# Surviving Twitter's Growing Pains: Ex-CEO Dick Costolo

Podcast: Long Strange Trip: CEO to CEO with Brian Halligan
Published: May 30, 2026
Reading time: 23 min
Canonical: https://podbrew.app/briefs/long-strange-trip-ceo-to-ceo-with-brian-halligan-surviving-twitter-s-growing-pai

This Podbrew episode features Dick Costolo, who served as CEO of Twitter during its most chaotic period of hypergrowth. He details his five-year journey transforming the "drama queen" startup into a public company.

The discussion covers his unique leadership playbook, including how he shifted decision-making from slow group consensus to a "bias to yes" approach, streamlined processes with DRIs, and gathered ground-level insights by actively engaging with engineering teams. Costolo also shares candid reflections on missed opportunities, such as the failed Instagram acquisition, and the personal struggles of making tough personnel decisions.

This conversation offers invaluable lessons for any leader navigating rapid organizational expansion. It provides a practical guide for managing the complexities of scaling past 150 people, offering insights into fostering accountability, accelerating decision-making, and maintaining agility amidst intense growth.

## Key takeaways

- Prioritize "velocity, velocity, velocity" as a core principle to prevent companies from slowing down during periods of rapid growth.

- Decentralize decision-making by pushing authority down the organizational chart, eliminating group-based voting, and empowering individuals to solve problems independently.

- Cultivate a culture of accountability by removing vague corporate platitudes and addressing seemingly minor operational sloppiness as symptomatic of larger systemic issues.

- A 'bias to yes' policy empowers teams to launch initiatives with only direct manager approval, limiting veto power exclusively to managers or critical functions like legal/trust & safety, which significantly accelerates experimentation.

- Leadership's primary responsibility is to correct mistakes that happen, not to prevent them from occurring.

- Employ direct, unfiltered conversations with individual contributors to gain genuine insights into operations, bypassing managerial filters.

- The prevalence of "two-way door" (reversible) decisions allows companies to do more quickly, balancing the need for focus with agile experimentation.

- Subtle leadership actions, such as visible prioritization of late-night work, can effectively change company culture.

- Leaders should transition from day-to-day tactical "firefighting" to a strategic "forestry management" mindset.

- Strategic leadership involves mapping the organizational territory and planning for future scenarios over 24 months to prevent problems, rather than just reacting to current issues.

- To ensure clarity and impact when giving difficult feedback, write down your exact message beforehand and commit to saying only that, avoiding extraneous softening language.

- After delivering tough feedback, embrace the silence that follows, allowing the recipient to absorb the information without further interjection or dilution of the message.

- Prioritizing internal promotions for individuals like Kevin Weil created clear career progression paths, ensuring employees felt their growth wouldn't be capped by external hiring.

- Hypergrowth, especially in AI, can lead companies to neglect operating leverage and efficiency when they raise significant capital.

- Excessive funding can create a false sense of security, causing leadership to take their 'eye off the ball' regarding burn rate and capital efficiency.

- Maintaining high hiring standards is difficult in hypergrowth; implement strict performance management, like preventing low performers from transferring teams, to ensure accountability.

- Twitter offered Instagram around $700 million in stock, representing over 10% of its $5 billion valuation, in an unsuccessful acquisition attempt.

- Dick Costolo considered Facebook's acquisition of Instagram a "checkmate" move that strategically boxed Twitter out of the future of rich media and video social feeds.

- Unconventional experiences, such as performing comedy or handling high-pressure live events, can build crucial skills like public speaking and composure that benefit future CEOs.

- Remaining private longer allows companies to prioritize long-term strategic objectives and avoid the stress and short-term focus imposed by public market pressures and daily stock performance.

## 02:00 - 08:01 Dick Costolo Recalls Twitter's Chaotic Early Days and His Rocky Ascent to CEO

Dick Costolo joined Twitter as COO in summer 2009, initially approached to cover Ev Williams' paternity leave. Having just sold FeedBurner to Google and planning a new venture, Costolo decided to join what he called a "rocket ship" despite Twitter famously having zero revenue or a business model at the time, a fact often highlighted in media articles.

Twitter's early environment was known for being dysfunctional and chaotic. Decisions, such as implementing a native retweet function, were made collectively by the group rather than by individual department leads, which led to a slow, methodical pace for development and decision-making.

The process of Costolo transitioning to CEO, replacing Ev Williams, was described as "awful" and drawn-out. He received conflicting messages from the board over many days and weeks, almost quitting several times before finally agreeing to take the role.

