A16z Horowitz Warns Founder Mode Deference Risks Startup Failures

Ben Horowitz On What Makes a Great Founder — Sequoia Capital

Sequoia Capital

First-time CEOs paralyze organizations with decision debt because they lack the confidence to manage experienced executives through constructive confrontation.

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## Background Published on YouTube by Sequoia Capital on February 26, 2026, this page features an unfiltered conversation with a16z co-founder Ben Horowitz about what breaks founder CEOs and what sets the great ones apart. The description highlights deep dives into 'founder mode,' the danger of avoiding hard truths, constructive confrontation, executive hiring pitfalls, and the psychological realities of navigating hypergrowth.

## TL;DR In this wide-ranging conversation, Ben Horowitz and host Brian Halligan explore the essential traits of successful tech leaders, emphasizing the necessity of raw intelligence, original thinking, and productive paranoia. Horowitz critiques the traditional COO role in early-stage startups and warns against the traps of executive over-deference and decision debt that frequently paralyze first-time CEOs. He breaks down the rigorous discipline required for complex sales hiring, outlines how true corporate culture is defined by behaviors rather than empty values, and contextualizes the recent rise of 'founder mode' leadership. Ultimately, the discussion normalizes the deep discomfort and uncertainty inherent in scaling a hypergrowth enterprise.

## Atmosphere & style The dialogue carries a raw, authoritative, and deeply pragmatic tone, stripping away typical corporate politeness to favor blunt, high-stakes business realities. Moving from intense personal anecdotes of venture capital rejections to the legendary, high-friction communication styles of Silicon Valley giants, the narrative feels like a masterclass in operational survival. Listeners experience a compelling emotional arc that transitions from the intimidating pressures of early-stage failures to a reassuring, grounded normalization of the psychological struggles and uncertainty that even the most iconic founders face.

## Key takeaways - [00:00](https://www.youtube.com/watch?v=dFT4xj57D7U&t=0s) The best tech companies are led by founders who practice 'constructive confrontation' and ask blunt questions rather than avoiding hard truths to protect feelings. - [03:01](https://www.youtube.com/watch?v=dFT4xj57D7U&t=181s) Ben Horowitz maintains a skeptical view of the COO role in early-stage startups, arguing that flatter organizations are better and that a COO layer can degrade a tech company's 'communication architecture.' - [03:58](https://www.youtube.com/watch?v=dFT4xj57D7U&t=238s) When evaluating founder CEOs, Horowitz avoids looking for a specific archetype and instead filters for original thinking, leadership capability, and the ability to drive talent density. - [05:41](https://www.youtube.com/watch?v=dFT4xj57D7U&t=341s) The ideal founder profile depends heavily on the market; deep tech or massive platform plays require raw cognitive horsepower, whereas marketing and sales innovations do not rely as strictly on pure math prodigies. - [07:29](https://www.youtube.com/watch?v=dFT4xj57D7U&t=449s) Databricks CEO Ali Ghodsi's success is attributed to his combination of computer science intelligence, strong go-to-market strategy, and a productive paranoia rooted in his background as a refugee. - [08:32](https://www.youtube.com/watch?v=dFT4xj57D7U&t=512s) Fast-growing startups often fail when founders lack confidence, resulting in either over-deferring to smart hires or hesitation and decision paralysis due to a fear of making mistakes. - [11:48](https://www.youtube.com/watch?v=dFT4xj57D7U&t=708s) Engineers often fail at hiring head of sales roles because of a fundamental communication clash: engineers look for single correct answers, while salespeople seek to understand the underlying motive of a question. - [15:47](https://www.youtube.com/watch?v=dFT4xj57D7U&t=947s) A great sales candidate will actively qualify the startup during the interview process by asking tough questions about customers and product viability rather than just showing eager enthusiasm. - [18:30](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1110s) Great sales leaders possess a loyal following of high-performing reps willing to follow them, and they are best forged in environments where they had to succeed with a complicated, hard product sell. - [23:14](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1394s) HubSpot's successful sales hiring process focused on candidates in their second sales job and utilized a strict 30-minute roleplay test specifically designed to measure coachability. - [30:16](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1816s) While Paul Graham's 'founder mode' highlights the danger of overly deferring to executives, founders make a dangerous mistake if they misinterpret it to mean they should avoid hiring senior talent altogether. - [03:12:26](https://www.youtube.com/watch?v=dFT4xj57D7U&t=11546s) The key to managing experienced executives in founder mode is for the founder to learn enough about the specialized roles so they have the confidence to manage them rather than letting executives dictate terms. - [03:16:39](https://www.youtube.com/watch?v=dFT4xj57D7U&t=11799s) Company culture is defined entirely by the actual behaviors of its people and leaders, not by empty, written values or platitudes like integrity. - [03:16:39](https://www.youtube.com/watch?v=dFT4xj57D7U&t=11799s) Vague rules like 'no assholes' do not work with highly talented individuals; instead, leaders must establish very specific behavioral boundaries and consequences. - [03:42:54](https://www.youtube.com/watch?v=dFT4xj57D7U&t=13374s) Venture capital is vastly easier than entrepreneurship because VCs have safety nets, multiple funding sources, and room for luck, whereas entrepreneurs have one shot and pay for mistakes directly under relentless pressure. - [47:08](https://www.youtube.com/watch?v=dFT4xj57D7U&t=2828s) Avoiding difficult organizational decisions creates 'decision debt' and often stems from a lack of confidence or a counterproductive desire to be a popular, conflict-averse CEO. - [48:29](https://www.youtube.com/watch?v=dFT4xj57D7U&t=2909s) Operating with a continuous sense of uncertainty and feeling unqualified is entirely normal and represents the default reality of navigating a hypergrowth company.

## Detailed walkthrough ### [00:00](https://www.youtube.com/watch?v=dFT4xj57D7U&t=0s) The Importance of Bluntness and Speed in Tech Companies

The very best companies in the world tend to have founders and CEOs who ask highly aggressive, blunt questions. Leaders like Mark Zuckerberg and Larry Page, who have reached the absolute pinnacle of the tech industry, do not run away from the truth to preserve people's feelings. In a fast-moving tech company, avoiding hard truths is incredibly dangerous. A critical corollary to this leadership style is ensuring that "bad news travels fast" so that the CEO can find out about problems immediately and address them before they escalate.

[00:51](https://www.youtube.com/watch?v=dFT4xj57D7U&t=51s) Behind the Scenes of a Famous Venture Capital Pass

In this episode, host Brian Halligan sits down with Ben Horowitz, co-founder of the venture capital firm Andreessen Horowitz (a16z) and author of the 2014 management classic *The Hard Thing About Hard Things*. Halligan kicks off the conversation by sharing a personal story from HubSpot's Series D pitch to Andreessen Horowitz. Halligan, along with his co-founder Dharmesh Shah and their newly hired COO JD Sherman, walked into the pitch room feeling highly confident. They had a warm connection in Mark Cranney (a former colleague of Halligan's who worked for Horowitz), and two of the firm's marketers even owned copies of their book, *Inbound Marketing*.

However, the pitch quickly took an intense turn. Horowitz spent the first 15 minutes grilling the newly hired COO, JD Sherman, about his background. He then turned to Halligan and spent another 15 minutes questioning why on earth he had hired a COO in the first place. Andreessen Horowitz ultimately passed on the round—as did every other firm they pitched at the time. Two weeks later, Halligan read Horowitz's book and realized Horowitz was notoriously skeptical of the COO role. Despite the rejection, Halligan notes that Horowitz's aggressive questioning "put a ginormous chip" on JD Sherman's shoulder, which proved incredibly beneficial for HubSpot's execution.

[03:01](https://www.youtube.com/watch?v=dFT4xj57D7U&t=181s) The Problem with the COO Role in Early-Stage Startups

When asked if his views on the Chief Operating Officer (COO) role have changed, Horowitz explains that his stance remains largely the same: when a company is small, "flatter is better." While the "Mr. Outside, Mr. Inside" executive construct was highly popular in the early 2000s, it rarely works long-term in technology companies. A COO layer can function temporarily during a stable product cycle, but once a company hits the end of that cycle and needs to pivot or innovate, the structure breaks down.

Horowitz argues that a tech company's success is deeply tied to its "communication architecture," and inserting a COO often degrades that flow of information by creating a "two people in charge" dynamic. He clarifies that if "COO" is simply a grand title given to a head of sales, that is perfectly fine. The real danger arises when the COO is actually running the day-to-day operations of the company while the founder acts merely as a public-facing figurehead.

[03:58](https://www.youtube.com/watch?v=dFT4xj57D7U&t=238s) What Makes a Great Founder CEO

When evaluating founder CEOs for investment, Horowitz avoids looking for a "canonical" archetype. Leaders like Mark Zuckerberg, Ali Ghodsi, and Elon Musk are radically different in their personalities, communication styles, and levels of introversion or extroversion. Instead, Horowitz filters for a few core traits:

* **Original Thinking:** Great founders think for themselves. They do not try to "read the room" or allow themselves to be easily swayed by what an investor wants to hear. * **The Colin Powell Definition of Leadership:** Horowitz defines leadership as "the ability to get people to follow you if only out of curiosity." A founder must be compelling enough to recruit high-end talent. * **Talent Density:** A company's ultimate success is a momentum game driven by its ability to hire the absolute top tier of talent.

[05:41](https://www.youtube.com/watch?v=dFT4xj57D7U&t=341s) The Debate Over "Math Olympiads" vs. Raw Horsepower

Halligan shares a recent debate from a Sequoia offsite where partner Shawn Maguire argued that venture capitalists should specifically target founders who won chess or math Olympiads in high school and who surround themselves with similar academic champions. While Halligan pointed out that HubSpot succeeded by hiring heavily from Northeastern University and the MIT Sloan School of Management rather than relying on pure math prodigies, Horowitz offers a nuanced middle ground.

Horowitz explains that the ideal founder profile depends heavily on the era and the market. A company like HubSpot was as much a marketing and sales innovation as it was a technological one, meaning math Olympiads would not have been the right fit. However, for deep tech or massive platform plays, raw cognitive horsepower is essential. He notes that while Elon Musk and Larry Page may not have been formal math Olympiads, they possess an extraordinary level of raw intelligence that is absolutely necessary to conceptualize and build companies of Google or Tesla's scale.

[07:29](https://www.youtube.com/watch?v=dFT4xj57D7U&t=449s) Ali Ghodsi and the Power of Founder Paranoia

When asked who the best CEO he currently works with is, Horowitz names Ali Ghodsi, the CEO of Databricks. Ghodsi holds a PhD in computer science, satisfying the high-intelligence criteria, but he also possesses an exceptionally strong grasp of go-to-market strategy, allowing Databricks to compete fiercely against Snowflake's formidable sales machine.

Beyond his intelligence, Ghodsi's defining trait is his extreme, productive paranoia—a trait Horowitz has only otherwise seen in Andy Grove and Elon Musk. This psychological drive stems from Ghodsi's background as a refugee; he grew up in Iran and had to flee to Sweden when the Ayatollah Khomeini came to power. Having everything taken away from him at a young age deeply informed his psychology, making him highly resilient and constantly vigilant as a founder.

[08:32](https://www.youtube.com/watch?v=dFT4xj57D7U&t=512s) The Universal Traps of Scaling: Deference and Hesitation

For fast-growing startups, the most common failure modes stem from a lack of confidence. Because founders have typically never run a company before, they inevitably make damaging mistakes. Feeling terrible about hurting the people they recruited, founders often overcorrect in one of two dangerous ways:

1. **Over-Deference:** Founders stop making decisions independently and instead run the company by "polling" their smart hires. This is disastrous because no one else has the full context of the business, and it creates a power vacuum that invites toxic internal politics. 2. **Hesitation and Avoidance:** Founders become terrified of making a mistake, leading to decision paralysis. They avoid hard actions—like firing an underperforming head of sales—because they worry about what the board, the press, or the team will think.

Horowitz compares a hesitant CEO to an NFL linebacker: "If you were like a linebacker in the NFL and you were really fast, but you didn't trust your eyes, you would get cut." A CEO must trust their eyes, run directly at the problem, and make the decision. Halligan agrees, noting that HubSpot suffered from "decision debt," which paralyzed the company until he forced himself to make hard choices.

[11:48](https://www.youtube.com/watch?v=dFT4xj57D7U&t=708s) The Cultural Clash of Hiring a VP of Sales

Hiring executives is incredibly difficult for founders because they often do not understand the roles they are hiring for. Horowitz compares hiring a CFO when you do not understand corporate finance to trying to hire a Japanese interpreter when you do not speak Japanese—everyone is going to sound pretty good. He advises founders to talk to experienced CEOs to learn what "great" looks like, or even try doing the job themselves temporarily to feel the specific challenges of the role.

