We are in the home stretch now and the founders are getting closer to pitch-ready every session.

We wrapped up a great Week 9 —Ravid Chowdhury came in and conducted a lesson on how to build an investor relationship funnel + a fundraising workshop.

Instead of a vlog, though, we decided to put together a sizzle reel to capture the program we are building here. So I’m keeping this letter short and letting this video take the spotlight:

It’s a good time to thank our wonderful Chief Storytelling Officer, Fisher Hirsch, who has been capturing all of this incredible content.

So, if this video made you smile as much as I did or got you excited for what is to come. All we ask now is you join us for the final event!

RSVP Here

If you can’t make it in person — no worries, we’re livestreaming the entire event. Subscribe to our YouTube so you don’t miss it:

Livestream Link

And if you know someone who'd want to be in the room — an alum, an investor, a friend who's into this stuff — please forward them the RSVP. It goes a long way:)

We’ve got 3 more classes to go (and plenty more to write about). Stay tuned, next week’s class is one of our best ones yet.


With gratitude,

Michael

Sounds like a scheduling conflict, but this was all intentional. Welcome to the founder schedule — where nothing pairs well together and everything's due at the same time.

Early founders being the CEO, COO, CMO, & CFO, is not news. One of the hardest part of being a startup operator isn't any single discipline. It's the whiplash between all of them. Shooting a brand video and building a P&L require completely different parts of your brain, and usually there is no time in between. Week 8 put both on the schedule back to back — content creation first, then financial modeling with Charlie O'Connell.

Where We Are

We started with a mini workshop on founder-led content. Short-form, raw, personality-driven storytelling has the power to truly move the needle for companies. We covered the anatomy of what makes content work: a hook that earns someone’s attention in the first three seconds, the body that keeps them watching, and the call to action that converts a viewer into a follower or customer.

In today’s world, people want to see who’s behind the companies they support. Your product matters, but so does your personality, your voice, your story. For early-stage founders especially, you are the brand.

The lesson was kept short, because the whole point of this workshop was to get out of the classroom.

We gave everyone five minutes to brainstorm, and then sent them out into the wild with a simple mandate: come up with an idea, shoot it, and bring it back, in one hour.

It was a beautiful day for it. 70 degrees, campus alive, and suddenly we had ten founders scattered across Wesleyan doing completely different things: recording skits, running on-the-street interviews, shooting product demos on the baseball field, we had it all. There’s no single formula for founder content, and the exercise was about finding your own voice in it.

What matters most is that they started. Analysis paralysis kills more founder content than bad ideas ever will. Everyone has a list of video concepts they’ve been meaning to get to “when the time is right.” When in reality, you just have to press record (I say this as someone who has a running list of content ideas for Spacemilk that I still haven't touched).

Nick Dargel proved this point. He went from idea to script to filming to a fully edited video, all within the hour. Submitted the final cut before class was even over. Check it out:

When everyone regrouped, we watched what they’d shot, shared feedback, and the band-aid was off. These founders had gone from thinking about content to having content, and realizing it didn’t need to be perfect to be good.

Let’s Talk Money

We then took a total 180 with the next lesson. Charlie O’Connell joined us virtually to walk the class through building financial projections from scratch. Charlie came to last year’s cohort too, and his ability to make the financial side of startups feel accessible is why we keep bringing him back. P&L statements, EBITDA, burn rate, unit economics, the technical, unglamorous, absolutely essential side of building a business that nobody puts on their Instagram story.

A founder who can tell a compelling story but can’t walk through their numbers will hit a wall eventually. Charlie broke it down in a way that met students where they were and helped them through creating their foundational financials. Our founders are getting stronger at storytelling every week, but when they're sitting across from an investor in a few weeks, storytelling alone won't close the deal. Charlie gave them the language to back it up.

A Favor to Ask

We’re almost three weeks away from our final event where six founders from this cohort will be selected to pitch live in front of Wesleyan alumni angel investors. It’s the moment we’ve been building towards all semester and I wanted it to close out by asking you all for a favor.

The goal is to make this a flagship event for Wesleyan entrepreneurship, not only prove that Wesleyan Shark Tank is a successful medium for learning entrepreneurship through action, but also to demonstrate that we are capable of producing true problem solvers and capable, well-rounded leaders.

