Jason Brown is the Founder & CEO @ Tally, the startup that allows you to pay off your credit card debt faster and save money. To date, Jason has raised over $92m for Tally from the likes of Mamoon @ Kleiner, Angela @ a16z, Nikhil @ Shasta and Aileen @ Cowboy just to name a few. As for Jason, prior to Tally, he spent 5 years as the Founder and CEO Kleiner Perkins backed, Gen110. Before that Jason founded Bask, a company providing both technical support and pro-active maintenance.
In Today’s Episode You Will Learn:
1.) How Jason came to change the world of consumer finance with Tally having spent 5 years in the solar financing sector and even a year in venture? Given his prior entrepreneurial activities, does Jason agree with Joe Fernande @ JoyMode that "serial entrepreneurship is overrated"?
2.) Does Jason believe that founders should always be raising? What is the right way to truly determine whether an investor is aligned to your mission? What should you look for in how they behave and speak? How does Jason like to build relationships with investors pre-term sheet? Is Jason concerned by the compressed fundraising timelines today?
3.) Why does Jason believe that VC funded companies are largely not over-priced? What elements of the macro-economy does Jason attribute as the reason for the high valuations today? Why does Jason believe that we should not celebrate new fundraising? Is the celebration not good for the morale of the team? What should we celebrate instead?
4.) Why does Jason believe that the target for investors is they provide no value? What are you looking to avoid? What are the core ways an investor can damage the success of a company? What can founders do to truly extract the most from their investor base? Does Jason believe one should focus on the VC partner or the firm? Why?
5.) What does Jason believe makes the best board members? What advice would Jason give to new board members on how they can truly be the best board member? Why does Jason do onboarding sessions for all new board members? What does he look to instil in this process? What behaviour at the board should not be tolerated? How should the founder communicate this to their investor?
Items Mentioned In Today’s Show:
Jason’s Fave Book: Sapiens: A Brief History of Humankind
As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!
Josh Buckley manages a $50m early-stage fund and as an angel has built a portfolio that includes the likes of Clearbit (Chairman), Rippling, Boom Supersonic, Lattice, Embark and many more incredible companies. Josh is also the Founder & Chairman @ Mino Games, the gaming studio he scaled to $20m in annual revenue and raising $40m in funding for the company.
In Today’s Episode You Will Learn:
1.) How did Josh make his way into the world of startups at the age of just 15? How did that lead to becoming the youngest YC founder ever?
2.) What does Josh mean when he says, "the best entrepreneurs are cockroaches"? How does Josh think about capital efficiency today? Does Josh agree with Bill Gurley in stating the biggest challenge today is "the oversupply of capital"? How does Josh advise his portfolio today on raising big rounds? Capital efficiency? Burn rates?
3.) As both a fund manager and founder, what have been some of Josh's biggest takeaways from now investing in 100+ companies as an angel? How has investing impacted Josh's operating mentality? What are the benefits of angel investing? What are the potential dangers? What advice would Josh give to founders entering the world of angel investing?
4.) What are the biggest elements people underestimate when it comes to CAC? What have been Josh's biggest lessons on the volatility of CAC over time? How are we seeing the platforms evolve and develop their tech and pricing? How important is channel diversity to Josh? What is balanced? What is not? What have been Josh's biggest lessons when it comes to payback period and it changing over time?
Items Mentioned In Today’s Show:
Josh’s Fave Blog/ Newsletter: Paul Graham Blog
As always you can follow Harry, The Twenty Minute VC and Josh on Twitter here!
Ash Fontana is a Managing Director @ Zetta Venture Partners, the fund that invests in AI-first companies with B2B business models. As for Ash, prior to Zetta he started the money side of AngelList, where, he launched online investing, created the first startup ‘index fund’. He also ran special projects like AngelList’s expansion into Europe and the UK. Simultaneously, Ash led syndicates and made investments in Canva, Mixmax and others. Before AngelList, Ash co-founded Topguest, a Founders Fund-backed company that built customer analytics technology and was ultimately sold in an 8 figure transaction 18 months after the company was founded.
In Today’s Episode You Will Learn:
1.) How Ash made his way into the world of venture with AngelList and how that led to his joining Zetta today, investing exclusively in AI? What did Ash's time working on his family farm teach him about vertically integrated businesses? What were his biggest takeaways from AngelList and working alongside Naval?
2.) What does AI-first really mean to Ash? How crucial is it for companies to have proprietary datasets today? Are data moats truly defensible and real? What are the 5 characteristics that determine the level of defensibility of a dataset? How does Ash analyse the quality of a dataset? What does Ash do to determine if they are predictive of value?
3.) We often hear the term, "system of record", why is Ash so much more excited by the "system of intelligence"? Why is the basis of competitive advantage shifting from SaaS today as a model? How do the margin structure vastly differ when comparing AI-first companies to SaaS companies? How does that mean one should view capital efficiency?
4.) What does Ash believe drives business model quality? What are the commonalities in the business models of those that have made it big? Why does Ash believe it is difficult for incumbent companies to become AI-first? How difficult is it for incumbents to acquire smaller AI-first firms and integrate their policies and technology?
5.) Why does Ash love Howard marks and what has been his biggest learnings from studying him? How has Ash applied these learnings to his investing today? What has Ash also learned from the Italian masters of design? How has this study helped Ash as a VC? What has Ash optimised lately? What is Ash's favourite optimisation?
Items Mentioned In Today’s Show:
Ash’s Fave Book: The Strategy of Life: Teleology and Mechanics in Nineteenth-Century German Biology
As always you can follow Harry, The Twenty Minute VC and Ash on Twitter here!
Dom Holland is the Founder & CEO @ Fast, the world's fastest login and checkout with no more passwords, no more typing credit card details or shipping addresses. The special announcement today, Fast have just raised their seed round led by Jan Hammer @ Index, joined by Susa Ventures, Kleiner Perkins, Global Founders Capital and then angels including Nick Molnar, Founder @ Afterpay and proud to say I joined the round as an angel also. Prior to Fast, Domm was a Director @ Tap Tins, a network of smart tap-to-donate collection terminals. Domm was also the Founder & CEO @ Tow, an on-demand towing platform which transacted $50m in its first 4 years.
In Today’s Episode You Will Learn:
1.) How Domm made his way from founding an on-demand towing company in Queensland, Australia to founding one of Silicon Valley's hottest new startups in Fast?
2.) What did Domm do in prior companies that worked and he will do again with Fast? What did not work and he will look to avoid? Does Domm agree with Joe Fernandez @ JoyMode in saying, "serial entrepreneurship is overrated"? What advice does Domm give to first-time founders? Where do they most often make mistakes?
3.) Over the last few years we have seen incredible innovation on the merchant side of payments with Stripe and Adyen but why does Domm believe we have seen no innovation on the consumer side? Why have large internet platforms not built it themselves? Does it have to be an independent 3rd party, external to Google, Facebook, Amazon etc?
4.) With the war for talent, rising rents and a lower standard of living, why did Domm choose SF as the base for Fast? How has the move been? What have been the biggest challenges? What would Domm advise founders contemplating moving to SF? How has Domm been able to hire some big hitter valley operators so early on? How does Domm think about equity sharing and optimising ESOP plans?
5.) Jan Hammer @ Index has discussed Domm's work mentality, so how does Domm structure his day? What does Domm do to ensure he optimises every minute? What work habits has Dom found to be most effective? What has not worked? How does Domm think about balancing speed and quality when executing today?
Items Mentioned In Today’s Show:
Dom's Fave Productivity Tool: Superhuman
As always you can follow Harry, The Twenty Minute VC and Domm on Twitter here!
Rick Heitzmann is a Founder and Partner @ Firstmark Capital, one of the leading East Coast venture funds of the last decade with a portfolio including the likes of Airbnb, Pinterest, InVision, Shopify and Discord to name a few. As for Rick, he led the seed round for Pinterest and also led the deals from Firstmark in Ro, Riot Games, Draft Kings, Discord and Airbnb. Prior to founding FirstMark, Rick was an entrepreneur as a founding member at First Advantage which he helped grow and sell to First American (NYSE: FAF). Rick has been recognized by CB Insights and the New York Times as a Top 100 Venture Capitalist globally.
In Today’s Episode You Will Learn:
1.) How Rick made his way into the world of venture and came to found one of NYC's leading venture funds in the form of Firstmark?
2.) How did seeing the booms and bust of the macro impact Rick's investment mentality today? With the impending crash, what 2 things does Rick advise managers need to prepare their portfolio by doing? Does Rick agree with Bill Gurley in saying, "the biggest challenge of today is the over-supply of capital"?
3.) How has Rick seen his style of investing change over the last 20 years? How does Rick think about price sensitivity today? How has that changed over the years? How has Rick seen himself change and evolve as a board member? What does Rick believe makes the best board members? What advice would Rick give to someone who has gained their first board seat?
4.) How does Rick think about the structure of the Firstmark portfolio today? How important does Rick believe it is to have temporal diversification within the portfolio? How does Rick think about optimising investment decision-making processes at Firstmark? Why does Rick believe, despite the negatives, that attribution is fundamentally important?
5.) Does Rick believe that we are in a consumer bubble today? What are the core elements that pique Rick's interest when analysing a consumer investment today? How does Rick think about CAC's scaling way faster and higher than anyone expected? Why does Rick believe the duopoly of FB and Google is now over? Why does Rick believe that true venture size exits can still occur in consumer?
Items Mentioned In Today’s Show:
Rick’s Fave Book: Moneyball: The Art of Winning an Unfair Game
Rick’s Most Recent Investment: Crisp
As always you can follow Harry, The Twenty Minute VC and Rick on Twitter here!
Lisa Edgar is a Managing Director @ Top Tier Capital Partners, one of the leading venture fund of funds over the last decade. Included in their stellar fund portfolio is the likes of Index, Initialized, True Ventures, a16z and Boldstart, to name a few. Prior to Top Tier, Lisa was part of the asset management team at WR Hambrecht + Co focusing on new and emerging private equity funds. Before that, Lisa spent ten years at Horsley Bridge.
In Today’s Episode You Will Learn:
1.) How did Lisa make her way into the world of investing in funds and how did that lead to her becoming Managing Director at one of the leaders, Top Tier?
2.) Lisa has seen the boom and bust of the macroeconomy twice now, how has that impacted her mindset today when investing in funds? What have been the most prominent changes in the venture ecosystem that Lisa has seen over the last 20 years? What changes have been good? What changes have been bad?
3.) What is the best way to get in the room with LPs? Does it have to be through warm intro? What are the signs for the GP that that first meeting went well? If an LP does not respond to emails, does that mean they don't want to do it? How does Lisa and Top Tier structure the investment decision-making process? How does that differ when re-investing in existing managers? Is it worth it for first-time funds to pitch institutions for fund 1 when they know they will not invest in the fund?
4.) How does Lisa think about GP commits today? How does Lisa look at what is reasonable and what is required? Is it individual and context-based? How does Lisa feel about different carry structures? Are kickers when past a certain return profile amenable to LPs?
5.) Lisa has seen some of the best emerging managers in the US over the last decade, what learnings does she have from them in terms of what separates the good from the great? How do they think about partnership dynamics? How do they think about firm culture? How do they think about generational transition?
Items Mentioned In Today’s Show:
Lisa’s Fave Book: From the Mixed-Up Files of Mrs. Basil E. Frankweiler
Lisa’s Most Recent Investment: Boldstart Ventures
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz, one of the leading and most prestigious venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Lyft, Coinbase and many more incredible companies. Ben is also the author of the New York Times bestseller, The Hard Thing About Hard Things, and the upcoming Harper Business book, What You Do Is Who You Are, available October 29. Prior to a16z, Ben was Co-Founder and CEO of Opsware, acquired by Hewlett-Packard for $1.6 billion in 2007. Previously, Ben ran several product divisions at Netscape Communications, including the widely acclaimed Directory and Security product line.