This issue is most acute when engineers try to hire a head of sales. The cultural divide between engineers and sales professionals is vast, starting with how they communicate:

* **Engineers** are trained to find the single, objectively correct answer to a question. * **Salespeople** are trained to figure out *why* a question is being asked in the first place to identify underlying competitive traps or customer needs.

Because of this, engineers often reject the best sales candidates because they find their communication style evasive, ending up hiring terrible candidates who simply "passed the engineering test" and put on a clean shirt.

Horowitz recalls a conversation with Sujay Jaswa back when he was at Dropbox, who was struggling with engineers complaining about sales commissions. Horowitz's advice was blunt: tell the engineers that if they want commissions, they can "grab a bag and sell some software," with the understanding that they will be fired if they miss their quota. He points out that while engineers might write code on the weekend for fun, no salesperson sells software as a hobby. Sales is a prize fight, and "there is no fight without a prize."

[15:47](https://www.youtube.com/watch?v=dFT4xj57D7U&t=947s) The High-Stakes Okta Hire

When an engineering-minded CEO is looking to make their first major sales hire, they are highly susceptible to making a catastrophic mistake. Ben Horowitz illustrates this danger with a story from the early days of Okta, a company backed by both Sequoia and Andreessen Horowitz. The co-founder and CEO, Todd McKinnon, was choosing between two candidates for the head of sales position. One was an unnamed candidate who was incredibly enthusiastic about Okta, and the other was Adam Aarons, a veteran of the PTC (Parametric Technology Corporation) sales tree. Todd strongly favored the enthusiastic candidate, but Ben's deep-network reference checks revealed that industry insiders considered that candidate a "B" player, whereas everyone swore by Adam.

Todd's preference for the enthusiastic candidate came down to a classic hiring trap: he liked that the candidate was incredibly excited about the startup, whereas Adam was more reserved, asking to talk to customers and thoroughly vetting the opportunity. Ben had to step in with some blunt, high-pressure advice, explaining that a great salesperson shouldn't just eagerly answer questions; they should actively qualify the customer. Ben warned Todd that if he made the wrong hire, it would mean the end of the company. Todd ultimately hired Adam, a decision that Ben believes saved Okta from going bankrupt and ultimately "ended up really making the company."

- **Key Takeaway:** A great sales candidate will qualify your startup just like they would qualify a prospect, asking hard questions about customers, budget, and product viability. - **The Power of Blind References:** Relying on backchannel references from people who are owed favors is far more reliable than relying on the candidate's self-reported enthusiasm.

[18:30](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1110s) The PTC Mafia and the Power of Followers

For an early-stage CEO, a critical test of a sales leader's caliber is asking a simple question: "Who are you bringing with you?" Any truly great sales leader has a loyal following of high-performing reps who are ready to jump ship and join them. Mediocre leaders, by contrast, bring nobody because sales reps are incredibly savvy about who is worth working for. This dynamic was a defining feature of the famous "PTC mafia" of the 1990s—a legendary sales diaspora from Parametric Technology Corporation that went on to populate and dominate Silicon Valley's executive ranks.

PTC sold CAD/CAM and PLM software to manufacturers, which was an incredibly difficult sell. In fact, the product—particularly Windchill—frequently "didn't work" or was plagued by immense technical challenges. This difficulty was actually a breeding ground for elite sales talent. Ben notes that you should always prefer to hire a sales leader who succeeded with a hard sell rather than someone who put up massive numbers selling an easy, high-demand product.

- **The "Easy Sell" Trap:** Hiring someone who crushed their numbers selling something like Google AdWords is risky because that role is more about order-taking than actual selling. - **The Follower Test:** Always ask a sales candidate for the names of the reps they plan to bring with them, and call those reps to verify if they are actually willing to follow.

[20:25](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1225s) The Discipline of a Complicated Sell

The magic of the PTC sales methodology lay in its rigorous, systematic discipline. When a product is difficult to sell and faces fierce competition, a sales organization cannot afford to skip steps. Reps had to be incredibly methodical about laying traps for competitors, building comprehensive technical and business cases, and mapping out every single stakeholder in a complex corporate decision-making process. This level of competitiveness and discipline translates to any product, whereas reps who sell highly sought-after products—such as OpenAI or Anthropic today, where buyers are already "predisposed to buy"—often get lazy and skip crucial steps.

To illustrate the value of hiring from difficult sales environments, Ben points to Ron Gabrisko, the original head of sales at Databricks. Before Databricks, Ron was a sales executive at a public company selling secure FTP software. Selling secure FTP at a public company requires an extraordinary level of sales discipline and intelligence just to hit your numbers. That forced discipline made Ron an exceptional hire who was fully equipped to build a playbook from scratch.

- **PTC Discipline:** Success required mapping out the entire customer organization, securing internal alignments, and systematically neutralizing competitors. - **The AI Hype Contrast:** Selling in-demand technology like modern AI tools is vastly different from entering a room where the prospect has never heard of your company and doesn't think they need your product.

[23:14](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1394s) Writing the Playbook and the HubSpot Interview Method

When evaluating a sales leader, a crucial distinction must be made: did they write the sales playbook, or did they simply run a playbook that was already set up for them? Joining a company like VMware when it was already "on fire" and riding its momentum is very different from being the person who figured out how to lock out the competition, train the force, and establish the initial sales process.

The discussion shifts to HubSpot's highly successful, repeatable process for interviewing sales reps. HubSpot targeted candidates on their second sales job—not their first, and not their fifth—who had graduated from decent state schools and often had athletic backgrounds. The interview itself was a strict, 30-minute test designed to measure coachability rather than slick talking:

> "We came in for a half hour and the half hour was, 'Ben, welcome.' And I would give you a scenario and I would be the customer and I would say, 'Sell me HubSpot.' And I'd give you 12 minutes to sell me... I'd say, 'That's very good, Ben. Here's my feedback.' Couple minutes feedback. 'Why don't you think about it and let's do it again.' And if the person internalized that feedback and sold it better the second time, 99% of the time we hired them."

- **The Core Sales Skill:** The best sales reps are excellent listeners, not just fast talkers. - **The Coachability Test:** The ability to instantly internalize and apply critical feedback during a roleplay is the single best predictor of a rep's success.

[26:23](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1583s) Constructive Confrontation and the "F*** Off" Era

The conversation turns to the legendary, high-friction communication styles of early tech giants. The host reads a famous, incredibly blunt email sent by Marc Andreessen to Ben Horowitz during a high-stress product launch: "Apparently, you don't understand how serious this situation is. We're getting killed, killed, killed out there... Next time do the [f***ing] interview yourself. [F***] off, Marc." While modern corporate culture has softened, Ben argues that the very best companies are still led by founders who ask highly aggressive, blunt questions.

Ben recalls an interview story from PTC where sales legend John McMahon asked a candidate, "What would you do if I hit you in the face right now?" In another instance, Ben's first interviewer told him, "I wouldn't wear that suit to a [f***ing] fight." While such extreme behavior is outdated and often illegal today, the underlying need for "constructive confrontation"—a term coined by Intel's Andy Grove—remains vital. Grove famously told an employee who arrived late to a meeting, "All I have in this life is time and you're [f***ing] wasting it." This level of bluntness is necessary to establish a high-performance culture and ensure that bad news travels fast.

- **The Danger of Politeness:** Running away from the truth to preserve people's feelings is highly dangerous in a technology company. - **Culture Setting:** Aggressive, memorable call-outs by leadership serve as powerful stories that propagate throughout an organization, setting clear standards for behavior.

[30:16](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1816s) The Nuances and Dangers of "Founder Mode"

The conversation addresses the recent popularity of Paul Graham's "founder mode" concept, which was heavily inspired by Airbnb CEO Brian Chesky's experiences. After hiring highly senior executives, Chesky initially made the mistake of overly deferring to them, which led to the creation of political fiefdoms and internal bureaucracy. To save the company during the COVID-19 crisis, Chesky took back absolute control, operating in a highly hands-on, dictatorial "founder mode."

While Ben agrees that founders should not blindly defer to executives, he warns that many founders are misinterpreting "founder mode" to mean they shouldn't hire senior people at all. This is a dangerous mistake. If a startup is trying to scale and compete globally, a founder cannot build a massive, worldwide sales organization from scratch without hiring experienced, senior executives who actually know how to run a large-scale playbook.

[03:12:26](https://www.youtube.com/watch?v=dFT4xj57D7U&t=11546s) The Nuance of "Founder Mode" and Managing Experienced Executives

The conversation dives into the nuances of "founder mode," a concept popularized by Paul Graham. Ben Horowitz warns that some founders have overcorrected by completely avoiding experienced hires, fearing they will lose control of their companies. While it is true that bringing in a big-company executive can be disastrous if they try to run a startup on your dime, completely avoiding outside expertise is a mistake, particularly for enterprise companies. Critical roles like Chief Financial Officer (CFO) require deep, specialized outside knowledge. The key to founder mode is not avoiding these people, but learning enough about their jobs so that you have the confidence to manage them and tell them what to do, rather than letting them dictate terms to you. "That's when you lose the company," Horowitz notes.

The speakers compare different leadership playbooks, noting that while Nvidia's Jensen Huang famously manages 60 direct reports and gives feedback in public, almost none of the CEOs they coach actually replicate this style. Similarly, very few people outside of Elon Musk's companies successfully implement Musk's "algorithm." Horowitz explains that running a company like Jensen requires an immense level of confidence and a specific philosophy: you cannot spend time developing your executives. They must already be CEO-caliber.

- **The Zuckerberg Path:** Mark Zuckerberg did not start out with this level of absolute confidence. Early on, he deferred half of the company to Sheryl Sandberg while he built up his operational confidence. Horowitz notes that going from "zero to Jensen" is incredibly difficult, especially considering Jensen has been honing his playbook for over 30 years. - **Zuckerberg's Strengths:** Zuckerberg excels at first-principles thinking, remains highly disciplined with data, and possesses an insatiable curiosity. Despite being labeled a "nerd," his people skills and psychological insights—evident in his M&A deals—are astoundingly good.

---

[03:16:39](https://www.youtube.com/watch?v=dFT4xj57D7U&t=11799s) What People Get Wrong About Culture

Horowitz, who wrote a book on the subject (*What You Do Is Who You Are*), explains that most founders do not actually understand what culture is. They mistake culture for "values"—which usually end up being identical, empty platitudes like "integrity" or "having each other's backs." In reality, culture is defined entirely by *behaviors*.

To illustrate this, Horowitz points to the venture capital industry. While every VC firm claims to "love entrepreneurs," many VCs behave arrogantly, show up late to pitch meetings, stay on their phones, or fail to follow up when they pass on a deal. Those behaviors, not the written values, define the actual culture.

- **The "Brilliant Jerk" Dilemma:** When dealing with highly talented but difficult people (like a "100x engineer" or a spiky VC partner), Horowitz argues that a simple "no assholes" rule never works because brilliant people often refuse to suffer through unproductive conversations. - **Setting Clear Parameters:** Instead of vague rules, leaders must define specific boundaries. At Andreessen Horowitz, Horowitz outlawed the behavior of making oneself look smart by making others look dumb. He explicitly warns his team that if they mock an entrepreneur on Twitter to look smart, they will be fired. - **The Steve Jobs Debate:** Horowitz and Marc Andreessen often debate whether Steve Jobs was mean because it was necessary for his brilliance, or simply because he was brilliant enough to get away with it. Horowitz believes it is the latter, warning that average founders who try to mimic Jobs' harshness will simply watch their talent walk out the door.

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[03:42:54](https://www.youtube.com/watch?v=dFT4xj57D7U&t=13374s) The Learning Curve of a CEO and VC vs. Entrepreneurship

Reflecting on his own journey as the CEO of Opsware, Horowitz admits that he did not truly feel like he knew what he was doing until about three and a half to four years into the job, after he rebuilt the sales force. He notes that everyone pretends to know what they are doing, but true confidence only comes with enough "reps." The more reps a leader has, the faster they can make decisions without worrying about mistakes or public opinion.

When asked about the online debate over whether venture capital or entrepreneurship is harder, Horowitz is unequivocal: "Venture capital is easier... Way easier. Like, that's not even close."

- **The Role of Luck:** In venture capital, a massive platform like Andreessen Horowitz or Sequoia provides a safety net, and a partner can find a trillion-dollar company through a fair amount of luck. - **The Brutality of Startups:** Entrepreneurs have only one shot, pay for their mistakes directly, and face relentless pressure. A tech founder might build a company to thousands of employees only to be forced to lay them all off, facing intense scrutiny from a single funding source, whereas VCs have multiple funding sources and do not operate on a quarterly clock.

