Jesse Middleton is a General Partner @ Flybridge Capital Partners. Prior to joining Flybridge, Jesse was an early executive at WeWork, one of the fastest growing and most valuable startups in history. He co-founded WeWork Labs in 2011, and ran WeWork X, M&A, startup investments, business and digital product development as well as inside sales during his five-year tenure at the company. Prior to WeWork, Jesse was the co-founder and CEO of Backstory, a venture backed startup. Jesse also has experience as a prolific angel investor having invested in the like of Fitmob (acq by ClassPass) YourTrove acq by LiveNation and inDinero, who you might remember we had Jessica Mah, Founder @ inDinero on the show.

In Today’s Episode You Will Learn:

1.) How Jesse made the transition from operator with WeWork to General Partner @ Flybridge?

2.) At what stage does founder vision transition to become stubbornness? How does Jesse approach the situation of telling a founder when it is not working?

3.) How does Jesse's investment mindset shift from making the move from angel to VC with fiduciary responsibility?

4.) How does Jesse look to develop pattern recognition as a new entrant to VC? How important a role does mentorship play for Jesse?

5.) What are the characteristics Jesse looks for in a founder that suggest an innate problem solver? How does Jesse deal with problems when the 'shit hits the fan?'

Items Mentioned In Today’s Show:

Jesse’s Fave Blog and Newsletter: Purple, The Skimm

Jesse’s Fave Book: Leadership & The Challenge of Self Deception

Jesse’s Most Recent Investment: Squire

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Peter Pham is a Co-Founder at Science, the startup studio that helps incubate companies co-building them alongside CEO's, with recent companies like Dollar Shave Club (acquired by Unilever for $1B) and leading marketplace, DogVacay. More recently Science created created one of the top 100 iOS Apps called Wishbone. Peter has also helped his portfolio raise over $350M in that time. Previously as an operator, he led Photobucket to its $300M acquisition by Fox Interactive Media as well as CEO of BillShrink (acquired by MasterCard.)

In Today’s Episode You Will Learn:

1.) How Peter made the transition from operator to company builder with Science?

2.) How does Peter approach the fundraising process itself? How does he instruct founders about the right ways to approach and enter the fundraising game?

3.) How can entrepreneurs determine whether a VC is saying not to them? What are the signs that an investor is genuinely interested?

4.) With 3,000 no's from investors, how does that affect Peter's mentality? How does he avoid the negativity surrounding a VC saying no?

5.) What are Peter's major learnings on how companies scale effectively today? How important are network effects to this scaling?

Items Mentioned In Today’s Show:

Peter’s Fave Blog and Newsletter: Recode

Peter’s Fave Book: How To Win Friends & Influence People

Peter's Most Recent Investment: Handstand App

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

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

Sean Brecker is the CEO @ Headspace where he is the driving force behind all financial and commercial matters including overseeing the company's growth of it's product line which now has over 8m downloads. Sean was also instrumental in attaining the first  institutional round of financing which included investment from the likes of LinkedIn's Jeff Weiner, Jim Breyer, Jessica Alba and Jared Leto, just to name a few. Prior to Headspace, Sean spent 15 years in banking with the likes of JP Morgan, Lehmann Brothers and Citigroup.

In Today’s Episode You Will Learn:

1.) How Sean made the move from banking to CEO of meditation service, Headspace?

2.) Meditation can be viewed with some hippy stereotypes, how does Sean look to optimise the onboarding for new users and incorporate elements of education?

3.) How does Sean implement a strategy of habit forming within the users? In the words of Nir Eyal, how do we get them ‘hooked’? How long on average does it take for an action to be completed before it becomes a habit?

4.) How does Sean try and optimise the transition from free to paid user with Headspace? How does Sean try and remove as much friction as possible in the process?

5.) How has Sean seen the growth of the health and wellness space over the last few years? We obviously have the likes of Calm, is this market a winner takes all and how does Sean approach market competition at Headspace?

6.) How was the fundraising process for Sean? How did he come to meet investors like Jeff Weiner, Jim Breyer, Jessica Alba and Jared Leto?

Items Mentioned In Today’s Show:

Sean’s Fave Blog and Newsletter: The Information, Recode

Sean’s Fave Book: The Hard Thing About Hard Things, A Man In Full

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Chad Byers is a General Partner @ Susa Ventures and very exciting news, Susa last week announced the raise of Susa II, a new $50m fund, testament to the quality of fund 1 which included the likes of former guests Lyst, RobinHood, LendUp and many more incredible companies. As for Chad, he focuses on investments in enterprise software, fintech, and healthcare. Prior to Susa, Chad spent time in various marketing and product management roles. As well as being a prolific angel investor in over 30+ companies.

In Today’s Episode You Will Learn:

1.) How Chad made the transition from angel investor to General Partner @ Susa?

2.) How was the fundraise with Susa 1? How was the fundraise for Susa II? How did the funding rounds change for each fund?

3.) How does Chad assess LP fit? Is all LP money not equal? What does Chad look for in his LPs?

4.) Question from Michael Kim @ Cendana: How does Chad look to establish the mindshare with entrepreneurs and other VCs for Susa in today's competitive environment?

5.) How does Chad approach the reserve structure of Susa fund II? How did Chad come tot hat conclusion as the optimal amount for follow on?

Items Mentioned In Today’s Show:

Chad’s Fave Blog and Newsletter: Coding VC, Bill Gurley: Above The Crowd

Chad’s Fave Book: When Breathe Becomes Air

Chad's Most Recent Investment: Modsy

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

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

Greg Bettinelli is a Partner at Upfront Ventures where he specialises in businesses at the juncture of retail and technology. Prior to Upfront, Greg was the CMO for HauteLook, a leading online flash-sale retailer that was acquired by Nordstrom for $270mm. Before HauteLook, Greg was Executive Vice President of Business Development and Strategy at Live Nation, responsible for strategic direction and key business partnerships for Live Nation’s ticketing and digital businesses. Before Live Nation, Greg held a number of leadership positions at eBay and StubHub and was the business leader who led eBay’s acquisition of StubHub in 2007.

In Today’s Episode You Will Learn:

1.) How Greg made his way into VC from the unconventional world of retail and consumer?

2.) How has Greg's unconventional background altered how he views investments and founders? How does Greg test for the 'grit' required to be a founder?

3.) With the rise of direct to consumer, will we see the end of the physical retail store? Why do big retailers still have such little e-commerce presence?

4.) To what extent does Greg view brand as a form of IP in a prospective investment? How have we seen changing brand loyalty in the last decade?

5.) What are the fundamentals for growing a consumer brand successfully? Who has exemplified this?

Items Mentioned In Today’s Show:

Greg’s Fave Blog and Newsletter: Dan Primack: Term Sheet

Greg’s Fave Book: Michael Lewis

Greg's Most Recent Investment: Happy Returns

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Paul Berberian is the CEO of Orbotix, the company that created Sphero, the robotic ball controlled from your smartphone. They have investment from our friends in Boulder, Brad Feld and David Cohen. Prior to Sphero, Paul was the co-founder of Raindance Communications (NASDAQ: RNDC). Paul also founded Market Force Information, an emerging information company with a vision to provide retailers. As well as, LINK-VTC, a video teleconferencing company, which was sold in 1995 to Frontier Communications. 

In Today’s Episode with Paul You Will Learn:

1.) How Paul came to be CEO @ Sphero?

2.) Paul has founded and run 7 businesses, How has Paul seen his style of leadership change over the past decade or so?

3.) Question from Brad Feld: When Paul disagrees with his board, how does he resolve it? What have been Paul's learnings in maintaining a happy board environment?

4.) Sphero have raised, at last count, $80m? How has Paul seen investor sentiment to hardware alter over the 5-6 years? How did he meet his investors? What did Paul do well and what would Paul like to improve upon for next time?

5.) Question from Brad Feld: ‘Sphero looks like a massive success but every startup has had failures, so what have Paul's failures been and what did he learn from them?

Items Mentioned In Today’s Show:

Paul’s Fave Blog and Newsletter: Quora

Paul’s Fave Book: The Black Box

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Ben Einstein is Founder and General Partner @ Bolt, Bolt is a fund designed to address the unique needs of early-stage startups at the intersection of hardware and software, investing up to $500K in pre-seed, pre-product companies. They have created and backed some world class businesses that have received later funding from Khosla, Kleiner Perkins, NEA, and Softtech just to name a few.

