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:

Carta

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). As of May 2024, the company is valued at $14B.

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. Nearly 15 years and $135B later, Tobi and Harley built Shopify into the defining e-commerce platform and one of the biggest SaaS success stories ever.

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 November 2025, they were valued at $5B.

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, September 20, 2023, and June 5, 2025 to include additional companies and provide current valuations.]