Jun 30, 2022 · 1h 4m · startup-ideas
How To Create Your Own Luck With Julien Smith
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Entrepreneur and author Julien Smith joins the hosts to discuss overcoming working-class underdog roots, building resilience through startup adversity, scaling ventures like Breather and Practice, and using disciplined daily habits to manufacture luck.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 47.3% of the talking time here. How this is scored →
Greg as informed peer 4.5 Guest teaching 5.1 Guest disagreement 1.3 Greg pushing back 1.0
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:15 Julien addresses the uncredited adoption of his blog title into a best-seller
Julien pushes back against tech industry bitterness while candidly noting his original 2011 viral SEO dominance before others capitalized on the concept as a published book.
Hardest push from Greg ▶ 43:51 Greg gently challenges Julien's founder-only friend circlesGreg offers a counter-perspective to Julien's claim that friends must be entrepreneurs by sharing how reconnecting with elementary school non-tech peers provides him greater grounding.
Biggest teaching moment ▶ 50:03 Julien deconstructs Rockefeller and the myth of the virtuous titanJulien delivers a thoughtful historical breakdown showing how massive industrialists like Rockefeller stabilized economies while terrorizing those around them, urging listeners not to conflate competence with morality.
Greg holds their own ▶ 31:00 Greg recounts the brutal reality of encountering a 10x competitorGreg demonstrates deep firsthand startup experience by sharing a vivid story of having a competitor show him a vastly superior product, validating the brutal emotional toll of early entrepreneurship.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Working-Class Origins, Affiliate Marketing, and Generating Luck | 6 | 5 | 1 | 1 | The conversation begins in a highly collaborative manner as Julien explains his working-class background and early internet hustles. Greg contributes to the discussion by introducing Naval Ravikant's mental model of generating luck through high-velocity motion. | |
| Learning from Failure, Near-Drowning, and Radical Fearlessness | 5 | 6 | 2 | 1 | Julien discusses how early traumatic failures can damage founder fearlessness, referencing a near-drowning surfing experience. Greg adds an analogy about boxers compounding learning from glancing blows rather than getting knocked out. | |
| Geographic Mindsets, Developing Thick Skin, and Facing Imposter Fears | 5 | 6 | 2 | 1 | Greg shares insights on how growing up outside major tech hubs like Montreal lowers the financial cost of failure, while Julien elaborates on how lack of local support forces founders to become galvanized against rejection. Greg then shares a personal story of overcoming public imposter syndrome. | |
| Managing Founder Anxiety and the 'Complete Guide to Not Giving a Fuck' | 4 | 6 | 2 | 1 | Julien discusses moving away from performative optimism to authentic vulnerability as a second-time founder. Greg prompts Julien to reveal the origins of his viral 2011 post 'The Complete Guide to Not Giving a Fuck' predating Mark Manson's best-selling book. | |
| Enduring Entrepreneurial Suffering and Daily Process Focus | 6 | 5 | 1 | 1 | Julien and Greg reflect on the mental discipline of day-to-day focus during dark entrepreneurial phases. Greg recounts a painful early founder experience in 2011 when a competitor built a platform ten times better than his own. | |
| Mid-Roll Sponsor Break: Fundrise and Lemon.io | 0 | 0 | 0 | 0 | Mid-roll advertisement break featuring promotional reads for Fundrise and Lemon.io with no conversational dialogue. | |
| Taking Action on Secret Projects and Raising Over $200M for Breather | 5 | 5 | 1 | 1 | Julien details his method of daily habit tracking to build momentum on secret projects and securing his first angel check from Gary Vaynerchuk. Greg highlights Julien's trajectory raising over 200 million dollars despite entering venture capital as an outsider. | |
| Maintaining Grounding Relationships and Childhood Communities | 5 | 5 | 1 | 2 | Greg gently contrasts Julien's view on founder friends by emphasizing how re-engaging with childhood friends keeps him grounded. Julien agrees, explaining how his lifelong Dungeons & Dragons group keeps his ego in check because they do not care about his tech accomplishments. | |
| Separating Outsized Achievement from Moral Idolatry | 4 | 7 | 2 | 1 | Julien gives a detailed historical case study of John D. Rockefeller and modern venture figures like Peter Thiel, arguing that society must separate massive business accomplishments from moral idolization. The host listens attentively and agrees with the psychological necessity of this separation. | |
| Building Practice, Matisse Mastery, and the Red Thread of Empowerment | 5 | 6 | 1 | 1 | Julien outlines his operating mindset for his current startup Practice, comparing iterative mastery to Matisse rather than a singular young genius like Picasso. Greg synthesizes the discussion, praising the 'red thread' of individual empowerment and daily process focus. |
Statements from this episode (15)
Julien Smith made millions online in his twenties doing 'nothing'
“Previous to our generation, you couldn't have like some 20 year old kid that's like, yeah, I made a couple million dollars on online, kind of doing nothing. And then I went on and did some other thing, but I was one of those people.”
