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The “AI Slow Roll” is Killing Your SaaS, Why Existential Dread is Needed Today: The Latest 20VC with Rory, Harry + Jason

SaaStr

Skip that part if you want. But the parts after were good. But the parts after were good. DPI (Distributions to Paid-In capital) is cold, hard cash that’s actually been returned to investors. The reality check : “There’s two very different games called venture capital. in two years.

AI
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Building and Scaling an AI Company in 2025: What Top VCs Really Want to See with Zetta, Glasswing and B Capital

SaaStr

A deep dive with three leading AI investors who collectively manage billions in venture capital and have backed some of the most innovative companies in artificial intelligence. She brings over two decades of experience in technology venture capital and has been recognized as one of the Top 100 Most Influential Women in Business.

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The Latest SaaStr + 20VC: The Brutal Math of Venture Capital — What Every B2B Founder Needs to Know

SaaStr

Your VP of Engineering Now Costs $50M in Equity OpenAI’s $6.5B Top-tier engineering talent now commands equity packages that would have been unthinkable just three years ago. ." In venture capital, 20-30% of a fund typically comes from just one investment. Nobody gets fired. Here’s $2 million.

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Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)?

SaaStr

Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $5m ARR, and ideally, Sales and Marketing well before that.

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10 Things That Would Have Helped Me Go From $1m to $10m Faster with Less Stress

SaaStr

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. These are all full-time jobs by $1m ARR.

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7 Pieces of Advice Entrepreneurs Never Hear That They Need to Hear with Jason Lemkin

SaaStr

1: Don’t hire a VP (or anyone in the early days) that you aren’t 95% sure is great. Founders between a million and $250M are talking about lowering the bar for hiring because they aren’t sure if the person is great or they’re trying to fill a gap. If you aren’t meeting that many, you aren’t taking hiring seriously.

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Stop Following These 10 Terrible Pieces of SaaS Advice with SaaStr Founder Jason Lemkin (SaaStr Podcast 682)

SaaStr

You have to understand how venture capital works. No one has time to have coffee with all of those folks. 2 “Give the VP of Sales more time.” You can’t always expect a great VP of Sales to double sales in 30-60-90 days. So no, more time does not make a VP of Sales better. That often compounds.