In Today’s Episode You Will Learn:
1.) How did Ben make his way into the world of venture having previously co-founded Opsware? What was the original thinking for a16z? How did seeing the booms and busts of the market as an operator, impact how Ben thinks about investing today?
2.) In the book Ben says, "If soldiers trust the general, communication will be vastly more efficient". What have been Ben's biggest lessons on how to create an environment of trust quickly? As a board member, how does Ben create an environment of trust for the founder? What is Ben's advice to Harry having just gained his first board seat last year?
3.) Ben has said before of the importance of creating "shocking rules". What are the rules for creating these shocking rules? What are the best rules composed of? Given their shocking nature, how does one instil them in the organisation? What does Ben think is the most shocking rule he has implemented at a16z?
4.) What does ben believe that founders can take away from the rituals of the Samurai? Why does Ben believe that "meditating on company downfalls will enable you to build your culture the right way". Why is the negativity so helpful in forming the right culture? How does ben advise founders when their company is struggling, the team knows it and morale is low? What happened at Okta? How did they turn the culture and business around?
5.) Ben has previously spoken about bringing in external leadership from the cultures you want to master. How does one know when is the right time to bring in this external influence? What can we learn from observing Google Cloud's strategy? How does one retain the old culture but augment it with the new? What were some of Ben's biggest hiring lessons when operating? How does Ben get employees to "feel a sense of urgency", when a change needs to occur?
Items Mentioned In Today’s Show:
Ben’s Fave Book: The Black Jacobins: Toussaint L'ouverture and the San Domingo Revolution
As always you can follow Harry, The Twenty Minute VC and Ben on Twitter here!
Steve Huffman is the Co-Founder & CEO @ Reddit, home to thousands of communities, endless conversation, and authentic human connection. To date, Reddit has raised over $550m in funding from some of the world's leading investors including Sequoia Capital, Marc Andreesen, Peter Thiel, Ron Conway, Sam Altman, Josh Kushner, Alfred Lin and Tencent, just to name a few. Steve started his career at Y Combinator as one of their first alumni back in 2005. At YC, Steve co-founded Reddit with Alexis Ohanian, which they sold in 2006 to Conde Naste Publications. In 2010, Steve co-founded Hipmunk, making business travel seamless and easy. Then in 2015, Steve re-joined Reddit as their CEO.
In Today’s Episode You Will Learn:
1.) How Steve made his way into the world of startups and came to be one of the very first ever entrants in the now hailed Y Combinator? How did that lead to the founding of Reddit? Why did Steve return to Reddit, the company he founded, in 2015?
2.) What were Steve's biggest lessons from his journey with Hipmunk when it came to product feedback and iteration? How does Steve assess people's reliance on data today to drive product decisions? Why does he believe 3 criteria must be considered? What are the other two? What time did Steve see the confidence of his own intuition really increase?
3.) How does Steve think about stress management today? What was he like when he was younger in his relationship to stress? What did he actively do to change his relationship to stress? How has Steve seen himself change and develop as a CEO? What have been the inflection points? What has he struggled and also made mistakes in the journey?
4.) What have been Steve's biggest lessons when it comes to hiring truly A* talent at scale? What are the commonalities in the very best hires Steve has made? In the cases of it not working, what does Steve advise founders on the right way to let someone go? How does one do it with efficiency and compassion?
5.) Why does Steve believe that in dense cities, self-driving cars will not be that useful? How does Steve envisage the future of consumer transportation? What does he believe are the alternatives to self-driving cars? How does Steve see the future for the unbundling of social networks? Will they be unbundled into specific communities? How will this look?
Items Mentioned In Today’s Show:
Steve’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Arif Janmohamed is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. Some of Arif's most notable companies that he has led or been involved with for LSVP includel; TripActions, Blend, Nutanix, AppZen, MoveWorks and more. Prior to Lightspeed, Arif worked in the corporate business development team @ Cisco as part of transaction leadership and execution on a number of deals including WebEx. Before WebEx, Arif founded WVP Ventures, a student-run venture capital organization.
In Today’s Episode You Will Learn:
1.) How Arif made his way into venture and came to be one of the valley's leading enterprise investors with Lightspeed?
2.) We are seeing pricing hit 100x ARR multiples, does Arif believe we are seeing enterprise investing as past it's peak? Are we seeing late-cycle momentum investing? Would Arif agree with matt Harris, "Series A pricing does not matter anymore?" How does Arif assess his own price sensitivity today? How has it changed over time?
3.) Why does Arif believe that market risk is the most dangerous risk to underwrite as a VC? How does Arif think about and assess market timing? What has changed over the last few years to unlock such quantums of capital into the enterprise market? With the acquisitions of Duo, Mulesoft, Qualtrics, will we have a next-gen incumbent set or will it be an environment of existing incumbent consolidation?
4.) What does Arif specifically believe founders need to get right when it comes to company design, in order to scale to a $5-10Bn market leader? In terms of the go-to-market, who does Arif think has nailed it most recently? Why? How does Arif test for a founding team's ability to execute on go-to-market when meeting them early on?
Items Mentioned In Today’s Show:
Arif’s Fave Book: Stumbling on Happiness, How Not To Die: Discover the foods scientifically proven to prevent and reverse disease
Arif’s Most Recent Investment: TripActions
As always you can follow Harry, The Twenty Minute VC and Arif on Twitter here!
Roy Bahat is the Head of Bloomberg Beta, one of the leading early-stage funds in the valley and NYC with a portfolio that includes the likes of Flexport, Kobalt, Textio, Rigetti Computing and more incredible companies. Prior to Bloomberg Beta, Roy was the Co-Founder & Chairman @ Ouya, the company that created a new kind of games console and raised over $33m from the likes of Kleiner, Alibaba and even $8.6m on Kickstarter. Before the world of startups, Roy held numerous incredible and fascinating roles including Director of International Strategy at New York's bid for the 2012 Olympic Games and also was a Senior Policy Director in the Office of the May of New York City.
In Today’s Episode You Will Learn:
1.) How Roy made his way from policy director for Mike Bloomberg to entering the world of venture and leading Bloomberg Beta?
