In January 2016 we were investing via our second fund, and Airwallex co-founder Jack Zhang contacted me about their “online multi-currency wallet”.

Despite being referred to me by a trusted source - Pay Pal alum Peter Davidson - I rejected Jack’s email pitch without even taking a meeting, citing my lack of personal connection to the problem.

Jack perservered, attending our Sunrise event a few months later, where I fumbled again by not talking to him.

When we finally met him in July 2017, my colleague Nick reported on our #_urgent Slack channel that "Jack from Airwallex is a WEAPON”.

Too late. Cut to 2021 and Airwallex is valued at $2.6B.

- Niki Scevak

As told to Oughtfolio. (There's also a Twitter thread.)

(See Square Peg's Airwallex investment notes on Thoughtfolio.)

One of the anti-perks of being a VC is that after a few years in the job, you’ve accumulated so many mistakes (which you’re constantly being reminded of) that you can’t help feeling like a f***ing idiot.

Case in point:

Talked to them today. Very interesting product/market. Great pitch/presentation via Skype. But they are months away from product launch and want a note with $8M cap, and need a decision really soon.

This is me passing on Canva. (－‸ლ)

They’ve just raised at a $15B valuation. Even more impressively, they’re at $500M ARR, growing 130% y/y. Huge kudos team @canva!

- Christoph Janz

In 2009, Salesforce alum Freddy Kerrest and his co-founder Todd McKinnon grabbed lunch with Byron Deeter to tell him about a company they just founded, SaaSure.com.

While Byron believed in their product vision, it was still the early days of SaaS and turning web apps into an intelligent and integrated Cloud Area Network seemed far too complex.

Today, Okta is a leader in cloud access management with a market cap over $14 billion.

(See Bessemer's Auth0 investment memo on Thoughtfolio. They missed Okta but got Auth0, which was later acquired by Okta for $6.5B.)

We looked at this company multiple times and came very close to investing, but unfortunately, we always eventually passed it up for a number of reasons!

We had seen far too many offline cab companies and were concerned that scaling this business would require a huge quantum of capital.

Further, on the unit economics, we had significant concerns that this space would bleed for a very long time and found it hard to understand how the space would become significantly margin positive.

Lastly, we saw a lot of regulatory friction in India which we felt could be binary (Uber was still very tiny).

- Niren Shah

We had the chance to invest in the Series B of Shopify in 2011.

This was not our early-stage sweet spot and the $100M valuation felt rich.

Eight years and $49.9B later, Tobi and Harley built Shopify into the defining e-commerce platform and one of the biggest SaaS success stories ever.

(See Bessemer's Shopify Series A investment memo on Thoughtfolio.)

In 2006 Byron Deeter met the team and test-drove a roadster.

He put a deposit on the car, but passed on the negative margin company telling his partners, “It’s a win-win. I get a great car and some other VC pays for it!”

The company passed $30B in market cap in 2014.

Byron paid full price for his Model X.

Travis pitches Uber (Ubercab) raising $1.5m at like a $4.5m pre. I scratched my head thinking “taxi lobbies will crush them" - @chrisfralic raises his hand on the spot and says “I’m in for $500k.”

He’s retired now. I’m not. #TrueStory

- Mark Suster

(See Lowercase's Ubercab seed investment notes on Thoughtfolio.)

Should have invested in Coinbase at the seed. What a miss.

Simply would have had to turn down Avicii in my dorm room, kick friends out of the pre-game, make some money, develop a network, learn about bitcoin, then google what a seed round was.

Tough miss to swallow.