The most challenging startup problems are often people problems, not technical ones. When co-founder relationships break down, the tendency to blame the other person is strong:

"The weirdest thing that sometimes with co-founders happens is if it doesn't go well then it couldn't be me, it's got to be this other person. It takes two, that's the reality."

Even successful companies can suddenly face existential crises when founders hit breaking points:

"You can even be running a successful company and wake up one day and be like 'Holy shit. I hate my life, I hate my job, I don't want to do this anymore.'"

These intense relationships create the deepest wounds, but if you're experiencing this, you're not alone—it's actually very normal in the startup journey.

Most founders, especially technical ones, naturally gravitate toward product development, coding, and technology rather than the "emotional stuff." As Garry admits:

"When I was starting my company, this is an episode that I would not have listened to because I was like 'ah stupid, like emotional crap, I just want to like write code and learn about technology.'"

Yet ironically, it's precisely these human elements that end up determining success:

"If someone had forced me to sit down and listen to an episode like this and really think about this kind of stuff, that would have been the number one most helpful thing in my startup because actually the thing that held us back were all people problems."

A company is fundamentally people making countless decisions—"tens of thousands over the course of a year"—and these decisions compound. The trillion-dollar tech companies we admire are built on "the compounded decisions of co-founders and executives," making the human element the critical foundation.

In 2007, Harj (then 21) was matched by Paul Graham with Patrick Collison (then 18) in what he calls a "shotgun marriage" of co-founders. After being funded as YC's first international team with his cousin, Harj needed development help for their eBay tools startup.

"Paul Graham introduced us to this guy called Patrick... Patrick applied with this idea for 'eBay meets Wikipedia'... PG was like 'oh, you guys have this idea, you both want to kill eBay... why don't you meet up and see if you want to work together?'"

They spent a weekend together in London and decided to join forces. Despite getting along well personally, the company was acquihired within a year—primarily because none of them were truly passionate about the problem they were solving.

The key lesson Harj learned: "Patrick wasn't suited to a sort of CTO role. As is very obvious now, he's an extreme outlier founder and probably one of the greatest CEOs of our generation."

This mismatch of roles and natural abilities became evident in hindsight, teaching Harj that putting extraordinary talent in the wrong role doesn't work—even with good personal chemistry.

Garry's experience at Posterous revealed the dangers of misunderstanding what a "great founder relationship" actually means. He initially thought it meant maintaining harmony at all costs:

"I thought it meant getting along with each other and maintaining concordance... if I believe X but that other person believes Y, well I could change what I think and let's go with what they say."

This approach led him to repeatedly abandon his own instincts and vision:

"That's not a good relationship, that's lying down... that is literally self-abandonment."

To compensate, Garry tried to be the "hero coder," working 20-hour days on modafinil, while avoiding necessary conflicts over product direction. When users flatlined and his co-founder wanted to pivot to something like "Google Groups," Garry went along despite deep disagreement.

The consequences were severe: "My body keeps the score... I actually had a psychosomatic thing that happened where I couldn't sleep, I couldn't eat, and I couldn't even bring myself to go to the office."

Though Posterous eventually sold to Twitter for $20 million, Garry believes with proper communication and standing his ground, they could have achieved "10 times or 100 times" that outcome.

• Founder conflicts are inevitable - Even the best startups face co-founder tension
• Role alignment is critical - Putting extraordinary talent in the wrong role can doom a company
• Self-abandonment has costs - Sacrificing your vision for harmony leads to burnout
• Physical symptoms signal problems - Your body will tell you when you're suppressing important conflicts
• Cultural and personal backgrounds matter - Your communication style is shaped by your "10,000 hours of human intelligence training called childhood"
• Speaking up early prevents explosions - "See something and say something at the moment it happens instead of allowing it to build up"
• Personality-role fit determines success - Some people need control to thrive, and that's what being CEO requires

