Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to increase the likelihood of success and smoother sailing.

Next, he points to some of the foundational building blocks that keep him jazzed about his role at Hubspot still to this day, including the way he elicits feedback through “bug reports.” He also explains the reasoning behind his decision to never take on any direct reports and remain an individual contributor as a co-founder.

Finally, Dharmesh tells the story about how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product.

You can follow Dharmesh on Twitter at @dharmesh.