How Early Funding Rounds a Shape Startup's Future

The High-Stakes Decisions Behind Early Fundraising: When to Raise, Who to Raise From, and How Much Equity to Give Up

In this episode of High Stakes, host Paige Soya sits down with Jennifer Neundorfer, Managing Partner at January Ventures, for a candid conversation about the early fundraising decisions that can make or break a startup’s future.

Together, they dig into the nuances of when to raise capital, who to take money from, and how much equity to give away and the ripple effects those choices have on company trajectory, investor fit, and founder control.

From bootstrapping to pre-seed, Jen and Paige share real examples of companies that got these calls right and others that didn’t - plus actionable guidance for founders navigating their first round.

What You’ll Learn:

• When to raise: How to know if you’re truly ready for outside capital and why raising too early can hurt more than help.
• Who to raise from: The dangers of taking the wrong investor money and how to identify the right venture partners for your business.
• How much to raise (and give up): Why founders should aim to give up no more than 25% early on, and how multiple small rounds can quietly cause major dilution.
• Real-world examples: What happens when pre-seed investors impose “weird” terms and how it can stall future fundraising.
• Investor perspective: What makes a company uninvestible from a venture firm’s point of view.