Jeff Lawson is the Founder & CEO @ Twilio, the company that allows you to unite communications and strengthen customer relationships across your business. Prior to their incredibly successful IPO in 2016 Jeff raised funding from some of the best including Bessemer, Union Square Ventures, Redpoint, Salesforce and Founders Fund to name a few. Before founding Twilio, Jeff was co-founder & CTO of NineStar, founding CTO of Stubhub.com, co-founder, CEO & CTO of Versity, and one of the first product managers for Amazon Web Services.
1.) How Jeff made his way into the world of tech and startups and what that founding a-ha moment was for Jeff with Twilio? When explaining new ideas to people, what signals to Jeff that the idea is resonating? Are there clear indicators an idea is not resonating?
2.) Leadership: What does great leadership mean to Jeff today? How has Jeff's leadership style changed and evolved over the years? What does Jeff believe is the key to great storytelling? How has the leadership style required, changed in a COVID world? What have been the biggest inflection points in his leadership?
3.) Culture: What does Jeff believe are the 3 key ingredients to company culture? How can leaders create a tribe that people associate with? What are the biggest lessons we can take from sport and religion when it comes to culture building? At what points has Jeff been concerned about the Twilio culture? What did he do to rectify it? Why are "values nice but principles better"?
4.) Decision-Making: How has Jeff created a culture of decentralised decision-making? What has Jeff done to ensure the best ideas rise to the top? In what ways can leaders ensure people feel safe to be bold and go big, without the fear of failure? How does Jeff determine when to give or remove resources from new ideas? How does Jeff think about the importance of "focus"?
5.) Diversity: Frank Slootman previously said, "diversity should not override merit". What are the core problems that Jeff has with this statement? How do Twilio construct their recruitment pipelines to ensure diversity? Why does Jeff believe the secret to human assessment is one of "miles travelled"? What are the signals of this?
Jeff’s Favourite Book: Made to Stick: Why some ideas take hold and others come unstuck
Mark Mullen is the Co-Founder of Bonfire Ventures, one of LA's leading early-stage funds, now on their 3rd Fund with $101M in the latest. In the past, Mark has invested in the likes of Trade Desk, Scopely, GOAT, ChowNow, Niantic and Pendo to name a few. Prior to co-founding Bonfire, Mark was a solo GP with Double M and then through Mull Capital, Mark is also an LP in other funds investing in 15 including the likes of Upfront, Freestyle, Backstage and Crosscut to name a few.
1.) How Mark made his way into the world of venture, came to found Double M and why he decided he wanted to co-found Bonfire and be in a partnership, not a solo GP model?
2.) Portfolio Construction: With the new fund, how did Mark think about the right portfolio construction? What is the right level of diversification? How many lines should be in the portfolio? How important is ownership today? Is it possible to build ownership in your best companies over time? How does Mark think about proactive reserve allocation today?
3.) Investment Decision-Making: How does Mark think about the right investment decision-making structure with Bonfire today? How can one retain speed but also increase the number of decision-makers? How does Mark feel about the compression of fundraising timelines today? What advice does Mark give to founders when selecting their cap table?
4.) Boards and Time: How does Mark evaluate his own style of board membership? How has it changed over time? What do the best do on boards that makes them so great? How does Mark think about time allocation across the portfolio? Should you only spend time with winners? What have been some of his biggest lessons from this?
Mark’s Favourite Book: Undaunted Courage
Mark’s Most Recent Investment: Topia
Rishi Sunak was appointed Chancellor of the Exchequer on 13 February 2020. He was previously Chief Secretary to the Treasury from July 2019 to February 2020, and Parliamentary Under Secretary of State at the Ministry of Housing, Communities and Local Government from January 2018 to July 2019. He spent his professional career before politics in business and finance, working internationally. He co-founded an investment firm working with companies in multiple geographies and used that experience to help small and entrepreneurial British companies grow.
1.) Rishi's first job was waiting table in a restaurant, what were his biggest takeaways from that first job? How did Rishi's time at Stanford impact his operating mindset today? How did Rishi make his way into the world of politics following a very successful career in finance?
