20VC: Matt Mochary, Coach To Silicon Valley’s Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors

Matt Mochary coaches some of the world’s leading venture capitalists and founders helping them to build the best organizations possible. On the VC side, Matt has worked with Peter Fenton @ Benchmark, several Sequoia Partners, Hemant @ GC and Mamoon @ Kleiner to name a few. As for founders, Matt has worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport and more. Prior to coaching, Matt began his business career as an investor with Spectrum Equity Investors.  He then co-founded Totality, eventually sold to MCI/Verizon.  In his own words, Matt went on to have fun (making the Academy Award short-listed documentary Favela Rising) and do good (starting the Mochary Foundation).

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In Today’s Episode You Will Learn:

1.) How Matt made his way from growth investor to immensely successful founder to now coaching the world’s leading investors and founders?

2.) How does Matt advise founders to think about their relationship towards fear and anger? Why doe they generate bad quality of decision-making? What should be done when one recognises they are fearful or angry? Where do many founders and investors go wrong here?

3.) How does Matt advise founders who struggle with issues of self-doubt and imposter syndrome? What process should they go through to gain their confidence? What should they not do? How should they communicate their self-doubt to their team and the world?

4.) How does Matt advise founders in terms of the optimal communication strategy both with their team and their co-founders? Does radical transparency need to be instant or should it be timed correctly? What are the best conflict resolution strategies between founding teams?

5.) Why does Matt believe boards are the death of investors? Why are board members not optimally placed to advise their founders? What does Matt believe makes the best board members having worked with the likes of Peter Fenton? What does Matt advise new board members to be the best board member they can be?

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

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


20VC: Why Most Founders Do Not Structure Their Fundraise Correctly, The Pros Of Having An MBA As A Startup Founder & How To Manage The Psychology Of Being CEO and Overcome Self Doubt with Iman Abuzeid, Founder & CEO @ Incredible Health

Iman @ Incredible Health

Iman Abuzeid is the Founder & CEO @ Incredible Health, the startup that connects hospitals with nurses and other high shortage healthcare professionals to dramatically speed up the hiring process. To date, Iman has raised over $17M with Incredible Health from some dear friends of the show including NFX, a16z, Charles Hudson @ Precursor and Obvious Ventures to name a few. As for Iman, prior to Incredible, she was a medical doctor, a McKinsey alumnus and led product management at AliveCor, a Khosla-backed health tech startup.

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In Today’s Episode You Will Learn:

1.) How Iman made her way into the world of startups from a family of surgeons and then through being a medical doctor herself?

2.) How was the fundraising process for Iman as a female minority founder? What advice would Iman give to other women and/ or minority when it comes to getting the very best investors? Where does Iman see so many founders make mistakes raising? How should founders structure their meetings with VCs?

3.) Where does Iman believe VCs can be most helpful? Where do many think VCs are helpful but they are actually not? What does Iman think of the “VC Twitter” ecosystem at play today? What investors said no along the way but Iman really liked? Why? Why does Iman believe MBA’s provide such an advantage to startup founders today?

4.) How does Iman manage the psychology of being a CEO? How does Iman deal with moments of self-doubt and imposter syndrome? How has Iman seen herself evolve and change as a leader over the last 3 years? What elements have been the most challenging to come to grips with?

5.) Why does Iman still believe if you are not building your startup in the bay, you are missing out? What is so special about Silicon Valley? What advice does Iman give to founders looking to build a diverse team from day 1? How does Iman think about inevitable hiring mistakes? When is the right time to pull the plug?

Items Mentioned In Today’s Show:

Iman’s Fave Book: The Hard Thing About Hard Things

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

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

Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

20VC: Index Ventures Partner, Mark Goldberg on The Questions Founders Must Ask A Multi-Stage Fund Before Taking Their Money At Seed, Why Most Angels Will Lose Their Money & Why We Will See Our First $100Bn Neo-Bank Shortly

Mark Goldberg @ Index Ventures

Mark Goldberg is a Partner @ Index Ventures, one of the leading venture firms of the last decade with a portfolio including the likes of Dropbox, Revolut, Supercell, Plaid and Transferwise to name a few. As for Mark, since joining Index he has largely specialised on all things financial services and sits on the board of Plaid, Nova Credit, Intercom, Pilot and more incredible companies. Prior to Index, Mark spent 3 years in BizOps at Dropbox where the company increased tenfold during his time there.

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In Today’s Episode You Will Learn:

1.) How Mark made his way into the world of venture with Index having spent 3 years at Dropbox during a transformational time for the company? What were Mark’s biggest takeaways from seeing the growth cycle at Dropbox? How did that impact his investing mindset with Index?

2.) Why does Mark believe that venture as an asset class is commoditising? What does Mark believe the best funds will have to do to stay ahead? How does Mark build relationships of trust and authenticity so early with founders? What works? What does not? What is the right way to deliver direct and tough feedback to founders?

3.) How does Mark feel about multi-stage funds re-entering seed investing again? What are the right questions seed founders should ask multi-stage funds when determining whether to take their money? What does Mark believe it takes to be competitive and win the very best of deals? How is the Founder <> VC dynamic changing with capital supply?

4.) Why does Mark believe that most angels are going to lose their money? What does Mark wish all angels knew when they started? How does Mark feel about the rise of founders investing alongside operating? What are the pros? What are the cons? How does Mark feel about the rise of scout funds? Where is there place in the ecosystem?

5.) We are seeing unparalleled levels of activity in fintech, is this a boom or are we at the start of a fundamental shift in the landscape? Why does Mark believe we will soon see our first $100Bn neo-bank? Why does Mark believe we will see a strong rise in the consolidatory environment for fintech moving forward?

Items Mentioned In Today’s Show:

Mark’s Fave Book: Barbarian Days: A Surfing Life

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

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

20VC: Gusto Co-Founder, Tomer London on Why Most Founders Approach Fundraising With The Wrong Mindset Today, How To Construct A Values/Motivation Alignment Test To Determine The Right Investors For You & Why Delight Is So Crucial To The Success of Any Consumer Facing Product

Tomer @ Gusto

Tomer London is the Co-Founder @ Gusto, the people platform for small businesses providing one place to run payroll, manage benefits, and support your team. To date, Tomer and the team have raised over $520M with Gusto from some of the industry’s leading investors including General Catalyst, CapitalG, Kleiner Perkins, T Rowe, Fidelity and more and then individuals including Shopify Founder Tobias Luttke, Sam Altman, Max Levchin, Matt Mullenweg, Kevin Hartz and Elad Gil to name a few. Prior to Gusto, Tomer did a PHD in Electrical Engineering at Stanford and before that was Founder and CEO @ Vizmo, mobile self-service technologies for enterprise to try to fix customer care.

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In Today’s Episode You Will Learn:

1.) How Tomer made his way from creating inventory management software for his Father’s small business in Israel to Stanford and founding the unicorn that is Gusto?

2.) Why does Tomer believe that most founders approach fundraising with the wrong mindset today? What does he mean when he says, “fundraising = creating change”? What is the “values motivation alignment”? How can founders use it to help them select the right investor for them? Why should you add investors just as you would new team members?

3.) Having raised over $200M in the latest financing, how does Tomer think about when is the right time to pour fuel on the fire and go big? Is it a fundamentally different mindset when you have so much cash thrown on you? What would Tomer advise founders with suddenly expanded budgets? With 111 investors on the Gusto cap table, what would Tomer advise founders when it comes to cap table management?

4.) What have been Tomer’s biggest learnings when it comes to building a delightful product at scale across different segments? How important does Tomer feel time to delight from the UX perspective is? How does Tomer think about testing levels of user delight? NPS? Product analytics? How does Tomer think about the balance between product development and going all out for scaling?

5.) How has Tomer seen himself change and evolve as a leader of the last 5 years? What elements has he found super challenging to come to grips with? Where does Tomer believe he has a superpower on the flip side? Question from Laela @ CapitalG, what specifically did you do to create the culture that you did in the early days?

Items Mentioned In Today’s Show:

Tomer’s Fave Book: No Room for Small Dreams: Courage, Imagination and the Making of Modern Israel

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

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

Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

20VC: Vinod Khosla on What Venture Assistance Really Means, Why Many VCs Are Not Qualified To Advise Founders & Why Startups Can Innovate So Much Faster Than Incumbents

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Vinod Khosla is the Founder @ Khosla Ventures, one of the valley’s most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Vinod, he started his career as a Founder, founding Daisy Systems, a company that went on to IPO. Then in 1982, Vinod founded Sun Microsystems where he pioneered open systems and commercial RISC processors. In 1986, Vinod joined his longtime friend, John Doerr and became a General Partner @ KPCB where he helped incubate Juniper Networks and helped transform the telecommunications business with Cerent Corporation, which was acquired by Cisco Systems in 1999 for $7.2 billion.

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In Today’s Episode You Will Learn:

1.) How Vinod made his way into the world of startups with the founding of Daisy and Sun Microsystems and how that led to his entry into the world of venture with KPCB and ultimately founding Khosla Ventures?

2.) How does Vinod feel about the term “venture assistance” today? Where does Vinod believe VCs can really drive value? How does Vinod allocate his time to drive as much value for the portfolio as possible? How does Vinod get involved when it comes to talent acquisition for the portfolio?

3.) Why does Vinod believe that most board members are not qualified to advise entrepreneurs today? Why does Vinod believe that most value is driven outside of the board? What can founders to do make their boards as efficient as possible? How does Vinod advise founders to determine which advice to take vs which to disregard?