Books

• The Body Keeps the Score - Referenced by Garry when discussing how unresolved conflict manifests physically

Companies

• Stripe - Founded by Patrick Collison after his early co-founder experience with Harj
• Posterous - Garry's startup that was eventually acquired by Twitter for $20 million
• Weebly - Mentioned as a company that monetized effectively and sold to Square for "at least 10x" what Posterous did
• Y Combinator (YC) - The accelerator that matched Harj and Patrick as co-founders

People

• Patrick Collison - Co-founder with Harj before founding Stripe
• Paul Graham (PG) - Y Combinator founder who made the co-founder match

Finding the right leadership approach is crucial for founders. As Garry explains, there's a spectrum between harmful extremes:

On one end is self-abandonment - suppressing your opinions to maintain harmony:

"You're getting paid the big bucks, you have equity... you are there to render an opinion and your feelings matter and count. So self-abandonment kind of obviously is bad."

On the other end is being authoritarian:

"That's not listening to anyone ever, jumping to conclusions... skipping ahead to the end result because 'I can't hold this conflict, this is too uncomfortable.'"

The healthier middle ground is being authoritative - creating space for meaningful debate:

"The much better version is actually have a debate. It's good to have healthy conflict where people say what's going on."

Garry reflects that even without being CEO, he could have had better outcomes at Posterous through proper communication:

"We could have had that conversation, we could have made that choice together, and because I burnt out, because I couldn't show up to work anymore, I short-circuited it."

True leadership means sitting down with people you trust, acknowledging uncertainty, having good-faith arguments, and coming to agreements together.

The intensity of startup life often forces founders to confront patterns they never noticed about themselves before:

"A lot of the journey with a co-founder is so intense because you're going through the high pressure of both of you really wanting to see this company succeed. You're pulling insane hours, you may not be sleeping... and you're also going through all these very intense decisions."

This pressure cooker environment reveals deeply ingrained behaviors:

"Maybe up to that point I didn't have the need to self-examine too much... I realized patterns about myself that I didn't know."

Diana shares how her immigrant background shaped her conflict style:

"The safe thing is not to speak up and just not rock the boat, keep things stable... there were things that I would not agree with but I would just not voice them because it was not safe from what I was trained on from my upbringing."

Despite the pain, this self-discovery is "a bit of a gift" - a journey toward becoming a better version of yourself:

"Maybe up to this point before the startup I was successful, I got by enough with how I operated in this world, but this new level of intensity... I needed to gain more control or power over myself and gain more of these skills that are new."

One of the most important realizations for struggling founders is that they're not alone:

"Don't feel alone if you're going through this. It's actually very normal. I mean, this is why I think YC was special for me too. I could talk to other YC founders like 'oh I'm not crazy.'"

Even when conflicts feel existential in the moment, they often seem trivial in retrospect:

"In retrospect, I don't think they matter that much. It's kind of the irony... it would have been fine, but they felt so life and death back then."

The real challenge is separating your ego and identity from the startup:

"Any given moment you have your ego, you have yourself, you have your concept of yourself, and then all of that is wrapped up into your identity which then merges with the startup."

This leads to the common trap: "If it doesn't go well then it couldn't be me, it's got to be this other person." But the reality is that "it takes two."

Many founders, especially younger ones, lack effective conflict resolution skills when starting companies.

Jared shares an embarrassing but instructive example:

"Our company was called Scripted, and Scripted is a terrible name for a startup. No one can pronounce it, no one can spell it... and the reason we ended up with this horrible name is that we could not agree on what to call the company."

"We literally fought about it the entire YC batch. We probably spent tens of hours debating what to call the company. It got so bad we had to call in Paul Graham to mediate a dispute because we were unable to launch because we could not agree on what to call the thing we were about to launch."

Looking back, Jared recognizes how wasteful this was:

"Of course like it doesn't matter and all that debate only led to a bad outcome anyway."

This pattern is common: "A lot of the college age founders that we fund... just had not developed good conflict resolution skills."

The founders discuss practical frameworks for healthier communication:

1. Non-Violent Communication (NVC) - This approach emphasizes observations rather than judgments: "You are totally free to talk about what's going on over here, but if Harj and I are fighting, it's not fair for me to speculate or say anything about his intentions or his motivations."

2. Focus on observable behaviors, not character judgments: "What's observable is the behavior, what people do, and how you feel, and those are okay things to call out."

   Instead of saying "you're a bad engineer" (demotivating), try: "I saw you checked in this code and it didn't do the QA test and other unit tests as we had agreed. This is something that we can improve on."

3. Show the benefit of change: "The other thing is giving them a carrot - if you do it and change it, this is how it's good for everyone."

This approach makes feedback actionable rather than personal:

"It's nothing about me fundamentally as a person or as an engineer, it's just a thing that I did... but let's just get the output to be fixed."

• Leadership requires balance - There's a middle ground between self-abandonment and authoritarianism
• Startup pressure reveals hidden patterns - The intensity forces self-discovery about your communication style
• Cultural backgrounds shape conflict styles - Your upbringing creates "default settings" in how you handle disagreement
• Co-founder conflicts feel bigger than they are - What seems life-or-death now may seem trivial in retrospect
• Focus on behaviors, not character - Effective feedback addresses specific actions, not the person
• Show the benefits of change - Frame feedback to demonstrate how improvements help everyone
• Identity merging with startup creates problems - When you can't separate yourself from the company, it's harder to receive feedback

Books

• Non-Violent Communication (NVC) - Recommended by Garry as a framework for better conflict resolution

Companies

• Scripted - Jared's startup that suffered from poor conflict resolution between co-founders
• Y Combinator (YC) - Mentioned as a supportive community where founders could realize their conflicts were normal

Concepts

• Touchy-Feely class from Stanford - A course referenced that teaches communication skills

A powerful framework for healthy communication comes from Stanford's "Touchy-Feely" class - the concept of staying on your side of the "net":

"In any communication there's like your reality, the way you're experiencing it and all the assumptions you're making about what's going on, and then there's the other side's."

The key principle is:

• You can freely discuss everything on your side of the net: your feelings, experiences, and reactions
• You shouldn't cross "over the net" by making assumptions about the other person's intentions or thoughts

"It's totally fine for me to talk about everything on my side of the net... how I'm feeling... how it feels when you say I'm not a good vibe coder. But I can't go over the net which is like 'you're a bad engineer' or try and tell the other person what they're feeling or what they're thinking."

This mistake is a "natural human tendency" - assuming negative intentions behind another's actions:

"You assume that if Garry says I'm a bad vibe coder, it's because he wants to hurt me and he's mad at me... but I don't know what's going on in his head actually, and the only way I can understand it is to ask him directly versus making lots of assumptions."

This principle applies broadly: "That's the concept over the net, which is overall good communication with anyone, not just for managing co-founders—significant others, friendships—just to be overall a better human."

The danger of close working relationships is that individual conflicts can blend together and become personal:

"You can easily get into this moment where it's very one-on-one adversarial. The bad version of this just sort of becomes like tit-for-tat—all of the arguments sort of bleed over."

When this happens, decisions are no longer about the work but about winning:

"Whether or not this button is red or blue... if you view that conflict in the context of all the other conflicts you've had that week, month, or in your entire life, there's bleed-over."

"It's not really about whether it's red or blue, it's about who wins and 'is there a point system?' Like, 'well, last time you won, so this time'... and at that point, hey, what about the mission? What about the thing that we're out here to do, which is get users and make something people want?"

When conflicts reach this point, it may be time to bring in outside help like an executive coach to break this destructive pattern.

Both personal background and work experience shape how founders approach conflict, which can create fundamental mismatches in communication styles:

Harj shares how his second startup exposed this challenge. His co-founders came from Justin.tv (which later became Twitch), a company "notorious for having an early culture of extreme aggressive heated debates":

"My two co-founders, this was their first job out of college, and so they kind of just thought that was how startups work—that people are just screaming and shouting at each other all the time."

This created a fundamental mismatch, as Harj explains:

"If you grow up with this one type of culture where outright extreme aggressive debate is the way you get to the truth and win, it's not the culture that I can really work particularly well in."

"If I'm in an environment where people are shouting and screaming, I kind of just can't really think clearly. To me, shouting and overly heated debate just means you can't think clearly about stuff, and so you're just going to make bad decisions."

When founders have these different perspectives—one believing aggressive debate leads to bad decisions while the other believes it's "the only way you can make good decisions"—it creates a constant source of conflict.

When faced with different communication styles, many founders try to adapt rather than establish boundaries. Harj describes this mistake from his own experience:

"My way of handling it was 'I should adapt'... In general, a lot of my desire to do a startup was personal growth and wanting to get better. I was like, 'Okay, well, it probably would be helpful for me if I can just get better at handling more aggressive debate, so I will mold myself into being able to do that.'"

While this adaptation initially seemed like personal growth, it eventually became unsustainable:

"Four or five years into the startup, it was actually just a huge tax on me personally, and part of the reason I kind of burned out and decided I wanted to move on and hand over the CEO reins was like—I'm just exhausted. Actually, for me, being in this culture and trying to always bring it back to the middle or turn the temperature down was just exhausting."

His key advice in retrospect: "I wouldn't have adapted." Instead of conforming to a culture that doesn't work for you, founders should shape the company culture to get the best out of themselves.

Many founders fall into what Harj calls "the servant leadership model"—the belief that "you have to sacrifice yourself for the greater good, which is the org, and so you have to mold yourself into what the org needs."

But there are limits to this self-sacrifice. Trying to operate in a way that fundamentally conflicts with your natural style eventually leads to burnout:

"You can like even be running a successful company and wake up one day and be like 'Holy shit. I hate my life, I hate my job, I don't want to do this anymore.'"

This pattern extends beyond co-founder relationships to the entire organization:

"If you're a public company and you hire a bunch of execs and the execs all have totally different ways and they become the dominant frame, then you're like basically in the same spot where you're trapped. You're the founder but you feel trapped."

The solution involves recognizing your own needs:

"You have to stop adapting yourself at some point and make the org adapt to you to get the best out of you."

• Stick to your side of the net - Speak about your experience without assuming others' intentions
• Watch for "everything conflicts" - When arguments blend together, you're no longer making decisions on merit
• Work cultures shape communication styles - Previous company experiences create expectations about "normal" conflict
• Adaptation has limits - Trying to operate in a way that conflicts with your natural style leads to burnout
• Shape culture for your strengths - As a founder, create an environment where you can do your best work
• Know when to get outside help - Executive coaches can break destructive communication patterns
• Test relationships under stress - Social friendships don't always translate to effective work partnerships

Companies

• Justin.tv - Later became Twitch, mentioned for its culture of "extreme aggressive heated debates"
• Triple Bite - Harj's second startup where he experienced communication style conflicts

Concepts

• "Over the Net" - Communication concept from Stanford's "Touchy-Feely" class about not making assumptions about others' intentions
• Servant Leadership Model - Leadership approach where leaders prioritize serving others, which can sometimes lead to unhealthy self-sacrifice

As founders navigate the challenging interpersonal dynamics of startups, outside support becomes crucial:

"I think founder teams should really get a lot of help outside of the company as well. I do think founders should probably get, at some point, like a coach, a therapist, to examine a lot of these things."

These issues often develop beneath the surface:

"A lot of these are kind of brewing in the background and you don't even know how to articulate it, how to put it into words, what framework to use to even know that you're going through this transition."

