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: Scot’s way of describing how early-stage investors price risk: capital is deployed based on company progress (traction, learning, momentum), not perfection.
• Founder-Market Fit: How well a founder’s background, experience, and insight align with the problem they’re solving. This often plays an outsized role in very early valuations.

---

This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.

We couldn’t share posts like this without our amazing sponsors:

Gold Sponsors:

• Balentine: https://www.balentine.com/triangle-entrepreneurs
• EisnerAmpner: https://www.eisneramper.com
• Robinson Bradshaw: https://www.robinsonbradshaw.com

Silver Sponsors:

• Automated Consulting Group: https://automated.co
• Bank of America: https://business.bofa.com/en-us/content/technology-industry-group.html

2025 Sponsors:

• Extensis HR: http://www.extensishr.com/

------
Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/