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Dear SaaStr: Why did Jason M. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups?

SaaStr

I try to work with (and invest in) CEOs that are better than me. I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done.

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What Order Should You Hire Your Management Team In?

SaaStr

IME, rough order to make hires in: VPM: $0.2m Enough to invest, but not enough to go crazy with. He asked which to hire first. If you have a few nickels in the bank, and you somehow find a great VP a half stage or even full stage early, just hire her. Hiring is so hard as it is. Make the hire now.

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Why Some VC Investments Work Out, and Some Don’t. What I’ve Learned.

SaaStr

Investments I've made that didn't work out: – Momentum investment – CEO a bit of bulls**t artist – CEO good at sales but weak product team / CTO. Investments I've made that had so-so outcomes: – CEO not better than me – CEO couldn't control burn rate – Not really SaaS.

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Dear SaaStr: What Is It Like to be Pitched by Startups as an Investor?

SaaStr

There are really three modes from a VC perspective during a fundraising pitch: You Almost immediately want to do the investment. This is 80%+ of the investments Ive done. These are also a great use of your time. The numbers are strong, but the CTO isnt good enough. They waste a ton of time. I find them torture.

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The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!

SaaStr

The Best Speakers In The World With hundreds of sessions from proven SaaS leaders who have scaled companies to significant revenue milestones, SaaStr Annual offers practical, actionable insights you won’t find elsewhere. In addition, this year Mayfield is sponsoring our VC AI Pitch Stage and will invest from $500k-$5m in the winner!

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The Reality of Selling Your Company: What No One Tells Founders with Brian Halligan, Co-Founder and Chair of HubSpot

SaaStr

Big Company M&A Is Incredibly Complex “Acquiring a company is a much bigger deal for a tech company than you think” “The soft costs are much, much more than the cash or stock” Integration can consume “10,000 hours of like expensive people’s time” 2.

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Top 10 Reasons SaaStr Annual 2025 Will Be Better Than Ever!! May 13-15 in SF Bay!

SaaStr

800+ VCs Ready to Invest This year, were bringing together over 800 VCs and investors, making SaaStr Annual 2025 the ultimate place to pitch, connect, and secure funding. Whether youre looking for a co-founder, a mentor, or your next big customer, youll find them here. Find your next VP there! Screenshot 6.