20VC: Shopify President, Harley Finkelstein on What is Being a Good Husband, What is Being a Good Father & How to Embrace Vulnerability and Authenticity in Leadership and Marriage

20VC: Shopify President, Harley Finkelstein on What is Being a Good Husband, What is Being a Good Father & How to Embrace Vulnerability and Authenticity in Leadership and Marriage

Harley Finkelstein is the President of Shopify, the platform modern commerce is built on. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify's revenue to over $4.6BN in 2021 and the team to over 10,000 employees. On the side, Harley is an Advisor to Felicis Ventures and in the past has held board seats at CBC, Omers Ventures and The C100. If that was not enough, you can see Harley on a screen near you as one of the "Dragons" on CBC's Next Gen Den.

In Today's Episode with Harley Finkelstein You Will Learn:

1.) The Founding Story:

  • What was Harley's first entrepreneurial endeavour?
  • How did seeing his family lose everything impact Harley's mindset and ambition?
  • How did Harley first meet Tobi @ Shopify? How did the Shopify journey begin?

2.) Leadership Lessons:

  • How has Harley changed as a leader over the 13 years with Shopify?
  • How does Harley embrace vulnerability and authenticity in his communication with the team?
  • What is Harley most insecure about when he looks at leadership today?
  • What have been some of the biggest lessons Harley has learned from his board on what great leadership is?

3.) The Art of Marriage:

  • What does Harley believe makes the most successful marriage?
  • Why have Harley and his wife been seeing a marriage therapist from the early days?
  • What is the biggest mistake people make when communicating with partners?
  • How has Harley changed as a husband over the years?

4.) The Joy of Fatherhood:

  • Does Harley always believe he has been a good father?
  • What was his realisation moment that he was not being the father he wanted to be?
  • What core elements of his behaviour did he change? How did that impact his relationship with his kids?
  • How does Harley ensure he performs at the highest level while also being there and being present for his family?

Item's Mentioned In Today's Episode with Harley Finkelstein

Harley's Favourite Book: The Book of Ichigo Ichie: The Art of Making the Most of Every Moment, the Japanese Way

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20 VC 077: Part 2: Kamal Ravikant: The Future Of Venture Capital

20 VC 077: Part 2: Kamal Ravikant: The Future Of Venture Capital

For your chance to win a signed copy of Venture Deals by previous guest and legend, Brad Feld all you have to do is click the Click To Tweet Link here: http://ctt.ec/Q41ZG Kamal Ravikant is an absolute hero to me after I read his incredible best selling book, Love Yourself Like Like Your Life Depends On It. As for an intro to Kamal, it goes without saying that he has worked with some of the best people in Silicon Valley and is a true tech and investing icon, but he has also trekked to one of the highest base camps in the Himalayas, meditated with Tibetan monks in the Dalai Lama's monastery, held the hands of dying patients, earned a US Army Infantry patch, walked 550 miles across Spain, been the only non-black, non-woman member of the Black Women's writers' group and written books including my favourite the previously mentioned, Love Yourself Like Your Life Depends On It. In Today's Episode You Will Learn: 1.) Where does Kamal see the future of Venture Capital? 2.) What worries Kamal about the tech scene? 3.) How does Kamal sort the wood from the trees in the frothy market of tech startups? 4.) What are Kamal's must read books and blogs? 5.) Which leaders or figures is Kamal inspired by and why? Items Mentioned In Today's Show: My Fave Book: Love Yourself Like Your Life Depends On It by Kamal Ravikant Kamal's Fave Book: The Alchemist, The Great Work of Your Life by Stephen Cope Kamal's Fave Blog: James Altucher Kamal's Most Recent Investment: Bolt As always you can follow Harry, The Twenty Minute VC and Kamal on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow Harry on Instagram here!