2.) What is the big news when it comes to Bloomberg Beta? Roy has previously said, "your fund size is your strategy", what did he mean by this? What does that mean for BB moving forward? How has Bill seen what founders want from their VC change over the last 6 years? How is being "founder-friendly" vs the founder being your "customer" different?
3.) Investment Decision-Making: Does Roy believe that speed is the biggest determinant in winning deals today? What else does Roy believe is crucial? What have been some of Roy's biggest lessons in how to build trust early with founders? How does Roy and BB approach investment decision-making on initial investment? How does this change when it comes to reserve allocation decisions?
4.) Price sensitivity: Roy has said before that, "price is the dependent variable", what does he mean by this? Why is it wrong to assume that the price a VC is willing to pay shows their level of belief in your company? How does fund size change this? How does Roy think about large multi-stage funds playing at seed? How has it impacted seed?
5.) Boards: Why does Roy call boards "b-o-r-e-d-s"? When does Roy think it is important to instil a board? Why is it dangerous to have a board too early in the life of a company? What have been some of Roy's biggest lessons from sitting on a board with Alfred Lin @ Sequoia?
Items Mentioned In Today’s Show:
Roy's Fave Book: Ain't No Makin' It: Aspirations and Attainment in a Low-Income Neighborhood
Roy’s Most Recent Investment: States Title
As always you can follow Harry, The Twenty Minute VC and Roy on Twitter here!
Brianne Kimmel is the Founder and Managing Partner @ Work Life Ventures, a very new firm focused on the future of work backed by some of the best in the valley including Marc Andreesen, Chris Dixon, Zoom's Eric Yuan, InVision's Clark Valberg and then dear friends of the show, Alexis Ohanian, Garry Tan and Matt Mazzeo. To date, Brianne has invested in the likes of Webflow, Tandem, Lunchclub and Girlboss to name a few. Prior to starting Work Life, Brianne spent 2 years at Zendesk on their GTM strategy; building Zendesk for startups, ultimately representing 3,000 startups and 250 accelerators. From 2013-2017 Brianne also taught over 5,000 students at General Assembly all things user acquisition and growth marketing.
In Today’s Episode You Will Learn:
1.) How Brianne made her way into the world of startups and SaaS, how that led to her angel investing and what was that a-ha moment for the founding of Work Life? Why did Brianne choose to structure Work Life as a holding company?
2.) With the fund, how does Brianne think about portfolio construction? What is the right check size for her? Why does Brianne think we are seeing more angel funds than ever today? Why are we seeing so many celebrity names on the cap tables of great companies? How does Brianne think about scout programs? What impact have they had? Why is Brianne against founders actively angel investing?
3.) What does Brianne advise founders on how to structure a high-signal round? What are the two types of angels that exist in the world today? What can founders do to keep their angels actively engaged? How have what founders expect from their angels changed over the last few years? How does one measure the true value of an angel?
4.) Does Brianne agree with Semil Shah, we are seeing "founders vote with their feet and bypass seed funds for multi-stage funds"? How does Brianne advise founders when choosing between a boutique seed firm and a large multi-stage firm? What does Brianne believe are the pros and cons of taking multi-stage money at seed?
Items Mentioned In Today’s Show:
Brianne’s Most Recent Investment: Pace
As always you can follow Harry, The Twenty Minute VC and Brianne on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Rachel Carlson is the Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. To date, Rachel has raised over $71m in funding with Guild from some of the best in venture with the likes of Michael Dearing @ Harrison Metal, Wes Chan @ Felicis, Byron Deeter @ Bessemer, Aileen @ Cowboy Ventures and Scott Raney @ Redpoint, all backing Guild. As for Rachel, prior to Guild, Rachel was the Founder of Student Blueprint, providing students with academic and career planning tools.
In Today’s Episode You Will Learn:
1.) How Rachel made her way into the world of startups having started her career in politics and how insights gleaned from politics formed the idea for Guild Education?
2.) Why does Rachel believe that ambitious Mums are the most under-utilized asset in the economy? What are the biggest misconceptions people have about hiring and working with Mums? How can founders really implement practically facilities, tools and an environment where one can be both ambitious personally and professionally?
3.) Before the show, Byron Deeter @ Bessemer said, "Rachel has been among the best at recruiting star execs across their portfolio”. What have been Rachel's biggest lessons when it comes to hiring the very best talent? Where do most go wrong? How has her hiring style changed over the years? What are Rachel's favourite questions to ask candidates?
4.) Why does Rachel believe that mission and margin are tightly integrated? How did Rachel acquire Walmart as one of their first clients? What are the positives and negatives of having a client so huge, so early? What advice would Rachel have for other early-stage companies when they have such behemoths as clients in the early days?
5.) Why did Rachel make the move from SF to Colorado? What did Rachel strategically do to ensure the chances of success were higher? How does Rachel feel about keeping leadership teams in SF and then the rest elsewhere? How did the move impact their ability to hire the best talent? How did their move impact their ability to access the best capital? Between customers, capital and employees, who is it most important to be near?
Items Mentioned In Today’s Show:
Rachel’s Fave Book: To the End of June: The Intimate Life of American Foster Care, Where The Crawdads Sing
As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
John Fein is the Founder and Managing Partner @ Firebrand Ventures, one of the leading early-stage funds in the midwest with a portfolio including the likes of ScaleFactor, Replica, Dwolla and more fantastic companies. As for John, prior to founding Firebrand, he was the Managing Director of Techstars based in Kansas City and before that spent close to 9 years at OptumRx where he managed multi-billion dollar large-scale programs for the $15B pharmacy benefit manager division of UnitedHealth Group.
In Today’s Episode You Will Learn:
1.) How John made his way into the world of venture from scaling a pharmaceuticals business to almost $2Bn in revenue and how that led to founding Firebrand?
2.) What was it like for John raising the first fund for Firebrand with no existing network of LPs or high-net-worth individuals? How did John approach his closing strategy? How did he decide the amount of money to raise for the fund? How did Techstars Founder, David Cohen change and impact his thinking here? Was John surprised by how long the fund took to raise?
