5 Ways to Ask for Money (When Asking for Money Feels Weird)

Alex Perry is the founder of Practically Speaking, a communication coaching company that helps entrepreneurs and business leaders develop confidence in their message and delivery. As a dynamic speaker, author, and coach, Alex specializes in helping founders overcome communication barriers so they can clearly articulate their vision and successfully pitch their ideas.

One of the biggest challenges in securing funding is not just having a great business idea. It is having the confidence to ask for the money to make it happen. For many founders, especially those new to fundraising, asking for capital can feel uncomfortable or even intimidating. Every successful entrepreneur has had to ask. Mastering this skill is not just important. It is essential for business growth.

Alex shares five powerful strategies to help founders overcome their discomfort and approach funding conversations with confidence. Whether you are seeking revenue-based financing, looking for investors, or working on refining your financial pitch, these insights will help you reframe your mindset, sharpen your approach, and take control of the conversation.

Let’s dive into Alex’s expert advice on how to ask for funding, even when it feels impossible.

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So, you’ve got a brilliant business idea. You’ve crunched the numbers, perfected your pitch (or at least written it on a napkin), and you know—deep in your soul—that if someone just took a chance on you, you’d knock it out of the park. But there’s one tiny problem: asking for money makes you nervous. 

If you’re not used to pitching for capital—especially if you come from a background where a million dollars sounds like Monopoly money—this part can feel really uncomfortable. But here’s the truth: every successful entrepreneur has had to ask. It’s part of the deal. 

The good news, with a little bit of effort, you can get better at it. 

Here are five ways to ask for funding, even when it feels impossible:

1. Reframe the Ask: You’re Offering an Opportunity

What: Instead of thinking, I’m begging for money, remind yourself that you’re inviting someone to invest in something amazing—you.

Why: Investors aren’t handing out charity; they’re looking for smart places to put their money. You’re giving them a shot at getting in on something great.

Impact: When you shift your mindset from, please help me to here’s why you want in, you’ll exude confidence (instead of desperation). And confidence attracts investment.

2. Know Your Numbers (And Love Them)

What: Get ridiculously comfortable with your financials—your costs, revenue projections, and exactly what that million dollars will do.

Why: If you sound unsure about your numbers, investors will assume you’re unsure about your business. But if you can rattle off your break-even point like it’s your phone number? That’s power.

Impact: Knowing your numbers makes you look like the serious entrepreneur you are—and makes it easier for investors to say yes.

3. Practice Asking for Big Money (Out Loud, to Real Humans)

What: If asking for large sums makes you sweat, practice. Say the number out loud. Role-play with a friend. 

Why: When you’re not used to saying, I need a million dollars, it can come out weird—kind of like you’re asking a question instead of making a statement. Practicing helps you sound smooth. 

Impact: The more you say it, the easier it gets. And when it feels normal for you, it feels normal for the investor.

4. Find Your Money Mantra (Seriously, It Helps)

What: Identify and rewrite any limiting beliefs you have about asking for money. Repeat something like: My business is worth investing in. Money flows to great ideas.

Why: If you grew up in a culture where talking about money was taboo, or if you’ve never seen someone like you get funded, this step is crucial.

Impact: A solid mindset helps you walk into meetings like you belong there—because you do.

5. Stop Waiting to Be Ready—Just Start Asking

What: The best way to get comfortable with asking for money? Start asking for money. Even if you don’t feel ready. 

Why: No one wakes up one day magically prepared to ask for millions. But every pitch you give, every rejection you get, and every conversation you have makes you better.

Impact: The sooner you start, the sooner you’ll land the funding you need. And trust me—you’re more ready than you think.

Final Thought: You Deserve to Be Funded

You are not a burden. You are not an inconvenience. You are a business owner with a game-changing idea. Investors need people like you. The sooner you believe that the sooner they will too.

Now, go make the ask.

Your Front Row Fan,

Alex Perry