So, if you could take a minute to share our RSVP with someone — a friend you've been meaning to catch up with, an entrepreneur you think would enjoy it, anyone who should see what's happening here — it goes a long way. Filling that room is what makes this event work and what makes future ones possible.

Monday, May 4th | Merkin Hall at Kaufman Music Center | 129 W 67th St, NYC
6:00–6:45 PM — Networking Reception (Balcony Lobby)
6:45–8:15 PM — Live Pitch Event
8:15-9:30 PM — Post Event Networking

RSVP HERE

Thanks in advance! Feel free to message me if you have any ideas of getting the word out.

Watch the Recap

🎥 Episode 5 HERE

(Fisher, our talented videographer, had his camera break last week, so this episode was shot on an iPhone. Enjoy!)

If you’re curious, here are some of the videos our founders made this session too:

Get Involved

🦈 Shark: Join our investor panel at the NYC event
🤝 Mentor: Meet with a student founder (30 min, remote)
📈 Investor: Get connected with our founders


Until next time,

Michael

I’ve been thinking about it a lot lately — not just in the context of this class, but in my own company. For the past month at Spacemilk, I’ve gone back to square one with customer discovery. We collect data from follow-up questionnaires, order history, ad performance — the standard stuff. But I started calling our most loyal customers directly. Asking them about their routines, what motivated them to try us, why they came back. And what I heard back didn’t always match the assumptions I’d been operating on.

As founders, we build these mental models of who our customer is and what they want, and over time those models start to feel like facts, when they may be disguised assumptions. And unless you’re actively questioning them, you’ll build your entire messaging strategy on a foundation you never actually verified.

That mindset, the willingness to question what you think you already know, ended up being the theme of this week’s class, even though I didn’t plan it that way.

The Reverse Pitch

Most classes I prepare for well in advance, but today’s workshop came to me last minute. Around 11 pm on Tuesday night, I was trying to think of ways to run a workshop that was both meaningful to our founders but also introduced their companies to our guest speaker, Andrew, who sat in for the whole session.

The reverse pitch. Every student was randomly assigned someone else’s company. They had 5 minutes to research their peer’s startup or write down anything they could remember from the past six classes, followed by 5 minutes with the student-founder to ask some questions. Then they had to stand up and pitch that person’s business with no scripts or slides to lean on.

Nick Dargel went first and immediately set the tone. He pitched Sage’s company, Link’d, with a clarity and energy that surprised the room. He knew her business well enough to deliver it like it was his own and it raised the bar for everyone that followed.

The results were a mixed bag, which was the point. Some founders found it easier to talk about a business they weren’t deeply involved in. Others found it way harder to communicate a product that wasn’t their own. But the real value was in three things:

Founders got to hear how someone else perceives and describes their venture. When you pitch your own company every day, you stop hearing how it sounds. A peer’s version of your business — what they emphasize, what they skip, what they get slightly wrong — is a mirror you can’t get any other way.

It was a true public speaking exercise. No scripts, unfamiliar material, thinking on your feet. That’s a skill that matters well beyond a pitch competition.

And it was a clarity test. If someone who’s been sitting next to you for seven weeks can’t describe what you do, the question isn’t whether they were paying attention. The question is whether you’ve been describing it clearly enough for it to stick.

Andrew Lacey

From there, we welcomed Andrew Lacey as our guest speaker. Andrew is a Wesleyan alum who spent his career in asset management and portfolio management on Wall Street — the kind of person who’s sat on the other side of the table from founders his entire professional life, evaluating what businesses are actually worth.

Andrew’s session challenged another set of assumptions our founders didn’t know they were carrying: what does it mean for your company to have a valuation, and where does that number come from?

For businesses with revenue, he framed it around four things: how much cash the business generates, how durable that cash flow is, what growth and competitive advantage look like, and how much capital it takes to scale. For pre-revenue companies (which is about half of our cohort) it’s about building a credible chain of logic. Start with your total addressable market, narrow it to what’s actually serviceable, get specific about what you can realistically capture, and connect that to unit economics.

His point: investors aren’t just evaluating numbers, they’re evaluating the probability that your story holds up. The more grounded and specific you are, the more seriously they’ll take you.

