Transcript
Ben Casnocha:
And, Reid, today we’re gonna be talking about the art of the hustle.
Entrepreneurs are sometimes defined as people who are relentlessly resourceful; people that will walk through walls, live on ramen noodles for years as they get their company off the ground. So when we think about the strategies and techniques that entrepreneurs employ when creating their businesses and applying those to careers, this is a body of work that’s super relevant.
If you wanna be more entrepreneurial in your career, you can take a lot of inspiration from these entrepreneurs that do so much with so little. And, you know, one of the teams that you backed early in your formal venture career, Airbnb, had a pretty incredible journey of rejection and iteration and hustle.
And they did a set of things that were super clever and creative in their early days, which I think embody what great hustle is all about. And wondering if we could just start by hearing a little bit about Brian Chesky and co’s efforts to raise money and stay alive in the 2008 presidential campaign.
Reid Hoffman:
Brian, Joe, and Nate—three awesome entrepreneurs, you know, good friends—and part of what they did is they would go and they would pitch the business a lot, and basically everyone would go, “I don’t really see this as a business,” etc.
And it was like, “Okay, we’ll admit you ‘cause you got a lot of hustle,” but they got tons and tons of no’s, including to the point where, you know—
Ben Casnocha:
They’re raising money for Airbnb.
Reid Hoffman:
Raising money for Airbnb—which obviously today looks crazy given how successful and world-transforming that Airbnb is, but back then was the typical thing.
And then, so in 2008, they’re running on fumes, they’ve maxed out credit cards. They’re literally kind of living in an apartment by themselves and Airbnb’ing out a, you know, kind of an air mattress in the living room when they need to in order to—
Ben Casnocha:
To make their own place a—yeah.
Reid Hoffman:
In their own place. Yes. Right.
And so they came up with a clever idea. They said, “Well, actually, in fact, along with these presidential campaigns are—when the conventions come together—are a time where it’s a classic place where an Airbnb would be an awesome platform for everyone, an awesome platform for the travelers, ‘cause all the hotels are booked out and people are trying to get in; an awesome opportunity for the host because of like, you know—even frankly, a couch or a air mattress in the living room—like there is no housing. So like you have a chance to make some more money with just that. And it could be a spare bedroom. It could be you’re out of town. It could be renting the house. It could be all kinds of things.”
This is a canonical, you know, surge thing for Airbnb and it could be the, ‘Oh, I saw it. It was really useful. It was awesome to me. Maybe I should become a host. Maybe I should—when I’m taking that vacation to, you know, Italy, maybe I should actually look for an Airbnb versus a hotel. It’s an awesome customer development thing.”
And they said, well, how do we fund all this stuff? And how do we make it happen?
And because, you know, these are designers, which is the atypical, you know—
Ben Casnocha:
The founder’s backgrounds were design and industrial design.
Reid Hoffman:
Yes. Yeah. Nate was CS, but the other was in industrial design—
Ben Casnocha:
RISD grad, yeah.
Reid Hoffman:
—in RISD, and it kind of tells the lie to, “Oh, everyone has to be a CS entrepreneur.”
It’s no, no, no. Their design background was part of what gave them the creativity to create the things that were relevant to make Airbnb the magical surprise that it is.
But they said, “Well, actually in fact, one of the things we could do is we could make and sell cereal. We could have Obama O’s and Cap’n McCain’s. What we’ll do is we’ll make a bunch of cereal boxes. We’ll sell them at kind of like high-end tchotchke.” I think it was $40 a box or something.
Ben Casnocha:
Yeah. Obama O’s are like Cheerios. But Obama O’s.
Reid Hoffman:
Yes, exactly. And then Cap’n Crunch, but Cap’n McCain’s.
Ben Casnocha:
And I haven’t had Cap’n Crunch in a long time. It sounds delicious. Keep going.
Reid Hoffman:
You might find it a little too sweet, but they did all that and they made a set of these boxes; spent a bunch of time hot gluing and everything else putting together because they were selling out, like in just droves, which of course added to the capital balance; you know, also brought in experience like branding. It’s like you’re selling a product that people say, “What’s that? Oh, it’s part of the Airbnb thing.”
So it became a artifact that was also a marketing artifact; just genius on lots and lots of levels, all the way to, you know, I know that one of President Obama’s cherished kind of possessions is a Obama O’s that’s signed by Brian, Joe, and Nate—
Ben Casnocha:
Like a box—a cereal box—
Reid Hoffman:
A box of cereal signed by them is one of the things that they gave him after he was president, so he could actually keep it. Everything—you know, when you’re given as president, ‘cause you know, Obama is super high integrity—goes in the presidential stores, but this is one of the things they said, “Okay. You know, thank you. And here is now finally—you know, years later, you know, after you winning the campaign, here’s the thing.”
