Jacob Ossip Resume
JOAA
JOKK
Villain · 200
You · 200
Dealing… jossip@umich.edu
A♠
The main event · $100K CAD pre-seed

CleverlyAI

School throws you a lot. CleverlyAI catches it. Your courses, lectures, notes and deadlines in one workspace, and one upload to turn any of it into something you can actually study from. Raised a $100K CAD (~$72K USD) pre-seed. 100% free while we grow. Web app, iOS coming soon.

Open cleverlyai.com$100K CAD PRE-SEED RAISED
01

Material in. A course out.

Upload the slides, the PDF, the textbook chapter or the syllabus. CleverlyAI builds it into modules with lessons, key takeaways, practice questions and cue cards. Pick the depth and style you want and work through it.

ModulesLessonsPractice QsCue cards
ECON 101 · lecture_07.mp3transcribed
ch4_slides.pdf3 lessons · 24 cards
syllabus.pdf9 deadlines added
midterm_review.docxgenerating…
Capture
02

Record the lecture. Get the notes.

Press record and pay attention. You get a transcript, a clean summary, the ideas that matter, and cards ready to review before you've left the room.

Command centre
03

Know what to do next

Every class, deadline, meeting and personal event on one calendar. Upload a syllabus and the semester fills itself in.

04

Lev.E, the assistant that knows your workspace

Not a chatbot bolted on the side. Lev.E can see your classes, calendar and materials, so it answers about your stuff and does things for you.

ScheduleCalendar actionsInvites
What's on my schedule today?
ECON 101 at 10, group meeting at 2, problem set 4 due 11:59pm.
Add meeting with academic advisor tmr at 1:30pm
Added. Want a reminder an hour before?
Send @josh88 a calendar invite for lunch Tues at 12
Invite sent.
Make it stick
05

Cue cards in one click

Recall first, then reveal, then rate what you knew. Every review gets smarter about what to show you next.

Play
06

Study your cards. Or defend a kingdom.

Five modes: Classic, Tower Defense, Siege, Speed Run and Match. Play solo or host a room.

ClassicTower DefenseSiegeSpeed RunMatch
Yours
07

Make it yours

Eight themes: Sky, Pink, Dark, Mint, Yellow, Lavender, Peach and Red.

Free
$0

No paid tier

Everything is free right now. No upgrades, no card, no trial timer. We'd rather grow first.

10♥
Portfolio · About me

Where my chips are

Everything I've got chips on. Hover a card to see the raise.

About me

Toronto kid, Ann Arbor address. I went to Upper Canada College, and I'm now at the University of Michigan in the Stephen M. Ross School of Business. In between I've built two companies, led a $380K fundraiser, and spent a lot of time on a soccer field.

What holds it together: I like building things and figuring out what they're worth. That's CleverlyAI on one side, and equity research, stock pitches and a financial analyst seat at Verve on the other. Long term I'm pointed at investment banking, private equity and venture capital.

Off the clock it's poker, chess, soccer and rugby. Same idea as the rest of it: position, patience, and knowing the odds before the money goes in.

Toronto → Ann ArborRoss · BBA 2030FounderUpper Canada College$380K raised for Chai LifelineDECA / FBLA
Core position · all in

CleverlyAI

My company. I do the product, the code and the marketing. Notes, slides, textbooks and lecture recordings go in; courses, flashcards, practice tests, study games and a calendar come out. Raised a $100K CAD (~$72K USD) pre-seed. Free while we grow, live now.

  • Founder
  • Full-stack
  • Product
  • $100K CAD pre-seed
cleverlyai.com
Analyst seat

Verve Senior Living

Financial analyst on a senior living portfolio. Built the Excel analyses behind occupancy, revenue, NOI, debt and acquisitions, audited property billing against current market rates, benchmarked properties against competitors to surface pricing gaps, and redesigned the sales commission structure to push higher-priced sales.

