The Secrets of Venture Capital With Peter Livingston of Unpopular Ventures

Peter Livingston

Investor, entrepreneur, and mentor, Peter Livingston has made a name for himself as an expert in startups and establishing brands. He is the Founder and General Partner at Unpopular Ventures, an investment group that sows into early-stage tech companies before they take off. He has also worked individually as an angel investor for more than seven years, working with more than 300 startups.

Peter’s background is in technical and mechanical engineering, getting his start at iRhythm Technologies, Inc. He went on to start his own company, Lifesquare, and as a Consultant at GE.

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

  • The idea behind Unpopular Ventures
  • Knowing when to invest in smaller tech companies
  • Early investments and why they can be so powerful
  • The key aspects that ensure the early success of startups
  • How much you should invest and fees you should be aware of 
  • Creating the right incentives for investments
  • The importance of investing in multiple deals
  • Some valuable resources to get started in venture capital

In this episode…

Venture Capital has exploded recently with the acceleration and popularization of startups. It’s a great opportunity for investors and entrepreneurs to earn money and be a part of something new. However, there are a lot of dangers from the investment side. Picking the right companies is particularly hard when investing into businesses during their early phases. On the other hand, the reward is high for those who can pull it off.

Peter Livingston has spent much of his career in venture capital and has discovered firsthand how to recognize a promising startup. His investment group, Unpopular Ventures, has worked with more than 160 businesses to great success. If you want to know how to get started in venture capital, listen in.

David Melamed interviews Peter Livingston, the Founder and General Partner of Unpopular Ventures, to find out how to invest in venture capital the right way. They talk about the promising features of a budding startup and how to identify them early on. They also get into Peter’s personal experiences in venture capital and some of the success stories along the way. Check out this episode of the Fixing Incentives Podcast to hear about all this and more!

Resources mentioned in this episode:

Sponsor for this episode…

This episode is brought to you by Tenfold Traffic.

The only projects I take on currently are performance-based relationships.

What that means is…

All marketing would go through me on my own dime, and we negotiate a revenue share.

I don’t want someone to give me money if I don’t generate a return for them.

But, if I am making someone a ton of money, then I want to share in the revenue.

In other words, I want to participate in the full value I am creating.

Right now, I am only looking for one or two companies a year to pour my heart and soul into and to have as partners.

An ideal partner is someone who has a converting funnel and can handle scale and let me work my magic.

If you are a company that knows your lifetime value of a client and wants to spend as much as you can to acquire a customer and dominate the market, then I am your person.

If you are looking for a partner, I am your person, and if you are looking for a vendor, then there are several people I have vetted and can refer you to.

Visit to learn more or email me at david at tenfoldtraffic dot com.

Episode Transcript

Intro 0:03

Welcome to the Fixing Incentives Podcast where we talk about the incentives that drive success. Now, let’s get started with the show.

David Melamed 0:14

David Melamed here, I’m the host of Fixing Incentives Podcast, where I talk with top business leaders about their journey and the behavior that powered their growth. I have today with me, a really amazing guest. And I’m really looking forward to it. And we’ll get right into that in a minute. But first, here’s just a brief message from our sponsor. This episode is brought to you by Tenfold Traffic. Now, the only projects I take on are performance based relationships, what that means is all marketing goes through me on my own dime, and we negotiate some sort of revenue share, I don’t want to, I don’t want someone giving me money if I don’t generate a return for them. But when I make a ton of money, I want to share in the revenue. And that’s one of the reasons actually why I started angel investing and why I’m doing this, this series with with syndicate leads from AngelList, and other venture capitalists, because I was looking for, you know, if I invest in the company, and then I get involved in some way, with advising or with marketing, I would have the ability to, to really realize the full value I create across that business. So that’s why I got started originally, but since then, I realized, I’m probably not gonna get involved with marketing with any of these portfolio companies. But it’s, you know, that’s what led me there. And it’s been an amazing learning experience. And I’m really excited to jump in. But if you are a company that has a converting funnel knows the lifetime value of a client, and you’re really in a place to start, you know, pouring fuel on the flames of your of your customer acquisition, definitely reach out, you can visit my website, David Melamed dot com. Or email me at David at Tenfold Traffic dot com. First, the guests that I have was introduced to me by Jack Coleman from Fourth Realm, VC, which is I’ve done some early stage deals with them some secondary investments with them. And they said that I asked who else in the, I guess angel investing world is a great guest. And they said that, by far, the number one person who’s tried to get on the show is Peter Livingston. So I’m really excited to have Peter Livingston here with he’s a longtime angel investor and General Partner and Founder of Unpopular Ventures. And they’re looking for the best companies off the beaten path. And I just, just to kick it off, I love that off the beaten path idea. Um, I suspect there’s a lot of founders that self exclude from raising money, because they’re convinced they don’t have the relationships, they don’t have the access. I know when you know, when I read up about startups and raising capital, one of the most common pieces of advice I see is get introduced to to their investors, through someone you know, someone that knows you and there’s I’m not just talking about someone who’s like, underserved, underprivileged coming from, you know, a third world country or underdeveloped, you know, area I’m talking about, you could just have a regular person in the neighborhood who, you know, has a great product and idea. And, you know, they’re starting to get traction and making progress. And they can really, really scale if they have the right strategic investors and partners. So I first I’d love to know, Peter, tell me a little bit about how you came up with this idea of Unpopular Ventures how you develop what’s called the courage to seek out the the opportunities that maybe you know, the sequoias of the world are, are not even giving the time of day?

Peter Livingston 4:09

Yeah, well, to start off with David, thank you so much for having me. And it’s my pleasure to be here. And thank you also, for the incredibly kind words, I’ll have to get the name again after we’re done. It’s a who referred you to me to send him a thank you note. Because I guess that’s an incredibly nice. I’m trying a little red. But, but thank you so much for the kind words and to answer your question. So Unpopular Ventures, and yeah, we try to focus on finding really great companies speculate great founders that are a little bit off the beaten path or a little bit uncomfortable for other people. And where that comes from is that one in all my reading and studying of successful startup history, almost all of the super mega successful companies were popular in the beginning. And then also in my own experience. I have a huge like, when I was first starting out, or even before I started angel investing. And then even when I started angel investing, I miss some wildly successful companies that I thought were just terrible ideas. And so I’ve been exposed multiple times to be Super Breakout mega successful things. And I distinctly remember looking at them at the beginning and thinking, That’s stupid, it’s not gonna work. And yet, those were the ones that were mega successful. And I could go through some of the stories. So one was a fraternity brother of mine founded Instagram. His name’s Kevin Systrom. And he didn’t directly approached me for funding. But I remember hearing that he was starting it, I remember hearing this trying to raise a little bit of money from some friends. And I could have easily reached out to him. But I downloaded this app, which is called bourbon at the time, played around with it, I was like, I don’t get it, it’s kind of stupid. And gosh, only I had invested and he pivoted a few months later, Instagram, exited for a billion dollars later, and I would have made a ton of money. And so that was one another was the DoorDash founders are very good friends of mine, business school, and even venture capital club co presidents with them. So I did very well. One of them has told me they were starting something food delivery. And I really thought, food delivery, low margin business, not that sexy and not like, again, they didn’t necessarily push me for funding, but I knew they were doing it, I was actively looking for investments at the time, I could have easily just been like, Hey, can I print a little bit of money, and I didn’t, because it seems like a bad idea to me at the time. And those and other learnings led me to realize that some of the biggest and most successful things out there start out looking like that ideas are a little bit uncomfortable to most people beginning. But the thing that ties them all together. So usually started by pretty smart people. And they’re very ambitious. And I think that is this dangerous combination of like, doing something that’s off the beaten path. Seems like a bad idea, but really talented people that are chasing them. And so forever after now, they’re smart people go and do some doing some it seems weird or unpopular. AIPAC. I run towards that I’m trying to not make that mistake.

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About David Melamed

David Melamed is the Founder of Tenfold Traffic, a search and content marketing agency with over $50,000,000 of paid search experience and battle tested results in content development, premium content promotion and distribution, Link Profile Analysis, Multinational/Multilingual PPC and SEO, and Direct Response Copywriting.

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