2.) Talent: What does the UK need to do to become a global talent hub? How can Visa programs be reformed and innovated to ensure the UK is an attractive destination for the best talent? On reflection, where has the UK done well on talent and immigration? On the flip side, what has not worked? Why? What would Rishi have done differently?
3.) Entrepreneurs Relief & Capital Gains: What is the logic behind the removal of entrepreneurs relief? Why is it inefficient in its current form? How does Rishi think about using capital gains as a tool to attract the best to build and invest in the UK? Why does Rishi believe the UK is the most attractive place to build a business from a tax perspective? How does the UK compare to the EU and US?
4.) Driving Further Investment in the UK: What worked and what did not work with regards to "The Future Fund"? What would Rishi have done differently? What can Rishi and the UK do to encourage pension funds to invest more in venture moving forward? What are some elements the public assume the government can and should do, but in reality, you cannot?
5.) Rishi Sunak AMA: What does Rishi's morning routine look like? What time does Rishi wake up? What does he have for breakfast? What does the workout routine look like for Rishi? Who is his favourite Peloton instructor? Why? What is his guilty treat food-wise? How often does he have it? How did it feel for Rishi when he delivered his first budget? Was he nervous? How does Rishi deal with nerves today?
Rishi’s Favourite Book: Roald Dahl
Rafael Ilishayev is the Co-Founder & Co-CEO @ GoPuff, one of the market leaders delivering daily essentials in minutes. GoPuff's latest funding round priced the company at a reported $8.9Bn in March 2021 and to date, Rafael has raised over $2.4Bn for the company from the likes of Accel, Softbank, Fidelity, Baillie Gifford, D1 Capital and more. Rafael has scaled the company to over 550 US cities with over 7,000 employees nationwide.
1.) How Rafael made his way into the world of startups with the founding of GoPuff and how he turned it from a college delivery business into a nationwide leader with over 7,000 employees?
2.) Funding: Why did Raf wait until 2.5 years into the business before raising funding? What did that time bootstrapping the business teach Raf? How did it change his thinking on unit economics? How were GoPuff able to be EBITDA profitable from day 1? How do they have such superior margins in an industry blighted by low margins?
3.) New Markets: How does GoPuff determine attractive markets to scale into? What are the leading indicators of "good markets"? What resources are required to open new markets? What is the time to breakeven on new markets? How many micro-fulfilment centres does it take to win a new market? What are the biggest challenges moving into new markets?
4.) Competition: The market has become a lot more competitive, why does Raf feel this is not a market you can win without years of experience? What have they built that other new entrants do not have? Will this be a consolidatory landscape or will many of the new entrants die? Why is Raf planning to invest hundreds of millions into Europe over the coming years?
5.) Driver Efficiency & CACs: What have been Raf's biggest lessons when it comes to driver efficiency? How many deliveries does a driver need to make in one hour for the model to work? How does Raf think about the negative network effects of the model where the more demand, the longer delivery time? How can GoPuff prevent that?
Rafael’s Favourite Book: Trillion-Dollar Coach: The Leadership Handbook of Silicon Valley's Bill Campbell
Jay Simons is a General Partner @ Bond Capital, with their $1.25Bn debut growth fund in 2019 they made their mark on the venture landscape and have since made investments in the likes of Revolut, Canva, NextDoor, IronClad and my favourite, On Running. As for Jay, prior to entering venture, he spent an incredible 12 years at Atlassian including 9 years as President, playing an instrumental role in their hyper-growth journey. Jay is also a board member with both Zapier and HubSpot, two of my favourite SaaS companies.
1.) How Jay made his way into the world of startups following a stint as a pianist in Asia and how that startup journey led to his joining Bond on the venture side?
2.) Why does Jay believe the best companies build economies around themselves? What does this look like in reality? When is the right time for the company to start building these economies? As an investor, what are the signs that a founder is proactively thinking about this? What are some of the biggest mistakes people make when building economies?
3.) Why does Jay believe Partner/Channel networks can be so powerful? When is the right time to build out channel partners? What is the training framework for these partners before they can represent your products in market? How do channel partners change the internal structure and resource allocation for a company? What mistakes do people make with these partners?
4.) How does Jay think about when is the right time to build a second product? What were the biggest takeaways from his time at Atlassian on building product suites? How does Jay determine when is the right time to move upmarket into enterprise? How does this change in a world of product-led growth?
5.) Why did Jay decide now was the right time to move into venture with Bond? For what reasons did Jay choose Bond, over all the other firms? What have been the biggest surprises for Jay from his first 100 days in venture? What have been the most challenging elements? How did Jay embrace the common challenge of building the conviction to write the first check?
Jay’s Favourite Book: The River Why
Jay’s Most Recent Investment: Sentry
Tony Xu is the CEO and Co-founder of DoorDash, the company empowering merchants to grow their businesses by offering on-demand delivery, data-driven insights, and better in-store efficiency. Prior to their IPO in December 2020, Tony raised over $2.5Bn for DoorDash from some of the best including Sequoia, Coatue, Softbank, Kleiner Perkins and DST, to name a few. Before co-founding the business in 2013, Tony worked in Product at Square, led special projects for the CEO and CFO at eBay, and began his career at McKinsey and Company.
1.) How did Tony make his way into the world of startups and what was that founding a-ha moment for Tony with the founding of DoorDash? What were Tony's biggest takeaways from seeing his parents work ethic at such a young age? How did it impact his operating mentality?
2.) Leadership Style: What does great leadership mean to Tony today? In what ways has Tony's leadership style changed over the DoorDash journey? How does Tony assess his own persistence and grit? Through what framework does Tony decide what to delegate vs what to control?
3.) Decision-Making & Risk: How does Tony evaluate his decision-making process today? What does Tony mean when he says, "you have to reduce the scope"? How does Tony think about understanding the interplay of different variants in a decision? Through what framework does Tony assess risk today? How has Tony's approach to risk and decision-making changed over time?
4.) Talent Acquisition: What have been Tony's biggest lessons in acquiring the best talent? What has worked well in the past? In what ways have they not acquired talent they should have acquired? What type of talent worked in the early days? How has that changed? Through what framework does Tony decide between a stretch VP and a stretch too far?
5.) Culture & Diversity: How does Tony think through the breakpoints in the scaling of culture? At what points did Tony feel the DoorDash culture was not what he wanted it to be? How did he react to change it? Through what process has Tony measured the success of DoorDash's diversity efforts? Which initiatives have worked? Are there any that have not?
Tony’s Favourite Book: Score Takes Care Of Itself: My Philosophy of Leadership
Eric Glyman is the Founder and CEO @ Ramp, the only corporate card and spend management platform designed to help you spend less. To date, Eric has raised over $390M for the company from some of the best including Thrive, Stripe, Founders Fund, Coatue and Box Group to name a few. Prior to changing the game of spend management, Eric founded Paribus, the price-tracking app that raised seed funding from General Catalyst and Greylock, which was acquired by Capital One in 2016.
1.) Entry to Startups: How Eric made his way into the world of startups with Paribus and how that journey and exit led to his founding the recently minted unicorn, Ramp?
2.) Decision-Making: How does Eric deal with moments of intense pressure as a leader? How does pressure impact Eric's decision-making quality? Through what framework does Eric evaluate his decision-making process today? Why does Eric believe operational velocity is so key to company success? How does Eric determine between being fast vs spending real time on something?
3.) Funding Rounds: Why does Eric believe that "funding rounds are science experiments"? What should founders look to prove or disprove with each round? Why does Eric believe "you should never take the highest price"? What are the downsides? How does it impact employee stock options? Does it change investor sentiment? How does it change customer acquisition through referrals?
4.) The Rise of Crossover Funds: What does Eric make of the rise of crossover funds? In what way does their value differ to the value provided by traditional VCs? How does their communication style differ compared to traditional VCs? Does Eric worry about the signalling risk of having crossover funds invested early? Does Eric believe they will change the landscape of venture?
5.) Board Management: How does Eric analyse his style of board management today? How has it changed over time? Where does Eric believe many founders go wrong when it comes to board management? How can boards be used to bring together the wider team and company? What documents does Eric always prepare for the board?
Eric’s Favourite Book: John Wooden: The Legendary UCLA Coach's Top 20 Quotes