ApplyBoard's $3B Missed Investment

Shaan tells a story about missing out on a major investment opportunity in ApplyBoard, which would have turned $25k into tens of millions.

"Back in 2015, I met this 13-year-old kid who used our app every day. I gave him a homework assignment to be my scout and send me companies I should invest in. His second recommendation was ApplyBoard, which helps international students find and apply to universities.

The kid wrote this amazing analysis: they had 11 schools contracted to pay commissions, 14 more in the pipeline, 1,500 students signed up, 160,000 Facebook likes - all with just $10 in paid marketing. Their customer acquisition cost was only a few dollars with a $1,000 lifetime value.

I took the meeting with the founder Martin, who was incredibly charismatic. I loved the business model - colleges were charging international students 2-3x more than domestic students, and ApplyBoard would get $3,000 per student they placed. I committed to invest, but when he started raising the round and getting some nos from other investors, I started doubting myself.

When it came time to write the $25k check, I froze. I was making $160k a year, and this would've been my entire savings. Instead of finding a creative solution like writing a smaller check or bringing in other investors, I just ghosted them.

Fast forward 5 years, that same kid emails me: 'Remember ApplyBoard? They're a unicorn now.' The company is worth around $3 billion. My $25k investment would have been worth tens of millions of dollars today, all because I let fear override my conviction and couldn't figure out how to make it work."