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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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Now displaying: October, 2019
Oct 28, 2019

Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz, one of the leading and most prestigious venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Lyft, Coinbase and many more incredible companies. Ben is also the author of the New York Times bestseller, The Hard Thing About Hard Things, and the upcoming Harper Business book, What You Do Is Who You Are, available October 29. Prior to a16z, Ben was Co-Founder and CEO of Opsware, acquired by Hewlett-Packard for $1.6 billion in 2007. Previously, Ben ran several product divisions at Netscape Communications, including the widely acclaimed Directory and Security product line.

In Today’s Episode You Will Learn:

1.) How did Ben make his way into the world of venture having previously co-founded Opsware? What was the original thinking for a16z? How did seeing the booms and busts of the market as an operator, impact how Ben thinks about investing today?

2.) In the book Ben says, "If soldiers trust the general, communication will be vastly more efficient". What have been Ben's biggest lessons on how to create an environment of trust quickly? As a board member, how does Ben create an environment of trust for the founder? What is Ben's advice to Harry having just gained his first board seat last year?

3.) Ben has said before of the importance of creating "shocking rules". What are the rules for creating these shocking rules? What are the best rules composed of? Given their shocking nature, how does one instil them in the organisation? What does Ben think is the most shocking rule he has implemented at a16z?

4.) What does ben believe that founders can take away from the rituals of the Samurai? Why does Ben believe that "meditating on company downfalls will enable you to build your culture the right way". Why is the negativity so helpful in forming the right culture? How does ben advise founders when their company is struggling, the team knows it and morale is low? What happened at Okta? How did they turn the culture and business around?

5.) Ben has previously spoken about bringing in external leadership from the cultures you want to master. How does one know when is the right time to bring in this external influence? What can we learn from observing Google Cloud's strategy? How does one retain the old culture but augment it with the new? What were some of Ben's biggest hiring lessons when operating? How does Ben get employees to "feel a sense of urgency", when a change needs to occur?

Items Mentioned In Today’s Show:

Ben’s Fave Book: The Black Jacobins: Toussaint L'ouverture and the San Domingo Revolution

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

Oct 25, 2019

Steve Huffman is the Co-Founder & CEO @ Reddit, home to thousands of communities, endless conversation, and authentic human connection. To date, Reddit has raised over $550m in funding from some of the world's leading investors including Sequoia Capital, Marc Andreesen, Peter Thiel, Ron Conway, Sam Altman, Josh Kushner, Alfred Lin and Tencent, just to name a few. Steve started his career at Y Combinator as one of their first alumni back in 2005. At YC, Steve co-founded Reddit with Alexis Ohanian, which they sold in 2006 to Conde Naste Publications. In 2010, Steve co-founded Hipmunk, making business travel seamless and easy. Then in 2015, Steve re-joined Reddit as their CEO.

In Today’s Episode You Will Learn:

1.) How Steve made his way into the world of startups and came to be one of the very first ever entrants in the now hailed Y Combinator? How did that lead to the founding of Reddit? Why did Steve return to Reddit, the company he founded, in 2015?

2.) What were Steve's biggest lessons from his journey with Hipmunk when it came to product feedback and iteration? How does Steve assess people's reliance on data today to drive product decisions? Why does he believe 3 criteria must be considered? What are the other two? What time did Steve see the confidence of his own intuition really increase?

3.) How does Steve think about stress management today? What was he like when he was younger in his relationship to stress? What did he actively do to change his relationship to stress? How has Steve seen himself change and develop as a CEO? What have been the inflection points? What has he struggled and also made mistakes in the journey?

4.) What have been Steve's biggest lessons when it comes to hiring truly A* talent at scale? What are the commonalities in the very best hires Steve has made? In the cases of it not working, what does Steve advise founders on the right way to let someone go? How does one do it with efficiency and compassion?

5.) Why does Steve believe that in dense cities, self-driving cars will not be that useful? How does Steve envisage the future of consumer transportation? What does he believe are the alternatives to self-driving cars? How does Steve see the future for the unbundling of social networks? Will they be unbundled into specific communities? How will this look?

Items Mentioned In Today’s Show:

Steve’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan

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.

Oct 21, 2019

Arif Janmohamed is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. Some of Arif's most notable companies that he has led or been involved with for LSVP includel; TripActions, Blend, Nutanix, AppZen, MoveWorks and more. Prior to Lightspeed, Arif worked in the corporate business development team @ Cisco as part of transaction leadership and execution on a number of deals including WebEx. Before WebEx, Arif founded WVP Ventures, a student-run venture capital organization.

In Today’s Episode You Will Learn:

1.) How Arif made his way into venture and came to be one of the valley's leading enterprise investors with Lightspeed?

2.) We are seeing pricing hit 100x ARR multiples, does Arif believe we are seeing enterprise investing as past it's peak? Are we seeing late-cycle momentum investing? Would Arif agree with matt Harris, "Series A pricing does not matter anymore?" How does Arif assess his own price sensitivity today? How has it changed over time?

3.) Why does Arif believe that market risk is the most dangerous risk to underwrite as a VC? How does Arif think about and assess market timing? What has changed over the last few years to unlock such quantums of capital into the enterprise market? With the acquisitions of Duo, Mulesoft, Qualtrics, will we have a next-gen incumbent set or will it be an environment of existing incumbent consolidation?

4.) What does Arif specifically believe founders need to get right when it comes to company design, in order to scale to a $5-10Bn market leader? In terms of the go-to-market, who does Arif think has nailed it most recently? Why? How does Arif test for a founding team's ability to execute on go-to-market when meeting them early on?

Items Mentioned In Today’s Show:

Arif’s Fave Book: Stumbling on HappinessHow Not To Die: Discover the foods scientifically proven to prevent and reverse disease

Arif’s Most Recent Investment: TripActions

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

Oct 18, 2019

Roy Bahat is the Head of Bloomberg Beta, one of the leading early-stage funds in the valley and NYC with a portfolio that includes the likes of Flexport, Kobalt, Textio, Rigetti Computing and more incredible companies. Prior to Bloomberg Beta, Roy was the Co-Founder & Chairman @ Ouya, the company that created a new kind of games console and raised over $33m from the likes of Kleiner, Alibaba and even $8.6m on Kickstarter. Before the world of startups, Roy held numerous incredible and fascinating roles including Director of International Strategy at New York's bid for the 2012 Olympic Games and also was a Senior Policy Director in the Office of the May of New York City.

In Today’s Episode You Will Learn:

1.) How Roy made his way from policy director for Mike Bloomberg to entering the world of venture and leading Bloomberg Beta?

2.) What is the big news when it comes to Bloomberg Beta? Roy has previously said, "your fund size is your strategy", what did he mean by this? What does that mean for BB moving forward? How has Bill seen what founders want from their VC change over the last 6 years? How is being "founder-friendly" vs the founder being your "customer" different?

3.) Investment Decision-Making: Does Roy believe that speed is the biggest determinant in winning deals today? What else does Roy believe is crucial? What have been some of Roy's biggest lessons in how to build trust early with founders? How does Roy and BB approach investment decision-making on initial investment? How does this change when it comes to reserve allocation decisions?

4.) Price sensitivity: Roy has said before that, "price is the dependent variable", what does he mean by this? Why is it wrong to assume that the price a VC is willing to pay shows their level of belief in your company? How does fund size change this? How does Roy think about large multi-stage funds playing at seed? How has it impacted seed?

5.) Boards: Why does Roy call boards "b-o-r-e-d-s"? When does Roy think it is important to instil a board? Why is it dangerous to have a board too early in the life of a company? What have been some of Roy's biggest lessons from sitting on a board with Alfred Lin @ Sequoia?

Items Mentioned In Today’s Show:

Roy's Fave Book: Ain't No Makin' It: Aspirations and Attainment in a Low-Income Neighborhood

Roy’s Most Recent Investment: States Title

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

Oct 14, 2019

Brianne Kimmel is the Founder and Managing Partner @ Work Life Ventures, a very new firm focused on the future of work backed by some of the best in the valley including Marc Andreesen, Chris Dixon, Zoom's Eric Yuan, InVision's Clark Valberg and then dear friends of the show, Alexis Ohanian, Garry Tan and Matt Mazzeo. To date, Brianne has invested in the likes of Webflow, Tandem, Lunchclub and Girlboss to name a few. Prior to starting Work Life, Brianne spent 2 years at Zendesk on their GTM strategy; building Zendesk for startups, ultimately representing 3,000 startups and 250 accelerators. From 2013-2017 Brianne also taught over 5,000 students at General Assembly all things user acquisition and growth marketing.

In Today’s Episode You Will Learn:

1.) How Brianne made her way into the world of startups and SaaS, how that led to her angel investing and what was that a-ha moment for the founding of Work Life? Why did Brianne choose to structure Work Life as a holding company?

2.) With the fund, how does Brianne think about portfolio construction? What is the right check size for her? Why does Brianne think we are seeing more angel funds than ever today? Why are we seeing so many celebrity names on the cap tables of great companies? How does Brianne think about scout programs? What impact have they had? Why is Brianne against founders actively angel investing?

3.) What does Brianne advise founders on how to structure a high-signal round? What are the two types of angels that exist in the world today? What can founders do to keep their angels actively engaged? How have what founders expect from their angels changed over the last few years? How does one measure the true value of an angel?

4.) Does Brianne agree with Semil Shah, we are seeing "founders vote with their feet and bypass seed funds for multi-stage funds"? How does Brianne advise founders when choosing between a boutique seed firm and a large multi-stage firm? What does Brianne believe are the pros and cons of taking multi-stage money at seed?

Items Mentioned In Today’s Show:

Brianne’s Most Recent Investment: Pace

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

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

Oct 11, 2019

Rachel Carlson is the Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. To date, Rachel has raised over $71m in funding with Guild from some of the best in venture with the likes of Michael Dearing @ Harrison Metal, Wes Chan @ Felicis, Byron Deeter @ Bessemer, Aileen @ Cowboy Ventures and Scott Raney @ Redpoint, all backing Guild. As for Rachel, prior to Guild, Rachel was the Founder of Student Blueprint, providing students with academic and career planning tools. 

In Today’s Episode You Will Learn:

1.) How Rachel made her way into the world of startups having started her career in politics and how insights gleaned from politics formed the idea for Guild Education?

2.) Why does Rachel believe that ambitious Mums are the most under-utilized asset in the economy? What are the biggest misconceptions people have about hiring and working with Mums? How can founders really implement practically facilities, tools and an environment where one can be both ambitious personally and professionally?

3.) Before the show, Byron Deeter @ Bessemer said, "Rachel has been among the best at recruiting star execs across their portfolio”. What have been Rachel's biggest lessons when it comes to hiring the very best talent? Where do most go wrong? How has her hiring style changed over the years? What are Rachel's favourite questions to ask candidates?

4.) Why does Rachel believe that mission and margin are tightly integrated? How did Rachel acquire Walmart as one of their first clients? What are the positives and negatives of having a client so huge, so early? What advice would Rachel have for other early-stage companies when they have such behemoths as clients in the early days?

5.) Why did Rachel make the move from SF to Colorado? What did Rachel strategically do to ensure the chances of success were higher? How does Rachel feel about keeping leadership teams in SF and then the rest elsewhere? How did the move impact their ability to hire the best talent? How did their move impact their ability to access the best capital? Between customers, capital and employees, who is it most important to be near?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: To the End of June: The Intimate Life of American Foster CareWhere The Crawdads Sing

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

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

Oct 7, 2019

John Fein is the Founder and Managing Partner @ Firebrand Ventures, one of the leading early-stage funds in the midwest with a portfolio including the likes of ScaleFactor, Replica, Dwolla and more fantastic companies. As for John, prior to founding Firebrand, he was the Managing Director of Techstars based in Kansas City and before that spent close to 9 years at OptumRx where he managed multi-billion dollar large-scale programs for the $15B pharmacy benefit manager division of UnitedHealth Group.

In Today’s Episode You Will Learn:

1.) How John made his way into the world of venture from scaling a pharmaceuticals business to almost $2Bn in revenue and how that led to founding Firebrand?

2.) What was it like for John raising the first fund for Firebrand with no existing network of LPs or high-net-worth individuals? How did John approach his closing strategy? How did he decide the amount of money to raise for the fund? How did Techstars Founder, David Cohen change and impact his thinking here? Was John surprised by how long the fund took to raise?

3.) What does John know now that he wishes he had known at the beginning of the fundraise for the first fund? Does it ever get easier? What does John believe are the biggest challenges in managing your own fund? What does he do to mitigate them? How does running your own fund differ from operating in a venture partnership?

4.) "Seed" is so confused in meaning today so what does "seed stage" really mean to John? Does John agree with Harry that we are seeing the eradication of the pre-seed stage? Where does John believe is the ideal insertion point? Does John believe that ownership can be built over time? How does John think about reserve allocation?

5.) How does John think about the relationship-building process with founders? Is John worried by the compressed fundraising timelines we are seeing today? What can investors do to build trust with founders quickly? What signs impress John in the early days of getting to know the founder? What are some common red flags for John?

Items Mentioned In Today’s Show:

John's Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna

John’s Most Recent Investment: The Minte

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

Oct 4, 2019

Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame.

In Today’s Episode You Will Learn:

1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel?

2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here?

3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far?

4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Meditations by Marcus Aurelius

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

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

 
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