20VC: OpenAI's $6BN Jony Ive Deal | YC Is Both Chanel and Walmart—and Has Officially Won | Builder.ai Implodes and Hinge IPOs: Who Wins & Who Loses | Seed Is Easy. Series A Is Brutal & The Dirty Truth About Late-Stage Venture

Fritz Lanman is the CEO @ ClassPass, the startup that provides the most flexible fitness membership ever. To date, they have raised over $154m in VC funding from the likes of Thrive, GV, CRV, Fifth Wall and Temasek just to name a few. As for Fritz, prior to ClassPass he was the Founder & CEO @ Livestar, a mobile recommendations startup that was acquired by Pinterest. Before that, he was a Senior Director in the Corporate Strategy Group @ Microsoft where he led several multi-billion dollar M&A evaluations and strategy projects including the Facebook investment and Yahoo deal. If that was not enough, Fritz is also a tremendously successful angel with a portfolio including the likes of Square, Pinterest, Wish, Flexport, Everlane and 75 or so more companies. In Today's Episode You Will Learn: 1.) How Fritz made his way into the world of startups with Microsoft? How that led to angel investments in Wish, Flexport, Square and more? How he came to be CEO @ ClassPass? 2.) How did the $250m Microsoft investment in Facebook come about? What made Fritz so confident he told Steve Ballmer he was willing to bet his career it would be a $10Bn company? What was the decision-making process internally around that deal? 3.) How does Fritz assess his own asset allocation strategy? Why does Fritz not agree with thesis-driven angel investing? When starting angel investing, how did he approach portfolio construction? Why does Fritz believe it is immensely synergistic to be both an operator and angel? As a result, how does Fritz approach placing investors in a quadrant between helpfulness and high maintenance? 4.) Why does Fritz believe that your investor cannot be your recruiter? What have been Fritz biggest learnings on continuously attracting the best talent? Why does Fritz believe that it is BS that one should not celebrate fundraising? Ultimately, what does Fritz elieve fundraising signifies? 5.) ClassPass has expanded to 34 markets over the last few years, how does Fritz determine when is the right time to pour fuel on the fire? What are the 2 fundamental questions one must ask before you do? Does Fritz believe that aggressive growth and capital efficiency are mutually exclusive? How does Fritz think about capital efficiency with ClassPass today? Items Mentioned In Today's Show: Fritz's Fave Book: Endurance: Shackleton's Incredible Voyage to the Antarctic As always you can follow Harry, The Twenty Minute VC and Fritz on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

20 Juli 201835min

Elad Gil is the Founder @ Color, the startup that shows you your genes can help you make better health decisions. They have raised over $112m in funding from the likes of General Catalyst, CRV, 8VC, Aaron Levie and more incredible names. Elad is also an incredible angel, counting the likes of Airbnb, Stripe, Optimizely, Opendoor and Wish all in his portfolio. Now Elad is adding a new string to his very talented bow with the release of his book, High Growth Handbook, published by Stripe in which Elad interviews 14 leaders from the valley from Marc Andreesen to Reid Hoffman to Patrick Collison. Plus shares his own experiences from Google, growing from 1,500 to 15,000 and Twitter, growing from 100 to 1,500. Not only is this the first book I have read voraciously from cover to cover in a long time but it is now outselling Zero To One and Lean Startup as pre-order. In Today's Episode You Will Learn: 1.) How Elad made his way into the world of startups, came to found 2 companies that sold to Twitter and Google and came to invest in Airbnb, Stripe, Wish etc? 2.) How does Elad define the role of the CEO today? What are the commonalities in those truly great CEOs? How do the very best CEOs hire the very best execs? How do they address role allocation internally? How do they determine between employees that do and do not scale with the firm? Where do CEOs make the most fatal mistakes in high growth startups? 3.) Why are pre-emptive rounds so common today? Why does Elad believe many people will lose a lot of money in them? What advice does Elad give to founders when they are an option? Does Elad believe the lack of liquidity is good for venture this cycle? How does Elad assess the emergence of megafunds? How does this alter and distort the market? 4.) With regards to market share, how should founders prioritise between pricing and market share? Is cash ever a defensible moat? What does Elad mean when he says that "too many people are stuck on Amazon as the winning model"? Why does Elad believe that margins and capital leverage are the unsung heroes of tech? 5.) Why does Elad believe we have seen such a reduction in M&A? Why do many founders not fully assess the financial benefits of being bought by a high growth startup? What are the big questions founders should ask when an M&A opportunity does arise? What does Elad believe are the reasons to avoid IPOing? What are the inherent benefits of going public? Items Mentioned In Today's Show: Elad's Fave Book: Ben Horowitz, Andy Grove As always you can follow Harry, The Twenty Minute VC and Elad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

