144: Why Generosity is a Strategic Advantage: Interview with Ryan Delk

Most of our email inboxes are out of control. Besides the junk there are people asking for help, advice, or an introduction. In the moment, it feels easier to delete it and move on. Turns out, we are missing out on a strategic opportunity.

144: Why Generosity is a Strategic Advantage: Interview with Ryan Delk

Rather than skip over these requests, this week’s guest on The Portfolio Life embraces the opportunity to help. The trick is he only invests 5 minutes or less, but the return pays long-term dividends.

After working at big name start ups like Square and Gumroad, Ryan Delk knows a thing or two about the power of influence, and the value of a strong network. It seems like he always knows somebody who can help you with your problem, and he’s done that with intention.

Listen in as Ryan and I talk about starting his entrepreneurial journey in college, interning in Kenya, and how not to ask for an introduction (or make one).

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Show highlights

In this episode, Ryan and I discuss:

  • How to create value for people and get them to pay you for it
  • Leaving college to join Gumroad
  • How to connect with interesting people and build authentic relationships
  • Why trying to optimize every interaction is counterproductive
  • Knowing when a new venture is a good bet or a foolish one
  • Why basic transportation is just the beginning for Uber


  • What you’re valued for and what you’re respected for is directly proportional to the value that you bring.
  • Be outlandishly generous without fearing you’ll be taken advantage of.
  • An element of humanity won’t diminish your success.
  • It is more strategic and enjoyable to be helpful vs trying to optimize every interaction for what you can get out of it.
  • Take immediate action when you know that you can help someone.

Give before you try to get.

Jeff Goins

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How are you practicing generosity with people you meet? Who is your favorite person to recommend to others? Share in the comments.

Click here to download a free PDF of the complete interview transcript or scroll down to read it below.


I just found that sort of defaulting to trying to always be helpful is a pretty good default to live with in your life, and you end up through that connecting a lot of interesting people, connecting with a lot of interesting people, and being able to build authentic relationships with people. I think if you’re playing the long game, that is a much more strategic and even enjoyable way to live life than just trying to optimize every interaction for what you can get out of it, or what your company can get out of it. –Ryan Delk


[0:00:38.7] JG: Welcome to the Portfolio Life. I’m Jeff Goins. This is a show where we do lots of different things, lots of fun things, but most of what we do is try to answer a single question. That question is this: What does it take to live a creative life?

The answer to that is it takes lots of different things. A creative person is not just one thing, not just a writer, or a painter, or a musician; they are many things. In fact, one person can be all of those things. On this show, and especially on this episode, we talk about how very different career paths can intersect in some really interesting ways.

What happens when, I think, we embrace this portfolio mindset is the work that we do becomes better, the lives that we live become richer and more meaningful, and the message that we share with the world becomes a lot more interesting. Because the truth is the way we live our lives is not monolithically, it’s not just one thing, but our lives are messy and integrated in some really beautiful ways.

My guest today, Ryan Delk, who has worked for a number of tech startups based in San Francisco, has a fascinating story about how he went from fixing his friend’s iPhones in college, to taking an unexpected trip to Africa, to eventually quitting college and moving to San Francisco to work for Square, and then Gumroad, and all kinds of other interesting adventures to follow.

If you have ever wondered if the thing that I’m doing right now, what does it matter? How is this preparing me for the next thing? I want you to listen into this episode, because I think you’re going to find some great nuggets and some great takeaways.

Without further ado, here’s my talk with Ryan.


[0:02:28.8] JG: Well, Ryan, welcome.

[0:02:30.0] RD: Thanks Jeff, I’m excited to be here.

[0:02:32.8] JG: I bet you are, I bet you are. We have a fun way that we’ve connected, I think. I can’t even remember how we first got connected, but I have to give credit to our mutual contact Paul Martin, who I think connected the dots for me, because at some point, you and I were talking when you’re working at Gumroad.

Then I connected that you knew Paul, and there’s this whole other past of yours that I wasn’t aware of. Am I remembering that correctly?

[0:03:04.4] RD: Yeah, I think we met up to talk about Gumroad stuff, and then sort of connected the dots around Paul and several other mutual friends that we had. I think that we didn’t even realize, maybe we had a loose sense of it, but didn’t really realize how many layers there were until we got together.

[0:03:21.3] JG: Yeah. It’s fun when that happens. You inspire me, have such an interesting story, and I wonder if we could spend a little bit of time telling it and you can correct me when I mistake the details. Your story, for me, begins when you were in college and you had a business refurbishing broken iPhones. Tell me a little bit about that?

[0:03:45.9] RD: Yeah, it’s a funny story. I went to college at the University of Florida in Gainesville, and sort of quickly realized — this was before AppleCare, and the Apple repair process was really lightweight, and sort of cheaper and easy, and there was no Apple store in Gainesville. The nearest one was like two hours away, and at that point, cracking your iPhone screen or your iPod touch screen was, you know, sort of like this horrible thing because it was really difficult to get replaced. It was hundreds of dollars.

What people would do is they would basically just sell their iPhone at that point, or sell their iPod Touch and just get a new one. Most people didn’t know that it was actually really easy to — especially in the older models. It’s actually way harder now, but it was really easy to replace the screens, so I found an electrical engineer friend that knew how to do it.

We would just bulk buy a bunch of iPod Touch and iPhone screens online. He’d buy a busted iPhone for 100 bucks, replace the screen, and resell it for $300 or $400. The screens cost you three or four bucks a piece. Pretty good margin, it took about 10 minutes to do it. It was a fun little — sort of limited volume — but fun little side project for a while.

[0:04:57.4] JG: Yeah. I have noticed for a while there is a significant difference between where I was at your age and you are at your age. When I was in college, I wasn’t thinking about how to start a business, and so I was just curious, what made you even think of this opportunity?

[0:05:17.0] RD: Yeah, I think. I mean, since I was in middle school, maybe even elementary school, I remember just sort of like thinking through this idea of how do you create value for people, and then get people to pay you for that value? Then, I think my thoughts later in high school evolved into this idea of what are things that people don’t value that you can add value to, and then sort of like, sell it for much more than whatever that value creation cost you?

iPhones were sort of like one permutation of that, but I did it a lot with event tickets. Like, football tickets, stuff like that. Just anytime that I felt like there was like sort of an opportunity in the market. I sort of just became fascinated with any place there was to create value in a lightweight way, particularly ones that didn’t take a lot of time. Then, you know, be able to use either just sort of pure hustle, or smart marketing tactics, or whatever to actually turn it into something where you can make money.

[0:06:11.4] JG: Okay, I’m looking at your Twitter page and, you know, you’ve got this long list. I think it’s a long list, iHub, Square, Gumroad, and now your current job working at Omni is kind of a fun new startup that we can talk about. I was also looking at Beomni.com, and you have this little popup that says “how can I help you?” So I’m talking to Madison right now, and I told her, tell Ryan Delk I love him.

[0:06:39.9] RD: Nice. That’s hilarious.

[0:06:43.0] JG: I’m using up good startup resources right now. She said, “Hi there, I’d be happy to pass along the message. Can I tell him who this kind note is from?”

[0:06:50.5] RD: Amazing.

[0:06:53.3] JG: I’m just going to do that right now. Okay, long list of pretty cool opportunities. How did you get from refurbishing iPhones in college to moving to San Francisco and working in tech?

[0:07:04.7] RD: Yeah. It was a super around about way that, in retrospect, sort of makes sense, but certainly I couldn’t see how these dots were going to connect in the moment. I went to, the University of Florida. I did my freshman year internship in banking. I thought I wanted to do Wall Street and do sort of that whole career trajectory.

Realized quickly that wasn’t for me, and so the next semester, I was looking for what would be the craziest thing I could do next summer, and I had read about this guy in the New York Times who actually went to a church that I went to growing up. We had some mutual friends, and I met him a couple of times, and he had a co-working space. sort of like Tech Hub, in Nairobi called iHub.

I reached out to him and just said, “Hey, you know I’m pretty good at sort of starting businesses and I think I know how to think about these things pretty well. Could I come out for the summer and just basically be your right-hand man?” My pitch was basically, you know, “You have all these — you have about 1,500 engineers and designers for building businesses in Nairobi, tech companies, and I can help them, I think, understand marketing, and scale, and potentially how to raise money, and things like that.”

I ended up doing that, and it was actually through that process that I became sort of really excited about, I would say like, the broad startup world, and this idea of being able to sort of start a company from nothing. Leverage technology and punch way above your weight class, both personally and as a company.

When I was there, there’s a bunch of awesome people from San Francisco that came over to visit, and one of them was Marissa Mayer, who is a PM that sort of led all the PM’s at Google at the time. Now she’s the CEO of Yahoo. She was talking about this company that she just invested in called Square.

At the time, it was a small company, and she said that they’re doing some really interesting things, and if you want to come back to San Francisco you should talk to them for sure. I don’t remember exactly how it all happened form there, but I got looped in with them, and I basically pitched them on this idea of, “I’m going to school in Florida, you guys need a bunch of people in Florida to use Square, there’s all these local merchants in Gainesville, why don’t I do that for you?”

It started small, and then we ended up building this whole network of about 250 people across the US, who were at all these different colleges, who ended up basically becoming SquareU reps across the US. They were basically getting local merchants in their college towns on the Square. Through that, I ended up dropping out of school, coming out to San Francisco, and then that’s when I started at Gumroad and my journey here sort of began.

[0:09:37.0] JG: Talk to me about like, what was going on in your mind at this point, because it all sounds really quick, but I wonder what it felt like at the time. Going to Africa for a summer to be in the midst of this really interesting thing, and then you told me once that if you never went to Nairobi, you never would have gotten to San Francisco. At least, I think you told me that.

What I think is so fascinating is you look back and you go, “Man, if I didn’t make this decision, where would I be today?” I’m just curious, do you remember what it felt like in that moment to — before you decided, “I’m going to Nairobi,” or, “I’m going to drop out of school and move to San Francisco,” what do those decisions feel like when you’re on the brink of making them?

[0:10:21.9] RD: Yeah, I have this theory that we way overestimate the downside of decisions, and potentially way underestimate the upside, especially in the moment. I think I also had some serious naiveté in the way that I viewed things. I remember literally thinking, I remember actually not even being nervous about going to Nairobi, which is this really weird feeling. I didn’t know anyone there. I’ve never been to Africa, and I literally remember packing my bag and my parents dropping me off at the airport and just not even — was not even scared in the slightest bit.

In retrospect, that’s insane. Why would a 19-year old go over to Nairobi, sight unseen, land at the airport, figure out how to get a house, and you know, live there for three months without being at least a slight bit nervous.

I’m nervous now thinking about me doing that. I just think I sort of like was able to push through that, and then I remember thinking about when I was dropping out of school, I remember just sort of like running through the actual worst case scenario was that I leave school, I join Gumroad, I get a year in and Gumroad doesn’t work out, and I decide you know, go back to school. It’s basically super simple at that point, you just go back to the university and say, “Hey, I want to finish my last year here, and make it happen.”

I remember just thinking like the worst — it seems insane and seems crazy, and it’s a sort of like you know, weird thing to do. Less weird in San Francisco, but you know, certainly on the east coast is sort of a little bit more odd. I remember just thinking, “This actually — the downside here is actually not that big, and the upside is actually huge.”

Which is sort of the way I’ve started to process through a lot of decisions. In retrospect, I think they look maybe a little bit crazier than they were, but it all sort of seem to flow in the moment.

Click here to download a free PDF of the complete interview transcript or scroll down to continue reading it below.

[0:12:00.7] JG: Yeah, interesting. What did your parents think about it when you decided to drop out of school?

[0:12:06.2] RD: I had this great — I’ll never forget this conversation with my parents. I was super nervous about just what they were going to say, and I mean, my parents are super gracious, and they paid for my entire college education, and so both of my parents are super smart and education was really important to them.

That was something I was nervous about, was when I was telling them like, “Hey, I think I’m going to drop out of school.” I remember my dad saying he was super happy, and then he followed it up by something like, “You know, you probably should have never gone to college in the first place.”

I sort of just in that moment felt this — I felt really known, but then I also felt like it was this very humble remark form him, because my parents were the ones that pushed me to go to college. I don’t think I had identified that maybe that would have been a better option, just to go straight into trying to start companies and figure things out.

For him to not just say, “I’m excited for you,” or “You’re making the right decision,” but to go so far as to say, “I think you’re amazing. I think you don’t even really need this.” I see the benefits of it totally now, and I’m glad I did it, but that was a moment for me where I just felt very known, and very like he was proud of me, and he totally supported what I was going to do.

[0:13:19.0] JG: Your family is interesting to me, just because it says a lot about where we come from, but is there a history of entrepreneurship in your family? I know your dad ran or runs a ministry. What about grandparents and over family members?

[0:13:36.0] RD: Yeah, most of my dad’s family is super entrepreneurial, and my dad is as well. Both of his brothers either have started companies that have been very successful, or are executives at publicly traded companies and have had great careers.

Then my grandfather has an incredible story, and the super quick version of that is that he started literally doing a co-op at Georgia Tech. He couldn’t afford to pay for school, so he’d work a semester at BellSouth, at sort of the bottom of the rung as an engineer, and then go to school for a semester. It took him twice as long to finish his school at Georgia Tech, and then ended up as one of the top executives of all of BellSouth 25 years later.

He did this sort of corporate thing, working on himself all the way up the ladder. It was just super inspiring to me, and sort of set this tone of sort of achieving excellence in business, I think, with my whole family. Then for my dad and his brothers, they sort of went the path of starting companies and doing a similar path. My dad decided to go the ministry route, but certainly a culture of business and entrepreneurship and, you know, doing interesting things throughout my family, yeah.

[0:14:44.2] JG: What did you think growing up that you were going to be or do?

[0:14:48.0] RD: it changed a lot. I thought I was going to be an athlete for a while, quickly realized that one wasn’t going to happen midway through high school, and then for a while thought I would be a worship pastor, or some sort of be in ministry somehow, work at a nonprofit, and then I think in later in high school, that sort of evolved into thinking, “Okay, I should probably do something in business.”

I had this romanticized vision of what it looked like to go work on Wall Street, and so that was sort of the new thing. I started to become obsessed with this idea of leverage, and how do you go somewhere where what you’re valued for and what you’re respected for is directly proportional to the value that you bring, and how can you have as much leverage on the time that you spend with the company and the time you spend interacting with people?

