Red Flags in Investor Deals: Watch Out For This Before You Say Yes
Release Date: 04/22/2025
This Is What Happens When You Don’t Pitch With Passion
Seed Money
When you’re getting ready to pitch investors, it’s easy to get caught up in saying all the right things. You want to sound polished, credible, maybe even impressive. But in trying to be professional, you might be dialing down the one thing that matters most in the room: your passion. And I don’t mean hype or over-the-top energy. I’m talking about real conviction, the kind that shows up in your voice, your body language, and the way you talk about the problem you’re solving. Because at the early stage, investors aren’t just investing in your business. They’re investing in you....
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Risk Tolerance: The #1 Skill Founders Need That No One Talks About
Seed Money
When you’re building a company, it’s tempting to obsess over tactics. What to put in your deck, who to pitch next, which lever to pull. But that’s not what separates the founders who break through from the ones who burn out. It’s not tactics, it’s tolerance. Your tolerance for risk, rejection, ambiguity, and delayed wins is the true edge in early-stage entrepreneurship. When fundraising is slower and the pressure’s higher, your ability to keep going without quick results is everything. The founders who survive and grow are the ones who can hold their nerve when things get messy or...
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8 Ways To Overcome Rejection And Being In Limbo
Seed Money
You’re doing all you can to reach out to investors, showing up, pitching, and doing everything right, but you’re still getting no’s… or worse: crickets. Like many businesses, fundraising slows down in summer. Feeling in limbo is one of the worst feelings, and can be super discouraging. Investors are on vacation, inboxes are quiet, and momentum feels like it’s evaporated. Unfortunately, when investors leave you hanging, you start to question everything. One of the hardest truths about early-stage fundraising is this: rejection and being in limbo are part of the...
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How to Raise $20M by Breaking the #1 Fundraising Rule w/ Alexander Wulff
Seed Money
If you’re walking investors through your pitch deck slide-by-slide. Hiding the biggest risk in your business until the very end or treating meetings like job interviews, you’re making the same mistakes that keep founders stuck in the endless cycle of “we’ll pass for now.” Fundraising isn’t just about your traction or your vision. It’s about breaking the pattern-recognition bias VCs use to filter out anything that doesn’t look like their last big win. If you want to raise serious capital, you have to show them why you’re the outlier worth betting...
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Find Your Who: The Real Reason You’re Too Busy to Pitch Investors
Seed Money
You’re not “too busy” to fundraise, you just have too much on your plate. If you keep telling yourself you’ll start pitching investors “next month,” but that month never comes, this episode is for you. Because let’s be honest, fundraising isn’t something you accidentally find time for. It’s something you make time for. And if your calendar is packed with tasks you shouldn’t be doing, you’ll never get the breathing room you need to raise capital. How do you shift from “I’ll do it all myself” to “Who can do this so I don’t have to?” In today’s...
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Full-Time Entrepreneurship vs. Side Hustle: Paying the Bills While You Pitch
Seed Money
There’s nothing that crushes your confidence quite like staring at your bank balance and realizing you might not make your bills in a few months. Your savings are dwindling, you’ve got a life to pay for, and there’s still no funding in sight. At the same time, you still have to step up, sell your vision, and pitch your startup like everything’s fine. You’re not alone, so don’t feel bad. This happens to entrepreneurs everywhere, and it happened to me. People don’t talk enough about the most gut-wrenching parts of entrepreneurship: raising funding...
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Building Your Startup Community: From Zero to Funded w/ Neil Bloom
Seed Money
If you're in the early-stage and struggling to find the right investors and feeling lost in the startup maze, we totally get it, we’ve been there. It's no easy task to leave that comfortable job with big dreams but zero roadmap. When I first started my entrepreneurial journey, I had no clue how to network, who to talk to, or where to even begin building the connections that could make or break my startup. I'm guessing this sounds familiar. Even with today's abundance of startup resources, knowing where to start and who to talk to can feel overwhelming. Today’s guest, Neil Bloom, lays it...
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How To Build Investor Relationships Before Asking For Money w/Jay Kriner
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...
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Don’t Be That Founder w/ Shaun Gold
Seed Money
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...
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How to Build a Community Around Your Startup w/ Ash Lonare
Seed Money
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...
info_outlineFinding 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!
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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.