7 Okt 201520min

20 VC 077: PART 1: Kamal Ravikant: 'I'm Not Your Traditional VC'

20 VC 077: PART 1: Kamal Ravikant: 'I'm Not Your Traditional VC'

For your chance to win a signed copy of Venture Deals by previous guest and legend, Brad Feld all you have to do is click the Click To Tweet Link here: http://ctt.ec/Q41ZG Kamal Ravikant is an absolute hero to me after I read his incredible best selling book, Love Yourself Like Like Your Life Depends On It. As for an intro to Kamal, it goes without saying that he has worked with some of the best people in Silicon Valley and is a true tech and investing icon, but he has also trekked to one of the highest base camps in the Himalayas, meditated with Tibetan monks in the Dalai Lama's monastery, held the hands of dying patients, earned a US Army Infantry patch, walked 550 miles across Spain, been the only non-black, non-woman member of the Black Women's writers' group and written books including my favourite the previously mentioned, Love Yourself Like Your Life Depends On It. In Today's Episode You Will Learn: 1.) How did Kamal make his way into the world of Venture Capital? 2.) What were Kamal's biggest takeaways from working as an entrepreneur? 3.) What really makes a great VC? How can VCs provide true and genuine value add? 4.) Why is now the best time to be an entrepreneur? What has changed? 5.) What would Kamal advise an entrepreneur looking to build a startup? .) Where does Kamal see the future of Venture Capital? 6.) What worries Kamal about the tech scene? 7.) How does Kamal sort the wood from the trees in the frothy market of tech startups? Items Mentioned In Today's Show: Kamal's Fave Book: The Alchemist, Hemingway, The Great Work of Stephen Cope, Kamal's Fave Blog: James Altucher Kamal's Most Recent Investment: Bolt As always you can follow Harry, The Twenty Minute VC and Kamal on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow Harry on Instagram here!

5 Okt 201520min

FF 015: Y COMBINATOR WEEK: Eric Glyman, Co-Founder & CEO @ Paribus

FF 015: Y COMBINATOR WEEK: Eric Glyman, Co-Founder & CEO @ Paribus

Eric Glyman, Co-Founder and CEO @ Paribus (Y Combinator S15), the service which scans your inbox for receipts and automatically saves you money when the items you bought drop in price. Stores often guarantee that you will get the lowest prices. But they don’t follow through unless you work for it. Paribus does the work for you. In Today's Episode You Will Learn: 1.) What was Eric's career before Paribus and what was his a-ha moment was for the idea? 2.) How did Eric do things differently from the typical startup? Was this effective or would it have been more productive to go full in? 3.) What were Paribus' testing hypotheses like? Does Eric prefer mass market testing or niche 100 person testing? 4.) How was the admissions process for YC, why did Eric choose YC and why were YC attracted to Paribus? 5.) What would Eric advise founders looking to get into YC? Is there anything they can do or know that will increase their chances of getting into YC? 6.) What were the breakthrough moments for Paribus? What were the most challenging elements and how did Eric overcome them? Items Mentioned In Today's Show: Eric's Fave Book: I, Robot Eric's Fave Blog: AppSumo by Noah Kagan As always you can follow Harry, The Twenty Minute VC, Eric and Paribus on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, follow Harry on Instagram here!

