And why taking a lesser valuation might actually accelerate your growth.

Veteran entrepreneur and investor, Joe Chura, breaks down the critical questions every entrepreneur needs to answer before raising capital—and explains why even successful founders get more "nos" than you'd expect.

What you'll learn:

• Convertible notes vs SAFEs: Which is better for founders?
• Angel investors vs venture capital: How to choose the right fit
• Why investors bet on founders, not just ideas
• The "data story" framework for first-time founders with no track record
• When to actually take investment (and when to avoid it)

Real talk on valuation, dilution, time horizons, and why proving yourself matters more than your pitch deck. Whether you're bootstrapping or ready to raise, this episode reveals what investors are really thinking when they evaluate your business.

For: Startup founders, entrepreneurs seeking funding, business owners considering investment, first-time founders

Topics: Raising capital, angel investors, venture capital, convertible notes, SAFEs, startup funding, founder equity, business valuation, investor pitch

Can ChatGPT count the Rs in "strawberry"? Joe Chura tests ChatGPT, Google Gemini, and Claude AI with one simple question—and the results expose a dangerous pattern in how AI tools handle mistakes and how business leaders need to validate authority while integrating new technologies into their operations for essential gains in productivity.

If AI can confidently contradict even the Dictionary, how do we make decisions when the tools we trust are simultaneously brilliant and persuasive? The strawberry test raises an uncomfortable question: If AI confidently references sources while giving wrong information, how do you know when to trust it with financial models, spreadsheet calculations, or business decisions?

Though he built and sold two businesses for over $200 million, Joe shares how he still suffered from imposter syndrome and the Fortune 500 Boardroom moment that transformed his mindset about self-doubt, the value of experience and the actions he takes to keep learning (even from his interns).

Key Takeaways:

• Why imposter syndrome is just a story you tell yourself (not reality)
• How doing the work validates your knowledge
• The danger of overestimating others' expertise and underestimating your own
• How building blocks of experience connect backwards when you need them most
• The balance between healthy caution and crippling self-doubt