Andrew also stayed after class through our lunch period (shoutout Mondo Pizza) and sat with students individually to work through valuations based on their real numbers and context. Those one-on-one conversations ended up being some of the most valuable of the semester.

Rowan Tracey said afterward that Andrew reframed something he hadn't questioned all semester. Valuations aren’t everything. If a company like his (Medfield Junk) produces money, why does he have to exit? In this class, we talk a lot about typical startup accelerator trajectory, but a junk removal business’s lifespan is far different than a B2B SaaS company, thanks Andrew.

President Roth’s advice to question everything is easy to nod along to during orientation. It’s harder to practice when you’re deep in the weeds of your own company, surrounded by your own assumptions. This week reminded all of us — myself included — that the founders who keep growing are the ones who keep asking.

May 4th: It’s Official

I’m extremely excited to share that our final date and venue are set. Our culminating final event will take place on…

Monday, May 4th | Merkin Hall at Kaufman Music Center | 129 W 67th St, NYC
6:00–7:00 PM — Networking Reception (Balcony Lobby)
7:00–9:00 PM — Live Pitch Event

RSVP HERE

Six student-founders. A panel of angel investors who can invest on the spot. A $5,000 audience-choice grant. Presented by the Patricelli Center for Entrepreneurship in partnership with the Digital Wes Alumni Network.

If you’ve read this far (thank you so much) you should come. Please RSVP.



To infinity and beyond,

Michael


PS - Fisher, our super talented CSO (Chief Storytelling Officer) had his camera break on the walk to class. So we have no video for this week, but we will be back for Week 8! Stay tuned.

But hard skills are only half the equation. And the half that’s getting commoditized fast. Nearly anyone can whip together a go-to-market strategy, a business plan, and a working product with AI in a couple of days (maybe a couple of hours now). When the technical barriers to starting a company fall this dramatically, the question stops being can you build it and starts being can you lead it.

Not leadership in the corporate training seminar sense. Leadership as in: when things go sideways, how do you respond? When your team is stuck, do you take over or do you listen? When you’re under pressure, can you organize people and make decisions without a playbook?

Where We Are

We opened class the usual way, each sharing one win from the week and one roadblock experienced. Then I told everyone we were starting with a team-building exercise. A brain teaser to warm up. Nothing more.

What I didn’t tell them was that the exercise was the lesson.

We split into four teams and handed out a riddle (see below) — a logic puzzle with 15 clues, five categories, and one missing answer. Each team could only designate one person to hold the pen and paper, so before anyone could start solving, they had to decide who controls the board. That selection process alone was revealing.

The groups competed for a priceless prize: pride. The first team solved it in 16 minutes. Two teams finished around the 30-minute mark. One team didn’t finish. We had to call it after an hour.

After the timer stopped, we revealed what the exercise actually was. This wasn’t a warmup. It was a leadership diagnostic. Palmer and I watched to see who took charge and who deferred. Whether teams divided the clues or tried to brute-force them together. How people responded when they hit inevitable adversity.

The true value of the class was in the discussion that followed. We connected those behaviors back to each founder’s experience running their own venture. The dynamics that played out over a logic puzzle — how you organize, how you delegate, how you make decisions when the answer isn’t obvious — those are the same dynamics that play out every day when you’re building a company.

Professor Tim Nguyen

From there, we brought in Professor Tim Nguyen. He teaches the growing category of classes at Wesleyan called Organizations and Society. His classes cover big data and responsibility, capitalism and its criticisms, and business ethics.

The discussion centered on a research article titled “A Garage and an Idea: What More Does An Entrepreneur Need?” by Pino Audia that argues the missing ingredient for most entrepreneurs isn’t an idea or technical skill — it’s organizational experience.

The popular narrative in entrepreneurship idolizes the garage founder. The best startup success stories come from scrappy founders building future billion dollar businesses like Walt Disney or Steve Jobs, who dropped out and built Apple from his parents’ house. But the data tells a different story. The majority of successful entrepreneurs come from organizations where they picked up three things: confidence, information, and community.

This was provocative for our class, because none of these students have big corporate experience and most of them don’t plan to. They’re not going into consulting or investment banking after graduation. They’re building companies now and aspire to continue doing so after graduation.

