20VC: Sarah Kunst on Why There Is Plenty Of Investor Money Still Available, The Megan Markle Effect and How It Impacts Hiring and Talent & Whether GP Commits Prevent Diversity and Inclusion

Sarah Kunst is the Founder and Managing Director @ Cleo Capital with a portfolio including the likes of StyleSeat, Glow Bar and PlateJoy to name a few. Prior to venture, Sarah served as a senior advisor at Bumble where she focused on their corporate VC arm, Bumble Fund, and on the board of the Michigan State University Foundation endowment. If that was not enough, Sarah is also a contributing editor @ Vanity Fair. Due to her success, Sarah has been named a Future Innovator by Vanity Fair and a top woman in VC by Wall St Journal.

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In Today’s Episode You Will Learn:

1.) How Sarah made her way into the world of venture from Bumble and how that led to her founding Cleo Capital?

2.) Does Sarah believe VCs really are still “open for business”? What does Sarah make of all the dry powder sitting on the sidelines? How does Sarah think reserve allocation strategies will change today? Why does Sarah believe another great vintage of funds is to come, as it did in 08′?

3.) What would Sarah most like to change about the world of venture? Does Sarah agree that GP commit expectations prevent diversity in venture? How was the fundraising process for Sarah? How can VCs prove skin in the game without having personal capital?

4.) What is the #1 piece of advice Sarah is giving her founders in these COVID times? How does Sarah advise her founders on approaching the talent market today? How does Sarah advise her founders on burn and capital allocation given COVID?

Items Mentioned In Today’s Show:

Sarah’s Fave BookAttached: Are you Anxious, Avoidant or Secure? How the science of adult attachment can help you find – and keep

Sarah’s Most Recent InvestmentPlanet Forward

As always you can follow HarryThe Twenty Minute VC and Sarah and on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Floodgate’s Mike Maples on 3 Key Breakthroughs Startups Experience in Success, The Rise of Angel and Operator Funds, Multi-Stage Funds Re-Entering Seed Investing and The Insight Development Framework

Mike Maples is a Founder & Partner @ Floodgate, one of the leading early-stage firms of the last decade with investments in the likes of Lyft, Twitch, Twitter, Okta and Sonos to name a few. He has been on the Forbes Midas List since 2010 and was also named one of “8 Rising Stars” by FORTUNE Magazine. Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.)

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In Today’s Episode You Will Learn:

1.) How Mike made his way from founding startups to entering the world of venture and the gap he saw in the market when founding Floodgate?

2.) Mike has previously said, “a startup is not a company, it is a series of breakthroughs”. How does Mike define a breakthrough? What are the 2 most meaningful breakthroughs a startup can experience? Which excites Mike the most to see? How do the best startups scale pre-breakthrough to post-breakthrough?

3.) What are the core ways inflections can create breakthrough opportunities? What were Mike’s learnings on inflections from investing in Lyft? What does Mike mean when he talks about the importance of “backcasting”? What did investing in Twitch teach Mike about forecasting?

4.) How does Mike feel about the rise of operator and angel funds? How does Mike analyse the re-entrance of large multi-stage funds back into seed markets? Does Mike agree with Semil Shah, “founders are voting with their feet and taking multi-stage money at seed”?

5.) As Mike’s peers have all moved into larger funds, Mike did not, why? How does Mike view “fund size as your strategy”? How does Mike think about the centrality of ownership? Does Mike really believe you can concentrate capital into your winners? What are the challenges? Why does Mike feel self-promotion is one of the biggest challenges in VC?

Items Mentioned In Today’s Show:

Mike’s Fave BookSuperforecasting: The Art and Science of Prediction

Mike’s Most Recent InvestmentCommonStock

As always you can follow HarryThe Twenty Minute VC and Mike and on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Mark Cuban on His Relationship To Wealth and Risk, Why Coming Out of The Pandemic Will Be The Best Time In The History of Mankind To Start A Business & Why Silicon Valley Investors Are Like Old Hollywood

Mark Cuban is a serial entrepreneur, investor, and owner of the Dallas Mavericks. His career began with his founding of MicroSolutions, a company he went on to sell to CompuServe in 1990. Then in 1995 Mark co-founded Broadcast.com – streaming audio over the internet. In just four short years, Broadcast.com (then Audionet) was sold to Yahoo for $5.6 billion dollars. Following the acquisition in 2000, Mark acquired the Dallas Mavericks where since his taking over they have competed in the NBA Finals for the first time in franchise history in 2006 – and becoming NBA World Champions in 2011. They are currently listed as one of Forbes’ most valuable franchises in sports. If that was not enough, Mark is also one of ABC’s “Sharks” on the hit show Shark Tank.

