Mar 3, 2025 · 34m · the-pitch
#65 Wait, Your App Does What Exactly?
Spencer Shulam · 13m spoken Josh Muccio · 6m spoken Alexandra Stanton · 2m spoken Charles Hudson · 2m spoken Phil Nadel · 2m spoken Sheel Mohnot · 2m spoken Heather Rogers · 22s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Pitch, 23-year-old founder Spencer Shulam attempts to raise $1.5 million for his startup WeDo, but struggles to win over investors when his grand vision of mapping human behavior clashes with the reality of a student to-do list app.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Josh holds 24.2% of the talking time here. How this is scored →
Josh as informed peer 5.3 Guest teaching 1.7 Guest disagreement 2.3 Josh pushing back 5.9
speaking balance: gold is Josh, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 7:24 Direct challenge on calendar adoption
Spencer directly challenges Sheil by asking for an example and bluntly declaring that students simply do not use Google Calendar.
Hardest push from Josh ▶ 17:58 Investor rejection over incomprehensible pitchSheil delivers a direct refusal of Spencer's framing, emphasizing that he failed to understand what the product actually does for the entire first fifteen minutes of the meeting.
Biggest teaching moment ▶ 6:26 Spencer reveals high user retention metricsSpencer educates the investors on his traction, citing thirty percent retention after nearly a year and presence in over eight hundred schools.
Josh holds their own ▶ 20:39 Alexandra reconstructs Spencer's pitchAlexandra demonstrates venture expertise by concisely rebuilding Spencer's pitch on the spot, demonstrating exactly how he should have positioned his product to investors.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Josh as informed peer | Guest teaching | Guest disagreement | Josh pushing back | Why |
|---|---|---|---|---|---|---|
| Spencer Presents the WeDo Vision | 5 | 1 | 2 | 6 | Spencer opens with high-level philosophy about mapping mistakes, prompting Phil and Sheil to press immediately for what the actual product is. The friction peaks when Spencer realizes he left his phone in the other room and has to leave the pitch to retrieve it. | |
| Live Demo, Syllabus Features, and Traction | 5 | 3 | 4 | 5 | Spencer demonstrates the app and quotes strong retention metrics, but pushes back sharply against Sheil when Sheil suggests Google Calendar competes with student planners. | |
| Founder Background and Human Behavior Mapping | 5 | 2 | 3 | 6 | Spencer outlines his teenage founder history before pivoting back to grand claims about mapping micro-actions across a human lifetime. Alexandra steps in with structured pushback, asking how tracking school assignments connects to long-term behavioral forecasting. | |
| Monetization Strategy and First Investor Pass | 6 | 2 | 2 | 6 | Spencer details the five-dollar monthly subscription model and concedes predictive interventions are not yet active in real time. Charles delivers the first formal rejection, stating the connection between the problem and product simply does not compute. | |
| App Redesign Walkthrough and Final Investor Rejections | 7 | 2 | 3 | 8 | Spencer presents the conversational v2 interface, sparking brief interest before the investors issue unanimous passes. Sheil and Alexandra forcefully critique Spencer's inability to explain his product within the first fifteen minutes. | |
| Post-Pitch Debrief on Communication Failures | 6 | 0 | 0 | 7 | During the post-pitch debrief, the investors and Josh dissect Spencer's critical flaw of failing to read the room and continually spiraling into abstract concepts rather than clarifying core product functionality. | |
| Six-Month Follow-Up and the Acquisition Dilemma | 3 | 2 | 2 | 3 | In a reflective follow-up six months later, Spencer candidly discusses his fundraising struggles, lack of personal runway, and mixed feelings regarding an impending low-value acquisition. |
Statements from this episode (15)
Shulam: WeDo tracks micro-actions to build a map of human behavior
“Today we're helping students build and maintain healthy routines, and then we use that data to also help them track daily tasks and stuff like that. This is all in the effort of tracking micro actions people take to building a map of human behavior.”
Spencer Shulam: WeDo automatically converts student syllabi into due dates
“So if you're a student, you can actually send us your syllabus that gets converted into due dates and reminders for you automatically.”
Spencer Shulam: WeDo achieves 30% retention, beating competitors by 20x
“And just from the data alone, we have 20 times the retention of the best products in our space. We're able to get to about 30% retention even after 10 to 12 months.”
Spencer Shulam: WeDo reached 15,000 active users across 800 schools
“We grew to over 800 schools. Last semester we ended with about 15,000 monthly active users.”
Spencer Shulam: WeDo converts about 6.6% of users to paid subscriptions
“We convert about 6.6% of our users to that paid subscription.”
Spencer Shulam: WeDo has slightly fewer than 1,000 paid subscribers
“A little bit less than a thousand.”
Spencer Shulam: WeDo retains 60% to 80% of paid subscribers
“And then our retention with our subscription is relatively high, around 60, 80%.”
Spencer Shulam: WeDo can predict whether a student will fail a class
“We, for example, can even today start predicting if a student's going to fail a class within the first few days of signing up for our product because we're able to see they're not marking off certain assignments, and we know other people who are just like them…”
Charles Hudson passes on WeDo over disconnect between problem and product
“So I totally identify with the problem, but I'm having a really difficult time connecting the problem statement to the product, so for me, this one's gonna be a pass, but I can tell you have real enthusiasm and energy about solving this, but for me, it just do…”
Spencer Shulam: WeDo is raising $1.5M with backing from Pritzker, Crosscut, Amplify
“Part of this round, so we're raising a million and a half dollars. We have some great existing investors like Pritzker Group, Crosscut, and Amplify.”
Spencer Shulam: Predictive planners fail without 24/7 personal routine data
“There have been a lot of predictive planners out there. They all don't work because they have no idea what's happening before work and what's going on after work. They don't know if you didn't sleep enough. Maybe meditating in the morning would really help. Ma…”
Phil Nadel: WeDo is just a task management app for college kids
“I just think it's a task management app for college kids, and that's all it is right now today.”
Charles Hudson: Founders losing a pitch must stop and reset
“I think part of your job as a founder is to recognize when you're losing the room. And instead of allowing things to spin out of control, stop and like, hey, maybe I haven't been clear. Let me start over.”