Day by Jay

When Power Laws Collide, Incentives Do Too

Why the same math that drives venture capital’s biggest successes also creates its greatest misalignments

Oct 24 • 

Jackie DiMonte

12

9

March 2025

AI Raises a Big Question, but Legacy Industries Have Already Answered It

The key to understanding which software models will create the most value lies in the economics of traditional industries.

Mar 18 • 

Jackie DiMonte

70

6

9

June 2024

Fixing Industrial Productivity: How AI Will Revitalize Our Workforce

Understanding the role of AI in enhancing efficiency and empowering workers in the industrial sector.

Jun 11, 2024 • 

Jackie DiMonte

8

March 2024

Unlocking hidden value: How niche markets are bigger opportunities than VCs think

Ode to Procore; a case study on niche versus mass-market project management software

Mar 6, 2024 • 

Jackie DiMonte

30

5

1

November 2023

When MVPs aren't the most valuable: how to approach markets with few early adopters

Exploring early adopters and initial use cases in industrial software

Nov 8, 2023 • 

Jackie DiMonte

16

5

April 2023

The dry powder fallacy: why there is 50% less startup capital than we think

Startup fundraising will hit five-year lows in 2023

Apr 17, 2023 • 

Jackie DiMonte

19

December 2022

What proximity matters most for building vertical startups?

You can't invest in vertical-SaaS without investing in second-tier ecosystems

Dec 17, 2022 • 

Jackie DiMonte

11

3

August 2022

What happens when you over-index on momentum early

VCs should be cautious when considering early traction across front- middle- and back- office technology platforms

Aug 27, 2022 • 

Jackie DiMonte

3

April 2022

How to kick a$$ at your first job... and maybe your second

🎨Back to basics 📊 People that are good at work are good at these things 🧘‍♀️ Agency

Apr 16, 2022 • 

Jackie DiMonte

2

January 2022

You never get a second chance at a first impression

During my business school orientation at Booth, the facilitators split us into teams of a dozen.

Jan 9, 2022 • 

Jackie DiMonte

3

October 2021

The hard stuff: where volatility creates technology opportunity

Why volatile industries lag in tech—and hold the largest potential gains

Oct 10, 2021 • 

Jackie DiMonte

2

May 2021

Day by Jay #11: No more starving artists

🎨 Celebrate 📊 Creators and Capitalists 🧘‍♀️ Maybe

May 27, 2021 • 

Jackie DiMonte

3