20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward

Adrian Aoun is the Founder & CEO @ Forward, a health care system combining world-class doctors with advanced technology to empower patients to take control of their health. To date Adrian has raised funding from some of the true greats of the business including Marc Benioff, Eric Schmidt, Joe Lonsdale, Aaron Levie and Josh Kushner, to name a few. As a result of the incredible work at Forward, they were named to TIME’s Best Inventions of 2017. Before Forward, Adrian was the head of special projects for the CEO of Google/Alphabet and Adrian arrived at Google following the acquisition of his artificial intelligence (AI) company, Wavii. Adrian is also a prolific angel with the likes of WorkRamp, Atrium, Convoy and more in his incredible portfolio.

In Today’s Episode You Will Learn:

1.) How Adrian made his way from selling Wavii to running special projects for the CEO @ Google, to now changing the Continue reading "20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward"

20VC: Why The Days of Spray and Pray at Seed Are Over, How To Compete In A World of Sequoia Seed Funds & Why Price Doesn’t Matter with Dan Scheinman, Angel Investor @ Zoom & Arista Networks

Dan Scheinman is one of the West Coast's leading angel investors with a portfolio including the likes of Zoom.us, Tango.me, TomFoolery (acquired by Yahoo) and Arista Networks, where he also sits on the board. Prior to angel investing, Dan spent 18 years at Cisco in numerous roles including Senior Vice President of Corporate Development where he rebuilt corp dev as a growth enabler for Cisco. Dan was also the Senior Vice President and General Manager of the Cisco Media Solutions Group (CMSG), an internal startup which successfully developed and marketed a hosted software.

In Today’s Episode You Will Learn:

1.) How Dan made his way into the world of angel investing following leading the M&A and Corp Dev teams at Cisco?

2.) Why does Dan believe that the days of spray and pray angel investing at seed are over? What does the re-entrance of large funds like Continue reading "20VC: Why The Days of Spray and Pray at Seed Are Over, How To Compete In A World of Sequoia Seed Funds & Why Price Doesn’t Matter with Dan Scheinman, Angel Investor @ Zoom & Arista Networks"

20VC: 3 Questions Founders Must Stress Test VCs with, What Separates the Good From The Great VCs & Why 80% of VC Detract Value From Board Meetings with Seth Sternberg, Founder & CEO @ Honor

Seth Sternberg is the Founder & CEO @ Honor, the startup that provides homecare your family will love. To date Seth has raised over $60m in funding with Honor from the likes of Thrive Capital, a16z, Homebrew and 8VC. Prior to Honor, Seth was the Co-founder & CEO of Meebo, a web communications platform backed by the likes of Sequoia, Khosla and True Ventures. Meebo reached $50M in revenue and close to half of the US internet population before being acquired by Google for $100M in 2012. At Google, Seth became a Product Director working on the Google+ Platform and GoogleX. Seth is also a prolific angel investor with a portfolio including the likes of Fitbit and Gusto to name a few.

In Today’s Episode You Will Learn:

1.) How Seth made his way into the world of startups with the founding of Sequoia backed, Meebo? How did he transition from social network to Continue reading "20VC: 3 Questions Founders Must Stress Test VCs with, What Separates the Good From The Great VCs & Why 80% of VC Detract Value From Board Meetings with Seth Sternberg, Founder & CEO @ Honor"

20VC: Why Crypto Is The Biggest Disruptor To Hit VC In A Decade, The State of Crypto Today & Why Investing In Decentralized Platforms Requires A New Mental Model with Boris Wertz, Founding Partner @ Version One Ventures

Boris Wertz is the Founding Partner @ Version One Ventures, one of North America's leading early-stage funds with a portfolio including the likes of previous guests Coinbase, AngelList, Shippo, TopHat, Polychain Capital and many more incredible companies. As for Boris, prior to VC, Boris was the COO @ Abe Books, where he led a team of 60 people until their acquisition in 2008 by Amazon. In addition to this, Boris is also a Board Partner with a16z and the lead independent director @ Ether Capital, a Toronto-based technology company aiming to become the central investment hub for the Ethereum ecosystem.

In Today’s Episode You Will Learn:

1.) How Boris made his way from creating the largest European marketplace for used books to becoming one of North America's leading investors with Version One?

2.) How does Boris analyze where we are at now in the development and hype cycle of Continue reading "20VC: Why Crypto Is The Biggest Disruptor To Hit VC In A Decade, The State of Crypto Today & Why Investing In Decentralized Platforms Requires A New Mental Model with Boris Wertz, Founding Partner @ Version One Ventures"

20VC: Hims’ Andrew Dudum on The Scaling Playbook of The Fastest Growing Mens Wellness Brand, How To Be Truly Innovative In Today’s World of Online Marketing & Raising at a $200m Valuation within Year 1

Andrew Dudum is Co-Founder & CEO @ Hims, the fastest growing men’s health and wellness brand that has raised over $45m in VC funding from some of the best in the business including Thrive Capital, Forerunner Ventures, IVP, Redpoint and SV angel just to name a few. Andrew is also co-founder and General Partner at Atomic, a venture-builder backed by Peter Thiel, Marc Andreesen and many of the world’s best investors. Prior to Atomic and Hims, Andrew led Product at TokBox.com, the leader in web-based communication. In 2012 TokBox was acquired by the global telecommunications company Telefonica ($TEF).

In Today’s Episode You Will Learn:

1.) How Andrew made his way into the world of startups, came to build a venture builder backed by Thiel and Andreesen before starting the fastest growing men's health and wellness brand in Hims?

2.) How does Andrew view the world of online and Continue reading "20VC: Hims’ Andrew Dudum on The Scaling Playbook of The Fastest Growing Mens Wellness Brand, How To Be Truly Innovative In Today’s World of Online Marketing & Raising at a $200m Valuation within Year 1"

20VC: Andy McLoughlin on The Benefits of Backing Unsexy Businesses with Non-Obvious Founders, How To Distinguish Between A Good Bridge Round and A Bridge To Nowhere & Whether VCs Really Do Add Value?

Andy McLoughlin is Partner @ Uncork Capital, formerly SoftTech and one of the leading early-stage funds on the West Coast. In their incredible portfolio, they have the likes of Fitbit, SendGrid, PostMates, Front, PoshMark, Eventbrite and many more. As for Andy, he loves to invest in "unsexy ideas" with stellar teams and has led deals in the likes of Postmates, LaunchDarkly, Human Interest (previously Captain 401), and Focal Systems just to name a few. Prior to VC, Andy co-founded Huddle, an enterprise collaboration platform which raised more than $80M in venture funding before its acquisition in 2017. Andy also has a stellar angel portfolio with the likes of Buffer, Intercom and Pipedrive all angel investments.

In Today’s Episode You Will Learn:

1.) How Andy made the transition from Founder of one of the UK's hottest startups to one of the leading early-stage VCs in Silicon Valley?

2.) Why did Softtech decide Continue reading "20VC: Andy McLoughlin on The Benefits of Backing Unsexy Businesses with Non-Obvious Founders, How To Distinguish Between A Good Bridge Round and A Bridge To Nowhere & Whether VCs Really Do Add Value?"

20VC: Why VCs Are Wrong About Bootstrapped Founders, How Content Can Be Used As A Key Customer Acquisition Tool & How To Use Humour When “S*** Hits The Fan” with Jesse Genet, Founder & CEO @ Lumi

Jesse Genet is the Founder & CEO @ Lumi, the startup that is used by thousands of e-commerce companies to get world-class packaging at unbeatable prices. To date, Jesse has raised close to $10m in VC funding from some of the best in the business and old friends of the show including Satya @Homebrew, Kirsten @ Forerunner, Spark Capital, Lowercase, Ludlow and more incredible names. Prior to Lumi, Jesse founded Inkodye, a bootstrapped business that Jesse scaled to 7 figures in revenue and was sold in retail stores around the world.

In Today’s Episode You Will Learn:

1.) How Jesse made her way into the world of startups and VC having bootstrapped her prior business to 7 figures in revenue and being sold in 1,500 stores?

2.) Given that Lumi is Jesse's first VC backed business, does this make Jesse a first-time founder? How did the bootstrapping to 7 Continue reading "20VC: Why VCs Are Wrong About Bootstrapped Founders, How Content Can Be Used As A Key Customer Acquisition Tool & How To Use Humour When “S*** Hits The Fan” with Jesse Genet, Founder & CEO @ Lumi"

20VC: Why Follow-On Investments Are Always A Better Investment, Why Spray and Pray Investing Is Like The Stock Market & Why Startups Need A Board From Day One with Jerry Neumann

Jerry Neumann is one of New York's leading angel investors with a portfolio including the likes of The Trade Desk (IPO: 2016), Datadog and Flurry (acquired by Yahoo) just to name a few. Prior to angel investing, Jerry built the first open market for the pricing and exchange of real-time consumer data in the form of Root Markets. Jerry was also the Managing Director @ Omnicom's Venture Capital Division where he enjoyed an incredible 5 IPOs from the portfolio.

