About
Early stage business builder with expertise in software, data, and online media. 8 exits,…
Articles by Paolo
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When Deal Structure Replaces Diligence
When Deal Structure Replaces Diligence
You don’t need perfect information if your downside is structurally capped. Conventional wisdom in acquisitions says…
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Odds and Entrepreneurship
Odds and Entrepreneurship
My daughter’s class is receiving decisions from their college applications, which has me thinking, and talking, a lot…
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Early-Stage Investing Needs a Bridge
Early-Stage Investing Needs a Bridge
Raise your hand if you’re a limited partner in an early-stage fund and you received an update that read something like…
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For the best outcome, think of your exit process as a marathon, not a sprint.
For the best outcome, think of your exit process as a marathon, not a sprint.
Ever tried to time a stock sale to perfection? Even in perfectly liquid markets, perfect timing is nearly impossible…
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Why Brokers Don’t Like Unprofitable Companies (and What You Can Do About It)
Why Brokers Don’t Like Unprofitable Companies (and What You Can Do About It)
[Note: In this article, “broker” refers to advisors, marketplaces, platforms or anyone else that charges a percentage…
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The Great Garbage Patch of Built-to-Flip AI
The Great Garbage Patch of Built-to-Flip AI
Every now and then, a method emerges that makes it very easy to get to “a few thousand” in monthly revenue. And shortly…
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Scaling Back: Is It Worth It?
Scaling Back: Is It Worth It?
I encounter a lot of startups that haven’t uncovered enough scale to raise their next round of financing. It’s usually…
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Startup Investing Is Creating Latent Value (That I Want to Give Away)
Startup Investing Is Creating Latent Value (That I Want to Give Away)
Latent value is value that is not captured by markets. Latent value happens when the market lacks information or access.
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Here's What Happens When You Focus on Revenue Too Early (or Too Late)
Here's What Happens When You Focus on Revenue Too Early (or Too Late)
I find any sort of absolute in business can be dangerous. Bandwagons come around, founders hop on, the wagon goes into…
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Follow Your Inclinations to Viability
Follow Your Inclinations to Viability
Does this sound familiar? - Startup goes into an accelerator with an idea - Advisors descend, startup emerges with an…
Activity
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Lately, my conversations with founders are tilting toward operating longer and exiting later. I’m still cautious on the “M&A is back” narrative…
Lately, my conversations with founders are tilting toward operating longer and exiting later. I’m still cautious on the “M&A is back” narrative…
Posted by Paolo DiVincenzo
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I have been fortunate to invest in multiple unicorns, including Square, Twitter/X, Robinhood, Ripple, Coinbase, and Solana. The best all hold two…
I have been fortunate to invest in multiple unicorns, including Square, Twitter/X, Robinhood, Ripple, Coinbase, and Solana. The best all hold two…
Liked by Paolo DiVincenzo
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Eyeing an exit with your SaaS in 2026? Here is what you need to consider: "Is it a good time to exit?" That's a question I get asked in almost every…
Eyeing an exit with your SaaS in 2026? Here is what you need to consider: "Is it a good time to exit?" That's a question I get asked in almost every…
Liked by Paolo DiVincenzo
Experience
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Education
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Spanish
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More activity by Paolo
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I’m incredibly excited to share that I’ve started a new role as RVP, West at Silverpush. I’m beyond grateful for the opportunity to work with…
I’m incredibly excited to share that I’ve started a new role as RVP, West at Silverpush. I’m beyond grateful for the opportunity to work with…
Liked by Paolo DiVincenzo
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We made only $17,000 our first year at Automated Insights, trying to fund sports content off ads, but here's the question we asked that helped us…
We made only $17,000 our first year at Automated Insights, trying to fund sports content off ads, but here's the question we asked that helped us…
Liked by Paolo DiVincenzo
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I’m doubling down on the OpsAssembly experiment we ran in Q4 2025. Last October, I pulled together 24 experienced startup operators who had thrived…
I’m doubling down on the OpsAssembly experiment we ran in Q4 2025. Last October, I pulled together 24 experienced startup operators who had thrived…
Posted by Paolo DiVincenzo
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