Upon becoming CEO, Costolo navigated a complex leadership structure where co-founders remained highly involved; Jack Dorsey was still the chairman of the board, Ev Williams remained on the board, and Biz Stone and Jason Goldman were still working within the company.

> Man, you don't get an opportunity to go into these, to get on these rocket ships, and when you get a-- get the opportunity, you should do it.

## 08:01 - 12:01 Driving Velocity by Eliminating Groupthink and Accelerating Decisions

Dick Costolo's immediate priority upon becoming CEO was to drastically increase Twitter's operational velocity. He constantly pushed teams to accelerate, questioning why tasks took so long and challenging them to imagine how a six-week project could be completed in two weeks. This relentless pursuit of speed aimed to counter the inherent slowdown often seen in hypergrowth companies.

A key shift involved decentralizing decision-making. Costolo eliminated the practice of group-based voting, instead empowering employees to "figure it out" themselves and pushing authority down the organizational hierarchy. This meant individuals were expected to make choices without constant top-down approval, fostering quicker execution.

Costolo also cleared out cultural clutter that impeded progress. He removed meaningless corporate operating principles, which he felt were vague and unhelpful, often even "weaponized against management." Furthermore, he addressed a general lack of accountability, famously linking dirty dishes in the office kitchen to broader operational failures like site crashes, and discarding complacent slogans like "We'll make better mistakes next time."

These changes were designed to instill a culture of precision and rapid execution, ensuring that despite growing larger, the company would actually get more done rather than less. The goal was to combat the tendency for companies to slow down as they gain size and complexity.

> We're not gonna make decisions as a group, we're gonna push decisions down the stack.

## 12:01 - 14:02 Dick Costolo explains decentralizing decision-making to combat the 'Dick Said' problem

Dick Costolo observed a pervasive issue he dubbed the 'Dick Said' problem, where managers would deflect accountability by telling engineers 'Dick said to do it' when pushed back on decisions. This undermined team autonomy and led to decisions being made without proper defense or understanding.

Costolo recalls an instance where the Android app's boot time increased, causing usage numbers to drop. An Android engineer approached him asking if he had ordered the removal of a JSON file from the boot system, as he had been told. Costolo, who never issued such a directive, realized this was a clear example of managers misattributing commands to avoid defending their own choices.

To counter this, Costolo implemented a strategy to push decision-making authority down the organizational stack. Teams were no longer allowed to cite a higher authority like 'Dick said' as the sole justification. Instead, engineers and their teams were required to be able to defend their decisions to their managers, fostering greater ownership and accountability for outcomes.

This shift aimed to empower individual teams to take responsibility for their choices and understand the rationale behind them, rather than blindly following mandates. It also helped speed up the organization by ensuring decisions were debated and defended at the appropriate level, preventing bottlenecks and misunderstandings.

> It's push the decisions down the stack. And by the way, if your team makes a decision and you can't defend it to your manager, like that's, don't go, 'Well, so-and-so said.'

## 14:02 - 18:03 Implementing a 'Bias to Yes' Policy to Speed Up Innovation

Organizations often face a problem where new ideas or experiments get stalled, not because they are explicitly rejected, but because teams are told to seek approval from numerous departments like security or legal. This creates internal 'fiefdoms' and a slow, bureaucratic process where initiatives languish in a never-ending cycle of permissions.

To combat this, Dick Costolo implemented a 'bias to yes' policy. If an engineer had an idea for an experiment and their direct manager approved it, they could proceed. Veto power was strictly limited to the direct manager, or legal/trust & safety if there were compliance or legal concerns. No other department or group was allowed to block or demand additional approvals.

This policy dramatically accelerated the launch of experiments. Engineers were empowered to quickly test ideas, even with minimal design, for small percentages of users, rather than getting bogged down in extensive cross-departmental reviews. It shifted the focus from managing complex processes to enabling outcomes.

The 'bias to yes' approach counters the common tendency in organizations to add layers of process in response to past failures, similar to Google's famously long launch checklists. Such over-processing can lead to managing the steps rather than the desired results, hindering agility and innovation. The emphasis should be on Directly Responsible Individuals (DRIs) who own the outcome.

> No other organization, period, is allowed to tell you you can't do that or you need to go ask these people for permission. Just your direct manager.

## 18:03 - 20:03 Leadership's role is to correct mistakes, not prevent them

Empowering teams involves pushing decision-making down the organizational stack and minimizing excessive processes. This approach fosters a bias to action, encouraging individuals to take risks and be bold without constantly seeking permission.

