for 18 years which started as a private practice working with over 1000 clients, then evolved into a digital online program and supplement company for the last decade, serving over 16,000 customers to heal their gut microbiome and rejuvenate their immune system, overcome systemic candida, mold, and metals, replenish their thyroid and recode their adrenals and nervous system while creating emotional mastery.   Go to https://www.christaorecchio.com/ to learn more. Take the 3-minute TAG Disorder Assessment to find out your customized protocol here.    Host Bio   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

The playbook of raising money that people used to rely on has changed a lot over the last few years. Now that the market is more competitive and the pace of innovation is so much faster, what worked a decade ago won't produce the same results today.   Some of the best practices we were taught aren't as entrepreneur-friendly as we think. A lot of founders are taught to build something massive, aim for a high valuation and raise as much money as possible, but that just might endanger the success of our exit. A lot of founders are taking an entirely different approach - choosing to stay cash flow positive, raise less capital and intentionally work within a shoestring budget.   Can a high valuation end up working against you? How do we create a great founder fit and use familiarity to get better results? Do you need to be in Silicon Valley to set your business up for success?   In this episode, I'm joined by the founder of Dataplant, Samuel Cummings. He reveals how the rules of raising money have changed, and what we should be doing right now if we want to have success.   Topics Covered; -The truth about getting that first investment  -Pitching and winning a startup competition  -Creating your value proposition and telling your story  -The future of AI    Guest Bio   Samuel Cummings is an author, data scientist and customer success professional with a passion for driving outcomes. He is the founder of Dataplant, an automated customer management platform providing post-sales teams with the insights needed to proactively engage with each of their customers like never before. As former Head of Data Science at Gainsight, he led a global team responsible for implementing predictive analytics use-cases for Customer Success Management. Samuel uses his vast experience leveraging data to help customers make better decisions and build successful hiring programs. He is passionate about entrepreneurship, technology, data science and enterprise software. For more information, head to https://www.thedataplant.com/, watch episodes of The Scope here or connect with Samuel on LinkedIn.    Host Bio 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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast  

When you build a business, you aren't just creating a product, you're also setting up a legal entity. The legal side of things can be daunting (and expensive), especially when you intend to raise capital in the near or far future.   Before you can even think of approaching investors, first-time founders have to make sure they have the legal ducks in the row, and that can be a costly exercise if done through traditional attorneys.   You could easily spend tens of thousands of dollars setting up the legal side of the business, and still get something wrong. That's where Clerky comes in. They leverage tech to bring costs down and make the process of getting your paperwork together more efficient. You could have everything set up in as little as a week and for a fraction of the cost.   How can entrepreneurs set things up right the first time and not create issues down the line? What do you have to be thinking about if you're planning on raising money?   How do you set up stock options that won't disadvantage your early employees later on? In this episode, I'm joined by co-founder of Clerky, Darby Wong. He shares how their company helps early-stage entrepreneurs get the legal side of things done, common pitfalls and startup trends.    Topics Covered -The pitfalls many first-time founders and entrepreneurs end up in -How to set yourself up to raise future rounds -How to get your stock option paperwork set-up correctly  -Startup trends (including one surprising one)   Guest Bio Darby Wong is the co-founder of Clerky, a platform that streamlines legal paperwork for startups through automated document generation and electronic signatures. With a background in computer science and a law degree from Harvard, Darby combined his expertise to address inefficiencies in early-stage startup legal processes. After practicing law at Orrick in Silicon Valley, he co-created Clerky to provide cost-effective legal solutions for early-stage entrepreneurs. Go to http://clerky.com/ to get started.    Host Bio   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

Fear is something everyone struggles with - whether you're trying to raise seed money or (believe it or not) a billionaire who has already had success. No wonder they call fear the final frontier!   We often focus on the tangible aspects of entrepreneurship, but the mental and emotional stuff play a huge role in our success. In fact, if we don't work on the intangibles, we reduce the effectiveness of the external tactics and strategies.   We talk about things like manifesting, trusting intuition, and increasing focus, but all of that is really hard to do when we're afraid. How do we overcome fear and go after what we want? How do we manifest our goals? Why is joy so critical to our success as entrepreneurs? In this episode, I'm joined by "Hollywood's Healer," Aiden Chase.   The internationally acclaimed healer, intuitive and meditation expert talks about the invisible barriers that get in the way of our success and how to clear them from our path.    Topics Covered -How to move past fear  -Techniques for increasing your focus and manifesting  -Why finding joy as an entrepreneur is critical to your success -What billionaires fear   Guest Bio Known as "Hollywood's Healer," Aiden Chase is an internationally acclaimed, third generation, healer, intuitive and meditation expert. For over a decade, he has been the secret asset of Heads of State, Royalty, Titans of Commerce, World Spiritual Leaders, Entertainment Moguls and Academy Award Winners. Embodying his unparalleled skills of energy alchemy, with multi-disciplined expertise in business, Aiden uses ancient and futuristic techniques to boost success, creating powerful results. His intuitive strategic guidance and healing has advanced his clients in the co-creation of a combined culmination of hundreds of millions of dollars, the achievement of monumental resolutions and an impassioned intention for the manifestation of an enlightened and peaceful world. Aiden lives by the knowing that love heals, protects and transforms everything. His goal is to help you to clear the way and illuminate your path for you to fulfill your wishes and dreams. You can change your life now and find the love, success and happiness you desire! Aiden has been featured in Forbes Magazine, Inc. Magazine, People Magazine, on Access Hollywood and named “Hollywood's A-list Psychic” by the Hollywood Reporter. For more information, go to aidenchase.com and follow @‌theaidenchase on Instagram.   Host Bio 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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

In the journey of starting a company, realizing that you need to raise money is par for the course. Maybe you need to test your product's viability, increase your stock, or grow your team…these steps require funding.   Venture capital is the path many entrepreneurs take, but there are actually 7 other ways to get the funding you need.   Each method has its pros and cons and suits different types of companies. Ultimately (and this is important), the filter for your decision should be your personal goals.   Depending on what you want to achieve, you might be able to get the capital you need without working with VCs. What are the different funding methods, and the pros and cons of each? How do you pick the right one for you?   In this episode, I continue my special series on The 5 Stages of Funding. This time, I'm talking about all the different funding methods that you can use.   Topics Covered; -The benefits of raising money through family and friends -Using loans and credits cards to fund your company  -Crowdfunding: why it's not as as easy at it looks  -The great thing about agent investor groups and incubators  -What you must do before choosing Venture Capital    I created a guide on the 5 Stages to Funding guide, just for you! It's a completely free download and the perfect overview if you're ready to go after the funding you need for your business. Learn about Mindset, Types of funding, How to find and pitch to investors, deal structure, and closing the deal. Download your free guide over at seedmoneypodcast.com.    Host Bio   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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

Raising money through investors is the default for growing a company, but it might not be the right move for everyone. Taking the VC route is like walking through a one-way door - once you make that decision it sets you on a specific trajectory.   That's why more entrepreneurs are being thoughtful about the decision, and even opting out of raising money the traditional way altogether. If we chase VC money without making sure it aligns with our long-term goals, we might end up building the wrong company for us. Fortunately, if we don't want VC money, there are other ways we can get the funding we need.   The team at Sundays chose family and friends funding for that early stage. How did they use a SAFE to structure this round? Why are they intentionally choosing to remain revenue-funded? In this episode, co-founder of Sundays, Ashley Chang talks about why they didn't take the stereotypical Silicon Valley route to building their business.   Topics Covered; -Why you might consider NOT raising money -How to use a SAFE as the structure to raise your seed round -How to avoid huge attorney fees -How to find a co-founder -Questions you should ask yourself before you raise money    Guest Bio Ashley Chang is the co-founder and CEO of Sundays, an executive assistant service for working parents. Before this, she spent a decade as a product leader across a wide range of tech startups – she was the first employee at ReadMe and helped lead Carta's venture capital products from $10 to $100M+ in revenue. For more information, head to https://withsundays.com/ and connect with Ashley on LinkedIn.    Host Bio 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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

The process of raising money is as much a mental one as it is a financial one. Before we start finding and pitching to investors or even structuring our deals, there's a step we can't skip, working on our mindset.   There's no sugar-coating it - getting funded is one of the hardest things you'll do. You'll get told your idea doesn't doesn't work. You'll be told no a bunch of times, and you'll face all sorts of setbacks along the way. Self-doubt will creep in and you'll run up against your own limiting beliefs all the time.   The process will wear on you - but there's good news. You can proactively build up the mental fortitude to counter everything you'll face and it will make the path to a “yes” so much smoother. If I could do it, so can you!   So what are some of the ways we can make our mindset unshakeable? How do you develop healthy coping tools for when you inevitably face setbacks? What's the hard lesson I learned about visualization? In this episode, we're kicking off a five-part series about the stages of seed funding and I'm starting with a critical part - mindset.    Get the free cheat sheet here (https://www.seedmoneypodcast.com/?r_done=1)   Topics Covered; -What makes the seed funding process so hard -The difference between constructive criticism and negativity -How to mitigate the mental health challenges entrepreneurs face -Why it's critical to carve out time for quiet reflection as a busy entrepreneur -Why we have to visualize with caution -The healthiest ways to cope with setbacks and challenges -The lessons I learned in my own journey    Host Bio 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 Instagram: @jaylasiciliano Subscribe and watch on YouTube @seedmoneypodcast

The process of building a company, getting funded and bringing a product to market isn't just data-driven. It's gut-driven too. The numbers matter, but when you're building a product without market acceptance, you have to trust your intuition and persevere when you're told it won't work.   In many ways, taking an entrepreneurial risk is a lot like taking a creative risk. You have a vision not many understand until you convince them. The journey can be lonely, and you'll question yourself all the time. Considering that our guest took Ugg public and wrote a novel for the first time, she would know how similar the journeys are.   How do you keep going when you're doing something so disruptive that no one sees the vision? What pitfalls do entrepreneurs fall into in that early funding stage? How do you learn to trust your gut?    In this episode, I'm joined by entrepreneur, leader and coach, Diana Wilson. She shares lessons from her own career journey, what it was like taking Deckers (Ugg) public and what every entrepreneur should be doing to succeed.   Guest Bio   Diana Wilson is a self-described industry agnostic, in addition to her most recent roles as CEO, Diana has held a variety of C-suite positions across a wide range of industries—from footwear to music—in roles covering all points along the strategic, financial and operational spectrum. Early career highlights include the high-intensity thrill of taking Deckers (Ugg, Hoka) public in 1993, spearheading a number of successful M & A transactions. Most recently she has completed a passion project of writing a fictional novel and launching a Substack Newsletter, Wit & Wisdom where she writes about everything from business and creativity—to health & wellness—to living a purpose-filled life. Connect with Diana on LinkedIn and subscribe to her newsletter Wit and Wisdom.    Host Bio   Jayla Siciliano, Shark Tank Entrepreneur, Real Estate Investor, MBA and experienced investor/founder in markets from consumer products to short-term rentals. If you like Alex Hormozi, Tim Ferriss, Entrepreneurs on Fire with John Lee Dumas, or you follow sharks like Barbara Corcoran, Lori Greiner or Mark Cuban (who invested in my Shark Tank pitch) you'll love this show!

Building a company, going on Shark Tank, raising $1 million dollars and working with Mark Cuban. Sounds like an entrepreneur's dream, right? Well, that's what I thought, until I walked away from it. It was the hardest decision I've ever made, but also the best one.   When you build your own company, it becomes an extension of you, so stepping away is no easy feat. But the longer I ran the business, the more I realized it wasn't right for me. Coming into a non-existent category was hard, but that wasn't the only challenge I faced.   Ultimately, I discovered that my vision for entrepreneurship and my company were two different things. Though it was tough to break it to my investors and close it down, things worked out the way they were supposed to.   What was the journey I took into the business, and what were the realizations I had along the way? How did it feel to walk away from the business just before the low alcohol market exploded? What's wrong with hustle culture? In this episode, I share why I walked away from my dream company, and important lessons any entrepreneur can take from my story.

In the path to getting funding for your idea, meeting with investors is the most important checkpoint. You only have one shot at a first impression, so the more dialed in your presentation is, the more successful you'll be.   From pitch decks to financials, there's a ton of work that goes into preparing for that face-to-face with a potential funding source. We literally can't afford to show up without having everything dialed in.   We have to condense the idea, the numbers, and the opportunity into a 12-page pitch deck and a short presentation, and that's not easy.   Luckily there's work we can do proactively to have a perfect investor pitch. Even ChatGPT can be hugely helpful in getting prepared. What are the must-have materials for an investor meeting? Why is a business plan important (even if we don't show investors)? How do you structure your business early on?   In this episode, I'm joined by Keir Dillon, an experienced entrepreneur seasoned in raising seed money. He talks about his new business venture and everything you need to do before you meet investors.   Guest Bio Keir Dillon is a former pro snowboarder and a seasoned entrepreneur. Experienced in capital raising, he was previously co-founder of a women's fashion-forward headphone company, FRENDS, and is currently managing director of OPEN Brewing. OPEN is a new beer brand, forged in Los Angeles by a tight-knit, diverse, and talented squad of longtime friends. Based on the values of empathy, artistry, free thought, and diversity –- OPEN is infusing fresh energy into the beer world, encouraging dialogue, conversations, and excellent times amongst friends.  Follow @keirdillon on Instagram and go to https://openbrewing.com/.

The best products disrupt tired categories and breathe new life into done-to-death ideas, but is it still possible? Every year, there are fewer categories to disrupt, especially in clothing-based niches. How can you compete when people can easily buy knock-offs, dupes and cheap goods all over the internet?   By going premium, identifying an emerging customer base, making something “boring” cool and building a brand around a generational shift. That's what 1620 Workwear did.   They saw how trade-work has become a lucrative and attractive field and the lack of stylish, aspirational utility apparel. They positioned their brand and marketing differently, and proved that some categories we see as oversaturated are still ripe for disruption.   How did the idea for the brand come about? Why is it resonating with the “toolbelt generation”? How did they create a minimum viable product (MVP)? How did they get funding?   In this episode, co-founder of 1620 Workwear and marketing expert, Josh Walker shares the story of the business, and why there's still room to transform tired and tried-and-tested market categories.    Guest Bio Josh Walker is a brand builder, entrepreneur, co-founder and CMO of 1620 Workwear. 1620 Workwear is a Massachusetts-based brand that produces high-quality, American-made workwear using advanced technology and domestic materials. Their durable and comfortable products include work pants, hoodies, jackets, and accessories. Josh has extensive experience and relationships in modern culture, the sporting goods industries, action sports, hook and bullet sports, outdoor, video production, broadcasting, social networking, promotions, grass root activation and retail. Connect with Josh on LinkedIn, email josh@1620usa.com and go to https://www.1620usa.com/, and follow @1620usa on Instagram.