3.) What does John know now that he wishes he had known at the beginning of the fundraise for the first fund? Does it ever get easier? What does John believe are the biggest challenges in managing your own fund? What does he do to mitigate them? How does running your own fund differ from operating in a venture partnership?
4.) "Seed" is so confused in meaning today so what does "seed stage" really mean to John? Does John agree with Harry that we are seeing the eradication of the pre-seed stage? Where does John believe is the ideal insertion point? Does John believe that ownership can be built over time? How does John think about reserve allocation?
5.) How does John think about the relationship-building process with founders? Is John worried by the compressed fundraising timelines we are seeing today? What can investors do to build trust with founders quickly? What signs impress John in the early days of getting to know the founder? What are some common red flags for John?
Items Mentioned In Today’s Show:
John's Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna
John’s Most Recent Investment: The Minte
As always you can follow Harry, The Twenty Minute VC and John on Twitter here!
Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame.
In Today’s Episode You Will Learn:
1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel?
2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here?
3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far?
4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do?
Items Mentioned In Today’s Show:
Jason’s Fave Book: Meditations by Marcus Aurelius
As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Brad Feld is Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio that includes the likes of Zynga, Fitbit, SendGrid and many more incredible companies. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars, the worldwide network of entrepreneurs in 150 countries and 300,000 alumni. Brad is also the co-author of the incredible, Venture Deals, for your chance to win a signed copy email venturedeals@foundrygroup.com with the code "First Episode".
In Today’s Episode You Will Learn:
1.) How Brad made his way into the world of venture following 40 angel checks and how that led to his co-founding Foundry Group? Why did Brad find the transition from angel to VC in the early days such a challenge? What 2 core things did he focus on when writing angel checks? How has that changed now as a VC?
2.) How did seeing the boom and bust of the dot com impact Brad’s investing mindset today? How does Brad think about investing through market cycles and the right way to think about investment cadence? Why does Brad believe that to be successful as a VC you have to be fundamentally optimistic?
3.) Where does Brad believe we are today in the cycle? Does he agree with Bill Gurley on the biggest challenge being the "oversupply of capital"? What must entrepreneurs understand with regards to market cycle dynamics and how they can and need to future-proof their business?
4.) From analysing his best investments, why has Brad come to the conclusion that TAM in the early days is really not helpful? What are the commonalities in how Brad's most successful companies approach experimentation?
5.) What does Brad mean when he says, "don't have fake CEO or fake VC days"? What does he mean when he often says, "run your fucking business"? What in Brad's mind would constitute a "fake day" vs moving the needle for your business? What does Brad think is the best way for VCs to truly get to know one another? Why is, "hey let's do a deal together one of the most hollow and fake statements in venture?"
6.) Brad has sat on some of the most meaningful boards of the last 2 decades, what have been Brad's biggest learnings on what it takes to be a great board member? How does that change with the progression of your career? What advice would Brad give to me, having just gained my first board seat? If the VC does not support the CEO, what is the right process? Why does Brad believe the VC should work for the CEO?
7.) What is Brad's biggest advice when it comes to learning how to say no? What advice does Brad hear most often that he commonly disagrees with? Why does Brad feel we are in a moment of peak noise in the ecosystem today? To be a great leader, what 2 skills does Brad believe you need to have?
Items Mentioned In Today’s Show:
Brad’s Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna, The Moment of Lift: How Empowering Women Changes the World by Melinda Gates
Brad’s Most Recent Investment: Boundless
As always you can follow Harry, The Twenty Minute VC and Brad on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Julia Enthoven is the Founder & CEO @ Kapwing, the startup that provides a new, collaborative platform for creating images, videos, and GIFs. To date they have raised $13m from some dear friends of the show including Saar Guur @ CRV, Mamoon Hamid @ Kleiner Perkins, Niv Dror @ Shrug and Nikhil Basu Trivedi @ Shasta. Prior to founding Kapwing, Julia was an Associate Product Manager @ Google where she worked on everything from image search to sign up workflows.
In Today’s Episode You Will Learn:
1.) How Julia made her way into the world of startups and came to found the future of content editing with Kapwing?
2.) What does Julia believe are the 4 benefits to building a website over an app today? How does this change your development cadence and speed of product iteration? How does this change your economics and margin structure? Where does Julia see many founders making mistakes here?
3.) Why does Julia believe that marketing innovation is as important as product innovation? Kapwing is now at 1m users per month, what has been Julia's biggest lessons in scaling a customer base to this size with very little spend? How does Julia think about marketing channel mortality rate? How should founders approach this?
4.) Why did Julia decide it was better to bootstrap than straight away trying to raise VC dollars? What were the benefits of this? Was it the right decision? What was the turning point when Julia realised was the moment to raise external funding? How did her mindset change as a result of the funding? How does bootstrap life compare to VC funded startup?
5.) How is Julia finding the personal scaling journey from PM to CEO? What have been some of the biggest challenges? What has she done to overcome them? What advice would Julia have for other newly minted CEOs? What have been some of Julia's biggest lessons in what it takes to hire the very best talent early?
Items Mentioned In Today’s Show:
Julia’s Fave Book: Influence: The Psychology of Persuasion
As always you can follow Harry, The Twenty Minute VC and Julia on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Semil Shah is the Founder & General Partner @ Haystack, one of the valley's leading seed funds of the last 5 years with a portfolio including the likes of Instacart, DoorDash, Carta, OpenDoor, Hashicorp and more $Bn companies. Alongside his role at Haystack, Semil is also a Venture Partner @ Lightspeed Venture Partners. Prior to founding Swell, Semil was on the operating side as an early advisor and employee at Concept.io (Swell), acquired by Apple in August 2014.
In Today’s Episode You Will Learn:
1.) How did Semil make his way into the world of venture from his start writing about startups and financing rounds? How did that also lead to his role as Venture Partner @ Lightspeed today?
2.) What does Semil mean when he says, "the most talented founders are bypassing seed firms and seed rounds"? How does this mean that seed funds need to respond? For founders, what are the pros and cons of taking a multi-stage fund at seed? Will they really get GP time with such a small check? How should they also think about potential signalling risk?