4.) How does Vinod assess his own approach and attitude to risk today? What does Vinod believe are acceptable vs unacceptable risks in startups? How does Vinod believe the very best founders think about risk management? Does Vinod agree time is the biggest killer of startups? Why does Vinod believe startups are so much quicker to innovate than incumbents?

5.) Why does Vinod believe that tolerance for failure has gone down in Silicon Valley? How does Vinod determine between the realism of when something is not work and to give up vs the visionary persistence to see a project through to the very end? What experience of his own have really led his thinking here?

Items Mentioned In Today’s Show:

Vinod’s Fave Book: Life on the Edge: The Coming of Age of Quantum BiologyThe Third Pillar

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

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

20VC: Twitch Founder & CEO Emmett Shear on When To Persist vs When To Give Up For Entrepreneurs, The Fundamental Tension When Scaling Orgs and How To Optimise Them & How The Role of CEO Fundamentally Changes with Scale

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Emmett Shear is the Co-Founder & CEO @ Twitch, the world’s leading live streaming platform for gamers and the things we love. Prior to Twitch’s exit to Amazon for a reported $970M, Emmett raised over $42M in funding from some of the best including Thrive Capital, Bessemer, Mike Maples, Aydin Senkut, Paul Graham and Y Combinator. Emmett is also a part-time Partner @ Y Combinator, advising YC companies on everything from fundraising strategy to product decisions to hiring and firing. Before Twitch, Emmett co-founded Kiko, a company he later sold on eBay for 6 figures.

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In Today’s Episode You Will Learn:

1.) How Emmett made his way into the world of startups with Kiko? How he ended up selling that for 6 figures on eBay? How that led to the creation of Justin.TV & Twitch?

2.) Why does Emmett believe starting a startup is like “deciding to take on the burden of Sisyphus?” At what point in the journey does is start to get easier? Does Emmett agree with many on the show who say, “it does not get easier, it just gets different”? How does one know when to give up vs when to persist and follow the vision?

3.) How does Emmett think about structuring an org at 1,500 people? Why does Emmett believe there is a fundamental tension when scaling teams between centralisation and decentralisation? How does one structure a reorg without causing instability? How does one communicate the reorg to the team? Where does Emmett see many go wrong here?

4.) Does Emmett agree the best CEOs are the best resource allocators? How does Emmett approach internal resource allocation today between both functions and projects? What does he find most challenging here? What does the decision-making process look like? What are his takeaways from Apple, Amazon and Microsoft in how they determine and process resource allocation internally?

5.) How does Emmett believe he has changed and evolved as a leader over the last 10 years with Twitch? What elements has he found the most challenging to master? What has he done to combat those weaknesses? Where has he always been naturally strong? What makes him so good at those particular functions?

Items Mentioned In Today’s Show:

Emmett’s Fave Book: Order without Design: How Markets Shape Cities

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

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

Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means

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Ashton Kutcher is a Founder & General Partner @ Sound Ventures. Over the last 5 years, Ashton and his partner, Guy Oseary, have built Sound into one of the West Coast’s leading new entrants with a portfolio including Lambda School, Calm, Gitlab, Affirm, Bird and many more incredible companies. As for Ashton, he started his investing career as an angel with early home runs including Spotify, Alibaba, Skype, Airbnb and Optimizely. Due to his immense success both in media and technology, Ashton has been named one of TIME magazine’s “100 Most Influential People in the World”.

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In Today’s Episode You Will Learn:

1.) How Ashton made his way into the world of startups with his foray into angel investing in Skype, Spotify etc? How did that lead to his founding Sound Ventures most recently?

2.) How does Ashton’s background in the world of media impact Sound’s investment strategy and the type of deals they get excited by? Question from Daniel Ek @ Spotify: How did your deal sourcing look lin the early days? How has that changed over time and with the institutionalisation of Sound?

3.) Why does Ashton believe people creating the future are perpetually young? What question does Ashton always like to ask founders? What does he look for in their answer? How does Ashton ensure founders feel comfortable with him? What does he do to allow them to open up? What is the hardest thing Ashton feels he has persevered through?

4.) How does Ashton build strong product intuition about products in areas he is not familiar with? In terms of great product, Ashton backed Spotify with Daniel Ek and Shak Khan, what did Ashton see in Spotify way back then? How did Shak and Daniel innovate on distribution and customer acquisition with him and Spotify?

5.) What have been Ashton’s learnings in what it takes to truly win the best and most competitive deals? Before as an angel, Ashton’s check size was friendly, now with Sound it is competitive with VCs, how does Ashton approach the element of now competing with many VCs he once co-operated with? What does Ashton make of the rise of many celebrity investors today?

Items Mentioned In Today’s Show:

Ashton’s Fave Book: The Undoing Project: A Friendship that Changed the World, Scale: The Universal Laws of Life and Death in Organisms, Cities and Companies

Ashton’s Most Recent Investment: Community

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

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

 

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