20VC How To Optimise DecisionMaking Frameworks, How To Really Get The Most Out Of Your Board and When Your Brother Is Also Your CoFounder; The Secret To Working with Family with Rob Sadow, Founder & CEO @ Scoop

In this episode of "20 minutes vc," host Harry Stebbings interviews Rob Sadau, the founder and CEO of Scoop, a startup revolutionizing commutes by facilitating carpooling with coworkers and neighbors. Sadau, who has raised over $37 million from investors like Danny Rhimer at Index and Brooke Porter at G2, discusses his journey from Bain and Company to launching Scoop, driven by his passion to improve daily commutes. He emphasizes the importance of decision-making from first principles and the balance between data-driven and instinctive choices. Sadau also sheds light on the dynamics of working with his brother and co-founder, the significance of aligning team members with the company's mission, and the value of maintaining transparency with board members. Additionally, he predicts a future of shared car ownership and highlights the tight labor market's impact on Scoop's business model.

• Harry Stebbings introduces the podcast and highlights Rob Sadow's accomplishments.
• Rob Sadow, founder and CEO of Scoop, has raised over $37 million in funding.
• Scoop aims to improve commutes by providing convenient carpools.
• Rob Sadow's previous roles include manager at Bain and working with Better Place in Israel.
• Harry thanks various individuals for contributing questions for the interview.
• Harry also talks about Brex, Terminal, and Cooley, companies providing services to startups and VCs.

"But to our episode today and what a founder we have joining us in the hot seat today as I'm very excited to welcome Rob Sadow, founder and CEO at Scoop, the startup that dramatically improves your commute, providing convenient carpools with coworkers and neighbors."

This quote introduces Rob Sadow and his company, Scoop, which focuses on improving commuting experiences.

• Rob Sadow's interest in commuting began with his own experiences in Atlanta.
• His long commutes during high school impacted his daily life significantly.
• After moving to San Francisco, the challenges of commuting resurfaced, leading to the idea of Scoop.
• Scoop's goal is to make commuting a more valuable and meaningful part of the day.

"So in many ways, it started with just a deep, underlying passion for the experience of the commute."

Rob Sadow discusses his personal connection to the problem Scoop aims to solve, emphasizing the impact of commuting on daily life.

• Commute time and quality are significant factors in overall happiness, second only to salary.
• Increasingly, long commutes are a top reason for people leaving their jobs.
• Scoop aims to address these issues by improving the commuting experience.

"Did you know that the commute time and commute quality is the second biggest contributor to happiness other than salary?"

Harry Stebbings presents a fact about the importance of commuting to personal happiness, which aligns with Scoop's mission.

• Rob Sadow's decision-making skills were honed during his time at Bain.
• He breaks down complex problems into simple elements and tackles them systematically.
• He emphasizes the importance of returning to first principles and working with his board for feedback.

"A lot of how I think about decision making actually comes from my time at Bain."

Rob Sadow credits his consulting experience for his structured approach to decision-making.

• The balance between emotional and rational decision-making depends on the company's stage.
• Early stages may require more data-driven decisions, while later stages might rely more on speed and decisiveness.
• Rob Sadow emphasizes the importance of being nimble and able to act on partial information.

"I think it depends a lot on the stage of the company honestly, and the type of topic early on... once that shifted and we raised capital and really started to build, speed, became very important."

This quote explains how the balance between heart and head shifts as a company grows and the need for speed becomes more critical.

• Rob Sadow tries to limit the number of decisions he personally needs to make.
• He focuses on building a culture where teams can work cohesively and make aligned decisions.
• Empowering teams and developing people is key to scaling the company and managing time effectively.

"I think part of it is trying to make sure that I limit the exact number of decisions that I need to make."

Rob Sadow discusses his strategy for managing his decision-making workload by empowering his teams.

• Rob Sadow emphasizes the importance of empowering leaders within the company to make decisions.
• He believes that not all decisions should flow up to him as the CEO.
• This approach allows him to focus on a few critical company matters while his team handles the rest.
• Empowerment creates space for the right people to make the right decisions, fostering a culture of accountability and responsibility.

"How do I make sure that our leaders feel empowered to own the areas in which they operate? A source of guidance or input or strategic advice? But ultimately, not all decisions flow up to me."

This quote underscores Sadow's belief in delegating decision-making authority to his team leaders, freeing him to concentrate on the most crucial aspects of the company.

• Rob Sadow agrees with the idea that decisions are never perfect, and the aim is to have a good batting average.
• He acknowledges that it's impossible to always make the right decision due to incomplete information and changing realities.
• The goal is to make decisions quickly and to be right more often than not.
• Experimentation is vital, and the focus should be on the product of decision speed and accuracy.

"It's a funny thing that I talk about with my team is, look, you shouldn't assume that every decision I make is going to be right, but for scoop to be successful, I have to be right a whole lot more often than I'm wrong over time for us to do what we need to do."

Sadow conveys to his team that while not every decision will be correct, the overall success requires him to be right more frequently than wrong.

