20VC YC's Ali Rowghani on Leadership Lessons From Steve Jobs, Ed Catmull and Jack Dorsey & The 3 Traits All Truly Successful Leaders Share

In this episode of "20 Minutes VC," host Harry Stebbings interviews Ali Rowghani, CEO of the YC Continuity Fund, to delve into his transition from an accomplished operator to a venture capitalist. Rowghani's storied career includes pivotal roles at Twitter, where he oversaw exponential growth, and Pixar, where he worked closely with Steve Jobs and learned the importance of team over ideas. He shares insights on leadership, emphasizing clarity of thought, judgment of people, and personal integrity as key traits of great leaders. Rowghani also discusses his approach to evaluating startup teams for investment, stressing the significance of a founder's vision, team-building skills, and commitment. He highlights a recent investment in Segment, praising its team and strategic positioning. Throughout the conversation, Rowghani reflects on lessons learned from industry giants and the challenges and surprises of venture capital, such as the irreversible nature of investment decisions and the long wait to see their outcomes.

• Harry Stebbings hosts the 20 Minute VC podcast and can be found on Snapchat.
• Ali Rowghani is the CEO of YC Continuity Fund, with investments in Segment, Convoy, and Lob.
• Rowghani has experience as CFO and then COO at Twitter, scaling the company significantly.
• Prior to Twitter, Rowghani was CFO at Pixar Animation Studios.
• Thanks given to Sasha at Lendup for the introduction to Ali Rowghani.

"So joining us in the hot seat today, I'm thrilled to welcome not only a very special man, but a man who's had a front row seat for the creation of some truly game-changing companies of the last decade. Ali Rowghani, CEO of the YC Continuity Fund, where he's made investments in the likes of Segment, Convoy and Lob, where he also sits on the board of all three companies."

This quote introduces Ali Rowghani as an influential figure in the venture capital space, highlighting his role at YC Continuity Fund and his board positions at several companies.

• Y Combinator is an accelerator behind successful companies such as Airbnb, Stripe, Reddit, and Dropbox.
• Ali Rowghani has a significant role in the success of these companies from his position at YC Continuity Fund.

"But to this week on the show and I'm very, very excited to be doing a feature week on the world's most successful accelerator, Y Combinator, the organization behind the likes of Airbnb, Stripe, Reddit, Dropbox and many more incredible companies."

The quote emphasizes the impact of Y Combinator as a successful accelerator, having supported a number of high-profile tech companies.

• Rowghani's journey into venture capital was serendipitous, not initially intending to be a venture capitalist.
• He spent significant time as an operator at Pixar and Twitter, witnessing substantial company growth.
• Rowghani joined Twitter with no revenue and a small user base, leaving the company after it had scaled to $2 billion in revenue and nearly 300 million users.
• His transition to venture capital came after Sam Altman of YC approached him to advise YC companies.

"It was kind of a no brainer. I was sure I'll help, and I got involved, and that was in the fall of 2014, winter of 2015, and I really enjoyed spending time at YC."

This quote explains Rowghani's initial involvement with YC, indicating his willingness to help and the enjoyment he found in advising startups.

• YC Continuity Fund is a later-stage investing fund within Y Combinator.
• The fund was established to invest in YC companies as they scale.
• Rowghani was chosen to lead the fund because of his experience with scaling companies and his relationships within YC.
• YC Continuity Fund is seen as a unique opportunity due to its connection to Y Combinator.

"Would you be willing to lead that? And it kind of came as a surprise, and I asked him, why would you choose me? And he said, we already have great relationships with the YC companies. We've already invested in all of them. So we don't think this is a job of going out and doing an incredible job of sourcing, as most VCs have to do, but rather it's about convincing them that YC has more value to add as they start to scale."

The quote reveals the rationale behind Rowghani's selection to lead the YC Continuity Fund, focusing on the added value YC can provide to its companies during scaling rather than sourcing new investments.

• For founders and operators, people operations is a critical function.
• Lattice is highlighted as a leading performance management solution for growing companies.
• Lattice offers tools for performance reviews, continuous feedback, OKR tracking, and one-on-one meetings.
• Recurly is mentioned as a platform powering subscription success, increasing revenue and reducing churn.

"Your most important job is people operations, whether that be hiring execs, developing managers, or retaining top talent."