  • Excel
  • NOI
  • Benchmarking
  • Comp design
School

Michigan

Business student at the University of Michigan. Toronto kid, Ann Arbor address.

  • Business
  • Ann Arbor
Flip the school card
Clubs

On campus

Startup and finance clubs at Michigan. Same two interests as the rest of this site.

  • Startup
  • Finance
The full sheet

Resume

Everything on this page, on one page. Education, experience, community service and the rest.

  • PDF
  • One page
Open the resume
Small position

CluelessAI

A small desktop app. Draw a box around anything on screen and get an answer. Free, macOS and Windows.

  • Desktop
  • Side project
cluelessai.ca
The game

Poker

Position, patience, and knowing the odds before you put money in. Same habits I want on the investing side. That's the shuffle on the left, click it.

  • Cash games
  • Reading the table
The game

Chess

Send a challenge.

The game

Soccer

Always down for a kick.

The game

Rugby

Same idea, more contact.

Q♦
Next hand

The other side of the table

I'm interested in investment banking, private equity and venture capital. Not there yet. So far it's equity research and stock pitches on the investing side, and building and raising for CleverlyAI on the founder side.

Investment banking

The deal work

What pulls me in: modelling, process, and getting a transaction across the line. The fundamentals everything else is built on.

M&AValuationProcess
Private equity

Buy it, build it

What pulls me in: owning the outcome. Finding the operating levers and knowing the exit before the cheque is written.

DiligenceOperationsReturns
Venture capital

Early bets

What pulls me in: backing founders before the numbers exist. I've sat on the founder side of that pitch and raised a pre-seed.

FoundersMarketsConviction
So far

Equity research and stock pitches, a financial analyst seat at Verve Senior Living, and a company I built, shipped and raised $100K CAD for. When I look at a business, I've been inside one. That's the angle I want to bring to the investing side.

J♣
School

Go Blue

Toronto kid, Ann Arbor address. Business at Michigan, building on the side, and yes the schedule is managed in CleverlyAI.

University of Michigan
Stephen M. Ross School of Business
StudyingBBA · Class of 2030
HometownToronto, Canada
On campusStartup and finance clubs
Study systemCleverlyAI, obviously
Toronto

Hometown

Canadian, for the record.

Ann Arbor

Started at Michigan

Business student. Building on the side from day one.

Clubs

Startup and finance clubs

The two things I care about, on campus.

Now

Running CleverlyAI while in school

Turns out the best way to understand the student market is to be stuck in it.

10♥
Odds board

What I'm good at

Read it like a betting line. Everything on this board is a favourite.

SkillLineConfidenceWin %
Shipping productszero to live, twice
-400
94%
Building with AILLM features, agents, tutors
-400
94%
Full-stack devweb + desktop apps
-380
93%
Productscoping, design, what to build next
-380
93%
Marketing & growthlaunch, positioning, getting students in
-350
92%
Fundraisingraised a $100K CAD pre-seed
-350
92%
Pitchingdecks, stock pitches, presenting
-400
94%
Equity researchcompany analysis, valuation, write-ups
-350
92%
Spreadsheets & analysismodels, comparisons, decisions
-380
93%
Reading the tablepoker, negotiation, risk
-350
92%
Code

The stack

What CleverlyAI runs on.

jacob@mbp ~ zsh
The full sheet

Resume

Every hand I've played, on one page. CleverlyAI, Verve, Purify Toronto, school and the rest.

Open the PDF

CleverlyAI and CluelessAI are private codebases. This is what they're built with.

TypeScriptReactNodeWeb appPDF & slide parsingAudio transcriptionFlashcard & quiz generationAI tutor (Lev.E)Study game engineMultiplayer roomsCalendar & syllabus importGoogle Calendar syncScreen capture (CluelessAI)Global hotkeysStreaming responsesExcel models
A♥
All in

Deal me in

Click any of these to reach me

Building something for students, talking investing, or a poker game. Any of those.

Toronto · Ann Arbor · © Jacob Ossip