Hello from the Trough of Disillusionment
Chronicling my entrepreneurial journey cold-emailing my way to Bankruptcy.
Hey friends,
It's been about a month since our last update—far cry from the "weekly" updates I promised. But in my defense, it’s hard to send cheerful updates when you have no wins to report.
I still don't have fiscal sponsorship despite BEGGING over a dozen orgs—including several offices at my alma mater. In many cases, I was actually very persistent. I camped outside a few offices for weeks till I talked to the person in charge, only to get shot down.
When I started this, I genuinely believed I could assemble a world-class board, raise a million dollars, and go straight to building a campus.
Hoo boy. To say I was delusional would be generous.
From Delusion to Reality Check
At first, this lack of progress had me spiraling, but one cold email to Matt (founder of 4.0 schools) completely changed my perspective.
See, I'd been hitting up some very senior folks—Eric Hanushek (Stanford), David Figlio (Rochester), who are literally at the top of their fields, thinking that these individuals would risk their reputation serving on the board of a very unproven non-profit. Even my alma mater. I thought fiscal sponsorship from UofR was realistic. But as Matt pointed out: the ask was huge, and the upside (to them) unclear (no, it's not enough that we could potentially change "millions of lives").
And this is where Matt's advice showed me what I was doing all wrong. I had to slash my ask by 10X and go from:
Asking seasoned folks to join my board
Asking donor orgs for $$$ for a whole semester abroad
To instead:
Running a handful of 2-hour workshops
Repeating this at least a few times
Gradually expanding to 1-day and 2-day workshops
And only THEN thinking of taking kids abroad
These workshops would allow me to:
Create inroads into the Rochester community
Get real-world feedback to refine my model
Create proof points and traction that could help build credibility with donors
And more importantly, I'd greatly lower my ask and make it easier to secure a win of some kind, which I could then leverage to secure a bigger win.
I thought I'd started small with my pilot, but I was honestly dumbstruck to realize I could scale down things by a whole order of magnitude!
Turns out you can't raise on vision and conviction alone—proof of work reigns supreme.
Where We're At Now
🚪 Rochester Workshops
I've started conversations with iZone and Upward Bound in Rochester. I'm pitching a 1-2 day design thinking & leadership workshop for underserved teens. Even if they say no, I'll find a way to do it solo. All I need is a whiteboard and some folding chairs.
I just need tangible proof that this thing works. Not in theory, not on Substack—but in a school gym, with real students, who leave the room a little more empowered than they walked in.
Prospera this fall might still be possible, but no longer the hill I'm dying on. Summer program? Very doable, if I can just get someone to say yes.
🌐 KLS Uganda
In my previous post, I mentioned how DLA is exploring a dual track—campus in Honduras, and piloting a Khan Lab School in Uganda's elite boarding schools.
My incredible apprentices—now down to Michelle and Courtney (James, left for law school—no hard feelings)— have been making steady inroads with Uganda's elite boarding schools, evangelizing Mastery Based Learning to all stakeholders—School Boards, Admins, PTAs, etc. Everyone seems receptive to the idea so far, but we'll know for sure if any of this warm reception is worth anything when a school actually bites.
For now, we've invested in some high-quality marketing material (check it out here) and will be having concrete discussions with school admins over the next few weeks. This Ugandan angle is our strongest card right now. If we secure even one prestigious school as a partner, it significantly boosts our credibility with Sal and potential funders.
✨ The Way Forward: Small Steps, Big Vision
The immediate focus is survival until the next milestone. I need some tangible outcome – a workshop, a school partnership, anything – that transforms my story from "guy with crazy idea" to "founder with early validation."
The Próspera pilot this fall feels like a long shot given our current traction, but a summer program might still be within reach. Either way, I refuse to compromise on the vision – educational arbitrage as a tool for both individual transformation and community development.
In those moments when I wonder if this is all worth it, I remember why I started: Every successful school means hundreds of students transformed AND a community lifted. Every campus built means infrastructure extended to regions that desperately need it.
And that's still worth fighting for, even if we have to start with a 2-hour workshop in Rochester.
🕊 ENTREPRENEURIAL MUSINGS: HOW TO KNOW WHEN TO GIVE UP vs. WHEN TO KEEP PUSHING
I recently wrote this on my LinkedIn and thought it would be particularly relevant to the overall theme of this newsletter.
A question I often get from aspiring entrepreneurs I mentor is: how do you know when to give up—and when to keep going?
Here's how I think about it. This applies to startups, sure—but also to anything that takes unreasonable effort before results show up.
You only need one yes
If you still believe in your vision, still have runway, still have ideas, keep iterating
Commit to a number of rejections you're willing to eat before stopping
Let me break those down:
1. YOU ONLY NEED ONE YES
People who know me personally know it took me three application cycles to get into college in the US. If you know anything about US college admissions, you know it's a brutal process for American teens—now imagine being an international student like me who couldn't even afford $5K.
Over three years, I applied to at least two dozen schools (which I later found out was on the low end, funny enough). Applying was expensive—SAT fees (I took it 4 times), app fees, sending scores. I was making $60/month at the time, working 6 days a week with no meals, no transport, no health insurance.
I estimate I spent over $4,000 over 3 years chasing that dream. And when I finally got admitted, I still needed to raise ~$8,000 to enroll. To raise all this money over 3 years, I sold everything I could get my hands on— fruits door to door, juice and hotdogs at church events, even high-end real estate deals, and eventually sold everything I owned—car, motorbike, businesses—everything had to go.
But it was worth it. My second summer in the U.S., I interned at Microsoft and made twice that amount in 3 months. I later had some well-paid tech internships and earned over 20X what I had sacrificed.
One yes. That's all it took.
Whether it's an admissions officer, a donor, or an early client—if the vision is good, someone will bite. Stay in the game long enough to find them.
2. IF YOU STILL HAVE IDEAS—AND BELIEF—KEEP GOING
Each cycle, I could tell there was more I could improve.
My SAT was mid (1230), and I clawed up to a 1450. Still not amazing—but better. I realized my recommendations could've been stronger, so I worked with teachers to write better ones, shared examples, taught them how US schools rated curriculum rigor (our system didn't prep them for that at all). I also "just did things" (businesses, flipping real estate, founding two edtech companies) to show I was a high-agency kid.
By the time I got in, I was running an Airbnb business in Uganda spanning 4 listings, 7 full-time employees, 13 contractors, and making ~$30K ARR with 2 ed-tech companies on the side (one that was going to transform college admissions in Uganda).
At that point, some wondered whether I still needed a degree. Maybe not. But graduating debt-free from college in the world's most powerful nation was a once-in-a-lifetime opportunity. And, given how everything's turned out for me, it was the right call.
3. SET A NUMBER OF NO's YOU CAN TOLERATE
This one's especially true when your dream requires external backers—investors, donors, etc.
Years ago, I watched Stephen A. Schwarzman's "Views From the Top" talk at Stanford GSB. He said it took 400 rejections to raise Blackstone's first fund.
Mind you—this was a Yale/HBS grad, MD at Lehman, straight white guy in 1985 (iykyk). I figured: as a Black immigrant founder with no Ivy League backing, I'd need to at least double or triple that.
So I did the math and picked my number: 1,000 rejections.
If I still believe in the vision and have any kind of runway (even if that means selling your car, your house—whatever you can afford to bet), I'm not stopping until I hit 1,000.
Whatever your version of this is—don't stop at 8 when you planned for 10.
You might be closer than you think.
If you're still reading, thank you for being part of this wild ride. Some days this feels like trying to keep a match lit in a hurricane. But it's still lit. And I'm still here.
Appreciate you all.
P.S. Whatever happens, we can say we tried. If I end up back in Uganda come August, applying to GSB with one hell of a story to tell, so be it. But I'm betting we'll have something far more interesting to show for these months of hustle.