3.) Does Semil share Harry's concern with regards to pricing today? What do multi-stage funds investing at seed do to pricing? Why is staying disciplined on price the biggest challenge for Semil? How does Semil assess his own price sensitivity and when to stretch? Does Semil believe that ownership is built on first check or overtime?
4.) How does the strategy for Semil change moving from a $25m fund to a $50m fund? Why does Semil think that temporal diversification is such an important element to bake into a portfolio? What are the benefits? How does Semil think about effective reserve allocation today? What does that investment decision-making process look like the 2nd time?
5.) How has Semil seen the ecosystem for VC fundraises change over the last 5 years? What would Semil like to change about the ecosystem of LPs? What blanket rule does Semil believe that LPs should introduce for new managers to ensure discipline? For Semil, how did the fundraise differ for the latest $50m fund compared to the prior $25m fund?
Items Mentioned In Today’s Show:
Semil’s Fave Book: Reboot by Jerry Colonna
As always you can follow Harry, The Twenty Minute VC and Semil on Twitter her
Alex MacCaw is the Founder & CEO @ Clearbit, the marketing data engine for all of your customer interactions, from customer understanding to prospect identification to personalising every sales and marketing interaction. To date, Alex has raised $17m in financing from some incredible people including Geoff Lewis @ Bedrock, Ash Fontana @ Zetta Venture Partners, First Round Capital, Battery Ventures and then former guest Ilya Sukhar, Naval Ravikant and Josh Buckley. Prior to founding Clearbit, Alex spent time in the engineering teams at both Twitter and Stripe.
In Today’s Episode You Will Learn:
1.) How Alex made his way from the UK to becoming one of the hottest founders in the valley with the rise of Clearbit? What does Alex believe is more important mission and vision or organisational discipline? What does Alex mean when he says he started the company as a "vehicle for growth thinking and self-actualisation"?
2.) What did Alex mean when he said, "when you hit product-market-fit, it is time to move into company making"? What does company making mean to Alex? What would Alex like to fundamentally change about the way we manage companies today? When is the right time to make this transition? What needs to be in place to do it successfully?
3.) What does Alex mean when he says, "The 6 Pillars Behind Clearbit"? What elements does Alex think the team should not have full transparency on? How does Alex approach transparency when it comes to fundraising and M&A opportunities? What have been some of Alex's biggest learnings on both delivering and absorbing feedback? What can one do to create an environment of radical candor and rich feedback?
4.) Why does Alex believe that health has to be the #1 priority for every founder? What does that look like in practice? What can one provide the team to encourage this? How does Alex respond to those that might say, "fine but we cannot afford it"? How does Alex suggest there are 3 ways you can become more self-aware as an individual?
5.) What advice does Alex give to founders on successfully negotiating with investors? What value has Alex found that VCs really do bring? What does Alex optimise for when selecting his investor base? What value do most think that VCs bring but they actually do not? When does Alex think one should establish a board? Why does Alex think your board should only have operators and no investors on it?
Items Mentioned In Today’s Show:
Alex’s Fave Book: The 15 Commitments of Conscious Leadership
As always you can follow Harry, The Twenty Minute VC and Alex on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Ilya Sukhar is a General Partner @ Matrix Partners, the firm steeped in 40 years of history with over $4Bn invested enjoying 110 acquisitions and 65 IPOs. As for Ilya, at Matrix he has led deals in the likes of FiveTran, Flock Safety, Slab and Height just to name a few. Prior to Matrix, Ilya was a part-time investing partner @ Y Combinator and before that was Head of Developer Products at Facebook. His time at Facebook came about as a result of his former company, Parse, being acquired by them for close to $100m in April 2013. If that was not enough, Ilya also has one of the best angel tracks in the business with a portfolio including the likes of former guest Scale, Checkr, Algolia, Airtable, Gitlab the list goes on.
In Today’s Episode You Will Learn:
1.) How Ilya made his way into the world of technology and startups having moved to SF from the Soviet Union? How did his growing up in the Soviet Union and moving to the US shape his thinking, operating and investing mentality today?
2.) How did Ilya's mindset change with the shift from angel investing to institutional investing? How does Ilya assess how his operating experience has impacted the way he works and engages with founders today? What are the pros? What are the cons? Why does Ilya believe the engineering CEO is so crucial?
3.) How does Ilya feel the seed ecosystem is serving startups today? What are the core ways that Ilya believes it is not optimised? How does Ila think about advising founders on the right amount to raise and the appropriate amount of runway? How does Ilya feel on the subject of bridge rounds? How does Ilya approach price and price sensitivity? What have been his learnings on price from observing his angel portfolio?
4.) Why does Ilya believe that "referencing is one of the most important skills for founders and investors"? How should founders structure their referencing? Who should they speak to? How many people is an appropriate dataset? What are the core questions to ask? How can references lead one astray? What must you watch out for?
5.) How has becoming a father changed Ilya's investing mentality today? How has it affected how he selects the projects he wishes to work on? How has it changed his relationship to time and productivity? Why in many ways does Ilya wish he had had kids earlier?
Items Mentioned In Today’s Show:
Ilya’s Fave Book: When Genius Failed: The Rise and Fall of Long Term Capital Management, The Stranger
Ilya’s Most Recent Investment: FiveTran
As always you can follow Harry, The Twenty Minute VC and Ilya on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Alex Wang is the Founder & CEO @ Scale, the data platform for AI providing high-quality training and validation data for AI applications. To date, they have raised over $123m in financing from some of the best investors in the business including Founders Fund, Index Ventures, Thrive, Spark and Coatue and then also some of the world's best operators and founders of Dropbox, Instagram, Quora, Github and Twitch to name a few. Prior to founding Scale, Alexandr was a Tech Lead at Quora, directly responsible for all speed projects and before that a software engineer at Addepar responsible for building and maintaining financial models.
In Today’s Episode You Will Learn:
1.) How Alex made his way from growing up in Los Alamos to being one of the hottest founders in the valley with Scale's new round giving them a unicorn valuation? How did growing up outside the ether of the valley shape Alex's operating mindset today?
2.) Why does Alex believe that AI is under-hyped relative to the state of technology today? Would Alex agree that most projects claiming to be AI are merely rebrandings from actuarial science, data science etc etc? What questions does Alex ask to determine true AI or BS?
3.) How does Alex think about how AI can deal better with ambiguity of data? What other core areas would Alex like to see meaningful step-function improvements in? How does Alex think about the value of data-set size? How does he think about the utility value of data reducing with every incremental data point? How does Alex think about the rise of synthetic data? How does this change the landscape?
4.) What are Alex's biggest lessons on what it takes to hire incredible people before you are a hot company? How does Alex determine whether someone has the right risk profile and desire to work in a startup? What questions reveal that? Where does Alex believe that many go wrong in the early days of hiring? What would he do differently now?
5.) For the $100m Series C, how did the round come together? What did the process look like? How did this round compare to the other rounds? How does Alex think about and approach the element of investor selection? How can founders build relationships with investors in these hyper-compressed fundraising timelines? What have been Alex's biggest lessons when it comes to CEO growth and then also board management?
Items Mentioned In Today’s Show:
Alex’s Fave Book: 7 Powers: The Foundations of Business Strategy
As always you can follow Harry, The Twenty Minute VC and Alex on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Jana Messerschmidt is an investor @ Lightspeed Venture Partners, one of the best performing funds of the last decade with a portfolio including Snapchat, Mulesoft, Max Levchin's Affirm, Cameo, StitchFix and many many more incredible companies. Prior to LSVP, Jana co-founded #Angels in 2015, a first of its kind investment collective specifically designed to get more women on the cap tables of successful companies. Her portfolio includes the likes of Carta, Lambda School, Bird, Forward and Cameo to name a few. In addition to #Angels, Jana spent 6 years at Twitter as VP of Global Business Development and Platform where she led the 150+ person organization responsible for Twitter's global strategic partnerships. Finally, before Twitter, Jana spent 2 years at Netflix as Director of Business Development.
In Today’s Episode You Will Learn:
1.) How Jana made her way from the worlds of Twitter and Netflix to founding #Angels and becoming an angel to today, investing on the front lines with Lightspeed?
2.) What were some of Jana's biggest takeaways from her time with Netflix? How did that experience impact her operating mentality today? How can leaders determine the true quality of their team and their conviction in them? What is "the leaver test"? What does Netflix do internally to drive such high performance? What does Jana mean when she says, "leaders have to provide context, not control"?
3.) Does Jana believe that founders should "always be raising"? What is the right way for founders to approach OKR setting with regards to requirements for the next round? When should this OKR discussion for the next round take place? Who should be involved? How can founders get potential investors to do the work upfront and determine interest?
4.) In terms of metrics for the Series A, they depend based on the vertical and business model but what is required, metric wise, to raise a Series A in:
5.) What tips and advice does Jana give to founders to allow them to enter fundraising negotiations with leverage? What can founders do to gain leverage if their numbers are not in place? What does Jana think should be some of the biggest considerations for founders when it comes to their cap table?
6.) How does Jana think that founders can put their cap table to work in the most effective way? Is there a way to stress their suggested "value-add" prior to their investment? What can be done to actively improve the lack of women and underrepresented minorities on cap tables? What would Jana like to see change here?
Items Mentioned In Today’s Show:
Jana’s Fave Book: Elad Gil's High Growth Handbook, Dark Money
As always you can follow Harry, The Twenty Minute VC and Jana on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Clark Valberg is the Founder & CEO @ InVision, the digital product design platform powering the world's best user experiences. To date, Clark has raised over $350m with InVision from some of the world-leading investors including Iconiq, Spark Capital, Accel, Battery Ventures, Tiger Global, FirstMark and even Atlassian. Prior to founding InVision, Clark spent 8 years as the Co-Founder of Epicenter Consulting, a leading web application design business. If that was not enough, Clark is also a leading angel with a portfolio including Algolia, Voiceflow, Unsplash and BentoBox, just to name a few.
In Today’s Episode You Will Learn:
1.) How Clark made his way from running a successful design agency to fundamentally changing the way designers design products and consumer experience them through InVision?
2.) Why does Clark believe that all aspiring entrepreneurs questions have a false premise? What is the fundamental false premise of entrepreneurship? How does Clark assess the importance of vision and mission over alternate elements? What advice does Clark give to the many aspiring entrepreneurs that ask for his advice?
3.) How does Clark think about market timing today as an entrepreneur? How does Clark think investors should approach and think about market timing? How does Clark look to measure impact not just size of the market? How has angel investing changed Clark's operating mentality as an entrepreneur with InVision?
3.) Why does Clark believe that enlightenment is a daily task? What does Clark do to fundamentally make himself present enough to appreciate those inflection points and moments of enlightenment? How can everyone use note-taking to gain this level of self-consciousness? How are the notes structured? What routine needs to be built around them?
4.) How does Clark think about taking the time to appreciate the milestones that are achieved? Why do we have to make celebrating a ritual? What can be done to ensure these moments of company and personal growth are recognised? What have been Clark's biggest moments of realisation on this theme?
5.) With InVision being an almost fully remote team, what have been Clark's biggest breakthroughs in making it work so well with his marriage and his family? What are "date days"? How does Clark use them to ensure the right balance of work and romance? What has Clark found to be the weirdest thing of operating a 900-person remote firm?
Items Mentioned In Today’s Show:
Clark’s Fave Book: Positioning: The Battle for Your Mind: The Battle for Your Mind
As always you can follow Harry, The Twenty Minute VC and Clark on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Mike Vernal is a General Partner @ Sequoia, one of the world’s leading and most renowned venture firms with a portfolio including WhatsApp, Zoom, Stripe, Airbnb, Github and many more incredible companies. As for Mike he has led and sits on the board of Citizen, rideOS, Rockset, Threads and Houseparty (acquired by Epic). Prior to venture, Mike spent 8 years at Facebook as VP of Product & Engineering leading multiple different teams including Search, Commerce, Profile, and Developer product groups. Prior to Facebook Mike spent 4 years at Microsoft as a PM lead in Microsoft's Developer Division.
