Nine Years of Upgrade: A Letter to Myself in 2017

Tinu,

It’s 2017. You have about five thousand euros, no office, no product, and a sentence you said out loud to your roommate a few months ago: I’m going back to Romania to do something in education. You still don’t know what the something is. Tomorrow you’re going to walk into a classroom at Tudor Vianu and find out.

Twenty-six kids will sign up. Nine years from now there will have been more than 1,500 of them, a mentor network of 150-odd Romanians at the universities they’re trying to get into, a book, a funding round, and a quantity of mistakes I’m not going to list because you’ll make most of them regardless. A few things, though, in case any of it lands.

You’re going to want to launch a school. Don’t. What you can afford is a course. Run the course. One room, one cohort, you doing everything, including the invoices. It’ll feel small and it’ll be the best research you ever do, because those 26 will teach you what parents pay for and what students show up for, and how far apart those two things are. Every founder you meet later will want to skip this stage: raise, hire, then discover the product. You’ll do it backwards because you’re broke. Later you’ll wish you’d done it backwards on purpose.

Be careful what you promise. The pitch you’re about to write — “we increase your chances at top universities” — is true, and it will build the brand. It will also attract a particular kind of family, the kind for whom “chances” means “guarantee,” and for whom a rejection from Oxford is a broken product rather than a competitive outcome. You cannot take a promise back once it’s in the market. I’d sell the thing you actually control: the quality of the thinking, the quality of the work, who the kid becomes. Admissions are downstream of that. They are not the product. You’ll figure this out around year six. Sooner would be nice.

The mentor is the product. Everything else, the platform, the curriculum, the sales deck, is packaging. Every time you grow faster than your ability to find and keep excellent mentors, quality will slip, and the slip shows up eight months later as churn and one-star reviews. Every time you slow down and get picky, it recovers. You’ll relearn this three or four times. Also: someone who has walked through the exact door — Cambridge law, not “the UK” — is worth three generalists. You’ll rebuild matching around that after the round. It’s the change I’m proudest of and it took too long.

Money changes the question. In 2021 you’ll raise a seed round — SeedBlink, a few funds, some angels including the WHOOP co-founders, which you’ll still find slightly unreal. Be grateful. Also notice that the question in every meeting will shift from is this good to is this big. Different questions, different answers. Romania is a small market for selective admissions; that’s a fact, not a verdict. What you haven’t done yet is decide what growth you actually want: more countries, more products, or more depth here. Decide before you take the money. I didn’t, entirely, and it cost some friendships and a lot of sleep.

You’ll rebuild the team more than once. Each time it’ll feel like the fix. Each time, a year on, the same problem will be back under a different name. The problem is never the people. It’s that you didn’t fix the thing upstream, usually the mentor question, sometimes the promise question, and new hires inherited the old structure. If you find yourself doing a “reset” for the third time, stop resetting and go find the thing you keep not fixing.

At some point ask whether you’re doing good, and take the answer seriously. Most Romanian kids who dream of Harvard will not get into Harvard. Statistically that’s just true. Somewhere around year seven you’ll wonder whether you’ve been selling a dream that leaves most of them feeling they failed. Sit with it. Don’t rush past it. The answer you’ll reach is what Upgrade is becoming now: the things that get a kid into a top university — thinking for themselves, doing what nobody assigned, arguing a position and then changing it — are worth having whether or not the letter arrives. Teach those and you’ve done good regardless. Teach only the application and you haven’t. It’s a less exciting pitch. It’s the true one.

One more, and then I’ll let you go to Vianu.

Come back anyway. Investors will say no. Friends will call it a step backwards, some to your face. For a couple of years you’ll compare yourself to former colleagues buying apartments in New York and feel like you threw it all away. You didn’t. What you found is a problem worth nine years, in a place where almost nobody else was working on it. That’s rarer than the salary. I’d take the trade again. I think. Ask me in another nine.

— T.