My guest today is Henrique Dubugras, co-founder and CEO of Brex, an all-in-one finance account for businesses. Brex recently raised funding at a valuation of over 7 billion dollars despite being founded only four years ago. In our conversation, we cover Brex’s transition from a credit card for start-ups to the central account for businesses, why building that central account was orders of magnitude more difficult than expected, and the difference between building a business in Brazil and the US. We also discussed Henrique’s term horizon for building Brex and how that impacts his decision-making for the business. Please enjoy my conversation with Henrique Dubugras. For the full show notes, transcript, and links to mentioned content, check out the episode page here.-----Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:02:53] - [First question] - The state of the B2B financial world before Brex[00:06:29] - How such a high margin space was generally underserved[00:08:24] - What the first version of the Brex card looked like[00:10:48] - How long it took to build and launch their infrastructure[00:11:13] - Why market penetration is so low for cards in B2B businesses[00:13:14] - How he thinks about this landscape in Brazil versus the US[00:14:55] - What interchange and high margins allows him to pass on to the consumer[00:16:23] - Brex’s first revenue event[00:17:38] - What the biggest hurdle was to overcome when they launched[00:19:02] - Key marketing strategy early on and what made it successful[00:21:16] - Continued distribution lessons they learned from their initial success[00:22:39] - Building an effective sales force to push their product[00:24:41] - What makes the current landscape so fertile for fintech businesses[00:27:12] - Analysis of their unique funding round dynamics[00:28:42] - Their second product and the insight that lead to that decision[00:31:05] - Darkest moments while trying to build their central account[00:31:50] - What their central account allows them to facilitate writ large[00:35:27] - Notable differences between entrepreneurship in Brazil versus the US[00:38:55] - Observations on inefficiencies in the US startup space[00:40:16] - Pros, cons, and costs of being largely remote[00:41:50] - Keys to building a successful hiring pipeline[00:44:05] - Lessons learned about decision making and optimization[00:45:39] - Developing an effective skill set to convince other people of anything[00:47:35] - What excites him about being a part of Brex lately[00:49:13] - What excites him about the future in general[00:50:39] - His business philosophy and the set of principles that guide him [00:52:03] - Nuances that make focusing on a single problem so attractive[00:53:51] - Long term infrastructure decisions that will pay off in the end[00:55:12] - Thoughts and hi perspective on cash flow in general[00:58:18] - The kindest thing anyone has ever done for him

My guest today is Justin Fishner-Wolfson, founder of 137 Ventures, a venture capital fund focused on providing liquidity solutions to founders, investors, and employees of private businesses. In our conversation, we discuss what early career experiences led Justin to start 137 Ventures, the counter-intuitive information asymmetry between public and private markets, and the interesting trend of digitization in the physical world. I hope you enjoy my conversation with Justin. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:03:47] - [First question] - Why he started 137 Ventures and what’s unique about it[00:05:31] - Overview of secondary equity markets in the tech sector[00:07:06] - Step by step process of how a secondary market investment works[00:09:37] - Scale of secondary transactions in markets today[00:10:19] - Valuations of secondary transaction rounds versus primary ones[00:11:37] - Defining great in private market investments and the competitive landscape[00:13:13] - Why there seems to be more information available in private markets[00:16:23] - How better capital allocation may result from less asymmetry[00:19:14] - What excites him about companies when meeting them for the first time[00:20:34] - Example of applying his philosophy of investing in a defensible business[00:22:20] - Counter positioning and inversion models to gain an advantage[00:24:17] - Lessons learned from Palantir about unlikely competitive advantage [00:25:57] - Building good businesses when selling them to the government[00:26:59] - What technology means in the current era[00:28:34] - Methods for evaluating potential sources of defensibility and a lack thereof[00:30:30] - Considering focus and expansion when scaling[00:32:52] - Shared qualities of entrepreneurs who build these types of businesses[00:33:50] - The business that individually taught him the most writ large[00:35:01] - Defensabilities that might appear beyond the seven powers framework[00:36:21] - Thoughts on what seems to be craziest in the world today[00:37:15] - What’s surprising on the low end of the valuation side[00:38:11] - Interesting business models and ones he’s averse to [00:40:31] - Constructing a portfolio with companies that have a customer focus[00:41:21] - Additional companies in their portfolio that aren’t of a similar model [00:42:08] - Lessons learned from SpaceX’s growth[00:44:46] - Watching a SpaceX launch in person[00:46:03] - Advice for entrepreneurs when seeking capital and capital partners[00:48:04] - Investors he finds most impressive that he knows well[00:49:26] - Defining the cost of capital and what it means to him as a venture investor[00:50:56] - Is giving entrepreneurs too much money dangerous?[00:54:14] - What great capital allocation looks like to him[00:55:29] - Accelerating learning curves with tighter feedback loops[00:55:57] - Useful metrics for customer acquisition and retention[00:57:06] - Whether or not investing firms can and should behave defensibly[00:59:13] - What is going in the world that has his attention lately[01:02:06] - Key factors that have allowed him and his firm to succeed[01:03:47] - What he thinks about when his mind isn’t focused on investing[01:04:08] - The kindest thing anyone has ever done for him 

