UpCounsel was days from shutdown when a longtime user bought it to keep it alive

UpCounsel, an online marketplace connecting businesses with lawyers, had raised $26 million since its 2012 founding but was worn down by a 2018 lawsuit over fee-sharing with nonlawyers and a further 2019 shareholder suit for breach of fiduciary duty. In February 2020, after its founders and some staff moved to LinkedIn under a license deal, UpCounsel emailed users that it would shut down on March 4.

One of those users was entrepreneur Sieva Kozinsky, who had turned to UpCounsel years earlier after a $35,000 bill from a traditional law firm and estimated the service had saved him $70,000 to $100,000 over time. Kozinsky had just co-founded Enduring Ventures, a holding company built to buy struggling-but-good businesses and run them for the long term, modeled on Berkshire Hathaway.

Kozinsky and co-founder Xavier Helgesen quietly acquired what remained of UpCounsel, including its website and community of more than 10,000 lawyers, and announced the purchase in a March 31 blog post naming Helgesen CEO and Kozinsky interim CFO.

UpCounsel kept operating with its 10,000-lawyer community intact and became Enduring Ventures' first acquisition of a Berkshire-style buy-and-hold portfolio.

Kozinsky had firsthand proof the service worked, since he was a paying customer who had saved tens of thousands of dollars using it.

Enduring Ventures targeted businesses that were 'struggling for one reason or another' rather than growth-stage startups, so a distressed marketplace fit its acquisition thesis exactly.

The founders moved fast, closing the deal within weeks of the shutdown notice, before the remaining community and website value evaporated.

A struggling company's most loyal customers can be its best rescue buyers — they already know why the product is worth saving.

UpCounsel became Enduring Ventures' first acquisition, with the firm targeting three to four similar buys over the following year and describing itself as a long-term holding company rather than a venture fund.