Advice from VCs Anastasia Ashman and Pamela Day


September 11, 2017


Anastasia Ashman and Pamela Day during the Fall 2017 Berkeley Method of Entrepreneurship program
Anastasia Ashman and Pamela Day during the Fall 2017 Berkeley Method of Entrepreneurship program

Last month at the Berkeley Method of Entrepreneurship Bootcamp (BMoE), we had the chance to speak with two inspiring entrepreneurs and mentors — Anastasia Ashman and Pamela Day. They shared their personal journeys as entrepreneurs and innovators, provided valuable advice for starting ventures, and highlighted why they’re fans of the BMoE program.

Tell us a little bit about yourselves.

Anastasia Ashman: I am a global technology and digital media executive who specializes in the entertainment industries. I also serve as the operating manager for a venture fund. I’ve always loved startups – to be able to think about potential, to come up with news to do things, and to really spend time with people who think differently than myself. Well, there’s nothing quite like it.

Pamela Day: I like to say that I’ve always been a closet nerd. From when I was young, I’ve loved technology and proceeded to work in companies that have a close intersection between business and tech, such as at Levi where I looked into machine learning and AI opportunities. I worked on startups and have been there through both the booms and crashes, and discovered that I’m really a builder, not a maintainer. At the core, I love solving problems in a meaningful way.

A: Pam and I have actually been friends for a while. We met over Twitter and grabbed some coffee, and we haven’t looked back!

That’s awesome! Both of you seem like you’ve acquired such valuable experiences as entrepreneurs. Any advice for the rest of us?

A: I think too frequently people are scared of failure. But the important thing to recognize is that we learn the most from our failures. It’s important to experience these to figure out how to guide past problems so that the next time you face them you know exactly how to deal with it.

P: Absolutely. Following on that note, I feel like these days everyone wants to become a founder — it’s popular and looks easy. But it really doesn’t work that way. There’s a lot of hard work that is being put into every successful company. So, make sure that you love your idea and you love your team. Have enough heart and intellectual curiosity invested in your company so that you can spend seven years of your life solving that problem.

A: Another big concept that I wish more entrepreneurs were familiar with is empathy. It’s not the first thing you would think of, but it’s probably one of the most important concepts you need to practice as a founder of a company. Many times, the reason a product isn’t successful is that it wasn’t built with the user in mind. This is where empathy comes in play. Put yourselves in your user’s shoes, or better yet — talk to them. Be sure that you can understand your product from their perspective. At the end of the day, as a company, you should do the hard parts do that your user has it easy.

P: I couldn’t agree more. I love the concept of “empathic design” — it shows that you really respect your user’s time and that you care about them. Remember that as a user, you won’t give the company something unless they have given you something. It takes a lot of humility to make your product user-centered and to give up all the extravagances that you love. And don’t ever ask your relatives for feedback on your product.

A: Ever.

And what about from the flip side of the table? What are some key insights you’ve gained as being a VC?

P: VCs used to be unfriendly to founders, they would frequently cut the founders out of their own companies, so it’s awesome to see that culture shift. That being said, while it has become slightly easier to get funding, I think entrepreneurs forget an important piece of the puzzle. VCs have a hard job too — they aren’t getting money out of nowhere, this is money that is coming from their investors, real people who are saving up for retirement or for whatever it may be. So, I think one of the biggest pieces of advice I can give to all entrepreneurs looking for funding is respect the money. It’s as simple as that.

A: I agree with Pam. It’s a myth that getting the money means you’ve received the okay. Remember that when you are accepting funding, you are also accepting a relationship. I always like to say, don’t take money from someone you wouldn’t marry. Remember that even between the investor and the entrepreneur, you need to have a strong level of communication and respect. And don’t take more money than you need! This not only messes up your valuation, it also creates a toxic environment. People too frequently make the same mistake — they buy things they don’t need and scale far too quickly. This is a textbook mistake that causes money to go down the drain, and all because of a lack of discipline. Going back to what Pam said, be sure to respect the money — don’t waste it on things you don’t need.

That was such great feedback. As a closing question, what do you like so much about BMoE? What makes you come back year after year?

A: I love Gigi. She does a fantastic job of bringing the best people together. I don’t do this sort of thing — [mentorship and judging] — at other American schools. I think part of it is sentiment. After all, Berkeley is the city that launched me, and in a way, entrepreneurship brought me back. Entrepreneurship is a resilient way of life, and I want to be able to share my own experiences with these youngsters and to tell them how to avoid the same mistakes that I’ve made or seen in the past.

P: I think that you get a strong foundation from this Bootcamp that you can really apply to all parts of your life. Part of it comes from the idea that seasoned entrepreneurs share their failures so the next generation knows how to navigate them, but also the fact that there is such a short amount of time so the students don’t get bogged down by all the potential “issues” they think could arise.

A: I agree. And we come back to learn too! I love to surround myself with people who don’t know what I know. This means that my own assumptions are challenged, and I get to hear about what problems that people actually face. Every time I come to Bootcamp, I feel so inspired — everyone here is a dreamer and I like to carry that spirit with me everywhere I go.

Any last words?

A: You can do it.