20. Transitioning Roles: From COO to Venture Capitalist

Our special guest is Cleo Sham, Venture Partner at StrideVC., ex-Uber and former COO.

12/7/20234 min read

We discuss the following:

  • Why did you decide to move from operator to investor?

  • How did being an operator inform your role as a VC?

  • Where did you find joy in the COO role? Where did you find it as a VC?

  • Which role is more stressful: COO or VC?

  • When you received critical feedback as a leader, how did you deal with it?

  • How do you carve out quality thinking time with so many diverse opportunities?

  • How would a COO make the move to VC?

Listen here.


Before joining Stride as an investor, I had built and led teams as a scale-up operator across China and EMEA.

I joined Uber as one of the first GMs on the ground in China in 2014, building the Guangzhou business into Uber's largest city by volume globally and led China National Operations up until Uber China's $35B merger with Didi Chuxing in 2016. I subsequently moved to Amsterdam as EMEA Director of Operations to lead the platformization of Uber's ridesharing business across 45 countries.

Relocating to London in 2019, I took on the COO role at Spotahome after their $40M Series B, led by Bond Capital. Spotahome is a b2b2c mid-term rentals marketplace, and there I transformed and led a ±200 person team across sales, marketing, operations, strategy, and customer support.

I love building and working with startups, having been a 3x founder earlier in my career and an active angel investor along the way. Originally from Hong Kong, I began my career at McKinsey in Asia and started investing as a proprietary trader at Bank of America Merrill Lynch.

Summary of the episode

Zoe diet results and food obsession. 0:05

Bethany discovered she's highly reactive to sugar through a Zoe diet test, meaning she must avoid it for the rest of her life.

Bethany can process fats easily but struggles with sugars, including fruits like raspberries and lemons.

Bethany struggles with an abnormal obsession with food, which has led to medical anxiety and a fear of fatty liver disease.

She has realized that her anxiety is not related to diet but rather a combination of her upbringing, personal experiences, and a lack of understanding about preventative medicine in the UK.

Career transitions and personal growth after recognizing mortality. 5:44

Bethany reflects on her father's death and its impact on her perspective on life and work.

Bethany wants to use her inherited money to pursue her passions and explore new experiences without worrying about financial constraints.

She is considering how to use her next decade to make the most of her life and career, with a focus on fun and exploration.

Brandon and Bethany discuss their goals and motivations, including starting a community for ambitious people and advocating for cannabis legalization in the UK.

Bethany is taking a writing course and a pottery course to improve her skills and push herself outside of her comfort zone.

Vulnerability, self-expression, and career growth in one's 40s. 11:57

Bethany shares her insights on the importance of vulnerability and self-expression, citing Brene Brown's work on shame and the need to share feelings with safe people to build support.

Clea Sham joins the conversation and adds her perspective on the value of being true to oneself, even in the face of criticism or rejection from others.

Transitioning from operator to investor with Cleo and Speaker 3. 14:33

Cleo is an outstanding senior woman who has held various leadership roles, including COO at a home and partner at stride.

Cleo transitioned from operator to investor due to a desire for tangible businesses and working with teams, and joined Uber as CEO to think through business drivers and prioritize resources.

Investing background informing operations roles and vice versa. 16:54

Cleo's investment background informed their operations roles, including building models and making decisions based on financial data and business drivers.

Cleo's experience as an operator reinforced their investing role at Stride VC, allowing them to apply their knowledge of building businesses and assessing companies.

Cleo learned to regulate their emotions and make decisions based on data in a high-pressure environment, which helped them perform as an investor.

Cleo received feedback from their team on being too emotionless and impenetrable, which could impact their ability to connect with others.

Leadership, teamwork, and investment strategies in the tech industry. 22:12

Cleo shared a personal experience of receiving feedback from a direct report during a one-on-one meeting, which led to a valuable learning moment for them.

The feedback was presented in a supportive manner, with the direct report acknowledging the speaker's humanity and vulnerability, and the team having Cleo's back.

Cleo chose to stay and lead the team through the challenging moment, ultimately resulting in the team staying at the top for over six months.

Bethany emphasizes the importance of building trust with founders, tailoring communication styles to each founder's needs, and prioritizing their comfort level in the investment process.

Cleo highlights the people side of the VC role, including sourcing, selecting, winning, and supporting founders, and how their operational leadership experience informs their approach to these tasks.

VC vs. CEO roles, satisfaction, and stress. 28:34

Cleo highlights the differences between operating a business and being a VC, with the former providing more tangible results and the latter offering a wider range of people to learn from.

Cleo finds personal growth and meeting new people satisfying aspects of being a VC, with the opportunity to learn from a diverse range of founders and investors.

Cleo highlights the benefits of VC, including more control over time and the satisfaction of supporting founders.

Both identifying the next investment and making non-reversible decisions are stressful aspects of VC work.

The challenges of time management for venture capitalists. 33:29

Cleo discusses the challenges of managing multiple boards and sourcing new investments while also prioritizing thinking time.

Brandon adds that quality thinking is crucial to understand the legs of a product opportunity in a rapidly changing market.

Cleo describes their role as a "lone wolf" investor, responsible for researching and deciding on investments, while also being part of a team that looks at things together on designated days.

Cleo highlights the need to create time for both solitary work (developing a thesis, drilling down into an industry) and social work (meeting founders, going to events) to be successful in their role.

Becoming an investor, including self-reflection and networking. 39:24

Cleo suggests starting small by investing with your own money and building a network of investors, founders, and operators.

Cleo advises spending time understanding the different types of VC firms and their approaches to investing, rather than rushing into a decision.

Reflect on your energy sources and strengths to determine if investing is the right career move (42:47)
Making a switch to investing is not irreversible, and people can switch back and forth in mature venture markets (43:53)