20VC: TripActions CEO Ariel Cohen on The Future of Business and Personal Travel & Layoffs; How To Do Them The Right Way & Maintain Company Culture and Morale

Ariel Cohen is the Founder & CEO @ TripActions, the company trusted by more than 4,000 companies to manage their business travel and expenses. To date, Ariel has raised more than $980M with TripActions from the likes of Lightspeed, Oren Zeev and a16z to name a few. Prior to TripActions, Ariel co-founded StreamOnce, a business multimedia integration platform which was acquired by Jive Software. Prior to StreamOnce, Ariel led Product Management in a senior leadership role at Hewlett-Packard.

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In Today’s Episode You Will Learn:

1.) How Ariel made his way into the world of tech and came to change the way we think about business travel today with TripActions?

2.) What are TripActions doing in their business to be there for their partners, customers and suppliers in the long term? TripActions engaged in layoffs, how did Ariel approach the size of layoff required? What is the right way to do layoffs? How does this change in a remote world?

3.) Given the uncertainty, how does Ariel advise founders to assess and correct their burn and spending? What is a reasonable amount of runway to reserve for? For those hit hard on the demand side, what can they do to build durable defensibility when they can’t scale demand?

4.) How does Ariel view the future of business travel? Does Zoom replace much of the business trips? What will the landscape look like in 3 years? What players will survive? Who will thrive?

5.) From a founder psychology perspective, what has Ariel done to cope in these very challenging times? What has worked? What has not worked? What does Ariel advise founders struggling to cope psychologically? What can investors do to be there for their founders?

Items Mentioned In Today’s Show:

Ariel’s Fave Book: Mr Vertigo

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20VC: 7 Powers: The Foundations of Business Strategy: Deconstructing Economies of Scale, How To Assess True Market Size, Assessing Risk vs Uncertainty, What “Brand As Power” Really Means with Hamilton Helmer, Managing Partner and Chief Investment Officer @ Strategy Capital

Hamilton Helmer is the Managing Partner & Chief Investment Officer @ Strategy Capital a long-only public equity fund that selects securities for investment based on Power Dynamics, a proprietary model of fundamental value, developed by Hamilton over decades of strategy consulting with clients such as Hewlett-Packard, Adobe and more. Hamilton is also the author of one of my favourite books, 7 Powers. If that was not enough, Hamilton is also an Instructor in the Economics Department @ Stanford University.

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In Today’s Episode You Will Learn:

1.) How Hamilton made his way into the world of investing from advising some of the largest tech titans on the planet with Adobe and HP?

2.) What is a strategy mental model? What makes the most effective strategic models? What characteristics do they have? How should founders balance between sticking to models and being willing to change them? What are Hamilton’s biggest takeaways from working with Netflix?

3.) “All strategy begins with invention”, what did Hamilton mean by this? How does Hamilton explain the success of copycats in markets? How does Hamilton separate between first mover and creator? How does Hamilton analyse the transition from startup to pricer with scale economics?

4.) How does Hamilton advise founders to view and approach competition? Why does Hamilton totally disagree with the requirement of being 10x better than your competition? Is product innovation alone enough without brand or business model innovation?

5.) How does Hamilton define “brand”? Is brand an attainable strategy alone or is it the byproduct of something else? How transferable is brand in one category to alternative categories? How does a brand truly know when they have sustainable leverage and power?

Items Mentioned In Today’s Show:

Hamilton’s Fave BookThe Road to Reality: A Complete Guide to the Laws of the Universe, Stardust

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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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: How Roam Research Analyse Product Design, Team-Building, The Future of Collaboration Tools & Applying Tesla Go-To-Market To Roam with Conor White-Sullivan, Founder & CEO @ Roam Research

Conor White-Sullivan is the Founder & CEO @ Roam Research, the tool taking over our industry providing a seamless note-taking tool for networked thought. Prior to founding Roam, Conor founded 2 prior businesses and also worked at HuffPost as a Co-Founder of HuffPost Labs where he reported directly to Arianna Huffington and HuffPost CTO.

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In Today’s Episode You Will Learn:

1.) How Conor’s high school wrestling career taught him “how to win”? What was the founding story with Roam? How does Conor think about when to stay true to vision and persist vs when to give up?

2.) How does Conor think about the product design philosophy they have @ Roam? Conor has said before, “roam is not about taking better notes”, what is Roam about then? How does Conor think about the importance of adding challenge to a product? What does he mean when he discusses the importance of “low floors and high ceilings” with regards to product design?

3.) How would Conor analyse his own hiring and team building philosophy? Why are the two most important traits, “girt and autodidactics”?How does Conor really stress these two characteristics in an interview process? Why does Conor choose to live with the team? What are the benefits of this?

4.) Does Conor believe we are in a phase of bundling or unbundling when it comes to collaboration tools? Does Conor believe we will see large players acquire and consolidate over the coming months? Why does Conor compare Roam more to Google than other collaboration tools?

5.) How does Conor think about go-to-market today? What were some of Conor’s biggest takeaways for bootstrapping for years with revenue from customers? Why is Conor borrowing from the Tesla GTM? What does that really mean in practice?

Items Mentioned In Today’s Show:

Conor’s Fave BookHow to Read a Book: The Classic Guide to Intelligent Reading

As always you can follow HarryThe Twenty Minute VC and Conor 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.

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