17 Juli 201847min

Rachel Blumenthal is the Founder & CEO @ Rockets of Awesome, the startup that is reinventing the way parents shop for their kids clothes. To date, Rachel has raised over $19m in VC funding from the likes of Kirsten Green @ Forerunner, August Capital, General Catalyst, Gwyneth Paltrow and Female Founders Fund to name a few. Prior to Rockets of Awesome, Rachel founded fashion jewelry brand, Rachel Leigh. Rachel scaled the business to being available in over 300 stores worldwide and being named one of Oprah's "Favourite Things". Before that Rachel began her career in the publicity department at Yves Saint Lauren. In Today's Episode You Will Learn: 1.) How Rachel went from founding a company that created one of Oprah's "favourite things" to reinventing the way parents shop for their children today? 2.) Why does Rachel believe that "fundraising is like dating"? What does Rachel mean when she says "you have to play the game"? What does this literally look like in practice? What works in generating investor interest? What does not? Where does Rachel see many make mistakes in the fundraising process? 3.) How does Rachel think about capital efficiency with the evolution of her business? What tips and suggestions does Rachel give to increasing burn flexibility when future growth is ambiguous? Why does Rachel disagree with the thesis of raise money when you don't need it? What length of time does Rachel believe is the right time to raise for? 4.) Rachel has said before that, "the best investors are operators". What makes Rachel believe this? What are the drawbacks to operator VCs? What are the benefits to non-operator investors? What makes the truly special investor? How can a founder stress test this prior to their investment? What advice would Rachel give to a non-operator VC to improve their empathy and experience with founders? 5.) Rachel previous sly said to me that "being a woman in this male-dominated environment is everything the stereotype suggests", what moment or story particularly resonates for Rachel when saying this? How did she respond? How can less confident first time minority founders respond in these situations? Items Mentioned In Today's Show: Rachel's Fave Book: Fast Company, Inc As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

13 Juli 201835min

Pete Flint is a Managing Partner @ NFX, one of Silicon Valley's newest and most exciting funds with the recent announcement of their new $150m fund late last year. Prior to VC, Pete was a serial entrepreneur building one of today's most successful marketplaces, as the co-founder of Trulia. Pete led the company from inception to more than 50 million monthly unique users, $250m in VC funding from the likes of Sequoia and Accel culminating in their merger with Zillow in 2015 that valued Trulia at $3.5 billion. Before Trulia, Pete was part of the founding team of lastminute.com, a leading European online travel site that was acquired in 2005 for over $1 billion. In Today's Episode You Will Learn: 1.) How Pete made his way into the world of startups joining the founding team of lastminute.com and how that led to the founding of Trulia and entry into VC? 2.) Why does Pete believe that startup timing is so crucial? How does Pete analyze market timing risk when investing? What is the right way for investors to think about the innovation cycle we are in today? On review, what does Pete believe lastminute.com did most right? What would he most want to change? 3.) What are the leading indicators that suggest potential in a network effect business? Would Pete agree with Josh @ Jackson Square that not all GMV is created equal? How does Pete anlyse the lack of free and open distribution today and how that affects marketplace scaling? Why does Pete still believe marketplaces are some of the most capital efficient businesses to grow? 4.) What has been Pete's greatest time of failure in his career? What is the framework Pete uses to analyse and assess his own ego? What are the commonalities in how Pete has seen truly great founders overcome failure? How does Pete balance between realism when something is not working and the mission and vision of the founder? 5.) How does Pete think about optimising decision-making, both in investing and operating? How does Pete approach the balance of head vs heart? When is the right time to decide with your head? When is the right time to decide with your heart? Why does Pete argue early stage investing must be decided with your heart? Items Mentioned In Today's Show: Pete's Fave Book: Leonardo Da Vinci Pete's Most Recent Investment: Ribbon As always you can follow Harry, The Twenty Minute VC and Pete on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Whether you're starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that's so ridiculously easy to use and you'll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who's got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the "how did you hear about us section". Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

9 Juli 201836min

Joe Fernandez is the Founder & CEO @ JoyMode, the startup that allows you to lend everything you need to have the experiences you want. To date, Joe has raised over $16m in funding for Joymode from friends of the show including Homebrew, Slow Ventures, Founder Collective, Scott Belsky, Collaborative Fund and Lowercase, just to name a few. As for Joe, prior to founding JoyMode, Joe founded Klout, one of the leading social media analytics platforms of the day and raised $40m in funding from Kleiner Perkins, IVP, Venrock, Greycroft and more. Klout was ultimately acquired by Lithium Technologies where Joe sits on the board. In Today's Episode You Will Learn: 1.) How Joe made his way into the world of startups with the founding of Klout? Given his entrepreneurial start, would Joe say he is unemployable? 2.) Question from Craig Shapiro: What was your single greatest lesson from the Klout journey? How has that impacted how you operate JoyMode today? How has Joe approached fundraising fundamentally differently today than with Klout? How is Joe's team building strategy today different to his with Klout? 3.) Why does Joe believe that "serial entrepreneurs are over-rated"? What does Joe mean when he says, "you have to know which hill you are willing to die on"? How does Joe look to accurately ego check today? What innovative methods does Joe employ internally to ensure that his views are validated and not submitted to? 4.) What does Joe mean when he says, "you have to make big bets to win"? How can you implement this risk-taking mentality in larger teams? What is the right way for both the team and investor base to respond? How does Joe use continuous iteration and data-centricity to test and validate these theses? 5.) How does Joe approach investor update emails? Why does Joe look to terrify investors with each update? Does Joe believe that it is right to thanks specific individuals in those emails? Does like like to select individuals and request their help in the emails? How can past updates be used to attain future investors? Items Mentioned In Today's Show: Joe's Fave Book: The Accidental Superpower As always you can follow Harry, The Twenty Minute VC and Joe on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

6 Juli 201831min

Joel Monegro is Founding Partner @ Placeholder.VC, one of the new venture capital partnerships that invest solely in crypto assets and more specifically in decentralized information networks. Prior to founding Placeholder, Joel spent three years at Union Square Ventures developing the firm's blockchain investment thesis and portfolio. Before USV, Joel started the Digital Economy Department at the Ministry of Industry and Commerce of the Dominican Republic, a government office in charge of developing the country's national and technology agenda. In Today's Episode You Will Learn: 1.) How Joel made his way into the world of VC with USV and what created his love of crypto and led to his leaving USV to found Placeholder? What were some of Joel's biggest investing lessons from his time with USV? 2.) How does Joel approach portfolio construction in building out a crypto portfolio? How does the use of reserves and building positions change when comparing VC to crypto? Why does Joel believe that the most interesting place to invest in crypto is in the assets themselves, rather than the companies? 3.) When does Joel think we will see institutional capital begin to move into the space in a meaningful way? What needs to happen/change for this institutional interest to materialize? How is the element of "custody" crucial to the entrance of institutions? 4.) In terms of fund construction, liquidity is often an attractive element to crypto, why does Joel believe that a traditional venture fund structure is necessary for Placeholder? What are the benefits both to the fund and the projects it backs? How do LPs both traditional and non-traditional respond to this? 5.) Joel has said before the 2 core elements are crypto economics and governance, why does Josh believe this? Why is governance the foundational layer where value will accrue in the space? How does the lack of defensibility of crypto projects make governance ever more valuable? Items Mentioned In Today's Show: Joel's Fave Book: Antifragile by Nassim Taleb Joel's Most Recent Investment: Decred Investment Thesis As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

