Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Why Facebook Will Be The Company To Succeed in Crypto, Why Founders Should Be Actively Angel Investing & Commonalities of Great Leadership From Mark Zuckerberg to Mark Pincus with Darian Shirazi, Founder & CEO @ Radius About this episode Darian Shirazi is the Founder & CEO @ Radius, the startup that provides you with not just data but truth allowing you to gain clarity to reach and convert your best B2B prospects. To date, Darian has raised over $105m in VC funding with Radius from some of the very best in the business including our friends at Founders Fund, 8VC, Salesforce Ventures and rockstars like Jared Leto and Charlie Songhurst. Prior to Radius, Darian has enjoyed roles such as first external engineering hire at Facebook and working on the "Sell Your Item" team at eBay. Darian has also made several angel investments in the likes of MessageMe, Sprig and Try.com just to name a few. In Today’s Episode You Will Learn: 1.) How Darian made his way into the world of tech as Facebook's first ever intern at the age of 17 and how that led to the founding of Radius? 2.) According to Joe Lonsdale @ 8VC, "Darian is one of the most respected founders and CEOs in the valley". How does Darian define great CEOship? What have been the commonalities he has seen in the great leaders he has engaged with from Mark @ Facebook to Mark Pincus? 3.) How did Darian approach the fundraising strategy for the $85m he has raised with Radius? How does Darian believe that founders can test quickly whether an investor is truly interested? Why is it so important to be fundraise as fast as possible? If an investor could only provide Darian one thing, what would it be and wh? 4.) How does Darian respond to investors that suggest founders should not be actively angel investing, as Darian is? What operational benefits does Darian gain from angel investing? How does Darian think about angel portfolio construction and specialisation? How has Darian seen investor attitudes alter when it comes to capital efficiency? 5.) As an early Bitcoin miner, how does Darian evaluate the world of crypto today? Why does Darian believe BTC has reached escape velocity compared to other currencies? Why was Darian skeptical on Ethereum for so long? What are Ethereum's ongoing challenges? Why does Facebook have the chance to dominate the world of crypto? Items Mentioned In Today’s Show: Darian’s Fave Book: Sapiens As always you can follow Harry, The Twenty Minute VC and Darian on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? This is the 20 Minute VC and Founders Friday with me, Harry Stebbings. You can submit questions for future guests on the show and be mentioned on the show with that by following us on Instagram at H Stebbings 1996 with two Bs. I would love to see you there. But to the show today, and a show which makes me wish I had spent more time on the West Coast, as I'd love to hang out with this guest more. We had so much fun doing the show, and so I'm very thrilled to welcome Darian Shirazi, founder and CEO at Radius, the startup that provides you with not just data but truth, allowing you to gain clarity to reach and convert your best B2B prospects. To date, Darian has raised over $105 million in VC funding with Radius from some of the very best in the business, including our friends at Founders Fund, 8VC, Salesforce Ventures,
0:42 Harry Stebbings? and rock stars like Jared Leto and Charlie Songhurst. And prior to Radius, Darian has enjoyed roles such as first external engineering hire at Facebook and working on the Sell Your Item team at eBay. Darian's also made several angel investments in the likes of Message Me, Sprig and Chy.com, just to name a few. And I do also want to say a big thank you to both Leo Aveda at Lob and Matt Garrett at Salesforce for the interest Darian stayed. We really do so appreciate that. But before we dive into the show today, our new sponsor Ring first made a splash when they were on Shark Tank a few years ago. The concept is genius. If someone rings your doorbell and you aren't home, or don't want to come to the door, you can respond to the person using just your smartphone, adding a level of both security and convenience. Today, over a million people are
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2:10 Harry Stebbings? Cooley. Cooley is a global law firm built around supporting startups and the venture capital firms that fund them. Now, we've spoken before about their forming the first venture fund in Silicon Valley and forming more VC funds than any other law firm in the world. But Cooley also represents more than 6,000 high-grade startups across the globe through the full company lifecycle. They're the number one law firm for VC-backed exits, both M&A and IPO, ranked by PitchBook. And since 2014, they've represented more companies in their IPOs than any other law firm. So to learn more about the number one most active law firm representing VCs and VC-backed companies, simply head over to Cooley.com or you can check them out at Cooleygo.com. But that's quite enough for me, so it's time to dive into this fantastic conversation with Darian Shirazi, founder and CEO at Radius.
3:00 Speaker 01 You have now arrived at your destination.
3:03 Harry Stebbings? Darian, it's such a pleasure to have you on the show today. As I just said, I heard so many great things, both from Matt Garrett at Salesforce, to Drew at A, to the team at Founders Fund. So thank you so much for joining me today, Darian.
3:14 Speaker 02 I appreciate it. I'm really excited for this too. I've been a fan of the show for a while and a lot of friends have been on it. Lior Avadar from Lob and Emily Choi from LinkedIn and now Coinbase, as well as Drew and the other investors that we have at Radius. So I'm very excited too.
3:28 Harry Stebbings? Well, I mean, I promised to pay you later for the kind words, but I want to start today with a little bit about you. And when you were a little boy, tell me, did you always dream of reinventing predictive marketing software? And how did Radius come about?
3:40 Speaker 02 No, that's a good question. I definitely enjoy big markets and I also love network effects. I've always been intrigued by the internet and the growth of the internet. And building things has really been my main sort of interest. And I remember when I was a kid, I'm an only child, so one of the unique things about that is you have to keep yourself busy because you just don't have any siblings. And I used to preoccupy myself with building large structures with Legos and also really just focusing always on building. I always wanted to build things. I had an obsession with building my own ski resort at one point. And as a kid, that was really my interest. And the best way to build something as you become older is to build a company. And that was actually Something that market Facebook had, we had in common is just that the best way to build something
4:25 Speaker 02 and really have an idea go from zero to something huge is to build a company. And I've been fortunate to be involved in a lot of different big markets and a lot of big companies. You know, Radius just happens to be the one that I spend 150% of my time on right now. But I'm sure that over the course of my life, I'll work on many, many more ideas that hopefully will be as big as the ones that I've been involved in.
4:46 Harry Stebbings? I mean, I can't wait to see them and I hope you let me angel invest in them first. But God, what a brilliant sourcing tool the show is, huh? But I do want to start, you mentioned market Facebook there. You were one of the first outside engineering hires. And a question from Drew was what were the biggest takeaways for you from that experience? And maybe how did you apply that to the time at Radius and the creation?
5:07 Speaker 02 Yeah, so that's a really good question. You know, when I got there, I really was not an amazing engineer yet. I sort of developed my skills. I was only 17 at the time. And really worked on a bunch of different projects. And all of us there were kind of junior engineers. We were all really young. We sort of had this belief that Facebook was a good idea and had the potential to be really big. MySpace was 80 million users. We were just shy of two, maybe actually less than 2 million at the time. And it was this belief that we were on to something big and that social networking would be a large space and that there would be a winner take all in the market. But you know, also at the time, I was so young that I didn't really have the awareness as to how hard startups are. And I just remember pulling many, many all-nighters, working on various projects.
5:51 Speaker 02 There was actually a video right before the IPO that CNN aired. And I happened to have a few second segment and it's me as like a teenager, basically barely able to stay awake because we were working so hard on a bunch of different projects at the time. And what I learned there was that startups are hard. They are just a constant struggle and there's always a new challenge and you have to embrace the challenges. Is that embracing challenges is really key is that they're going to be catastrophic events. There are going to be challenges that constantly pop up and you have to embrace ambiguity. You have to embrace the chaos. Another thing that I really learned from that experience was that Mark actually carved into the Wall in his apartment, fortune favors the bold, which is really, really an important phrase.
6:35 Speaker 02 It's from the Aeneid and it's a fantastic phrase because it means that taking risks usually pays off. And I think we spend too much time in the United States, training our people in the workforce to not take risks, not take smart risks and really are people sort of shy away from risk. And risk is what's allowed us to build new things. It's allows us to build new technologies. And if we have more people that are willing to take risks to build something great, we will have more progression in society. And so I'd say that that was my biggest takeaway is that really taking smart risks, working hard, understanding that startups are a constant struggle and embracing ambiguity that comes with the day to day operation. And that's really what I learned there. I would love to say that I learned a bunch of things on the technical side,
7:17 Speaker 02 which I did, but it was more important to see and have that experience. And that didn't really flip a switch in my mind until I had gone and started at my own companies or got involved at the Udemy guys really early when they were three people or, you know, worked on Radius from the beginning or saw Box when Aaron and Dylan were in a shack behind their uncle's house in Berkeley. These are all companies where I didn't realize until I had seen a few cases of these, transition from the early stages until to a really big company and what that really meant. And it all sort of clicked for me when I was about 25 and it's just been an amazing experience. And I carry every day that I worked at Facebook and other startups with me every day and use that to apply on how to make good decisions going forward.
8:01 Harry Stebbings? Now, this is a truly shit question, so please do forgive me ahead. You mentioned that kind of Aaron and Box, you mentioned the Udemy team, you mentioned Mark at Facebook. You've seen this cohort of incredible leaders. Are there commonalities amongst their leadership styles and their kind of company building characteristics that you think made them so great?
8:20 Speaker 02 There are, but I can tell you that those characteristics exist amongst entrepreneurs that have failed as well. So I can tell you that Adora Chung at Homejoy, who's now a partner at Y Combinator, she exhibited the same behaviors as the other successful entrepreneurs that I mentioned. And there are many others as well, you know, Gog and Biani, who recently shut down Sprig. But also founded you to me. And these are friends of mine. Actually, Goggan I knew from when I was fifteen years old. We debated against each other in high school. And the interesting thing amongst all these founders is that they really don't know how to give up. They don't know how to lose and they're competitive and they are emotionally attached to their mission.
9:00 Speaker 02 Those are things that are irreplaceable. It's something that Mike Moritz at Sequoia calls the code of the founder. And that really is true. And I think that one of those things is that as an angel investor or VC, is that if you bet on that personality type, you're going to be right more than you're wrong. But the key thing is that that is a unique personality type that most people don't have. And I remember making a bad decision not to advise or invest in Box or join Box because I just thought that the business was so young and so early and it was basically when it was just three people. And I also made a mistake on Waze too. And you know, I met the Waze team when they were coming out from Israel and I just never thought that anyone would use the app.
9:40 Speaker 02 But they were relentless and they were just never gave up. And that's something that I see in myself as well and I see in all these founders is that that relentlessness and the emotional connection to the mission is irreplaceable. And I think that it's super, super important to look for that as an investor. Look for that when you're going for a job, trying to find someone to join or a company to join is that that's the most important attribute about the founding team. And that those founders will be successful at one point or another in their lives, even if the thing that they're working on at the time is not the be all end all.
10:12 Harry Stebbings? No, absolutely. It resonates when you look at Lior and his commitment to learning and mastering chess for six months.
10:18 Speaker 02 Oh, exactly. Yeah. He and I have been playing chess a bunch recently. It's pretty fun.
10:24 Harry Stebbings? But I'm intrigued because you said there about the code of the founder and never giving up. As an investor, a question for me always is, how do you balance between that vision, that idealism of what you believe you can create will be the future, with also realism of maybe when something's not working out? How do you balance between the two?
10:41 Speaker 02 It's really difficult. That's something I don't know how to answer. I can tell you that it has a lot to do with market dynamics and for founders to be able To read those market dynamics and you know markets change very, very rapidly. I think we've seen a bunch of companies that are going through big challenges in the startup community today even is that they raised on large valuations and they're in the process of restructuring their business, whether it's Zenefits and that entire space, or whether it's, you know, software as a service in certain sectors, companies like Clearslide, et cetera, that really had high lying valuations that are now in the process of having to read the market and switch their operating model, be more diligent about how they think about the business and running the business and getting to the next phase.
11:25 Speaker 02 So I really do believe that founders have to be able to read the market and that's hard to do. Sometimes you can't do it. Sometimes you can't be perfect at it because markets change so rapidly and they've especially changed with how the startup community has focused more on these huge rounds of funding at high valuations that ultimately need to be able to go public. And as we saw today with Dropbox, the IPO priced below the last round valuation. So these kinds of dynamics make it really hard for founders to succeed and they have to be good at the macro and the micro at the same time.
11:55 Harry Stebbings? Again, it brings me back to Lior and a core element for him was that sustainable growth mindset. I'm intrigued, how do you think about that kind of sustainable growth mindset in these very frothy times and also kind of capital efficiency and how core it's been to you building Radius or not actually in terms of growth prioritization?
12:13 Speaker 02 So we definitely have had to take a hard look at that in the past few quarters is that how do we get more capital efficient and it's super important because now investors and the market are asking for capital efficiency with SaaS businesses. 18 months ago, that didn't really matter, but if you look at things like Okta, you know, you look at companies like Nutanix, et cetera, these IPOs, investors are expecting operational efficiency out of these SaaS businesses, sales forces pushed towards profitability, even in the larger SaaS companies, that's been the case. And so sustainable growth mindset from the early stages is one way to cut it. I think it really depends on your business, right? Like if your business is one that is a brand new product that is in a new category and you need to
12:55 Speaker 02 create a new category, which is Radius, for example, because we're creating the category. Of data intelligence and hopefully Gartner will be releasing their report within the next couple of months. But building a category is very expensive, requires a lot of marketing, requires you to really spend money to build and create that category. But businesses like Lob that are in established categories that are new innovative technologies. I sort of think about Lob the same way I think about Twilio innovating in the SMS space versus the direct mail space. Or in the transactional mail space, those are businesses that can afford to do sort of sustainable growth over time. And I will say that it really depends on your business to determine when the right time is to either start with sustainable growth.
13:37 Speaker 02 Or to start building that category and take the risk to really shape a new market.
13:41 Harry Stebbings? We mentioned the element of the big funding rounds there. I'm very interested because you raised over eighty five million dollars according to the trustee crunch base. I'm intrigued though, what was the fundraise strategy? Why did you select the investors you did? And let's start with that.
13:54 Speaker 02 Yeah, so I think that one of the things was we wanted to build a new market. We wanted to build a new market, the founders and I wanted to. We believed that this was the way to drive data and intelligence to CRM. It was going to be a new sort of wave for CRM. And if you think about, actually I wrote an article about this five or six years ago now, which is this future of CRM will automatically recommend opportunities to you. And it was published in Forbes and got ton of traffic to the article. And that was really the basis for our vision, which is can we make CRM smart with data and intelligence? And it's something that Benny Off at Salesforce has been doing for a long time. And that was a new market category. We also wanted to get our customers to provide us their data in order to build a better data set for all customers that leverage our platform.
14:39 Speaker 02 And that network effect was something that we also wanted to do. These were very, very new innovative ideas, someone had never done this before. And so we wanted to find a series of investors that were willing to take that risk and really understood. Okay, we want to put money into this company so they can really build out the market and also shape the market and lead the market. And those are investors that are not ones that look for that sustainable growth really early on. They look for can they lead the market and can they start to get great customers? And we've really Done that, you know, we've got customers like Allstate and MetLife and Amex and First Data and Comcast. We have these large logos that pay us a ton of money that really have validated that we're leading the market.
15:21 Speaker 02 And the investors that we picked, whether it's, you know, Joan Drew at ABC or whether it's Founders Fund. These are the investors that take risks on these new big markets because they have a vision for where these markets are gonna go. There are a lot of other venture capitalists that don't necessarily want to have a vision. They want to view every market opportunity and every business opportunity as something they can read from day one on a spreadsheet. And that's just a very, very different type of investor and one that is not necessarily gonna find the next Facebook or the next category defining company. So I think that's why we picked those investors.
15:53 Harry Stebbings? You mentioned kind of different types of investors there. I'm interested for you as a founder and say for me as an investor. Help me improve. If an investor could only provide one thing other than the capital itself, what would it be, do you think? Is it empathy, as is often stated by entrepreneurs?
16:09 Speaker 02 Yeah, I mean empathy is important. Being a founder is really tough. It has great days and terrible days. I think also network is very important, especially in our business. Our business is driven by large enterprise customers. And, you know, for example, the ABC team introduced us to Comcast and that's our largest customer. So it gives you a sense of the network is very, very important. As we continue to grow, we want more investors that can bring that network.
16:33 Harry Stebbings? Awesome. No, I love that. If you were to kind of self-analyze though on the raise itself and with benefit of hindsight, what do you think you did really well in the raises? And is there elements that you'd improve upon for the next businesses that you actually cited earlier?
16:46 Speaker 02 Yeah, and you know, it's driving urgency is really important. For the sake of your business, raising money quickly is very important. And the longer it drags out, the more that it's distracting and distractions are really the enemy of the founder. Because as things get more complex and as the business gets larger, you'll spend more time on these distractions, which are fundraising or team retention or things like that, rather than actually focusing on the business itself. And so if you can minimize those distractions by accelerating your fundraise, that's very key. And what I mean by that is getting to know quickly, getting to know. Quickly from investors that are not interested and being able to read whether investors are interested early on and creating a sense of urgency for you and for them.
17:28 Speaker 02 Investors don't like to say no because they don't like closing the door on potentially good opportunities. So really hard to know whether you're in the no camp or the yes camp because you'll always kind of get a maybe unless you push for a no. And we found that we got a ton of people to say no in our early days, but there were a number of top tier investors as well that said yes. And it was because we created that urgency early on.
17:50 Harry Stebbings? Can I ask, how do you drive to that outcome? Is it quite simply by saying, Darian, are you in or out? Is it by consistently following up? How do you drive to that urgency of outcome?
17:59 Speaker 02 Yeah, well, it was funny. I asked Mark Pankas about this when he was raising money for Zynga early on. I don't know if he remembers this, but I certainly do. And he basically used a line with one of the investors he was trying to court or get into the company. And he said, like, if you want to do it, just do it. And it was over dinner. And that sort of drawing a line in the sand and saying it that way really worked because it really drove an outcome. And that's the case with any deal is that you want to drive an outcome quickly because the longer it takes, the more people sort of want to back away. Or they lose interest, or they feel as though you're losing interest. It's just frankly a waste of time. The sooner that you can get to an answer is really key. And I think a lot of founders that I see, some that I've funded, they're so worried about getting a no.
18:43 Speaker 02 When getting a no is actually better because then you can just move on.
18:46 Harry Stebbings? No, I absolutely agree. Fundraising for a fund, I completely know what you mean. But I do want to finish today on a topic that seems slightly controversial actually amongst the VC community that I speak to. And it's you're a founder and you're also an angel. I'm intrigued. Many VCs suggest that this is wrong as you're maybe not as committed as someone who doesn't angel invest. Tell me, why are these investors wrong, do you think?
19:08 Speaker 02 It doesn't take that much time to manage these investments or to evaluate investments. And most of the investments that I'll do are from network introductions and I'll maybe take one meeting and then make a decision pretty quickly. It keeps your mind fresh. I think that having perspective is very important as a founder. And I think also that it just doesn't take that much time to evaluate some of these investments. I get three to four inquiries a week from people that are either following up or that are new or that are from some other part of the world that want me to take a look at an investment. I I don't even really read those. The ones that I really look at are evaluated by my personal friend network that I trust. And that really doesn't take any time because if those individuals are in, I probably will invest as well.
19:51 Speaker 02 So that's really how I sort of think about it. And that's what's not really cost me a lot of time on this. If I did take more time on it, I don't know if I would necessarily be able to do everything else. And I think that as long as it is from your network and as long as it's a very minimal amount of time, it ends up being not that distracting at all. So I would disagree with that. I think that there are a lot of top tier investors that encourage their founders to do this. I mean, Sequoia has their scout program, which I think is pretty popular. So I would say that it's it's definitely good to give founders perspective. You also never know when might learn something from another founder. You might learn something from an investment that you've made that may help your business as well.
20:29 Harry Stebbings? No, absolutely. I I couldn't agree more in terms of that cross functional learning, so to speak. I am intrigued, though, when you decided to open up the bowels of the checkbook, so to speak. Was there a strategy in place? Was there a thought on portfolio construction? How did you think about kind of check size consistency? What was your thoughts on maybe investing mechanics?
20:47 Speaker 02 Yeah, so it's pretty simple for me. It's really, are there other investors that I trust that have evaluated this that are in my friend network? And then second is, do I believe that this business can raise additional capital? And is it in a massive market? Those are the three first qualifiers. And then the fourth one is really, does the founder exhibit the qualities I talked about earlier in the interview? And those are pretty quick to suss out. So, you know, you can eliminate deals pretty quickly if they aren't from your network or you don't know anyone else that's that you trust that's going to invest in the business. The second, you can eliminate pretty quickly as well. And and same with the third. So, you know, that's sort of what I look for, and that's led me to a lot of really great deals, you know, that have been great companies and also met great founders, you know.
21:30 Speaker 02 And you also see a lot of founders leave companies that have been really successful and go start other products or companies. So one of those, for example, is a Udemy founder. One went to go found Sprig, that ended up being, it seemed a good opportunity initially, but then sort of didn't after the Uber Eats competition that came about. And then the second was Carbon Health, which is, you know, started by the last CEO of Udemy, which is reinventing how, you know, primary care visits. And that seems to be, you know, doing very well. So you see this sort of network build of founders that you trust and technologies you trust. And that leads you to other businesses, like the founder of Sprig, before he started Sprig, he worked with Lyft. And so then that got me interested in Lyft. And so these are really the, the ways in which I sort of think about angel investing.
22:15 Speaker 02 I don't have a specific portfolio strategy because I frankly think that that leads to trend chasing, which is very, very challenging. And I think trend chasing and angel investing is tough. It's not so tough if you're writing larger checks. If you're writing larger checks and you have something that is already in a developed market and it's showing growth, writing a larger check in themes, it makes sense. But as an angel, you're really looking for the next Pinterest or you're looking for the next big play that's going to be in a market that no one's really talking about yet.
22:44 Harry Stebbings? Yeah, no, trend chasing, I think timing is an enemy of most investing. So I couldn't agree with you more there.
22:49 Speaker 02 On the early stage side, for sure. But you know, there's also been a lot of things that, one theme I'd say across all investments has really been network effects. And that's because I saw the power of that at Facebook. My best friend from high school and I were mining Bitcoin in 2011. So it's just like, we've seen network effects and how those can shape the market and how those can grow really fast. And so that's really a theme that we latch on to as well.
23:12 Harry Stebbings? You mentioned Bitcoin there, not me, but so did Drew in our, so did Drew in our call before this interview. And he said, you've got to find out Darian's perspective on the current state of crypto. So before we go into a quick fire, I'm just going to drop the mic on that and go, current state of crypto, hit me, Darian.
23:30 Speaker 02 Yeah, so I do believe in the long-term thesis of crypto. I am what most people call a Bitcoin maximalist. So I think that Bitcoin, because it has such strong network effects already, it's definitely on pace to be the leader. I do believe also that the challenges in the world today make Bitcoin really interesting. If you are a middle-class individual in China or Russia and you want to get your money out, it's a perfect way to do it rather than carrying gold bars over the border. And I think that that right there is of strong, strong value. I think Ethereum is super interesting. I actually didn't believe in it when some of my early Cal classmates were getting involved in it. And I thought it was kind of a joke. And then sort of I saw it pick up and the value of the technology.
24:14 Speaker 02 And I still believe that it is very interesting, but it has a lot of founder risk right now. One of the reasons I think Bitcoin is here to stay is because it has no founder risk and likely the founder passed away quite a while ago. So I'm the Bitcoin maximalist, definitely believe in Ethereum. I also think that ICOs are super interesting. They're going to get regulated, but it's a great way to raise capital. And we need to have better methods by which to regulate them such that people can raise capital. I also think that there needs to be more work done around these white papers and what they mean. And investors need to have more disclaimers around it. But I think it's a fantastic way for these new ideas to raise money. Now, I will say also that on crypto, I think that there's a high probability
24:56 Speaker 02 that the company that will really succeed in crypto will be Facebook. And the reason is that for them to launch their own coin and for them to distribute that coin and allow developers to build on top of it would instantly be the largest ICO and instantly be the largest cryptocurrency. The ability to move money from user to user on Facebook through a crypto proxy is just going to be, I think, the way that this space goes. And so that is really going to be the only competitor to Bitcoin. But right now, I'm definitely long Bitcoin. And it's been a fantastic way to learn about new technologies and also to take advantage of growth in the market.
25:32 Harry Stebbings? No, I love that thesis on Facebook and I haven't actually heard it before, so love it. But I do want to dive into a quickfire and move away from crypto. Hours on it. So we're gonna do a quick fire, sixty seconds per statement. How does that sound, Darren?
25:45 Speaker 02 Sounds good.
25:46 Harry Stebbings? So hit me, your favourite book and why? What must I be reading on the next West Coast flight?
25:50 Speaker 02 Sapiens, I think you should definitely be reading. It's a fantastic book. It's about how humans and Homo sapiens are so geared to rally around themes, rally around species, and how Neanderthals didn't do that. The evolution of the human and how that has like played into the modern economy and how we think and how we all work together. It's a fantastic book to really understand humankind and our evolution. So really, really love Sapiens.
26:15 Harry Stebbings? What motto or quote do you frequently revert back to, Darren?
26:18 Speaker 02 Fortune favours the bold. That's the one I think I brought up earlier in the interview. It definitely is my favourite.
26:23 Harry Stebbings? Is there a time where you've been burnt because of it?
26:26 Speaker 02 Oh, totally. Many times. And I think that that's where you learn, is that you learn quickly by making those mistakes. And that's part of life, is that life is about a series of challenges and learning from those challenges and going after those challenges head on as well.
26:39 Harry Stebbings? No, absolutely. Speaking about kind of life challenges and life lessons, tell me about a moment in your life that served maybe as an inflection point and changed the way you think?
26:48 Speaker 02 This may seem a little silly, but in 2009, we were working on a startup and our office flooded. And it was a very stressful time. Everybody in the office didn't know what to do. It was just, there was a lot of stress around a few things that happened on that day. And I remember that I didn't have a place to sleep because our office was actually also our apartment. And so the whole apartment had flooded and got in my car and I wasn't really thinking about anything. I was just thinking about gotta make the company successful, gotta make the startup work, all these other things. And I was in the car to go stay at my parents' house in Palo Alto and I was driving on 280. And I hit a deer, a 400 pound deer in the left-hand lane of 280, at about 85 miles an hour. And
27:32 Speaker 02 it was devastating. It was devastating for me and sort of saw my life flash before my eyes. It was right near Woodside. And I think that had I not swerved in the right way and sort of clipped the deer the way that I did, I probably would have died. And that inflection point made me realise that there are random events that happen. There are things that you can't control, but you know, you should always be mindful of your life, how short it is. You should be mindful of what you work on and what you really care about. And sort of I saw that I really care about commitment. I care about loyalty. I care about doing what's right. I also care about building great things and doing the best that I can in every situation.