Smith: Building outside tech hubs lowers costs but requires immense resilience
“The city itself is not telling you something, but the ethos of that city is saying things to you. And where we come from, the city is just like, yeah, hang out. Like everything's cool. You're going to be all right. You don't need to work that hard. And so it m…”
Smith: I was among the first 10,000 users on Twitter in 2006
“I remember being in the first 10,000 users in Twitter in 2006”
Smith: Acknowledging startup challenges builds credibility and prevents founder anxiety
“Now what I do is, is I say, here's the things that are going well, here's the things we need to work on. And I think that, that, that, that understanding that there's still something to work on. First of all, it gives an impression to me that Of me that people…”
Smith's blog post on 'not giving a f*ck' drew 10,000 daily visits
“And so when I wrote this piece, all of a sudden I ranked number one for years for how to not give a fuck for years. And so, 10,000 visits a day or some shit would go to my website for this idea of not giving a fuck, right?”
Greg Isenberg invested all his money into video startup FiBuy in 2011
“I remember, 2011, 2012, coming from Montreal to San Francisco, put all my money into this video discovery startup I was running called FiBuy, and I was literally, like, reaching out to anyone who would talk to me.”
Isenberg: Entrepreneurial suffering is inevitable, but becomes easier over time
“Ever since then, like every, you know, big suffering event has been like less and less and less. But if you're going to sign up to entrepreneurship, you are going to suffer period.”
Julien Smith raised about $200 million for his startup Breather
“About two hundred million dollars.”
Gary Vaynerchuk was the first angel investor in Breather
“I take the call from Gary, and he goes something like, I don't have time to advise, because I was just like, I was like, well, he even, like, does he really know me that well? Is he, and he's like, yeah, Julian has been around a super long time. Yeah, I'll def…”
Julien Smith: Non-founders cannot truly understand an entrepreneur's experience
“Increasingly it's like you have your friends kind of have to be entrepreneurs. It's not like universally true, but they just like get you in a way that other people do not. And there is this mutual understanding. And again, like I'm making these weird analogie…”
Greg Isenberg shifted his social time from entrepreneurs to childhood friends
“I've actually over the last, since COVID basically have been spending way more of my time with the people I grew up with who are not entrepreneurs and increasingly spending more and more of my time with those people and less and less time with entrepreneurs an…”
Julien Smith: Non-tech friends prevent founders tying self-worth to startup performance
“These early longstanding friends of mine that I've had a really long time and that probably are the people that keep me grounded because otherwise my identity would have been too attached to, I run a startup. Oh My God. I'm, you know, like I'm the second comin…”
Julien Smith: Stop idolizing hyper-successful founders as moral paragons
“And so I think if we like, we separate completely, and I know it's different, very difficult to do that. We separate the acts of success and the things that they have built completely from the person. That way we can be like, that's super cool that you built P…”
Julien Smith: Founders only get about five shots to build something major
“One of the things you realize when you start a company Is you kind of only have a shot, a couple of shots, if it's going to work well. And if you, it is going to work well, like you've had, for example, Alexis O'Hanian on this show, it's like, you don't have l…”
Julien Smith: Only start businesses around your lifelong personal themes
“What are the things that I cared about today at my age, but that when I was 20, I still cared about. So those are the through lines. And I went through them and there's not a lot of them. And I said, those are the things, probably the only things that I can st…”