This quote stresses the importance of people operations in a company's success, indicating that it encompasses hiring, development, and retention of talent.## Working with Steve Jobs

• Ali Rowghani recounts his experience of working with Steve Jobs at Pixar.
• Rowghani had to present a long-term plan to Steve Jobs, highlighting flaws in Pixar's ambition to increase movie production.
• Ed Catmull, president of Pixar, insisted that Rowghani use Keynote instead of PowerPoint for the presentation to Jobs.
• Rowghani faced a last-minute scramble to convert his presentation, resulting in a night of reassembling slides in a new software.
• The next day, Steve Jobs recognized and appreciated the use of Keynote, easing the tension before the presentation.

"Steve was the CEO. Steve was also the CEO of Apple. And so he was only spending a day a week, usually at Pixar." This quote explains Steve Jobs' dual role as CEO of both Apple and Pixar, indicating his limited time at Pixar.

"Can you make sure that the presentation is in keynote?" This quote shows Ed Catmull's request for Rowghani to use Apple's Keynote software for the presentation, emphasizing the importance of using Apple products when presenting to Steve Jobs.

"Everything shatters. All of the work that I'd done, all of the slides that I'd meticulously build, all of the animations that I'd put into the slide, everything was in tatters." Rowghani describes the catastrophic result of converting his PowerPoint presentation into Keynote, which necessitated an all-night effort to rebuild it.

"Keynote." Steve Jobs' one-word acknowledgment of Rowghani's use of Keynote, indicating his preference and approval of the software, which set a positive tone for the presentation.

• Pixar had an emotional investment in the Toy Story franchise, viewing the films as their creative offspring.
• Disney held the rights to produce sequels to Pixar films, creating tension when they began producing Toy Story 3.
• The acquisition of Pixar by Disney in 2006 allowed Pixar to regain control over Toy Story 3 production.
• Pixar's original creators reunited to work on Toy Story 3, with Michael Arndt writing the script.
• A table read of the first draft of Toy Story 3's script brought the team together, evoking emotional responses.

"Disney had the right to make sequels to Pixar films. So Disney had the right to make the sequel to Toy Story three, which was an incredible... I can't exaggerate what an emotional issue that was for the Pixar folks." This quote highlights the deep emotional connection Pixar's team had with their films and their distress over Disney's initial control over Toy Story 3's sequel.

"We sold the company to Disney in 2006, and as part of that transaction, Disney naturally closed down their own production efforts on Toy Story three and gave the film back to Pixar." The quote explains the resolution of the conflict over Toy Story 3 after Disney's acquisition of Pixar, allowing the original creators to work on the sequel.

"They went through the script, and it was heartwarming and funny, et cetera." Rowghani describes the emotional and uplifting experience of the table read for Toy Story 3's script, emphasizing the team's creative synergy and passion for the project.## Emotional Impact of Storytelling

• Pixar's storytelling ability is powerful and can evoke emotions even in company leadership.
• The experience of reading the "Toy Story 3" script and observing the emotional response among the leadership team indicated the film's potential success.
• The shared emotional reaction to the narrative underscored the quality of the film.

And as he starts to give Woody away, who's his favorite toy, as I'm listening and reading the script along with the actors, all of a sudden I feel myself tearing up and, like, tears kind of coming down my cheeks.

This quote illustrates the speaker's emotional response to the storytelling in "Toy Story 3," reflecting the script's ability to connect with the audience on a personal level.

• Great leaders do not conform to a single formula; they exhibit a range of styles and approaches.
• There are three fundamental traits shared by great leaders: clarity of thought and communication, exceptional judgment about people, and personal integrity and commitment.
• These traits are essential for setting a compelling vision, choosing the right team, and overcoming challenges.
• Personal leadership styles may vary, but these core traits are consistent among effective leaders.

I think the biggest lesson that I took is that there's not one formula to being a great leader.

The quote emphasizes the diversity of leadership styles among successful leaders, debunking the idea of a universal leadership formula.

Great leaders all share an incredible clarity of thought and communication... great leaders have exceptional judgment about people... great leaders have exceptional personal integrity and commitment.

This quote details the three key traits that are consistently found in great leaders, regardless of their individual differences.

• The same three leadership traits are used to assess entrepreneurial teams.
• Clarity of vision, judgment about people, and personal integrity are crucial for entrepreneurs.
• These criteria are important in both the initial evaluation and ongoing relationship with founders.
• Venture Capitalists (VCs) can assist entrepreneurs in improving these areas over time.

I think assessing the quality of a leadership team and the quality of a CEO is pretty fundamental to this job.

Ali Rowghani points out the importance of leadership quality in the evaluation process for VCs, highlighting it as a key aspect of the role.

These are also areas that you can help people kind of get better in these areas.

The speaker suggests that VCs not only evaluate but also contribute to the development of leadership skills in the entrepreneurs they invest in.

• Leadership qualities can be developed and improved, regardless of natural predispositions.
• Diverse leadership styles mean that there is no single type of person who can become a great leader.
• Improving skills such as evaluating people can be learned and honed over time.
• Founders can prepare for roles they are unfamiliar with by learning from those who excel in those positions.

One of my core beliefs is that everyone can get better as a leader.

This quote expresses the speaker's belief in the potential for all individuals to improve their leadership abilities, supporting the idea of personal growth.

I don't really disqualify anyone from being able to become a great leader.

Ali Rowghani asserts that there is no inherent disqualification from leadership, suggesting that anyone has the potential to become an effective leader with the right development.

• Transitioning from an operational role to a VC involves adjusting to the finality of investment decisions.
• Unlike operational decisions, investment decisions cannot be tested on a small scale or easily reversed.
• The biggest challenge in this transition is adapting to the binary nature of investment decisions.

For know, I think the biggest challenge is as an operator, almost every decision you make, you can either test at small scale to see if it works, or reverse it if it doesn't work.

Ali Rowghani describes the key difference between making decisions as an operator versus as an investor, emphasizing the finality and irreversibility of investment choices.## Challenges in Venture Capital

• The biggest challenge in venture capital is reversing decisions or scaling down once a company has grown.
• It is difficult to undo actions or reduce scale without significant consequences.

at small scale or undo them, I think is probably the biggest challenge that I've encountered.

This quote emphasizes the difficulty in making changes to a company's trajectory once it has reached a certain scale.

• The time gap between investment decisions and understanding their outcomes is a surprise in VC.
• It takes years to see if an investment was successful, akin to taking a shot in billiards and checking later if the ball went in.

I would say the biggest surprise is the time gap between making a decision to invest and realizing if that decision was a good decision.

Ali Rowghani expresses his realization of the delayed feedback loop in venture capital investment outcomes.

• Ali Rowghani enjoys reading biographies, particularly of historical figures like Theodore Roosevelt.
• Biographies offer insights into overcoming hardships.

You know, honestly, I'm sort of nerdy here. I love biographies, and I love biographies, sometimes of historical people, because I feel like you learn a lot from the hardships that they endured and how they sort of overcame them.

Ali Rowghani shares his personal interest in biographies and the lessons they provide.

• Ali Rowghani believes that a great team is more important than a great idea, a philosophy stemming from his experience at Pixar.
• In Hollywood and possibly in venture capital, there's an overemphasis on the idea rather than the team.

a great team is more important than a great idea.

This quote captures Ali Rowghani's belief in the paramount importance of team quality over the initial idea or concept.

• Ed Catmull, founder and president of Pixar, is Ali Rowghani's professional mentor.
• Working closely with Ed Catmull taught Rowghani valuable leadership qualities.

Professional mentor, I would probably say Ed Katmull, who is the founder and president of Pixar.

Ali Rowghani credits Ed Catmull as a significant mentor and highlights the impact of their working relationship.

• Bill Gurley's writings, specifically "View from the Top," are favored by Ali Rowghani for industry insights.

Like, I like a lot of the writing that Bill Gurley has done.

Ali Rowghani recommends Bill Gurley's work for its valuable perspectives on the industry.

• Ali Rowghani would like to see startups be more cautious with raising too much capital too early.
• Excessive capital can lead to a lack of urgency and complacency within a company.

I think if you have too much capital, it saps a company of urgency, of energy, it makes the company more lazy, et cetera.

This quote reflects Ali Rowghani's concern that too much early funding can negatively impact a startup's drive and efficiency.

• The decision to invest in Segment was based on the strength of the team, the strategic position of their product, and future potential.
• Segment is creating a new product category and is considered a leader in the customer data platform space.

We really love the team, first and foremost, Peter and his two co founders, Ilya, and know they're creating a new product category and they're the leader in this new product category, this customer data platform.

Ali Rowghani explains the rationale behind investing in Segment, highlighting the importance of team quality and market leadership in their decision-making process.