Jess Bellissimo

Operator & builder. Ex-COO (legal services), ex-CEO (franchise restoration). Building systems that create leverage. Interested in hard problems.

[Jess Bellissimo @bellissimojt]

@John_Fanta He has 2 Gold Medals (U18 and U19 and 1 MVP).

[Jess Bellissimo @bellissimojt]

@breezwoods @realsigridjin Just listened - the domain expertise point hit home. Back in January, I started building a permit tool focused on NYC Permits. Would love to compare notes.

https://t.co/auMWLSRNY3

[Michael Davidson @mike_revenue]

I helped raise a company from $493K to $1.6M in valuation, spending 70 hours building a $35M AI operations system for them.

The founder was working 58 hours weekly before he came to me

But now is down to 25 hour weeks. ~zero time in delivery. 
( Profit margin also increased from 22% to 35% too )

> The founder was personally involved in 83% (exact % btw) of revenue. 

> 7 employees and most decisions still found their way escalating to him
> couldn't take a weekend off without his phone blowing up

we mapped every function in his business. what's actually keeping clients vs what's just keeping him busy.

69% of the operation was DRAG. reporting. project setup. invoice follow-ups. QA reviews. status calls. onboarding ran from memory every time. Scattered client data across multiple softwares.

so we stripped it all and here’s what we built to replace it:

> custom dashboard replaced him checking 6 tools every morning.
> AI agents took over reporting, proposals, and client updates.
> decision frameworks so the team stops asking him every question.
> QA system so he's not reviewing every deliverable.
> onboarding automated with material collection and client context immediately ingested Day 1.

The result:

> decrease his work load from 58 hours to 25 hour weeks. ~zero time in delivery.
> profit margin raised from 22% to 35%.
> valuation increase from $493K to $1.6M. (proprietary data set, owned software infrastructure, new revenue channel via system installation fees)

same clients, smaller team, same revenue. 

Now that his time is freed up , he’s taking on double the number of clients with this NEW AI architecture.

If you want me to do the same for you,

I’m giving away all of these for free: (today only)

1. How this $35M AI operations system works

2. Full Aerodynamics Audit — 75-question diagnostic that scores your business 0-100 on founder dependency, function maturity, systems infrastructure, revenue health, and AI readiness. Takes 60 minutes. You'll know your exact drag percentage down to the hour.

3. Drag Map — function-by-function breakdown showing which of your 10+ core business functions are load-bearing vs. drag, rated 1-5 on maturity. Most founders discover 60-85% of their hours are drag.

4. Financial Impact Report — what your drag costs you per month in dollars, what your valuation looks like with vs. without systems, and the margin unlock if you strip it.

5. Build Sequence — the exact order to systematize your operations so nothing breaks. Which function first, which stays human, what gets built in week 1 vs. week 2 and so on based on 30+ builds across 12 industries.

Comment "blueprint" to receive all 5 of these :)

( must follow + RT so I can DM )

[Jess Bellissimo @bellissimojt]

@mike_revenue blueprint

[Jess Bellissimo @bellissimojt]

@williamhockey @ycombinator 10/ https://t.co/SIj7enAkZJ

Great work @patrick_oshag

[Jess Bellissimo @bellissimojt]

1/
One of the best episodes I've heard this year. @williamhockey demonstrates deep thinking in a range of areas, particularly US financial infrastructure and USD positioning. A few additional thoughts on this interview and why the timing couldn't be more relevant. 🧵

[Patrick OShaughnessy @patrick_oshag]

.@williamhockey is one of the least visible founders in tech relative to what he has created.

He co-founded Plaid and is now building Column, a software company that owns a bank, and powers Ramp, Wise, Bilt, Mercury, and others. He funded it himself by borrowing against nearly everything he had in Plaid shares, and has never raised any outside capital.

His story matters because so much of the value in our industry gets created through exactly this kind of extreme personal risk. He is maniacal about being the best in the world at his thing, and has spent his entire career betting on himself and doing whatever it takes to win.

He also spends a lot of time outside the US (in places like Kinshasa) which has given him a rare perch on the power of the US dollar.

We discuss:
- Why emerging markets are often the most financially innovative
- What owning 100% of his company allows him to do that VC-backed founders cannot
- Getting margin called and nearly going bankrupt
- Why the best founders are specialists
- What it takes to be the best in the world at your thing
- How Silicon Valley's consensus culture produces consensus founders
- How the US dollar functions as an instrument of national security

Enjoy!

Timestamps:
0:00 Intro
9:19 Emerging Markets
14:03 Silicon Valley's Elite Consensus Problem
16:03 Rejecting the VC Hamster Wheel
21:45 Equity and Liquidity
26:03 Funding a Bank
29:45 The Necessity of Extreme Founder Risk
37:18 Finding Leverage
45:20 Longevity and Profitability in Banking
48:46 Matching Your Capital Structure to Your Business
51:44 The Unseen Power of the US Dollar
1:02:30 How AI Will Transform Legacy Banks
1:09:23 The Kindest Thing

[Jess Bellissimo @bellissimojt]

@williamhockey 9/ Best line of the episode.
Look at @ycombinator's request for startups list and build somewhere else.
By the time something appears there, the smart capital has already arrived.
Find the sector with the least smart people and the most money.
That's your attack surface.

[Jess Bellissimo @bellissimojt]

@Camp4 I tell everyone I know to test drive a Tesla with FSD.

In my area, they offer self-serve test drives. Book online, upload license, and unlock the car with your phone.

https://t.co/335nYyhWCv

Need that 3-row SUV, would be their bestseller.

[Jess Bellissimo @bellissimojt]

@FletchPh This is fantastic. Have you done any data analysis on the permitting process? I started something similar (giving myself a lot of credit here) with the goal of identifying permit activity, delays, etc.

[Jess Bellissimo @bellissimojt]

@patcarino Discord is what the young kids would say.

[Jess Bellissimo @bellissimojt]

@towheretobegin This is great. I tried to build one that incorporated LIRR and Metro North commute time to build a truly door to door look but too many variables.

[Jess Bellissimo @bellissimojt]

@paul_conyngham You should connect with @celinehalioua of @loyalfordogs. She’s been working on related studies for the last few years.

[Tweets from Zach Weinberg @zachweinberg]

Yet another reason we absolutely need domestic energy independence in all forms of energy. Nuclear, oil, gas, solar, whatever. We need all of the above.

We can't have military goals held back by oil prices. Whether you agree with this specific Iran fight or not (there will be a future fight). That is insane. Such a self own.