• Sadow reevaluates the company's strategy approximately every six months.
• Constantly changing strategy can create confusion and lack of direction within the team.
• Establishing a clear vision and mission helps maintain strategic focus and alignment.
• Strategies must be revisited regularly due to changing realities, but guardrails help minimize the need for constant reevaluation.

"I try not to reevaluate strategy too often. I think if you're changing strategy every week or two weeks or months, it actually creates whiplash for the team."

This quote highlights Sadow's approach to maintaining strategic stability to prevent team disorientation, while still being open to necessary adjustments.

• Working with a sibling as a co-founder involves a high level of inherent trust.
• Rob Sadow values the alignment and mutual best interests he shares with his brother.
• Trust and understanding are foundational to navigating the challenges of building a company together.

"For me, that's the greatest privilege in working with my brother. I know that we're aligned in where we're going."

Sadow expresses the deep trust and alignment he has with his brother, which is pivotal in their co-founding relationship.

• Role clarity is essential for founders and is also crucial for the team's understanding of decision-making processes.
• Different backgrounds and perspectives can lead to varied approaches to problem-solving.
• Establishing clear roles helps in decision-making and company efficiency.
• Rob Sadow advises being direct about role segmentation early on to avoid future issues.

"Role clarity is not just important for the two of you, or three of you, or however many people it might be as founders. It's critically important for the team."

This quote emphasizes the importance of role clarity not only for founders but also for the entire team to ensure smooth operations and decision-making.

• Founders should treat board members as allies and not hide company issues from them.
• Transparency with the board fosters trust and can lead to valuable assistance.
• Good board members understand that challenges are part of the business and can offer experienced guidance.

"I think the best way to partner with a board is to treat them as if they are on your side of the table."

Sadow suggests that treating board members as partners, rather than adversaries, leads to a more productive and supportive relationship.

• Rob Sadow discusses the strategy for board meetings, emphasizing focus on key challenges.
• The importance of transparency and trust in board conversations is highlighted.
• Relationships with board members are built through regular communication and personal connections.

"We think about board meetings as an opportunity to say, look, there are a lot of things that are going well with the company... Here are two or three things that are broken. We need to go focus on a, on b, on c."

This quote explains that board meetings are used to address a few critical issues rather than only celebrating successes, which fosters a problem-solving environment.

"Bringing them inside, I talk to them all the time on different topics. When I have questions, I'll pick up the phone or text them."

Rob Sadow stresses the importance of maintaining open lines of communication with board members to build trust and ensure effective collaboration.

• Rob Sadow prefers not to direct questions to specific board members in meetings to encourage a free flow of ideas.
• Outside of meetings, Sadow reaches out to board members with particular expertise for targeted advice.
• The approach to board meetings is designed to avoid grandstanding and promote valuable contributions from all members.

"When it's a board meeting, I generally won't overly direct toward a certain person for feedback... our board meetings are more free flowing conversations."

This quote indicates that Rob Sadow encourages a collaborative environment in board meetings where all members can contribute regardless of their specific expertise.

"Danny... has a lot of history and context... Brooke... is more of a growth stage investor."

Sadow recognizes the unique strengths of individual board members and seeks their insights on relevant issues outside of formal board meetings.

• Establishing trust begins with aligning the vision for the company between founders and board members.
• Founders should feel comfortable discussing sensitive issues without fear of negative repercussions.
• Early board meetings should set the tone for open and supportive discussions about challenges.

"Trust starts with alignment around vision for the company... making sure that there's common vision on exactly where the company should go."

Rob Sadow believes that trust is built on a shared vision for the company, which is established during the initial investment diligence process.

"Making sure that there is dedicated time for what's wrong, that you put it in as simple terms as possible and how you're going to fix it, and that it's a supportive conversation."

This quote emphasizes the importance of creating a board meeting atmosphere where problems can be addressed constructively and without fear of judgment.

• The company culture values betting on the team's potential and providing opportunities for growth.
• Honest feedback and encouragement are integral to the company's values and help foster professional development.
• Professional development is woven into the company's hiring process and daily operations.

"Betting on ourselves and the team is one of our values... we do not historically try and hire folks that have done something four times or five times or six times before."

Rob Sadow articulates the company's preference for hiring high performers with untapped potential rather than those with repetitive experience.

"Two of our other values are one, being open, honest and direct... and two, something we call give a good push."

These values are designed to encourage a culture of direct feedback and mutual support, enabling employees to grow and take on challenges.

• Rob Sadow shares his favorite interview question, which seeks to understand a candidate's clarity on their career aspirations.
• The alignment of career goals with the company's opportunities is a key factor in the hiring process.

"My favorite interview question is, let's imagine the next chapter of your career is the next five years... what happens or where do you see yourself at the end of that chapter?"

This question is used to gauge whether a candidate's personal career goals align with what the company can offer, ensuring mutual benefit and satisfaction.

• The employment market is described as tight, with a scarcity of skilled labor across various sectors.
• Authenticity and a deep caring for employees are essential for long-term retention.
• Alignment of personal career goals with company opportunities begins at the interview stage and continues throughout employment.

"The employment market is incredibly tight... it is so difficult to recruit and retain top talent and there's a scarcity of skilled labor in a whole bunch of different categories."

Rob Sadow acknowledges the competitive nature of the current job market and the challenges it presents for hiring and retention.

"It starts with authenticity and really deep caring about your people... making sure that what people want to do, what they want to accomplish over the next few years, is aligned with what we can deliver."

This quote highlights the company's commitment to aligning employee aspirations with the company's growth, which is key to their retention strategy.

• Scoop places significant emphasis on employee development through continuous conversations.
• Professional growth is discussed in various settings: one-on-ones, skip-level meetings, and professional development reviews.
• A biannual review cycle is implemented to evaluate employee progress and set future goals.
• Personal well-being and cultural integration are also key considerations in employee assessments.
• Scoop's leadership prioritizes hiring individuals with a strong orientation towards people and culture.
• Transparency and authenticity are practiced openly in company meetings, fostering trust in leadership.

"It takes place in one on ones with their manager. It takes place in skip level, one on ones with the person above them. It takes place in professional development. And we do a review cycle every six months to talk about where are you at? Where do you want to go?"

This quote outlines the structured approach Scoop takes to ensure that employees have regular opportunities for feedback and growth discussions with their managers and higher-level executives.

"We by nature just my brother and I invest really aggressively in this topic and have built a team of people that actually care really deeply about this also because we've been unwilling to hire anybody that doesn't have that same people orientation."

Rob Sadow emphasizes the intentional effort he and his brother make in nurturing a people-oriented culture at Scoop, highlighting their selective hiring process.

• Rob Sadow prefers reading science fiction and fantasy, particularly "The Wheel of Time" by Robert Jordan.
• He values the escapism and thought expansion that the genre offers.

"My favorite book is actually the Wheel of Time by Robert Jordan... It just gives me this opportunity to escape from daily life and stretch my thinking and just explore other concepts."

This quote reveals Rob Sadow's favorite book and his reasons for enjoying it, demonstrating the importance he places on creative thinking and exploration through reading.

• Rob Sadow believes that Silicon Valley's reputation needs improvement, particularly regarding empathy and social responsibility.
• He acknowledges issues in the tech industry such as data privacy concerns and the need for genuine commitment to bettering the world.
• Scoop aligns with these values by contributing positively to societal needs.

"I think the way that we reflect or the way that we are viewed across the rest of the country... that the everyday person actually really does care about that."

This quote indicates Rob Sadow's awareness of the tech industry's image problem and his desire to change the perception by addressing real concerns.

• Rob Sadow predicts a shift towards shared car ownership over the next several decades.
• He expects autonomous vehicle technology and policy to develop gradually, leading to shared vehicle fleets.
• The transition from individual car ownership to shared fleets is seen as a long-term trend.

"I think it will be shared, is probably the most important thing... that's probably a question of decades, more than years, in terms of how long until you actually start to see that flow through the actions and behaviors of everyday people."

Rob Sadow's quote reflects his vision for the future of car ownership, highlighting the eventual move towards shared transportation solutions.

• Rob Sadow believes that great technology companies and talent can emerge from any location, not just Silicon Valley.
• He anticipates a democratization of the tech industry, with successful companies operating outside of Silicon Valley.
• This belief challenges the conventional wisdom that proximity to Silicon Valley is necessary for tech success.

"I believe that great technology companies and kind of like great engineers and great talent can be found anywhere."

The quote conveys Rob Sadow's conviction that talent and successful tech companies are not geographically restricted to Silicon Valley.

• Scoop's mission is to enhance carpooling experiences in partnership with employers.
• The company aims to improve carpool experiences and expand employer relationships.
• Long-term goals include addressing broader commuting challenges for enterprises and becoming a strategic partner in improving employee commute experiences.

"We want to solve more and more of the challenges that enterprises struggle with when it comes to the commute... we can differentiate our employee experience because of it."

Rob Sadow's quote outlines Scoop's future objectives, emphasizing the desire to transform commuting into a strategic advantage for employers.

• The board members unanimously recognize Rob Sadow for his unique decision-making and ability to inspire his team.
• His leadership style contributes significantly to Scoop's culture and success.

"You know, astrally, it was agreed that you are unique both in decision making and kind of inspiring a team."

This quote from Harry Stebbings reflects the board's high regard for Rob Sadow's leadership qualities at Scoop.

• Harry Stebbings endorses Brex, a corporate card for startups offering high limits and no founder liability.
• Terminal is promoted as a solution for building skilled remote engineering teams, handling various aspects from logistics to community.

"Brex founders Henrique and Pedro built a payments business in Brazil, but found themselves rejected for a corporate card when they were in Y combinator." "Terminal is your dedicated partner in quickly building skilled remote engineering teams."

These quotes from Harry Stebbings serve as testimonials for the services provided by Brex and Terminal, highlighting their unique selling points and the problems they solve for startups.

• Cooley is presented as a leading global law firm specializing in startups and venture capital.
• The firm has a long history of working with venture capitalists and assisting with the entire fund lifecycle.

"Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world."

Harry Stebbings provides a historical perspective on Cooley's involvement in the venture capital space, emphasizing its leading role and expertise.