An external perspective provides essential clarity:

"You kind of need this outside partner to hold a mirror for you to know that, 'Hey Harj, you're going through this. It was fine to mold yourself, the company got to this point, but you've got to make room for yourself to be able to live in it for the long run.'"

The founders agree that therapy accelerated their self-awareness:

"Therapy definitely helped me introspect on a lot of this stuff. If I had started therapy sooner, I would have probably stopped adapting myself much sooner."

Many founders resist this help due to misconceptions about their own stability:

"I started the company and I'm like, 'I'm normal, I'm fine, I'm just like everyone else, I have no problems.' And it turns out like that was not correct."

Despite the difficulties discussed throughout the episode, the hosts firmly believe in the value of co-founders:

Garry suggests that co-founding is a natural result of excellence:

"Only the truly superlative founders end up making products and services that are superlative. Like it or not, in order to create something of great value... game recognizes game."

"When someone is truly recognizably good as an engineer or as a designer or as a product person or as a CEO or salesperson... it gets easier to find a co-founder because other people are like, 'That's the person who is the best person I've ever worked with.'"

He compares starting a company to "getting into a rowboat" to search for "the island of gold," asking:

"Do you want the other people in that rowboat to be the most capable people who are super fierce and never say no, or do you want them to be okay?"

If someone struggles to find a co-founder, it might be a signal:

"If someone's having a really hard time finding a co-founder, the advice might actually be: you're not at the edge of human capability yet... find a way to get there because then you will find the other people who are rolling in that direction."

The team agrees that while "a bad co-founder is definitely worse than being solo," the greatest potential comes from partnership:

"The best possible world is having someone who is alongside you, who mega gets you, and when you're having the worst day—and everyone does—ideally your co-founder is there to just pull you up. You can go way farther for way longer and create way more awesome things with people who are your people."

Given how rare successful startups are, "you kind of need every possible advantage you can get." Going solo is "a limiting downside type optimization"—not the right approach for maximizing potential.

The hosts conclude with a philosophical perspective on the inevitability of people problems:

"If you don't want to have people problems, then you need to live on an island totally alone with no one."

Citing philosopher René Adler: "All problems are actually people problems and interpersonal problems... if you want to have no problems, then go live alone on an island."

But this isolation comes at a tremendous cost:

"If you actually want to live any form of fulfilling life, you need to be part of a society and a group of people, and you have to work through the problems and get good at dealing with them and get good at handling conflict."

Rather than seeing these challenges as obstacles to overcome before reaching success, they're actually the essence of the journey:

"A lot of people in modern society run around and they're just trying to get to the end... that's sort of like going to a symphony and instead of the concert playing out, they just play the crescendo at the end, and then that's it. But no, the journey is actually the fun part."

The metaphor comes full circle to the "over the net" concept discussed earlier:

"You can't learn to play tennis and not go over the net if you have no one on the other side of the net."

Whether with co-founders or other relationships, these interpersonal challenges are "one game that is actually worth playing."

• External perspective is crucial - Coaches and therapists help founders see patterns they can't recognize alone
• Excellence attracts excellence - The best founders naturally find each other through mutual recognition of capability
• Bad co-founders are worse than solo - But great co-founders enable achievements impossible on your own
• Startup success requires maximum leverage - Going solo limits your potential upside
• People problems are unavoidable - The only way to avoid interpersonal challenges is complete isolation
• The journey is the destination - The process of working through challenges is what creates meaning and growth
• Finding support earlier accelerates growth - Many founders wish they'd sought therapy or coaching sooner

Books/Concepts

• René Adler's philosophy - The idea that all problems are ultimately people problems
• Alan Watts - Philosopher referenced regarding people rushing to the end rather than experiencing the journey

Organizations

• YC Summer Fellows Grants - Mentioned in the outro, offering $20,000 cash grants and $90,000 in compute credits for college students to work on technical projects