2 Juli 201828min

Max Motschwiller is a Partner with Meritech Capital, one of the West Coast's leading growth investment firms with over $150Bn in IPOs and a portfolio that includes the likes of Facebook, Salesforce, Snap, Box, Mulesoft and Cloudera just to name a few. As for Max, prior to Meritech he spent 3 years with Kleiner Perkins (KPCB) where he was actively involved with investments in Dropcam (Nest/Google), Duolingo, MyFitnessPal (Under Armour), RelateIQ (Salesforce.com) and Stance. Before joining KPCB, Max worked for 3 years at Summit Partners and was actively involved across Summit's technology portfolio. In Today's Episode You Will Learn: 1.) How did Max make his way into the world of VC with Summit and KP from University? What did that decision-making process look like for Max? 2.) As a career VC, would Max agree with Pat Grady @ Sequoia, "the rate of decay on operating experience has never been greater"? What would Max say are the biggest elements he missed through lack of operational experience? How do the skills required from early to pre-IPO change the type of background required? 3.) Max has said before, "to be a good VC you have to do 4 things well", what are those 4 things? Why does Max believe that picking is the greatest skill to develop? At growth, what does Max mean when he says "the picking is around price"? How do the very best VCs approach price sensitivity? 4.) Question from Rob Ward: Max has mastered network development from an early age, what advice would Max give with regards to developing a network? What did he do well and works? What did he try and did not do well? How does Max think about depth vs breadth of network? How does he apply this to investing and due diligence? 5.) In a time of Softbank and Sequoia's $7Bn fund, how does a firm like Meritech look to compete in such frothy environments? How has growth bifurcated into 2 clear stages? What are the advantages of being a small pure-play growth firm? How does the portfolio construction and return expectation change for you given the fund size and stage of investment? Items Mentioned In Today's Show: Max's Fave Book: Home Deus Max's Most Recent Investment: Amplitude As always you can follow Harry, The Twenty Minute VC and Max on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

25 Juni 201835min

Hemant Taneja is Managing Director @ General Catalyst, one of the world's leading venture firms of the last decade with Airbnb, Stripe, Snapchat, Hubspot and Gusto all in their portfolio. As for Hemant, he has led investments at GC in Stripe, SNAP, Grammarly, Gusto, Livongo, Color Genomics, Class Dojo and more. He also directs the GC Stripe Platform Fund, a $10 million initiative to help start new ventures that are built on top of the Stripe Connect platform. On the educational front, Hemant holds 5 degrees from MIT and sits on the board of Khan Academy. In Today's Episode You Will Learn: 1.) How Hemant made his way from 5 degrees at MIT and wanting to be an academic to pursuing startups in the world of VC with General Catalyst? 2.) Question from Sam @ ClassDojo: What were the hardest elements of establishing GC on the West Coast? With hindsight today, what would Hemant do differently given the chance? How does Hemant think about the development and ability to accelerate the creation of local reputation? What is crucial and works most effectively? 3.) How does Hemant respond to Elad Gil's "everyone is looking for the next truly deep dein to explore"? Why is Hemant so bullish that we are in the "golden age of venture capital"? Why does Hemant believe that "scale" as a key measure has run it's course? What does Hemant's thesis of the future of "unscaling" really mean? 4.) How does Hemant analyse price sensitivity in todays forthy environment? How has his relationship to price changed over time? With regards to price, what have been some of his biggest regrets and learnings drawn from real-world examples? How does Hemant assess reserve allocation? Why does he think pro-rata is a lazy posture? 5.) Hemant has said on boards for over 1,800 hours, so what does Hemant belive makes the truly special board members? How does Hemant think about first building that rapport and "intimacy" with the founder? Secondly, how important does Hemant believe it is to build similar relations with other board members? Which founder exemplifies the best board management in Hemant's mind? Items Mentioned In Today's Show: Hemant's Fave Book: Home Deus Hemant's Most Recent Investment: Spring Discovery As always you can follow Harry, The Twenty Minute VC and Hemant on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It's the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it's a high-quality experience with industry-leading audio powered by Dolby Voice. It's so easy to use, that there's no pin codes or app downloads. Just click a link in your browser, and you're in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com. Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge. So put your people and culture first and find out more on cultureamp.com.

18 Juni 201825min