We are two students, friends, and venture partners for Contrary Capital devoted to learning as much as possible across multiple disciplines. While we value education, we believe that university alone doesn't teach all the tools needed to make sense of the world. We call these Mental Models - concepts, frameworks, or world-views taken from different fields and applied to the world around us. We want to build a toolbox of these models - from some of the greatest thinkers in the world. Support ...
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Most venture capital firms are stress testing the technology and hard hitting questions of what "tomorrow" may look like. Here’s their real-time take…
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Before Katrina Lake was the CEO of a public company, she was a student at Harvard Business School learning the craft. Before Peter Thiel built Paypal and eventually his capital empire, he was a lawyer and studied philosophy. Before Charles Hudson become a venture capitalist, managing his own fund at Precursor ventures, he started off as a product management intern in college. A common bind between all these people is that many have gone down a similar path, yet only a few break out like they ...
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A place to talk about startups, venture capital and tech. For a full download, double-click on sandhillroad.io
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Costanoa Ventures: Amy Cheetham on transitioning from Operating to Investing, building a venture partnership, and the role of hiring in scaling early startups
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"I firmly believe that for-profit technology companies stand the best chance of solving many of the world’s toughest problems and venture lets me be a part of that process." Amy is a Partner at Costanoa Ventures where she focuses primarily on fintech. In addition to deepening the firm’s fintech portfolio in the US, Amy has driven the firm’s expansi…
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Lerer Hippeau's Ben Lerer on the rise of the NY Venture scene, building and scaling a firm, and building moats at the seed stage.
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Ben Lerer is a Managing Partner at Lerer Hippeau. He is the Co-Founder and former CEO of Thrillist, which was acquired by Vox Media in 2022. He chairs the Board of Directors for Urban Upbound and is an Associate Member of the International Academy of Digital Arts & Sciences (IADAS). Lerer holds a BS from the University of Pennsylvania.…
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From YC Hype to Data Moat Strategies: An Interview with Wen-Wen Lam, Partner at Gradient Ventures
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Wen-Wen is a Partner at Gradient Ventures. Previously, Wen-Wen was the CEO & Co-founder of NexTravel (YCW15), a leading corporate travel solution that serviced thousands of customers like Lyft, Twilio, and Stripe. She grew the business to over $100M in annual sales before exiting to Travelperk in 2020. Prior to this, Wen-Wen worked with a number of…
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Halcyon | Driving Change While Doing Good with Kate Goodall
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Kate Goodall (she/her) is the Co-Founder and CEO of Halcyon, an incubator for early-stage impact ventures. Since launching in 2014, Goodall has added an early-stage venture fund (of which she is co-managing director), an angel investing network, microloan fund, and a range of intensive programs, continually seeking to serve increasing numbers of en…
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Visible Hands VC - Daniel Acheampong on Building the Future of Venture Capital
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Daniel Acheampong, Founder, Visible Hands VC Daniel was most recently an Entrepreneur in Resident at MIT designX, where he co-founded a marketplace platform. He was an associate at Summit Partners, where he helped manage the firm’s due diligence process to raise investment funds. Previously, he was a financial analyst at Goldman Sachs, where he sup…
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The Kings of LA: Ajay Relan on the Slauson & Co. Story
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About Ajay: Ajay Relan is an investor, entrepreneur, and community builder. Prior to Slauson & Co., Ajay was a founding Partner at Queensbridge Venture Partners. With a keen focus on brand building and storytelling, Ajay's passion lies in identifying trends and engineering culturally aligned brands. A lifelong Angeleno, Ajay has established a busin…
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E51 Raising $1bn to bringing entrepreneurship to Japan with World Innovation Lab founder and CEO Gen Isayama
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In this episode, Erasmus Elsner is talking to Gen Isayama, co-founder and CEO of World Innovation Lab, a Palo Alto and Tokyo based venture firm investing in growth-stage companies and serving as a bridge between startups and Japanese corporations.00:00 Intro01:30 World Innovation Lab04:10 From Japanese lawyer to Silicon Valley VC09:10 From DCM to…
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E50 Establishing a growth equity firm with Left Lane Capital founding partner Dan Ahrens
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In this episode, Erasmus Elsner is talking to Dan Ahrens, founding partner at Left Lane Capital, a New York based venture capital and early growth equity firm that invests in high-growth internet and consumer technology businesses. 00:00 Intro 02:43 Consumer vs. enterprise tech 05:09 Getting into venture 07:54 Raising Left Lane I 10:35 Investing …
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E49 Cooking up the future of digital food halls with Byte Kitchen founder Divyang Arora
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In this episode, Erasmus Elsner is talking to Divyang Arora, founder and CEO of Byte Kitchen about cooking up the future of digital food halls with Byte Kitchen founder Divyang Arora. 0:00 Intro 1:24 2 minute elevator pitch 4:27 Going all in 8:07 Business Model 14:52 The Byte Kitchen playbook 18:52 Optimal Partner Restaurant Profile 25:39 End custo…
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E48 Protecting passwords through open-source software with Bitwarden CEO Michael Crandell
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In this episode, Erasmus Elsner is talking to Michael Crandell, CEO Bitwarden about scaling open-source password manager Bitwarden. 00:00 Intro 00:50 What is Bitwarden 03:22 From side hustle to venture-backed 06:36 Joining a Bootstrapper at Series A 09:58 Open-source GTM 13:25 Open-source defensibility 15:35 Community vs. enterprise edition 17:37 …
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E47 Your fund size is your strategy with Kyle Harrison, GP at Contrary
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In this episode, Erasmus Elsner is talking to Kyle Harrison, general partner at Country about everything from the economics of whale hunting, the venture product offering to his recent joining of Contrary. 00:00 Intro 01:11 Way into venture 04:58 Time of reflection 07:24 The under-innovated venture model 10:46 Your fund size is your strategy 16:16…
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"Bada** Woman" | The Chingona Ventures Journey with Samara Hernandez
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About Samara: Samara Mejia Hernandez is the Founding Partner and Managing Director of Chingona Ventures, a Venture Fund that focuses on rapidly changing sectors and founders with experiences that uniquely position them to build startups in underserved growth markets. The fund has $60MM in AUM and has made over 40 investments across technology secto…
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The King of Twitter | Mac Conwell on Building Rarebreed Ventures
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Key takeaways: --Your limit to opportunities is your own mindset. --Founders should build their network consistently over time. It will help you understand the fundraising journey, and bring you honest feedback about how long the journey will take. --Early stage investors are "founder evaluators" more so than "business evaluators". Help them believ…
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E46 Uncovering tax credits (aka free money) for startups with MainStreet founder and CEO Doug Ludlow
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In this episode, Erasmus Elsner is talking to Doug Ludlow, co-founder and CEO of MainStreet, which helps startups and small businesses uncover tax credits. 00:00 Intro 01:05 Hipster 05:09 Happy Home Company 07:10 Starting MainStreet 11:22 The nature of Tax credits 16:03 The Path Act 17:52 The MainStreet Product 19:14 Customer success stories 20:4…
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E45 Building a nextgen, authentic professional social network with Candor founder Kelsey Bishop
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In this episode, Erasmus Elsner is talking to Kelsey Bishop founder and CEO of Candor, which is a nexgen, authentic social network. 00:00 Intro 01:02 What is Candor 03:25 Single player mode 03:56 Kelsey’s background 06:19 Employee-culture fit 08:31 Getting started 10:31 Migrating from bubble 11:38 Raising the Seed 12:42 Getting pre-empted 13:50 R…
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E44 Shipping an open-source, low code enterprise tool builder with Appsmith founder Abhishek Nayak
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In this episode, Erasmus Elsner is talking to Abhishek Nayak the co-founder and CEO of Appsmith, which is an open-source, low code internal tool builder. 00:00 Intro 03:15 Entrepreneur in Residence at Accel 05:52 Third time at the Rodeo 09:55 Validating a startup idea at his wedding 11:38 Built for Internal facing apps 13:48 The Appsmith Customer…
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Chloe Capital's Elisa Miller-Out on lessons for leaders scaling a company, what its like on the investor side of the table, and a word of advice for the next gen of Founders.
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Elisa Miller-Out, Managing Partner Elisa Miller-Out is Chloe Capital’s Co-Founder and Managing Partner. She is an experienced serial tech entrepreneur, having founded and led seven companies over 20+ years. She is an experienced investor, having invested in 45 companies, in addition to executing 10 M&A transactions. Elisa is also an active board di…
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Eric Tarczynski from Contrary on: spotting Hyper-Growth, tips for first time builders and the impact of price compression at the early stage
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Eric is the founder and GP of Contrary. Contrary's portfolio includes hyper-growth companies like Anduril, Ramp, and Zepto. Key Takeaways: Identify the brightest people in the world first, then build infrastructure to support them for their entire life Identify LPs who believe in you emotionally before they believe in your model (not people in weal…
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E43 Opening a global hub for tech entrepreneurs at UC Berkeley with SkyDeck founding GP Chon Tang
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In this episode, Erasmus Elsner is talking to Chon Tang, the founding GP of the Skydeck Fund. Chon is an experienced Silicon Valley engineer, entrepreneur and investor. He was formerly founding partner and Managing Director of Junzi Capital Engineering, a leading quantitative hedge fund investing in the commodity space. He has been actively investi…
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E42 Taking Zoom meetings like a pro with Fathom (YC W21) founder Richard White
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In this episode, Erasmus Elsner is talking to Richard White, the serial entrepreneur behind Uservoice and Fathom.video. Richard is a design engineer and product visionary who has been in the first YC batch with Justin Khan and Emmett Shear for Kiko (YC S05) and most recently came back to the YC W21 to see how startup kids are doing the tricks today…
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Let's Talk Consumer! Redpoint Ventures' Meera Clark on thesis driven investing, spotting resilient founders and building your brand in venture
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Topics covered: Finding founders through thesis-driven investing Spotting resilient founders- are they building because this product needs to exist What this new market means for deal pacing Driving value add for portfolio companies The talent recruiting landscape Building your brand in venture About Meera: I’m an early stage investor at Redpoint V…
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E41 Replacing credit bureaus one API integration at a time with Argyle founder Shmulik Fishman
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In this episode, Erasmus Elsner is talking to Shmulik Fishman, founder and CEO of Argyle, about raising the Series A through an investment memo and the firm’s mission of making user-permissioned employment data ubiquitous and reinvent credit decisioning for lenders and consumers. 00:00 Intro 00:56 What does Argyle do? 03:17 Experiencing the pain …
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E40 The world is broken, let's fix it with 8VC founding partner Drew Oetting
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In this episode, Erasmus Elsner is talking to Drew Oetting, founding partner of 8VC, about building a multi-billion venture firm from the ground up with Joe Lonsdale. 00:00 Intro 01:05 Operation Mask 06:33 Resilience 12:54 Views on Venture 20:06 Building 8VC / Addepar 26:30 Raising the maiden fund 30:48 8VC Investment Thesis 40:01 Drew as a VC 50:5…
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Startup Fundraising 101 with Nathan Beckord, CEO of Foundersuite
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Nathan Beckord is the CEO of Foundersuite.com and VentureArchetypes.com. On the consulting and advisory side, he mainly works with early stage internet, B2B software, mobile, and consumer product startups. He is also interested in platforms, markets, and networks. Nathan has worked with several crowdfunding companies, such as Kickstarter and Appbac…
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E39 Trailblazing the silver tech category with Seth Sternberg co-founder of home-care unicorn Honor
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In this episode, Erasmus Elsner is talking to Seth Sternberg the co-founder and CEO of Honor, which is a managed marketplace for in-home care that has recently announced a USD 370m Series E led by Baillie Gifford. 00:00 Intro 01:19 Elevator pitch 02:19 Original inspiration 05:28 The Meebo experience 08:06 Serial founder problems 09:06 Getting the…
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The SLOW Burn - Sam Lessin on thinking outside the box, investing in human potential, and what he has learned building Slow Ventures
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Sam Lessin - General Partner at Slow Ventures. He has co-founded two companies, Fin and Drop.io (acquired by Facebook in 2010). Between 2010 and 2014 Sam was a VP of product management at Facebook, where he managed the People, Places, and Things product group and the Identity product group. Sam started his career at Bain and Company and attended Ha…
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E38 Helping brands build sustainable products with Novi Connect found Kimberly Shenk
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In this episode, Erasmus Elsner is talking to Kimberly Shenk of Novi Connect, B2B marketplace to help brands build and manufacture transparent products, which recently announced a $10.3M Series A led by Greylock00:00 Intro 02:04 Getting started with Naked Poppy 04:09 From Naked Poppy to Novi Connect 05:17 Sustainable Chemicals Market 07:30 Kimber…
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"It Takes a Village" - From Techstars to Launching The Fund with Jenny Fielding
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Jenny Feilding, General Partner at The Fund, Adjunct professor at Columbia, and entrepreneur joins us on the Road Untraveled this week. Jenny is a pre-seed investor and mentor to hundreds of founders around the world. She is a 2x entrepreneur herself and knows how challenging it is to build great products, inspire a team and keep the lights on. She…
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Hunter Walk (Homebrew) - The Screendoor Initiative, lessons learned in big tech, & how to enjoy the journey
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Hunter Walk, Co-founder and Partner at Homebrew. Homebrew is a seed-stage venture firm with investments like Chime, Plaid, Gusto, and many more. Prior to Homebrew, Hunter received his BA from Vasser and MBA from Stanford and then spent time at Youtube as a director of product management. Episode Highlights: Lessons learned at Google and Youtube as …
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The RAISE Conference - Talking LP/GP relationships with Ben Black (Akkadian Ventures)
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Key Take-Aways Ben Black - Founder and CEO of Akkadian Ventures: 1. "Venture capital requires a level of trust that is unlike any other business because you find out your failures first before you figure out your wins. And if you want to press personal relationships and really put a lot of pressure on them, deal with failure together." 2. Tune out …
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E37 Finding regulatory moats at the Series A with Jordan Nof of Tusk Venture Partners
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In this episode, Erasmus Elsner is talking to Jordan Nof of Tusk Venture Partners, a venture firm that invests in early-stage consumer technology startups operating in heavily regulated markets. 00:00 Intro 01:39 Investment thesis 2022 02:36 Lithic 05:02 Tusk Venture Partners 08:46 Meeting Bradley Tusk 12:52 Regulatory investment thesis 14:58 The…
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David Fialkow (General Catalyst) - Helping founders communicate in tough times, building diverse investment teams and what it takes to win.
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I had an insightful conversation with David Fialkow, Co-founder and Managing Director of General Catalyst, a venture capital firm that partners with founders from seed to growth stage to build companies that withstand the test of time. Key Take-Aways From This Episode: 1. David speaks about the importance of connection and the value of working with…
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Lightspeed Venture Partners - Barry Eggers on building a global venture brand, navigating LP relationships for emerging managers, and the Lightspeed Scout Fund.
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On today's episode, I am joined by Barry Eggers, Founding Partner at Lightspeed Venture Partners. Episode Key Takeaways: Barry shares with us his 20+ year journey from a new venture firm in the early 2000s to the global powerhouse that is Lightspeed today. We get Barrys take on the state of venture and his position on acknowledging and preparing fo…
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E36 Running the world's largest trust experiment with Couchsurfing founder Casey Fenton
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In this episode, Erasmus Elsner is talking to Casey Fenton, founder of Couchsurfing and Upstock, about the early days for Couchsurfing when Casey was pioneering what has since become known as the “sharing economy” and how is is now bringing the sharing economy to the cap table with Upstock. 00:00 Intro 01:13 The Couchsurfing proof-of-concept 02:4…
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E35 Launching a startup acquisition marketplace with MicroAcquire founder Andrew Gazdecki
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In this episode, Erasmus Elsner is talking to Andrew Gazdecki, founder of MicroAcquire. The episode was recorded when MicroAcquire was still a fully bootstrapped one person company. A few weeks later MicroAcquire announced that it had raised a $6.3m Seed round led by Bessemer Ventures. 00:00 Intro 01:09 What is MicroAcquire? 02:55 Buying a micro-Sa…
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E34 Tackling the formalwear industry with Queenly co-founders with Trisha Bantigue and Kathy Zhou
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In this episode, Erasmus Elsner is talking to Queenly co-founders Trisha Bantigue and Kathy Zhou about building a consumer marketplace and tackling the formalwear industry. 00:00 Intro 00:56 The Queenly Elevator Pitch 01:52 Launching Queenly during lockdown 04:04 The pageant dress market 08:06 Formal wear resale market microstructure 10:16 The Quee…
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E33 Catching the perfect privacy wave one consent at a time with Didomi co-founder Jawad Stouli
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In this episode, Erasmus Elsner is talking to Didomoi co-founder and CTO Jawad Stouli about building consent management platform Didomi for the perfect privacy wave. 00:00 Intro 00:46 Early days of Didomi 03:29 Fighting a US patent troll 08:14 Building the Didomi MVP 12:18 Developer-centric platform approach 14:46 Early costumers: self-service vs. …
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E32 Incubating a space factory at Founders Fund with Delian Asparouhov
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00:00 Intro 00:24 Welcome to Miami 01:08 Operators Podcast 03:21 Finding the right guests 06:54 Delian’s founder/operator 08:22 Cohort analysis with Keith at Square 10:30 Nightingale 12:24 Operating experience at Teespring 14:24 Varda Space 17:45 Splitting time between Varda and FF 19:45 Varda Space incubation 23:50 Delian as an investor at Founder…
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E31 Building the future of remote work with Remote.com founder Job van der Voort
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In this episode, Erasmus Elsner is talking to Remote.com founder Job van der Voort about building the future of remote work. 0:00 Intro 00:49 The first two years of Remote 02:19 Preparing for the perfect Storm at Gitlab 06:17 Leaving Gitlab 10:47 Business model 14:10 Legal war chest 15:20 Fintech-payment layer 16:20 SaaS layer 17:52 Pricing 19:47 C…
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E30 Fintech investing with Better Tomorrow Ventures co-founder Sheel Mohnot
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In this episode, Erasmus Elsner is talking to Sheel Mohnot, co-founder of Better Tomorrow Ventures about his journey as a founder, angel investor and co-founder of Better Tomorrow Ventures. 00:00 Intro 01:11 Guest appearance on a Justin Bieber/Ariana Grande music video 03:16 The “pronoia” mindest 03:16 The “pronoia” mindest 05:04 Sheel’s background…
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E29 "Billon Dollar Loser" author Reeves Wiedeman on the epic rise and fall of WeWork
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In this episode, Erasmus Elsner is talking to Reeves Wiedeman, author of "Billion Dollar Loser: the epic rise and fall of WeWork". 00:00 Adam's intro 01:11 Intro 01:38 Adam Neumann 04:11 Adam's art of persuasion 05:41 Book title 08:10 Writing process 13:01 WeWork evolution and business model 16:21 Tech vs. real estate company 19:25 WeWork community…
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E28 Inside DCM’s Record IPO Streak with Kyle Lui, Partner at DCM
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In this episode, Erasmus Elsner is talking to Kyle Lui, Partner at DCM, about the recent IPO roll that DCM has been on. The Menlo Park-based firm has generated a 61x return on investments that have gone public in the past two years. Kuaishou is the standout, with its market cap to entry valuation at 2,000x. 00:00 Intro 00:50 Who is Kyle Lui 01:33…
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Navigating Your Fundraise Journey with Jean-Pierre Adechi, CEO at Wheeli
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Jean-Pierre Adechi, Founder & CEO, Wheeli Key Takeaways 1. The system isn't merit based- build relationships and a network that can help you build trust in the communities that will allow you to access the resources you need to succeed 2. Lean on advisors and people from the community to better identify folks who want to help you navigate the syste…
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E27 Replacing PDF attachments one Docsend at a time with founder and CEO Russ Heddleston
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In this episode, Erasmus Elsner is talking to Russ Heddleston, founder of Docsend. The episode was recorded one month before the announcement that DocSend would be acquired by Dropbox for $165m. 00:00 Intro 00:37 What is Docsend 01:51 Selling Pursuit to Facebook in a talent acquisition 04:12 Leaving Facebook and starting Docsend 07:03 Product ide…
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E26 Deciphering Super Founders with author and DCVC partner Ali Tamaseb
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In this episode, Erasmus Elsner is talking to Ali Tamaseb, partner at DCVC, about his recently launched book "Super Founders: What Data Reveals About Billion-Dollar Startups". 00:00 Intro 01:00 Who is Ali? 03:02 Spark of motivation for the Super Founders book 05:49 Primary data collection 08:13 Data set: timeframe and selection criteria 10:28 The…
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E25 Bottoms-up product and go-to-market strategy with product leader and investor Vivek Saraswat
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In this episode, Erasmus Elsner is talking to Vivek Saraswat, who has been a venture investor at Mayfield at the time of the recording and previously a product leader at Docker/VMware/AWS. Since recording this episode, Vivek has joined Immersa as a founding VP of product. 00:00 Intro 00:56 Who is Vivek? 03:12 Joining Mayfield 05:07 Portfolio compan…
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E24 Bootstrapping from zero to $1m+ in ARR with Justin Jackson, mega maker of Transistor.fm
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In this episode, Erasmus Elsner is talking to Justin Jackson, co-founder of Transistor.fm about his journey as a mega maker, bootstrapping his podcast hosting and analytics platform to $1m+ in ARR in less than 3 years. 00:00 Intro 01:55 Getting Real 04:30 Business is like surfing 7:43 Selling ice cream on a busy beach 11:33 Why your busines…
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The Godfather of Pre-seed Investing: A Conversation with Charles Hudson of Precursor Ventures
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Charles Hudson is Founder and Managing Partner at Precursor Ventures Key Takeaways: 1. Volume matters- do you get to meet enough companies in a year. They meet 3-4k companies and make 30 investments. You can't identify high quality founders if you don't see enough of them. 2. Some investors are great product people, some are good at market structur…
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E23 Insights from building a VC firm in public with Initialized Capital founder Garry Tan
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In this episode, Erasmus Elsner is talking to Garry Tan, co-founder of Initialized Capital about his journey as a content creator, founder and managing partner at Initialized Capital. 00:00 Intro 02:02 Garry's Twitter game 06:00 Keeping up the content cascade 08:12 Getting started on YouTube 10:50 Paying it forward at scale 14:45 Respecting the aud…
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E22 Engineering the atomic cockroach of databases with Cockroach Labs co-founder Spencer Kimball
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In this episode, Erasmus Elsner is talking to Spencer Kimball, co-founder and CEO of Cockroach Labs about building a database unicorn backed by some of Silicon Valley's top venture firms, incl. Benchmark, Sequoia Capital and Index Ventures. After recording the episode, Cockroach Labs raised $160m on a $2bn valuation in January 2021, reflecting the …
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