Triangle Startup Venture Funding, Valuations & Deal Terms

In this special solo episode of Triangle Tweener Talks, Scot goes beyond the two-part Tweener Times report to walk founders through what the data actually means in practice. This episode exists for one reason: to give Triangle founders clearer goalposts, better context, and fewer surprises when they sit down to raise capital.

Tune in to hear:

• How founders can self-service fundraising expectations using real Triangle data
• The most common caps, discounts, and raise sizes at each stage
• Why $1M ARR is a major valuation inflection point
• SAFE vs convertible note vs priced round, when each actually makes sense
• What investors look for at Seed vs Series A (and why many founders get stuck)
• How founder-market fit and AI trends skew early valuations
• Why Triangle companies often raise less, and why that’s a strength

Where to read each part:
Part 1: https://www.tweenertimes.com/p/part-iii-triangle-startup-venture
Part 2: https://www.tweenertimes.com/p/part-iiii-the-triangles-first-and

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
00:00 – 03:00 Why this data exists & the founder questions it answers

03:00 – 07:00 How the Tweener Fund dataset was built (and anonymized)

07:00 – 15:00 The origin of the Tweener List and index strategy

15:00 – 22:00 How funding stages are defined by company progress

22:00 – 35:00 SAFEs, convertible notes, priced rounds — explained

35:00 – 45:00 How deal structures change from Pre-Seed to Series A

45:00 – 59:00 Valuations, raises, and dilution by stage

59:00 – 1:07:00 What founders should actually do with this data

If this is your first time really digging into venture fundraising, you’ll hear a few terms that investors use casually but aren’t always obvious. Here’s a quick guide to the most common ones we reference in this episode:

• Pre-Seed: The earliest stage of venture funding. Often used to fund initial product development, early customer discovery, or getting to a first version of product-market fit. Rounds are typically smaller and more founder-bet driven.
• Seed: The stage where a company has early traction and is working to prove repeatability. Investors expect evidence that customers want the product, not just that it can be built.
• Series A: A growth-oriented round where the question shifts from “Does this work?” to “Can this scale?” Metrics, revenue quality, and go-to-market execution matter much more here.
• Valuation: The implied value of your company during a fundraise. In early stages, this is often based more on progress, team, and market than on traditional financial metrics.
• Pre-Money vs. Post-Money
  • Pre-money: Your company’s valuation before new capital is invested
  • Post-money: Your valuation after the new money comes in
    This distinction matters a lot for understanding dilution.
• Dilution: The percentage of ownership founders give up when they raise capital. More money or a higher valuation doesn’t always mean less dilution — structure matters.
• SAFE (Simple Agreement for Future Equity): A popular early-stage investment instrument that delays setting a valuation until a future priced round. Simple in theory, nuanced in practice.
• Convertible Note: A loan that converts into equity later, usually at a discount or valuation cap. Older than SAFEs and still common, especially with certain investors.
• Valuation Cap: The maximum valuation at which an investor’s SAFE or note will convert. Lower caps are better for investors; higher caps are better for founders.
• Discount: A percentage reduction applied to a future valuation to reward early investors when their investment converts.
• Priced Round: A funding round where the valuation is explicitly set and equity is issued immediately. More complex, but often clearer once companies reach later stages.
• Progress-Driven Investing: