Avi Goldfarb, a Professor at the University of Toronto and an expert in AI, discusses the economic impact of AI and how it may reshape business models and systems. Topics include the impact of AI on writing skills and job opportunities, the historical adoption of transformative technologies like electricity, transitioning from rules to decisions with AI, the failure of companies like Blockbuster to adapt to new business models, the unpredicted impact of AI on job sectors, the effects of technology on various professions, and the value of reading specific books for business insights.

My guest this week is Auren Hoffman. Auren is the CEO of Safegraph, which curates data on physical locations. He also founded LiveRamp, a public data connectivity business. Auren knows more about data businesses than almost anyone I know and that is the topic of today’s discussion. We look at the business of data from every angle and finish with a fun masterclass on how to host a dinner party. Please enjoy my conversation with Auren Hoffman. 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, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. 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[00:03:16] - [First question] - His 2x2 matrix for categorizing different types of data businesses[00:04:59] - An example of what he calls a religion company in his matrix[00:07:03] - His notion of data currency[00:08:23] - His definition of a great business[00:09:46] - An example of a so-called application religion company in his proverbial matrix[00:11:24] - Co-op and non-profit business models within and outside of the data sphere[00:13:35] - The truth application quadrant of his matrix[00:16:18] - How data has exploded in prevalence for the business world as a whole[00:18:57] - How to think about the end market for data and its demand[00:21:09] - Characteristics of a good data set and how to identify it[00:23:14] - Other factors that impact the usability of a data set[00:24:30] - Optimizing data collection itself[00:26:30] - The slow growth that’s typical of early-stage data companies[00:27:27] - Market share considerations for data businesses[00:30:03] - Common struggles for data entrepreneurs[00:34:01] - The genesis of his business; SafeGraph[00:37:08] - The power of self-maintained and user-maintained databases[00:40:16] - Typical customers and use cases for SafeGraph’s data[00:41:08] - How SafeGraph and other companies protect against data theft[00:42:12] - Frequency of change as a proxy for the value of a given data set[00:45:32] - Categorizing inbound data based on the most important criteria[00:47:07] - The founder personalities he finds in the data industry[00:49:53] - Why he feels the data truth quadrant of his matrix is underdeveloped[00:50:30] - Bloomberg as an important data company to study[00:51:42] - The importance of transparency in business and in data distribution[00:53:07] - Failure modes that he sees most commonly in data-based startups[00:53:53] - Data businesses becoming application businesses and vice-versa[00:57:35] - The great dinner parties he’s known for[00:59:50] - How he makes the dinner parties appeal to introverts[01:03:11] - Dead people he would most like to have as dinner guests[01:04:09] - Questions he would ask the most influential religious figures[01:06:20] - The kindest thing anyone has ever done for him

My guest this week is Trae Stephens. Trae is a partner at Founders Fund and co-founder and Executive Chairman of Anduril. Trae’s philosophy can be boiled down to finding good quests, which has led him to investing in businesses that work closely with the government on societally important issues. Clearly, that extends to co-founding Anduril and I would highly recommend listening to my Business Breakdowns episode on Anduril if you haven’t already. In this conversation, we discuss the importance of lobbyists, why the high-tech defense firms of the past became stale, and how he hunts for disagreeableness in founders. Please enjoy my conversation with Trae Stephens. For the full show notes, transcript, and links to mentioned content, check out the episode page here. Listen to Founders PodcastFounders Episode 136 - Estee LauderFounders Episode 288 - Ralph Lauren ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. 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[00:03:17] - [First question] - Why Trae thinks most high-margin businesses are bad for society[00:04:28] - What would he change to impact energy technology most if he were in charge[00:06:18] - His investing focus on dynamism and mission-driven tech companies[00:09:42] - Analyzing why relatively few people strive to make society-level advancements[00:11:35] - What he’s done as a parent to enable his kids to develop passions[00:12:41] - The most noteworthy adventures in his career[00:14:41] - Founding Anduril and what it taught him about the tech industry[00:18:40] - The cutting-edge of defense technologies today[00:21:29] - What Shyam Sankar of Palantir taught him about defense tech[00:23:34] - Why some of the biggest defense tech companies have stopped innovating[00:28:29] - What he and Anduril have learned about sales and scaling in the public sector[00:35:22] - His take on Peter Thiel’s notion that competition should be avoided[00:38:24] - The importance of being psychologically disagreeable when building a start-up[00:39:54] - The origin story that stands out the most from companies he has interviewed[00:41:12] - How he developed an investor mindset on his unorthodox path to the venture world[00:43:57] - What he has learned from playing supporting roles and aligning with great leaders[00:46:11] - Important but uncommon lessons about entrepreneurship[00:48:21] - Venture investing lessons he’s learned from Lauren Gross[00:50:00] - His first VR project and aspirations for the future of VR[00:54:50] - The role of religion and spirituality in his business philosophies[00:59:13] - Why he tries to capitalize on morality as opposed to sin[01:03:57] - The kindest thing anyone has ever done for him

Doug Leone, former head of Sequoia, shares his experiences in leading the firm's expansion. He discusses go-to-market motions, advice for investors, and the importance of keeping things simple and clear. Other topics include the evolution of the venture capital industry, common failure modes of investors, and acts of kindness and support.

I’m excited to share this conversation with Tim Urban. Tim is, in my opinion, one of the best and most engaging writers of our era. He’s tackled many of the most interesting topics in the world from AI to procrastination. I interviewed him in 2017 in an episode we called “Grand Theft Life”, and it remains one of my favorite episodes ever.   In the 6 years since that episode, he hasn’t published almost anything. That’s because he’s been writing the book we discuss in this episode. The book is called “What’s Our Problem”, in which Tim investigates the big issues facing society.   The reason I love Tim’s writing so much is its density of ideas and ridiculously clear explanations: a rare combo that makes reading a joy. I hope you enjoy this great round two with Tim Urban, and go buy and enjoy his great new book.   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   Listen to Founders podcast.   -----   This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/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] - What it’s been like spending seven years thinking about a single topic: Tim's book, What’s Our Problem? [00:05:05] - How he’s come to articulate the big question he’s trying to answer in his book [00:07:58] - A dinner experience where a single question showed just how much of a problem there was to solve [00:09:47] - Group ideology and the different ladder rungs of human thinking  [00:17:28] - The concept of a social golems and genies and their implications for society  [00:23:02] - His favorite genies and golems throughout history and their impact   [00:29:07] - Examples of canonical high functioning genies across history    [00:34:20] - The key ingredients within liberal democracies that allow for and correct golems [00:40:44] - Media’s role in shaping ideas and society and what’s changed about it in today’s media landscape  [00:46:46] - What else is going on that has him worried about modern institutions that are failing as social immune systems [01:01:15] - The gap between what we say publicly versus what we feel privately and the growing pile of unsaid things  [01:07:18] - What’s to be done in order to help society repair itself  [01:14:09] - Whether or not the direction we’re most afraid to run is where we should  [01:17:37] - Thoughts on AI having written extensively on it and the new wave of emerging tools [01:22:13] - The role and impact of leadership in regards to golems and genies 

My guest today is Dan Rose. Dan is the chairman of Coatue Ventures and has one of the most interesting collections of experiences of anyone I’ve talked to. He spent 20 years at Amazon and Facebook in their early days, working closely with Jeff Bezos, Andy Jassy, Mark Zuckerberg, and Sheryl Sandberg. He’s had a front-row seat to the defining products and founders of our era and his lessons from those experiences do not disappoint. Please enjoy this great discussion with Dan Rose. 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, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. 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[00:03:27] - [First question] - The story behind Amazon’s Kindle and the lessons it taught him[00:09:19] - Amazon’s philosophy of working backwards and the most creative solutions he and his team had to come up inside of that framework [00:13:04] - What he did to convince publishers to get on board with his vision [00:16:02] - His overall experience of the relationship between innovation and constraints[00:18:43] - Thoughts about the fine line between genius and nutcase [00:22:02] - What the key points of his theory on partnerships would be [00:24:28] - When advising portfolio companies becomes relevant [00:26:09] - The dark arts of building companies that could be adopted by partnerships [00:28:40] - Why he thinks the best technology companies drive strategy through product [00:32:23] - Resolving micro management while also giving skilled talent their own space[00:36:07] - Where Javier Olivan fits into his ideal executive team [00:36:57] - What about growth requires its own expertise [00:37:35] - What makes Dave Schneider an ideal sales leader[00:39:08] - The most stressful period of time while working at Facebook[00:42:51] - General thoughts on great versus good business models in tech [00:45:36] - Topics where Jeff Bezos and Mark Zuckerberg would disagree the most [00:47:13] - Defining the platonic ideal of a great investor approaching corporate enterprises [00:50:25] - Overview of the investing environment we’re in today from coast to coast[00:55:07] - What made Sheryl Sandberg so successful; Lean In[01:00:35] - Why he started his career at Life Mastery selling personal growth seminars [01:05:47] - What will define the next generation of leaders [01:07:59] - A product he would build if he could that doesn’t exist yet[01:08:59] - The kindest thing anyone has ever done for him 

