Matthew Le Merle is the Co-Founder and Managing Partner of the Fifth Era and Keiretsu Capital, one of the most active early-stage venture investors backing almost 200 companies a year. They’ve backed over 20 unicorns, including Airbnb, Spotify, Coinbase, and many more.

Matthew has advised leading companies, including Amazon, Cisco, eBay, Google, HP, Microsoft, on growth and innovation. He’s an economic value creation expert that has helped drive annual savings of over $2 billion at a leading retailer and $1 billion at a leading bank.

He has written several books with the latest one being The Intelligent Investor – Silicon Valley: Practical Wisdom for Investors and Entrepreneurs from 50 Leading Silicon Valley Angels and Venture Capitalists which he co-wrote with Alison Davis.


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Here’s a glimpse of what you’ll learn:

  • Why Matthew Le Merle wrote the book, The Intelligent Investor – Silicon Valley: Practical Wisdom for Investors and Entrepreneurs from 50 Leading Silicon Valley Angels and Venture Capitalists with Alison Davis
  • What makes early-stage investment different and how investors determine the value of an early-stage startup
  • Matthew talks about his career and why he became a full time investor
  • Matthew explains why his significant misses were an indication that he was fishing for the right investments in the right pond
  • Matthew talks about what Michael Moritz said about the book he co-wrote with Alison Davis
  • Matthew’s earliest, most influential investments that helped him understand the value of the internet as an investment opportunity
  • Emerging opportunities that Matthew sees in the current investment environment
  • What is the Fifth Era and how they view investments
  • How can technology redesign the educational process for everyone?

In this episode…

Early-stage investing is difficult and often very risky–many people have invested their money in the wrong start-ups and ended up losing money. But what if there was a way to avoid and minimize losses in early-stage investing? And more importantly, what if there was a way to connect the dots to spot potential unicorns before most people do?

On this episode of Inspired Insider, Dr. Jeremy Weisz sits down with Matthew Le Merle, Co-Founder and Managing Partner of the Fifth Era and Keiretsu Capital, about investing in early-stage companies and how rewarding it can be. Matthew shares how investors determine the value of an early-stage startup, where the next opportunities could be today, the importance of fishing for the right investment opportunities in the right places, and how Fifth Era views the changes in society today. Stay tuned.

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Episode Transcript

Jeremy Weisz

Dr. Jeremy Weisz here, Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders and Matthew I have some interesting folks that you should check out that people should check out other episodes I had Jon Medved that started OurCrowd. And, you know, oftentimes some of the investors VCs, I like to ask what their biggest mistake was. Because you, there’s so many deals that come across your plate, you can’t get them all and he talked about early on. He had the opportunity to invest in Salesforce really early on, and he passed on it. And so Fabrice Grinda talks about his meeting with Snoop Dogg and some other rappers in his early venture, now he does investing as well. And before I introduce today’s guests, which excited about this episode is brought to you by Rise25, which I co founded with my business partner, John Corcoran. At Rise25 we help businesses give to and connect their dream 100 relationships. And we do that by helping you run your podcast. And the number one thing you know, Matthew, my life is relationships. And I’m always looking at a way to give to my best relationships in a podcast over the past over 10 years has allowed me to profile others their thought leadership, and really the people I admire what they’re doing in the universe. So if you have questions, and you’re thinking about starting a podcast, go to Rise25.com, and you can email support at Rise25media.com. I’m super excited about today’s guest, we have Matthew Le Merle. He’s the Co-Founder and Managing Partner of Fifth Era and of Keiretsu Capital. And it’s the most active early stage venture investors backing almost 200 companies a year. They’ve backed over 20 unicorns, including Airbnb, Spotify, Coinbase, and many more. Matthew has advised leading companies including Amazon, Cisco, eBay, Google, HP, Microsoft, and even more than that on growth, innovation. And he’s an expert in economic value creation, and Matthew I was reading about you. You even helped drive annual savings of over $2 billion, at a leading retailer and $1 billion also at a leading bank. And it’s just, when I do these intros, it’s like, I try and make them short. But if there’s too many good things, it’s hard for me to make them short. But um, you did all this with your wife while raising five children, which is a feat in itself. And people should check out the books you’ve written. There’s one with you, and Alison Davis, The Intelligent Investor, the Silicon Valley, practical wisdom for investors and entrepreneurs from 50 leading Silicon Valley angels and venture capitalists. So, Matthew, thanks for joining me.

Matthew Le Merle

Well, thanks for having me here. Jeremy, I’m looking forward to it.

Jeremy Weisz

What made you decide to write that book?

Matthew Le Merle

Well, so for us, this journey has gone from being consultants through to being investors and advisors. And that transition requires a lot of learning. And we love it. You know, we’ve been in Silicon Valley, 35 years, and we just love being part of the innovation ecosystem. We love the passion and ambition of entrepreneurs. And as investors, we we like the returns we get, but along the way, you learn things. And then you read other things. And you say, Oh, my gosh, I think I know some things that could be helpful to other people. But I’m not seeing it in some of the books and articles that are out there. And so we Alison, I took it upon ourselves to try and share what we’ve learned. And that was the first book build your fortune in the Fifth Era, which really explains why we think the world is, you know, going through unprecedented times and provides a lot of opportunity to entrepreneurs, and founders, as well as investors, that sort of why should you participate in early stage tech. And then this most recent book, the Intelligent Investor, it’s, you know, we, we thought that rather than write a book about what we’ve learned, we get 50 of the best VCs and angels to share their wisdom. And we put it all in one book. So you sort of get 50 books in one book. And I promise you, if you’re an entrepreneur, and if you’re planning to raise capital for many of those 50 people, the least you should do is read. Yeah, exactly. The least you should do is read because you’ll learn so much about them and what their personal, you know, preferences are and how they assess entrepreneurs and what it is they’re looking for entrepreneurs and and I think you’ll do a much better job of approaching them if you’ve if you’ve read the book

Jeremy Weisz

100 percent. What were some of the answers that stuck out to you People get some of the answers.