And that’s one of the things he treasures as part of the, you know, his relationship with, you know, Brian, Joe, and Nate, who he also treasures his relationship with them.
Ben Casnocha:
Well, it’s amazing ‘cause today, you know, these are billionaire entrepreneurs with this massive business that’s transformed the world, but it’s easy to forget that in the early days, all these startup entrepreneurs have nothing, are respected by nobody and they have to hustle in this kind of way to get their business off the ground.
Let’s just unpack the word ‘hustle’ for a sec. Like what do we mean when we talk about hustle? What is that word encompassing? What are the sub-words or sub-concepts? And there’s kind of this funny thing on this topic that, you know, you can be a hustler and you can have the skill of hustle, and there’s some connotation about hustler that doesn’t quite sound right to us, I think.
What’s the difference between hustle and hustler, or what do you think of, Reid, when you think of hustle, and why do we get mixed up with this word hustler?
Reid Hoffman:
By the way it’s a couple of words like this, with like—also, having a network, being a networker is another one.
And I think it’s because when it becomes the noun, it tends to embody the negative aspects of it. So like a hustler is, “It’s just about me. I don’t care about you. I might try to take advantage of you.”
Ben Casnocha:
Yeah. Slightly unethical maybe.
Reid Hoffman:
Yeah. “I’m not paying any attention to the dance between us. I’m being really good for both of us. I’m just all about what it does for me.”
And so it’s kind of like, you know, well, check your wallet when you’re dealing with a hustler, you know, what’s going on…when you’re dealing with a networker, it’s like, yeah, it’s all about them. It isn’t about us, you know, as part of it.
Whereas having hustle is really good. It’s the “paying attention to serendipity, to opportunity”; being able to pull resources in that might be unexpected that you might find by serendipity, but also you might creatively pull something together.
You might go, “Oh, well if we’re gonna be doing these conventions and doing Airbnb for the conventions, how could we be really intense in the conventions? We’ll have cereal boxes.”
You know, there’s no cereal boxes about Airbnb. It’s a purely design, creative idea that’s also a marketing and branding idea. There’s also a capital raising idea as you’re doing it, you know, etc. etc. etc. as a way, and so it puts it all together. That’s hustle.
But by the way, since there’s no one who was hustled—right?—there’s no hustlers.
It’s just pure hustle, and having hustle is extremely important in entrepreneurship, and extremely important in being the entrepreneur of your own career, because you’re looking for those opportunities. You’re looking for the thing that maybe you see that other people don’t see: the way of putting things together, the way of taking a risk, the way of taking a jump or trying something that maybe other people don’t see, or are seeing an opportunity in building it.
And that’s obviously what entrepreneurs do in building companies, but also that, “Oh, if I go take that job, if I go work for that person, or if I build that soft asset, that skill—that may suddenly open up a bunch of stuff that other people don’t see,” and that’s having hustle.
Ben Casnocha:
Love it. And, you know, in the book Startup of You, we break out a few different strategies and ideas for how people can cultivate this capacity for themselves.
And the first strategy that we lay out is about being a cockroach, or not taking no for an answer, or not accepting rejection. And this is an interesting one because, of course, we’ll get to sort of the instances where you sometimes do need to accept rejection. But I think fundamentally, so many entrepreneurs have the experience of forming a business, talking to potential employees, investors, partners, customers; and having the door slammed in their face over and over and over again.
I mean, any great founder has that experience of encountering all these doubters, and oftentimes use those doubters as fuel and motivation. But the ability to get back up again, and pitch again, and try again is really remarkable.
Years ago, I wrote my—the very first book I wrote—I remember pitching dozens and dozens and dozens of literary agents and publishers and getting rejected by every single one of them. I actually still have all the rejection letters that I’ve kept all these years later. But it’s just like over and over againL businesses I’ve created, pitching investors, rejection, over and over and over again.
You know, it’s interesting to sort of unpack the psychology of dealing with rejection and mustering the confidence or chutzpah, whatever, to try again. And the amazing thing is if you can have some experience at rejection and staying alive and trying again, it can actually create a sense of self-confidence that’s really quite stunning.
Like I assume Brian Chesky and the Airbnb team today feel like they can do almost anything because of what they went through. In a much smaller sense, I do feel like—at this point in my life, I’m always like if I actually really work hard as something, I think I can be successful in almost anything. Like, I truly have that belief because I’ve had so many failures or rejection moments, and I got back up and tried again and ultimately it worked out—or I learned something important to help me in the next thing I did, so I found it valuable in some way.
Reid Hoffman:
By the way, I think entrepreneurs—myself included—by default, start with the, “The first no is never dissuasive.”
Ben Casnocha:
Yeah..
Reid Hoffman:
Now, sometimes a set of no’s should be network intelligence and should be maybe modifying your path, and I’ll get into the nuance of that in a moment, because the really important thing is as entrepreneurs—the vast majority of entrepreneurs will encounter lots and lots of no’s.
And by the way, part of—for The Startup of You and being the entrepreneur of your own life is: in the same sense, if you’re not encountering some no’s, you’re not playing aggressively enough; you’re not playing forward enough; you’re not taking enough risks, right?
You should encounter some no’s, not—you know, depends a little bit on what you’re doing and so forth, and this isn’t saying, you know, you should just be like writing letters to every CEO saying, “Hire me as a vice president!” and getting a whole bunch of no’s. That’s not helpful, right? And you’re not learning from it.
And that’s what it gets key to is: where can that experience of engaging and getting a ‘no’ still be a learning moment? Still be a “build resilience” moment? Still be a “learn something about yourself,” “learn something about the market,” “learn something about the industry,” “learn something about strategy,” “learn something about presentation,” “learn something about communications.”
Where is that moment where, if I’m engaged in that and a ‘no’ happens, I convert it into becoming stronger, advancing the project? And that learning moment from no is just really important. It’s a—also version of “Never waste a good crisis,” and “Crisis is opportunity.”
Ben Casnocha:
Now was it Nietzsche who said, “What doesn’t kill you makes you stronger”?
Reid Hoffman:
Yes.
Ben Casnocha:
Okay.
Reid Hoffman:
Although he was quoting like…from the ‘military school of life’ or something like that, but yes. It is a Nietzsche aphorism.
Okay. It’s ‘cause today most people attribute it to Kanye West, but the—the rapper—but, you know, we have to go back and find the original source of the quotation, but yeah so that’s kind of what you’re saying, right? If what doesn’t kill you makes you stronger through learning—
Reid Hoffman:
Yes.
Ben Casnocha:
—it can still be a worthwhile.
Reid Hoffman:
Yes.
Ben Casnocha:
Now how do you, like, whether it be SocialNet—even LinkedIn, PayPal, some of these sort of iconic experiences you’ve had, Reid—hasn’t always been up into the right; hasn’t been yes every time, or even most times in the early days.
How does one emotionally handle? Is this just an inborn capability that some of us have and others don’t, or can we build sort of a resiliency?
Reid Hoffman:
Well, you can definitely build a resiliency. And part of it is like, you know, kind of postmortem the no’s; talk to other people you know; life is a team sport, the ‘I’ to the ‘we’.
Like okay, so and so said no—so and said no for these reasons. How should I interpret that?
Part of it is you talking to smart and helpful people in your network: your friends, your allies, your colleagues. They may say, “Well, actually, in fact, that’s a good point. You should really think about it.”
And maybe it hasn’t surfaced before, that would increment it, they’d say, “No, they just don’t get it. It’s a wrong fit. It’s the wrong thing.” ‘Cause sometimes they say no ‘cause like they just don’t have visibility.
Like, for example, I said no to the angel round in Pinterest ‘cause I didn’t understand the fact that these pinboards were a new medium type.
Ben Casnocha:
How expensive of a mistake was that?
Reid Hoffman:
I think that was a $20 million-valued round. And you have now an $X billions—I don’t, I haven’t checked the market. Is it $10, is it whatever—
Ben Casnocha:
Unforgivable.
Reid Hoffman:
Yeah. So just you—and actually by the way, one of the funny things is people tend to say, “Oh, you invested in X—you know, like Company X, whatever that is—and that was a failure. Was that your biggest mistake?”
That’s never the biggest mistake. The biggest mistake is passing on the amazing giants that became the amazing giants. That—this is one of the things that’s great about the tech-investing business, which is: your downside is the capital you put in, the upside could be multiples.
And with that kind of asymmetric—now doesn’t mean take every bet. There’s a lot of bets that don’t work. But with that kind of thing, actually in fact if you apply some intelligence, have some network access, have some ability to do this, it becomes a very good investing, you know, portfolio as part of doing that.
And so those are the kinds of mistakes. Now for me, my very first startup, SocialNet—you know, along with my co-founder Pat Farrell, we went out and pitched a whole bunch of different VCs ‘cause Pat had—by successfully founding GamePro magazine; being its CEO; founding the Electronic Arts Expo Conference, which is like this huge gaming conference—had a great network.
So we had access, we had all the doors, we went into a whole bunch of different VCs and they all told us no—for coherent reasons. This is again, kind of network—
Ben Casnocha:
So you pitched them on the new business idea, and you got told no over and over again.
Reid Hoffman:
No over and over again. And then there was a thread in the network intelligence, which was, “Look, the business you’re pitching us on does not have a lifetime value of the customers. You churn your customers in either success or failure. There’s a limit to how valuable your business can get, you know, etc. etc.”
And by the way, that was a really good piece of intel in all these businesses. That’s now something I’ve incorporated into how I think about businesses and what things do, and it puts a cap on how valuable your business can be if that’s the characteristic of it.
Part of the reason why things like LinkedIn are lifetime businesses, lifetime relationships with customer, providing a lifetime relationship, lifetime value; not just job seeking, but a whole wide variety of things. And also, not just one-job seeking, but all-job seeking, and all-talent recruitment, and all the rest of this as part of how LinkedIn plays it—it all experiences from, “Oh boy, this whole intelligence thread that I was given that I ignored was dumb on my part.”
And you know, we kind of broadened out. We said, “We’re not just dating, we’re professional networking,” which just gave me the LinkedIn idea. “We’re sports; we’re finding tennis partners; we’re roommates.”
All of that stuff came out of the generalization, but it didn’t answer the fundamental thing. Now the very last venture firm said, “Oh, we like the idea, but we think you’re taking too much marketing risk. You should go partner with, you know, newspapers, and we will fund you doing newspapers.”
In some sense, I think we took the money ‘cause we said, “Look, we think we really love this idea. We’ll just take the money. We’ll develop it. We’ll show them.”
What we should have said is, “Well, we didn’t necessarily really think that that approach would actually in fact really work.”
Ben Casnocha:
So, so just being sure I’m understanding: the firm that said yes was the very last firm.
Reid Hoffman:
Very last firm. Yeah.
Ben Casnocha:
How many firms did you pitch that said no?
Reid Hoffman:
At least 20.
Ben Casnocha:
So 20 no’s. 21st is a yes.
Reid Hoffman:
Yes.
Ben Casnocha:
Okay.
Reid Hoffman:
And literally we had decided, “If this pitch doesn’t work, we’re gonna go to—onto other things.”
Ben Casnocha:
Do you think when you walk into a meeting like that, it’s kind of like the “you have nothing to lose” thing?
I mean, do you think you handled yourself differently in that meeting or had a certain gutsiness to it of like, “Fuck it, this is it?”
Reid Hoffman:
You know, in retrospect, maybe, in part like being less, more relaxed about it, more just cards on the table, which is the way you should be when you’re pitching, you know, investors anyway, you like—
Ben Casnocha:
It’s almost kinda like the—it kind of reminds me of like the anti-sell and we’ll have anti-sell, so it’s like, “I don’t even care if you wanna invest. Frankly, don’t invest. I don’t, I don’t—”
[They] be like, “Okay, I wanna invest.”
Reid Hoffman:
Yeah. Well, because that whole thing of when like people have a thing: “Oh, if you’re desperate—”
Ben Casnocha:
You must not be.
Reid Hoffman:
Yeah. Yeah. And maybe you’re a hustler. This isn’t hustler, etc.
Ben Casnocha:
Actually it’s a great point. Like, I think part of the problem with hustler is the over-eagerness.
Reid Hoffman:
Yes.
Ben Casnocha:
Like, if you have so much going for you, why are you so over the top?
Reid Hoffman:
Yes.
Ben Casnocha:
You know, on the hustle.
And when we think about don’t accept rejection, one of the things I think it’s crucial to clarify is when somebody has said no to you and when somebody just hasn’t responded to you.
Reid Hoffman:
Yes.
Ben Casnocha:
And in the modern economy with email overload, etc., I hear from lots of people and myself who have experienced plenty of instances where you’re following up with somebody, you’re reaching out to them, you don’t get an answer one way or the other, and you have to decide: is the non-responsiveness a no, or is it just non-responsiveness?
And I’ll tell a story of the creation of this book, Reid, in our own collaboration together.
After a lovely breakfast at Hobee’s, I don’t know, Palo—or Palo Alto Cafe, somewhere.
Reid Hoffman:
I think it was Hobee’s Town & Country.
Ben Casnocha:
We had a lovely breakfast. We talked about working on Startup of You, First Edition—you know, this is 12 years ago, perhaps—and developed a sort of a plan for collaboration.