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[03:46:33](https://www.youtube.com/watch?v=dFT4xj57D7U&t=13593s) Host's Reflection: Constructive Confrontation

Following the interview, the host reflects on his own shortcomings as the former CEO of HubSpot, admitting that he was highly conflict-averse. He notes that many first-time founder CEOs share this trait because confrontation is deeply uncomfortable unless you grew up with it. To combat this, the host highlights a valuable term he plans to borrow from Ben Horowitz: "constructive confrontation."

[47:08](https://www.youtube.com/watch?v=dFT4xj57D7U&t=2828s) Decision Debt and the Trap of the Popular CEO

A major pitfall for leaders is accumulating what Ben Horowitz calls "decision debt." This occurs when a CEO avoids making a difficult but necessary decision, choosing instead to kick the can down the road. At HubSpot, this manifested in classic ways, such as keeping a VP of sales on for too long in the desperate hope that they might somehow nail the next quarter, or delaying a much-needed overhaul of a scaling pricing model because the transition would be painful. This avoidance often stems from a lack of confidence and a deeply ingrained desire to be a "popular CEO"—a personal bug that can make leaders highly conflict-averse.

This hesitation and desire for popularity directly impact hiring and management, especially in the era of "founder mode." When first-time founder-CEOs hire highly experienced, "been-there-done-that" executives who are older and have more impressive resumes, they often feel too intimidated to truly manage them. Instead of directing them, the founder defers to them entirely, which is precisely where the organizational problems begin. To combat this, leaders must embrace a healthy level of "constructive confrontation" to keep their teams aligned and accountable.

- **Decision Debt Examples**: Keeping an underperforming VP of sales hoping they hit the next quarter, or delaying a pricing model redesign for several quarters. - **The Deference Trap**: First-time founders often fail to manage senior hires because they feel intimidated by their extensive resumes, leading to a loss of operational control. - **Constructive Confrontation**: A necessary leadership tool to prevent decision debt, particularly for naturally risk-averse or people-pleasing CEOs.

[48:29](https://www.youtube.com/watch?v=dFT4xj57D7U&t=2909s) Embracing the Discomfort of Hypergrowth

Running a hypergrowth company is an inherently uncomfortable experience. When an organization is scaling at a breakneck pace, everything is constantly breaking, processes are failing, and the landscape is shifting daily. It is entirely normal for a CEO to feel like they have no idea what they are doing.

Even highly successful leaders like Ben Horowitz during his time at Loudcloud, or the leadership at HubSpot, operated with this exact sense of uncertainty. Feeling unqualified or overwhelmed is not a sign of failure; it is simply the reality of navigating rapid scale.

- **The Reality of Hypergrowth**: Rapidly growing companies are characterized by constant breaking points and continuous change, making discomfort the default state. - **Normalizing Uncertainty**: Both Ben Horowitz at Loudcloud and the leadership at HubSpot felt they did not know what they were doing while building their massive enterprises.

## Notable quotes > [08:29](https://www.youtube.com/watch?v=dFT4xj57D7U&t=509s) If you were like a linebacker in the NFL and you were really fast, but you didn't trust your eyes, you would get cut. — Ben Horowitz

> [11:48](https://www.youtube.com/watch?v=dFT4xj57D7U&t=708s) grab a bag and sell some software — Ben Horowitz

> [11:48](https://www.youtube.com/watch?v=dFT4xj57D7U&t=708s) there is no fight without a prize — Ben Horowitz

> [23:14](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1394s) Ben, welcome. And I would give you a scenario and I would be the customer and I would say, 'Sell me HubSpot.' And I'd give you 12 minutes to sell me... I'd say, 'That's very good, Ben. Here's my feedback.' Couple minutes feedback. 'Why don't you think about it and let's do it again.' And if the person internalized that feedback and sold it better the second time, 99% of the time we hired them. — Brian Halligan

> [26:23](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1583s) Apparently, you don't understand how serious this situation is. We're getting killed, killed, killed out there... Next time do the [f***ing] interview yourself. [F***] off, Marc. — Marc Andreessen

> [26:23](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1583s) What would you do if I hit you in the face right now? — John McMahon

> [26:23](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1583s) I wouldn't wear that suit to a [f***ing] fight. — null

> [26:23](https://www.youtube.com/watch?v=dFT4xj57D7U&t=1583s) All I have in this life is time and you're [f***ing] wasting it. — Andy Grove

> [03:12:26](https://www.youtube.com/watch?v=dFT4xj57D7U&t=11546s) That's when you lose the company — Ben Horowitz

> [03:42:54](https://www.youtube.com/watch?v=dFT4xj57D7U&t=13374s) Venture capital is easier... Way easier. Like, that's not even close. — Ben Horowitz

## Mentioned Ben Horowitz, Sequoia Capital, a16z, HubSpot, Brian Halligan, Mark Zuckerberg, Larry Page, Dharmesh Shah, JD Sherman, Mark Cranney, Inbound Marketing, The Hard Thing About Hard Things, Ali Ghodsi, Elon Musk, Colin Powell, Shawn Maguire, Northeastern University, MIT Sloan School of Management, Google, Tesla, Databricks, Snowflake, Andy Grove, Sujay Jaswa, Dropbox, Okta, Todd McKinnon, Adam Aarons, PTC, Windchill, OpenAI, Anthropic, Ron Gabrisko, VMware, Marc Andreessen, John McMahon, Intel, Paul Graham, Airbnb, Brian Chesky, Nvidia, Jensen Huang, Sheryl Sandberg, What You Do Is Who You Are, Twitter, Steve Jobs, Opsware, Loudcloud

[Source](https://www.youtube.com/watch?v=dFT4xj57D7U)

中文简报

a16z霍洛维茨警告:盲从“创始人模式”恐致初创企业失败 初次担任CEO者往往因缺乏通过建设性对抗管理资深高管的信心,从而以“决策债务”使组织陷入瘫痪。 在这场内容广泛的对话中,Ben Horowitz 与主持人 Brian Halligan 深入探讨了成功科技领袖的核心特质,强调了纯粹智力、原创思维以及“良性偏执”的必要性。Horowitz 批判了早期初创公司中传统的 COO 角色,并告诫初次担任 CEO 者警惕过度顺从高管以及往往导致组织瘫痪的“决策债务”陷阱。他详细拆解了招聘复杂销售人才所需的严格纪律,阐述了真正的企业文化是如何由行为而非空洞价值观所定义的,并结合现实背景分析了近期兴起的“创始人模式”领导力。最终,讨论指出在超高速增长企业的规模化扩张过程中,深度的不适感与不确定性本就是常态。 顶尖科技公司往往由践行“建设性对抗”(constructive confrontation)的创始人领导,他们敢于直面残酷事实并确保坏消息快速传递,而不是为了顾及情绪而回避问题。 (0:00) Ben Horowitz 对早期初创公司的 COO 角色始终持怀疑态度,认为早期组织越扁平越好,盲目引入 COO 往往会破坏公司的“沟通架构”并产生双头管理的混乱。 (3:01) 创始人在快速扩张期最常因缺乏自信而陷入过度顺从高管或犹豫不决的“决策债务”(decision debt)陷阱;真正的创始人模式并非排斥资深高管,而是要有底气去管理比自己更有经验的人。 (8:32) 工程师背景的创始人招聘销售负责人极易踩坑,真正顶尖的销售高管不仅会在面试中反向严格考察初创公司的产品与商业可行性,还会自带一支忠诚的销售战队。 (11:48)

Reading summary

Andreessen Horowitz co-founder Ben Horowitz argues that exceptional founders succeed not through a uniform archetype, but through original thinking, intense talent density, and the decisiveness to practice constructive confrontation. He contends that startup failure commonly stems from decision debt, excessive deference to executive hires, and fundamental misjudgments regarding sales leadership and corporate culture. Founder Archetypes, Intelligence, and Productive Paranoia (3:58) Horowitz rejects the idea of a canonical CEO profile, noting that leaders like Mark Zuckerberg, Elon Musk, and Databricks CEO Ali Ghodsi possess starkly different personalities. Instead, he evaluates founders on original thinking that resists consensus and the ability to attract elite talent—echoing Colin Powell's definition of leadership as inspiring people to follow out of curiosity. Addressing the investor debate over hiring academic prodigies versus practical operators, Horowitz explains that while sales-led companies like HubSpot thrive on operational acumen, deep tech and platform companies require raw cognitive horsepower to conceptualize complex architectures. Furthermore, he identifies productive paranoia—exemplified by Ghodsi, Musk, and Andy Grove—as a decisive psychological edge, citing how Ghodsi's youth as a refugee fleeing Iran shaped his resilience and hypervigilance in outmaneuvering fierce competitors like Snowflake. Decision Debt, Flatter Structures, and Constructive Confrontation (8:32) The most prevalent failure modes for early-stage founders involve a collapse in operational confidence. When early mistakes occur, inexperienced founders often overcorrect by polling their executive teams or hesitating to make painful decisions, such as removing an underperforming executive. Horowitz compares a hesitant CEO to an NFL linebacker who gets cut for failing to trust his eyes, while former HubSpot CEO Brian Halligan characterizes this avoidance as accumulating "decision debt." To prevent communication bottlenecks, Horowitz remains skeptical of introducing a Chief Operating Officer early on, arguing that small startups require flat hierarchies; inserting an operational intermediary dilutes information flow and creates a disjointed "two people in charge" dynamic. High-performance cultures require what Intel's Andy Grove called "constructive confrontation"—asking blunt, aggressive questions to ensure bad news travels fast rather than letting politeness mask operational decay. Evaluating Sales Leadership and Complex Sells (11:48) Hiring go-to-market executives presents a severe trap for technical founders due to conflicting communication norms: engineers seek single objective truths, whereas skilled salespeople decipher why a question is being asked. Horowitz cautions against hiring candidates who merely coasted on tailwinds or high-demand products like modern generative AI tools. Instead, he favors veterans of difficult sales environments—such as the Parametric Technology Corporation (PTC) diaspora or Databricks hiring Ron Gabrisko from a legacy secure FTP vendor—who mastered rigorous qualification, competitor lockout, and stakeholder mapping. When evaluating sales leaders, founders should conduct blind backchannel references, demand candidates who qualify the company thoroughly (as seen in Todd McKinnon hiring Adam Aarons at Okta), verify whether loyal sales reps will follow them, and test reps on real-time coachability rather than polish. Calibrating Founder Mode and Enforcing Culture (30:16) While Paul Graham's concept of "founder mode" rightly cautions against surrendering authority to executive fiefdoms, Horowitz warns that founders overcorrect if they refuse to hire senior domain experts altogether. Scaling an enterprise globally requires experienced leaders in complex functions like finance; the founder's job is to understand those domains well enough to direct executives rather than defer blindly. Replicating extreme structures—such as Jensen Huang managing 60 direct reports at Nvidia—requires decades of refined operational confidence. Horowitz also clarifies that culture consists of observed behaviors rather than abstract values like "integrity." True culture is established by setting non-negotiable behavioral boundaries, such as firing staff who humiliate others. He notes that copying Steve Jobs' harsh demeanor without his unique genius will simply drive talent away, while underscoring that venture capital remains vastly easier than entrepreneurship, where founders bear solitary, unhedged operational risk. Both Horowitz and Halligan conclude that uncertainty and breaking points are the default conditions of hypergrowth startups rather than indicators of executive failure. A founder's trajectory depends on embracing that discomfort, resisting the impulse to seek popularity among peers or staff, and actively resolving operational friction before organizational momentum stalls.

