20VC: Benchmark’s Sarah Tavel on Why Chasing GMV Will Lead To The Wrong Direction, The 2 Crucial Tipping Points For Marketplace Adoption, Why UGC Plays Are Like Marketplaces & How To Determine Between Existential and Non-Existential Risk

Sarah Tavel is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many more. As for Sarah, prior to joining Benchmark, she was a General Partner at another globally renowned firm, Greylock, where she led deals in Sonder and Gixo. Pre-Greylock, Sarah was the first PM @ Pinterest where she led three acquisitions, launched Pinterest internationally, and was responsible for closing their $100m Series C financing.

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In Today’s Episode You Will Learn:

1.) How Sarah made her way from being the first PM at Pinterest to being a General Partner at one of the world’s leading venture firms, Benchmark?

2.) What does Sarah mean when she says, “the small things are not the big things”? How does Sarah determine between existential vs non-existential risk? How does this impact the type of board member Sarah is? How has Sarah seen the best board members engage? Who are they?

3.) Why does Sarah believe that in marketplaces, chasing GMV will lead you in the wrong direction? How does Sarah think about good vs great when it comes to 1.) Average order values? 2.) Repeat purchase rates. 3.) NPS? 4.) Net revenue retention? How should they change with time?

4.) In marketplaces, what is a tipping point? What are the 2 crucial tipping points to be aware of? How can marketplaces ensure demand brings further demand? What can they determine from how demand engages with different suppliers? How does Sarah feel about feedback systems?

5.) Why does Sarah believe that UGC plays are like marketplaces? What lessons can be drawn from TikTok to suggest this? How does Sarah think about her biggest lessons when analysing the growth of DoorDash? What do many not see that is important to recognise?

Item’s Mentioned In Today’s Episode

Sarah’s Favourite Book: Pachinko: The New York Times Bestseller

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

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20VC: Alexis Ohanian on Why Now Was The Right Time To Start Seven Seven Six, The 2 Very Distinct Types of Deals In Venture & The Unbundling of Social in 2021

Alexis Ohanian is the Founder @ Seven Seven Six, his new fund which just recently announced their first investment leading the $4M seed round for Dispo. Prior to founding Seven Seven Six, Alexis was the Co-Founder & Managing Partner @ Initialized Capital, where he backed many a unicorn including Ro, Flexport, Patreon, GOAT just to name a few. Alexis is also the co-founder @ Reddit, commonly referred to as the front page of the internet, their latest valuation priced the company at $3Bn.

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In Today’s Episode You Will Learn:

1.) When Alexis left his L Sats to go get waffles, what did he learn about himself? How did that lead to founding Reddit? How did Reddit lead to angel investing? How did that lead to Initialized?

2.) Why did Alexis leave Initialized? Why was now the right time? What worked with Initialized that he has taken with him to Seven Seven Six? What did not work with Initialized that he has learned from? How does he view VC NPS as a result of this and the learnings?

3.) How does Alexis analyse his own relationship to money today? How did his relationship with his mother and her illness impact how he thinks about wealth and happiness? How did he feel when at 22 he sold Reddit? How does he feel about the “keeping up with the Jones'” mentality?

4.) How did having Olympia change how Alexis operates and invests today? How does Alexis define backing projects he would be proud to talk to Olympia about? How does he feel about the type of deals many investors make today?

5.) How did Alexis first meet PG from YC? How did he feel when he heard he believed in him and Steve with Reddit? How did that change how Alexis feels about being the first person to really back someone?

Item’s Mentioned In Today’s Episode

Alexis’ Favourite Book: Superforecasting: The Art and Science of Prediction

Alexis’ Most Recent Investment: Dispo

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

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20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour

Stewart Butterfield is the Founder & CEO @ Slack, the leading channel-based messaging platform, used by millions to align their teams, unify their systems and drive their businesses forward. Prior to their direct listing in June 2019, Stewart raised over $1.3Bn from the likes of Accel, Thrive, Softbank, Kleiner, IVP, T Rowe, GV and a16z to name a few. Prior to founding Slack, Stewart co-founded Flickr, a company he built into one of the largest web services in the world. Due to his many incredible successes, Stewart has been named to the 100 Most Influential People in the World by Time Magazine, and one of the Top 50 Leaders by BusinessWeek.

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In Today’s Episode You Will Learn:

1.) How Stewart made his way into the world of startups and came to found Flickr? What was his founding moment for the Slack journey?

2.) How does Stewart think about and assess his relationship to money? How has it changed over time? What does Stewart believe are the 3 levels of wealth? How does Stewart think about his identity being tied to the company? Is that a challenge? How does he mitigate it?

3.) How does Stewart describe his management style and philosophy today? How has it changed over time? How does Stewart approach reversible vs irreversible decisions? How does Stewart structure post-mortems? Why does Stewart believe effective entrepreneurship is like parkour?

4.) How does Stewart think about and advise on the debate between direct listing, IPO and SPAC? What has been better/worse and different since making the transition to being a public company? What have been some of the biggest surprises?

5.) Why does Stewart believe that for most companies, comprehension is the reason for the lack of adoption and customer acquisition? How does he look to solve that with Slack? What have been their biggest mistakes on messaging and branding?

Item’s Mentioned In Today’s Episode

Stewart’s Favourite Book: Leadership and Self-Deception: Getting Out of the Box, Crucial Conversations Tools for Talking When Stakes Are High, The Courage To Be Disliked

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: Accel’s Dan Levine on The Current State of Seed & Series A, The Rise of Pre-Emptive Rounds, Solo Capitalists and Multi-Stage Funds Entering Seed & Market, People and Product; What To Prioritise?

Dan Levine is a Partner @ Accel, one of the world’s leading venture firms with a portfolio including the likes of Facebook, Slack, Qualtrics, UiPath and Deliveroo. As for Daniel, he actually joined Accel in 2010 before leaving to join Dropbox. At Dropbox, he worked on the platform team helping open the platform to third-party developers and launched and managed many of the company’s developer-facing initiatives. Following Dropbox, he rejoined Accel and has led investments in Scale.ai, Mux, Vercel and Sentry to name a few.

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In Today’s Episode You Will Learn:

1.) How Dan made his way into the world of venture with Accel? How that led to his joining Dropbox? What led to his re-joining Accel 3 years later?

2.) How does Dan assess the current state of the seed and Series A landscape? How does Dan analyse the rise of pre-emptive rounds? How does Dan determine when to lean in and pre-empt vs when not to? What does Dan think is the biggest myth about raising a Series A?

3.) How does Dan analyse multi-stage funds so actively entering seed? What has Accel’s seed portfolio data shown? How many went on to raise a Series A? How many did Accel lead? How many companies died? What is the biggest problem this portfolio presents?

4.) How does Dan analyse the trio of people, product and market? How does Dan approach market sizing? How does Dan approach the risk associated with market timing? What risk is he willing to take? What is he not? When can one stretch on market? When is it a stretch too far?

5.) How does Dan evaluate the rise of solo capitalists? What does he see as the core pros and cons of the model? What are the pros and cons of the partnership model like Accel has? How does Dan evaluate the rise of investor personal brands today? What worries him?

Item’s Mentioned In Today’s Episode

Dan’s Favourite Book: Titan: The Life of John D. Rockefeller, Sr. (Vintage)

Dan’s Most Recent Investment: Altinity

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: Lessons from Investing in Uber and Airbnb, How To Think Through Bundling vs Unbundling, Late Stage Funds Moving Earlier, Early Stage Funds Moving Later& The Mechanics of Venture That Founders Should Know with Derek Zanutto, General Partner @ CapitalG

Derek Zanutto is a General Partner @ CapitalG, Alphabet’s independent growth fund with investments in the likes of Stripe, UiPath, Looker, Robinhood and Lyft to name a few. At CapitalG, Derek has led investments in Collibra, Dataiku and Armis as well as sitting on numerous boards. Prior to CapitalG, Derek spent a decade investing in such companies as Uber, Airbnb, Lynda.com and CAA at investment firms TPG, Hellman & Friedman and GIC.

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In Today’s Episode You Will Learn:

1.) How Derek made his way from the world of TPG and growth equity to being a GP with Alphabet’s independent growth fund, CapitalG?

2.) Does Derek agree with Bill Gurley, “the biggest challenge is the over-supply of capital”? How does Derek see this changing with interest rate changes or lackof? How do interest rate changes impact later stage pricing? How does Derek assess his own relationship to price?

3.) How does Derek approach investments thinking through the bundling vs unbundling lens? What have been some core examples of this over the last decade? How does Derek assess market timing risk? What risks is he willing to take? How does he build a thesis ahead of meeting companies?

