Bessemer started the idea of the “anti-portfolio” – the companies that you passed on, but ended up doing very, very well. 

Here is the Version One anti-portfolio that we have built over the past decade:

ApplyBoard

We met CEO & co-Founder Martin Basiri in February 2016. Despite his passion for helping international students get into universities and colleges in North America, and having incredible traction early on, we passed because we weren’t comfortable with a high AOV / one-time “purchase”. As of September 2020, the company is valued at $1.4B and has helped 120,000 students identify and apply for 1,200 schools abroad.

Carta (prev. eShares)

We were introduced to Henry Ward from eShares through our friend Manu Kumar from K9 Ventures in 2013. We loved the product, but weren’t convinced it would get much distribution quickly. We were also worried about how much people would pay for it (if at all). Carta went on to become the standard for cap table management and is a unicorn many times over. 

Honey

We had a chance to invest in a $500K round at a $12M valuation in 2015. We loved the founders, but didn’t have much conviction around the scalability of a browser plug-in and the fact that this was a bridge round. And yeah, $12M felt kind of high :-). Outcome: In November 2019, Honey sold to PayPal for $4B (PayPal’s largest acquisition ever at that time).

Instacart

We talked to Instacart’s founder Apoorva Mehta after the company went through YC in 2012. Anyone who has ever spent time with Apoorva knows how smart he is, but we were too focused on how how operationally tough it would be to build up such a shopping delivery network. Instacart became a public company with a market cap of over $10b in September 2023.

ScaleAI

With an intro from our good friend Morgan Beller, we met co-founder Lucy Guo at an In-N-Out Burger in July 2016 when the company was going through YC. We had a difficult time wrapping our heads around how to scale a human capital intensive business (i.e. data labelling with mechanical turk). In just 5 years, the company is now valued at $7.3B and is on track to hit an annual run rate of $100M with customers like PayPal, Pinterest, and the US Air Force.

Shopify

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. Ten years and $170.9B later, Tobi and Harley built Shopify into the defining e-commerce platform and one of the biggest SaaS success stories ever.

Sonder (prev. Flatbook)

We met Sonder’s founder Francis Davidson many times between 2014 and 2016. And, we passed on the opportunity to invest every single time as we were too hung up on their dependency on AirBnB for distribution. In April 2021, Sonder announced that they were going public via a SPAC at a $2.2b valuation.

Wealthsimple

In March 2014, Michael Katchen pitched us the idea of bringing Wealthfront to Canada: Wealthsimple would be an online financial advisor that makes investing easy, accessible, and affordable. We passed on the opportunity because we assumed that the Canadian market would be too small for a venture-like outcome – boy, were we wrong: Michael went on to aggressively build up the asset base and add additional products like stock trading & banking services to the platform. In April 2021, they were valued at $4b.

We are sure we have since passed on many start-ups that we will have to add to our anti-portfolio over the next few years. Early-stage investing is not easy and we make a wrong decision every day! But, this list should be a confidence booster to every entrepreneur that gets a no from an investor. Early-stage investors are more wrong than right. A “pass” means absolutely nothing about the future success of your company!

[The original blog post on the Version One anti-portfolio was published on Dec 3, 2019. We have updated the post on May 18, 2021 and again on September 20, 2023 to include additional companies and provide current valuations.]