精炼阅读摘要

Andreessen Horowitz 联合创始人 Ben Horowitz 在与 Brian Halligan 的对话中指出,科技公司的生死取决于创始人能否保持独立思考、维系扁平高效的沟通架构,并在规模化扩张中克服讨好心态与决策拖延;真正的领导力在于敢于推行“建设性对抗”,在不盲目放权的前提下学会有效管理外部资深人才。 创始人核心特质与扁平沟通架构 (3:01) Horowitz 认为优秀创始人没有固定模板,核心在于具备独立思考能力、极强的吸纳顶级人才的号召力,以及匹配赛道需求的原始智力。例如 Databricks 首席执行官 Ali Ghodsi 兼具计算机博士的科研功底与难民经历塑造的“极度偏执与警惕感”,这与 Andy Grove 和 Elon Musk 的心理特质高度一致;而对于 HubSpot 这类偏重营销与销售创新的公司,吸纳普通高校人才同样取得成功,并非必须依赖数理奥赛冠军式的纯技术神童。 在组织设计上,Horowitz 长期质疑早期设立 COO(首席运营官)的做法。他指出科技企业的成败与“沟通架构”深度绑定,初创企业组织越扁平越好。早年流行的“内部分工、外部分工”双头模式在产品平稳期或能短期维持,但一旦企业进入产品周期尾声需要转型创新,COO 的隔离层往往会阻断真实信息流动,引发权责不清并最终导致体系瓦解。如果 COO 仅代表销售负责人头衔尚可接受,但若由其代管日常运营而创始人退为前台门面,则极其危险。 克服决策负债与厘清“创始人模式” (8:32) 初创企业在规模化过程中最常见的失败源于创始人缺乏自信。新手创始人在犯错后容易走入两个极端:一是“过度服从”,通过在聪明员工中搞民意测验来治理公司,导致失去业务全局视角并滋生内部政治;二是“犹豫逃避”,因害怕犯错或过度在意董事会与团队看法而推迟艰难决策。Halligan 将其称为“决策负债”,并指出希望成为“受欢迎的 CEO”会使领导者回避冲突,导致迟迟不换掉不称职的高管或拖延重构定价模式。Horowitz 强调,CEO 必须像优秀的橄榄球中卫一样信任自己的眼睛并果断冲向问题,否则就会被淘汰。 针对近期备受推崇的“创始人模式”,Horowitz 警告创始人切勿矫枉过正。Airbnb 首席执行官 Brian Chesky 在疫情期间通过收回集权拯救了公司,但这并不意味着企业可以拒绝招募资深高管。在全球化销售与企业财务(如 CFO)等专业领域,完全排斥大公司资深管理者是致命的。创始人模式的精髓在于深入了解专业岗位的挑战与运作逻辑,建立起主动指挥、考核专家的自信,而不是被外部高管光鲜的简历吓倒而彻底放弃业务主导权。 销售高管选拔、追随者与硬仗纪律 (11:48) 技术背景创始人招聘销售高管时常因沟通范式差异而踩坑:工程师习惯寻找客观唯一答案,容易将销售人员探寻问题动机的习惯视为闪避;而销售的本质是在竞争陷阱与客户诉求中周旋。Horowitz 以 Okta 早期聘用 Adam Aarons 为例指出,优秀的销售候选人不会盲目热情迎合,而是会像审视潜在客户一样严格核验初创公司的商业与产品可行性。创始人不能仅凭面试好感做决定,必须借助深层人脉进行盲测背景调查,否则错误的高管任命足以让企业濒临破产。 优秀的销售领导者必须具备“追随者”检验指标:顶尖销售高管麾下通常有一批随时准备跟随跳槽的骨干销售团队,例如 20 世纪 90 年代 PTC(参数技术公司)销售体系走出的精英网络。PTC 当年销售技术难题频发的复杂软件,迫使销售人员严密规划客户组织关系、锁定竞争对手,这种在恶劣环境下建立严谨销售纪律并亲自谱写战略体系(Playbook)的人才,远比在顺风期或暴利单品中充当“接单员”的销售更具实战价值。针对一线销售考核,Halligan 介绍了 HubSpot 的 30 分钟角色扮演面试法,重点考察候选人在接受现场反馈后能否立刻吸收并优化销售表现(Coachability)。 行为定义的企业文化与建设性对抗 (26:23) Horowitz 强调企业文化是由“具体行为”而非墙上悬挂的抽象“价值观”定义的。许多风投机构声称热爱创业者,但在路演中看手机、迟到或拒绝后毫无交代,这些行为才是其真实文化。针对能力超群但性格棘手的员工,生搬硬套“杜绝混蛋”规则往往无效;管理者必须划定明确的行为界限,例如 a16z 明文严禁员工为了显摆聪明而在公开社交平台上嘲笑创业者。对于模仿 Steve Jobs 严厉作风的现象,Horowitz 认为乔布斯的苛刻是其绝顶才华掩盖下的缺陷,缺乏同样才华的普通创始人盲目效仿只会加速人才流失。 高绩效组织必须贯彻 Andy Grove 所倡导的“建设性对抗”,确保坏消息能够光速上传,而不是为了顾及他人情绪而掩盖事实。Horowitz 坦言自己在 Opsware 摸爬滚打三到四年、彻底重构销售团队后才真正找到做 CEO 的感觉。他明确表示风险投资的难度远低于亲自创业:大型投资机构拥有强大的容错平台与运气成分,而创业者背负着员工生计、融资审视与破产的单点压力,必须在持续不断的混乱与不确定性中承受剧烈痛苦并独立承担所有错误代价。 本场对话阐明了高增长科技企业中创始人认知的蜕变路径:领导者必须从初期的决策犹豫、取悦心理与对职业经理人的盲目服从中解脱出来,通过推行直面真相的建设性对抗来维系敏捷的沟通架构。然而,如何在践行“创始人模式”以保持绝对掌控力的同时,准确界定自身知识边界并有效驾驭外部专业高管,依然是初创企业跨越规模化鸿沟时悬而未决的核心挑战。

Source quotes

[8:29] Ben Horowitz: If you were like a linebacker in the NFL and you were really fast, but you didn't trust your eyes, you would get cut. [11:48] Ben Horowitz: grab a bag and sell some software [11:48] Ben Horowitz: there is no fight without a prize [23:14] Brian Halligan: Ben, welcome. And I would give you a scenario and I would be the customer and I would say, 'Sell me HubSpot.' And I'd give you 12 minutes to sell me... I'd say, 'That's very good, Ben. Here's my feedback.' Couple minutes feedback. 'Why don't you think about it and let's do it again.' And if the person internalized that feedback and sold it better the second time, 99% of the time we hired them. [26:23] Marc Andreessen: Apparently, you don't understand how serious this situation is. We're getting killed, killed, killed out there... Next time do the [f***ing] interview yourself. [F***] off, Marc. [26:23] John McMahon: What would you do if I hit you in the face right now? [26:23] null: I wouldn't wear that suit to a [f***ing] fight. [26:23] Andy Grove: All I have in this life is time and you're [f***ing] wasting it. [192:26] Ben Horowitz: That's when you lose the company [222:54] Ben Horowitz: Venture capital is easier... Way easier. Like, that's not even close.

Original transcript

[0:00] I think really good companies [0:02] the very very very very best companies [0:05] tend to have founders and CEOs who ask [0:07] pretty aggressive questions. Zuckerberg, [0:10] Larry Page, those guys who have kind of [0:13] gotten all the way to the mountain top, [0:15] they're pretty blunt. If you're running [0:17] away from the truth to preserve [0:18] feelings, that's a very dangerous thing [0:20] in the tech company. And the kind of [0:22] corollary to that is it's really [0:24] important that like bad news travels [0:26] fast. [0:27] >> Yeah. That you know if something's wrong [0:29] that a CEO you find out about it. And so [0:32] you need that bluntness. [0:39] >> [music] [0:51] >> Everybody, today's guest is Ben Horowitz [0:53] of A16Z fame. Few reasons I wanted to [0:56] have him on. First, I wanted to get the [0:59] behind the scenes look on why Andreessen [1:03] passed on HubSpot back in the day and [1:05] there's a funny story behind that. He's [1:07] seen so much. He's backed some amazing [1:10] CEOs and some CEOs that went down in [1:13] dust. Like what do they have in common? [1:16] What do the great ones What do they do? [1:18] What are they like? What's What's the [1:19] patterns there? And then what's the same [1:21] with the ones who failed? [1:22] I read his book like a hundred years ago [1:24] when I was running HubSpot. I thought it [1:26] was really good. [1:28] I think he published it in 2014. I [1:30] wanted the updated, you know, what's [1:32] changed since he wrote The Hard Thing [1:34] About Hard Things back in the day. [1:36] The convo's I think it's really good. [1:38] One of the things I've always liked [1:39] about Ben is he is completely unfiltered [1:41] and gets after it. I think there's a lot [1:43] of nuggets in here. I'll come back at [1:45] the end and give you my summary. You [1:46] probably don't remember when we first [1:48] met. Can I Can I [1:49] >> Yeah, yeah, remind me. Can I tell you [1:50] about it? It's It's stuck in my mind. [1:52] Kind of a long story. HubSpot pitched [1:54] you on the Series D. [1:56] >> Okay, I remember that. Yeah. Three of us [1:58] came in for the pitch, our very newly [2:00] hired COO, JD Sherman, Mhm. myself, and [2:03] my co-founder, Dharmesh. And we walked [2:05] in the room, we had a nice welcome [2:06] because there's a guy that worked for [2:08] you that was your sales guy, named Mark [2:10] Cranney, that was a former colleague of [2:11] mine. And then we had just written a [2:13] book called Inbound Marketing, and two [2:15] of your marketers had the book, so we [2:16] were like, this is a hometown we got [2:18] this. [2:18] >> yeah, yeah. Okay, we sat down, [2:21] and JD sat here, and I sat here, and [2:23] Dharmesh sat here. I remember like it [2:24] was yesterday. And we started with [2:26] intros. JD barely got a sentence out of [2:28] his mouth, like, wait, you're the COO? [2:31] Tell me about your background. You spent [2:32] like 15 minutes on JD. You spent like 15 [2:34] minutes on JD, and then went to me, and [2:37] then spent 15 minutes on me, like, [2:38] you're such an [ __ ] why did you hire [2:40] a COO? And then Dharmesh. Anyway, you [2:42] guys passed, as did everyone. Two weeks [2:45] later, I read your book. Ah. And I saw [2:47] in the book that [2:49] you're not a fan of the idea of hiring a [2:50] COO. So, I guess my question And by the [2:52] way, I think chips on the shoulder are [2:54] really I know. You put a chip, a [2:56] ginormous chip, on JD Sherman's [2:58] shoulder. [2:59] >> Oh, good. [3:00] It was incredibly beneficial. How do you [3:02] feel about CEOs COOs these days? You [3:04] Same same thing, or change your mind? [3:06] Well, no, I mean, I I think that [3:08] generally, when a company is small, [3:09] flatter is better. In the early 2000s, [3:12] it was a very popular construct, and it [3:14] was kind of mister outside, mister [3:16] inside, that kind of thing. [3:18] You know, if you're really scaling, um, [3:20] and you're not kind of wrestling with [3:23] product market fit, it like it can work [3:25] for a time [3:27] on a product cycle, but when you hit the [3:29] end of the product cycle, it's [3:31] Yeah, so much about a company, a tech [3:33] company, is kind of the communication [3:35] architecture, [3:37] and it just makes that worse, generally. [3:39] It's a little like two people in charge. [3:41] Not to say it can't work, and you know, [3:43] it depends on the definition of COO, and [3:45] if COO is really just a big title for [3:47] the sales guy, like that's fine, you [3:49] know. COO in the sense that I'm running [3:51] the company and you're like Mr. Thug Man [3:54] outside. [3:55] I think that's not a great thing for us [3:57] to have. [3:58] You've invested in tons of CEOs at this [3:59] point, coach tons. [4:01] What like what are you looking for? [4:03] What's like a major green flag, red [4:05] flag? How's it changed over time? Like [4:07] what's your filter? [4:09] On a CEO? Founder CEO. So you're looking [4:11] at the company in the market, but the [4:12] person. Not the co-founder, the CEO. The [4:15] thing about founder CEOs is that [4:19] there's definitely not what I would [4:21] consider like a canonical one. So if you [4:23] look at [4:25] Mark Zuckerberg [4:26] and Ali Ghodsi and Elon Musk, they're [4:29] all like extremely different types of [4:30] people. So [4:32] you know, you try not to get into like [4:36] anything about the look and feel or [4:38] sound or like you know, are they very [4:40] extroverted? Are they very introverted? [4:42] Or this kind of none of that I think [4:43] matters. There's a few things in common. [4:45] One is [4:47] you know, anybody great uh [4:50] really thinks for themselves. So they [4:51] don't feel like they're reading the room [4:53] or influenced by what I'm going to say [4:55] or anything like that. [4:56] >> And you could probably figure that out [4:58] during the pitch, you think? Well, you [4:59] can figure out if they're not that [5:01] during the pitch, for sure. And then [5:04] you know, do they have like truly [5:05] original thinking on things? So and then [5:08] you know, from a leadership standpoint, [5:10] I really like the Colin Powell [5:12] definition, which is you know, [5:13] leadership is the ability to get people [5:14] to follow you if only out of curiosity. [5:17] >> [laughter] [5:17] >> Um so so I think, well, would I want to [5:20] work for this person? Like how [5:21] interesting are they? And if you don't [5:23] have that, right, you're not going to [5:25] bring in the super high-end talent, [5:27] which is [5:28] you know, it's kind of a a momentum [5:30] thing. If you can't hire the very, very [5:34] top talent, then you're not very [5:35] unlikely to be a great company. It's [5:37] kind of you know, how good is your [5:39] talent density and all that kind of [5:40] thing. So We just had our Sequoia [5:42] offsite and I got into not an argument, [5:45] but discussion with uh Shawn Maguire, [5:47] one of our partners. [5:48] >> Yeah. Yeah, he's very outspoken. [5:49] >> Very outspoken. And he got up and he [5:51] said, "What we should be looking for are [5:54] these founders that won the chess [5:56] Olympiad or the math Olympiad in high [5:58] school and surrounded by other of those [6:00] folks." And he was very articulate and [6:02] made a good point. A lot of people shook [6:04] their head. And I thought about it and I [6:06] was like, "Well, HubSpot's no [6:08] Tesla, but it did pretty well. And my [6:12] co-founder and I, we're Sloan people. [6:13] Not, you know, [6:14] >> Yeah. And then we hired crap tons of [6:16] people from Northeastern. And I was [6:17] like, "It worked out pretty well." And [6:19] then I just think like early in the [6:21] cycle, maybe you need those PhDs and [6:23] those, you know, chess champions, math [6:26] champions. But as it moves up the stack [6:28] as Salesforce and ServiceNow kind of [6:29] look like us. Do you have a take on my [6:32] disagreement with Shawn? Well, I think [6:33] it depends a little on [6:36] the era and the market. So, if you look [6:38] at HubSpot, right? Like it was a [6:40] marketing sales idea as much as it was a [6:44] technological idea. So, you have to have [6:47] great people on that side who tend not [6:49] to be math Olympiads. [6:50] >> Yes. [laughter] [6:51] And so, for that company, I don't think [6:53] that's right. For other companies, [6:55] that's right. The other thing is, you [6:56] know, math Olympiad is very specific. [6:59] The very best companies are founded by [7:02] exceptionally smart people. There's no [7:04] question about that. I agree with him on [7:06] on that angle of it. You know, like how [7:08] smart is Elon? Extremely [ __ ] smart. [7:10] Was he math Olympiad? Probably not. Like [7:12] I don't think so. But just like raw [7:15] horsepower is pretty important. Like [7:16] Larry Page is probably [7:18] you know, one of the smartest people in [7:19] the world. That ends up mattering if [7:21] you're going to build something Google [7:22] size. [7:23] Um it's very hard to imagine that [7:25] without somebody like Larry Page who [7:27] could even think of something that big. [7:29] Yeah. You've worked with a lot of CEOs. [7:30] Who's the best? Probably the best one [7:32] that I personally work with right now is [7:34] Ali Ghodsi at Databricks. Yeah, he's a [7:36] PhD in computer science. He's extremely [7:38] smart. Um so, he kind of meets the Shawn [7:40] Maguire test. But he's like an [7:42] exceptionally good, you know, for an [7:44] enterprise software CEO, he's [7:46] exceptionally good at go-to-market, able [7:48] to compete with Snowflake, which was a [7:50] very, very good go-to-market [7:51] organization. And then he's just [7:54] absolutely [7:56] paranoid. The The only person I ever [7:58] known as paranoid as LA. I mean, I guess [8:01] Elon is this level of paranoid, but Andy [8:03] Grove was this level of paranoid. [8:06] >> yeah, exactly. You know, I think some of [8:08] that comes from him being and he's a [8:09] refugee. [8:10] Uh [8:12] you know, he grew up in Iran and then [8:14] when they Ayatollah Khomeini came in, uh [8:16] he had to flee to Sweden. Hopefully [8:19] that's uh correcting now finally after [8:21] all these years, but you know, that [8:23] having everything taken away from him, [8:26] um [8:27] really informed his psychology in a way [8:29] that's I'd say very beneficial for a [8:31] founder. [8:31] >> Mhm. Okay, I work with a lot of [8:33] founders. Their companies are growing [8:34] fast and I'm kind of new to this. What's [8:38] the pattern of mistakes these folks make [8:40] on the way up? What are the common [8:41] traps? [8:44] So, [8:45] like I think the universal one is kind [8:47] of starts with It's kind of confidence [8:50] is way kind of in a word. [8:52] But it starts with the fact that nobody [8:55] knows what they're doing is you probably [8:57] have experienced yourself. You have an [8:59] idea. You invent something. [9:01] You don't know how to run a company. No [9:02] idea. And so you start, you know, [9:04] building the company and you make [9:07] a lot of mistakes. Those mistakes are [9:10] extremely [9:11] damaging. You feel terrible about it [9:13] because you hired all the people, you [9:15] sold them on this great idea. Then you [9:16] make a mistake and everybody gets hurt. [9:19] And if you've not kind of been in a [9:21] position like that, which almost no [9:22] founder has, it can be like highly [9:24] psychologically challenging. And you see [9:27] people react to it in two very dangerous [9:31] ways. One is they overly defer. So, [9:35] okay, I hired a lot of smart people. I'm [9:37] going to be very open to their input on [9:39] all the decisions to the point where I'm [9:41] not really making the decision myself. [9:43] I'm kind of [9:45] doing a poll. But, nobody other than the [9:48] CEO has the context to make that [9:50] decision. Nobody kind of sees the whole [9:52] picture. And so, that can lead you into [9:55] not only bad decisions, but a very [9:57] dangerous political environment where [10:00] people go, "Oh, there's a vacuum here. I [10:01] can step into it." [10:03] And then the second thing that you see [10:05] often is just hesitation. [10:08] I don't know what the right answer is. [10:10] I have a suspicion. I'm like 52/48 on [10:14] it, but I'm afraid to make a mistake, so [10:16] I'm I'm going to not decide. And then [10:19] the other kind of hesitation is, "Well, [10:21] I'm going to avoid it." Like I see [10:23] something bad. I really need to fire the [10:25] head of sales. What is the press going [10:27] to say? What is my board going to say? [10:29] What is this going to be? Da da da da [10:30] And you're thinking about everything [10:32] that you should not be thinking about [10:34] rather than [10:35] can this person do the job? And those [10:37] things are really what cause founders to [10:40] fail at the CEO job. That that lack of [10:42] confidence, that hesitation. You know, [10:44] when I talk to CEOs, I'm like, "Look, if [10:46] you were like a linebacker in the NFL [10:48] and you were really fast, but you didn't [10:49] trust your eyes, you would get cut." [10:52] Because you won't get to the No matter [10:54] how fast you are, you're not going to [10:56] get to the ball carrier in time. If you [10:57] don't trust your eyes as CEO and go run [11:00] at the problem and make the decision, [11:03] you're going to fail. You're going to [11:05] get Like that's what's going to get you [11:06] replaced. It resonates with me. At [11:08] HubSpot, we had [11:11] all kinds of debt, culture debt, product [11:13] debt. We had decision debt at times, I [11:15] would call it. Yeah, yeah. And when the [11:17] company would [11:17] >> Decision debt is the worst debt, by the [11:19] way, cuz it it paralyzes a company. We [11:21] had I had it. So, I fell in your trap. [11:24] And the way it kind of worked was I [11:26] would see the company [11:28] slowing down and just like a lot of [11:31] debate and a lot of just stuff on my [11:34] desk. [11:35] And then once every like four, five, six [11:38] months be like, I need to make some [11:39] freaking decisions. And then once I made [11:41] some decisions, it just kind of [11:43] everything just started moving and [11:44] flowing. So, I felt that very much. [11:48] One other mistakes that I made talk [11:49] about the team building like you hired a [11:51] lot of VP of sales like People [ __ ] up [11:54] their VP of sales hires all the time. [11:55] >> More than anything else, [laughter] [11:56] yeah. More than anything else. So, kind [11:58] of more generically hiring executives [12:00] Yeah. is also something you don't know [12:02] how to do. Right? Like it's [12:05] A lot of times you don't even know what [12:06] the job is. Like [12:08] what is a CFO? What's a control [12:10] structure? [12:11] You know, what are these systems they [12:12] speak of? [12:14] And [laughter] Yep. people go into hire [12:17] them like with that level of knowledge [12:20] and think they can like smell it out [12:22] from talking to a person and it's a [12:24] little like trying to hire a Japanese [12:26] interpreter and you don't know Japanese. [12:27] Like they're they're all going to sound [12:28] pretty good. And it's going to be very [12:30] hard for you to distinguish. So, [12:32] preparation I would