B2BaCEO (with Ashu Garg)

My guest today is Sanjit Biswas, the co-founder and CEO of Samsara, a platform that helps companies digitize their physical operations. In 2023, Samsara reached $1 billion in ARR, making it one of the fastest startups in history to hit this milestone.

But this wasn't Sanjit's first major success. Before starting Samsara, Sanjit left his Ph.D at MIT to build Meraki, a cloud networking company that Cisco acquired for $1.2 billion in 2012.

In our conversation, Sanjit shares his journey from grad school research to bootstrapping Meraki in the early days. He reflects on the lessons he learned from Meraki's pivot to the enterprise, the decision to sell to Cisco, and the insights that led him to start Samsara.

We then turn to how Samsara found product-market fit, Sanjit's philosophy on allocating capital, and the areas where he believes generative AI will have the biggest impact.

It was a really fun and insightful conversation that I think you'll enjoy!

(00:00) Intro
(00:16) Sanjit's background and the genesis of Meraki
(06:25) Meraki's pivot to the enterprise and rapid growth
(09:45) Lessons from building Meraki's enterprise sales motion
(16:15) The decision to sell Meraki to Cisco
(20:05) Founding Samsara and its mission
(27:11) Defining Samsara's product strategy based on customer feedback
(31:00) Samsara's unique journey to $1B in revenue
(39:16) Sanjit’s "70/20/10” framework for allocating capital
(43:13) The importance of board alignment and company culture
(50:58) Sanjit's thoughts on AI and hype cycles
(54:22) Sanjit's advice for aspiring entrepreneurs

My guest today is Doug Winter, the founder and CEO of Seismic, a leading enterprise sales enablement platform. Today, Seismic has a team of 1,500 people and nearly $400 million in recurring revenue. We start the conversation with Doug explaining what sales enablement actually means. From there, we turn to the early days of Seismic and unpack Doug’s approach to finding product-market fit, positioning, and targeting enterprise customers from day one. He speaks candidly about the challenges of scaling and closes with actionable advice for founders in 2024. Fewer than 1% of B2B software companies reach Seismic’s scale. Doug’s story offers a valuable blueprint for founders with similarly audacious ambitions. I hope you find this conversation as inspiring as I did. Let’s dive in! (00:00) Cold open (2:21) Doug explains what sales enablement is (3:39) Genesis of the idea for Seismic (7:08) Seismic's scrappy early days (13:10) Lessons from fundraising (18:23) Targeting large enterprises from day one (22:32) Scaling a GTM engine (28:23) Making proactive leadership changes (37:12) Running great board meetings (40:59) Impact of AI on Seismic's business (44:42) Advice for founders starting in 2024

My guest this month is Naveen Rao, the co-founder of MosaicML and current head of Generative AI at Databricks. Naveen's journey is unique, as it echoes the evolution of AI itself. He’s best known for founding and selling two successful companies. The first, Nervana, an AI-focused chip company, was acquired by Intel for $400 million in 2016. The second, MosaicML, was acquired by Databricks in June for $1.3 billion. In our conversation, we unpack the insights and frameworks that led Naveen to make these bets in the first place. We begin by exploring his long history in AI research and startups, from his early days at Qualcomm, his founding of Nervana, and the genesis of MosaicML. We then turn to the complexities of the ever-changing AI landscape and go behind the scenes of MosaicML’s acquisition by Databricks. We close with Naveen’s takes on the most urgent questions in AI, including the recent tumult at OpenAI, the road to AGI, the role of regulation, and where he thinks generative AI will go next. What struck me most is Naveen’s remarkable ability to not only anticipate the future but also actively pave the path toward it. For founders looking to navigate our current AI moment, this episode is full of valuable lessons.

In this episode of B2BaCEO, I speak with Robert Nishihara, co-founder and CEO of Anyscale. Anyscale’s aspiration is to build the fastest, most cost-efficient infrastructure for running LLMs and AI workloads. When it is successful, Anyscale will be to the AI era what Microsoft was for the PC era: the underlying operating system on which all AI applications are developed and run. Anyscale is built on Ray, an open-source compute framework that Robert and his co-founders developed as PhD students at UC Berkeley. Under the guidance of Professor Ion Stoica, who also co-founded Conviva and Databricks, the team sought to make distributed computing broadly accessible. Anyscale was then launched as a fully managed platform for Ray, making even the toughest problems in distributed computing easy for developers to tackle. Today, Anyscale is a billion-dollar business powering mission-critical AI use cases at companies like Amazon, Cohere, Hugging Face, NVIDIA, OpenAI, and Visa. If you’ve been a PhD student at UC Berkeley, created a popular open-source framework, and built a billion-dollar business on top of it, you’ve likely learned a thing or two along the way. Robert’s story offers valuable lessons for fellow founders and builders at all stages of the startup journey.

