20VC: Biggest Lessons From Opendoor’s Scaling Journey, How To Implement Systems for Growth & The Right Way To Structure Customer Discovery Processes with Julia DeWahl, Angel Investor

Julia DeWahl is one of the rising stars of the Silicon Valley angel investor community with a portfolio including the likes of Linear (Sequoia-backed), Modern Fertility (USV backed) and Primer (Founders Fund backed). Prior to angel investing Julia was one of the first 10 employees at Opendoor seeing their hyper-growth first hand in many different roles from Head of Seller Experience to being General Manager of Pheonix & City Operations. Before Opendoor, Julia spent 3 years as a consultant at Bain. If that was not enough, Julia is also an avid cyclist and is setting up a women’s cycling apparel line alongside her investing.

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In Today’s Episode You Will Learn:

1.) How Julia made her way into the world of startups with Opendoor from Bain and how that position at Opendoor led to her angel investing? What were the 1-2 takeaways for Julia from her time at Opendoor that have most impacted how she angel invests today?

2.) Customer Discovery: When is the right time to engage in deep customer discovery work? How does one select the customers to go deep with? How does Julia structure the process? What questions are most revealing? Where do many go wrong? How does one determine the feedback to accept vs which to reject?

3.) How does Julia think about implementing systems for growth? What is the structure of these systems? Where does one start? How does Julia determine the metrics to track and focus on? How does Julia balance between growth vs profitability?

4.) Does Julia believe people can really scale with the company? What are the leading indicators that people are struggling to scale with the company? How does Julia advise generalists to survive and thrive in a scaling organisation? Should they specialise?

5.) What have been some of Julia biggest lessons of what it takes to be successful as an angel today? Who has Julia learned and gained the most from in this new discipline? How does Julia measure her own success as an angel? What are the core challenges?

Items Mentioned In Today’s Show:

Julia’s Fave BookThe Courage To Be Disliked: How to free yourself, change your life and achieve real happiness

Julia’s Most Recent Investment: Primer: Homeschool with superpowers

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: Oren Zeev on Why Diversification Is Overrated, The Downside of Thematic Investing, Making Quality Decisions In Uncertain Conditions & Why He Has No Reserves Allocation

Oren Zeev is the Founding Partner @ Zeev Ventures, one of the best and most under the radar firms in the early stage Silicon Valley landscape. Over the past decade, Oren has backed the likes of TripActions, Tipalti, Audible, Houzz, Chegg and Hippo Insurance to name a few. Prior to crushing it with Zeev Ventures, Oren spent 12 years as a General Partner @ Apax Ventures, starting in Israel and then moving to the US where he headed the Technology Practice of Apax and the Silicon Valley office.

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In Today’s Episode You Will Learn:

1.) How Oren made his way into the world of venture with Apax and how that led to his founding his own firm, Zeev Ventures?

2.) Having been in a venture partnership, why did Oren want to be a solo GP? What are the benefits? How does it change decision-making? What are the downsides? How does Oren discuss deals and ideas without partners? How does Oren explain the decision to LPs on being a solo GP?

3.) Why does Oren not believe in thesis-driven investing? What are the dangers and downsides to it? Why do most managers still do it then? Why does Oren specifically look for under-appreciated markets? How is pricing and competition different there? How does Oren assess his own price sensitivity?

4.) Why does Oren think that diversification is overrated? How does Oren think about cross-fund investing? Why is it such a strength that managers should use? Why do many not do it? How does Oren think about reserve allocation? Why is he the only VC to not have a reserves strategy?

5.) How does Oren think about fund deployment timelines? Why do LPs not like the annual fundraising approach? How does Oren size up his position in companies over time and round? How does Oren feel about founders taking secondaries?

Items Mentioned In Today’s Show:

Oren’s Fave BookThe Last Lion: Winston Spencer Churchill: Defender of the Realm

Oren’s Most Recent Investment: Treeverse

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: How Fundraising For Funds Has Changed in The World of COVID, The Benefits of Managers Selling Part of Their GP & How To Think Through Your “Minimum Viable Fund Size” with Lo Toney, Founding Managing Partner @ Plexo Capital

Lo Toney is the Founding Managing Partner @ Plexo Capital, a very unique firm making both direct investments and fund investments. They have invested in Precursor, Boldstart, Female Founders Fund and WorkBench on the fund side and then PlayVS, Replicated and StyleSeat on the direct side. Prior to Plexo, Lo was a Partner @ GV (Google Ventures) and before that was a Partner with Comcast Ventures where he led the Catalyst Fund. Before venture Lo was an operator enjoying exec roles at Zynga, Nike and eBay.