say is very [12:34] important in terms of okay, have you [12:37] spoken to enough CEOs? Have you asked [12:40] them like what's the difference between [12:42] a good CFO and a great CFO? Like, you [12:44] know, [12:45] how would you hire this person? What [12:47] would you ask them? What would you want [12:49] to see? Um, you know, these kinds of [12:50] things. And just understand the job. I [12:53] always say [12:54] if you have a chance, just try to do the [12:57] job yourself, act in that role so that [12:59] you can get a [13:00] a feel for what the challenges in your [13:02] company. And it's also right like you [13:04] don't want a generic CFO, you want one [13:07] for your business. Then when you get [13:09] into sales, so the problem that that we [13:12] have all the time is we have engineers [13:14] running the company. [13:15] And then they're hiring a head of sales. [13:17] You could not be culturally different [13:21] between like an engineer and a head of [13:23] sales. The main thing is [13:25] like right down to how they talk to you. [13:27] So, engineers, if you ask them a [13:30] question, [13:31] 100% of them [13:33] will try and think of what is the [13:35] correct answer to that question. That's [13:37] how they think about it. If you're a [13:39] sales person, your first thought isn't [13:41] what's the answer, it's why the [ __ ] are [13:43] you asking me that question? [13:44] Right? Because that's a clue. [13:47] And so, you know, if you ask a an [13:49] engineer, like, "Does your product have [13:50] this feature?" The answer is yes or no. [13:54] If you ask a sales guy, it's like, [13:56] "Okay, what competitor was in here that [13:58] planted that trap for you? What's their [14:00] weakness and how do I get to that?" And [14:02] so, if you have an engineer talking to a [14:04] head a good sales guy, it's going to [14:06] upset them because they're often not [14:09] going to answer the question. They're [14:10] going to try and figure out why they're [14:12] being asked that question. And so, then [14:15] I like this, by the way. I hadn't [14:16] thought of it this way. [14:16] >> Yeah, but the the the guys who are good [14:18] at the job get rejected because you [14:21] don't like them. And then the people who [14:23] are terrible at it, those are the ones [14:25] that that end up getting hired. My Mark [14:26] Cranney used to say, you know, that [14:28] these CEOs they just want to take a guy [14:31] who failed the engineering test, put a [14:32] clean shirt on him, and like make him [14:34] head of sales. And and there's a real [14:37] truth to that. It's funny, I had this [14:38] conversation with Sujay when he was at [14:41] Dropbox. He goes, "How do I like deal [14:44] with the fact that our engineers are [14:45] upset that we're going to pay the sales [14:47] guys commissions?" [14:49] I would guarantee guarantee they're [14:51] going to be upset. Yeah, and I said, [14:52] "Well, it's very simple. Tell them [14:55] if they want to make commission, then [14:57] they can [ __ ] grab a bag and sell [14:59] some [ __ ] software. [15:00] And if they don't hit their number, [15:02] you're going to fire them. And if they [15:03] want that job, they can get a [15:05] commission. But otherwise, you know, [15:06] shut the [ __ ] up." [15:08] You know, he said, "Oh, okay. I never [15:09] thought of it that way." I was like, [15:11] "Look, [15:12] the other question you can ask them is, [15:13] do you have engineers that like [15:16] on the weekend might write some software [15:18] for fun, like as a as a hobby?" And he [15:21] goes, "Yeah." And I said, "I guarantee [15:23] you don't have a single [ __ ] sales [15:24] guy on the weekend who's selling [15:25] software as a [ __ ] hobby." Like Like [15:27] that That is not a fun job. There has to [15:29] be a It's a prize fight. There is no [15:31] fight without a prize. [15:33] And I think that the whole mentality, [15:35] the whole cultural difference between [15:38] like what founders are and what sales [15:41] people are is so vast that [15:44] you know, somebody's got to have a [15:46] conversation with them about like, [15:47] "Okay, what are you really looking for?" [15:49] Because otherwise [15:51] you're just going to get somebody who's [15:52] not good at sales. [15:53] >> Okay, I'm the head of I'm an engineer. [15:55] I'm CEO of your brand new company. [15:59] I'm likely to screw the hire up. What's [16:01] your advice to me? [16:02] Yeah. [16:03] Well, it's funny. So, one of the [16:05] companies that both Sequoia and we were [16:08] invested in is a company called Okta, [16:10] which ended up doing [16:11] uh very well. It's actually Pete Grady. [16:13] I was on the board with Pete Grady on [16:14] that one. I know those guys. Yeah, and [16:16] you know, the very first like big [16:18] mistake that Todd almost made was hiring [16:21] the head of sales. There were two [16:22] candidates. One I I forgot his name and [16:25] the other was Adam Aarons, um who was [16:26] PTC guy. You know, we knew everything [16:28] about Adam because, you know, he had [16:30] worked for Cranny, you know, he had [16:32] worked for McMahon. Like I I knew [16:33] everybody in the tree. [16:35] And I called them all and they were [16:37] like, "This is the guy." [16:39] And then this other guy, you know, I got [16:41] front door references on him. [16:42] >> Yep. And [16:44] they came out okay. Like not great. [16:46] >> Yeah. But Todd wanted to hire this other [16:48] guy and the reason that he wanted to [16:50] hire him was he was much more [16:53] enthusiastic about Okta. Whereas Adam [16:55] was like, [16:56] "Well, I don't know about this company. [16:58] Let me talk to some of your customers." [16:59] and so forth and that kind of thing. [17:00] >> Yeah. [17:01] And so, you know, the conversation I had [17:03] with Todd was I was like, "Todd, you [17:05] don't want the sales guy all enthus- [17:07] They You want them to be qualifying [17:09] you." [17:10] >> Yep. Because when you're selling [17:13] good sales guys don't just answer the [17:15] damn questions they're being asked. They [17:17] qualify the customer. Do you really have [17:19] the money? Do you really have the need? [17:21] Do I really have a shot here or am I [17:23] politically already boxed out? You need [17:26] that. And I said, but beyond that [17:29] I got guys who owe me favors more than [17:31] they owe Adam favors [17:33] telling me he's great. [17:34] >> Yep. And this other guy who all the guys [17:37] owe him favors and don't owe me anything [17:40] say he's a B. [17:42] And so do not [ __ ] this up. I'll never [17:45] forget it. And I I don't talk to [17:47] founders like this anymore cuz I'm more [17:49] mature. But I said Todd [17:51] >> Sure. [17:52] >> [laughter] [17:53] >> I'm still working on that. I said Todd, [17:54] look, if this hire doesn't work cuz we [17:56] were in a lot of trouble at the time. [17:58] You realize what's going to happen is [18:00] this is the end of your company. Like [18:02] this is it. So you got to be 100% [18:05] confident cuz I'm telling you you're [18:07] wrong. [18:08] And I'm more experienced at this than [18:09] you and so forth. So I really put [18:11] pressure on him. And he hired Adam and [18:13] you know, it ended up really making the [18:15] company. So I have a bunch of I have a [18:16] bunch of questions on But that's how [18:18] important is it? Like I think if we had [18:19] hired the other guy, Okta would have [18:20] gone bankrupt. Ooh. [18:22] I have a couple questions on that. It [18:24] sounds well, just the takeaway of I'm [18:26] that engineer who's CEO, I'm getting [18:28] some traction, hiring that as sales. [18:30] It's one, blind references really [18:32] matter. [18:33] And two, get a board [18:35] >> sales [18:36] by the way [18:37] it's the whole thing. Yeah. [18:39] Also who are you bringing with you? [18:42] Yeah. That's what I always ask. Who are [18:43] you bringing with you? [18:44] Okay, you're bringing this, that, and [18:45] the other. Okay. Can I call them? [18:47] >> Mhm. [18:48] And find out if they're coming. Yeah, [18:49] yeah, yeah. Cuz [18:51] any great sales leader [18:53] has big set of followers. [18:55] And anyone who's not great Nobody. [18:58] Nobody. Cuz [19:00] the one thing sales guys are, they're [19:01] savvy about the leader. Yes. [19:03] Like you've I've never met even a [19:05] mediocre sales person knows who's a good [19:07] leader. Okay, you brought up PTC a [19:09] couple you hired people from PTC. I came [19:11] from PTC. First of all, who's the [19:13] equivalent of PTC now? Building on the [19:16] sales leaders that are filling Silicon [19:17] Valley. I can't figure that out. And [19:19] two, what do you think it was about the [19:21] PTC mafia that worked so well? And by [19:24] the way, for listeners, PTC was a great [19:26] still a great company, but in the '90s, [19:28] it ripped and was fastest growing [19:31] company in the world for a while and we [19:32] sold CAD/CAM, we sold PLM software to [19:35] manufacturers. Hard sell, but we were [19:37] very good at it and the diaspora of PTC [19:40] sales execs throughout Silicon Valley [19:41] was very interesting and compelling. [19:43] There was a number of things about PTC, [19:45] but one of the underrated things was the [19:47] product wasn't that great. [19:49] Particularly the Windchill. The hoopla. [19:52] >> Didn't work. Yeah. [19:53] >> [laughter] [19:53] >> Anybody can say [19:54] >> like when you you like to hire a sales [19:56] guy that had a hard sell. You don't like [19:58] to hire somebody was like, "Yeah, he [19:59] crushed his numbers, but anyone could [20:01] have sold that." Yeah, like hire [20:03] somebody selling Google AdWords. Like [20:05] like you know what that job is? [20:07] How much do you want? [20:08] >> [laughter] [20:09] >> Okay. You're not going to build the this [20:12] >> see someone from Databricks though and [20:14] they were VP of Databricks and you're [20:15] looking for a CRO in your new company. [20:17] I'm not saying that's easy to sell, but [20:18] they have a brand, they have like a lot [20:20] of mojo. Is is that someone you're [20:22] looking for in an early stage startup or [20:23] no? Well, [20:25] you know, I can't comment on that [20:26] because you know, Databricks is [20:28] >> Well, do you know the analogy? Yeah, [20:30] it's like the early days of Oracle. [20:32] Those guys were different than an Oracle [20:34] salesperson today, right? And I think [20:37] that [20:38] like as it gets more established, it's [20:39] harder to tell because [20:42] you can survive on that, but I I I will [20:44] say this, if you have a product that's [20:46] complicated to sell, [20:48] then that's when you get to the PTC [20:50] level. The thing about PTC [20:53] that was so amazing other than like the [20:55] culture and the attitude. So this So [20:57] there's a culture and the attitude and [20:58] we talked about that which was unique [21:01] and probably illegal today. [21:03] >> [laughter] [21:03] >> I would say almost certainly illegal [21:05] today. But the thing that [21:07] I think is very replicable [21:10] but only if you have a difficult product [21:12] to sell is a discipline. And the [21:13] discipline really came down to, okay, [21:17] you're going into an account. [21:19] You know there are competitors and how [21:22] systematic are you about laying the [21:25] traps for the competitors, you know, [21:28] making sure you make a comprehensive [21:30] technical case, a comprehensive business [21:32] case, making sure that you've charted [21:35] everybody in that organization who's in [21:36] that decision process and it's a very [21:38] complicated decision process for PTC. [21:41] Getting [21:42] assurances that they're all like lined [21:44] up. [21:45] And that's so complicated and requires [21:48] so much courage and effort and [21:50] competitiveness that that translates [21:53] into anything. [21:55] Whereas [21:56] look, if you're walking into an account [21:58] and they're already predisposed to buy, [22:01] you can skip steps. You can get away [22:03] with [ __ ] You know, you just have to [22:04] call in, show up, hey, I'm the you know, [22:08] >> Yep. sales person from, you know, blah [22:10] blah blah. And you know, away you go. [22:13] You know, like right now, I think with [22:15] OpenAI and Anthropic and so forth, it's [22:17] like that. It's like everybody wants to [22:19] buy AI. They're already predisposed to [22:20] buy. [22:22] Very, very different than who the hell [22:23] are you? Oh, we're PTC. I've never heard [22:25] of PTC. Okay. [22:27] Like now I'm in the door. [22:28] Why should I buy this? [22:30] I can't get it to work. Well, like let [22:32] me walk you through how it's going to [22:33] work. Like these kinds of things. Yeah, [22:35] that's invaluable if you have that. [22:36] Actually, so the Ron Gabrisko who's kind [22:39] of the original head of sales at [22:40] Databricks, [22:42] we got him. I had never heard like I had [22:45] never heard of the company who he was at [22:46] which was a public company. Imagine that [22:47] a tech sales guy that I had never heard [22:49] of his company. [22:51] And the company [22:53] was literally selling FTP. Okay. But [22:55] secure FTP. [22:56] >> Okay. Like think about how good at [22:58] selling you have to be to make your [23:00] number as a public company selling that. [23:02] Yep. And so this guy like obviously had [23:07] the discipline forced upon him and he [23:09] was extremely smart and that [23:10] combination, you know, I'll take that [23:12] all day. You know, if you've got that. [23:14] And so you'd rather have [23:17] you know, a successful company is fine [23:18] but some kind of playbook that was [23:21] harder to write, some product that was [23:23] harder to build. And that's another big [23:24] one is um [23:26] can you run a playbook or you somebody [23:28] who like joined VMware when it was on [23:31] fire and got a big position but you ran [23:33] the playbook that was set up for you? [23:36] Or are you the person who wrote the [23:38] playbook, who figured out how to sell [23:39] this very complicated piece of software, [23:41] who figured out how to lock lock out the [23:43] competition, to train the sales force, [23:45] to discipline them, to do all that kind [23:47] of thing? [23:48] That's a much harder find. And you know, [23:51] depending on the complexity like if [23:52] you've got an easy product, then [23:55] that that's one kind of thing. If you've [23:57] got a hard product, that's another. Some [23:59] of my takeaways were I was the first [24:02] basically BDR [24:04] and work and spent 10 years. [24:06] It was [24:08] in a lot of ways contrarian to the way [24:10] people thought about selling. Yeah. [24:12] Yeah. We sold an application, we sold it [24:13] one way and then we moved into the [24:15] platform business, totally changed the [24:16] way we sold. [24:18] Very disciplined on both sides and very [24:21] process oriented, like really managed [24:23] the process tightly. Yeah. So we're very [24:25] good at that and just very tight on the [24:27] profile of sales rep. Yeah. And The [24:30] profile fits very very well. The [24:32] profile. By the way, that's when I [24:34] interview sales guys, I always ask them [24:37] what's the profile of your rep. [24:39] And it's amazing to me that guys