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In Today’s Episode You Will Learn:

1.) How Mark made his way into the world of technology and startups having been fired from his first job in sales?

2.) How does Mark evaluate his relationship to wealth and money? How has that changed over time? What advice does Mark have to those that tie happiness and money together?

3.) What does Mark think about Silicon Valley investors today? Why does he believe they and the valley are like Hollywood? Why does Mark believe that if the greatest tech companies of today had been started elsewhere, they would be more successful?

4.) How does Mark evaluate his own investing philosophy today? How does Mark think about price and price sensitivity? Why is Mark so keen to have his investment funded from the cashflow of the business? Does this not narrow opportunity and limit upside? How does Mark evaluate risk today?

5.) Why does Mark believe post-COVID is the single greatest time to be an entrepreneur? What advice would he give to an entrepreneur starting their new business in this time? How would Mark go about the re-opening of society post lockdown?

Items Mentioned In Today’s Show:

Mark’s Fave BookRebooting AI: Building Artificial Intelligence We Can Trust, Healthy Buildings: How Indoor Spaces Drive Performance and Productivity

As always you can follow HarryThe Twenty Minute VC and Mark and on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Framework For Hiring The Best Talent 100% Remotely, Raising $32M From Benchmark and GV Pre-Launch and How To Think Through Capital Efficiency and Runway Today with Jeff Seibert and Wayne Chang, Co-Founders @ Digits

Wayne Chang and Jeff Seibert are the co-founders @ Digits, the company that gives you a complete, real-time understanding of your expenses, all in just a few clicks. To date, Wayne and Jeff have raised over $32M for Digits from some of the best in the business including Peter Fenton @ Benchmark and Jess Verrilli @ GV and then with the most incredible base of angels with the founders from Box, Github, Stitch Fix, Tinder, Gusto and more. Prior to Digits, Wayne and Jeff co-founded Crashlytics, acquired by Twitter for a 9-figure sum in Jan 2013 and then acquired from Twitter by Google in 2017. If that was not enough they are also LPs in some of the world’s most exclusive funds and angels in the likes of Gusto, OpenDoor and SoFi to name a few.

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In Today’s Episode You Will Learn:

1.) How did Jeff and Wayne make their way into the world of tech and startups? How did Wayne crashing a startup dinner start everything for them?

2.) How did Jeff and Wayne’s prior success with Crashlytics impact their operating mindset scaling Digits today? What worked? What did not work? What gets easier with time? What gets harder the second time around?

3.) What have been Wayne and Jeff’s biggest lessons from having a remote team from Day 1? What structure and framework do they use to hire the best remote talent? How does that change at the exec level? How do they think about optimising product management for remote teams?

4.) How would Wayne and Jeff summarise their design philosophy with Digits? Why does Wayne believe “minimalism only favours the designer”? When does it make sense to actually add some complexity to your product?

5.) Digits raised $33M pre-launch, why did they favour this approach? How do they think about when to transition from lean and iterative to aggressive and pouring fuel on the fire? Why did they choose to work with Peter Fenton? How do they think about optimising their angel network?

Items Mentioned In Today’s Show:

Wayne’s Fave BookEnders Game

Jeff’s Fave Book: Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs

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.

20VC: Airtable’s Howie Liu on Potential Consolidation In The Collaboration Tools Market, The Transition From Peacetime To Wartime CEO & How To Make The Move To Remote Work Successful; The Process Beyond The Tools

Howie Liu is the Founder & CEO @ Airtable, the all in one collaboration platform that has taken so much of our ecosystem by storm. To date, Howie has raised over $170M from some of the best in the business including Benchmark, Thrive, Coatue, Caffeinated Capital, Founder Collective, CRV and Freestyle to name a few. Prior to founding Airtable, Howie was the Co-Founder @ Etacts, an automated intelligent CRM that was acquired by Salesforce just 9 months after creation. Howie then led the social CRM product at Salesforce. Fun fact, Howie started his career as an intern at Freestyle Ventures.

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In Today’s Episode You Will Learn:

1.) How Howie made his way from founding Etacts to changing the way we think about databases and spreadsheets today with Airtable? How did Salesforce acquiring Etacts impact Howie’s operating mentality with Airtable?

2.) With the rise of remote work, what have been Howie’s core observations from the last month of the world going WFH? What does it take to succeed? What mistakes have Airtable made in their process of work from home? Why did it not work? What lessons did Howie take from that?

3.) How does Howie think about Airtable’s transition from an application to a platform? What does he perceive as the core challenges in making the transition? What lessons has he learned from studying others who have done it? Why did Howie choose Peter Fenton @ Benchmark to work with?

4.) How has Howie seen himself evolve and scale as a leader over the last few years? What have been the most challenging elements? How does Howie think about which individuals he would like as mentors? How does he determine which advice to ingest vs to reject?

5.) How does Howie analyse the remote work/collaboration tools environment today? Does Howie believe we will enter a period of consolidation with the proliferation of new tools created? Does Howie believe we will see an unbundling in collaboration tools?

Items Mentioned In Today’s Show:

Howie’s Fave BookHard Drive: Bill Gates and the Making of the Microsoft Empire, Spying on Whales

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.

20VC: Upfront’s Mark Suster on COVID Redefining What A Great Company Looks Like and What Valuations Look Like, Why Pay-To-Play Is Back On The Table & Why We Will See The Death of Party Rounds

Mark Suster is the Managing Partner @ Upfront Ventures, one of LA’s leading and largest venture firms with a portfolio including the likes of Bird, GOAT, Maker Studios and Ring.com to name a few. Prior to joining the world of venture, Mark was the founder & CEO of two successful enterprise software companies, the most recent of which was sold to Salesforce.com where Mark became VP, Products. Mark is also the author of one of my favourite industry blogs, Both Sides of The Table.

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In Today’s Episode You Will Learn:

1.) How Mark made his way from founding enterprise companies to joining “the dark side” of venture with his move to Upfront?

2.) How does the current economic landscape change the world of B2B? How will renewals be impacted? How will customers approach discounting? Similarly, how will the world of B2C be impacted by COVID? How does this impact marketing and ad spend?

3.) How does Mark think about reserve allocation today with Upfront? How does that change in the face of COVID? Why does Mark believe this environment will redefine valuations? How should founders respond in the face of heavily changed valuations?

4.) Does Mark believe we will see a graveyard of new venture firms who have deployed too quickly and have too many hungry mouths to feed? How does Mark think about building temporal diversification into the portfolio? How can managers use reserves more intelligently moving forward?

5.) Does Mark agree with the Twittersphere that VCs remain “open for business”? How will we see deal volume impact? How will we see size of transaction impacted? What is the most important role a VC can play today? How will the M&A market also be impacte din the face of COVID?

Items Mentioned In Today’s Show:

Mark’s Fave Book: Disunited Nations: The Scramble for Power in an Ungoverned World

Mark’s Most Recent Investment: Solve

As always you can follow HarryThe Twenty Minute VC and Mark and on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: How To Solve The Chicken and Egg Problem in Marketplaces? How Important Is Differentiated Supply? How To Prevent Leakage? How to Create Marketplace Defensibility and more with Alyssa Ravasio, Founder & CEO @ Hipcamp

Alyssa Ravasio is the Founder & CEO @ Hipcamp, the startup that allows you to book unique camping experiences on over 300,000 campsites, cabins, RV parks, public parks and more. To date, Alyssa has raised over $41M in funding from some of the best in the business including Benchmark, a16z, Brad Feld, Dave Morin, Sam Shank @ Hotel Tonight and more. Prior to founding Hipcamp, Alyssa enjoyed numerous diverse roles including being Director of Sales & Marketing @ Revel Systems to working on International Information and Communication Policy in the US State Department.

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In Today’s Episode You Will Learn:

1.) How Alyssa made her way from the US State Department to founding the game-changer of camping experiences in the form of Hipcamp?

2.) How did Alyssa solve the classic chicken and egg problem for marketplaces in the early days with Hipcamp? How important does Alyssa believe it is for marketplaces to have truly differentiated supply? How does Alyssa think about what it takes to prevent leakage in marketplaces today? How can marketplace founders be strategic in building moats around their business? What works? What does not work when building marketplace defensibility?

3.) How does Alyssa manage the psychology of being CEO? What does Alyssa find to be the most challenging element of the role? What have been Alyssa’s biggest lessons from her last 12 months in the role? How has she seen her style of leadership change and develop over time? How does Alyssa deal with the shit hit the fan moments?

4.) How did Alyssa find the fundraising process for Hipcamp? Why did Alyssa wait 5 years before raising the Series A? What changed in the business that made Alyssa realise then was the right time to raise big? How did the Series B with a16z and Andrew Chen catalyse so fast? Why did Alyssa select the investors she did? What investors did Alyssa not select or not select her that she would also loved to have worked with?

Items Mentioned In Today’s Show:

Alyssa’s Fave Book: The Overstory: Shortlisted for the Man Booker Prize 2018, Uncanny Valley: A Memoir

As always you can follow HarryThe Twenty Minute VC and Alyssa on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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