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In Today’s Episode You Will Learn:

1.) How Lo made his way into the world of venture with GV and how that led to his innovating on the venture model investing in both funds and directly with Plexo today? What were Lo’s biggest takeaways from his 5 years as a Partner @ GV?

2.) How will GPs raising today be impacted by COVID? How does this differ dependent on the stage they invest and the size of fund they are raising? How does Lo advise managers communicating with existing and new potential LPs today?

3.) What does Lo mean when he discusses your “minimum viable fund size”? How does Lo advise GPs when it comes to closing strategies? How much do they need for first close? How many closes should there be thereafter? Should they take the money when it is on the table?

4.) How does Lo feel about anchor LPs taking/investing in the GP? What are the benefits for the manager of doing so? Why does Lo believe there is such a binary view towards it? Why does Lo disagree with the benchmarks set of what a GP commit “should be”?

5.) Why does Lo believe we will see the hybridization of GP/LP over the coming years? What are the benefits of having your LP also direct invest? What are the core challenges to the model? How does Lo envisage the world of venture evolving over the next decade?

Items Mentioned In Today’s Show:

Lo’s Fave BookWhy Should White Guys Have All the Fun?: How Reginald Lewis Created a Billion-Dollar Business

Lo’s Most Recent Investment: PlayVS

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: Andrew Wilkinson on Building The Berkshire Hathway of Tech, Sustainable vs Unsustainable Growth and The Relationship Between Money and Freedom

Andrew Wilkinson is the Managing Partner @ Tiny, a vehicle that buys, builds and invests in wonderful internet companies. Within their family of companies is Dribble; home to the world’s best design professionals; MetaLab and Supercast to name a few. Tiny does also make venture investments in the likes of Superhuman, SpaceX, Pitch and Buffer. Today Andrew oversees a group of companies with over 300 employees and tens of millions in revenue.

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In Today’s Episode You Will Learn:

1.) How Andrew made his way from founding a design agency in Canada to starting Tiny and building a family of companies with over 300 people?

2.) What does Andrew mean when he says, when buying companies he looks for companies like New Zealand? What qualities/features do they have? How does Andrew think about price sensitivity when acquiring these companies? What determines paying a premium price to Andrew?

3.) How does Andrew assess and analyse true defensibility within company strategies today? Why does Andrew not believe they will lose any companies? How does Andrew think about grow vs profitability? Are they mutually exclusive? When does one pour fuel on the fire and raise big?

4.) How has Andrew seen himself develop and change as a leader over the last 5 years? What does truly great delegation look like? What is Andrew’s biggest weakness? What is his biggest insecurity? How does Andrew think about sink the boat vs non-sink the boat decisions?

5.) Does Andrew believe we will see the unbundling of social networks moving forward? What are the core characteristics that determine whether a social network will win? Why does Dribble have defensibility as a brand against all large incumbents?

Items Mentioned In Today’s Show:

Andrew’s Fave Book: Tao of Charlie Munger: A Compilation of Quotes from Berkshire Hathaway’s Vice Chairman

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: Craft Ventures’ David Sacks on How To Assess Founder Psychology, How To Accurately Evaluate CAC, Burn and Churn & What Makes The Very Best Startup Boards

David Sacks is the Co-Founder @ Craft Ventures, one of Silicon Valley’s leading early-stage funds with David’s portfolio including the likes of Facebook, Tesla, SpaceX, Palantir, Affirm, Airbnb, Slack and Bird to name a few. David started his career in tech as the first product leader and COO @ Paypal, growing payment volume from $0-$500M per month, leading to their $1.5Bn acquisition by eBay. David then founded Geni.com, creating a family tree for the whole world, the company was acquired 3 years later by MyHeritage. David then founded Yammer, the secure solution for internal corporate communication and collaboration, acquired by Microsoft for $1.2Bn. Finally, David then became COO and Interim CEO @ Zenefits before starting Craft.

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In Today’s Episode You Will Learn:

1.) How David made his way from founding Yammer to creating one of the valley’s newest and most prestigious firms in Craft Ventures? Given David’s operating success he could have angel invested continuously, why decide to start a fund? What does he ultimately want to achieve with Craft?

2.) How did experiencing the Dot Com Bubble with Paypal and then 2008 impact David’s investing and operating mindset? Does David believe VCs really are “open for business” today? How is VC behaviour shifting when comparing early to later stage? How is Craft responding?