Nelson Bellows pushed back directly. Why would an analyst sit in a chair and crank out Excel models for 16 hours a day when Claude can finish it in 10 minutes? Is that manual grind still valuable, or is it an outdated prerequisite that AI has made irrelevant?

It’s a real question. If the traditional path to developing leadership skills was through years of reps inside big organizations, and AI is compressing or eliminating a lot of those reps, then where does leadership development come from? Feel free to chime in the comment section with your take:)

The dialogue in class was healthy and grounded in genuine curiosity about a cultural shift in career pathways. When coordinating this lesson, it was intentional to include a contrarian perspective. Our founders are ambitious and confident — they should be. But they're also college students, and compared to a seasoned executive or serial founder, they have less mileage. A big part of what we do here is expose students to perspectives and frameworks that push back on their instincts, so that confidence doesn't turn into blind spots. Ambitious and grounded can coexist. That's the founder we're building toward.

Beyond the Classroom

There’s a broader shift happening that makes this conversation more pressing than it might seem on the surface.

The 2026 Edelman Trust Barometer — which surveys nearly 34,000 people across 28 countries — found that trust in business sits at 64%, while trust in government has fallen to 53%. Business has been more trusted than government every year since Edelman started tracking this comparison and that gap does not appear to be closing.

When trust migrates from traditional institutions to businesses, the people running those businesses inherit a responsibility that didn’t used to come with the job. Founders who plan on leading successful businesses are no longer just building products, they are also becoming leaders that people look to. Whether it is a pandemic, social movement or political crisis — the spotlight finds the CEO now, and stakeholders expect them to stand in it.

This is something we think about a lot at Wesleyan Shark Tank. Beyond learning how to pitch, we aim to build the kind of well-rounded, interdisciplinary thinkers that this moment demands. Wesleyan has always taken pride in shaping people who can think critically across disciplines and that liberal arts approach to leadership is becoming more valuable, not less, as AI handles more of the technical work. The founders who stand out won’t just be the ones who can build the best product. They’ll be the ones who can lead, communicate, and earn trust.

Coming Up

We’re off for two weeks for spring break. Our founders have earned a well-deserved break (although most of them are more excited to have two weeks to focus on their company without school). We have a lot planned for the second half of the semester.

Most importantly: We have locked in our final event date and venue! May 4th from 7–9 PM at Kaufman Music Center (129 W 67th St, New York). Networking reception kicks off at 6 PM. More details to come, you won't want to miss this.

Watch the Recap

🎥 Episode 6 HERE

Get Involved

🦈 Shark: Join our investor panel at the NYC event
🤝 Mentor: Meet 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

Meanwhile, 1,200 miles east, our student-founders spent yesterday doing the exact same thing — standing up in front of a room and trying to make people believe in what they’re building.

Pitching never stops. It doesn’t matter if you’re a student in a classroom or a founder walking into corporate headquarters halfway across the country. You’re always pitching someone — investors, customers, partners, press, your own team. It’s the one skill that shows up in everything you do as a founder, and it’s the one most people underestimate because they think it’s just talking. It’s the reason we describe Wesleyan Shark Tank as an accelerator course designed to teach founders how to pitch. Everything else we cover — customer personas, go-to-market strategy, marketing, fundraising — ultimately feeds into whether you can look someone in the eye and make them say yes.

Where We Are

Palmer led this week’s class while I was traveling. The entire session was dedicated to pitch workshops — everyone stood up, delivered their pitch, and got honest feedback from the room.

Two founders in particular are a good example of the challenge. Liam Farrell is building Planisphere, a platform that streamlines the acquisitions process for real estate private equity firms — sorting through emails and documents to determine whether a potential deal is worth pursuing. It’s a highly technical product in a category most people outside of real estate have never thought about. As Liam put it, he demos to real estate professionals all the time, people who already speak the language. Translating that into a pitch for a room of people who don’t live in that world is a completely different exercise.

Then there’s Cal. Cal McClary is building VitalPatch — a non-invasive adhesive patch that attaches to a patient’s arm and continuously sends vital signs to EMTs via Bluetooth. He came up with the idea while working as an EMT himself, watching paramedics manually retake vitals on stable patients over and over. He wears a Whoop. He can check his own vitals from his phone anytime. Why didn’t anything like that exist in an ambulance? That’s his pitch. It’s intuitive, it’s visual, and most people get it in ten seconds.

Two very different companies, two very different communication challenges. Liam has to take something complex and make it simple. Cal has to take something that sounds simple and prove it’s a real business. But both of them are working on the same fundamental skill — can you make someone understand and care about what you’re building in under a minute?

The Shark Tank Connection

The class is called Wesleyan Shark Tank for a reason. At its core, Shark Tank is the ultimate test of whether a founder can tell their story under pressure. That's the skill we're building toward. What started as a fun name ended up becoming a real connection to the show itself.

Last year, I noticed that Ken Fuchs — the director of Shark Tank — was a Wesleyan alum. I went to our athletic director (shoutout Coach Whalen), who happened to be in the same graduating class as Ken, and asked for an introduction. My co-lead at the time, Ben Carbeau, and I got on a call with Ken and his wife, Kate (former Executive Producer of Shark Tank) that was supposed to be quick and lasted over an hour. They were genuinely excited — Ken’s alma mater building a class around the show he runs. That relationship grew into me spending time as a production assistant on the actual Shark Tank set this past summer. The Wesleyan network at work.

Now Kate generously gives her time and coaches each one of our student founders on their pitches one-on-one. There is no one in the world better suited for this. Her entire career was built around evaluating whether a founder is pitch-worthy and then preparing them for that moment. Whether it’s a technical B2B platform or an adhesive patch for EMTs — it all comes down to the same thing. Can you tell a story?

That’s what we’re working on. From a Middletown classroom to a Minneapolis boardroom to the Shark Tank stage — it starts with the pitch.

Watch the Recap

🎥 Episode 5 HERE

Get Involved

🦈 Shark: Join our investor panel at the NYC event
🎤 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

In fact, startups might have the edge. Big brands are boxed in by layers of approval, legal review, brand guidelines. Startups can move fast, take risks, and tap into internet culture in ways that corporate teams spend months trying to replicate. That dynamic creates this ripe space where founders can build real brands through content alone, no ad spend required. This week’s class was built around that idea.

Where We Are

We kicked off Marketing Series Part 1 with three speakers who each brought this to life from a different angle.

Yuchao Wang ‘25

Yuchao Wang ‘25 was one of our student founders from last year’s pilot cohort and the founder of Han Chung Classics. I met Yuchao early last year — we bonded over both having ecommerce brands and spent countless hours in the High Rise apartments sharing notes and bouncing ideas off each other.

I got a front row seat in watching Yuchao’s growth as a student-founder. At the end of last year’s Wesleyan Shark Tank program, I spoke with Yuchao to reflect on the experience and he said something that stuck with me.

”This class reignited the entrepreneurial spark for me” he told me. His experience as a founder had been increasingly tough at Wesleyan as he hadn’t found community or curriculum that matches his ambitions and with career decisions looming, he was on the fence about if it was possible to work on his company full time. This class was the first time he was surrounded by like-minded students going through the same unique startup experiences that he was.

Seeing him on the other side of the table now, presenting to this year’s cohort, was a full circle moment. He walked the class through his methodology behind content pillars — how he thinks about what to post, why certain formats work, and the analytics insights business owners need to understand. Few people know how to work the organic algorithm like Yuchao. He gets millions of views on his content and has never put a dollar behind any of it (see below). For a bootstrapped startup, that’s everything. What better proof that you don’t need a Fortune 500 marketing budget to build a real brand?

Louise Astorino & Evan Reeves — Not An Ad

Louise Astorino (Forbes 30 Under 30 + my cousin) and Evan Reeves (first hire at Jerry Media) are the co-founders of Not An Ad, a creative agency behind campaigns for Domino’s, Panera, Dunkin’, DoorDash, Lyft, Fanatics, and Paramount Pictures.

What stuck with me watching the class during their session wasn’t the content itself (which was phenomenal)— it was the reaction. Companies like Domino’s and Paramount can feel untouchable when you’re a student with a startup. They’re massive. They’re corporate. They feel like they exist in a completely different universe. But when you hear from the actual people making the content for those brands, it humanizes the brand — these are real people who are plugged into the same internet culture as the students sitting in the room. They’re riffing on the same memes, following the same trends, thinking about content the same way.

That realization was powerful. And it validated the whole thesis. Louise and Evan started their careers doing exactly this — making scrappy, on-trend organic content. Now they’re working with some of the biggest companies in the world, and the core strategy hasn’t changed. It’s still about understanding what resonates, being authentic, and being willing to be funny. The scale changed, but the playbook didn’t.

The meme exercise was a class favorite too. Louise and Evan had students create memes for their own companies using the same frameworks they use for their Fortune 500 clients. Here are a few from class:

Nelson & Spike

Today’s student-founder spotlight is Nelson Bellows ‘26. Nelson and his two co-founders are building Spike, a prediction market for short-form content. The concept is simple — you’re scrolling TikTok, you see a video, and you trade on whether it will go over or under what they call the “viral line.” So you might see an Alex Earle video, export it to Spike, and the platform generates a line at 10 million views. You think her hook is strong, you think the format is trending — you take the over.

It’s a business that lives entirely at the intersection of content and virality, which made this class especially relevant for him. Everything we talked about — how trends spread, what makes content resonate, why certain formats outperform others — that’s not just marketing strategy for Nelson. It’s the core mechanic of his product. He’s learning how to market a startup while simultaneously building a platform that depends on understanding exactly how content performs. Check out this week’s YouTube video to hear him speak on it.

Coming Up

I (Michael) am headed to Minneapolis for a big pitch for my company, Spacemilk. So, Palmer will be leading the session. Stay tuned to see what is in store!

Watch the Recap

🎥 Episode 4 HERE

Get Involved

🦈 Shark: Join our investor panel at the NYC event
🎤 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

Twelve months later, I had scaled my company and sold it over the summer. I was mentored under Strauss Zelnick, CEO of Take-Two Interactive - who offered to work with me after watching my pitch at our final event. The company I presented was Perfect Beach Day, an all-inclusive beach concierge service that employed 30 crew members across 12 beach towns on the Jersey Shore. I ran it for four summers. I arguably had the best office across any industry: the beach.

The spontaneous “yes” turned into the most meaningful experience of my time at Wesleyan. This year, I’m co-leading the program alongside Michael. Full circle is an understatement.

Throughout our countless meetings pitching Wesleyan Shark Tank to alumni, I’ve realized just how tight knit and committed the Wesleyan community is. The breadth of industries, impact, and creativity produced from this institution speaks to the caliber of people Wesleyan attracts. To any alumni reading this who we’ve connected with or who have supported this program in any way, thank you.

One standout example is Matthew Wheeler, Class of 2005, former lacrosse player (Go WesLax) - who founded SportsRecruits, the platform that became the go-to tool for high school athletes navigating college recruiting. It also just so happened to be the app I was recruited from to play at Wesleyan.

Where We Are

We began class with our traditional: One Win, One Roadblock, and One AI Use Case (building off of last class’s lesson). Matt shared that his AI use case was using ChatGPT as his sommelier for his wife’s surprise birthday party - creative.

Michael and I design our curriculum to build progressively each week. Last week, we focused on WHO our founders are targeting, by building detailed customer personas. This week, we focused on HOW we are reaching them in a go-to-market workshop. The lesson was mapped using the Bullseye Framework from Gabriel Weinberg’s, Traction.

Weinberg explains there are 19 possible channels to reach your customers - everything from SEO to community building to cold outreach - and most founders default to the two or three they’re most comfortable with instead of testing what actually works. The framework forces you to brainstorm all 19, narrow to your top 3 based on where your customer actually spends time, and then go all-in on one to test first.

After identifying their top three channels, students drafted one real piece of outreach - a cold email, a LinkedIn post, a community forum intro - for their primary channel. Homework: send it before next class.

Matt Wheeler '05

We welcomed Matt for his workshop on funding a startup. Matt addressed the question every founder must eventually confront: where is the money coming from, and what does it cost you?