My guest today is Peter Reinhardt, co-founder and CEO of Segment, the market-leading data customer data platform that was acquired by Twilio last year. In our conversation, we cover the fascinating journey of Segment from an education feedback tool to the business it is today, Peter’s sales philosophy on meeting the customer where they are and not where you think they should be, and why revenue operations, or RevOps, is underrated for any business. This was an incredibly honest conversation on company building that any builder can learn a lot from. Please enjoy my conversation with Peter Reinhardt. For the full show notes, transcript, and links to mentioned content, check out the episode page here.-----Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:02:47] - [First question] - What Segment currently does for its customers[00:03:37] - How this industry looked before Segment came along[00:04:30] - Overview of a simple data flow and the utility of capturing user data[00:05:55] - Insights that lead to developing the structure for a central data pipeline[00:07:52] - Why other companies don’t just build their own data collection API[00:10:04] - Early days of building the company and finding success outside their initial idea[00:12:29] - Pivoting from classroom software to providing software the world needed[00:16:17] - What Technology Wants [00:17:06] - Sign that validated becoming a B to B software company[00:19:49] - Challenging moments trying to scale Segment after bootstrapping the startup[00:24:58] - Getting customers to articulate your value proposition helps grow your sales[00:26:42] - Deciding what would be sold and what would remain open source[00:28:05] - Structuring and developing an enterprise sales team and sales model[00:30:23] - Overview of a 2 million dollar per sales person contract and how it’s allocated[00:31:38] - How it feels to be participant in the SaaS industry[00:34:02] - Lessons learned about revenue operations and how underappreciated it is[00:36:39] - Backwards efficiency and companies who use products to bootstrap scale economics[00:38:51] - Focusing on customer acquisition cost to maximize scale efficiency[00:40:52] - Potential disruptors to economies of scale[00:42:21] - Lessons learned from achieving massive scale and being acquired by Twilio[00:45:40] - Behind the curtain view of current data use trends[00:48:49] - His perspectives on the data privacy landscape and their implications writ large[00:51:48] - Legitimate businesses that will be hurt by changes in data privacy standards[00:53:11] - How data privacy standards may affect everyday merchants[00:54:03] - The worst advice he’s heard given to new entrepreneurs[00:56:20] - Impactful advice received along the way when growing Segment[00:56:47] - What has him most excited about the future[00:57:13] - Lessons learned about leadership from Jeff Lawson and his own experience[00:58:51] - The hardest changes he’s had to make as a leader[01:00:20] - The kindest thing anyone has ever done for him 

My guest today is Brent Beshore. For those that don’t know Brent from his frequent appearances on this podcast, he runs Permanent Equity Fund and has been a close personal friend for the past five years. Brent and I revisit our conversation from the heart of COVID to touch on key lessons learned and where that leaves us today. Brent sits at a unique touchpoint of the economy, so I particularly enjoyed his anecdotes on inflation and how to operate around these dynamics. I hope you enjoy my conversation with Brent.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors.   With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:52] - [First question] - Why last year ended up being so bullish [00:07:14] - Deal dynamics of the current landscape [00:09:54] - Lessons learned about managing a team through the pandemic [00:14:39] - Observations on the housing market and the pool industry [00:18:56] - Current labor force dynamics of trades  [00:21:18] - Considering labor dependency when investing in new businesses [00:23:10] - His perspectives on the future of tech through his investment lens [00:25:50] - Seeking out traditional businesses that reinvent age-old frameworks  [00:27:50] - Key stages of the art and science of evaluating and acquiring a company [00:31:45] - How much information he wants to know before making an initial offer [00:34:25] - Psychology of structuring and aligning incentives post-acquisition  [00:37:41] - What defines a great deal negotiator [00:40:05] - His most creative act when structuring a deal that didn’t work out as well [00:42:17] - Hist most creative structuring act that proved useful for the upside [00:43:34] - Notable changes in large-cap private equity markets [00:45:41] - Skills he feels he can improve on over the coming five years [00:48:30] - Coaching small companies on how to recruit top tier talent [00:52:49] - How to effectively get people to say yes to job offers and openings [00:54:19] - Absolute and relative changes in the opportunity set of small to mid-cap markets [00:57:40] - Lessons learned from strong support networks and onramps of upward mobility