In Today’s Episode with Ben You Will Learn:

• How Ben made his way into VC from such a product centric background?
• Why have we seen a rise in hardware investing over the last 5 years? How has this affected the hardware ecosystem?
• To what extent do hardware and software integrate today? Why have we seen the rise of software determining the hardware winners?
• Why is brand the most important thing in consumer hardware? Who has done it best? Who has not done it well?
• What is Ben’s biggest advice to hardware founders today? Why is raising too much money extremely dangerous for hardware founders?

Items Mentioned In Today’s Show:

Ben’s Fave Blog and Newsletter: Ben Evans

Ben’s Fave Book: The Box

Ben’s Most Recent Investment: Grow: Redesigning Gardening

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Dave McClure is the founding partner of 500 Startups, who have made over 1500 investments in the likes of Twilio, SendGrid, Intercom and Makerbot just to name a few. Prior to 500 Dave was on the investment team at Founders Fund, he also led the Facebook Fund Incubator and was Head of Marketing @ Paypal pre IPO.

In Today’s Episode with Dave You Will Learn:

• How Dave made his way into VC and came to found 500 Startups?
• Do you need unicorn exits to have significant venture returns? What is the 500 view with regards to the hit ratio of finding unicorns?
• How much ownership does 500 typically take? Does this allow Dave enough of a right to follow on in further rounds with such a small initial slice?
• How does Dave and 500 avoid the inherent signalling risk involved with their fund and accelerator? How prominent is signalling in today’s market?
• What did Dave think of Sam Altman’s statement on YC not accepting companies from other accelerators? How does Dave view YC companies?

Items Mentioned In Today’s Show:

Dave’s Fave Blog and Newsletter: Brad Feld, AVC, Mark Suster

Dave’s Fave Book: Guns Germs and Steel, The Mystery of Capital

Dave’s Most Recent Investment: Markhor

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

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

Eve make 1 perfect mattress - made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up - it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Adam Nash is the President and CEO of Wealthfront, where he is on a mission to put the client first and change the bad practices of the financial services industry. Adam joined Wealthfront from Greylock Partners, where he was an Executive-in-Residence. Prior to Greylock, he was VP of Product Management at LinkedIn, where he built the teams responsible for core product, user experience, platform and mobile. Adam also held a number of roles at Ebay, Atlas Venture Preview Systems and Apple.

4.) How was the transition for Andy in making the move from PM to COO to CEO? What were the biggest challenges and surprises?

5.) Why does Andy believe that building software through hierarchy does not work? How can leaders empower their team with a sense of ownership?

6.) Why do humans suck at investing? Will we see the domination of full scale financial robo advisors in the next 10 years?

David Pakman is a Partner at Venrock and the man behind Venrock’s leading of the Series A and B rounds for Dollar Shave Club. Prior to Venrock David spent 12 years as an internet entrepreneur. Including being CEO of eMusic, the world’s leading digital retailer of independent music, second only to iTunes. Prior to eMusic, David co-founded Myplay in 1999, which he later sold, in 2001, to Bertelsmann’s ecommerce Group. If that wasn’t enough David is also the co-creator of Apple Computer’s Music Group.

In Today’s Episode You Will Learn: 

• How did David make his way into the world of VC with Venrock?

• David invested in Dollar Shave when subscription ecommerce funding was largely out of favour. What was it that excited Dave about Dollar Shave and why did he choose to invest?

• To what extent do we see the existence of party rounds in today’s funding environment?

• Venrock took the rather unusual position to lead both the A and B rounds for Dollar Shave. What was the internal conversations like within Venrock towards this decision?

• Dollar Shave was growing at phenomenal rates with impressive growth, what was behind the decision to sell at this time? What were the incentives behind selling to Unilever?

• Will we see other large e-commerce exits in the future? What does the future M&A environment look like for consumer businesses?

Items Mentioned In Today’s Show:

Matt’s Fave Book: Mindset by Carole Dweck

Matt’s Most Recent Investment: Pearl

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Matt Ocko is the Co-Managing Partner and Co-Founder @ Data Collective and has over 3 decades of experience as a tech entrepreneur and VC and has made investments in the likes of Facebook, Zynga, Uber and AngelList just to name a few. If that was not enough he is also an inventor on over 40 granted or in process patents. A truly deep thinker and one of my fave ever shows to record.