28:11 Speaker 02 But that really served as an inflection point for me and I remember it. I know that it may seem silly, but for me it was a, it was a very big day and I was very saddened that I, that I killed that deer. So, yeah.
28:22 Harry Stebbings? I mean, that's one bad day, Darren. Fuck, that is horrible.
28:27 Speaker 02 Yeah, it was a bad day. It was a bad.
28:29 Harry Stebbings? I mean, I'm hugging you through Skype right now, but I do, I do wanna do a penultimate question. What's the biggest advice to a graduate coming into the workforce today? You started very early, like me. What would your advice be?
28:41 Speaker 02 Yeah, my advice would definitely be take risks and fail early. Those are really things you're gonna hear from everybody. But also I think, don't go take a desk job that is the easy way out. You know, I saw so many people at Cal. It was one of the reasons I dropped out of Cal was because I saw so many people that were just content with getting that desk job. I think everyone in the world has a responsibility to make the world better. And the only way we do that is if we build and progress. And if everyone just sort of takes, takes the easy way and just goes and gets a desk job somewhere, we'll never improve. We'll improve at a slower pace. And so it's super important that people think about that. Think about how they can make the world better, no matter how it is.
29:22 Speaker 02 And we're starting to see the workforce really change with automation. And if people don't do this, if people don't think progressively in how they can improve the economy, improve the world, improve social society, take risks, things like that, then they're gonna be automated out of a job as well. And so I think that's really the advice I have, whether it's getting involved in your local community, whether it is starting a company, whether it is building something that you believe will improve the world, whether it's getting into research to prevent cancer or extend human life. Those are all things that are really interesting. Those are things that you can look back on at the end of your life and say, I tried to make the world better and that was my responsibility in conjunction with all the other things that I did. And that's, I think, what I, what I would advise graduates on.
30:04 Harry Stebbings? You spoke about building there. Final question, the next five years for you and for Radius, what's that roadmap ahead?
30:11 Speaker 02 You know, I don't know yet. We're obviously building a great company. We're adding great customers. I think that there will be a lot of new markets that emerge over the next couple of years that I will be interested in and curious about. So I can't say definitively what the plan is for me, but I can say that I'm deeply engaged in Radius. I believe in the thesis, I believe in the business and the company is on a good path. It's just a question of how fast we can grow it and that's really, really what we think about today. But for me, there's going to be a lot of things I dabble in because just have a wandering mind. So, yeah.
30:42 Harry Stebbings? Well, I cannot wait to see the growth and I look very forward to Mojitos with you next time I'm in San Francisco. So thank you so much for joining me today.
30:49 Speaker 02 Thank you so much. I appreciate it.
30:53 Harry Stebbings? What did I tell you? Such a fun episode. And if you'd like to see more from Darian, which I highly recommend, then you can find him on Twitter at Darian314. Likewise, we'd love to see you here behind the scenes at the 20 Minute VC. You can do that on Instagram at H Stebbings 1996. It'd be great to see you there. But before we leave you today, our new sponsor Ring first made a splash when they were on Shark Tank a few years ago. The concept genius. If someone rings your doorbell and you aren't home or don't want to come to the door, you can respond to the person using just your smartphone, adding a level of both security and convenience. Today, over a million people are using the Ring Video Doorbell to help protect their homes. And now Ring has a great new product called Ring Floodlight Cam.
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Previous 20VC: Greylock's Jerry Chen on The 2 Fundamentals To Assessing Startup Risk, Why Good Investors Have To Be Optimistic & Why VCs Get In Trouble When They Move Outside Their "Strike Zone" Next 20VC: Why You Have To Raise $100m+ If You Want To Go Big Today, The 5 Fundamentals To Starting and Scaling A Successful Marketplace & Why Female Founders Under-Promise and Over-Deliver with Paul Hsiao, Founding Partner @ Canvas Ventures Page updated September 29, 2026 · transcript and summary are machine-generated