Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California.
1.) Entry into the World of Sales:
2.) The Sales Playbook:
3.) The Secrets to Pricing and Discounting:
4.) The Hiring Process:
5.) The Onboarding:
Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired. If that was not enough, Sheel is also a master at measuring the width of swimming pools and making cameo appearances in music videos with Justin Bieber.
1.) Entry into Venture:
2.) The Power Law:
3.) Venture Capital has Never Been Less Collaborative:
4.) The Biggest Wins and Misses:
5.) Emerging and Frontier Markets:
Sheel's Favourite Book: Enders Game
Marcelo Claure is an entrepreneur and investor who has founded and led some of the world’s most iconic businesses. He is currently the Chairman & CEO of Claure Capital, a newly founded multi-billion-dollar global investment firm. Before this, Marcelo was COO @ Softbank Group, the world’s largest technology investment company.
Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more.
Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade.
David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more.
Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few.
Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital.
Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ’s total value.
Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN.
Nick Shalek is a General Partner @ Ribbit Capital, specializing in fintech they are one of the most successful venture firms of the last decade with a portfolio including Robinhood, Coinbase, Revolut, Nubank and more.
Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more.
Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives.
Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures. Their portfolio includes SpaceX, Wish, Anduril, Flexport, and WorkRise (formerly Rigup) to name a few.
David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora.
1.) How do you assess your relationship to price and price sensitivity?
2.) When is the time to pay up and have less price discipline?
3.) When should we remain disciplined and not pay up for a deal and walk away because of price?
4.) Of the deals you have paid up for, did their growth rate justify the high entry price?
5.) Knowing all you know now on price, how do you advise younger investors today?
Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of 'The Hustle.' He is also an advisor and investor in early-stage companies.
1.) Entry into Growth and Marketing:
2.) Why You Need Growth Hires Pre Product Market Fit:
3.) Building Your Growth Team:
4.) The Future is Content:
5.) WTF Really is Community:
Mo Koyfman is the Founder and General Partner @ Shine Capital, who announced earlier this year Shine II, a $200M early-stage fund, and Shine Opportunities I, a $100M vehicle. Prior to founding Shine, Mo was the Managing Member @ Moko Brands where he made angel investments in Coinbase, Polychain, Harry's to name a few. Before Moko, Mo spent over 7 years as a General Partner @ Spark Capital where he made investments in Plaid, Warby Parker, Skillshare and Hivemapper, to name a few. Finally prior to Spark, Mo spent over 5 years at IAC where he oversaw group of companies that included Connected Ventures, parent of Vimeo, CollegeHumor & BustedTees.
1.) From Entrepreneurial Parents to IAC, Spark Capital and Founding Shine:
2.) Investment Firm vs Investment Partnership:
3.) How To Win in Venture:
4.) The Lessons: Success and Failure:
Mo's Favourite Book: Portnoy's Complaint by Philip Roth
Sameer Shariff is the Co-Founder and CEO @ Cambly, the company that allows you to become fluent faster through one-on-one video chat lessons with native English tutors. To date, Sameer has raised over $60M with Cambly from the best including Jeremy Levine @ Bessemer, Sarah Tavel @ Benchmark, Monashees, YC and more. Prior to founding Cambly, Sameer spent close to 5 years at Google on the Search Quality team and became the Tech Lead of the Search experiments team helping make experimentation a core part of the launch process.
1.) Entry into Startups and Co-Founding Cambly:
2.) The Trials and Tribulations of Leadership:
3.) The Fundraise that Led to Cash Flow Positive:
4.) Marketplace Dynamics 101:
Sameer's Favourite Book: The Most Human Human: What Artificial Intelligence Teaches Us about Being Alive
Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped define and grow the Product Management function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter and prior to Twitter spent over 6 years as a Group Product Manager @ Google. Today Shreyas has invested and advises some of the best including advising Airtable, Kalshi, Lendflow, to name a few.
1.) Entry into Product:
2.) Product Management 101:
3.) Metrics 101 & How To Use Them:
4.) Three Types of Product Leader:
Kirsten Green is the Founder and Managing Partner @ Forerunner Ventures, one of the leading firms of the last decade investing at the intersection of innovation and culture. As a founder, Kirsten has led efforts to raise over $2B+ from leading institutional investors and invest in more than 100 companies. She currently serves as a board member at Glossier, Ritual, Faire, Hims & Hers, and Curated, to name a few. She has also invested in other smash hits including Chime, Jet, Warby Parker, Hotel Tonight and many more. Due to her immense success, Kirsten has been honored in Time’s 100 Most Influential People and named a Top 20 Venture Capitalists by The New York Times in 2018 & 2017. Prior to Forerunner, Kirsten was an equity research analyst and investor at Banc of America Securities.
1.) Entry in Venture at 40 and Founding Forerunner:
2.) Fund Management and Leadership:
3.) The Venture Landscape Today and Forerunner's Position:
4.) Parenting, Relationships and Life:
Jim Lanzone is the CEO @ Yahoo, a company that today reaches nearly 900 million people around the world and is the third largest property on the Internet. Prior to Yahoo, Tim was the CEO of Tinder, the world’s most popular app for meeting new people, downloaded by more than 400 million people. Before Tinder, Jim spent a decade as President and CEO of CBS Interactive, a top 10 global Internet company with brands ranging from CBS All Access to CNET. He joined CBS Interactive in 2011 when CBS Corporation purchased Clicker Media, where he was founder and CEO. Before founding Clicker, Jim served as CEO of Ask.com (formerly Ask Jeeves).
1.) Jim's Entry into the World of Startups:
2.) Leadership 101:
3.) Crashes and Turnarounds:
4.) The Yahoo Turnaround:
Items Mentioned in Today's Episode:
Jim's Favourite Book: Team of Rivals: The Political Genius of Abraham Lincoln
Today we deconstruct the canonical question in early-stage sales. Does the founder need to create the sales playbook? Then secondly, if not, should the first sales hires be reps or a sales leader? Today we are joined by 7 of the best sales leaders to share their thoughts.
Jordan Van Horn is a Revenue Leader @ Montecarlo. Previously Jordan spent 4 years with Segment and before that spent another 4 years at Dropbox.
Oliver Jay (OJ) most recently spent 6 years at Asana where he was hired as the company’s first revenue leader. Before Asana, OJ spent 4 years at Dropbox where he scaled the sales team from 0 to 50 while tripling ARR.
Dannie Herzberg is a Partner @ Sequoia Capital and previously spent 4 years at Slack as their Head of Enterprise Sales. Before Slack, Dannie spent 5 years at Hubspot building sales, opening an SF office, and then joining product to launch CRM & platform.
Zhenya Loginov is the CRO @ Miro, where he runs the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas.
Kyle Parrish is VP Sales @ Figma, where he has scaled the sales team from 0 to over 100 people in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, where he scaled the Austin, Texas office from 3 to over 80 people.
Sam Taylor is the VP of Sales and Customer Success @ Loom, at Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader.
Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.
Mitch Tarica is Head of North America Sales at Zoom Video Communications. Before Zoom, Mitch spent over 5 years at RingCentral and before RingCentral, Mitch was at Oracle for over 7 years in numerous different sales roles.
1.) What is the right definition for a "sales playbook"?
2.) When is the right time to change your "sales playbook"?
3.) What are the biggest mistakes or misnomers made around the "sales playbook"?
4.) Should the founder be the one to create the first sales playbook or can it be a sales leader?
5.) When is the right time for founders to hire their first sales leaders?
6.) For the first sales hire, should founders hire sales reps or a sales leader?
7.) When should you hire a rep vs a sales leader? What are the nuances?
Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most revolutionary products in society from the iPhone and iPod to more recently founding Nest, creating the Nest Thermostat, leading to their $3.2BN acquisition by Google. Tony recently released Build, a masterclass taking 30 years of product and company building lessons and packaging them for you, check it out here.
1.) On reflection, what would Tony most like to change about his childhood?
2.) As a leader, should the company you are building be a family or a team?
3.) How to solve the loneliness of being a solo founder?
4.) How to think differently in the face of adversity?
Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few. As for Kyle, before moving to the world of venture and crypto, he founded Pristine, a health IT startup that raised more than $5M in VC, and was acquired by Upskill.
1.) The Founding of Multicoin Capital:
2.) Crypto Investing in 2022:
3.) Constructing a Crypto Portfolio in 2022:
4.) Multicoin vs Traditional Venture Firms:
Kyle's Favourite Recent Reading: Eugene Wei
Kyle's Most Recent Investment: Delphia
Sam Taylor is the VP of Sales and Customer Success @ Loom, an essential tool for hybrid and remote teams allowing you to record quick videos of your screen and cam. At Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist, Sales Development, Global Customer Support, Revenue Ops + Strategy and Sales Enablement. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader.
