“When you know, you know”. This saying is true for many things in our personal lives but it also holds for when investors meet very special entrepreneurs.

I was first introduced to Jaleh and her co-founder Nikhil by our mutual friend Adam Nelson who had studied with her at the GSB. Jaleh was employee #12 (and the first marketing leader) at Gusto and had seen first-hand the gap in growth marketing tools for modern SaaS startups. So, with Nikhil and a growth engineering team, had built a bunch of internal tools to fill the gaps.

Mutiny co-founders Jaleh Rezaei and Nikhil Mathew

At Uncork, we love the…


Confession time: I’d actually meant to finish (it’s been in drafts for like three years) writing this on my fifth anniversary at Uncork Capital (née SoftTech VC) but like so many things in the early days of the pandemic it was put to one side in favor of trying to figure out stuff like how bad things might get in the early-stage fundraising landscape (barely at all, as it turned out), how on earth to get a three-year-old to participate in “distance learning” (impossible) and how many Zoom happy hours in a week were too many (four). Weeks turned to…


Like most investors, we spent the early part of Q2 focusing on our portfolio — helping founders with planning for the “new normal” we all found ourselves in, figuring out runway and where to cut costs, as well as weighing potential bridge financings.

However, by late April we began to find that with plans in place, most of the portfolio was in “execution mode” and our calendars began to open up enough to take a few initial meetings with interesting-looking startups. Bear in mind that at the time we had no idea how the pandemic would affect the startup ecosystem…


Every so often you witness a product launch that captures the imagination of its intended audience, and very, very occasionally you have the good fortune to be involved in some small way. Last week we were excited to announce our investment in Tailscale as they pushed their product into general availability.

For the uninitiated, Tailscale is a new mesh network security product that uses the “zero trust” principles popularized by Google’s BeyondCorp project to secure each node in a network versus just the perimeter. But what does that mean in practice? …


SaaS (Software-as-a-Service) is everywhere. According to a new report by KBV Research, the global SaaS market is expected to attain a market size of $185.8 billion by 2024, growing at a CAGR of 21.4%. SaaS now touches almost every aspect of the modern business, regardless of industry, location, size, or company age. Amazing tools are available to do literally everything from helping startups manage their communications and people, via allowing agencies streamline their client processes and billing, to specialist products to drag hundred-year-old industrials into the 21st century. …


There is a small but elite group of founders in the Uncork family who decided to not only take another ride on the new company rollercoaster but also graciously allowed us to back them for the second time. This list of intrepid souls includes Manish Chandra with Poshmark; Jessica Alter with FounderDating; Jack Abraham with ZenReach; Jonathan Abrams with Nuzzel; and — with our most recently announced investment — Bob Moore with Crossbeam.

Jeff backed Bob’s first startup RJMetrics back in 2010 and worked with Bob and co-founder Jake Stein through the highs of early growth and follow-on fundraises, the…


Conventional wisdom in our industry says that cold emails generally don’t equate to great deals. Most VCs (including us) put a great deal of emphasis on our network — upstream investors, potential syndicators, accelerators, our family of founders and execs — referring deals to us. This makes a lot of sense in most cases as great people tend to know great people, and folks we trust will (hopefully) bring us great opportunities.

However, there is risk in being too myopic on this front — our network certainly isn’t universal and we simply can’t be connected to every great founder. Despite…


This past Wednesday was not my favorite day ever — England crashed out of the World Cup with a subpar performance against a gutsy Croatia; I had to watch the game on a cramped United flight (which was delayed and the wifi was down); and at 8pm I found myself in Cleveland, Ohio. Joy.

This newsletter piece isn’t a reflection on another poor experience flying United, nor is it about trying to find a decent place to eat on the outskirts of Cleveland (whilst trying to keep a toddler who hasn’t napped all day amused). …


As a founder, it takes guts to admit that your company isn’t working. It’s all too easy to believe that with just another month of cranking things will improve — your sales conversations will convert better, your margins will improve, or your marketing channels will start producing. Too many founders wait too long to hit pause, often because they still believe it can work. Just a little more time, more funding, more something.

We invested in FirstLine Medical, an on-demand urgent health care provider, at the end of 2015 for a number of reasons — strong leadership with a deep…


Until relatively recently, if someone were to ask for your opinion on the “The Edge” you’d probably default to talking about why he’s no Bono but U2 really couldn’t function without him. However, over the last couple of years there has been an increasing buzz around a different Edge, “Edge Computing”.

Not this Edge, silly

In a nutshell, this non-U2-related Edge refers to pushing large amounts of compute down from the cloud (so 2016, darling) to the devices themselves. From the center of a theoretical network diagram to the edge.

So why is this a thing, given we’ve all been so excited about cloud…

Andy McLoughlin

Partner at Uncork Capital (formerly SoftTech VC). Previously founder of Huddle and angel investor. Brit in SF. Probably taller than you. Tech. Whiskey. Music.

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