There’s literally no better place in the world for that than within the startup ecosystem. Because you don’t have this — your age doesn’t matter that much. Your pedigree doesn’t matter that much. What matters is being able to execute, do your job well, and there’s a culture that sort of helps those types of people rise to the top faster than basically their industry.

You know, if you’re the type of person who can come in and execute, and get things done, and work at a really high level, the opportunities and the sort of rate that you can build a career and build social capital is greater than any other industry.

[0:16:06.9] JG: How did you put that together? How did you realize that like the best leverage you were going to get would be to go work at a tech startup?

[0:16:15.3] RD: I think it was probably after my first summer with Gumroad. Started as an intern there and…

[0:16:21.8] JG: You were out in San Francisco at that point?

[0:16:24.0] RD: Started working while I was still in the University of Florida out here. I was an intern, but I didn’t publicize that. I just said I was working on Growth and DD. I remember just, as an intern, pitching executives at massive music labels, and you know, trying to get deals done with them.

They didn’t really care that I was that young, because I was working a tech company. It sort of just made sense. Our investors didn’t care, the board didn’t care, a lot of people on the team didn’t care. It was sort of like well, Ryan can close deals, so nothing else really matters besides that. I quickly realized that there was a culture that would sort of value execution and getting the job done over anything else, versus other industries where age plays a huge role, time at a company, all those types of things really matter a lot.

[0:17:09.5] JG: Yeah. This is like the thing that I admire perhaps the most about you, is your ability to not only connect with people, but really connect with them without agenda and just genuinely try to help them. You’ve done that so many times, and for so many people, that it’s made you really good at that. It’s helped grow the businesses that you’ve been a part of in massive ways, at least that’s my observation.

Where does that come from, Ryan? I want to ask you how you do that, but first I want to know like, how do you even know how to do that? How did you even know, as an intern, to be so audacious to reach out to these people that most people are going to go, “That person would never give me the time of day.”

[0:17:54.3] RD: Yeah, that’s interesting. I don’t know if I’ve ever thought about it like that. I think a pretty big guiding piece for me was Chris Sacca, who is one of the investors in Gumroad. He’s one of the best tech investors of the last decade.

He said this thing to me which is -I think he said it in a talk, and then we talked about it later, but he said, “Add value before you ask for value,” and that was basically his whole thing, was you know, before you approach someone asking for something, you want to bring something of value to them.

I realized quickly with Gumroad that we had this really interesting data set for anyone who wanted to sell things online, which was things like conversion rates by channel that no other platform was giving anyone. So we could say, “Hey, here’s the average conversion rate from Facebook, versus Twitter, versus YouTube, versus SoundCloud, versus your blog, versus an email newsletter. Here’s how much money you can expect to make from all of those.” I realized that anyone who was in charge of commerce at any big company cared a lot about that data, and they really weren’t going to get that from anywhere else, because iTunes and all these other places obfuscate that.

I just started reaching out to people and talked to them about Gumroad. I would end the call or email with saying, “By the way, we have all this awesome data, regardless of whether or not you choose to use Gumroad, I’d love to send that to you. It would be helpful, regardless of what platform you use, to understand how to do better marketing.”

That offering of giving them something for free created this trust, and also this respect, I think, and established us as someone who they respected or wanted to do business with. I think that applies to everything in life. Recruiting, friendships, raising money for startups, investing in startups. Like if you can sort of approach things not as this transactional, “what can I get out of this right away,” but, “How can I add value,” that’s sort of a really helpful framework.

Then the other piece for me is I enjoy meeting people, I enjoy knowing people. Some of the people that we technically did business with at Gumroad are now some of my closest friends. I’ve been to their weddings, I’ve been at their bachelor parties, they’re legitimately friends that I’ll have probably for the rest of my life. I think that’s probably something that’s less strategy-driven and more just personality driven. I’ve just really enjoying connecting with interesting people and wanting to build authentic relationships.

[0:20:08.3] JG: Is there an example of a time when you weren’t trying to get something out of the relationship at all? Because I think even when you go in and say, “Hey, I’m going to-“ I’m thinking for myself here. You go into it like, “I’m going to help this person.” It’s kind of hard to silence that thing at the back of your head that says, “Maybe this could potentially lead to something sometime.”

I’m wondering, was there a time when that voice wasn’t going on the back of your head, and you were just going, “I’m just going to help this person,” and then some crazy opportunity happened as a result of that?

[0:20:38.3] RD: Yeah, let me think about that. I’m sure there is a good one.

[0:20:41.5] JG: It’s my job to stump you.

[0:20:43.0] RD: That’s good. Yeah, a good example of this is we have, we worked with a lot of really big artists at Gumroad, and there is one particular hip hop artist, who’s arguably the biggest hip hop artist in the world.

[0:20:56.9] JG: Who will remain nameless?

[0:20:58.4] RD: Who will remain nameless. I had known his team for a while, and I had met these guys who were working on a really cool, sort of like a new web platform for artists and creators to manage their websites. It’s like WordPress but for artists. Some super cool integrations.

I just pinged them. I said, “Hey guys, this looks really cool, I hope you’re doing well, we haven’t talked in a while, but I thought literally this might just be helpful for you. I talked to these guys, and they’ll basically give you 50% off for life if you want to try it out.” They tried it out, they ended up loving it, and you know, it was like this [unintelligible] conversion rate sort of thing. It solved all these headaches for them.

I remember I legitimately was just thinking in my head, “This would be cool. They would enjoy working together, let me hook them up.” That basically became like the foundation for a bunch of other conversations around like, “We really appreciate you teaming that up. Is there anything we could help you? We want to learn more about Gumroad, there’s probably some ways for us to use it.”

Then fast forward three years later, and they probably did 10 million dollars in transactions through Gumroad or something like that. Obviously, I made a lot of money off that, but that was like a good example of something that started as something that was just legitimately trying to do a favor and help people out, and then spiraled into something pretty big.

[0:22:15.7] JG: This is something that I think, like we think is obvious, but most people are kind of terrible at it. Just giving before they try to get, being outlandishly generous, and not being afraid that they’re going to be taken advantage of. Do you see that, or am I just too critical?

[0:22:34.8] RD: Yeah, I think part of what drives that is, there’s a lot of people that operate, I think, with a framework for business where everything is about, like if you’re a sales person, it’s just like, how many people can you get in the door? How many people can you close? How many people can you meet with?

It’s all about sort of everyone becomes a number. I think that if you’re in a competitive environment, if you’re trying to grow a company, those things are valuable. You want to have people that are very driven by just how many people can I get through the door, how many deals can I get done. I think there’s an element of humanity that doesn’t actually take away from the growth of the business or your success as a professional.

For me, it’s like keeping in mind the humanity of people, and people respond well to things like this, and they don’t respond well to feeling they’re being sold. I think I’ve had people that assume that my ways that I interact with people is just a shtick, and I just sort of act like I’m friends with people because it’s convenient, or I’m super friendly with someone or try to help them all so I can get something back in return.

I just found that defaulting to trying to always be helpful is sort of a pretty good default to live with in your life. You end up, you know, through that, connecting a lot of interesting people, connecting with a lot of interesting people, and being able to build authentic relationships with people. I think if you’re playing the long game, that is a much more strategic and even enjoyable way to live life than just trying to optimize every interaction for what you can get out of it or what your company can get out of it.

[0:24:09.1] JG: Yeah, I agree with that, I love that. I think that you don’t realize that this is a sustainable way to live, where you’re not going to get taken advantage of all the time or whatever, until you try it and you go, “Wow, this works. I can help people and not worry about how they’re going to help me back, yet, if I do this enough, I’m going to be okay.” I think it’s maybe a little bit of an act of faith to step out and do it, but like you said, just a better way to live, where you’re not looking over your back every moment.

[0:24:41.1] RD: Yeah, you’re way less stressed about interactions. Everything’s better.

[0:24:46.6] JG: Practically, because I think you’re a pro at this. I saw some Twitter conversation at one point where, I don’t know, somebody who was saying something about “you’ve got to get something out of people, you can’t just go around helping people” or something like that. You just said, “Look, I try to help everybody I possibly can without any sort of agenda,” and I chimed in and said, “Yep, that’s true!”

Anyway, I think you’re the best person I know at this, without exaggeration. What are some practical things that people can apply, in your experience? If they just want to be better networkers, better connectors, because you do this well, and I think part of it is, you know, most of it is the generosity of spirit with which you approach things, but you’re also really bold, and I’m just wondering what are some quick tips for how to be a better networker, how to be a better connector of people?

[0:25:37.1] RD: Yeah, I appreciate the kind words. I think probably the biggest thing is that people — I think a lot of this is just having the willingness to spend 90 seconds or five minutes when there’s an opportunity to help someone. I get a ton of emails in my inbox that are people asking for help, or advice, or intros, or whatever.

Often times, the response to those emails, or you know, a text or whatever is maybe like a 90 second thing, or firing off an email to someone else and saying, “Hey, would you be up for meeting this person?” That is — if you think about that as the value that can create for that person’s life, for your relationship, for all those things. In the moment, it’s kind of hard. I don’t want to send that email, but if you just do it in the moment, you get the email and you see it, you just fire it off, that’s kind of been my MO over the last few years is just taking immediate action when I know that I can help someone.

The other thing is, I think this is just some sort of — it’s a pretty basic thing, but I think a lot of people don’t do it, is we’re horrible at sort of conceptualizing and remembering our relationships, just as humans. There’s all these studies about how you can’t really know more than 150 people or 200 people.

I found that I literally just have to write everything down. I use Airtable, which is a database software, and literally everyone I meet, anything interesting that happens, or anything that I need to remember, kid’s birthday, whatever. As soon as I’m done meeting them, I just drop them into Airtable. Then it’s all searchable, and so every time I meet someone new, if someone introduced me to that person, then I add them to Airtable, and then I put who introduced us. It’s not like a sales thing. It’s just a pure, “I know I can’t remember all this stuff, but it’s really valuable information.”

So multiple times a week, someone emails me and says, “Hey, I’m working on this thing. What do you think?” And I think in my head like, “I think I know someone who used to work on this, or used to work with this, or who would enjoy this,” and I’m able to find them by some random search query, because I remember that when I met them, they told me about their dog who is whatever, and I search based on that and I found it.

I think just remembering the people that you know, and the types of people they want to meet, and I think I’ve done this. Like I remember Nathan Barry. He and I were friends, and I remember thinking, I think he was in San Francisco and I was like, “You should meet Jeff Goins at some point.” For him, that was super valuable. You were like a very valuable person for him to connect with at that stage of his career. I think you guys have become friends at this point.

I think people — often times intros and connections are very one-sided, and one person is clearly getting all the value out of it, but if you really try to make connections with people and link people up who can both enjoy it and both get value out of it, the compounding effects after five years of doing that become pretty significant.

[0:28:23.5] JG: Yeah, I was going to bring that up, and actually just sent Nathan some hate mail, so I wanted to talk to you about that. I didn’t really appreciate that intro. No, that’s an interesting way to think about it, like how can this mutually benefit both parties in trying to make the connection valuable to both sides, and also I like that you mention this, and I think a lot of people don’t think about this, but you said, “I email the person, or text them, or whatever and say, ‘Hey, would you be up for talking to this person?’” I see so many people cold-intro people.

[0:28:57.0] RD: Oh my word, I cannot stand it.

[0:28:58.8] JG: Yeah, “Hey, I want to meet Tim Ferriss. Send an email to him and copy me.”

[0:29:03.6] RD: Never. If you are listening to this, literally never do that.

[0:29:06.8] JG: Yeah, Chris Brogan, I heard him talk about this, and he talked about the double opt-in. He called it the double opt-in, of like, if you want to meet my friend the cookie maker, I’m going to ask my friend the cookie maker, “Hey do you want to talk to — Here’s somebody who wants to talk to you, here’s why I think it would be valuable to you. Do you want to connect with them?”

Somebody cold-introed somebody they knew to me the other day. I was like, “Oh gosh, here it goes again,” and this guy goes, “Hey, I don’t want anything from you. I know you just had a baby. I know you’re working on your next book project. I have a few stories that are maybe useful to you. If you want them, let me know, otherwise I’m just happy to connect whenever.” It was a great email. He was like, “Hey, what I want to say is do you want to do a webinar, but I’m not going to do that. I know you’re in the middle of something. I would love to help you with any part of that,” and I was so relieved.

The fact that I was relieved made me realized we have a problem here with how people get connected, where I’m getting an email with a cold intro, with “Hey, you should meet this person,” and I’m dreading it, because I’m thinking it’s going to be all one-sided. So I love that when you connect with somebody, and you go — like Nathan or this person I just connected with — and you think, “Wow. All of the sudden I’m very interested in talking to you.”

I think you, Ryan, understand something that a lot of people don’t understand, which is if you’re that guy that cold intros everybody, people stop trusting you.

[0:30:35.8] RD: Totally. You’re creating work for that type of person.

[0:30:38.9] JG: Yeah, right. Like when you introduced me to Nathan, I was like, “This guy has never asked me for anything in my life, and I keep trying to find ways to make my friendship with him worthwhile. So if he’s going to introduce me to somebody, it’s going to be worth my time, because it’s not going to be one of those one-sided things.”

Yeah, that’s great. Okay, one more question for you, because I think this is always fascinating to me. You talked about briefly, “I thought I might be a worship pastor at some point.” I know you’re a musician, and at some point, I thought you told me at one point like, “Man, this is what I’m going to do. I’m going to play guitar for churches, and this is going to be my thing.” Going into tech, and marketing, and entrepreneurship, launching and growing companies in San Francisco, I think is a bit different from being a professional musician and working at a church.

My question is this, how did that being a creative being, a musician, how does that influence or affect the work that you do today?

[0:31:42.4] RD: Yeah, that’s a great question.

[0:31:43.9] JG: Like, do you look back and go, “Oh man, I should have been learning how to code at eight years old,” or maybe you already know how to do that. I mean seriously, do you look back and go, “I should have been doing all these things earlier”? Because you got an early start, at least from my estimation, but it’s interesting the path that you got there.

I’m just curious about how you think about the things that got you to where you are. I always find it fascinating when somebody says, “Oh, I was going to do this, and I end up doing something that sounds completely different.”

