
20VC's Therapist Thursday: We Are Not All Crushing It All The Time So Let's Stop Pretending, Working Through Challenges of Self-Worth and Self-Doubt & How To Find Joy in the Striving with Nick Mehta, CEO @ Gainsight
Nick Mehta is the CEO @ Gainsight, the leader in all things customer success helping you put your customer at the heart of your business. Last year, as a result of their incredible success, Gainsight was acquired by Vista for a reported $1.1Bn but prior to that had raised over $156M from Lightspeed, Battery, Bessemer, Insight and Bain to name a few. As for Nick, he has been named one of the Top SaaS CEOs by the Software report three years in a row and holds one of the highest Glassdoor approval ratings for CEOs. Prior to Gainsight, Nick was the CEO at LiveOffice, which grew substantially and eventually sold to Symantec. In Today's Episode with Nick Mehta You Will Learn: 1.) When did mental health really become a prominent thought for Nick? When was the first time Nick feels he really showed true vulnerability in leadership? 2.) Self-Worth: Does Nick feel like he is enough? What does he do when he questions himself severely? How does he talk to his wife about these challenging thoughts? Where does Nick believe this comes from? What are the dangers of people-pleasing? How does Nick try and counter people-pleasing in his role as a leader? 3.) Identity: How does Nick think about his own identity when it is so attached to Gainsight? In what ways does he try to detach? What has worked? What has not worked? How have children helped Nick in this way? 4.) Striving: Why does Nick believe that hunger and striving are fundamentally a good thing? How does Nick try and factor gratitude and appreciation into the work and success he experiences? How does Nick encourage this same striving in his children? 5.) Relationship to Money: How would Nick evaluate his relationship to money? How has it changed over time? How does Nick try to imbue the same values he had growing up in his children? Does Nick believe it is possible to "change" your children and have that impact?
15 Juli 202145min

20VC: Jet.com's Marc Lore on How To Assess Human Potential and "The Resume Test", Why Chief People Officer Should be One of Your First Hires and Why We Need a New Type of Venture Capital
Marc Lore is a serial entrepreneur turned investor who's started and sold four companies. Most recently Marc was the President and CEO of Walmart eCommerce US following the sale of his company, Jet.com, to Walmart for $3.3 billion in 2016. Prior to that, Marc founded Diapers.com/Quidsi which sold to Amazon in 2011 for $550 million. As an investor, Marc announced his new venture firm, Vision Capital People, with his co-founder, Alex Rodrigues, earlier this year with $50M of Alex and Marc's own money. Fun fact, in 1996 Marc qualified to be in the US national bobsled team. In Today's Episode with Marc Lore You Will Learn: 1.) How Marc made his way into the startup world, how he came to found Jet.com and what led to his most recent transition to the world of investing? 2.) How does Marc assess human potential? What does he mean when he says "the resume test"? What are the clearest signals of outperformers? What are signs of lack of performance? Why does Marc not believe in referencing? Does Mark start from a position of trust for it to be lost or with none and for it all to be gained? 3.) How does Marc evaluate his relationship to risk and fear? How has it changed over time? What did Marc's wife say when he left his safe job and put all their savings into his new business? What does Marc mean when he discusses finding "Sixth Gear"? How does Marc balance that intensity and ambition with romance and family life? 4.) Why does Marc believe Chief People Officer should be one of your first hires? What are the commonalities of the best Chief People Officers? What does the optimal relationship between CEO and CPO look like? How does Marc test for his core characteristics in interviews? What questions does he ask every candidate? What are the most revealing? 5.) How does Marc think about portfolio construction with the new fund today? Does Marc believe it is possible to take 40%+ of companies without alienating future investors? Is Marc concerned about over-capitalising companies too early? How does Marc think about reserves strategy and concentrating capital into the best companies?
12 Juli 202144min

20VC: CapitalG's Laela Sturdy on The Current State of Growth with Crossover, PE and Hedge Funds All Entering, How To Think Through Upside and Downside Scenario Planning at Growth & The Biggest Challenges Startups Face Post Product-Market-Fit but Pre-Scale
Laela Sturdy is a General Partner @ CapitalG, Alphabet's independent growth fund with investments in the likes of Stripe, UiPath, Looker, Robinhood and Lyft to name a few. As for Laela, she joined CapitalG shortly after inception in 2013 and has led investments in Stripe, Duolingo, Gusto, UiPath and Unqork, to name a few. Prior to CapitalG, Laela was at Google as Managing Director of Emerging Businesses and held leadership roles within YouTube and search. In Today's Episode with Laela Sturdy You Will Learn: 1.) How Laela made her way into the world of venture and came to be a General Partner at Alphabet's independent growth fund, CapitalG? 2.) The Market: With the rise of crossover funds, hedge funds, private equity, all entering growth stage venture, how does Laela analyse the current state of the market? How has the increase in capital supply impacted pricing at growth? How do CapitalG compete in a world where competitors pay 2x the valuation and have different outcome expectations? 3.) Portfolio Construction: Given CapitalG's single LP and evergreen structure, how do CapitalG think about portfolio construction? What is the right level of diversification? How doe CapitalG structure internal investment decision-making? How does this change for re-investments? How do CapitalG think about attribution internally? 4.) Upside and Downside: Given prices being so high, when outcome scenario planning, how does Laela think about good vs great when it comes to multiple expectations? How has this changed over time? On the flip side, how does Laela think about loss ratio at growth today? Has this changed with rounds becoming more and more pre-emptive? 5.) Scaling Unicorns: What are the commonalities in the biggest challenges founders face post-product-market fit but prescaling? What are the clear signs to Laela that a founder is uniquely skilled at hiring? Does Laela agree that the best founders do not need help on hiring? How does Laela feel about the future of venture being services platforms? Item's Mentioned In Today's Episode with Laela Sturdy Laela's Favourite Book: The Great Gatsby Laela's Most Recent Investment: Webflow
8 Juli 202138min

20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
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. In Today's Episode with Jeff Lawson You Will Learn: 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? Item's Mentioned In Today's Episode with Jeff Lawson Jeff's Favourite Book: Made to Stick: Why some ideas take hold and others come unstuck As always you can follow Harry and The Twenty Minute VC on Twitter here!
28 Juni 202146min

20VC: Optimising Investment Decision-Making in Compressed Fundraising Timelines & A Deep Dive on Portfolio Construction, Price Sensitivity and The Importance of Ownership with Mark Mullen, Co-Founder @ Bonfire Ventures
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. In Today's Episode with Mark Mullen You Will Learn: 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? Item's Mentioned In Today's Episode with Mark Mullen Mark's Favourite Book: Undaunted Courage Mark's Most Recent Investment: Topia As always you can follow Harry and The Twenty Minute VC on Twitter here!
24 Juni 202141min

20VC: Rishi Sunak, Chancellor of the Exchequer on Turning the UK Into a Talent Magnet, What Can Be Done To Drive Further Investment in UK Venture & A Breakdown of Morning Routines, Peloton Favourites and Managing Nerves
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. In Today's Episode with Rishi Sunak You Will Learn: 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? Item's Mentioned In Today's Episode with Rishi Sunak Rishi's Favourite Book: Roald Dahl As always you can follow Harry and The Twenty Minute VC on Twitter here!
21 Juni 202130min

20VC: GoPuff's Rafael Ilishayev on How GoPuff Has Been EBITDA Profitable From Day 1; The Unit Economics Behind GoPuff, With Intense Competition What Happens To The Food Delivery Space & What It Takes To Launch, Grow and Maintain New Markets
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. In Today's Episode with Rafael Ilishayev You Will Learn: 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? Item's Mentioned In Today's Episode with Rafael Ilishayev Rafael's Favourite Book: Trillion-Dollar Coach: The Leadership Handbook of Silicon Valley's Bill Campbell As always you can follow Harry and The Twenty Minute VC on Twitter here!
14 Juni 202135min

20VC: Why and How The Best Companies Build Economies Around Themselves, When, Why and How To Build Effective Partner/Channel Networks & The Power of Compounding Growth in SaaS with Jay Simons, General Partner @ Bond
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. In Today's Episode with Jay Simons You Will Learn: 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? Item's Mentioned In Today's Episode with Jay Simons Jay's Favourite Book: The River Why Jay's Most Recent Investment: Sentry As always you can follow Harry and The Twenty Minute VC on Twitter here!
10 Juni 202137min






















