In Depth

Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels.

In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift.

He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication.

It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.

You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom” 

For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg. 

To learn more about how Drift approaches storytelling, check out this article David wrote for Inc:

https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html 

To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/

You can email us questions directly at [email protected] or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson) 

Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas.

Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape.

But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders.

You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App).

You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Our first episode is with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. We’ve interviewed her four times on First Round Review — which might be a record — because the advice she has to share and the experiences she can draw from are unbelievably helpful to founders and startup leaders. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School.

While on The Review she’s shared advice on everything from managing your emotions and struggling with scaling, to codifying your culture and setting up your first comp system, today’s conversation is focused on a different topic — management. 

This is a topic Molly has strong opinions on—she’s seen time and time again across her career how so many startup mistakes come down to general management issues. We cover everything from the traps that are easy to fall into, to why you should be spending more time with your highest—not your lowest—performers, to the managers she’s learned the most from, so there’s tons of insightful advice and practical tactics for both first-time managers and seasoned leaders alike.

You can read more about Molly’s approach to scaling startups on First Round Review. We particularly recommend following her advice to ‘give away your Legos’ https://firstround.com/review/give-away-your-legos-and-other-commandments-for-scaling-startups/

And here’s the article on compensation that Molly mentioned in the interview: https://firstround.com/review/A-Counterintuitive-System-for-Startup-Compensation/ 

You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson 

Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves.

We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found.

I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com