My guest today is Jeff Green, the CEO and co-founder of advertising platform, The Trade Desk. The Trade Desk is the second advertising exchange Jeff has built, having sold his first venue to Microsoft in 2007. He started The Trade Desk in 2009 and has built it into a $30 billion public business. In our discussion, we talk about the parallels between The Trade Desk and an equity exchange, why Jeff chose to align with ad buyers not sellers, and how he shapes the culture of his firm. Please enjoy my conversation with Jeff Green. For the full show notes, transcript, and links to mentioned content, check out the episode page here. Listen to Founders podcast Founders Episode #136 A Success Story: Estee Lauder  Founders Episode #288 Ralph LaurenInvest Like the Best with David Senra: Passion & Pain ----- This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. 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[00:03:09] - [First question] - What he’s learned about human behavior and how it’s impacted his business[00:05:45] - Big differences in generational and perennial behavior [00:06:56] - The strong link between vulnerability and creativity  [00:07:42] - The necessary preconditions that allowed him to build Trade Desk the way he did[00:10:53] - What it would have felt like as an early stage employee at Trade Desk [00:12:43] - The hardest parts about maintaining his type of company culture[00:14:05] - How much of his company culture is interwoven systemically or whether it arises naturally based on talent choices[00:15:59] - Defining what talent means to him and the dimensions of it that matter[00:22:03] - What he’s learned about delivering messages effectively  [00:23:49] - The founding story and history of Trade Desk [00:28:33] - How he thinks about the key stakeholder groups around Trade Desk’s platform[00:30:50] - Figuring out who Trade Desk’s key customers were and identifying them writ large[00:34:55] - The composition of the universe and market of those who buy advertising [00:36:11] - Practical product implications based on their choice of service [00:40:16] - Building inventory legibility and its dimensions and importance [00:47:55] - The time between the first line of code to a multi million dollar revenue stream[00:50:29] - Markers for technology companies he’d look for that could achieve a similar scale [00:53:35] - How not being able to simulate poverty or hunger translates into his parenting [00:57:10] - Describing the margin differences between Trade Desk and Google[00:59:00] - What stands out as the defining moment in his firm’s history [01:01:50] - The kindest thing anyone has ever done for him

My guest this week is Carl Kawaja. It’s the second time I’ve had Carl on the show and my first conversation with him is one I go back to often. Carl is a portfolio manager at Capital Group, where he’s quietly overseen a huge portfolio for decades. He is one of the top investors operating today as well as one of my favorite people. The investing world has changed quite a bit since Carl and I first spoke in mid-2021 so this was a great chance to use Carl’s curious mind and wide range of experiences to discuss the regime change taking place across capital markets. In true Kawaja fashion, we go all over the map and discuss Apple, the Amazonian rainforest, baseball, the oil & gas industry, Muhammad Ali, and more. Please enjoy my great discussion with Carl Kawaja.   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, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it's quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/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 [00:02:44] - [First question] - What the market feels like to him today [00:06:00] - The pros and cons of the cost of capital and experimentation [00:09:09] - Things we can learn from Oil & Gas stocks and resource commodities in general [00:14:38] - Pulling apart the key lessons from Berkshire’s purchases of IBM and Apple [00:20:37] - The practical implications of wanting to land more soft-wins in investing that aren’t apparent out of the gate [00:25:52] - How he approaches and considers products and product cycles writ large [00:31:10] - The Systems Bible [00:33:15] - Thoughts about making money from value based strategies  [00:38:31] - His methodology to go about finding the next diamond in the rough  [00:42:48] - A New Innings [00:45:13] - The Arc of Boxing; Lessons from Muhammad Ali fighting Cleveland Williams [00:48:54] - Someone he thinks is an exemplar in both business and the world [00:54:37] - Don’t Sleep There Are Snakes [00:59:41] - The role fossil fuels play in the energy transition and the current regime change  [01:07:35] - What we can learn from uncontroversial transitions in the past

My guest this week is Daryl Morey, who is President of basketball operations for the Philadelphia 76ers. Daryl is a computer science graduate but has become one of the NBA’s most successful General Managers during his time with the Houston Rockets and the 76ers. Together with my friend and past guest of the show, Sam Hinkie, Daryl pioneered the analytics movement in basketball. He’s been so influential his style has its own name, “Moreyball”, a nod to Michael Lewis’s book about baseball, Moneyball. Daryl is also the co-founder of the MIT Sloan Sports Analytics Conference, which has become the gold standard forum for leaders in sports analytics. I had a blast talking to him about negotiation tactics, systems thinking, hiring, and a ton more. Please enjoy this great conversation with Daryl Morey. Listen to Founders podcast Founders Episode #136 A Success Story: Estee Lauder Invest Like the Best with David Senra: Passion & Pain 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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. 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[00:03:15] - [First question] - The basic principles of sports and what makes for a great sport[00:09:54] - How resource concentration influences outcomes in various sports[00:13:13] - The degree of certainty in predicting sports outcomes based on existing data[00:16:32] - Using the concept of KPIs to optimize for certain characteristics to win games[00:18:45] - Training teams on specific systems and plays versus leveraging individual talent[00:21:07] - Why superstar athletes are key to success in basketball[00:24:02] - Dealing with constant expected value calculations to appease stakeholders[00:25:30] - Building the organization’s back office to find talented athletes[00:28:32] - How he and other GMs make organization-level decisions[00:34:12] - Why he’s involved with basketball as opposed to other sports[00:36:17] - How he uses his frameworks to figure out systems outside of mainstream sports[00:37:41] - Problems with the rules and economic factors of professional soccer[00:42:54] - Trends he’s observed in the worlds of music, movies, and books[00:45:33] - His perspective on developing one’s own career path[00:48:22] - How challenges in his youth benefited him in the long run[00:49:28] - The person he would call for advice if he was stuck in a foreign prison[00:51:01] - His emphasis on first principles and why he supports free speech[00:52:31] - Takeaways from a Harvard negotiation class he took[00:57:07] - The power of refining the terms and definitions of a deal post-negotiation[00:58:51] - The four people in the world that intrigue him most[01:01:40] - The kindest thing anyone has ever done for him 

My guest today is Miles Grimshaw. Miles is in his early thirties and is a General Partner at Benchmark. His experience and success belie his age. He was an early investor in Segment, Benchling, and Airtable, all before they had 30 employees. I have learned a ton from Miles about software investing and that’s why I was excited to have him on the show. We discuss his biological approach to investing, whether pure API companies can be good businesses, and what most has his attention right now. Please enjoy this conversation with Miles Grimshaw.   Listen to Founders podcast   Founders Episode #136 A Success Story: Estee Lauder    Invest Like the Best with David Senra: Passion & Pain   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 streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/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 [00:02:57] - [First question] - His notion of the investor as a biologist or a physicist [00:05:24] - Why he seeks out new companies with unique business models [00:07:53] - How his investments are based on present and future needs in the market [00:11:55] - Evaluating the genetics of a nascent or small company [00:13:38] - The half-life of information as it flows through a company or platform [00:17:26] - Unpacking how software companies can survive re-evaluation periods [00:21:03] - The power of environment creation and facilitation [00:25:10] - The importance of user conferences [00:25:45] - A company’s potential for a differentiated second act as a sign of good genes [00:30:21] - Product quality, timing, and reinvention in tech startups [00:33:10] - Why it’s crucial for companies to avoid copying their heroes [00:37:41] - Breaking down market perspective on pure API companies [00:41:29] - His views on software targeted to vertical versus horizontal markets [00:44:29] - Carefully leveraging relationships with core customers [00:48:06] - Operational lessons from his experience with the companies he’s invested in [00:50:26] - His maxim that software development is as much an art as a science [00:51:12] - His idea of a product magician in the software industry [00:52:19] - Effects of new products and categories at the forefront of the space [00:58:21] - How software founders should prepare for 2023 [01:01:41] - How both market structure and product shape the genetics of a business [01:04:32] - The challenge of pricing and packaging for SaaS companies [01:06:42] - Cardinal sins in software investing [01:07:42] - The kindest thing anyone has ever done for him