[0:32:13.9] RD: Yeah, being honest, I’ve never thought about wishing I had done anything earlier, actually. I don’t recall ever having the thought of “I wish I had learned to do this” or “I wish I had spent more time on this earlier.” I think the thing that I learned through, the thing that my parents did a really good job of and I learned in high school and college is just how to think well. I think understanding how to solve problems, understanding how to inspire people to do, whether you’re leading a team with a non-profit, whether you’re leading a company, whether you’re leading a band.

Whatever it is, I think there is this universal ability to get humans excited about something, and excited about operating at a higher level that is super transferable, and in some ways, I think there’s things that people don’t… I think that is one of the secrets to great recruiting, is that you can find roles or skillsets or jobs where people are really good at those types of things that aren’t immediately obvious, and they’re not Stanford grads that worked at Facebook for four years and now you are trying to poke them into your company.

So yeah, I think that was a big piece of it, and then I also think for me, I very much treasure each phase of my life I guess whether it was companies that I was at, or there was things that I was spending my time, whether it was college or high school, aspirations that I have. I look back on those all those memories very fondly because of the relationships and new experiences that I had, and so I really view each of those as a pretty key piece of my story. There’s not really this sense of wishing that I hadn’t spent as much time, or invested less in different things which I could see.

Now that I think about it, I could see that certainly being the case but yeah, that is not something I really thought about.

[0:33:58.2] JG: I just wonder if being a musician, a lot of what you did, at least when we connected in Nashville when you were in town for business working for the government, I’m sure you’re meeting with a lot of managers, record companies, artists, I wonder if that gave you an advantage at being able to connect with at least those artists?

[0:34:16.9] RD: Yeah, I do think, and that was interesting, is I was sort of in between wanting to be a worship pastor and wanting to go to Wall Street. I thought I was going to go work at a record label somewhere. I actually even thought about transferring to some really good professional music like…

[0:34:36.6] JG: Belmont?

[0:34:37.3] RD: No, Middle Tennessee State, I think.

[0:34:40.1] JG: Oh yeah, MTSU.

[0:34:41.6] RD: Yeah, I think it’s got a really good artist management program or something.

[0:34:45.1] JG: It does, yeah.

[0:34:45.7] RD: And so I was thinking about transferring there, and it was funny how I went to work at Gumroad and then it all came full circle, because I remember actually this very interesting moment on Google Maps Street View, like going down Music Row as a freshman in college, thinking like, “This would be really cool to work here or whatever,” and then I remember three years later or whenever, literally just taking meetings all day down Music Row, and closing all these deals with artists, and thinking how it came full circle but in a very roundabout way.

So yeah, I definitely think there’s this interesting sense of like, each piece of our story is coming back together, and things that you wanted to do still happen, but it’s a different permutation of it, or it looks very differently, but you still get a cool taste of that piece of life or whatever.

[0:35:35.1] JG: Yeah, it’s interesting. So tell me about what are you doing today? You’re working with this really interesting startup, Omni. Tell me about it.

[0:35:44.1] RD: Yes, as soon as I left Gumroad, I really wanted to either start a company or work on a product that was solving a really hard problem that existed in the real world. So not something that is purely digital, but something that was a physical business, and just looking at the different opportunities that exists across different physical businesses, whether it’s deliveries, or transportation, or real estate. The idea is very clear that storage, personal storage, like Public Storage and U-Haul, it was this huge opportunity that no one was really attacking well.

Not just on the face of it of like, “I can build a better storage company,” or we can make storage more convenient or more easy to use, but this vision of you have all these items that are just literary trapped in these — it’s not inventoried, no one knows what’s in there, when people default on their payments they just auction it off and then open it up and make an HGTV show about it, and there’s all these things, there’s all these items that are sitting in places and no one is doing anything with them that you can’t tap into them.

And so thinking about this idea like, what if there’s transparency to all of this, and what if it was really simple to just store individual items that you don’t need, to get them back delivered to your door whenever you want them, and without revealing too much of where we’re headed, you can always imagine all these interesting things that can happen once you know what people own, and what they use, and what they don’t use, and the friends that they have, and so thinking about this idea of what if we can really build something that would change the way that you interacted with your stuff?

The way that your friends borrow stuff, that you sold stuff, that you bought stuff. In the same way that Airbnb created this marketplace and this way to tap into this dormant space that we have in our houses, a guest room, a guest house, whatever, and give us a really easy way to sell that and make money off of that. We think of storage the same way, of all these items that you don’t use, you have this excess. Public Storage, for example, is a $40 billion publicly traded company, and they’re just sitting in a room in aluminum boxes, basically.

So yeah, that’s what we’re building. We’re just live in San Francisco right now, so just within the city limits. So if you’re in San Francisco and you want to try us out, email me and I’ll give you a discount code, but yeah, we’re going to be expanding rapidly and going to be doing some really interesting things once we get the core product out there.

[0:38:03.3] JG: It’s cool, I mean my observation is this is the direction of the tech world. Not that I have any real sense of what that is, but my observation is, a few years ago it was all about software or intangible stuff, and now, there are all these really interesting startups for the past several years like Uber, like Airbnb, like Omni, where it’s using technology to connect to real world tangible needs. Like, “What am I going to do with my stuff, where am I going to put it?”

It’s fascinating to see things, in some ways, come full circle and how technology is, instead of pulling us away from everyday lives, it’s helping us do those lives better.

[0:38:52.3] RD: Yeah, exactly, and that’s what we’re all about, is how do we improve and augment people’s lives? I think it’s a sort of unique opportunity where you can genuinely make people’s lives better, and the way they interact with their possessions better, and there’s all these ways that you can improve people’s lives, and it’s fun to work on a product similar to Gumroad, where we were making creators lives better, but at Omni, it’s much more broad and the people that can use Omni is a much larger sort of a sub-section of humanity.

So yeah, it’s fun. We launched three months ago, so we’re still pretty early, but we’re growing fast and working on coming to other cities soon.

[0:39:28.0] JG: How do you know, Ryan, when something is a good opportunity? I remember listening to this podcast StartUp, have you listened to that yet?

[0:39:36.7] RD: A bunch of people have told me to, but yeah, I haven’t listened to it.

[0:39:40.0] JG: The most interesting episode is episode one or two, where he pitches Chris Sacca on, “Hey, invest in my company.” Chris says, “No,” and then gives him all this feedback, and it’s super interesting. Chris talks about Airbnb, because he invested in Google, Twitter, all of these — or he worked for Google, invested in Twitter, did all of these things that made him a lot of money, but then he talks about all of the things that he didn’t invest in that he thought were stupid.

And he’s like, “I was an idiot. I had no idea.” Similarly, you were talking about, you were listing all of these companies, Square, these companies that have now become successful startups, at least from my perspective, and you left a very secure, high-up position at Gumroad, as the first employee, to do something new. What goes through your mind when you’re calculating that risk and deciding, “I want to do something brand new, I don’t know if it’s going to work or not.” How do you know that this is a good bet versus a risk that’s just not wise?

[0:40:42.6] RD: Yeah, that’s a great question. So what I look for is, specifically with evaluating companies, the number one thing is always the team. Is it people that you would want to work with, and this applies, too, if you’re investing in a company or going to work at a company. Is it people that you look up to, people that you’re going to learn from, is it people that you’re going to be excited about doing potentially the hardest work of your life with.

If they’re in the office early, are you more likely to come into the office early because you want to hang out with them, or are you dreading having to be in the office with them? That’s a really good benchmark for the culture and the types of people that work there, and then as far as the actual opportunity, I think a lot about this concept of layers, and the most interesting companies are the ones where you have the initial product that’s interesting, that makes money.

Ideally it’s profitable, and you could build a good business off of that, but once you get that in place, that platform unlocks opportunities that create drastically more value, and turn a good business into a great business, or even a legendary business. So you think about Uber as, I think, the prime example of this, as they built an entire company in the last five years entirely focused, until recently, on literally just transportation.

Human transportation, and it was all about opening the app, finding a driver, they come to you, get in the car, you drive away, but what they’ve done is they’ve created a mesh network on top of hundreds and hundreds of cities across the world of their drivers, and they’ve trained you that when you want to go somewhere, you can pull this app, you can click a button, and you can get there. Then the huge shift for Uber over the next five years will be shifting you from understanding that they can take you some place, to that you can leverage that network for anything you want.

You can have food delivered to you, you can have a parcel delivered to someone else, you can have a gift delivered to someone, that network that can be used for almost anything when it comes to local logistics. They had to get this first product in place, and then get a bunch of people using it, and get drivers on the network and help people make money, building good margins, but then now, they can unlock this massive layer that I think way can be bigger than the transportation piece of their business.

I think that’s the way that I think about the best companies in the world, are companies like that, where they have this second or third layer that they can build in once they get the core product done, and I think that’s an interesting way to think about opportunities. Whether you are thinking about joining another company or starting a company, once you achieve that first vision, is there a multiplier effect on top of that with something really interesting you can do with that user base?

Facebook is another example. They’ve got a billion users on this core social platform, and now the things that they can do with that, with payments inside of messenger, where all of a sudden they are doing peer to peer payments. There’s all these other things they can build on top of it that they are able to do because of the network. So I think that’s a pretty good framework for thinking about really, really good opportunities.

[0:43:28.0] JG: Yeah, that’s interesting, like Google owning search, and initially not making any money off of that, and then creating all of these free and paid products around that, and around being the search engine. Yeah, that’s fascinating. Cool. Well dude, I always learn so much from you, and so I’m inspired and encouraged to watch your journey unfold. Thanks for being my friend, and thanks for being a part of this.

[0:43:56.8] RD: I appreciate it, Jeff, and thanks for having me on. This was awesome.

[0:43:59.2] JG: Yeah, you bet.

Before you approach someone asking for something, you want to bring something of value to them. –Ryan Delk

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