A crucial element of this philosophy is creating an environment where mistakes are not punished. Instead, leadership's responsibility shifts from trying to prevent errors to actively helping correct them when they occur, promoting open communication for quick resolution.

This culture supports innovation and rapid iteration, as the fear of reprimand does not stifle proactive problem-solving and experimentation. It allows for quick learning and adaptation within an organization.

> It's not the job of leadership to prevent mistakes from happening. It's the job of leadership to correct mistakes. So if you screw something up, like, by all means, tell us so we can help you fix it, but no one should get in trouble for screwing something up or making a mistake.

## 20:03 - 24:04 Scaling Communication by Providing Context and Leveraging Unfiltered Feedback

Effective communication in a growing company requires ensuring every employee understands not only their tasks but also the overarching priorities and how their work contributes to the company's success. This involves providing clear context for decisions and explaining the personal and professional implications of achieving company goals. The example of a Tesla factory worker understanding the broader impact of their specific task illustrates this depth of understanding.

Leaders should prioritize the swift correction of mistakes rather than attempting to prevent all errors. This necessitates fostering an environment where issues are communicated quickly up the hierarchy. Regular, repetitive communication of core priorities, how success is measured, and why these goals are crucial for the company, reinforces understanding and alignment across all teams.

A tactic inspired by Steve Jobs involves a leader directly engaging with individual contributors, bypassing their immediate managers, to gain unfiltered insights. When managing both Pixar and Apple, Jobs would dedicate a day at Pixar to meet directly with staff like illustrators, asking them what was working well and what issues they faced, without their director present. This direct approach allowed him to quickly identify problems and successes from the ground level.

> It's not the job of leadership to prevent mistakes from happening, it's the job of leadership to help correct them quickly when they happen.

## 24:04 - 28:05 How CEOs Balance Focus with Rapid, Reversible Decisions

Leaders often struggle to maintain priorities set at the beginning of the year, frequently getting sidetracked by new opportunities. This constant "rejiggering" of priorities can demotivate teams; employees may become reluctant to invest fully in tasks if there's a high chance they'll be abandoned soon after. This highlights a common pitfall where a lack of consistent direction slows down execution.

The discussion delves into how different tech leaders approach this challenge. Steve Jobs famously advocated for extreme focus, seeing a CEO's role as saying no to almost everything. In contrast, Jeff Bezos embraced doing "everything," requiring his team to talk him out of ideas. Both approaches have led to significant success, demonstrating that there isn't one singular path to effective leadership.

The rise of "two-way door" decisions in software, where changes are quickly reversible, means companies can now pursue more initiatives in parallel. While focus remains crucial for long-term vision, this agility allows for rapid experimentation. The ability to quickly pivot or revert from non-existential decisions enables organizations to explore a broader range of opportunities without the deep commitment previously required for "one-way door" decisions.

> You know, there's lots of ways to be successful.

## 28:05 - 30:05 Shifting Twitter's Culture with Late-Night Management by Walking Around

Dick Costolo, inspired by Bill Campbell, observed that Twitter's early culture lacked urgency; most employees left by 5:30 PM. Campbell famously quipped that a grenade rolled into the office at that time would "only take out the cleaning people," highlighting the absence of late-night dedication among the staff.

Recognizing that simply telling people to work harder would be ineffective, Costolo implemented a subtle strategy he called "management by walking around." He would leave for dinner and return to the office around 9:00 PM or 9:30 PM to walk through the workspaces.

During these late-night tours, Costolo would engage with employees who were still working, discussing their ongoing projects. Crucially, he would then publicly acknowledge and prioritize the work of these dedicated individuals, like Marcel Molina, at subsequent all-hands meetings.

This indirect method slowly but effectively changed the company culture. Employees noticed that those who worked late and interacted with Costolo received greater visibility and prioritization for their projects, subtly incentivizing a shift towards increased commitment and late-night productivity.

> You could, roll a grenade into Twitter at five thirty PM and only take out the cleaning people.

## 30:05 - 32:06 Embracing "forestry management" for strategic leadership over tactical "firefighting"

Many directors tend to focus on immediate, tactical problems, often described as "firefighting." This approach, while addressing urgent issues, prevents them from engaging in the long-term strategic planning necessary for a company's sustained growth and resilience.

Dick Costolo introduced the metaphor of "forestry management" to encourage directors to shift their mindset. Instead of just putting out current fires, leaders should map the territory and proactively plan for future scenarios. This means thinking about what needs to be true 24 months from now to prevent potential problems, like ensuring a highway isn't threatened by a future forest fire.

The core difference lies between tactics and strategy. Tactics involve immediate actions, like "chopping down trees" or "stamping out fires." Strategic leadership, however, requires a holistic view of the entire organization, ensuring the whole "territory" is in better shape in the long run. As a company scales, leaders cannot personally handle every immediate issue.

To scale effectively, leaders must delegate the tactical "firefighting" to their teams. This allows directors to concentrate on the bigger picture: comprehensive planning, proactive problem prevention, and shaping the company's future trajectory, ensuring long-term health rather than just crisis management.

> Your job is to map the territory and start to do forestry management. Like, what are we gonna do so that next year, if there's a fire over here, that highway isn't gonna be in trouble?

## 32:06 - 36:06 Strategies for Delivering Direct Feedback

Dick Costolo highlights a common struggle for leaders, particularly those new to management or operating in environments like Silicon Valley, which often defaults to passive aggressiveness: delivering direct, difficult feedback. Many confuse being straightforward with being a "jerk," believing that tough conversations require a lack of empathy. However, Costolo asserts that it's possible to be both empathetic and direct, emphasizing that avoiding candor harms performance and accountability.

A key piece of advice for navigating these uncomfortable conversations, originally from Bill Campbell, is to prepare diligently. Leaders should write down precisely what they intend to say, especially for performance reviews or project cancellations. The challenge lies in sticking to this prepared statement, as most people, when faced with the actual conversation, tend to soften their message with unnecessary fluff, undermining the clarity and impact of the feedback.

Another crucial technique is to "sit with the silence." After delivering difficult news or feedback, resist the urge to fill the ensuing silence with more explanations or apologies. This silence allows the recipient to process the information without interruption, and it prevents the giver from backtracking or diluting the message. Costolo recalls Elad Gil as a rare individual who mastered this difficult but effective communication strategy in a role-play exercise.

> Write down what you wanna say, and then say that and don't say anything else.

## 36:06 - 40:07 Dick Costolo's Strategy for Internal Promotions and Key External Hires at Twitter

Dick Costolo emphasized building career paths for internal talent at Twitter, citing Kevin Weil as an example who was promoted from an individual contributor to running all of product after first leading ads product. This approach aimed to prevent employees from feeling their career growth was capped by external hires.

Costolo also made strategic external hires to address specific organizational challenges. Anthony Noto, known for his work at Goldman Sachs with technology and media investors, was brought in to manage Twitter's constant public scrutiny and "drama queen" image, effectively communicating with the investment community.

Another "non-consensus" external hire was Adam Bain from Fox Interactive to lead revenue. Costolo tirelessly pursued Bain for months, recognizing his exceptional work ethic and the critical need for a relentless leader to compete with Facebook for social ad dollars.

While Costolo acknowledged the adage to "hire slow, fire fast," he admitted that he often fired slowly, realizing in retrospect that he knew within six weeks when a termination was necessary. He described firing as a horrible but sometimes necessary task, recalling a conversation with David Rosenblatt about the complex process of terminating an employee with global responsibilities.

> Man, this guy's tireless, and we're gonna be in a constant dogfight and fighting from behind against Facebook for social ad dollars.

## 40:07 - 42:09 Hypergrowth Companies Must Maintain Operating Efficiency

Leaders often face excruciating decisions, such as terminating employees, which can cause significant emotional stress and sleepless nights. Despite the difficulty, these actions are sometimes necessary for the company's long-term health, as illustrated by a baseball analogy where a manager must make a tough call to remove a struggling pitcher.

A significant pitfall for hypergrowth companies, particularly those in the AI sector expanding from single-digit millions to hundreds of millions in revenue, is losing sight of critical business fundamentals. This often happens when a company raises substantial amounts of capital.

When a company secures a large funding round, there's a tendency to deprioritize operating leverage and efficiency. Leaders might mistakenly believe they no longer need to worry about burn rates and capital allocation, diverting their attention to other areas. This complacency can lead to unexpected challenges down the line.

> It's very, very easy to take your eye off the ball when you raise too much money.

## 42:09 - 46:09 Addressing Hypergrowth Challenges: Funding, Talent Management, and Competition

During periods of hypergrowth, companies often face significant pitfalls, one of which is raising too much money. While seemingly beneficial, excessive funding can lead to a loss of focus, making it easier to drift from core objectives rather than operating with efficient constraint. What was once a $20 million Series B now looks like a $100 million Series B, potentially diluting the urgency and strategic discipline.