Over the next three or four months, in my follow-up to you to align on sort of the precise next steps, I failed to receive a response, and probably sent, you know, five or six emails and there’s no reply.
And I remember thinking to myself, “Is the project off?” You know, what’s going, you know, because we had a—we had a conversation, but we haven’t codified precise next steps of what that real medium-term plan’s gonna be.
And I actually got to a point where I thought to myself, “Okay, projects off. Bummer. You know, excited about it, but not, not a huge deal.” I thought, “Well, maybe, you know, Reid gets—Reid’s a busy guy. Reid’s probably getting tons of emails. It’s probably a lot of people emailing Reid—busy times.”
Reid Hoffman:
Yes.
Ben Casnocha:
My first instinct was, “Reid’s saying no to this collaboration. Okay.”
Then I thought, “Wait, is that how I should interpret this? He’s also, he’s incredibly busy. He had all these emails. Maybe I should just make sure that it’s a no or yes, or whatever.”
And so I called your assistant at the time out of the blue, and I said, “Hey, Paola, I’ve sent, you know, Reid a few emails. Just wanted to check in. I, you know, haven’t heard back. So I just assume we’re off.” This is like around Christmas. “I, you know, so I just wanna make sure.”
I was living in—I had moved down to South America or something. I was just planning the rest—my next year. And she’s like, “Oh, well that’s funny. Let me just—just hold on for one second. I’m just going to walk down the hallway and ask Reid about this.”
And so she walked down the hallway, comes back on the phone a minute later and says, “Oh, Reid says, ‘Love to catch up with you.’ Why don’t you come by next week in person and, you know, continue the conversation?”
I’m like, “Oh, okay. You know, that’s great. I’ll be back in the Bay Area.”
And so we stop by and put together a work plan. Sometimes I reflect and I think, “Gosh, I had sent”—and I didn’t even send that many emails, I probably sent three or four emails—but I had this inaccurate narrative in my head that if someone doesn’t reply to an email, it means that they’re saying, no, they’re not interested, they don’t like you, whatever.
And I—and this is pretty prevalent. As I’ve talked to people—even myself now sometimes—people say, “Hey, I sent you those two emails. I just—I assume you’re not interested.”
I’m like, “I don’t even remember getting your email.” Like, you know, or, “I lost the email,” “I accidentally clicked archive,” or, “I thought I replied; it stuck in my draft folder.”
I mean, there are a million good reasons. I guess my lesson for myself and what I often now tell others is: don’t over-rotate on someone not responding.
Reid Hoffman:
Yeah. And by the way, just to understand that it’s not like a kind of a social hierarchy thing and so forth, although obviously some people have much more overload in their boxes.
I have the same thing. So, like, even as recently as this last week, I have occasionally gone, “Wait, I emailed so and so I haven’t heard back,” right?
And similar to your pattern, what I’ve learned is not, “Oh, I haven’t heard back because”—or like ‘piss off’, ‘not interested’, etc. I just literally reforward the email and say, “Hey, I’m just”; “In case you missed this”, you know; and you know, “Hope everything’s okay.” You know, like, you know—
Ben Casnocha:
Well, it’s actually, and it’s interesting. One of—I can’t remember if we—I think we’ve spoken about this.
I’m really intrigued by like this issue that some people have guilt over non-responsiveness. I’ve had this too, where, you know, entrepreneurs/someone will follow up with me a few times and I’m like, “I should have replied to this earlier.”
And there’s a procrastination effect—procrastiflation, which has been my favorite portmanteau, as you know: procrastination and inflation—where it becomes harder to respond, and the guilt starts to pile up.
If someone’s replying on the same thread, I’m looking back at my Gmail, I’m thinking, “Oh my God, this is like the fourth follow-up in the same subject line.”
So putting myself in the other person’s shoes, sometimes what I have done in the follow-up is: I’ll actually do a brand new email. I won’t forward the old email, and I’ll allow the other person to almost encounter the interaction as a first interaction, and, “Hey, they replied to me within 24 hours! That’s great.”
Reid Hoffman:
Yes. ‘Cause because maybe they are also experiencing—
Ben Casnocha:
They might have a paralysis related to guilt because they’re like, “Oh my God, you sent me this email what? Three and a half weeks.”
‘Cause then you start the, “Hey, so sorry for this slow response.” It becomes this whole apology thing.
Reid Hoffman:
Yes. I frankly have enough of those that I should just have a little cut and paste of “Apologies for getting back to your late!”
Ben Casnocha:
Oh my God. Oh yeah. Yeah.
Okay, let’s talk about a second strategy, which is tweaking the approach.
