Maynard Webb is truly unique, he has worn 3 different hats and excelled in all of them. First, he is the Founder of The Webb Investment Network, the institutionalisation of his personal investing where he has invested in the likes of Zuora, GOAT, WePay, Okta, PagerDuty and many more incredible companies. He is also a Co-Founder and Board Member at Everwise, the startup that helps companies tailor, scale and run training at enterprise scale. Everwise has raised over $26m in funding from the likes of Sequoia Capital and Canvas Ventures. Finally, Maynard sits on the board of some of the biggest companies of our time including Salesforce and Visa. Previously Maynard was Chairman of the Board of Yahoo!, CEO of LiveOps, and COO of eBay.
In Today’s Episode You Will Learn:
1.) How Maynard made his way into the world of startups and came to invest in his first company, founded by Sequoia's Jim Goetz and how that led to eBay, LiveOps and more?
2.) Does Maynard believe we have an excess supply of capital in the market today? What does Maynard think of the mega $Bn+ funds being raised on a frequent basis? How does this distort pricing in the market? How does Maynard think about his own price sensitivity? What does this mean for his available reserve allocation?
3.) Does Maynard believe that the dominant role of CEO is management upscaling? How does Maynard advise on the transition from manager to inspirational leader? How do the vest best CEOs hire the very best execs? How does Maynard know when a stretch VP is a stretch too far? How should founders determine and approach "bet the company" decisions?
4.) When should a founder start installing their board? What does Maynard believe is the optimal board construction, both in characters and profiles? How has Maynard seen his own style of board membership changed over the years? What are the best board members talk to listen ratios? How can founders create alignment among their board?
5.) What is the right way for founders to deal with "s*** hit the fan moments"? What is the framework to approach this with? Where do many go wrong in their approach? How does one communicate this to the wider team, investors and board? What have been Maynard's biggest personal learnings here from eBay?
Items Mentioned In Today’s Show:
Maynard’s Fave Book: The Better Angels of Our Nature
As always you can follow Harry, The Twenty Minute VC and Maynard on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Sarah Tavel is a General Partner at Benchmark, one of the world’s leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. As for Sarah, Sarah has led Benchmark's investments in and currently sits on the boards of Chainalysis and Hipcamp. Prior to Benchmark, Sarah was a Partner at Greylock Partners, where she led Greylock's investment in Sonder and another (unannounced) company. Before Greylock, Sarah was one of the first 35 employees at Pinterest where she led the company's international expansion and aided in the closing of the Series C financing. Sarah was also the product lead for search, recommendations, machine vision, and pin quality and led three acquisitions as she helped the company scale through a period of hyper-growth.
In Today’s Episode You Will Learn:
1.) How Sarah made her first foray into the world of venture with Bessemer over 10 years ago? How that led to Pinterest and how she came to be a GP at Benchmark today?
2.) Speaking of Sarah's operating career with Pinterest, Pat Grady said on the show "never has the rate of decay on operating experience been greater". How does Sarah think about and respond to this? How has operating made Sarah a strong investor? What are the drawbacks that this operating experience can present for investors?
3.) Moving to evaluation, Andy Rachleff, Founder @ Benchmark said on the show, "good team poor market, market wins; good market, poor team, market wins. How does Sarah think about the balance between founder vs market? Why is going after big markets so hard? What should investors look for in a market with that in mind? How does Sarah determine the right time to open up adjacent markets?
4.) There has never been a greater supply of capital in the market than today, does Sarah believe we have an excess supply today? Does Sarah agree with her Partner, Peter Fenton, "no good deal is too expensive in hindsight"? How does Sarah assess her own price sensitivity? How does it depend on the opportunity? How has it changed over time?
5.) Having 2,5000 hours on boards, how has Sarah seen herself develop and change as a board member? What have been some of the biggest learning curves? What are the commonalities in the very best board members Sarah works with? how doe the best entrepreneurs manage and use their boards effectively?
6.) Why does Sarah think that crypto today is very much like the world of adtech in the early days? How does Sarah think about the requirement for specialisation in the space? WIll this be a game for the specialised crypto funds or can generalist VC funds compete?
Items Mentioned In Today’s Show:
Sarah’s Fave Book: Creating the Kingdom of Ends
Sarah’s Most Recent Investment: Hipcamp
As always you can follow Harry, The Twenty Minute VC and Sarah on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Amol Deshpande is the Co-Founder and CEO at Farmers Business Network, the farmer-to-farmer agronomic information network improving the livelihood of farmers by making data useful and accessible. To date, they have raised a whopping $193m in funding from the likes of Kleiner Perkins, T Rowe, GV, Temasek and more. As for Amol, prior to FBN, he was a Partner @ Kleiner Perkins where he invested in the likes of Harvest Power and Agilyx and before Kleiner, Amol was a Director @ Black River Asset Management.
In Today’s Episode You Will Learn:
1.) How Amol made his way into the world of startups, came to be a Partner @ Kleiner Perkins and then came to change the world of farming with Farmers Business Network?
2.) What were Amol's biggest takeaways from his time with Kleiner? Although important to think really big, how does Amol think about the Peter Thiel School of Thought, starting in a very small niche and expanding? Where does Amol see many founders go wrong when it comes to market size and assessment?
3.) How does Amol believe the very best CEOs hire the very best talent? What core characteristics does Amol look for when adding to his exec team? What are the leading questions and indicators that would excite/concern Amol? Why does Amol believe the smartest people do not always make the best hires? What are the core signs that a stretch VP is a stretch too far?
4.) What is the key to success for founders in building credibility with customers, investors and their board? What is the most challenging element of credibility building? Where does Amol see many founders go wrong and lose credibility today? How does your approach have to alter according to which class of individual you are looking to build with?
5.) How does Amol fundamentally approach the topic of capital efficiency? What does Amol believe is the right way for founders to think about dilution when raising? How does Amol determine when is the right time to raise big and pour fuel on the fire?
Items Mentioned In Today’s Show:
Amol’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln
As always you can follow Harry, The Twenty Minute VC and Amol on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
David Frankel is Managing Partner @ Founder Collective, one of the leading seed funds of the last decade with a portfolio including the likes of Uber, PillPack, Coupang, Hotel Tonight, Venmo, Buzzfeed and many more incredible companies. David himself sits on the board of PillPack, Olo, Adhawk and SeatGeek. Prior to founding Founder Collective, David was the Co-Founder and CEO of Internet Solutions, one of the largest ISP providers in Africa. This led to his entrance into angel investing where he enjoyed immense success investing in the likes of Chris Dixon's Hunch and Alex Rampell's TrialPay, just to name a few.
In Today’s Episode You Will Learn:
1.) How David made his way into the world of startups and angel investing from founding Africa's largest ISP provider and how that led to his founding of Founder Collective?
2.) Does David agree with Andy McLoughlin on the inherent mindset shift required when moving from angel to institutional investor? What does David believe is the key to making a new venture partnership work well in the early days? How was the process between him and Eric Paley? What were some of the core challenges/ highlights and breakthroughs?
3.) What does founder-market fit truly mean to David? Why does David believe it is one of the most crucial elements to look for in all investment opportunities? How was this so perfectly evident in the case of Elliot and TJ @ PillPack? How does David navigate the balance between the perfectness of the fit and the investability of the market?
4.) From watching TJ and Elliot at PillPack, what does David believe the truly special founders do to continuously attract the best talent? When does David believe is the right time to really build out the exec team? How did Elliot and TJ align their scaling of the org chart with the growth of the business so well?
5.) How does David think about the lack of free and open distribution in acquiring new customer in a capital efficient manner today? Why does David believe the companies of the future will be advantaged in distribution? In what shape and form can this advantage take? How does David think about the right time to put the pedal to the metal and aggressively grow?
Items Mentioned In Today’s Show:
David’s Fave Book: Sapiens: A Brief History of Humankind
David’s Most Recent Investment: Adhawk
As always you can follow Harry, The Twenty Minute VC and David on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.
Howard Lerman is the Founder & CEO @ Yext, the company that allows you to control your brand experience across the digital universe. Due in part to Howard's incredible leadership of the firm, Yext went public in April 2017 with an opening price of $11 a share, today the stock price sits at $26.85 and a market cap of $2.65Bn. Prior to the IPO, Yext raised over $117m in VC funding from Insight Venture Partners, IVP, SV Angel and CrunchFund to name a few. As for Howard, Yext is his 4th company and he is also Co-Founder and Chairman of Confide, a leading off-the-record messaging service.
In Today’s Episode You Will Learn:
1.) How Howard made his way into the world of startups and came to Partner with is co-founders to start the now public company that is Yext?
2.) Why must every founder know about Teddy Roosevelt and his "Five Minute Meetings"? Literally, what is the right way to structure these meetings? What one question is the right question to ask? How can a leader look to retain that startup culture and ethos with scale? Why does Howard believe running a global company is like running a country?
3.) What have Howard's biggest takeaways been from studying "John Lennon's Storytelling Trick"? How can founders use this trick both to inspire their team more effectively internally and then to present a better vision for the company, externally?
4.) Howard has said before "fundraising is not an end in itself". Does Howard believe that company financing should be celebrated? How was the IPO process for Howard? From a literal standpoint, how does the process run? How did Howard choose which banks to work with? How did the 10-day roadshow shape up? How did the pricing decision-making process look the night before IPO?
5.) Why does Howard believe it is fundamentally better being a public company? What does "public" status allow you? How does being public introduce a challenge never before seen to founders? Why must founders always examine the motives of the VC behind whether they are pushing them to remain private or go public?
Items Mentioned In Today’s Show:
Howard’s Fave Book: Five Stars: The Communication Secrets to Get From Good to Great
As always you can follow Harry, The Twenty Minute VC and Howard on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Shabih Rizvi is the Founding Partner @ Gradient Ventures, Google’s new AI-focused venture fund, which will invest in and connect early-stage startups with Google’s resources, innovation, and technical leadership in artificial intelligence. Prior to Gradient, Shabih was a Partner at KPCB, where he was actively involved with investments in TrueCaller, Mobcrush, Veem and Ujet. In addition, he helped the firm build their seed program and served as advisor to Flipagram and Victorious. Before KPCB, Shabih founded and led the startup outreach program for Google Play. Prior to Google Play, Shabih worked on the Mobile Apps Lab team which built SMB products. His primary focus was scaling TalkBin (Acquired by Google) to enterprise clients. Shabih joined Google after Google’s acquisition of AdMob, where he was a manager on the Business Development team.
In Today’s Episode You Will Learn:
1.) How Shabih made his way into the world of venture with Kleiner Perkins and how he came to be a Founding Partner @ Google's AI focused venture fund, Gradient? What were Shabih's greatest lessons from working side by side with John Doerr?
2.) Shabih has said to me before "founder relationships and their longevity really matter". What does Shabih mean by this? How has this played out for Shabih in an investing environment? What have been Shabih's subsequent learnings?
3.) How does Shabih identify the "3 buckets" that VCs source from? How does Shabih look to filter through opportunities at scale? What must he see in the deck? What are his quick no's? What is Shabih's framework for saying no both with efficiency and kindness? Why does Shabih believe this is one of the hardest parts of the role?
4.) What does the internal investment decision-making process look like at Gradient? Why do they believe that 2 partner meetings a week is optimal? Prior to that, how does Shabih structure his meetings with founders? Why does Shabih believe it is so important to go to them at their HQ? Should all investors go to the founder?
5.) Why is Shabih a strong believer in the decentralisation of talent away from the valley? What are the primary drivers for this decentralization? How does Shabih think about pricing in different regions? To what extent does it differ wildly? How does Shabih respond to traditional SaaS wisdom that you have to build your SaaS business in the valley?
Items Mentioned In Today’s Show:
Shabih’s Fave Book: Measure What Matters, When Breathe Becomes Air
Shabih’s Most Recent Investment: Scotty.ai
As always you can follow Harry, The Twenty Minute VC and Shabih on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.
Andrew Farah is the Founder & CEO @ Density, the startup that measures real-time occupancy of every room in your office. To date, they have raised over $16m in funding from some great friends of the show in the form of Founders Fund, Mark Suster @ Upfront, Ludlow Ventures, Jason Calacanis, Hiten Shah and Arjun Sethi, just to name a few. As for Andrew, prior to founding Density, he was a Managing Partner @ Rounded, a software development agency & product studio. There, Andrew and the team built the first Density prototype.
In The Show Today:
1.) How Andrew made his way into the world of technology and product with Rounded and came to found the people counter of the next generation in Density?
2.) How does Andrew view the role of super-connectors today? What specific time has a super-connector really moved the needle for Andreq and changed the trajectory of Density? What can one do to first build relationships with these people? What can be done to sustain that relationship and really engage and deepen it?
3.) How does Andrew view the importance of "employee retention" in the ultimate success of a company? Density have never had an employee leave in 4 years, what does Andrew believe they have done right? What has not worked for them? What does he mean when he says, "the best leaders answer employees questions before they are asked"?
4.) What has Andrew found to be the commonalities in the truly special VCs? What do they do that makes them so special? How do they view the world and the assessment of companies that is so right? How does Andrew think about investor selection? Where does Andrew see many founders going wrong with this?
5.) Why does Andrew think that so many hardware startups fail today? What do they consistently underestimate and not understand? What are the core challenges in building a global supply chain? How does one have to think about cost of goods (COG) and unit economics when scaling hardware startups?
Items Mentioned In Today’s Show:
Andrew’s Fave Book: The Idea Factory: Bell Labs and the Great Age of American Innovation
As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Casper, the company that deliver a great night’s sleep at an incredible value. The team of engineers at Casper works nonstop prototyping, collecting data, and engineering what is certainly the most comfortable mattress. The Casper mattress has a unique combination of foams that provide the right pressure relief and alignment, so you feel perfectly balanced and comfortable. Try Casper yourself for 100 nights in your own home – RISK FREE. If you don’t love it, they come pick it up and refund you everything, no questions asked. Go to casper.com to try yours for 100 nights with FREE shipping and returns. Use code 20VC to save $50 on select mattresses today.
Lattice is the #1 people management solution for growing companies and helps companies like Asana, Reddit and Cruise build a strong company culture. With Lattice, it’s easy to launch 360 reviews, share ongoing feedback, facilitate 1:1s, set up goal tracking, and run employee engagement surveys. Lattice is the only solution that combines performance management and employee engagement, so operators can make sure top performers are happy. Lattice is giving away three months of Lattice free to 20VC listeners. Just go to lattice.com/20vc to receive the offer. Build an award-winning culture with Lattice. The #1 people management solution.
Barry Eggers is a Founding Partner @ Lightspeed, one of the world’s leading venture funds with a portfolio that includes the likes of Snapchat, Mulesoft, Affirm, StitchFix, AppDynamics, Nutanix and many more incredible companies. Barry himself has led investments in Snapchat, Metasolv Software (acquired post-IPO by ORCL), Calista Technologies (acquired by MSFT), Arbor Networks (acquired by DHR), Growth Networks (acquired by CSCO). As a result of his incredible success, Barry has been named to Forbes Midas List numerous times. Prior to VC, Barry held executive roles at Cisco Systems where he established many of the company’s largest distribution channels across OEMs, Service Providers, Distributors, and VARs. He also developed Cisco’s initial M&A process and directed the first wave of acquisitions and integrations for the company.
In Today’s Episode You Will Learn:
1.) How Barry made his way from the world of Cisco to the wonderful world of venture and came to found one of the most successful firms of the decade in Lightspeed?
2.) How does Barry break up the development of the venture ecosystem into 3 distinct stages? What does Barry believe have been the positive changes? What does Barry believe have been the negative changes? Does Barry believe there is an excess supply of capital today? Why does Barry believe there are too many first time funds? What is the outcome?
3.) Did Barry always aim to build the multi-stage, multi-geography firm that he has built with Lightspeed, from the start? What have been the fundamental inflexion points for Lightspeed both in the increase in brand value and liquidity to LPs? Why does Barry believe building a firm really is an art? What should managers most look for in their first LPs?
4.) What does Barry believe are the 3 ways a venture firm can fail in a generational transition? How can firms incentivise young partners to see the career path and trajectory ahead? What must the older partners at the firm be willing to do? What have been Barry's biggest lessons in their successful generational transition?
5.) Barry has sat on boards for over 21 years, how has Barry seen himself develop and evolve as a board member over time? What makes a truly functional board? What are the best practices? Who is the best board member Barry has ever sat on a board with? What makes Jim Goetz such a special board member?
Items Mentioned In Today’s Show:
Barry’s Fave Book: Quantum Computing: A Gentle Introduction (Scientific and Engineering Computation)
Barry’s Most Recent Investment: Audius
As always you can follow Harry, The Twenty Minute VC and Barry on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.