1.) Entry into the World of Sales:
2.) Sales People Should Be Customer Therapists:
3.) The When and The Who:
4.) How To Hire The Best: The Process
Des Traynor is a Co-founder and the Chief Strategy Officer of Intercom, the modern customer communications platform that unifies every aspect of the customer journey. To date, Intercom has raised over $238M from some of the best including Index, ICONIQ, Kleiner, GV, and Bessemer. As for Des, before co-founding Intercom, he was a UX consultant, a university lecturer in computer science, and also a Ph.D. researcher. Des is also a prolific angel investor with a portfolio including the likes of Stripe, Algolia, Notion, Miro, and many more.
1.) Origins of Intercom:
2. Two of the Biggest Myths in Startups: Being First and Defensibility
3.) Product 101: A Masterclass on Product:
4.) Moving to Enterprise:
5.) The Makings of Great Product Marketing:
6.) Angel Investing 101: From Stripe to Miro to Notion:
Des' Favourite Book: How Will You Measure Your Life by Clayton Christensen
Peter Singlehurst is the Head of Private Companies at Baillie Gifford. As of 31st March 2022, funds under Baillie Gifford's management and advice totaled £277bn. The firm is owned and run by 51 of its senior executives who operate as a partnership, a structure that has endured for over a century. As for Peter, he has been with Baillie Gifford since graduating from Durham University 12 years ago and has backed some astonishing breakouts such as Wise, Grammarly and Zymergen to name a few.
1.) Entry into Venture:
2.) The Biggest Misnomers and Misalignments in Venture:
3.) Baillie Gifford: Constructing a Portfolio with £277BN:
4.) Peter Singlehurst: The Investor:
Peter's Fave Book: The Myth of Sisyphus
Peter's Most Recent Investment: Grammarly
Luc Levesque is currently the VP of Growth at Shopify and also advises companies like Twitter, Pinterest, and Quora. At the age of 21, Luc founded TravelPod, the world’s first travel blogging platform. 10 years later, TravelPod was acquired by Expedia, where Luc led the creation of two award-winning products: TripWow and the Traveler IQ Challenge. Luc then served as an executive at TripAdvisor, where he built and led the growth team which helped TripAdvisor become the world’s largest travel site. Luc was then recruited by Mark Zuckerberg to Facebook where he was an executive and led the creation of Messenger Kids.
1.) Entry into Growth:
2.) Growth and Viral Loops:
3.) Growth: Building the Team:
4.) Growth: The Action:
Matt Mullenweg is the Founder of Automattic, the force behind WordPress, Tumblr, WooCommerce, Jetpack, Longreads, Simplenote, Pocket Casts, and more. What started as a simple open-source blogging platform, Matt has turned into one of the most significant internet properties of our generation, now powering over 43% of sites on the internet. Alongside Automattic, Matt also invests through Audrey Capital and has backed the likes of Stripe, SpaceX, Gitlab, and Sendgrid to name a few.
1.) The Origins of WordPress:
2.) Matt Mullenweg: The Essence of Leadership:
3.) Matt Mullenweg: The Person:
4.) WordPress: The Company:
Matt's Favourite Book: Principles by Ray Dalio
Mike Chalfen is a solo GP with Chalfen Ventures and one of the most respected and successful early-stage investors in Europe over the last two decades. Among Mike's incredible portfolio includes the likes of King.com (makers of Candy Crush), Houzz, Tipalti, Snyk, and Tray.io, to name a few. Some incredible facts on Mike, he has a 15x career track record, he has a portfolio value of over $40BN+ and he joined the venture industry, the year of my birth!
1.) Entry Into Venture and The Broken Customer Experience of VC:
3.) Portfolio Construction 101:
3.) The Market 101:
4.) Boards 101:
Mike's Favourite Books: Don't Let's Go to the Dogs Tonight: An African Childhood, Days Without End
Mike's Most Recent Investment: Opply
Scott Belsky is an entrepreneur, master of product reviews, author, investor, and currently serves as Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud.
Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most game-changing products in society from the iPhone and iPod to more recently founding Nest.
Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here.
Kayvon Beykpour is one of the most prominent product leaders of the last decade. For the last 7 years, Kayvon has been at Twitter where he led all of the teams across Product, Engineering, Design, Research and Customer Service & Operations.
Aparna Chennapragada is Chief Product Officer @ Robinhood, the company revolutionising consumer finance with commission-free investing.
1.) What makes a truly great product review?
2.) What are the biggest mistakes that product leaders make when leading product reviews?
3.) Who should be invited to the product review? How does this change with scale? How does this change in a world of remote work and Zoom?
4.) Who should set the agenda for the product review?
5.) How can leaders assign accountability and ensure that the follow-ups from product reviews are executed on?
6.) How can leaders ensure that they do not dominate product reviews with the weight of their words? How can they give designers and devs the space to share their thoughts without being judged?
Daniel Yanisse is the co-founder and CEO of Checkr, a leading HR technology company, currently valued at $5 billion. During the journey, Daniel has raised over $679M for Checkr from some of the best including Accel, Bond, Coatue, GV, Elad Gil and IVP to name a few. Prior to Checkr, Daniel was a software engineer and helped develop prototypes of the Mars Rover for NASA. Daniel has been recognized in Forbes “30 Under 30” and recently Checkr was recognized by Forbes as one of America’s best start-up employers.
1.) The Origins of Checkr: The $5BN Company
2.) Hiring 101:
3.) Fundraising 101:
4.) Going into Enterprise:
Daniel’s Favourite Book: Accelerate: The Science of Lean Software and Devops: Building and Scaling High Performing Technology Organizations
Bill Gurley is a General Partner @ Benchmark Capital, Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow.
Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.
Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on.
Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades.
Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade.
Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify and many more incredible companies.
Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and many more.
1.) How does the current environment compare to prior busts?
2.) How will the changing interest rates impact the startup funding climate moving forward?
3.) Why is the rate of inflation the only true metric which reveals the ultimate fate of the economy?
4.) What are the world's leading investors telling their founders?
5.) How are the best investors in the world thinking through reserves management?
Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify, and many more incredible companies. As for Sonali, Sonali led Accel’s investments in Avito (acquired by Naspers), Spotify (NYSE: SPOT), Primer, Monzo, Letgo (acquired by Naspers), Kry/Livi, Soldo, Hopin, and Sennder. Prior to Accel, Sonali was with Atlas Venture (now Accomplice). She also previously served on the board of Match.com (NASDAQ:MTCH).
1.) From Small Town in India To Leading Venture Capitalist:
2.) Firm Building: Accel:
3.) Sonali: The Investor:
4.) Decision-Making and Risk:
Sonali's Favourite Book: A Fine Balance
Sonali's Most Recent Investment: BeReal
Henri Pierre-Jacques is Managing Partner of Harlem Capital, on a mission to change the face of entrepreneurship by investing in 1,000 diverse founders over the next 20 years. From a kitchen table with his Co-Founder, Jarrid, Henri has scaled Harlem in just a few years to their latest fund last year of $134M, well over-subscribed from their $100M target. Prior to Harlem, Henri was in Private Equity at ICV Partners, and before PE was an Investment Banker at Bank of America Merrill Lynch.
1.) From Kitchen Table to $134M Fund:
2.) The First Fundraise: Harlem I
3.) Building the Firm: The Strategy:
4.) It Is Time For Change:
Henri's Most Recent Investment: Mueshi
Zhenya Loginov is the CRO @ Miro, the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, I run the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people, expanded the product-market fit into the Enterprise and grew revenue 6x, leading to their acquisition by Twilio for $3.2Bn. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas.
1.) Entry into Sales as an Outsider:
2.) The Sales Playbook: What, Why and How:
3.) Hiring the Team:
4.) Laying the Groundwork: The Onboarding Process:
Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX, the CEO of VaynerMedia and the Creator & CEO of VeeFriends. Now Gary is a content machine and documents his life as a CEO daily through his social media channels which have more than 34 million followers and garnishes over 272 million monthly impressions/views across all platforms. He is also a five-time New York Times Best-Selling Author and is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber. If this was not enough, Gary serves on the board of GymShark, MikMak, Bojangles Restaurants, and Pencils of Promise.
1.) From Wine Library to One of The Great Angels in Tech:
2.) Hard Lessons Learned and Insecurity:
3.) Money and Success:
4.) Resource and Time Allocation: