Seed Money

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 seasoned investors what the common mistakes in seeking funding are, chances are you're making at least one of them — maybe 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 are the other common mistakes 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.

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: 💡 How to find the right accelerator program 📈 What you can expect to gain ⚠️ What mistakes to avoid 💥 And how to truly maximize your experience

About Your Host

Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast where she's on a mission to help early-stage entrepreneurs turn their ideas into reality!

Connect:

Website: https://seedmoneypodcast.com/

Instagram: https://www.instagram.com/jaylasiciliano/

Subscribe and watch on YouTube https://www.youtube.com/@seedmoneypodcast/

Please rate, follow and review the podcast on https://podcasts.apple.com/us/podcast/seed-money/id1740815877 and https://open.spotify.com/show/0VkQECosb1spTFsUhu6uFY?si=5417351fb73a4ea1/! Hearing your comments and questions helps me come up with the best topics for the show!

The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.

If you're 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.

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

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 [email protected].

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.

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.

Strengths Finder Test

Dan Negroni

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.