My guest today is Parker Conrad, co-founder and CEO of Rippling. I wanted to speak to Parker because he is building Rippling in a way that we don’t come across often. Rather than focus narrowly on one product, he is building a suite of interrelated products simultaneously to carry out the functions of HR, Finance, and IT for companies. He calls it a compound company and we discuss the idea, as well as some of his other non-traditional theories, in detail. Please enjoy this conversation with Parker Conrad.   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.    -----   This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.   -----   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] - Overview of what a compound startup is  [00:06:32] - What he’s learned about picking customers effectively  [00:08:48] - Key chapters when it comes to building a compound startup  [00:13:48] - What great looks like at the base level infrastructure of employee data [00:20:15] - His overall philosophy on product development writ large  [00:25:09] - His role as a capital allocator and distributing resources to his teams [00:27:19] - The amount of products they offer and whether or not there’s a tradeoff between time, cost, and quality when building software [00:31:36] - Possibly incorporating an app-like store on top of their existing infrastructure  [00:34:43] - Speed and the kinds of people that can sustain it for long periods of time [00:36:30] - What motivates him on a personal level and harnessing motivation in general [00:42:31] - Whether or not there’s an end to feeling hurt by false public perceptions when building in public [00:44:12] - The intersection of leadership and communication inside of a business and what he’s learned about great communication  [00:48:00] - The paradox of how focusing on non-scalable actions perpetuates growth and productivity and his views on productivity-per-person [00:50:36] - The best example of a moment that required the most grit and perseverance while building his company  [00:52:28] - How to successfully get former founders to come work for him  [00:54:47] - What good private equity investors do  [00:58:31] - The kindest thing anyone has ever done for him

Parker Conrad, CEO of Rippling and a successful entrepreneur, shares insights from his journey building the $13B company. He discusses the concept of 'founder mode' and its practical application at Rippling, contrasting his experiences at Zenefits. Parker candidly addresses the complexities of investor relationships, noting that much of VC advice can be overrated. He also reflects on the dynamics of hiring, governance challenges, and the importance of anecdotal evidence in decision-making, all while emphasizing the value of speed and quality in execution.

Parker Conrad, founder of Zenefits & Rippling, discusses the controversy at Zenefits and the challenges faced in scaling the company. He also talks about building a suite of integrated products on a foundation of employee data, the urgency of Y Combinator, and how Rippling helps companies become more efficient.

Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees’ payroll, benefits, expenses, devices, apps & more—in one place. To date, Parker has raised over $697M for Rippling from some of the best including Sequoia, Founders Fund, Greenoaks, Bedrock, Kleiner Perkins and Initialized to name a few. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund. In Today's Episode with Parker Conrad: 1.) Entry in Startups and Zenefits: How did Parker make his way into the world of startups? How did Parker end up being kicked out of his own company, Zenefits? How did he respond? How did that experience of being kicked out of Zenefits inspire him to build Rippling? 2.) Parker Conrad: The Leader: How does Parker define "high performance"? How would Parker describe his leadership style today? Why does Parker fundamentally disagree that with speed comes a trade-off in quality? How does Parker ensure Rippling does all things fast and to the best of its ability? How would Parker break down his decision-making framework today? How does he decide what to prioritize vs not? How does he decide what to delegate vs not? What are Parker's biggest insecurities in leadership today? How have they changed over time? What does Parker do to combat and mitigate them? 3.) Rippling: The Compound Startup How does Parker define a compound startup? What types of business do this verticalized approach work for vs not work for? What does Parker believe are the 4 core benefits of this approach? What are the single biggest challenges of building a compound startup? 4.) Rippling: The Economics: How does this compound startup approach impact ability to cross-sell? How much net new ARR today comes from cross-sell? What have been some of Rippling's biggest lessons on what it takes to do cross-sell so effectively? How do the margin profiles differ across their different products? How have the margin profiles changed over time? Why does Parker not believe that most startup margins are accurate? How does the compound startup approach change the amount invested in R&D? How does that impact the fundraising requirements of the business? 5.) Rippling: The Partner Ecosystem: How does Rippling think about building out the best partner ecosystem? What will it take for that to work? Why do Rippling want to introduce services that compete with their own products? Why do they not only build their own? How do the margins differ when comparing revenue share on partner products vs Rippling products? What are the single biggest barriers to this partner ecosystem working?

Parker Conrad, founder of Sigfig and Zenefits, talks about his journey as an entrepreneur, facing challenges while building his companies. He discusses the downfall of Zenefits and lessons learned, the power of media narratives and VC involvement, and the impact of social media on business. Conrad introduces Rippling, a new approach to business software, and emphasizes the importance of employee data. He also touches on the role of founders in business units and shares his perspective on the current state of San Francisco and the tech industry.

Parker Conrad, CEO and co-founder of Rippling, shares insights on building a leading HR tech company amidst fierce competition. He discusses the importance of addressing market pain points and reveals the role of AI in transforming traditional models. Conrad also explores Rippling's unique marketing strategy, which gained visibility on a budget. He emphasizes hands-on leadership and transparency in founder-investor dynamics, sharing valuable lessons on personal growth and entrepreneurial challenges.

Parker Conrad and Parker Thompson debate the value VCs bring to founders, addressing misalignment issues, VC deal influencers, and ethical dilemmas. They explore the dynamics of investor involvement, the notion of value-add in VCs, founder-investor relations, and strategic financing decisions for startups. Rippling's solutions for HR and IT challenges also discussed.

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world.  Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business. Dara Khosrowshahi is the CEO of Uber, where he has managed the company’s business in more than 70 countries around the world since 2017. Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees’ payroll, benefits, expenses, devices, apps & more—in one place. Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world’s first Wi-Fi video doorbell while working in his garage in 2011. The company sold to Amazon for $1BN. Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees. Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events. Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN in 2021. Question of the Day: What are the world's tech leaders running from?

Parker Conrad, CEO of Rippling and Mamoon Hamid, partner at Kleiner Perkins discuss their experiences with startups, the challenges they faced, and the importance of executives being involved in problem-solving. They also delve into the concept of compound startups, deep integrations, and the inefficiency of buying separate software components. The podcast offers insights on fundraising dynamics, starting companies for the right reasons, and the unique series A of Rippling.

Parker Conrad, Co-Founder and CEO of Rippling, shares insights and challenges of starting companies. They discuss the motivation behind starting Rippling, the need for naivete in the startup world, building a compound product, a day in the life of the CEO, and reflecting on a career journey with highs and lows.