Sometimes the art of the hustle is just being creative about a slight reframe of how you’re presenting yourself or presenting your idea. And we tell this story of Chris Sacca in the book.
Chris Sacca is today a billionaire climate investor.
But once upon a time, not too long ago, he was an unemployed lawyer with lots of student debt sneaking into the kitchen of event venues, trying to break into effectively tech industry events to network with people, and see if he could cook up some sort of career opportunity.
And his issue was he had a business card that just had his name on it. Just “Chris Sacca”: just a name, and a phone number, and email address, and people weren’t super impressed by that.
So he had this kind of novel idea of inventing a consulting firm. I can’t remember what the name was, but it sounded very consulting-y. The consulting firm employed one person, which was him.
He didn’t create an LLC. He just literally created the organization as a brand, put that brand on his business card, a fancy URL website, email address.
And as he started giving out his business card at events, with this kind of business card he got a lot more interest. A lot more people: “Oh, you must be a legit, you know, consultant in business and technology.” A small little tweak, but that made a big difference in terms of how people perceived him.
And I do notice this is where I think people who are great at hustle do have this sort of creative sense about them. Like they know a clever way—even in terms of following up and trying to get someone’s attention—like a clever way of gaining mind share and perhaps seeming more credible or seeming more exciting than they would otherwise.
Reid Hoffman:
Well, I think there’s a bunch of different things that kind of go under the hustle thing.
You know, not the least of which is, you know, invest in your LinkedIn profile because it is also where people find you and people will look you up—
Ben Casnocha:
Look you up. Yeah.
Reid Hoffman:
And most often now, probably it’s the most common thing when people say, “Oh, this person. You know, who are they? What should I do? I’ll look at their LinkedIn profile.”
Or, “I’m looking for people who are really, really good at, you know, kind of marketing NFTs. Who’s really good at that? Well, I’ll, I’ll search on LinkedIn for that.”
You know, that kind of thing is as a way of doing it. So there’s a whole bunch of things. But I think within the hustle, it’s how do you put your best foot forward?
Doesn’t mean mislead, right? A consultant practice with employment of one with a website is not misleading, and doing the things where you go, “Ah”—because by the way that is substance, right?
Ben Casnocha:
Yeah.
Reid Hoffman:
Which is the: you’re on ball enough; you’re careful about this; you’re doing it with some intelligence about how you’re presenting, and how you’re building your network, and how you’re interacting with your network as a way of doing it. And that that is how you put your best foot forward.
Ben Casnocha:
‘Cause so much of this book of this, all these ideas intersect with network.
Reid Hoffman:
Yes.
Ben Casnocha:
So you talk about LinkedIn profile, but also I love this example of how do you apply hustle to how you build your network?
Reid Hoffman:
Yes.
Ben Casnocha:
And there’s so many things here, but among others, it’s like: being a little bit more diligent and understanding the connection path to people you’re trying to meet.
Reid Hoffman:
Yes.
Ben Casnocha:
So people who have good hustle—like, when I think about the sorts of people I interact with who have great hustle, one of the things they do is—like a founder we backed at Village Global just sent me a note the other day about Series A investors he wants to pitch. And he went through my entire LinkedIn graph and pulled out eight VCs that I’m connected to and said, “How about this?
How about this? How about this? I can write a forwardable email for each, subject line, da, da da.” Like the whole…best practices for how to get investor intros.
And that level of hustle of: there’s a sort of proactiveness to it; there’s a ‘no task too small’, like it’s kind of grinding administrative work to go through someone’s LinkedIn connections.
But to do all that upfront—on the receiving end of that, just filled me with feelings of admiration and excitement to support this entrepreneur. Like it makes me think that he will be more successful in his business in life because of these small little things he’s doing to make the process of expanding his network in this case be more successful.
Reid Hoffman:
And what’s more, you have a higher degree of confidence about making the intros to people ‘cause you know, well he already applied this much diligence to this part of the process, right?
Ben Casnocha:
Yeah.
Reid Hoffman:
If he’s gonna be as diligent about the meeting and the prep and presenting well and everything else—because the mechanism I use on LinkedIn for when I introduce two people is: will both people thank me for the introduction even if an item of business doesn’t happen?
“No, thanks for the introduction. Yeah, I met them; not right for me, but thanks for the intro.” Right?
Ben Casnocha:
Yeah.
Reid Hoffman:
And that’s where you wanna be is: where the two people you’re introducing are both like, “Thank you for that.”
Ben Casnocha:
Yeah. When I think about hustle and network-building, it often shows up for me in doing advanced research.
Like one thing that drives me crazy, I hope is this is not too ego—or if it’s like you meet—I meet somebody who’s seeking my time and attention. Like it’s a little bit imbalanced…and they haven’t read The Startup of You, read sorts of things I’ve written. And ask a whole set of questions that I have or collaboratively written about in many different venues.
And it drives me crazy. I’m kind of like—and I try to walk the walk on this myself, but if I’m seeking to build a relationship with somebody who I don’t already know—to really voraciously consume whatever they have published already to show up to that interaction prepared.
And so I think hustle can manifest as being great at information management and information-seeking as it relates to building relationships.
Let’s now close. We’re talking about the third strategy of hustle.
So we’ve talked about not taking no for an answer, not accepting rejection. We’ve talked about tweaking the approach. Sometimes it’s subtle reframe of how you present yourself that can open doors.
The strategy we talk a lot about in the book—in fact, we have a whole chapter on it, Reid—is cultivating strategic serendipity.
There’s a lot of randomness in this world. A lot of things that—you know, especially in an entrepreneurial life, we don’t know exactly what’s gonna happen. We’re gonna try a lot of things. we’re gonna be hustling, we’re gonna be building our network, and we’re gonna have to be excited about all of the uncertainty that might emerge from that, including the positive uncertainty, the positive randomness that could emerge.
And I think, you know, serendipity and hustle are related concepts—distinct, but related. I think one of the things that people who are great at generating serendipity have is sort of this relentless curiosity, right? They don’t always have an end in mind.
They’re kind of like, “This is an interesting person to talk to. I’m not sure exactly where this is going to lead.” Or, “This event sounds interesting. I’ll try it one time. See what happens. I don’t necessarily have a goal.”
But they’re very proactive about putting themselves in unfamiliar places, meeting unfamiliar people. And I feel like, you know, Reid, you’re a great example of this.
For so many years—for as long as I’ve known you—you’ve always had an openness to meeting new people, going to new sorts of things, talking to new sorts of companies.
I feel like for a lot of people, as they achieve, you know, astounding levels of success, they can become quite insular. And like, “I know all the important people already, like, I—it’s enough to keep up with all the people I already know.” And they sort of really turn off that spigot of serendipity, but you’ve seemed to have been very intentional about keeping it open even after all these years.
Reid Hoffman:
Well, I think there’s lots of reasons. One is: you should be an infinite learner. You should always be wanting to learn new things. And if you think you and the amazing people you already know know everything you need to know, it’s huge foolishness.
And so when you look at, you know, anything from, you know, Barry Diller and Brian Grazer to a whole stack of other people—Reid Hastings, and so forth—they are infinite learners, they’re always looking to learn. They’re always, you know, kind of asking questions, kind of figuring out things—how to ask really good questions is a smart part of this. And so you always want to have some of that, you know, kind of serendipity on it.
Now you may say, “Look, I’m really busy. I have lower—the bar gets higher.” You’re not looking for a bar of certainty, like if you’re not having an occasional meeting where you go, “Well, that was pretty useless,” you’re probably not being interestingly diverse and risky enough.
Ben Casnocha:
Or it’s a thing you told me—and I’ve written about this in my essay, “10000 Hours with Reid Hoffman”—but, if you’re not making a mistake, at least 20%, 30% of the time…if you don’t have foot faults 20%, 30% of the time, you’re not moving fast enough in your decision.
Reid Hoffman:
Yes.
Ben Casnocha:
Like, you don’t want 100% percent perfect decision-making out of somebody, right? Because that requires a slowness of speed that’s more broadly problematic.
Reid Hoffman:
Yes, exactly.
And so—now, and, and part of it, you’ve expressed in the right nuance, which is look: foot faults, minor errors. Great. Who cares?
Ben Casnocha:
Yes.
Reid Hoffman:
Major errors. Be a little bit more careful on, ‘cause they can be landmines. They can be much more expensive. And look, sometimes you run into major errors. You miscalculated. It was an important, big risk.
But, still, as an emphasis on speed, if you’re not embarrassed by your first product release, you’ve released too late. That’s an emphasis on speed and learning. It’s not an emphasis on embarrassment. It’s on prioritizing speed and learning, and not prioritizing a lack of embarrassment.
Ben Casnocha:
If you’re waiting until you’re certain that you’re making the right decision, you’re making the decision too late.
Reid Hoffman:
Exactly. Right.
And so this all plays into the question of: how do you hustle forward, and how do you play, because there are great entrepreneurs who think the only advantage of startups is speed.
If you’re not prioritizing on some speed of learning, some speed of decision-making, some speed of execution—by the way, speed doesn’t just apply to execution, applies to decision-making as well—if you’re not prioritizing that, then you’re almost certainly underdelivering how fast you could be learning, how you could be capitalizing, how you could be moving on strategic serendipity.
Ben Casnocha:
And I think the thing with serendipity that’s important is: serendipity starts with saying yes to things. And there’s this kind of interesting meme, I feel like, in the productivity and success literature today, which is like: really successful people know how to say no.
“Gotta say no, that’s how you manage your calendar. Say no, say no, say no. Focus, focus, focus.”
Philosophy of serendipity cuts against some of those principles a bit. It’s kinda like—actually, you’re not quite sure if this is gonna be a good use of time, but you say yes anyway.
I think we can lose sight of that in this sort of modern productivity age, and especially as people become successful, and they become managed, and they become managed in a way where it’s like you have these four priorities. Is this one of your four priorities? Doesn’t make sense for you to do, right?
Generally speaking, I think that’s a good way of being productive in the world. But, I would argue you should have always some openness to serendipity. And at certain times of your life—again, we talk a lot in the book about seasons of life; different seasons of life call for different strategies—if you’re at a career transition, or you’re thinking about a career transition, turn up that spigot. Say yes to more conferences, events, gatherings. Say yes to sort of random outbound or inbound that you might get.
And then the last thing I think on serendipity that’s important to remember is how—as with all these concepts—how to engage with your network. And, so, one of the things I like to think about sometimes is, you know, how can you add intentionality to serendipity?
So, I’m a huge fan of like—if you’re in a career transition or thinking about a new job, or frankly doing, trying to find someone to date, you know have sort of a vague goal that doesn’t have a specific deadline…share that intention out with your network.
Like, I like when I’ve gotten emails from friends, or and I respect it when someone says, “Hey, you know, I’ve been at the NFL for seven years. I’m thinking about a transition. No specific urgency, but just take—keep your ears and eyes open. If there’s something that’s interesting, let me know.”
That to me is kind of like, lightly trying to engender serendipity. It increases the odds that if I bump into somebody that might be relevant to that person, maybe I’ll remember them, and you’re kind of staying top of mind with your network to increase the odds of serendipity out of those first, second, and third-degree connections.
Reid Hoffman:
Yep. And I think part of the thing is—on serendipity—like it’s not the same thing as just saying totally random.
Like, it’s not like, “Well, just ask the person that you happen to be standing next to in a Starbucks line, ‘Let’s go have coffee or something.”’ Like it’s serendipity of unknown, but it’s with a possibility of something like a better-than-average possibility of something really interesting.
That’s why a reference from a friend; that’s why possibly at a conference that fits with your particular interest—I was saying tech conference ‘cause of the Chris Sacca story—like other kinds of things is like—
But to do that is actually in fact really, really good. And as you know, one of places where I still do strategic serendipity—matter of fact, you and I at the relaunch of The Startup of You had an intellectuals dinner. And I was like, “Oh, this would be a great opportunity to meet some other great American public intellectuals we both have a strong interest in. Let’s go do that.” And so we invited some people who we, you know, hope will become new friends and did that as part of it.
And that’s serendipity.
Ben Casnocha:
Fantastic conversation. Just to capture a few of the action items from our talk.
We’re talking about the art of the hustle. And so that first strategy we talked about of: don’t accept rejection; try to learn from it, but stick with it, power through. That’s an essential life skill.
We talked about tweaking your approach. So sometimes just slightly reframing how you’re doing things can lead to a different sort of outcome, and as I think people who are great at hustle have that kind of creative instinct to break through the noise.
And then finally cultivating strategic serendipity. And so, you know, encourage folks to think about a couple things.
One is: is there some serendipity you wanna introduce in your life in the next, you know, next week, next month, next year? Is there a conference that you’ve been thinking about going to that doesn’t seem perfectly relevant? Maybe it’s worth signing up for. Maybe there’s somebody in your network. Maybe it’s a secondary reconnection. They don’t precisely work in your industry, but it’s kind of adjacent. Maybe that person can introduce some new ideas. So just inventory a little bit of those opportunities.
And then also as an action item, think about instances where you’ve felt rejected. Maybe you’ve written an email to someone, they didn’t reply, and you assume that was rejection, and in fact, you just got lost in the email black hole.
Have you yourself declared failure at certain things when in fact some thoughtful and graceful follow-up could turn that no answer into a yes or even a “no” into a yes?
So maybe take a moment, take a few minutes, and think about those instances, and see if you can try again. And if you do that, you are truly embodying The Startup of You philosophy.
Reid, thanks for the conversation, and listeners, thank you for listening.