3.) Unit Economics: How does David assess unit economics in early-stage opportunities he is looking to invest in? What does proper attribution look like? Where do many go wrong with unit economics? Is it too early to try and assess unit econ at seed? How does David think about having mental plasticity towards unit economics, recognising how they change over time?

4.) Customer Acquisition: Does David agree with Peter Fenton, “there is a complete lack of free and open distribution”? What are the rules of thumb on CAC that David does and then does not agree with? How does David feel about blended CAC? What separates good from great when it comes to CAC/LTV?

5.) Churn: How does assess net negative churn in the businesses he works with? What is great, good, decent and poor? How does avid think about logo vs dollar retention? How does David advise founders who feel COVID has not impacted churn for them? What should they expect?

6.) Burn + Capital Efficiency: How does David analyse burn and capital efficiency today? What does he mean when he discusses “the burn multiple”? How should the burn multiple change with the stage of the business? How does David advise founders on how aggressively to cut burn today?

Items Mentioned In Today’s Show:

David’s Fave BookThucydides’ Trap

David’s Most Recently Announced Investment: Sourcegraph

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: Substack Founder Chris Best on The Future of Public Journalism, Why The Economics Of Attention Have Been Flipped & Why Micropayments For Content Will Not Work

Chris Best is the Founder & CEO @ Substack, the company that makes it simple for a writer to start a paid newsletter. To date, Chris has raised over $17M in funding from the likes of a16z, Y Combinator, Twitch CEO Emmett Shear and Zynga Co-Founder Justin Waldron to name a few. Prior to founding Substack, Chris was the Co-Founder & CTO @ Kik, letting users connect with friends, groups and the world around them. The company raised over $220M in funding from Spark, Tencent and USV to name a few.

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In Today’s Episode You Will Learn:

1.) How Chris made his way into the world of startups and came to found Kik? How his journey with Kik led to his founding Substack?

2.) During COVID, traditional media publications have been hit hard and Substack has taken off, how does Chris see the correlation there? Given the public journal of record has always been free, how does Substack interact with public news? What does Chris

3.) Why does Chris believe that micropayments are a fundamentally bad idea? Structurally why would they not work? Does Chris agree the biggest problem consumers face today in content is one of discovery? Why not?

4.) When designing the Substack product today, how does Chris think about incentive design? Why does Chris believe with incentives, Substack is the opposite of Twitter from a product perspective? Why have the “economics of attention now been flipped?”

5.) How has Chris seen himself evolve and change as a leader over the last 3 years? What advice would Chris give to CTOs making the move into the role of CEO? What does Chris believe his greatest strengths and weaknesses are as a leader? How does Chris find the war for talent today?

Items Mentioned In Today’s Show:

Chris’ Fave BookThe Death and Life of Great American Cities

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: Lightspeed Partner, Merci Victoria Grace on The Future of Collaboration Tools, Bundling vs Unbundling, Synchronous vs Asynchronous & What It Means To Productise The S*** Out of Venture

Merci Victoria Grace is a Partner @ Lightspeed Venture Partners, one of the valley’s leading venture firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Affirm, AppDynamics and more. As for Merci, prior to entering the world of venture, Merci spent 3 years at Slack including as Head of Growth where she grew the growth team to over 50 people and drove DAU’s from 500K to 5M in under 2 years. Merci is also the Founder of Women In Product a global community of incredible women in product management.

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In Today’s Episode You Will Learn:

1.) How Merci made her way into the world of venture having led the growth team at Slack for close to 3 years?

2.) Merci has been working to productise venture, so what core elements of venture need productising? What systems and tools has Merci put in place to create a product around these processes and methods? What have been the biggest challenge in the attempt to productise VC?

3.) How does the decision-making process look like at Lightspeed? How does Merci use post mortems to help her improve post having lost a deal? How does she structure those post-mortems? What have been some of the core takeaways? What internal tech stack does LSVP run itself on?

4.) How does Merci see the future of the collaboration tools market? Are we entering a period of bundling or unbundling? How does Merci feel about the debate between synchronous and asynchronous? How does Merci determine between those who have grown sustainably vs unsustainably in the time of COVID?

5.) Why do the majority of collaboration tool startups fail? What do they get so wrong in their go-to-market? For those that succeed, what are the commonalities in those that succeed? Why is being good at Twitter a competitive advantage? How does Merci feel about the Superhuman, high touch onboarding style?

Items Mentioned In Today’s Show:

Merci’s Fave BookNever Split The Difference: Negotiate As If Your Life Depended on It

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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