My guest today is Jeremy Cai, founder, and CEO of Italic, a subscription marketplace for consumer goods that works directly with manufacturers. I was introduced to Jeremy by my friend Blake Robbins and was dying to better understand the Italic business model. In our conversation, we discuss the Italic business model, the evolving role of manufacturers in supply chains, and the concept of building the next generation “everything store.” I love learning and discovering new business models, and this was fun to dig into. Please enjoy my conversation with Jeremy Cai.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at dell.com/en-us/work/shop/deals. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:45] - [First question] - Overview of Italic’s business model [00:04:51] - Why comparing Italic to Costco isn’t completely accurate [00:10:06] - His initial experience with manufacturers and how that world works [00:15:21] - Direct to consumer commerce and the power of a brand’s story [00:20:06] - Where manufacturers find the cash to effectively manage their inventory [00:25:26] - How design and R & D are handled by manufacturers in the current era [00:29:36] - Educated consumers and emotional versus rational buying decisions  [00:31:12] - Analyzing Italic’s five-step master plan and what needed to be built first [00:35:42] - Becoming more than just an aggregator and a platform [00:38:01] - Lessons learned from building Italic so far [00:39:02] - Other modern business models he finds interesting [00:43:26] - What Not Pot is and lessons learned from building it [00:44:51] - Observations about consumer behavior in his managed marketplace [00:48:07] - The kindest thing anyone has ever done for him

My guest today is Eli Dourado, economist and senior research fellow at the Center for Growth and Opportunity at Utah State University. In our discussion, we touch on the ongoing stagnation in labor productivity, the system constraints, and some of the innovative technologies that could reverse this trend. While Eli identifies as an economist, his wealth of knowledge on biotech innovation, alternative energy, and the space opportunity are sure to leave you craving more. I hope you enjoy my conversation with Eli.  For the full show notes, transcript, and links to mentioned content, check out the episode page here.------Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:03:28] - [First question] - Why he’s interested the great stagnation[00:05:41] - Is a fair analog for total factor productivity technology?[00:07:29] - Leading theories for the stagnation in TFP[00:09:05] - Analysis of why growth is good, and stagnation is bad[00:10:19] - Rate limiters that are a key part of calculating stagnation[00:11:43] - Signs that we may be returning to a higher degree of TFP returning[00:12:24] - Exciting developments like MRNA in biotech that may lead to an explosion of innovation[00:16:16] - Functions of a protein and their role in advances in biotech[00:17:55] - What CRISPR is and what it unlocks for the future of humanity[00:19:31] - The pace of progression when rolling our clinical trials of cellular engineering[00:21:36] - How biotech may play a role in TFP as a proxy for progress and growth[00:22:51] - Interesting observations about potential innovation in the energy sector[00:24:10] - What currently requires energy that could be optimized if they had a lower energy cost[00:25:34] - Sources that could provide cheaper and more efficient energy[00:27:13] - Sage Geosystems and the future of the geothermal space[00:27:43] - The importance of batteries in the modern era[00:29:02] - Why energy should be a more pivotal focus in our future[00:29:41] - What’s interesting in the world of transportation writ large[00:31:02] - Boom’s story, supersonic air travel, and why concord shut down[00:34:55] - Mach 5 and March 12 supersonic air travel[00:36:19] - Second-order effects of reducing the time cost of air travel[00:38:19] - Liftoff, SpaceX, and the future of the space sector[00:43:07] - Other key players in space people could study; Blue Origin and Relativity Space[00:45:15] - What will we do in space once we can travel there cheaply[00:46:39] - What he’s most curious about in IT that could drive productive societal growth[00:50:07] - Ethereum and how a decentralized blockchain could change the world [00:51:19] - The kindest thing anyone has ever done for him

