Jackie DiMonte

Day by Jay ↗

Venture Capital & Startups

• The Series A is dead, Long live the Series A ↗ 2 Sept 2026
  Series A round sizes have quadrupled over a decade, concentrating lead investors among fewer mega-funds and creating a barbell market where mid-quality companies struggle to fundraise. Expect smaller, concentrated funds and geographic/sector specialization to exploit this gap.
• The Right Conditions 29 Jul 2026
• AI is coming for the work people like the most 7 Apr 2026
• SaaS Was Never About the Software 12 Feb 2026
• When Power Laws Collide, Incentives Do Too 24 Oct 2025
• AI Raises a Big Question, but Legacy Industries Have Already Answered It 18 Mar 2025
• Fixing Industrial Productivity: How AI Will Revitalize Our Workforce 11 Jun 2024
• Unlocking hidden value: How niche markets are bigger opportunities than VCs think 6 Mar 2024
• When MVPs aren't the most valuable: how to approach markets with few early adopters 8 Nov 2023
• The dry powder fallacy: why there is 50% less startup capital than we think 17 Apr 2023
• What proximity matters most for building vertical startups? 17 Dec 2022
• What happens when you over-index on momentum early 27 Aug 2022
• How to kick a$$ at your first job... and maybe your second 16 Apr 2022
• You never get a second chance at a first impression 9 Jan 2022
• Day by Jay #12: The hard stuff 10 Oct 2021
• Day by Jay #11: No more starving artists 27 May 2021
• Day by Jay #10: Seeding the exception 21 Mar 2021
• Day by Jay #9: We live on the slippery slope 16 Jan 2021

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