He and his partner, Chris Mead, raised a total of $2.2M across the entire life of SportsRecruits. They were acquired by IMG Academy last year. Matt emphasized his bootstrapped approach and that at the end of his sale, he and his partner Chris were able to call their shots and walk away with a handsome payout. Matt is now CEO of Clipp’d, an AI-powered highlight reel platform for golfers.

Of the 5.2 million businesses started in 2024, only 3,600 received VC seed funding. That’s less than 1 in 1,000. And of those VC-backed companies, 75% fail to return capital to their investors.

Matt emphasized that capital is never free. You either pay with interest (debt) or you pay with ownership (equity). Every dollar has a cost, and the default assumption in 2026 that you need to raise venture capital is, statistically, wrong.

Matt broke down the reality of VC and the funds that are raised in order to pay out their LPs. A VC has a $100M fund. They take 20% of your company. For your company to “return the fund,” you need to exit at $500 million. So if you sell for $50M, a life-changing outcome for most founders, the VC gets $10M back. To them? That’s a failure.

Alternatively, for the same $50M exit. If you bootstrapped and still own 80%, you take home $40M. If you went the VC route and own 20%, you take home $10M. Same exit price but an entirely different narrative.

Matt was not anti-VC – rather, he was helpful in informing students of their funding options so they can make a grounded decision on where they fundraising come from.

The Litmus Test

Before our founders pitch the Sharks on April 27th, Matt told them to sit with three questions:

Is the market huge? Can this realistically be a billion-dollar company? If your TAM is under $50M, VC probably isn’t your lane.

Do you actually need the cash? Are you building hardware or biotech? Or can you sell version 1.0 tomorrow?

The ego check. Do you want to be famous - TechCrunch headlines, conference keynotes - or do you want to be wealthy and free?

Coming Up

Week 4: Louise Astorino (∫Forbes 30 under 30) of Not An Ad and Yuchao Wang ‘25 (Former Wesleyan Shark Tank student) of HCC Popups join us for a marketing masterclass. We’ll cover the essentials of building a personal brand through social media strategy, organic growth, and content pillars. Louise will share the frameworks she used to land Domino’s as a client and lead their marketing campaign.

Watch the Recap

🎥 Week 3 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 mastorino@wesleyan.edu


Cheers,

Palmer

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.

Who We Are

Wesleyan Shark Tank is a student-led accelerator course designed to teach founders how to pitch. Last spring, Ben Carbeau ‘25 (former co-teacher), and I ran our pilot class with 12 students and 7 ventures. Over the semester, we brought in guest speakers every week — lawyers, startup founders, brand strategists, even the Executive Producer and Director of ABC’s Shark Tank — and built a curriculum around everything it takes to scale and do what startups do best, pitch.

The semester culminated in a live Shark Tank-style event at the Ring Theatre on campus, where our founders fearlessly walked on stage to the Shark Tank theme song and pitched their ventures to a panel of seven Wesleyan alumni investors. Over 300 people showed up. $20,000 was invested live on stage. A smashing success, yes. But also, proof that this was a successful medium for bridging the gap between our ambitious student founders and a supportive alumni network.

If you want the full backstory, The Wesleyan Argus covered both the class and the event last spring.

Where We Are

It has been 281 days since last year’s class came to a gratifying close.

This past Wednesday marked the first day of class for Season 2. A brand new cohort of student-founders sat around the boardroom table in the Patricelli Center for Entrepreneurship, each building something wildly different. From freshmen to seniors, softwares to CPGs, everything from a prediction market for social media virality to an AI-powered adaptive skincare company was present. In typical Wesleyan fashion, the room was vastly diverse and packed with creativity.

Before class, I told our students the only thing they needed to prepare for the first day was to bring their computers and a good attitude. To their surprise, our opening introduction activity put everyone on the spot. Each founder had to stand up and give a cold 90-second pitch of their business. It was the first time most of them had pitched out loud to a room of peers (with no preparation), and it showed— in the best way. Some were sharp. Some went way over time.

Everyone learned something about how hard it is to take the thing you’ve been building and distill it into a clear, simple story. That’s going to be the central challenge of this semester, and we wanted to put it front and center on day one.