2 Okt 201525min

20 VC 076: Y COMBINATOR WEEK: Aaron Harris, Partner @ YC

20 VC 076: Y COMBINATOR WEEK: Aaron Harris, Partner @ YC

Aaron Harris is a Partner at Y Combinator and also newly one of my favourite podcast hosts with his brilliant show, Startup School Radio, for all startup lovers it is a must listen. Prior to YC, Aaron was cofounder of Sequoia backed Tutorspree, which was funded by Y Combinator in 2011. Before Tutorspree he worked at Bridgewater Associates, where he managed product and operations for an analytics group. He also writes an awesome blog which can be found here! In Today's Episode You Will Learn: 1.) How did Aaron make his move into the world of entrepreneurship with Tutorspree and then become a YC Partner? 2.) Why did Aaron join YC and why does he believe the biggest potential lies at this stage of the cycle? 3.) Now at YC, Aaron is a Partner, what does that entail, what level of interaction do you have with the founders, where does YC look to add serious value? 4.) With the mass of startups now in the 100s coming out of each YC demo day, how does YC assure the same quality and level of value add? 5.) With regards to testing what is YC’s opinion? How does YC assess whether a product does have product market fit? What are the YC requirements for growth whilst in YC? 6.) What happens after the YC experience, does YC maintain conversations and communication? How does YC try to maintain valuations at a reasonable level to stop YC price inflation? 7.) What is the future for YC? Are we going to see another funding round? Is the YC model scalable? Could we have a YC Europe? Items Mentioned In Today's Episode: Aaron & YC's Podcast: Startup School Radio Aaron's Fave Book: The Diving Bell and The Butterfly, Founder's At Work by Jessica Livingston As always you can follow Harry, Aaron, The Twenty Minute VC and YC on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

30 Sep 201524min

20 VC 075: Y COMBINATOR WEEK: Kirsty Nathoo, CFO @ Y Combinator

20 VC 075: Y COMBINATOR WEEK: Kirsty Nathoo, CFO @ Y Combinator

Kirsty Nathoo is the CFO of Y Combinator. As CFO, she holds the keys to the kingdom – literally. Not only does she control and manage Y Combinator’s internal finances, from paying bills to helping organize demo days to actually making sure Y Combinator’s money is wired to startups from the proper accounts; but she helps YC startups coordinate outside financings, tax issues, incorporation and other fiscal matters. She’s the financial brains behind the entire operation, with YC partner Harj Taggar stating that ‘YC would cease to operate if Kirsty was not around’. In Today's Episode You Will Learn: 1.) How Kirsty made her move from PWC in Cambridge to CFO at the World’s Most Successful Accelerator? 2.) Joining YC permanently in 2010, how has Kirsty seen it develop to today’s current state? What has been the key drivers to the success and growth of YC? 3.) As CFO Kirsty has developed a certain pattern recognition with regards to what investors and VCs like to see in the terms of startups. What are they? 4.) Kirsty has seen the progression of many startups, what are the most common problems startups face in the fundraising cycle? What are the commonalities in those that are successful? 5.) How does YC address the issue of potentially inflated valuations for their alum? 6.) What are some financials that all founders should know all the time? 7.) What is the future for YC? Are we going to see another funding round? Is the YC model scalable? Could we have a YC Europe? As always you can follow Harry, The Twenty Minute VC and Y Combinator on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

28 Sep 201527min

FF 014: Making Great Founders, Idea Creation and The First 100 Days Of A Startup with Alice Bentinck, Co-Founder @ Entrepreneur First

FF 014: Making Great Founders, Idea Creation and The First 100 Days Of A Startup with Alice Bentinck, Co-Founder @ Entrepreneur First

Alice Bentinck is Co-Founder at Entrepreneurs First, the accelerator program that puts founders first! Previously, Alice worked at prestigious consultancy firm McKinsey & Co, before turning down an offer from Google to found Entrepreneur First alongside Matt. She taught herself to code, and founded Code First Girls in 2013 to help more women get into tech. She sits on the board of Sherry Coutu's Founders4Schools, is on Imperial College London's Department of Computing Industrial Liaison Board, and acted as the Prime Minister's expert on startups at the Northern Future Forum. She has been recognised in Management Today’s 35 under 35 and the Evening Standard’s Top 1000 most influential Londoners. In Today's Episode You Will Learn: 1.) How Alice came up with the idea for EF and why she decided to found the company? 2.) What would Alice recommend is the best way to build a company from scratch? EF is for technical individuals, what can non technical individuals do? 3.) What would Alice say makes a great founder? Has she seen any commonalities in the great founders that have exited EF? 4.) What is Alice's opinion on equity divisions within startups? What is the right way to approach the topic? 5.) What should teams focus on in the first 100 days of their startup? What is the 20% that produces 80% of the results? 6.) What has been the hardest aspect of growing the business and how did Alice overcome it? As always you can follow Harry, The Twenty Minute VC and Alice on Twitter here! If you would like to see a more colourful side to Harry and many a mojito session, you can follow him on Instagram here!