My guest this month is Tracy Young, the co-founder and former CEO of PlanGrid, a productivity tool for construction companies. From going through YC and losing a co-founder to cancer, to being acquired by Autodesk for $875 million, Tracy has picked up many valuable lessons that other founders and CEOs can learn from. Our conversation unpacks these lessons, including finding (and keeping!) product-market fit, navigating startup growing pains, showing up effectively to board meetings, and managing the emotional toll of fundraising. We also speak about Tracy’s new venture, TigerEye, and what she’s doing differently the second time around. After having countless conversations with founders over the years, I thought I’d heard it all. Tracy proved me wrong. Her story serves as an inspiration for aspiring entrepreneurs in any industry.

If you’re not hardcore about AI, then stop the podcast now — because this episode for real technology nerds. Ashu’s guest is Matei Zaharia, CTO and cofounder of Databricks, and a professor of computer science at Stanford University. Ashu and Matei cover a lot of ground — most of it technical, all of it very relevant for anyone who’s serious about building with artificial intelligence. They start with a discussion of Databricks’ early days: how the startup established a foothold in a market dominated by entrenched incumbents and some of the challenges Matei and his cofounders faced. The rest of the conversation is all about AI. Matei breaks down the most common challenges that enterprises run into when attempting to adopt AI. He shares tips for how startups can best deploy foundation models. And he speculates on what the game-changing new use cases for AI will be over the next two years. Matei also pulls back the kimono on some of the cutting-edge machine-learning research he and his team at Stanford are working on. Finally, listen to the end for a fascinating exchange about artificial intelligence beyond large language models.

As everyone listening to this podcast knows, the release of ChatGPT last November ushered in a new age of AI and catalyzed a wave of AI startups. For this episode of B2BaCEO, Ashu goes deep on AI with Bobby Yerramilli-Rao, former serial entrepreneur and investor, and current Chief Strategy Officer at Microsoft. Ashu picks Bobby’s brain on what sectors and problem spaces he thinks are ripe for innovation with AI and what the opportunities for startups are. They then dissect the four layers of the AI stack, from applications to platforms to infrastructure to models. Lastly, they talk about flavors of artificial intelligence beyond large language models. If you’re a founder or executive who wants to understand the AI moment and all the opportunities it holds for enterprises and society — listen to this conversation.

Beerud Sheth is the Co-Founder and CEO of Gupshup, a leading platform for cloud messaging. Prior to that he was the cofounder of what is now Upwork, a pioneer of online freelancing and remote work. Beerud took the slow and steady pace to winning the race, building two unicorns over 25 years. On the show, he and Ashu draw from Beerud’s depth of experience and break down how a company can achieve capital-efficient growth in the current economic environment. They also lay out the case for why India might be the Silicon Valley of the future.

Jonathan Siddharth is cofounder and CEO of Turing, the platform that helps companies source, vet, match, and manage the world's best software developers remotely. Jonathan started Turing in Foundation Capital’s offices four years ago and he’s since grown it into a $4B company. On this episode of B2BaCEO, Ashu gets him to talk about how he did it: from best practices for hiring execs and communicating with investors, to the unique fundraising machine that Turing’s built, to navigating through choppy economic waters. Jonathan is one of the most methodical, forward-thinking entrepreneurs active today. For four wild years, he’s been living the startup life, and fighting the founder’s fight, and embodying this show’s ideal of growing from engineer to CEO.

Alex Bouaziz is the guest for this edition of the show. He is the Co-founder and CEO of Deel, a global payroll solution that helps businesses hire anyone, anywhere. Founded in 2019, Alex and his team have grown the company into a unicorn with almost a thousand employees in just three short years! In this conversation, he opens up about the thrills and perils of scaling Deel so rapidly: from the things he got right, like how to hire and how to foster a culture of excellence; to where he got it dead wrong, including titles and product development. Alex and Ashu hit every angle of what it takes to build an organization.