Another major challenge is maintaining hiring standards. Many CEOs aspire to hire only 'A players,' but this becomes unsustainable when a customer success team, for instance, needs to double its size rapidly due to high growth. Inexperienced managers, often new to their roles, struggle to manage out low performers, frequently attempting to transfer them to other teams to avoid difficult conversations.

To counter this, a rigorous performance management system is crucial. One effective strategy involves preventing employees with low performance review scores (e.g., a 'two' on a one-to-four scale) from switching teams until their performance improves. Senior leadership must also scrutinize review curves to identify managers who might be inflating scores or bouncing underperformers between 'two' and 'three' ratings to avoid termination, ensuring accountability.

Lastly, hypergrowth companies often compete with much larger, established players. It's essential to acknowledge the competition, understand their strategies, and instill a mindset of out-hustling them. When facing a juggernaut like Facebook, for example, a smaller company with fewer resources must constantly analyze what the rival is doing and relentlessly innovate to gain an edge, as Adam Bain did at Twitter.

> They're like huge, and Mark is the most competitive person on the planet. Trust me when I tell you, like, they don't like, they don't say to themselves, 'Oh, whatever, Twitter won that thing, that's fine.' They're like, 'That can never happen again.'

## 46:09 - 48:09 Out-Hustling Juggernauts with Clever Salesmanship and Strategic Acquisitions

A salesperson named Adam employed a clever strategy to compete with Facebook for large client accounts. He would meet with client CMOs, such as those at Unilever, before scheduled competitor presentations to discreetly learn what Facebook was excited to showcase.

Armed with this intelligence, Adam would then use it in his own pitch, positioning his company's offerings in contrast to what Facebook had presented. This wasn't about having more features or resources, but about superior salesmanship that anticipated and addressed the competition's moves, creating a unique advantage.

This approach exemplified how smaller players can challenge market giants by not directly competing on feature parity, but rather by out-maneuvering them through shrewd tactics. The discussion also highlights Twitter's earlier attempt to acquire Instagram, recognizing the talent of founders Kevin Systrom and Mike Krieger, as another form of strategic competition against a juggernaut like Facebook.

> Adam had just come up with a great way of thinking about how to compete with this juggernaut, and the juggernaut's rolling out new things every quarter. It's just good salesmanship.

## 48:09 - 50:09 Dick Costolo Regrets Twitter's Missed Instagram Acquisition

Dick Costolo revealed Twitter's unsuccessful attempt to acquire Instagram, where they offered roughly $700 million in stock. This amounted to over 10% of Twitter's $5 billion valuation at the time. Costolo speculated that, with hindsight, he would have even offered Instagram's co-founder Kevin Systrom the CEO role to close the deal.

Costolo views the failure to acquire Instagram as his biggest regret and a pivotal strategic error. He immediately recognized that Facebook's acquisition of Instagram was a "game changer" that effectively "boxed Twitter out" of the evolving landscape of rich media social feeds.

Despite Twitter having its own short-form video platform, Vine, it was much smaller than Instagram. Costolo accurately predicted that Instagram, under Facebook, would heavily feature video, a move he described as "checkmate" in the social media battle.

> Once they had Instagram, I was like, "Oh man, we're like boxed out on..." That is, that is the future of, of rich media, social media feeds. ... And that, and that was, that was sort of checkmate.

## 50:09 - 54:10 The Infinite Hardness of Content Moderation and the Need for Judgment Calls

Dick Costolo details the extreme difficulty of content moderation, describing it as "infinitely hard." He recounts a challenging scenario at Twitter where accounts posting ISIS videos of a Jordanian pilot being burned were promptly suspended. However, an hour later, the New York Post published a large photo of the same event, immediately creating a dilemma about applying the same rules to a news organization.

Costolo emphasizes that content moderation cannot rely on rigid rules. Instead, platforms must make a multitude of judgment calls, often by individuals with deep situational understanding. He acknowledges that many of these decisions will inevitably be incorrect, a fundamental aspect of the role.

He further clarifies that during his leadership, the primary content issues Twitter faced were widespread Russian bots, phishing attacks, and massive bot farms designed to hack user accounts and steal credit card information. The more recent 'culture war' moderation challenges, such as policies against deadnaming trans people, largely developed after his tenure.

> It was just so, so infinitely hard.

## 54:10 - 56:10 Dick Costolo Reflects on Bad Press and Avoiding Superficial CEO Perks

Dick Costolo recounted the personal challenge of receiving bad press, specifically being named one of the "five worst CEOs of 2014" by Yahoo Finance. His daughter's immediate, humorous dismissal of the ranking—"Nobody reads Yahoo Finance"—helped put the criticism into perspective, highlighting the transient nature of such public judgments.

Costolo also discussed the invitations he received to prestigious social events, such as the "Party of the Year" and the Oscars, solely because of his position as Twitter CEO. He consciously decided to decline many of these invitations.

His reasoning was to avoid becoming overly attached to the superficial perks of leadership. He feared that attending these events regularly would make him dread losing the CEO title, as it would mean losing access to such invitations. He distinguished these from essential duties, like meeting the President to discuss platform abuse or national security issues, which were non-negotiable parts of the job.

> I don't wanna start going to a bunch of stuff that I get invited to because I'm the CEO of Twitter, because then I'll be, I'll be like, 'Oh, I don't wanna not be the CEO of Twitter, ' 'cause I won't get invited to the...

## 56:10 - 58:10 The Cyclical Demand for 'Adult' CEOs and How to Pursue Leadership Roles

The tech industry sees a fluctuating demand for external "adult" CEOs, specifically experienced operating executives. While there are periods when the need for seasoned leaders to manage multi-billion dollar companies founded by younger entrepreneurs becomes apparent, these appointments are often rare, even in large public companies like MongoDB or Workday, possibly happening only once a year. This indicates a wave-like pattern in the industry's embrace of external, experienced leadership.

For those aspiring to CEO positions, actively communicating your career goals is crucial. Dick Costolo highlights Anthony Noto's example: as CFO at Twitter, Noto proactively informed executive recruiters that he was seeking CEO roles. This direct approach helps get aspiring leaders on the radar for top executive opportunities, even if the first role isn't immediate.

Beyond traditional career paths, diverse experiences can prove invaluable for leadership. Costolo shares how his own background, including attempts at Saturday Night Live and handling live TV, built resilience. He notes that facing situations like getting booed by a thousand people in Australia made public speaking for business, such as addressing an all-hands meeting, seem easy, demonstrating how varied life experiences contribute to a CEO's composure and confidence.

> I got booed at midnight in Australia by a thousand people, I can look in the camera and talk about it.

## 58:10 - 1:04:11 Authenticity in Leadership: Beyond Archetypes and Aggression

Many Silicon Valley leaders exhibit passive aggression, hindering genuine communication. In contrast, self-aware executives like John and Patrick Collison at Stripe and Reed Hastings at Netflix demonstrate forthrightness. These leaders are blunt and straightforward without resorting to either passive or hyper-aggressive tactics, fostering a more direct and effective communication style.

A common pitfall for CEOs is attempting to emulate famous archetypes, such as those depicted in biographies of figures like Steve Jobs or Elon Musk. This approach ignores the nuanced reality of their success and creates an inauthentic persona. No one is fooled when someone tries to be someone they are not, and such an effort invariably leads to personal misery and ineffectiveness.

True leadership stems from self-awareness and consistency. Reed Hastings, for example, once prompted a discussion about the origins of success, attributing a significant portion to inherent DNA rather than learned "kick ass" skills, highlighting a deep understanding of self. This self-awareness allows leaders to be genuinely the same person in public and private, avoiding the tension and inauthenticity that arises from maintaining differing personas.

> if you try to be someone you're not Nobody is fooled. Like, you think people are fucking fooled? Nobody is fooled. Everyone knows you're spinning them or you're playing some role and you're not yourself, and nothing is more miserable than trying to be someone you're not.

## 1:04:11 - 1:06:11 Startups benefit from early independent board members and prolonged private status

Dick Costolo emphasized the critical role of independent board members in early-stage companies. He recalled how Peter Fenton from Benchmark assisted in interviewing and closing key executives like Adam Bain and Anthony Noto, providing a crucial third-party perspective on the company's potential and helping to persuade candidates.

Costolo advises against waiting until just before an IPO to bring in independent operators with relevant expertise. He advocates for incorporating such talent much earlier to leverage their operational insights during the company's growth phase.

Reflecting on Twitter's journey, Costolo expressed regret over taking the company public too soon. He believes that running a private company is significantly easier, allowing for a long-term strategic focus without the constant pressure of daily stock price fluctuations or the need to meet quarterly revenue numbers, which often distracts employees.

> I would have kept it private longer if I could go back and do anything over again. It's just so much easier running a private company.

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