There’s a moment in every founder’s journey where they realize they can’t do it all alone. For most, that means hiring. For our students this week, it meant meeting their new co-founder: AI.
My hot take: the value of a liberal arts education has dramatically increased for founders and startup leaders.
Why?
AI has leveled the technical playing field in the startup space resulting in a surge of new ventures led by problem-solvers and hustlers alike. The barrier to entry of technical skills like coding has fallen, which has allowed for the emergence of a new era of founders.
We’re seeing an increase in value around creativity, critical thinking, and soft skills. And who better to check those boxes than the students from schools like Wesleyan, where taking a dance class is a staple, and triple majoring feels like the new norm?
This is why we’re embracing AI tools at Wesleyan Shark Tank. Not to stifle creativity or shortcut the necessary work, but to equip our founders with an arsenal of skills that will allow them to amplify the good work they’re already doing.
Where We Are
Class kicked off with everyone sharing one win and one roadblock from the past week. Wins ranged from “I bought my first dump truck” to “We just launched our first beta after 71 builds.” Bottlenecks were equally diverse and meant to inspire students to help out others who may be in similar predicaments they once found themselves in.
From there, we had a mini session with a fellow student founder who’s connecting the dots between NESCAC investors and startups, then we spent the rest of class demoing AI tools and putting them into practice with a hands-on customer persona workshop.
Jacob Shulman, Trivium Venture Network
Jacob Shulman, a senior at Hamilton and founder of Trivium Venture Network, joined us (virtually) to share what he’s building — a platform linking liberal arts-affiliated startups with NESCAC alumni investors.
His thesis: NESCAC founders are underrated and outperforming. Over 30 NESCAC-affiliated startups have raised $1M+ in the past five years. Yet liberal arts founders consistently get less attention from traditional VC networks than their Ivy League counterparts.
A student who bet on the thesis that NESCAC founders are investable, talking to a room of students proving it. That’s the ecosystem starting to connect.
Fun fact: Both Netflix co-founders went to NESCAC schools — Marc Randolph (Hamilton ‘81) and Reed Hastings (Bowdoin ‘83).
The AI Workshop
We covered three categories of tools:
Productivity — Wispr Flow (voice-to-text), Granola (AI meeting notes), Superhuman (AI email). The basics for moving faster.
Claude — The modern-day C-suite looks something like this: Claude (CEO), Claude Code (CTO), Claude Cowork (COO).
Creative — FreePik (AI assets for marketing), Gamma (AI presentations), Replit (building software without code).
But tools are just tools. The real question is how you apply them.
One use case: Claude in browser automating spreadsheet work. We opened a file that was full of names contacted next to an empty “Email” column. Claude proceeded to pull the names of investors and links from multiple sources in other tabs into a Google Sheet. Normally tedious, manual, error-prone. With Claude, you talk through what you’re doing on screen, it builds an SOP, and then runs the task autonomously. No hands on keyboard. The computer drives itself.
Another: Gamma turning a rough business outline into a polished investor deck in 30 seconds. Not necessarily a finished product — but a starting point that would’ve taken hours to build from scratch and excellent for creating custom decks for different recipients.
The philosophy we drove home: anything in your workflow that feels tedious or repetitive should go to AI (after you understand how to do it yourself). Every time you sit down to work, ask yourself — is this something I need to do, or could AI do it better?
By the end of class, just about everyone was convinced Claude outperforms ChatGPT. Anthropic, if you’re reading this — we’re open to a sponsorship.
Customer Personas
The second half of class was about applying what we’d just learned.
Using Claude and Gemini’s deep research tools, each student built out three customer personas (Primary, Secondary, Edge Case) for their venture. Claude Cowork helped us dive deep into who our customers were, what their routines looked like, what media they consumed, their goals, aspirations, buying habits, it got deep.
Then we brought it to life. Students paired up, exchanged their new primary persona profiles, and went on a walk-and-talk around the building. Each founder had to wear the shoes of their customer persona, answering all the questions in the character they created.
Example: Sam Pohlman became Maya Chen, a 24 year old barista and niche music artist who finally found a platform to connect with her 15k followers.
When you’re deep in building a product, it’s easy to forget how your customer actually thinks. This brought everyone back to the fundamentals: know who you’re talking to before you try to sell them anything.
Coming Up
Week 3: Matthew Wheeler ‘08 joins us as our first official guest speaker. Matt founded Sports Recruits — the platform that became the go-to tool for high school athletes navigating the college recruiting process — scaled it into a category leader, and sold it to IMG Academy. He’s now CEO of Clippd.
We’ll also be diving into fundraising formats — SAFEs, convertible notes, priced rounds — and how to pick the right structure for your company at each stage.
Watch the Recap
🎥 Week 2 Episode HERE
Get Involved
🦈 Shark: Join our investor panel at the NYC event (late April)
🎤 Guest Speaker: Lead a session on your expertise
🤝 Mentor: Meet biweekly with a student founder (30 min, remote)
📈 Investor: Get connected with our founders
Interested? Email me: mastorino@wesleyan.edu
To infinity and beyond,
Michael Astorino
PS - These Substacks are 90% handwritten by myself, 10% editing and adjustments with AI.