A few weeks back in this very email, I put out a request for a new content format we wanted to experiment with that we called “Startup Confessionals”.

From my note:

If you, or founders you know, are willing to share a startup confessional, we’d love to help. We can make these totally anonymized or public, whatever you're comfortable with. We'll be recording these remotely and aren't looking for hours long conversations — we're planning on editing them into quick lessons and anecdotes.

For example, here are “confessional” conversations I’ve had with people one-on-one just in the last few weeks:

— Over/under raising
— Surprising/shocking fundraising stories
— Horror stories of investors/board members behaving badly
— Hiring to please investors 
— Acquisitions blocked or held hostage by investors/board members

Thankfully, a few heeded the call. I think this week’s video captures the essence of what we were going for and the experiences we were hoping to mine. 

This week, we have stories and lessons from some legendary founders —

Ben Kauffman 
Founder of Quirky and Camp as well as CMO at Buzzfeed. Ben has an incredible knack for building brands and storytelling that has attracted some of the largest brand partnerships and most legendary investors. 

Harper Reed
Came into the national spotlight as the Chieff Technology Officer for Barack Obama’s re-election campaign. Shortly after, with encouragement and funding from then-Google CEO Eric Schmidt, he founder Modest which was later acquired by PayPal. Most recently, he wound down a venture backed startup Galactic. He’s currently exploring new ideas with his longtime collaborators. 

Finbarr Taylor  
Got his start in tech in various staff roles at companies like Groupon, Pebble, and Y Combinator. As a co-founder of Shogun, he and his partners bootstrapped to over $1M in ARR before raising their first round of funding. That first round let to another and then another. Shogun continues to be a thriving business that Finbarr remains on the board of and actively advises in addition to angel investing. His takeaways from bootstrapping to rocketship growth to near unicorn status are lessons not to be missed or dismissed. 

This is our first attempt at this format and we’re so grateful to Ben, Harper, and Finbarr (as well as the others we have in the can) for being willing to wade into such uncertain waters with us. 

We’re really happy with how this turned out and welcome your feedback on how we can improve it over time. 

We’d also welcome more stories from you or your networks. If you know someone who’d be fun/interesting/insightful on the topic of unpacking their founder, or early employee experiences and lessons, please send them our way!

As always, we hope you enjoy watching this one as much as we all enjoyed making it.

Bryce