My guest today is Frank Slootman, Chairman and CEO of cloud platform Snowflake. Frank has become one of the most revered CEOs in business. Over the past twenty years, he has three times taken over emerging enterprise software businesses – first Data Domain, then ServiceNow, and most recently Snowflake - and led them across the chasm into large, billion-dollar businesses. Please enjoy this great discussion with Frank Slootman.   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   -----   This episode is brought to you by Tegus. Tegus is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best in class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial.   -----   This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. -----   Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   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 [00:02:33] - [First question] - How he evaluates the team of a company he’s working with [00:04:48] - The pace of decisions made around changing team members  [00:06:10] - Understanding the potential quality of outside leaders being brought into the company [00:08:13] - How he characterizes great and constructive confrontation [00:09:53] - What he’s found to be most effective in convincing senior talent to join a team [00:11:36] - Ways he personally generates energy to sustain himself in this pace of business [00:14:17] - How he fosters and nurtures healthy communication pathways [00:15:36] - Narrowing the focus when evaluating a new product [00:17:58] - Is it possible for a focus to be too narrow? [00:19:31] - An example of a dazzling customer that he’s worked with  [00:21:04] - Working backwards from a problem and building something that solves it [00:23:03] - Building trust between a company and its customers over time [00:25:37] - Overview of the base layer ingredients of trust [00:28:12] - Sequential versus parallel processing and how they affect building trust [00:30:22] - Lessons in successfully translating between engineers and business people [00:32:58] - Crossing the chasm and effective sales organizations [00:35:17] - Working compensation into getting more out of an organization [00:38:45] - How much a sales organization needs to work backwards to serve their product [00:41:40] - Great questions for board members to ask their executive team [00:46:07] - Where the analogy of ‘business as war’ falls down and defining the highlander concept  [00:48:01] - What he feels he could still hone in his skillset  [00:49:16] - The kindest thing anyone has ever done for him 

My guest today is Tim Flannery, co-founder of venture fund administrator Passthrough. Passthrough is removing friction from the manual, time-consuming fundraising process by making investor onboarding as simple and automatic as possible. Their software helps investors fill out subscription documents in minutes rather than hours and allows GPs to easily track LP subscriptions during a fundraise.   In our conversation, we discuss the power of identity as a feature to build products around, the double-edged sword of solving an unsexy problem, and how Passthrough has thought about pricing their software. Please enjoy my conversation with Tim Flannery.   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   -----   This episode is brought to you by Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs so you can focus on what matters most — building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders.    -----   Founder's Field Guide is a property of Colossus, LLC. 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 [00:02:08] - [First question] - The push and pull nature of what Passthrough is trying to solve [00:04:17] - What the idealized end state 10 years from now looks like [00:07:33] - A history of friction in investing and what barriers still remain today [00:12:35] - The spark of insight that led to starting this new venture [00:17:45] - Lessons learned from Okta and why identity is so powerful [00:19:39] - Plans to expand this concept deeper into the tech stack [00:22:24] - Adjacent problems that they plan to tackle as they continue to scale [00:24:30] - What it feels like to use their product as an LP today [00:26:10] - Working with service providers without becoming one [00:28:06] - What great sales and distribution looks like to him at the infrastructure level  [00:31:50] - Defining what “bring your collaborators” means  [00:33:19] - His secret to recruiting talent to help solve an unsexy problem [00:37:46] - His love for the intersection between process, pipelines, and efficiency  [00:40:12] - Having a process for designing processes [00:42:11] - How they arrived at their pricing and thoughtful pricing in software [00:45:08] - Lessons from building Passthrough that other builders could benefit from  [00:47:16] - The kindest thing anyone has ever done for him