What’s New This Year

We’re building on everything we learned from last year’s class, and we’ve already made some major upgrades…

The final event moves from Wes to NYC. In late April, six founders will be selected to pitch to a panel of alumni angel investors on a real stage in New York City. This is the flagship moment we’ve been working toward. In partnership with the PCE and Digital Wes, we are bringing the Wesleyan entrepreneurship community together in a setting that matches the caliber of the founders and alumni involved.

Our student leadership team has expanded. Palmer Zarzycki ‘28 is co-leading the course after pitching Perfect Beach Day NJ as a student founder last year and exiting the venture over the summer. Adil Mohammed ‘27, a member of last year’s cohort who founded OneChart and has since scaled to six figure ARR in a year, is back as our Resident Advisor. And Fischer Hirsch ‘26 is our CSO (Chief Storytelling Officer), documenting the entire journey through video, photography, and media production.

Bringing alumni back into the entrepreneurship ecosystem. This program is designed to engage with our alumni in a meaningful way, whether through mentorship, guest speakers, or the “Sharks” themselves. Palmer and I have connected with over 100+ alumni this past semester in our mission to reignite Wesleyan’s entrepreneurial flame.

Meet the 2026 Cohort

Nelson Bellows ‘26: Spike — The prediction market for short-form content. Users trade on whether videos are going viral, with 50+ featured daily.

Nicholas Dargel ‘28: SCAP Athletics — A patent-pending shoulder mobility and recovery tool built for athletes. Already being used by college programs like Auburn and Georgetown, and expanding fast.

Adam Shatz ‘27: Milieu — At-home skin microbiome testing meets AI-powered adaptive skincare. In-market and generating revenue.

Liam Farrell ‘26: Planisphere — AI-powered deal triage for real estate investment firms. Already in-market with a $500K+ pre-seed closed.

Sam Pohlman ‘26: Jam Scsh — Redefining how musicians monetize and connect with fans through live music and social media.

Chukwudi Udechukwu ‘27: LockerRoom — A unified platform for athletes and coaches to streamline communication, playbook learning, and daily team operations.

Lois Amponsah ‘27: Wings of Change — An NGO and e-commerce platform empowering youth entrepreneurs in Ghana through workshops, mentorship, and a digital marketplace.

Rowan Tracey ‘29: Medfield Junk — A junk removal and hauling company servicing Greater Boston, built and operated entirely by college and high school students. Already scaling.

Sage Saada Saar ‘26: Link’d — An app that syncs two people’s calendars and autonomously books a meeting at the best available time, removing the back-and-forth of scheduling entirely.

Cal MacClary ‘28: VitalPatch — A noninvasive adhesive patch with an embedded sensor for real-time health monitoring.

Week 1 Rundown

Beyond the cold pitches, the first class was about getting everyone on the same page. Your typical run of show: syllabus, expectations, deliverables, and setting the stage for the final event where only 6 students get selected to pitch in NYC (competitive!)

After each founder’s pitch, the cohort gave honest feedback: one thing that worked, one thing that didn’t, and one hard question from a peer. For two reasons:

1. This year’s theme is “Learning through action.” We want our students to be comfortable doing uncomfortable things and then adapt based on feedback. This activity was a great way to introduce one another, but more importantly, it was designed to build confidence through overcoming challenges.

2. Each pitch was recorded and archived. In 4 months from now, students will go back and watch these and see tremendous improvement (if all goes according to plan).

The biggest takeaway? Simplicity is deceptively hard. When you live inside your own company every day, the “explain it like I’m five” version is surprisingly the last thing you can articulate clearly.

Watch the Recap

🎥 Week 1 Recap on YouTube

Coming Up

Week 2: We’re diving into AI as a founder’s toolkit: how to use AI agents, automation, and productivity tools to operate like a much bigger team. Plus a hands-on workshop on customer personas and articulating your value proposition. Stay tuned.

Get Involved

Wesleyan Shark Tank runs on alumni and community. Here’s how you can help:

🦈 Shark: Join our investor panel at the NYC final event (late April / early May)
🎤 Guest Speaker: Lead a class session and workshop on your area of expertise
🤝 Mentor: Meet biweekly with a student founder (30 min, remote)
📈 Investor: Email us and get connected with our founders

Interested? Reply to this email or reach out directly: mastorino@wesleyan.edu

Until next time,

Michael Astorino