who are [24:43] very senior in very big jobs [24:46] have sometimes very loose profiles. [24:48] Whereas the ones who really have to [24:50] compete, it's extremely tight. What [24:53] they're looking for is so specific. [24:55] Uh [24:56] and you know, often surprising. One of [24:59] the things we just sticking on sales for [25:00] a sec. One of the things we got right [25:02] got a lot wrong at HubSpot. One of the [25:03] things we got right was the process to [25:07] interview a rep. And what we found out [25:10] was reps who were good learners did well [25:13] inside of HubSpot. And so, we got lots [25:15] of resumes. We like people on their [25:17] second sales job. Not their fifth, not [25:19] their first, their second so they'd done [25:21] something. [25:23] And if they had gone to a half-decent [25:25] school, not Harvard, not MIT, state [25:27] school State school, be average. And [25:29] they Yeah, and if they had been an [25:30] athlete if they could fog a mirror and [25:32] they did those things, they'd come in [25:33] and we didn't overthink it. [25:35] We came in for a half hour and the half [25:37] hour was, "Ben, welcome." Yeah. And I [25:40] would give you a scenario Yeah. and I [25:42] would be the customer and I would say, [25:44] "Sell me HubSpot." And I'd give you 12 [25:46] minutes to sell me like literally watch [25:47] 12. [25:48] I'd say, "That's very good, Ben. Here's [25:50] my feedback." Couple minutes feedback. [25:52] "Why don't you think about it [25:54] and let's do it again." [25:55] And if the person internalize that [25:57] feedback and [clears throat] sold it [25:59] better the second time 99% of the time [26:02] we hired them. Oh, that's interesting. [26:03] >> Yeah, I thought that was pretty good. [26:04] And it scaled really well. Yeah, yeah, [26:07] yeah. Right. Can they How good at they [26:10] are they at listening? This is [26:12] By the way, that's the other I think [26:13] mistake people make. [26:15] They look for somebody who's good at [26:16] talking. You really want somebody who's [26:18] good at listening. Yeah. [26:19] Um what So, important subtle difference. [26:23] Yes. [26:23] Okay, while we're on this type of thing, [26:25] you were the recipient of maybe my [26:27] favorite email in the history of emails. [26:29] May I read it to you? [26:30] >> uh sure, sure. [26:32] And the background of this was you had a [26:33] big product launch coming. You were [26:35] excited about it. You had a press tour [26:37] coming up in a couple weeks and Marc [26:39] Andreessen [26:40] >> Yeah. [26:41] front ran it and you sent him an email, [26:44] "I guess we're not going to wait until [26:45] the fifth to launch the product, Ben." [26:47] And the response to Ben Horowitz from [26:49] Marc Andreessen, "Apparently, you don't [26:51] understand how serious this situation [26:53] is. We're getting killed, killed, killed [26:55] out there. Our current product is [26:57] radically worse than the competition. We [26:59] had nothing to say for months. As a [27:00] result, we've lost over 3 billion in [27:02] market cap. We're now in danger of [27:04] losing the whole company, and it's the [27:06] server management's fault. [27:08] And then I love the ending. [27:11] Next time do the [ __ ] interview [27:12] yourself. [ __ ] off, Mark. [27:15] Yeah. [27:15] >> [laughter] [27:15] >> Yeah. Yeah. Yeah. [27:17] Are are we out of the [ __ ] off era? Uh [27:19] for Mark? Everyone. [27:21] Like, this is the emails that we get at [27:23] PTC. [27:25] Oh, yeah. And are we too soft now? You [27:27] know, Elon's not soft. [27:28] >> Nope. [27:29] And I think there's some of that. Like, [27:31] I don't think it's quite at PTC level. [27:33] So, in Cramer's interview with McMahon, [27:36] I think McMahon said to him, "What would [27:38] you do if I hit you in the face right [27:41] now?" [27:42] And I think Cramer's response was, [27:44] "Well, first of all, you better knock me [27:45] out." [27:47] And he And then McMahon says, "Well, [27:49] like, but what would you do?" He says, [27:50] "Is this a question? Are you testing my [27:53] intelligence or my courage?" [27:56] Good answer. [27:58] But like, you can [27:59] you can't ask somebody that in an [28:00] interview. My my first interview I [28:02] walked in with my suit on there and and [28:04] Harrison, who was the original head of [28:06] sales, said, "I wouldn't wear that suit [28:08] to a [ __ ] fight." [28:09] >> [laughter] [28:11] >> I think really good companies [28:13] the very, very, very, very best [28:15] companies tend to have founders and CEOs [28:18] who ask pretty aggressive questions. [28:20] Zuckerberg, Larry Page, those guys are [28:24] pretty who who have kind of gotten all [28:25] the way to the mountain top. They're [28:27] pretty blunt. And and I think look, I [28:29] think that's important in that one of [28:31] the most critical things in a company [28:35] uh [28:36] culturally is, you know, one, you give [28:39] direct feedback, and like, you can have [28:41] it out. Like, you know, like, Mark was [28:43] wrong on that feedback to me. Uh I was [28:45] right. But like, it's important that he [28:47] be able to say that and then it's [28:49] important that I be able to stand up to [28:50] it. Otherwise, [28:53] uh, the truth doesn't come out. Like, [28:55] you've got to like if you're running [28:56] away from the truth to preserve [28:58] feelings, that's a very dangerous thing [29:00] in a tech company. And the kind of [29:02] corollary to that is it's really [29:04] important that like bad news travels [29:06] fast. That, you know, if something's [29:08] wrong, that as CEO you find out about [29:11] it. And so you need that bluntness. Uh, [29:14] Andy Grove used to call it uh, [29:16] constructive confrontation. [29:17] >> Mhm. And he was By the way, that's [29:19] another one. [29:21] Where, uh, one of my favorite Andy Grove [29:23] anecdotes was, um, [29:25] somebody was late to a a meeting, you [29:28] know, and then this is when Intel was a [29:29] monster and Andy was God and all that [29:31] kind of thing. And they come in late to [29:33] the meeting. [29:34] And he he just looks at them and he [29:36] goes, "All I have in this life is time [29:40] and you're [ __ ] wasting it." [29:43] You know, which is like the meanest [29:44] thing you could ever say to somebody. [29:46] But, particularly as a company grows, [29:48] you need to reset the culture like if [29:50] it's starting to fray at the edges. You [29:52] can't just let that go. [29:54] And by him saying that, you know, it [29:56] might crush that person's feelings, but [29:59] everybody's telling that story to the [30:00] point where I heard it. I didn't work [30:01] for Intel, right? And that that's a [30:04] culture setter. Like, we're not [ __ ] [30:05] late to meetings here. Like, that's not [30:07] what we do. And and that's Look, not [30:09] every company has that culture, but in [30:12] if you have that culture, you need to to [30:13] maintain it. Okay, speaking of that, I [30:16] coach all these CEOs. Well, one thing [30:19] I've noticed is Paul Graham wrote that [30:20] founder mode memo. It's It strikes me as [30:23] relatively standard operating procedure [30:25] now. It's really Well, is that your [30:28] reaction, too? Well, yes, although [30:29] there's a part that's wrong to it. Or [30:31] there's a part that I I would say is a [30:33] little misleading to it. You know, and I [30:34] think it came originally from Brian [30:36] Chesky. [30:37] >> And so Brian, [30:39] like I said, there's a part that's very [30:41] right about it, which is um what [30:43] happened to Brian is he hired a like [30:44] extremely senior people. [30:46] >> Yeah. Uh and then he did the thing that, [30:48] you know, we talked earlier, which he [30:50] overly deferred. And then that created [30:54] fiefdoms, politics, um all kinds of like [30:57] weird stuff. And then he kind of after [31:00] COVID took the company back by going [31:02] into quick founder mode. And this is [31:04] like I'm being much more dictatorial. [31:06] And I think that that part is all [31:07] correct. I think the danger with the [31:10] idea is [31:11] people are taking it to the point where [31:13] they're going, "Well, I don't want to [31:14] hire any senior people." [31:15] >> Yeah. [31:16] I see that. It's like, "Well, okay. So, [31:19] you're going to go compete [31:22] with and you need a worldwide sales [31:23] organization, and you're going to try [31:25] and grow a [ __ ] from scratch to [31:26] do that. Well, let me tell you all the [31:28] things that that person doesn't know [31:30] that they're going to have to learn on [31:31] your nickel, but you could just buy [31:33] today. What's your profile? How do you [31:35] split territories? Like how do you open [31:37] up international? How do you like [31:39] there's just like years and years of [31:41] experience and relationships that are [31:43] required to do that right? And so, [31:45] because you're in founder mode, [31:47] you're so [ __ ] afraid to do that. [31:49] It's like, "No, you need to be able to [31:51] hire that person, too, when you need [31:53] them, but you need to be able to manage [31:55] them." And that's very different than [31:57] avoid, avoid, avoid. [31:59] And I think people have taken what Paul [32:01] wrote, and it's like, "Oh, no, like no [32:03] no no experience people. Like screw that [32:06] and so forth." And I, you know, [32:07] particularly, you know, if you're an [32:09] enterprise company, I think that [32:10] definitely doesn't work. Like even on a [32:12] consumer company, it's going to be [32:14] shaky, you know, like positions like CFO [32:16] and so forth. Like outside knowledge is [32:18] just valuable. You have to understand [32:20] enough about that, [32:22] you know, in founder mode, you've got to [32:24] learn enough about that job that you [32:25] feel confident managing that person and [32:28] telling them what to do, uh and not [32:31] having them tell you what to do, [32:33] because that's that's when you lose the [32:35] company. So, [32:37] I think it's good. It's a good It's like [32:39] an overcorrection from from where things [32:41] were. [32:41] >> I think you're By the way, I think [32:43] you're spot-on on that. [32:44] One of my favorite CEOs is Jensen Huang, [32:47] and he's got a unique playbook. He's got [32:49] 60 direct reports, he gives feedback in [32:51] public, and everybody knows the story. [32:54] The interesting thing about the CEOs I [32:55] coach, none of them really do that. They [32:57] don't have 60 direct reports. They They [32:59] haven't followed his playbook. I kind of [33:01] scratch my head at [33:02] uh why [33:02] >> also haven't followed Elon's playbook, [33:04] right? [33:04] >> Exactly. No one uses the algorithm [33:06] outside of Elon's companies. I don't get [33:08] it. Have you You notice the same thing? [33:10] So, most of the companies you recruit [33:12] out of don't run like that. Um and so, [33:15] they don't think of it that way. And [33:16] then also, I think that to run it like [33:18] Jensen does, by the way, you know, [33:20] that's a little bit like I I'd say [33:22] closer to how [33:23] I run Andreessen Horowitz is more like [33:26] how Jensen operates. [33:29] But you got to like [33:31] the I think what founders are lacking is [33:33] the level of confidence that you have to [33:35] have to do that, because you have to be [33:37] able to say [33:40] if you're reporting to me, [33:43] you got to be like basically [33:47] CEO caliber. Um because I'm not [33:50] >> I'm not developing you. Um which is [33:52] something that I highly believe in. CEOs [33:54] can't really develop executives. They [33:56] either can do it or they can't. [33:58] >> I agree with you on that. [33:59] And then you have to have feel like [34:02] you've got enough knowledge just be able [34:04] to like walk in and understand what's [34:05] going on and so forth, and and kind of [34:07] be able to [34:09] evaluate uh how the company's going from [34:12] you know, at that level. You know, Elon [34:15] is the most competent and has the most [34:17] confidence of anyone, and you know, [34:18] Jensen is kind of at that caliber. I [34:20] think that a lot of people, you know, [34:23] need to develop that as they go. I would [34:25] say like when I [34:26] observe Zuckerberg, he didn't have that [34:28] the whole way. He's kind of [34:31] over time getting more like that, but [34:33] you know, like he deferred like half the [34:36] company to Sheryl for a while until he [34:38] could kind of build his confidence over [34:40] there. And and I think that's a little [34:41] more [34:43] the normal path. It's hard to go from [34:45] zero to Jensen. Yeah. You know, like I [34:47] mean [34:50] you know, it's interesting Jensen's [34:52] been doing it now for 30 years. [34:54] >> Yeah, 30 plus years. So, you know, what [34:56] was he like four years in? [34:58] >> I suspect he wasn't quite at this level [35:00] of master of the universe. Mhm. What can [35:02] the the CEOs listening And Elon, of [35:05] course, got fired early. Like you do [35:07] like there is a learning curve to the [35:08] job even for the best. What can CEOs [35:11] learn from Zuckerberg? You worked with [35:13] him pretty closely here. Well, I think [35:14] Zuck he's very, very, very good at [35:17] operating from [35:20] kind of first principles thinking, not [35:21] being overly influenced by one anybody [35:24] else's ideas or just like the way things [35:27] are. Like he he's very, very good at [35:29] just looking at it. And then also you [35:31] know, they were amazingly disciplined at [35:33] looking at things through a data lens. [35:36] Like, okay, what does the data say and [35:38] do that and you you know, that's how [35:40] they were able to grow it so fast, [35:43] overcome the competition and and these [35:45] kinds of things. And he he definitely [35:47] stays like extremely curious, which I [35:50] think all the [35:51] all the great CEOs are like very just [35:53] interested in everything all the time. [35:55] You know, I think people underestimate [35:57] him and Elon and Jensen and so forth on [35:59] their like oh, those guys are nerds. The [36:01] the the their [36:03] people skills are astoundingly good. And [36:05] do you think they always were? [36:06] Zuckerberg struck me as that not being [36:08] the case early. He was so introverted [36:12] that you couldn't see it, but I I felt [36:14] like it was going on inside his head. [36:16] You know, if you look at like the M&A [36:17] deals he's done he's he's like a really [36:20] outstanding psychologist. And I I think [36:23] that [36:24] he always had some of that in it. You [36:25] know, his mom's uh [36:27] in that profession and she's she's very [36:29] smart about it, Karen. I think it was [36:31] always in there um it but he needed the [36:33] confidence to get it out. I mean, he [36:35] started that company when he was like a [36:37] little kid. [36:38] >> Yeah. [36:39] You wrote a whole book about culture. [36:41] What are people getting wrong? [36:43] >> [laughter] [36:44] >> I think people don't know what it is. [36:45] Like I mean, that's the main thing. [36:47] The main thing that particularly [36:49] founders don't know, which is why I [36:51] wrote the book. Although, it's funny the [36:53] people who really like that book were [36:54] like Ted Sarandos, you know, like and I [36:56] realized after I wrote it [36:59] you really don't have the cultural issue [37:01] till you get big. And so, at the startup [37:04] phase [37:05] you you you may be sowing the seeds of [37:08] your own cultural like problems, but [37:12] there are no cultural issues in the [37:13] beginning because [37:15] the thing is small, you're saying it, [37:17] you're kind of managing the culture by [37:19] hand [37:21] unconsciously. [37:23] So, the big thing that people people [37:25] think that culture is values. Um they [37:27] think, "Oh, it's, you know, like we have [37:29] a culture of integrity or we have a [37:30] culture of, you know, whatever." [37:32] >> same. Everyone's got the same ones. [37:33] >> Yeah, we do we have each other's backs [37:35] or like what whatever whatever it is. [37:38] And those things aren't really anything. [37:40] They're just platitudes. The actual [37:42] thing is behaviors. And so, [37:46] when you think about your culture, you [37:47] kind of want to think about like what [37:49] are the behaviors that put you in a [37:51] place [37:52] where you're the kind of company that [37:53] you want to be and give you the [37:54] advantage that you want to have. Okay, [37:57] we're in venture capital. [38:00] What does everybody in venture Well, we [38:01] really love entrepreneurs. Like [38:02] everybody in venture capital [ __ ] [38:04] loves entrepreneurs, but then you get [38:06] down to the way entrepreneurs talk about [38:09] a lot of VCs and they're like, "These [38:11] guys are [ __ ] arrogant. They're [38:12] [ __ ] They talk down to me this and [38:14] that." Well, like well, if you want to [38:16] be this, why are you that? [38:18] And it gets down to the behaviors. Are [38:20] you on time for a pitch meeting? Are you [38:22] on your phone during pitch meeting? Do [38:23] you get back to the entrepreneur if [38:25] you're not going to invest in them? Like [38:27] these behaviors end up setting the [38:30] culture whether you're like [38:33] care about entrepreneurs, have respect [38:34] for them, or you think you're above [38:36] them. [38:37] And it doesn't have anything to do with [38:39] what you said, it has to do with what [38:40] you do. [38:42] Uh which is why I called the book what [38:43] you would do is who you are. [38:45] But it's [38:46] that's the really the core thing. Um but [38:49] it takes a lot of thought to say [38:52] okay, if I want to be this, how must I [38:54] behave to get there? And you know, you [38:56] can say like, oh, treat the company's [38:59] money like it's your own. Okay, great, [39:01] but what does that mean? Well, where are [39:04] you staying? What hotel? You know, how [39:07] are you traveling? What's your thing? [39:08] And like so if you want that, then that [39:11] has to be systematic. Let me ask you [39:13] about [39:14] >> Now, you may not want that. You know. [39:15] There's one cultural gotcha that I see a [39:18] lot [39:19] where there's a brilliant, brilliant [39:23] 100x engineer in the company that's an [39:25] [ __ ] [39:26] Yeah, yeah, yeah. Yeah. [39:29] Not sometimes. But by the way, venture [39:31] capital is more like that [39:33] >> [laughter] [39:33] >> than engineering organizations. There's [39:35] more [39:36] of those. Yes. [39:37] Well, like I mean and and I think that [39:41] on an engineering team, you kind of have [39:43] to have the parameters of okay, like [39:45] what does [ __ ] mean? If [ __ ] means [39:47] that in the code review I don't say [39:48] anything and then I go in the middle of [39:50] the night and rewrite your code, that's [39:52] going to be tricky as you grow. Like [39:54] that that that's hard to manage. If [39:55] [ __ ] is I expect like a super high [39:59] standard, that's another thing. And so [40:01] you kind of want to define like, okay, [40:04] what is it that we're not going to do [40:05] here? And the thing about engineers is [40:08] they're like amazing at following rules. [40:10] So if you make clear like what the [40:13] parameters are on it. And I I find and [40:15] in venture capital, too. Like like we [40:16] have that that that's a venture capital [40:18] problem if I ever heard one. You know, [40:20] you get a lot of very smart spiky [40:23] personalities. And you know, Mark and I [40:24] talk about this sometimes. It's like [40:26] well, was Steve Jobs so mean to people [40:30] because that just goes with being so [40:32] brilliant or because he could get away [40:35] with it because he was so brilliant, [40:37] right? Like [40:37] >> you come out? Um Well, I've I've had the [40:39] same debate. Yeah, so I think it's a [40:42] little bit more the latter. And so I [40:45] think that if you're running an [40:46] organization Wait, which one is the [40:48] latter? I forgot. Um that that he could [40:50] get away with it. Right? Like he didn't [40:52] have to do that. Mhm. Like but he could [40:55] do that. And you know, like it's his [40:56] company. He can do what he wants. I [40:58] think that the problem with founders [41:00] modeling themselves after [41:02] Jobs. I mean, you know, to some extent [41:04] after Elon is well, if you're not Jobs [41:06] or Elon, maybe you can't get away with [41:08] that. And like maybe people just walk [41:10] out the damn door in a way that they [41:12] won't with those guys. And it's very [41:14] hard to have like the highest performing [41:17] talent without like them coming with [41:19] some of those behaviors. Uh you know, [41:21] and it doesn't matter like in [41:22] engineering and BC and whatever. [41:24] And so you kind of have to be very [41:27] specific about okay, [41:29] we're not going to have this, [41:30] but we'll have that. You know, one of [41:32] the things that I've outlawed at the [41:34] firm, which a lot of you know, kind of [41:37] people of this ilk would do is like [41:38] look, you can't make yourself look smart [41:41] by making somebody else look dumb. Like [41:43] that doesn't that [ __ ] doesn't count [41:45] here. Um if you do it by the way with an [41:47] entrepreneur, like if you get on Twitter [41:49] and say, "Oh, [41:50] that business sells dollars for 85 [41:52] cents. Ha ha ha, I'm so smart." [ __ ] [41:54] you, you're fired. Like I'm not dealing [41:56] with that at all because [41:58] that's just like not who we're going to [42:00] be. We love that you're smart. You can [42:03] be as smart as you want to be. Like [42:04] that's fine. You don't have to get there [42:06] through that method. And then once [42:07] people know that, [42:08] they're fine like not doing that. But I [42:11] couldn't say you think it'd be hard to [42:13] say, "Just don't be an asshole." Mhm. [42:16] Because like sometimes, [42:18] you know, the smart like they're just [42:19] like, "I'm not going to suffer through [42:21] this dumbass conversation." Like, you [42:23] know, there's people who are extremely [42:25] smart are are going to do that. [42:28] And it can't be like, "Oh, no, you have [42:29] to suffer through every dumb [42:30] conversation." Like, that's not going to [42:32] work. Okay, but there's Ben Horowitz [42:34] isn't like, "Don't tolerate it. Zero [42:36] tolerance for this thing." It's No, I [42:38] think that no [ __ ] rule was never [42:40] going to work. [42:40] >> Yeah, yeah, yeah. So, what is it that [42:42] you don't want them to do? [42:43] >> [laughter] [42:44] >> Yeah. Like, what's over the line and [42:46] what's not over the line? And like I [42:47] think [42:48] even like very spiky people can live in [42:51] that kind of context. [42:51] >> He's very spiky. Yeah. Yeah. [42:54] What percentage of I like you brought [42:55] this up like um in another pod that I [42:58] wanted to follow up on. [42:59] Like, when I was CEO of Opsware, I I [43:02] didn't know what I was doing a lot of [43:03] time. I was confused a lot. And when you [43:05] were CEO, you felt the same way. Like, [43:06] what percentage of the time do you feel [43:07] like, "I really don't know what I'm [43:08] doing" versus "I kind of got a handle on [43:11] this thing"? And today, running [43:12] Andreessen Horowitz or through your [43:14] journey, like I found yours pretend like [43:17] they know what they're doing. Yeah, [43:18] well, everybody pretends. Um and this is [43:20] kind of part of the challenge. So, I [43:23] think it takes a while. I mean, like I [43:25] Now, like I had to grow up very fast. We [43:27] went public when we were 18 months old, [43:28] right? So, [43:31] >> That'll grow you up in a hurry. [43:33] But I I didn't really feel like I knew [43:35] what I was doing there probably till [43:41] 4 years into it. Um [43:43] you know, when I rebuilt the sales [43:44] force, I brought in Craney, all that [43:45] kind of thing. Maybe three and a half, 4 [43:47] years into it. [43:49] And I was never [43:52] as confident at that as I was as I am [43:55] now. And it it's different for different [43:57] people, but like it you need like enough [44:00] reps at it to have [44:02] like the more confident you are in your [44:04] judgment, the faster the decisions you [44:06] can make, the less you care about what [44:08] people think, the less you care about [44:10] making a mistake. And those are all the [44:13] things. That's why Jensen is so magical, [44:15] right? Like he sits in the room, he [44:17] talks to everybody, he knows exactly [44:20] what he wants. Same with Elon, right? [44:21] Like he can just sit there and go. I [44:23] guarantee you neither of them started [44:24] that way. [44:25] Uh [44:26] >> Yep. You you know, like you you build it [44:28] into that. [44:28] >> I see silly things on Twitter where [44:30] people say [44:32] venture capital is easier than [44:34] entrepreneurship or entrepreneurship is [44:36] easier than venture capital. People ask [44:38] me that. [44:38] >> Venture capital is easier. [44:40] What's he talking about? [44:41] >> Way easier. Yeah, I know. [44:44] Uh [44:44] >> Like that's not even close. Like who the [44:46] [ __ ] would think venture capital is [44:48] harder than entrepreneurship? [44:49] >> of people. I think the venture capital [44:51] there's a lot more luck involved. Like [44:53] if you join Andreessen Horowitz today, [44:56] you have an amazing platform or Sequoia, [44:58] amazing platform. And you may do three [45:00] deals, you know, maybe one turns into a [45:02] trillion-dollar company. There's a fair [45:04] amount of luck around that. Yeah. Yeah, [45:06] I I mean, I think that [45:07] >> Entrepreneurship doesn't have a lot of [45:09] luck. It has some luck. [45:10] >> It also a lot of bad luck. [45:11] >> Yeah. [45:12] >> [laughter] [45:13] >> You know, entrepreneurship [45:15] you have one shot, you have to make it [45:17] work. And then you really, really pay [45:19] for your mistakes much more directly. [45:21] And then the clock is ticking in a way [45:24] it's like [45:25] >> Yep. [45:27] You There are no quarters in venture [45:29] capital. So, like venture capital is [45:30] just kind of like a an easier kind of [45:33] business. Now, [45:35] look, there's a lot of people I'm saying [45:37] that as [45:38] you know, someone who succeeded in it. I [45:40] suppose if you failed in it, [45:42] it might look harder in a in a different [45:44] way. But I like I think that [45:47] the pressure level and the stress level [45:51] is not close because if you have a small [45:53] venture capital thing and it fails, it's [45:55] never a lot of people. Like you you can [45:58] get a tech company up to thousands of [46:00] people and then have them lay them all [46:02] the all off. Yes. Like that is common. [46:05] Yeah. And it's brutal. And then [46:08] the people that you're raising money for [46:11] have a much tighter eye on you because [46:15] it [46:15] you could have one funding source, [46:18] whereas in venture capital you always [46:19] have, you know, many funders. Mhm. [46:22] Very generally have many funders, yeah. [46:24] I appreciate you coming on the pod. [46:25] >> Yeah, no, it was fun. [46:26] >> Uh All right. Yeah, thank you very much. [46:29] I think all the CEOs who are watching [46:30] are going to really like it. Thank you. [46:31] All right, good good good. [46:33] Okay, I hope you liked that episode with [46:34] Ben. I really liked it, learned a lot. [46:37] Something I thought about while he was [46:38] talking is one of my bugs as CEO of [46:42] HubSpot was I'm pretty conflict-averse. [46:44] I think a lot of CEOs are, particularly [46:47] first-time founder CEOs. Andreessen [46:49] Horowitz and Sequoia back a lot of [46:52] first-time CEOs who haven't really [46:53] managed before, and it's just [46:56] uncomfortable. Confrontation is [46:57] uncomfortable, [46:58] unless you kind of grew up with it, [47:00] it's just not natural. Ben's got a good [47:03] term that I'm going to borrow. He calls [47:05] it constructive confrontation. [47:08] I like that. You need to have a [47:09] constructive level of confrontation with [47:11] most people inside of your organization. [47:14] I think kind of related to that, Ben [47:16] talks about decision debt. And we had [47:19] this at HubSpot. You had a VP of sales, [47:22] you know you need to fire them, but you [47:23] kick the can down the road hoping they [47:25] nail the next quarter. You know your [47:27] pricing model not really working and [47:28] scaling, but you kick the can down the [47:30] road a couple quarters to fix it. [47:32] There's all kinds of stuff kicking [47:33] around your head like that. And [47:37] you know, I think it's a lack of [47:39] confidence. I want to be a popular CEO. [47:41] I think that was another bug of mine [47:43] kind of related with that [47:44] conflict-averse thing. All of this also [47:46] rhymes, I think, with hiring. And [47:48] there's a lot of talk around founder [47:49] mode, and you know, people hiring and [47:52] deferring to people, and now they're [47:54] micromanaging. [47:56] I think when you're a a first-time [47:58] founder CEO and you're hiring a [48:00] been-there-done-that person that's more [48:02] senior than you, has done more stuff in [48:04] their career, [48:06] you're a little nervous about truly [48:08] managing them and you end up deferring [48:10] to them and that's where the problem [48:11] starts. [48:12] And so I think a lot of this idea around [48:15] constructive confrontation that Ben [48:17] talked about is really productive. And [48:19] if you're a little risk-averse like me, [48:22] if you're a little [48:23] you want to be popular like me, maybe [48:26] you need to be a little bit more [48:27] constructive in your confrontation. [48:29] The last [music] thing I would say that [48:31] he talked about and I agreed on is being [48:33] a CEO is pretty uncomfortable, [48:35] particularly from one of these [48:36] hypergrowth CEO companies today. They're [48:38] growing so fast, everything's breaking, [48:39] everything's changing. [48:41] I think it's just fine [48:43] if in your head you think you don't know [48:44] what you're doing because Ben didn't [48:45] think he knew what he was doing when he [48:46] was running Loudcloud. And I didn't [48:48] think I knew what I was doing when I was [48:49] running HubSpot. So if you're feeling [48:51] that as a CEO, [48:53] I'm here for you. [48:55] Hope you liked it. Let's keep the convo [48:56] going. I'm @bhalligan on X. See you over [48:59] there.