In Today’s Episode You Will Learn:
1.) How Mike made the move from VP of Product & Engineering at Facebook to General Partner at the world-famous, Sequoia Capital? What were Mike's biggest takeaways from his 8 years at FB seeing the hyper-growth first hand?
2.) Mike has previously said that he has struggled in the past when it comes to "overthinking investments". What does he mean by this? How does it play out in reality? How does Mike balance between trusting his gut and relying on the data? How does Mike think venture partnerships should participate in this balancing act?
3.) Why does Mike believe decision-making in venture to be fundamentally different to decision-making in operations? How do they compare? How does the decision-making process and approach change as a result of this contrast? How does Mike think about his own time allocation now in venture? What is the most challenging element?
4.) How does Mike evaluate the proliferated SaaS landscape today? Why does Mike believe that the notion of SaaS as a construct will fade over the coming years? What does Mike believe is the reasoning for SaaS apps becoming more and more niche? What problem does that pose for VC? Will we enter a period of consolidation in SaaS? What size do the incumbents have to be to really engage in the M&A process moving forward?
5.) Why does Mike struggle to see the strength of data moats? What are the major downfalls associated with the argument of their strength? At what point is the asymptotic point of the utility value of the data for models today and how does that change over the coming years? What does Mike instead see as durable and sustainable moats?
Items Mentioned In Today’s Show:
Mike’s Fave Book: One Hundred Years of Solitude
Mike’s Most Recent Investment: Verkada
As always you can follow Harry, The Twenty Minute VC and Mike on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Puneet Agarwal is a Partner @ True Ventures, one of the leading early-stage VC funds of the last decade with big wins including Fitbit, Peloton, Ring, Hashicorp, Duo Security and Blue Bottle Coffee, just to name a few. As for Puneet, at True he has led deals in Duo Security, Tray.io, Lumity, Solo.io and more. Before the world of VC, Puneet spent 6 years in product management with Geodesic Securities and BEA. Before product management, Puneet actually cut his teeth in the world of VC as an associate at Mayfield which he joined post a 2-year stint at JP Morgan.
In Today’s Episode You Will Learn:
1.) How Puneet made his way into the world of venture from JP Morgan? How seeing the boom and bust cycle impacted his investing mindset today? How his career in operations led to his joining True?
2.) Why does Puneet believe that EQ is going to separate the good from the great in venture firms over the next decade? What can VCs do to remove the barriers to access them? What have been Puneet's biggest lessons on what it takes to build real relationships of trust and respect with founders? What is a test of a strong founder <> VC relationship?
3.) What does Puneet believe are the 2 feelings a board member can bring to a board meeting? Why would an investor bring fear to the board meeting? Why is this a sign and result of the culture of their own venture partnership? What have been Puneet's biggest lessons on how investors can bring the feeling of safety to a board meeting? How has Puneet changed his style of board membership over the last decade?
4.) Why does Puneet strongly advocate for a venture structure without attribution? What are the benefits of not having attribution? How does this also impact the re-investment decision-making process? How does Puneet think about how he spends his time across the portfolio? What have True done to optimise the investment decision-making process? Why is unanimity not required?
5.) How does Puneet and True think about portfolio construction today? What amount of initial checks give them enough diversification to feel comfortable but also enough reserves to double down? Does Puneet believe that ownership can be built over time? Where does Puneet believe there is a whole in the funding environment? How does True think about minimizing risk on the first check?
Items Mentioned In Today’s Show:
Puneet’s Fave Book: Billion Dollar Whale: The Man Who Fooled Wall Street, Hollywood, and the World
Puneet’s Most Recent Investment: Upsie
As always you can follow Harry, The Twenty Minute VC and Puneet on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Hiten Shah is the Co-Founder @ FYI, the startup that allows you to find your documents in 3 clicks or less. Before FYI, Hiten co-founded QuickSprout alongside Neil Patel, together they scaled the platform to over 500,000 readers every month. Before QuickSprout, Hiten was the Co-Founder and CEO of KISSmetrics, raising over $19m in the process for the company from the likes of True Ventures, Uncork Capital and Felicis Ventures just to name a few. Finally, Hiten is also the Co-Founder @ Crazy Egg, the heat mapping tool used by thousands to improve the effectiveness of their websites. Finally, Hiten is also an angel investor with a portfolio including Buffer, Clearbit, Front, Gusto and more incredible companies.
In Today’s Episode You Will Learn:
1.) How Hiten made his way into the world of startups, growth market and SaaS and how that led to his co-founding FYI today? Having founded multiple startups, does Hiten agree with Joe Fernandez @ JoyMode that "serial entrepreneurship is overrated"? Why does Hiten believe that fundamentally, nobody knows what they are doing?
2.) How does Hiten feel about the compression of fundraising timelines today? How does Hiten advise founders on building authentic relationships with investors? What is it crucial that founders understand about the investing class? How does Chetan advise founders on building hype and urgency within their fundraising? What works? What does not?
3.) Why does Hiten believe that we have seen the eradication of the friends and family round? What other large trends has Hiten observed in the early stage over the last few years? How does Hiten advise founders on how to approach which seed investors they take on board? Does Hiten think founders and investors can be friends?
4.) How has Hiten seen himself change and evolve as a leader over the last decade? What have been the biggest learnings on what great leadership really means? What are the 5 core elements that all great leaders must focus on? How does he split his time across these 5 disciplines? Where do founders often not spend adequate time among the 5?
5.) How does Hiten think about the element of "burnout" and depression today? Has Hiten ever felt burned out himself? How does this stress manifest itself? How does Hiten think that burnout and control are correlated? What can one do to change their relationship to control? What has worked for Hiten? What has not?
Items Mentioned In Today’s Show:
Hiten’s Fave Book: The Courage To Be Disliked
As always you can follow Harry, The Twenty Minute VC and Hiten on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.