Week 7: Question Everything

Why?

During freshman orientation, Wesleyan president Michael Roth told the 2026 class something I didn’t expect to remember. He said if we left with anything from our time here, it should be this: question everything. Question authority, structure, how things are done, what you learn, why you think a certain way. I admittedly did not pay a ton of attention to much during orientation. But that line stuck with me for some reason, and I’ve carried it with me since.

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

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.