CEO of Zuckerberg Media and an active investor and advisor, Randi brings a wealth of experience and expertise to Republic. Together, we'll work to bring access to capital to underestimated founders, engage and educate new investors, and further our mission of bringing profits to the people. As an advisor, Randi will evangelize crypto, expand our dealflow, and provide marketing mentorship to Republic and our companies.
Randi has invested in over 50 startups and sits on the board of directors for The Motley Fool and Life360. She's a radio host and author of multiple books, and has been recognized with an Emmy nomination, a Tony Award, and much more. Randi was also an early employee at Facebook, where she is best known for creating Facebook Live.
To learn more about Randi's investing journey, check out her recent Q&A with Lisa Carmen Wang, founder of Sheworx and Republic's own Head of Brand and Communications.
What was it like starting your investing career?
I spent my entire career in Silicon Valley feeling like I was the only woman desperately clawing my way up to get the same kind of respect as my male peers. The guys around me were angel investing years before me and they came with this natural network. It wasn't until a few years after I left Facebook that I started thinking, “You know, I have this great expertise in social media and technology. Why shouldn't I be in those deal flows?”
What were some early lessons you learned?
After doing this for a decade, I've learned it's much more about the founder. Ideas change and companies pivot, sometimes a dozen times. In fact, I don't think I’ve ever invested in a company that five years later looked the way it did when they pitched me. It's really about the founder – their passion, grit and enthusiasm.
I also learned to make investments in fields I know about. I have three main buckets that I focus on where I can be a financial investor and a value-add investor.
What do you mean by value-add investor – what does that look like to you?
People believe a myth that you need to have money to be an angel investor. There are countless ways to be helpful without writing huge checks. You can open your network to a founder – these introductions can be huge.
Your expertise is also incredibly valuable. When I meet with an entrepreneur, I'm walking into the room with 15 years of expertise in social media and working directly with founders and entrepreneurs.
There's also the intangible support you give an entrepreneur when you sign on. Entrepreneurs get rejected so many times, a “yes,” even a small one, can give an entrepreneur confidence. That's something you can’t put a price tag on.
A lot of people have Impostor Syndrome when investing. Are there ways investors can make a difference in the life of an early stage company?
Absolutely. To start a business, all you really need is a laptop and internet connection. Your first angel investment doesn’t need to be to startups like Peloton or Tesla that need to raise millions to build actual machinery; you can make a huge difference with a tiny check to someone who's starting an e-commerce company that doesn't need much money to get off the ground.
You only learn by doing, and angel investing is one of those things you learn by getting your feet wet.
I think about it as scaling myself. I could put all of my work into one startup, but diversifying a portfolio is a more surefire way to success. I always advise people to figure out how much money they can realistically invest and to spread that over 5-10 different investments. It's all about your portfolio strategy, and it can be really exciting to support multiple entrepreneurs while decreasing the pressure of your investment. It just takes one to be successful.
Tell us about your due diligence process? How do you go from a pitch to “yes, I'm ready to invest?”
While there needs to be the right balance between the concept and the founder, for me, it’s much more about the founder. I want to make sure that when the going gets tough – which it will – that they have the grit and the passion to get through the challenges. I need to walk away from the meeting feeling like it’s the founder’s life work to solve the problem.
Some of the best investments I’ve made were in entrepreneurs that were underestimated. For example, my first great angel investing outcome was in a company developing a smart breast pump. They could barely get a meeting with traditional (mostly male) VCs. I had just had a baby and I figured half the population is also having these issues, so I wrote them their first check. A few years later, they were purchased by Mandela. There’s a huge opportunity to invest in entrepreneurs who might otherwise be invisible or unable to get into the system.
What advice do you have for women who are interested in getting into investing?
Try to learn as much as you can before dipping your toe in. Also, I've had a lot of success co-investing with other women. In fact, I almost always do this. Chances are, if another smart woman is willing to put her money in a deal, we are making a good decision together.
There are so many great resources to help women get into investing. The more women who put money into the system, the more decision making power we have. We need to be putting money in if things are going to change.
One area where women can make a big impact is in blockchain. What are your thoughts on the future of that industry?
I'm so excited about the crypto and blockchain space. I was tired of seeing women banging their heads against the wall trying to get into male-dominated spaces and traditional tech fields. Crypto was this whole new industry where we could get in on the ground floor. I almost worry that too much of the conversation around diversity in tech is about how we break in. We're ignoring the fact that there are all of these new emerging fields that are wide open and that we're all learning about together. If we don't get into these industries today, we're just going to be having this identical conversation 20 years from now. This is a space where we can get ahead of this issue.
How would you advise someone who wants to learn about blockchain? How do they get started?
To start, listening to podcasts or reading a book will catch you up. When I started, I knew nothing about crypto or blockchain. When I was asked to give a one-hour speech on it I thought I should say that I knew nothing. Instead, I saw this as an opportunity to learn. So I spent several hours listening to podcasts. I called people who were working in blockchain startups and asked questions. By the time I was done, I had a really solid understanding. I gave that keynote, and it was successful.
My next step was to start angel investing in some blockchain startups. I invested in a theater company that was using blockchain to stop second hand ticket sales for shows like Hamilton. I put money at stake so I had to understand blockchain.
It’s about getting involved in the industry, step by step. I learned from scratch – so can anyone!
As you look at the future of blockchain where do you see the biggest impact?
I think decentralized finance, in general, is exciting. I'm very lucky to be in the US where we generally trust our financial system and trust that our money will retain its value. If we truly think technology can improve people's lives, then we need to be thinking about the billions of people who are unbanked and who can't trust their country's financial systems. For me, that's what makes decentralized finance such an incredible opportunity – not just for us, but for entrepreneurs and people all over the world.
Are there any other industries or types of investments that you are most bullish on going forward?
A new category that I've started getting interested in is education. I always knew that education was ripe for disruption. After my three children were homeschooled for a year because of COVID, it really reminded me that we rely on traditional schooling for way too many things, and when that goes down, everything else does too. We also can’t afford to lose more women in the workforce because of homeschooling. It’s an immediate need to fix.
When you approach investments in industries that you're interested in, do you have a specific solution in mind, and then search for a company that's doing that? Or do you know the problem you want to solve?
A little of both. The honest answer is that none of us really know what the world will look like in another year or five years, so I want to make sure that I'm working with entrepreneurs that are open minded enough to shift and pivot as the world changes, not entrepreneurs who have blinders on and who think this is the one way we solve this problem. All of us need to be creative and resilient and solve these problems together.
Are there any last takeaways you'd like to leave our audience with?
The best time to start something was 10 years ago; the 2nd best time is today. Don't waste time thinking – just start investing.
This is one of the reasons why I love equity crowdfunding. Gone are the days that you need to be writing $50,000 checks – for $100 you can be an angel investor. There's really no reason we can't all just get started today.