First Funders

What could you do with a free weekend and a few subscriptions to some AI tools? Probably start a billion dollar company. 

This is the reality for so many startups and tech companies that can suddenly ship projects that previously would’ve taken a couple of months (and a couple of developers) to deploy. So in a world where everyone can build, what’s the differentiator? 

Monique Woodard has a few ideas. She’s the founding partner of Cake Ventures, a fund writing checks into pre-seed and seed-stage companies at the intersection of technology and demographic shifts. 

She’s interested in how companies can stand out in a crowded, AI-driven environment, the way soft skills have transformed, and what AI means for the humans still in the loop. 

Check size: $250k – $750k

Highlights:
 • Trust is key for any company, and it’s not something that’s going to be replaced by technology any time soon. 
 • Monique is thinking more about the desk-less future of work and what AI means for the white collar workforce. 
 • The skills once labeled as “soft” are now getting rebranded into the “hard” skills that everyone needs to survive and thrive. 

  • (00:00) - Monique x Shaherose
  • (05:08) - AI at the Application Layer
  • (08:44) - Distribution and defensibility are key
  • (12:22) - Trust at the center
  • (15:15) - Investing in post-domain name companies
  • (23:44) - The state of revenue today

Creators and Guests

Host
Shaherose Charania
Partner at Unshackled Ventures | Always helping founders | Raised on Atari, MS-DOS, Bollywood & Hip Hop. 🇨🇦in 🇺🇸
Guest
Monique Woodard

What is First Funders?

How first checks get written. What it takes to earn them.

First Funders goes inside the minds of the investors who back founders before anyone else believes in them, and the founders bold enough to make that pitch.

Each episode, host Shaherose Charania, Partner at Unshackled Ventures and a 20-year veteran of the startup ecosystem, sits down with angels, pre-seed investors, and operators-turned-VCs for candid, tactical conversations. Guests include partners from First Round Capital, Accel, Precursor Ventures, Climate Capital, Hustle Fund, and beyond.

We cover how investors are building conviction in an era where AI is reshaping every sector, what they look for before traction exists, and the frameworks behind their best bets. Whether you're writing first checks or trying to earn one, this is your inside track.