My guest today is IAC’s CEO, Joey Levin. IAC is a unique business in that it’s a holding company which builds world-class digital businesses. Since Barry Diller created IAC over two decades ago, it has produced 11 public companies, including Match Group, Expedia, and Live Nation. Today, the business is comprised of category-leaders like Angi, Dotdash Meredith, and Care.com. Joey joined IAC in 2003 and became CEO in 2015. We talk about why he tries to avoid centralization between businesses, what he's learned from Barry Diller, how he approaches capital allocation, and so much more. This conversation serves as an excellent reminder that there’s no formula to company building. Everything is idiosyncratic and requires its own best decisions. Please enjoy this great discussion with Joey Levin. 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, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. 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[00:03:05] - [First question] - The unique nature of IAC; the business of building businesses[00:05:27] - The first business spun out of IAC and its bottom-up philosophy[00:06:41] - The differences of IAC and how they manifest [00:09:39] - Agility and history of respecting the core functions of the internet[00:12:36] - Simplified, faster, and larger choice digital experiences[00:15:57] - His thoughts on the shared characteristics amongst their winners [00:18:26] - Lessons from building competitive products in online dating simultaneously[00:21:37] - Navigating customer acquisition cost and embracing change[00:24:04] - What makes someone great at customer acquisition [00:26:26] - Fostering a unique approach compared to typical customer funnels[00:27:48] - What most explains his move from a pip-squeak to CEO[00:29:44] - The process he uses to get to know the critical aspects of a new business[00:31:59] - Indications that a leader may no longer be suited to run a business[00:33:13] - Characteristics of vertical markets that he finds attractive to get involved in[00:34:08] - The early stages of incubating a new business and an overview of their process[00:38:10] - Enabling new consumer experiences and infrastructure fading away[00:40:17] - Distilling big ideas down to streamlined approachable consumer products [00:42:22] - High-level internal conversations around capital allocation[00:45:06] - Quantitative versus qualitative analysis in their decision-making process[00:46:50] - What idea felt the most right but turned out to be a disaster[00:51:26] - Brand rollup versus brand consolidation and when either strategy is appropriate[00:54:03] - Having a good sense of identifying, defining, and positioning categories[00:56:23] - Which aspects of his perspectives have shifted since becoming CEO[00:57:59] - Thoughts on the toolkit available for sourcing and the cost of capital[01:01:08] - What personally brings him the most joy in what he does[01:02:37] - Working with Barry Diller and what it taught him[01:06:39] - The kindest thing anyone has ever done for him

My guest today is Peter Chernin, who’s had a Hall of Fame career in the entertainment business. Peter ran News Corp and Fox for fifteen years between 1996 and 2009 before co-founding The Chernin Group, which has become one of the leading investment firms in the consumer space. Along the way, he has also produced a number of blockbuster films, including Titanic, Avatar, The Greatest Showman, and The Planet of the Apes Trilogy. Please enjoy this wonderful discussion with Peter Chernin.   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   -----   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 20,000 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.   -----   This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've ever used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening in our bodies. And it was the only product that ever made me willing to log food. If you want early access to become a Member of their private Beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK   -----   Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   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 [00:03:06] - [First question] - Business and investing lessons from producing Titanic and Avatar [00:06:44] - Defining great content and why James Cameron’s franchises have done so well [00:10:26] - Contributing factors to box-office domination of pre-existing franchises [00:12:56] - Tailwinds in his earlier career and identifying them in time to get behind change [00:16:07] - Identifying Showcase was a subscription business early on, unlike broadcast businesses [00:19:40] - Signals of passion and how powerful niche audiences can be  [00:23:24] - What a phony aggregator is and the slow dissolution of the middle market [00:27:01] - The era of unbundling and direct relationships with superfans [00:30:27] - Lessons learned from building Hulu [00:34:29] - Working with Rupert Murdoch and qualities that separate him from the crowd [00:37:07] - Defining what bravery means in a businesses sense [00:39:22] - A movie he’s made in the past decade that he’s most proud of [00:43:27] - The keys to being an effective partner to creative individuals [00:49:53] - What exists today that may change the future landscape of media writ large [00:52:19] - The kindest thing anyone has ever done for him

My guest today is entrepreneur and investor, John Pfeffer. John was a partner at private equity firm KKR in the 2000s, Chairman of leading French IT company Groupe Allium in the 90s, and now invests his own money through his private family office, Pfeffer Capital. John is one of the smartest investors I know, and our conversation spans all of John’s experience and investment ideas. We discuss the difference between value creation and wealth creation, why John has made such a big bet on one asset, and why adaptation is more important than ever. I hope you enjoy this conversation as much as I did.   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   -----   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 20,000 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.   -----   This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.   -----   Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   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 [00:03:08] - [First question] - John’s background and the experiences that shaped his worldview and sparked his curiosity [00:07:34] - Aspiring to grow with a lack of inertia  [00:10:31] - Why he invests primarily in technology and technology dependant businesses [00:15:22] - What it’s felt like being a tech investor from 2011 leading up to today [00:19:26] - How he defines good and bad business [00:21:24] - Why good businesses don’t often have technology disruption risks [00:22:26] - An (Institutional) Investor’s Take on Cryptoassets; key points from his paper [00:35:28] - What else is interesting in the crypto space and potentially strong business models that exist outside of Bitcoin  [00:48:46] - How capital has changed over time and what makes capital efficiency or formation superior [00:51:51] - Value creation and why a shift in value can affect your returns [01:01:12] - Whether or not crypto and the founding protocols will fade out of the public eye [01:11:52] - A consensus on store of value in crypto and how it could change [01:18:03] - Why he is so heavily allocated to Bitcoin compared to other tokens [01:25:19] - General take on the nature of buying and selling capital and European markets [01:35:28] - The interconnectedness of the globe and the future of globalism [01:39:46] - Why he doesn’t ask people where they’re from and how he prefers to get to know people that can sometimes be unorthodox [01:41:59] - Market index investing and why it may not be the best strategy going forward [01:47:36] - The kindest thing anyone has ever done for him

My guest today is the renowned tech author, consultant, and venture partner at Wildcat Ventures, Geoffrey Moore. Geoffrey has spent his career focused on the dynamics surrounding disruptive innovations and his book, Crossing the Chasm, has become a canonical work for young businesses trying to unlock mainstream markets. This discussion is a masterclass on business strategy. We start with Geoffrey’s more recent work on category-defining businesses, break down his life cycle of adoption framework, and close with the ways messaging should change as a company evolves. Please enjoy this great discussion with Geoffrey Moore. 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, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. 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[00:03:08] - [First question] - What he means by a gorilla business[00:07:10] - An example of how companies self-organize into gorillas, chimps, and monkeys[00:09:41] - Why architecture is so important and how it applies to company building [00:13:11] - How and when businesses should think about open and closed systems[00:14:50] - Ways in which enabling tech companies are superior to application ones[00:16:39] - Thoughts on approaching and hiring a singular use case company [00:18:23] - Markets underestimate competitive advantage periods for technological gorillas[00:20:38] - The inertia and duration of being the creator of a space’s architecture[00:23:28] - Advice for early-stage companies when creating or dominating categories [00:25:16] - What he’s learned about identifying trapped value [00:26:49] - Questions that can identify trapped value, factoring for time, and horizontal uses[00:41:49] - Problems with risk exposure in B2B and applying this model for value creation[00:33:37] - His initial discovery of the life cycles of adoption and its five categories[00:39:29] - Perspective on venture capital funding and going from idea to the chasm[00:44:10] - What good pragmatists in pain look like [00:47:29] - Successful vertical uses-case sales motions[00:50:03] - Guarding from becoming over-specialized in a singular focused effort[00:50:52] - The Diffusion of Innovations; Ways messages work their way through a company to keep up with category evolution [00:55:00] - How extensible these ideas are to non-technology businesses[00:56:04] - The race between innovation and distribution [00:56:44] - What about the world today has changed or influenced his thinking[00:59:17] - Ways big companies can stay competitive in emerging categories[01:02:23] - The company he’s most enjoyed studying over his career [01:05:25] - Shared characteristics of exceptional leaders he’s met and talked to[01:07:48] - The Gorilla Game, Crossing the Chasm[01:08:14] - The kindest thing that anyone has ever done for him

My guest today is past guest Gavin Baker, managing partner and CIO of Atreides Management. Gavin’s focus is on consumer and tech growth investing, which makes him the perfect person to discuss the bloodbath we’ve seen in many growth equities over the past few months. We also cover inflation, semiconductors, and the disconnect between private and public markets. Please enjoy this conversation with the always great Gavin Baker.   For the full show notes, transcript, and links to the best content to learn more, 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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.   -----   This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.   -----   Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   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 [00:02:30] - [First question] - What it’s been like investing over the pandemic  [00:06:14] - The way he thinks about multiples, how they’ve done, and where they’re going [00:09:14] - Themes that most have his attention in our current economic landscape [00:19:25] - The ways in which wage inflation negatively impacts the market [00:25:39] - How semiconductors have evolved and what matters in that subsector [00:32:47] - Software volatility and the roller coaster it's been on lately [00:35:52] - A future state where infrastructure overtakes apps  [00:41:03] - Key differences between internet and software and how they behave [00:43:44] - The coming trend of the metaverse and his reaction to public adoption [00:49:26] - Investor and business opportunities in adopting tech trends [00:53:54] - An unfolding mismatch between private and public market multiples [00:57:17] - How the competitive landscape of venture capital might evolve [01:05:54] - Differences in recruiting and training talent in private and public markets [01:10:20] - Sci-Fi novels that he’s read recently; Dune, A Wizard of Earthsea, Culture, Hyperion 

Today, my guests are Sam Englebardt and Richard Kim, general partners at venture fund, Galaxy Interactive. Having come from the media and finance sectors, respectively, Sam and Richard joined forces in 2018 to invest in their shared thesis that immersive digital experiences would become the dominant way people engage with each other in the future.   Our conversation centers around the evolution of art, finance, and gaming as they proliferate in Web3. Please enjoy my conversation with Sam and Richard.     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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.   -----   This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've ever used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. If you want early access to become a Member of their private Beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK   ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   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 [00:02:50] - [First question] - Their thoughts on the digital art market [00:11:33] - What motivates traditional art collectors and what has been carried over into digital art [00:17:27] - Is there an attractive beta opportunity in the digital art space? [00:24:32] - Why investors should do more work understanding NFTs and ways to consider incorporating them into your portfolio [00:27:55] - The history of Galaxy and their thesis writ large  [00:33:09] - Exciting and terrifying aspects of the financialization of everything [00:37:27] - Places where inserting markets could be beneficial with Web3 [00:45:27] - Their perspectives on gaming as a subcategory of Web3 [00:51:38] - Tokenomics and the importance of building great game communities [00:59:18] - What we can learn from successful gaming companies and in-game monetization [01:04:19] - How Diablo 3’s auction house detracted from the core player experience [01:06:36] - Where they disagree with the Web3 investing community [01:10:37] - The kindest things anyone has ever done for them

My guest today is Ricky Sandler, founder of Eminence Capital. Ricky is a hedge fund veteran managing over $8bn of assets across Eminence's strategies. We cover Ricky's evolution as an active investor, why he thinks this is a stock-picker's environment, and what keeps him competitive after a long and successful career. Please enjoy my conversation with Ricky Sandler.   For the full show notes, transcript, and links to the best content to learn more, 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're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.   -----   This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening in our bodies - and it was the only product that has ever made me willing to log food. If you want early access to become a member of their private beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK   -----   Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   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 [00:02:42] - [First question] Whether or not great investment firms should be led by a single investor [00:03:25] - Episodes where singular investment power has proven effective and powerful [00:05:06] - Where he finds joy in the investing process on a regular basis [00:06:19] - Ways he’s learned to become better at guiding and helping teams he works with [00:08:14] - The most common types of fool's gold he comes across [00:11:00] - Evolution of the pricing mechanisms in ever-evolving markets [00:16:14] - Common features of a good mispricing opportunity [00:18:42] - How he interacts with other hedge funds and long-only investors [00:21:14] - An investor he often disagrees with but loves talking to  [00:22:13] - The investment he’s most proud of historically [00:25:11] - What the healthy draw that keeps him coming back to investing is [00:28:31] - His opinion on crossover funds and their growing popularity [00:32:09] - What the world in 2022 looks like to him and what both excites and worries him [00:38:19] - Key contributors that influence liquidity and how it flows into equity prices [00:41:26] - A macro view of the healthcare sector and why it’s so interesting today [00:42:59] - Lessons from the Titans [00:43:52] - Advice he’d give to younger investors for stepping into the space  [00:46:45] - The kindest thing anyone has ever done for him

My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this excellent discussion with Orlando Bravo.   For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.   -----   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 20,000 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, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   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 [00:02:36] - [First question] - His belief about an opportunity/capital mismatch in private equity [00:04:26] - Adjusting his own approach to take advantage of seemingly niche opportunities [00:06:13] - Differences between software businesses they invest in versus traditional ones [00:08:25] - Outline of how he runs their four-hour portfolio meetings [00:09:53] - Overview of the very first deal he ever made in the software sector [00:14:01] - The dissonance between the average SaaS company and the ones they try to manage [00:18:22] - Major contributors that allow for their higher margins [00:20:16] - Common mistakes of companies that mis-invest capital for growth only [00:22:28] - Defining what market leader means writ large [00:23:45] - Why the subsector of cyber security is such a good opportunity set [00:26:25] - The evolving nature of the private equity world in general [00:28:41] - Where returns will come from going forward [00:31:47] - How good the opportunity for returns in this style of investing today is [00:35:32] - Lessons learned on knowing when to exit or sell a position [00:37:59] - How short their holding periods can be and how much influence they can have in such a short time [00:40:04] - Surprising things about deal-making that he’s learned over his career [00:41:20] - Difficulties and points of frictions in deals that still exist for him today [00:43:11] - What part of the deal-making process he loves the most [00:44:30] - If your job title has a C in it you’re not allowed to complain about it [00:46:27] - Deeply held beliefs about operating excellence [00:47:33] - What the word service means to him given everything we’ve talked about  [00:50:27] - How we do a better job of inviting talent into this space [00:52:51] - How decentralization will define the 2020s and beyond [00:55:48] - What is most interesting about Web3 that might affect cyber security [00:57:42] - Where there is a lack in innovation in private equity today [01:00:45] - Advice for young talent for building their careers [01:03:16] - The kindest thing that anyone has ever done for him