4.) What does Derek make of large later stage firms moving earlier and doing Seeds and Series A’s? What do entrepreneurs need to know about these firms? What does Derek think about early-stage firms scaling into multi-stage firms? Why is stage specifity so important?

5.) What are the core economics of venture capital that all entrepreneurs need to understand? How do different GPs and funds have different motivations according to fund size? How do different funds approach carry allocation and fees? Why does this matter to founders?

Item’s Mentioned In Today’s Episode

Derek’s Favourite Book: Sapiens: A Brief History of Humankind

Derek’s Most Recent Investment: Armis

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

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20VC: Zach Weinberg on Whether A Company is a Democracy, The Importance of Ownership, The Rise of Pre-Emptive Rounds, Multi-Stage Funds Entering Seed and How he Approaches Both Risk and Personal Capital Allocation

Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital. Fun fact, 20VC Fund has actually invested with them in 3 companies from Alt, Dooly.ai and Boom Pay. Prior to founding Operator Partners, Zach was the Co-founder/COO of Flatiron Health (acq @Roche for $2b) and before Flatiron Zach co-founded Invite Media (acq @Google for $81m). If that was not enough, Zach has also been an incredibly successful angel in the past with a portfolio including RigUp, Ro, Color, BlueApron and Plaid to name a few.

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In Today’s Episode You Will Learn:

1.) How Zach made his way into the world of startups, came to found Flatiron (acq for $2Bn) and how that led to Operator Partners?

2.) How does Zach analyse his own personal capital allocation? How much in funds? How much in cash, equities, direct, credit etc etc? How does Zach analyse his relationship to money? How has it changed over time? How does Zach evaluate his relationship to risk?

3.) What does Zach make of the rise of pre-empted rounds? When should founders takem them vs reject them? How does Zach feel about multi-stage funds re-entering seed aggressively? How does he advise founders? What are the pros and cons of having multi-stage money?

4.) How does Zach think about the importance of ownership? How does Zach analyse the re-investment decision? How does he approach reserve allocation? How does Zach reflect on his own price sensitivity? How has his relationship to price and ownership changed with time?

5.) How does Zach feel about Brian Armstrong’s piece on employees bringing their own political and external beliefs into the workplace? Why does Zach believe that companies are not a democracy? Why does Zach believe that we do not live in a democracy any longer?

Item’s Mentioned In Today’s Episode

Zach’s Favourite Book: Calling Bullshit: The Art of Skepticism in a Data-Driven World

Zach’s Most Recent Investment: David Energy

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: The Implications of a Biden vs a Trump Administration on Venture and Startups, How The Rise of Rolling Funds, SPACs and Solo Capitalists Will Impact Venture & What We Can Do To Swing the Race Pendulum in VC with Barry Eggers, Founding Partner @ Lightspeed Venture Partners

Barry Eggers is a Founding Partner @ Lightspeed Venture Partners and currently Chair of the National Venture Capital Association (NVCA) Board of Directors. Lightspeed is one of the premier funds of the last decade with homeruns including Snapchat, Affirm, Mulesoft, Nutanix and Stitch Fix. Prior to LSVP, Barry spent close to 6 years as @ Cisco developing Cisco’s initial M&A program and leading the company’s first wave of acquisitions and integrations.

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In Today’s Episode You Will Learn:

1.) How Barry made his way into the world of venture over 20 years ago and how he came to found one of today’s leaders, Lightspeed?

2.) What are the implications of a Biden administration? How does this compare to a Trump administration? What can be done to mitigate the tax concerns around Biden’s policies? How does Barry think about each candidate’s stance on immigration? What are the challenges here?

3.) How will SPACs change the world of venture? What will it take for them to be viewed in the same class as IPOs? Why are they often better than direct listings? How does the rise of solo capitalists change the state of venture? What does Barry make of rolling funds being born?

4.) What does Barry believe we can do to swing the race pendulum in venture? What were Barry’s biggest lessons in taking the Lightspeed partnership from 1 to 10 female partners? How can this be done with ethnic minorities also? What advice does Barry give to his counterpart GPs?

5.) How would Barry describe his own style of board membership? How has it changed over time? How does Barry keep his head in boards with many around him are losing theirs? What advice does Barry give to new board members adopting board seats for the first time?

Items Mentioned In Today’s Show:

Barry’s Favourite Book: Channel Kindness: Stories of Kindness and Community

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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