In Today’s Episode with Matt You Will Learn:

• How Matt made his way into VC and came to co-found Data Collective?
• Why does Matt believe “All Fund Size Models are Wrong”. Does the current bifurcation of VC into angels/micro-VCs, small seed/A funds, big bruisers, and post-C/pre-IPO make for sub-optimal returns both on a societal and monetary perspective?
• What does the opportunity fund allow Data Collective? How do they use the initial fund to invest for insight in into companies at the earliest stages? How do they avoid the negative signalling risk that is normally ensued with an opportunity fund?
• How important is thesis driven venture firms? Does specialisation aid or hinder venture returns and why?
• How does Matt view the lifecycle of current venture? Matt has previously said it is inherently inefficient, why?

Items Mentioned In Today’s Show:

Matt’s Fave Blog and Newsletter: MIT Technology Review

Matt’s Fave Book: The Way Things Work

Matt’s Most Recent Investment: Tradeshift

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

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

Eve make 1 perfect mattress - made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up - it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Dhananja Jayalath is the Co-Founder & CEO @ Athos, creating the new standard for fitness by changing the way we train the human body. Athos have funding from our friends at Social Capital, Felix Capital and DCM Ventures just to name a few of their investors. Prior to Athos, DJ turned down a job with Apple straight from University to pursue his vision of creating the next generation of consumer fitness wearables with Athos.

In Today’s Episode with DJ You Will Learn:

• How DJ went from University to turning down Apple to founding Athos?
• How did DJ come to meet Chamath @ Social? How was the fundraising experience? What did Athos do well and what would DJ like to improve for the next round?
• How does DJ approach iteration and testing within product testing at Athos?
• What are the lessons DJ has learned in the manufacturing and iteration process with Athos?
• How does DJ approach business models for Athos today? Does DJ agree that the winners of hardware will be determined by software?

Items Mentioned In Today’s Show:

DJ’s Fave Book: Velocity: The 7 New Laws For A World Gone Digital

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

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

Steve Schlafman is an early stage investor @ RRE Ventures, where he specialises on marketplaces, mobile services, and hardware. Steve is responsible for RRE’s investments in theSkimm, Hightower, TinyBop, Breather, and Managed by Q. Prior to joining RRE as a Principal, Steve was a Principal and rockstar seed investor at Lerer Ventures. Before becoming a venture capitalist, Steve worked at Stickybits Inc. and Turntable.fm, and served as Director of Venture Investments at The Kraft Group. Steve also worked at Massive Inc. and at Microsoft, where he focused on Biz Dev Strategy and Corporate Finance.   

In Today’s Episode with Steve You Will Learn:

• How Steve made his way into VC from Microsoft, to Kraft to startup to VC?
• Why does Steve think Seed to Series A is such a different ball game? What are the different characteristics encompassed within each?
• With such little data at seed, what does Steve’s DD process look like? How does that affect his investment decision making process @ RRE?
• What is the valuation comparison between Seed and Series A? How is this determined and how has this changed since Steve’s time at Lerer?
• Why do the best markets often appear small and become meaningful? How does Steve look to detect these small markets?

Items Mentioned In Today’s Show:

Steve’s Fave Book: Who (Hiring Process), Work (Hiring @ Google), Leading (Michael Moritz)

Steve’s Fave Blog or Newsletter: AVC, Stratechery, The Skimm

Steve’s Most Recent Investment: Brightwheel

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

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

Justin Kan is a Partner @ world renowned, Y Combinator. The birthplace of the likes of Airbnb, Reddit, Dropbox, Stripe, Zenefits and many more incredible companies. Prior to YC, Justin co-founded SocialCam, acquired by Autodesk for $60m and Twitch.tv, the world's leading video platform and community for gamers, acquired by Amazon for $970m in 2014.  

In Today’s Episode with Justin You Will Learn:

• How Justin came to found Twitch.tv and then later made the transition into VC with YC?
• Having been a YC alum, how has Justin seen YC as an institution change over time? How have the interviews, demo days, mentoring arrangements altered? How can YC keep the same quality of startup treatment with the mass scaling taking place?
• YC always positions itself as an accompaniment to the VC industry, does the new $700m YC growth fund not directly compete against VCs?
• What 3 qualities does Justin believes all good investors must have? How has Justin looked to establish his own personal brand? What has worked and what has not?
• Justin is very bullish on Snapchat, why so? What makes Justin so excited for the platform? How does Justin use it to such success? What would Justin like to see change in the platform?

Items Mentioned In Today’s Show:

Justin’s Fave Book: Shogun

Justin’s Fave Blog or Newsletter: Nuzzel & The Information

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

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