The Most Important Lessons Learned in My First Year at UpWest

The Most Important Lessons Learned in My First Year at UpWest

UpWest is an extremely unique fund. Our investment approach is niche, to say the least, filling a very particular gap in the US-Israel technology junction. Honestly, when I was first connected with Gil Ben-Artzy about joining the team, I thought I was interviewing to work at an accelerator (I was wrong). Instead, in May 2017 I joined an early-stage VC fund that has given me invaluable, hands-on experience working directly with entrepreneurs and helping them establish their footing in Silicon Valley.

Fast forward one year: I have learned so much from UpWest Founding Partners Gil and Shuly, and even more from working with our entrepreneurs. Here are the biggest lessons I’ve learned:

Be open to meeting anyone

One of the first things I was told when I joined the UpWest team was that “we meet every entrepreneur.” That sounds like a VC bragging about how many startups they meet, but it is actually something entirely different; it’s a mindset that guides how we engage with entrepreneurs. At UpWest, we genuinely want to meet anyone starting a company. For us, there is no such thing as “too early” in a company’s journey for us to talk. It also doesn’t matter if you find us through a warm intro, or by sending a cold email to — in fact, we just recently invested in a startup who reached out via social media. Most importantly, we want to meet entrepreneurs of all backgrounds and experiences. VCs often rely on pattern recognition, but my experience at UpWest has shown that there is no such thing as a blueprint for a successful entrepreneur.

If you are passionate about the problem you are solving, we want to know about it. Building a company is extremely challenging, and we are in the business of helping founders navigate that process. Of course, we help by investing in startups. But we also take meetings every day to just offer advice and feedback to founders who are unsure of what the next step should be for their business, or individuals who are just beginning to toy with the idea of starting a company. This guiding principle of meeting everyone — regardless of who they are — runs deep in our blood. It’s all about helping the entrepreneurs.

Face time with founders is critical

Despite moving to Tel Aviv from New York, I spend significant time in Silicon Valley working directly with the CEOs of companies we have recently invested in. That time in Palo Alto is where the magic really happens.

After UpWest invests in a startup, the expectation on our end is that the founding team (or at the very least, the CEO) will come join us in Palo Alto for an initial 3-6 months, with the understanding that the CEO will then establish her headquarters in the US. What makes the UpWest experience so special is how deep we engage with our entrepreneurs, beginning with these initial few months. For me, that means flying out to Silicon Valley a few times per year and literally living with the founders in a house in Menlo Park. In case you’re wondering, it’s awesome.

Living and working with our founders in Silicon Valley is what has taught me the most valuable lessons that best inform my work as an investor. So much of growing a company is what happens outside the office: talking through your challenges with other entrepreneurs who can empathize; staying up until 2AM working on a customer or investor presentation; forgetting to eat meals because you’re just too damn busy (or alternatively deciding to go the Soylent route in the name of efficiency). Being a part of that journey lets me see what is and isn’t working for our companies. Face time is key.

It’s easier (and more valuable to a founder) to help correct a problem if you’re in the same room when it happens, rather than waiting to address it at your next monthly investor update.

There is no substitute for proximity

Since I joined UpWest, we’ve made seven investments. Almost all of those companies have changed direction (at least slightly) since going to the US. This is part of every early stage company’s journey, but the changes happen much faster for founders in the US than in Israel. The only way to know what works in your market is to go there. This is true for entrepreneurs and it’s true for investors. I say this specifically focused on the US, but the lesson holds true for companies targeting Europe and China as well.

When I work with our teams in Palo Alto, I see how their US customers react to a sales pitch or to a product update. I also get to keep a finger on the pulse of technology trends coming out of the Bay Area. We love to boast that Israel is the startup nation, but it is not the epicenter of global technology. Being in the Valley for extended periods of time, I learn much more about what technologies American VCs are funding, and what innovations are actually driving US corporates forward, versus when I am a 10-hour time difference away in Tel Aviv.


I learn new things every day from our amazing team, our founders, and the new entrepreneurs whom I meet on a daily basis. I am extremely fortunate to wear two hats, identifying promising startups in Israel and then helping those teams execute on their goals in the US. Both roles inform one another, making me a better investor. Understanding what early stage companies face in the US market helps me source investments just as much as it gives me the opportunity to help our founders work toward successful outcomes.

I’m heading back home to Tel Aviv now after an extremely rewarding two months in the Valley. I’m excited to hit the ground running, and look forward to meeting more of Israel’s strongest founders. Yalla!

Lia Cromwell, Associate, UpWest

PS – I meant it when I said we aim to meet with everyone. You can reach me at