In Today’s Episode You Will Learn:

1.) How Jerry made his way into the world of VC in the 90s and why it was difficult to lose money in venture at that time?

2.) Why does Jerry believe that the vast portfolio construction model is "wrong" and a "dead end"? In what circumstances does Jerry believe "spray and pray" investing can work? Why does Jerry believe you can only have as many companies Continue reading "20VC: Why Follow-On Investments Are Always A Better Investment, Why Spray and Pray Investing Is Like The Stock Market & Why Startups Need A Board From Day One with Jerry Neumann"

20VC: Why Your Board Are Right 50% of The Time, Biggest Lessons From Being Mentored By Reed Hastings & Raising $130m in Funding and The Balance Between Growth and Capital Efficiency with James Reinhart, Founder & CEO @ ThredUp

James Reinhart is the Founder & CEO @ ThredUp, the world's largest online thrift store, and consignment store. To date, ThredUp has raised over $130m in VC funding from many friends of the show including Tim @ Redpoint, Patricia @ Trinity, Eric @ Founder Collective and Ian @ Goldman Sachs just to name a few. As for James, prior to ThredUp he was a Goldsmith Fellow in Social Enterprise at HBS and a Bill George Fellow at the Center for Public Leadership at the Kennedy School. Before that, James co-founded Beacon Education Network, a charter management organization serving low-income students on California's Central Coast.

In Today’s Episode You Will Learn:

1.) How James' childhood dream of being an architect changed to founding the world's largest online thrift store?

2.) Tim Hale @ Redpoint: "James is one of the most naturally talented leaders I have ever worked with". So what does great leadership Continue reading "20VC: Why Your Board Are Right 50% of The Time, Biggest Lessons From Being Mentored By Reed Hastings & Raising $130m in Funding and The Balance Between Growth and Capital Efficiency with James Reinhart, Founder & CEO @ ThredUp"

20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learning The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS.

In Today’s Episode You Will Learn:

1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there?

2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the Continue reading "20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learning The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne"

20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS.

In Today’s Episode You Will Learn:

1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there?

2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the Continue reading "20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne"

20VC: Thumbtack’s Marco Zappacosta on The 3 Core Elements To All Board Meetings, Raising $250m from Sequoia and Why You Have To Win Supply Side Acquisition First For Marketplace Success

Marco Zappacosta is the Founder & CEO @ Thumbtack, the startup that allows you to find local professionals for pretty much anything. To date, Thumbtack has raised over $270m in funding from some of the very best including Sequoia Capital, CapitalG (Google Growth), Ali and Hadi Partovi, Scott and Cyan Banister and Jason Calacanis. Due to Marco's incredible success scaling Thumbtack to helping millions of Americans today, he has been recognized by Forbes as 30 under 30 and Thumbtack was recently acknowledged as one of GlassDoor’s best places to work.

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In Today’s Episode You Will Learn:

1.) How Marco made his way into the world of startups and came to create one of the most prominent marketplaces of the day in Thumbtack?

2.) What does Marco mean when he says "founders must treat board members as employees"? How does Marco view the Continue reading "20VC: Thumbtack’s Marco Zappacosta on The 3 Core Elements To All Board Meetings, Raising $250m from Sequoia and Why You Have To Win Supply Side Acquisition First For Marketplace Success"

20VC: How a16z Uses NPS To Create Better Founder Experiences, Why Intellectual Curiosity Is The Most Important Investor Trait & Creating A Fund To Last Through The Ages with Zal Bilimoria, Founding Partner @ Refactor Capital

Zal Bilimoria is Founding Partner @ Refactor Capital, one of Silicon Valley's newest entrants to the early stage scene with a $50m fund looking to back founders solving fundamental human problems. Prior to co-founding Refactor, Zal was a Partner @ a16z where he co-led investments in Omada Health, Branch.co, AltSchool, Honor, and more, while helping to launch the firm's Bio Fund. Before becoming an investor, Zal spent 10 years as a PM at Microsoft, Google, Netflix, and LinkedIn. He worked on emerging markets for Windows, became one of the first monetization team members at YouTube, and then  became the 1st Head of Mobile at Netflix and helped start the Sales Solutions business at LinkedIn.