25 Sep 201520min

20 VC 074: The Future of Healthcare with Bob Kocher, Partner @ Venrock

20 VC 074: The Future of Healthcare with Bob Kocher, Partner @ Venrock

Bob Kocher is a Partner at Venrock and focuses on healthcare IT and services investments. He currently serves on the Boards of Aledade and Jiff, and is a Board Observer at Grand Rounds and Doctor on Demand. Prior to Venrock, Bob served in the Obama Administration as Special Assistant to the President for Healthcare and Economic Policy on the National Economic Council. In the Obama Administration, Bob was one of the shapers of the Affordable Care Act. Before the White House, Bob was a Partner at McKinsey & Company where he led McKinsey Global Institute’s healthcare economics work and Center for United States Health System Reform. In Today's Episode You Will Learn: 1.) How Bob made his way from The White House to Venrock as a VC? 2.) How did working at The White House prepare Bob for his career as a VC, where does Bob have the biggest opportunity to change the healthcare system? 3.) What are the barriers to entry that a preventing full scale innovation and business growth in the healthcare IT space? 4.) Why have we seen a large increase in healthcare startups? What more would you Bob like to see in the healthcare space, either from the side of the startups or VC’s? 5.) How does Bob perceive the integration of software and healthcare in the future? 6.) As a healthcare professional, what would Bob recommend an individual with a high powered, demanding job in order to lead a healthy lifestyle? Items Mentioned In Todays Episode: Bob's Fave Book: The System Bob's Most Recent Investment: Lyra Health As always you can follow Harry, The Twenty Minute VC and Bob on Twitter here! If you would like to see a more colourful side to Harry with many a mojito night, you can follow him on Instagram here!

23 Sep 201519min

20 VC 073: Life Inside Accel Partners with Michael Treskow @ Accel

20 VC 073: Life Inside Accel Partners with Michael Treskow @ Accel

Michael Treskow is a VC @ Accel Partners, one of the world's most successful venture firms having funded the likes of Facebook, Dropbox, Spotify, Etsy and many more. At Accel, Michael is responsible for the firm’s investments in SpaceApe, a mobile games developer, and GoCardless, an online direct debt provider. Michael was also instrumental in Accel's investments and ongoing work with Funding Circle, Packlink, Qubit, Semmle, Trufa and WorldRemit. Prior to Accel, Michael focused on early-stage investments in technology companies at Warburg Pincus in San Francisco, invested in publicly traded technology companies at Highside Capital, and helped advise technology companies as part of Morgan Stanley's investment banking team in New York. In Today's Episode You Will Learn: 1.) How Michael made his way into the VC industry? Do you think it is very important for VCs to have entrepreneurial experience? 2.) How does Michael compare the investing environments between London and SF? What was his biggest takeaway from Warburg Pincus in SF? 3.) Accel is stage agnostic, why is that? What size market attracts Michael? How can Michael tell whether founders have the ability to exploit the market? 4.) What Michael believes are his key value adds? Have these changed over time? 5.) We often hear startups being described as ‘uber for’, ‘tinder for’. Do VCs like this simplification of business? How else would Michael suggest a complex concept can be broken down into something easily digestible? 6.) Does Michael still believe there is room for improvement in the consumerisation of enterprise software? Does Emergence Capital's pivot signal a turning tide? Items Mentioned In Todays Episode: Michael's Fave Book: The Innovator's Dilemma, Crossing The Chasm Michael Productivity Tools: Wunderlist Michael's Fave Blog or Newsletter: Dan Primack, Term Sheet Michael' Most Recent Investment: CartoDB As always you can follow Harry, The Twenty Minute VC and Michael on Twitter here! If you would like to see a more colourful side to Harry with many a mojito night, you can follow him on Instagram here!

21 Sep 201523min

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