My guest today is James Reinhart, founder, and CEO of thredUP, an online thrift marketplace. thredUP’s online store is distinct in the way the company touches every product, processing every piece of clothing at their own facilities instead of focusing solely on being a marketplace connecting buyers and sellers. We talk about the competitive advantages of building processing plants from the ground up, how James turned thredUP from having negative gross margins to very strong unit economics, and the future of retail more broadly. I hope you enjoy this conversation with James Reinhart.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at dell.com/en-us/work/shop/deals. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." -----   Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:47] - [First question] - An overview of thredUP [00:03:44] - Origination of the idea [00:04:43] - Initial reactions to the concept [00:05:22] - Early days trying to acquire the first customers [00:07:32] - The evolution of their margins [00:11:04] - Providing convenience for the customer [00:13:01] - Lessons on working capital and inventory  [00:14:27] - How consumers use the money they receive within the platform [00:15:47] - The evolution of the operations of the business and scaling [00:20:20] - When it’s time to shift from human capital to automation [00:22:00] - The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time [00:22:39] - Competitive Advantage: Creating and Sustaining Superior Performance [00:23:15] - Removing the hurdles for acquiring more buyers  [00:27:19] - Convincing investors on this concept [00:30:44] - The most difficult time for him psychologically in creating the business [00:31:56] - How he thinks about capital allocation [00:32:12] - The Startup Way: How Modern Companies Use Entrepreneurial Management to Transform Culture and Drive Long-Term Growth [00:33:51] - Overview of the clothing landscape and what would surprise most people [00:38:00] - Expanding their business from here  [00:40:36] - Improving how the raw material is sourced for apparel [00:42:45] - The nature of work  [00:42:56] - Dustin Moskovitz Podcast Episode [00:49:04] - What he’s most excited about for the future [00:50:35] - Kindest thing anyone has done for him

My guest today is Andrew Sugrue, co-founder, and partner at Avenir Growth Capital. Avenir is a growth equity firm focused on backing category-defining businesses. In our conversation, we cover Andrew’s investing career, what he learned from Julian Robertson, how counter-positioning could drive unique distribution, and the difference between good and bad growth. We also spend time examining the business model of two of Andrew’s portfolio businesses, SavageXFenty and Latch. There are so many great lessons for investors and operators to take away from Andrew. Please enjoy my conversation with Andrew Sugrue.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by MIT Investment Management Company – MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term.    MITIMCo is also searching for an exceptional new teammate to join their internal investment team. Visit mitimco.org to learn more – click “Join” to learn more about the Global Investor Role on MITIMCo’s team or and click “Emerging Managers” to learn more about their emerging manager activities. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:31] - [First question] - His journey leading up to his current firm [00:05:55] - Lessons learned from time spent with Julian Robinson [00:07:54] - The chip on his shoulder that helped keep him driven [00:08:40] - Transforming his early motivators into a sustainable career-long fuel [00:10:46] - The first things in mind when approaching a new business or person [00:14:00] - Analysis of Savage Lingerie and learning about how that sector operates  [00:20:27] - Amazon producing a one-hour special Savage infomercial  [00:23:16] - Lessons learned from Savage that can be applied to other direct to consumer brands [00:25:04] - Having a celebrity at the forefront of your brand [00:26:41] - Levers and overview of apparel company income statements and how they can shape the way you grow and operate the business [00:30:08] - Apparel companies always being tied to identity [00:31:03] - Analysis of Latch and learning about the relationship between hardware and software [00:33:40] - How Latch works and why you might need it [00:38:56] - Other businesses that may benefit from understanding the events that drive demand and using it as an opportunity for customer acquisition [00:40:12] - The concept of density of demand and the power behind it [00:41:33] - Other areas of operations density of demand could be applied  [00:44:11] - Shared components that unite Avenir’s portfolio companies  [00:46:14] - How he thinks about the world of private investment, having lived such a diverse career  [00:50:22] - Developing relationships growing such a concentrated portfolio [00:51:35] - Macro thoughts on the state of investing today [00:52:59] - Defining and identifying characteristics of bad growth [00:54:05] - The kindest thing anyone has ever done for him

My guest today is Alyssa Ravasio, co-founder and CEO of Hipcamp, a platform to discover and book your next camping trip. I was excited for this conversation as it combines two of my favorite passions – the outdoors and internet marketplaces. In our discussion, we cover how Alyssa bootstrapped demand in the early days of Hipcamp, the importance of creating not just great experiences but magical ones, and the evolution of Hipcamp’s business model. After listening to this episode, I’m sure the first thing you’ll want to do is get outside in nature. Please enjoy my conversation with Alyssa Ravasio.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick.   ----- This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers.   If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:57] - [First question] - The original insight that led to founding Hipcamp [00:06:15] - What she studied in college and primary lessons learned there [00:08:18] - Specific features of studying the internet that influenced her trajectory [00:10:14] - Deciding what to attack first when developing Hipcamp’s infrastructure [00:14:12] - Dimensions and market size of the outdoor industry [00:15:48] - Organizing fragmented data into a useable schema and data set [00:18:24] - What customers cared about most in the early days of Hipcamp [00:20:00] - Managing focus and liquidity of the initial marketplace [00:22:58] - Helping landowners manage the logistics of their property placements [00:25:16] - Liability insurance in the outdoor industry [00:27:35] - The biggest challenge faced in developing an outdoor marketplace [00:30:03] - Amplifying and accelerating naturally grooved distribution [00:32:32] - Identifying the top correlates of making magic happen [00:34:55] - An ideal future for Hipcamp five years from now [00:38:28] - What bad supply looks like and creating quality standards  [00:42:08] - Their business model and revenue stream [00:44:45] - Deciding on their take rate and the debate around booking fees [00:46:14] - Lessons learned along the way as a leader [00:47:42] - Unit economics from the host’s perspective [00:52:33] - The most interesting businesses built on top of Hipcamp [00:53:35] - Why is Hipcamp’s mission so important to her [00:57:11] - The kindest thing anyone has ever done for her

My guest today is Josh Buckley. Josh is the new CEO of Product Hunt and an investor in many breakout companies like Rippling, Lattice, Boom Supersonic, and Relativity Space. In our conversation, we cover how video game companies are at the forefront of new business models, what current companies can learn from video game companies, Josh’s investing philosophy, and the three things he looks for when trying to identify the next legendary startup. Josh’s long experience operating his video game business, Mino Games, gives him such an interesting perspective as an investor, and I really enjoyed exploring that with him. Please enjoy my conversation with Josh Buckley. For the full show notes, transcript, and links to mentioned content, check out the episode page here.------Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:03:56] - [First question] - His start as an entrepreneur in online game[00:05:09] - His parent's reaction to selling his first company at fifteen[00:05:57] - Starting a second video game company [00:07:40] - The video game industry being ahead of the curve in performance marketing, distribution, and operations[00:08:49] - Notable two year lag between gaming innovation and other consumer sectors[00:10:50] - What is happening today in gaming that may be a glimpse into the future[00:12:41] - Key elements for creating a great gaming experience[00:15:29] - Building a meta game on top of the game itself to maximize engagement[00:17:23] - Monetizing free to play games through in-game purchases[00:20:25] - The most portable idea from fifteen years in gaming that can be applied to business[00:22:02] - A future shift towards usage-based pricing models[00:23:03] - His overall investment philosophy and strategy[00:26:45] - Example of small a market with a high growth rate[00:27:38] - Key elements of system elements and design when evaluating a business[00:31:07] - What a flywheel looks like and investing in one such as Next Health [00:33:24] - Working core actions versus giving credit ones that aren’t yet working but may drive desirable outcomes[00:34:13] - Why don’t more investing firms have a flywheel?[00:39:04] - Product Hunt as a standalone business and part of a self-reinforcing ecosystem[00:40:17] - Emerging systems and ecosystem edges in the digital landscape[00:42:17] - Potential barriers for crypto becoming widely adopted in a variety of ways[00:44:29] - New frontiers and platform shifts like crypto that may unlock new doors for companies[00:45:13] - Which person has rewired his brain in his lifetime the most[00:47:13] - Weirdness around Stripe and Plaid when he first encountered them[00:48:37] - Meta games people in the industry are playing or should be playing[00:51:25] - Controversial ideas around the business world today writ large [00:54:01] - Implications of shifting primarily towards a digital world[00:54:14] - The kindest thing anyone has ever done for him