In Today’s Episode You Will Learn:

1.) How Zal made his way into the world of VC with a16z from the very corporate worlds of Microsoft, Google, Netflix and LinkedIn?

2.) What were Zal's 3 biggest learnings Continue reading "20VC: How a16z Uses NPS To Create Better Founder Experiences, Why Intellectual Curiosity Is The Most Important Investor Trait & Creating A Fund To Last Through The Ages with Zal Bilimoria, Founding Partner @ Refactor Capital"

20VC: Why You Have To Raise $100m+ If You Want To Go Big Today, The 5 Fundamentals To Starting and Scaling A Successful Marketplace & Why Female Founders Under-Promise and Over-Deliver with Paul Hsiao, Founding Partner @ Canvas Ventures

Paul Hsiao is a Founding Partner @ Canvas Ventures, one of Silicon Valley's leading and newer entrants to the Series A scene. At Canvas, Paul has made investments in the likes of Everwise, Fluxx Labs, Roofstock, Thrive Global, Transfix, and Zola. Before founding Canvas, Paul was a partner at NEA, where he led an early-stage investment in Houzz, as well as, had the privilege of helping eight companies go public on the NYSE or NASDAQ and seventeen companies with successful M&A exits during his 10-year tenure with the firm. Prior to VC, Paul was an entrepreneur with the founding of Mazu Networks, a pioneer in network security that was acquired by Riverbed Technologies.

In Today’s Episode You Will Learn:

1.) How Paul made his way into the world of VC with NEA and got Scott Sandell as his first mentor in VC?

2.) Question from Oren Zeev: Having been a partner at both, Continue reading "20VC: Why You Have To Raise $100m+ If You Want To Go Big Today, The 5 Fundamentals To Starting and Scaling A Successful Marketplace & Why Female Founders Under-Promise and Over-Deliver with Paul Hsiao, Founding Partner @ Canvas Ventures"

20VC: Why Facebook Will Be The Company To Succeed in Crypto, Why Founders Should Be Actively Angel Investing & Commonalities of Great Leadership From Mark Zuckerberg to Mark Pincus with Darian Shirazi, Founder & CEO @ Radius

Darian Shirazi is the Founder & CEO @ Radius, the startup that provides you with not just data but truth allowing you to gain clarity to reach and convert your best B2B prospects. To date, Darian has raised over $105m in VC funding with Radius from some of the very best in the business including our friends at Founders Fund, 8VC, Salesforce Ventures and rockstars like Jared Leto and Charlie Songhurst. Prior to Radius, Darian has enjoyed roles such as first external engineering hire at Facebook and working on the "Sell Your Item" team at eBay. Darian has also made several angel investments in the likes of MessageMe, Sprig and Try.com just to name a few.

In Today’s Episode You Will Learn:

1.) How Darian made his way into the world of tech as Facebook's first ever intern at the age of 17 and how that led to the founding Continue reading "20VC: Why Facebook Will Be The Company To Succeed in Crypto, Why Founders Should Be Actively Angel Investing & Commonalities of Great Leadership From Mark Zuckerberg to Mark Pincus with Darian Shirazi, Founder & CEO @ Radius"

20VC: Greylock’s Jerry Chen on The 2 Fundamentals To Assessing Startup Risk, Why Good Investors Have To Be Optimistic & Why VCs Get In Trouble When They Move Outside Their “Strike Zone”

Jerry Chen is a Partner @ Greylock Partners, one of the world's most successful VC funds with prior investments in the likes of Facebook, Instagram, LinkedIn, AirBnB, Dropbox, AppDynamics, Coinbase and many more incredible companies. As for Jerry, Jerry invests in entrepreneurs building new enterprise SaaS applications and in all aspects of AI and cloud infrastructure. Jerry currently sits on the Board of Docker, Cato Networks, Gladly, Rhumbix, Spoke, and Blend. Prior to joining Greylock, Jerry was Vice President of Cloud and Application Services at VMware where he was part of the executive team that scaled the company from 250 to over 15,000 employees and $5B in revenue. Check out Jerry's recent writing on Risk: The Game of Strategic Investment here.

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In Today’s Episode You Will Learn:

1.) How Jerry made his way into the world of VC with Greylock from being on the Continue reading "20VC: Greylock’s Jerry Chen on The 2 Fundamentals To Assessing Startup Risk, Why Good Investors Have To Be Optimistic & Why VCs Get In Trouble When They Move Outside Their “Strike Zone”"

20VC: Tearing Up Term Sheets and Writing Your Own, Why Founders Must Do “VC Dating” Pre-Fundraise & The Benefits of Capital Constraints in The Early Days with Rachel Drori, Founder & CEO @ Daily Harvest

Rachel Drori is the Founder & CEO @ Daily Harvest, the direct-to-consumer brand that delivers real, unprocessed, unrefined foods in the most convenient format possible: frozen. To date, they have raised over $43m in funding from the likes of former guest Alex Taussig @ Lightspeed, Collaborative Fund and future 20VC guest Beth Ferreira who sits on the board. As for Rachel, prior to starting Daily Harvest, Rachel harnessed her skills as a customer-centric marketing executive, leading teams at Gilt Groupe, American Express, and Four Seasons Hotels and Resorts.

In Today’s Episode You Will Learn:

1.) How Rachel made her way from the corporate world of American Express and The Four Seasons to founding Daily harvest, looking to change the eating habits of millions?

2.) Why did Rachel decide to deliberately raise small Seed and Series A rounds? What does Rachel believe these capital constraints allow companies in the early days? Continue reading "20VC: Tearing Up Term Sheets and Writing Your Own, Why Founders Must Do “VC Dating” Pre-Fundraise & The Benefits of Capital Constraints in The Early Days with Rachel Drori, Founder & CEO @ Daily Harvest"

20VC: How Great VCs Handle Themselves In An M&A Process, Why M&A Has Become The Primary Method of Exit & How The Best M&A Teams Operationalise Their Process with James Loftus, Corporate Development Lead @ Square

James Loftus is Corporate Development Lead @ Square where he has made multiple acquisitions and investments including the likes of acquiring OrderAhead and investing in Eventbrite. Prior to Square, James was responsible for strategy, business development and operations at STX Digital. Before that James was a Partner @ Andreessen Horowitz where he led strategic coverage for the firm’s 45+ consumer-facing portfolio, advising them on everything from capital raising to partnerships to M&A. Prior to VC with a16z, James was VP & Head of Corporate Development @ Yahoo and also spent time in the M&A team at Google.

In Today’s Episode You Will Learn:

1.) How James made his way into the world of corporate development and M&A with Andreessen and how that translated to leading Square's M&A efforts today?

2.) Why does James fundamentally disagree with the notion that "companies are bought and not sold"? What are the nuances behind Continue reading "20VC: How Great VCs Handle Themselves In An M&A Process, Why M&A Has Become The Primary Method of Exit & How The Best M&A Teams Operationalise Their Process with James Loftus, Corporate Development Lead @ Square"

20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy

Dan Lewis is the Founder & CEO @ Convoy, the startup that really is the future of freight with trucking services powered by technology to drive reliability, efficiency and insights. To date they have raised over $80m in funding from some of the world's best-known investors and individuals including Y Combinator Continuity Fund, Greylock, Jeff Bezos, Marc Benioff, Drew Houston, Kevin Systrom and leading angels, Ali and Hadi Partovi. Before Convoy, Dan served as general manager of new shopping experiences at Amazon and spent time at Google and Microsoft in a number of logistics-related roles.

In Today’s Episode You Will Learn:

1.) How Daniel first fell in love with the logistics space as a little boy, made his move into the world of tech with Google and Microsoft and came to found Convoy?

2.) How does Dan truly define the differences between linear and non-linear businesses? Why does Dan believe that startup timing is Continue reading "20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy"

20VC: Finding VC Partners That Look Beyond The Numbers, The Black Box of VC Secrets That Needs To Be Shared & The 1,000 Reasons A VC Won’t Invest In You When It Has Nothing To Do With You with Leah Busque, General Partner @ Fuel Capital

Leah Busque is a General Partner @ Fuel Capital, one of Silicon Valley's leading seed funds with the most incredible portfolio including many previous 20VC guests Ryan @ Flexport, Florian @ Mesosphere, Alex @ Clearbit and Dan @ Convoy (episode Friday). As for Leah, prior to VC, she was a pioneer of the sharing economy with her founding of TaskRabbit, one of the leading online labor marketplaces in the US, raising over $37m in the process before their sale to IKEA last year. Due to this incredible success, Leah has been named to Fast Company's "100 Most Creative People in Business".

In Today’s Episode You Will Learn:

1.) How Leah made her way from sitting on the couch discussing dog food with her husband to founding TaskRabbit and how that translated into the world of VC today?

2.) How did Leah's time in operations affect: