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Finance

73 posts
David Cummings

The Backend-Loaded Nature of Startup Value Creation

Recently, I saw a headline in The Wall Street Journal that said, “$3.6 Million an Hour and Other Ways to…

Jun 6, 2026 · 2 min read
A.T. Gimbel

Should I raise money or keep bootstrapping?

Another common Office Hours question we get is should I fundraise or keep bootstrapping?

Mar 19, 2026 · 2 min read
David Cummings

15 Angel Investments and All Failures

Last week, I gave a talk at a conference. After the event, a gentleman came up to me and started…

Feb 28, 2026 · 3 min read
Kathryn O'Day

5 Money Lessons I Teach My Kids as a VC Mom!

Like I’ve said before, I’m a parenting expert 😂

Feb 24, 2026 · 6 min read
Kathryn O'Day

The Real Pros & Cons of a High Valuation

What news headlines don't tell you.

Feb 10, 2026 · 7 min read
David Cummings

Seven Reasons SaaS Valuations Are Crumbling in the Age of AI

One of the most talked-about trends right now is the rapid decline in software-as-a-service valuations. Public markets in the sector…

Feb 7, 2026 · 3 min read
David Cummings

The Real Threat to SaaS Valuations Isn’t AI—It’s a Million New Startups

Software-as-a-service valuations have been in the doldrums for several years. After the peak hype of 2020–2021 and the COVID-fueled pull-forward…

Jan 24, 2026 · 3 min read
Kathryn O'Day

Not All VCs Are Built the Same (Here’s Why)

6 major differences among investors

Nov 18, 2025 · 5 min read
David Cummings

Where to Start Evaluating an Angel Investment

Last week, a friend reached out asking for help evaluating a startup investment from the perspective of someone who hadn’t…

Nov 15, 2025 · 3 min read
David Cummings

From Grow, Grow, Grow to Grow, Margin, Burn

Last week, I had the opportunity to talk with a successful tech entrepreneur about his journey. Deep into the conversation,…

Oct 25, 2025 · 3 min read
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