Founder Interview with Philip James, Founder and CEO at Penrose Hill


Blog, News

By Tribeca Venture Partners
Philip James, Founder and CEO at Penrose Hill

Philip James is the founder and CEO of Penrose Hill, one of the largest wine producers in the US, selling wines around the world through multiple channels, including via its Direct to Consumer website, Firstleaf. Philip is a serial entrepreneur who has built a career combining cutting edge technology, consumer insights, and the talents of world-class winemakers to create and deliver finely crafted wines at an affordable price point.

Tell us about Penrose Hill and why you started the company?

I’ve spent my whole career helping customers understand and buy wine more easily. Each company I’ve started has kept this customer focus, while each has moved further up the supply chain. At Penrose Hill, we work with vineyards around the world and are making wines that we know our customers will love because we are using their feedback to inform our purchasing and production decisions. We are a winery and we work with vineyard partners across different regions, which allows us to source the most interesting wines, at the best prices, from around the world. 

Penrose Hill recently announced its 1,000th Wine Award and the LA Times Wine Club partnership (Congratulations. Where are you keeping all these awards?). Can you tell us more about the success of your brands and partnerships?

We now have almost 1,200 awards, and you can see them all for yourself here One of our wines, the Posted Accord Chenin Blanc from South Africa, recently scored 98 points at a prestigious Sonoma awards show. The wine was even named Best in Class, beating much more expensive wines to receive the highest score awarded at the event. Our focus is the customer, but the critic accolades are a nice validation of our customer-centric model. 

Our unique winemaking focus has allowed us to build a roster of high-scoring, delicious wines. The 97 point Disorderly Conduct, 96 point Common Phenomena, and “Best of Show” Isolde’s Rapture are just from our portfolio of California wines, and it’s wines of this caliber that allows us to build successful partnerships. California is a wine lover’s paradise, so partnering with the Los Angeles Times (a publication known for its food coverage) made a lot of sense to us. One of the best parts of the partnership has been our collaboration on events. Just a few weeks ago I was in LA for a great event pouring our wines and meeting new members of our club.

What’s been the most important milestone for you and the Penrose Hill team?

The most important milestone has been our decision to invest in our winery and winemaking. We always made good wine, but over the last two years we’ve raised the bar several levels. First, by working with one of the few Masters of Wine winemakers in the country, and then by investing in our own tanks and lab. Our whole winemaking team works in the lab and they have taken our wine from good to great.

Our TVP Founders and CEOs tell us there are so many lessons in entrepreneurship. What’s the biggest lesson from your Penrose Hill journey? 

The importance of clear communication, which gets massively more complicated as the team grows (ie. Metcalfe’s Law!). Now that we have multiple offices, both here in the US, and abroad, I spend an ever-larger portion of my time saying fewer, but more specific things. It’s how I can ensure that we are all focused on the same key priorities.

AlleyWatch named you a “2019 NYC E-Commerce Influencer”? (Congrats, Again). Tell us more about the impact or influence you hope to have on NYC Tech?

Thank you! NYC Tech is a close-knit community. For me, the best result is seeing people who used to work for me going on to great success elsewhere, and, in particular, those who go on to be founders. 

What’s your advice on what an entrepreneur should look for in an investor?  

First of all, it’s difficult, because most entrepreneurs just want to close the fundraise as fast as they can. However, it is very important to remember that you will be in partnership with your investors for many years. It’s important to take a step back and assess what you need as a founder so that you can align with the right VCs. If you’re looking for money now and possibly a lot more later, that’s very different than if you think you just need to raise this money and then get to profitability. 

How do you deal with failure or setbacks as you build a startup?   

Setbacks happen every day. I learned how to shift my focus and go do something else. If I’m stuck somewhere, I take a break and focus on a milestone with another aspect of the business. This helps with the founder’s state of mind and gives you something new to use, that could help with the original problem. 

What are your Top 3 recommendations for Penrose Hill wines for the holiday season? 

We have a couple that I would recommend as perfect for the holidays: the Common Phenomena 2018 Chardonnay-Sauvignon Blanc (from Russian River Valley, a premier wine region in Sonoma that just got 96 points and a Double Gold), the Bodewell 2017 Pinot Noir (will please almost everyone and is great with food), and for the dark red wine drinkers the Harmonic Bridge 2018 Barbera

How do you balance being a CEO with everything else in your life?

The way I have structured the company is all about ensuring that the whole team is aligned. Every employee has simple goals, and the whole company can see each other’s progress. That transparency gives the team the freedom to work how and where they want. I travel a lot, domestically and internationally, and the autonomy I’ve vested in the team gives all of us (myself included) the freedom to design our own schedule. I can travel for work or for pleasure and still be productive. No matter where or when we are working, I know my team is focused on the right things. 

What are you currently reading/aspiring to read this fall?  

I read a lot across all formats (digital, audio, and real books still). Two I just finished were:
The Pioneers – The Heroic Story of the Settlers Who Brought the American Ideal West

by David McCollough – The title sums it up. It shows just how tough and full of optimism the American settlers were, and you can still see the effects of that era even today. 

The Messy Middle by Scott Belsky – Scott is an angel investor in Penrose Hill. He was a founder, had a successful exit, and is now a VC. Again, a clear title. Everyone likes to hear about how a company was started or how it ends up, but Scott dives in and helps the reader make sense of how to fix the hardest part of any business, which is the day to day in between.   

Words to live by…

“Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom” by Viktor Frankl, Man’s Search for Meaning.