The emergence of AI everywhere is driving a surge in demand for authenticity. In this episode, we take a closer look at how the burden of authenticity has increased, and in some very challenging and expensive ways for early stage companies.

Bitching about inflation was something that only boomers used to do. But that’s changed over the last few years. While we hear a lot about inflation and its impact on consumers, we rarely talk about its impact on early stage companies. In this episode, we dive into the impact of inflation and how it’s changed almost everything about business building.

There are many hills in entrepreneurship…but very few of them are worth dying on. From the glorification of burnout to the “never quit” mentality, toxic narratives have deeply embedded themselves in startup culture at the expense of founders' mental health. Today, we are talking about how entrepreneurial machismo is literally killing us.

Content Warning: Discussion of self-harm, suicide, or suicidal thoughts. Please take care while listening.

Being transparent about challenges isn’t a sign of weakness; it’s actually one of the boldest moves you can make as a leader. And when you invite your team, advisors, and even your peers into the messy middle of things, you’ll unlock trust, collaboration, and growth that not only feels real, but is sustainable. In this episode, we talk about radical transparency: What does it look like in practice? How can it strengthen teams and culture? And where does it get tricky?

Whether it's marshaling the resources to start or securing cash to fuel growth, funding a business is hard, messy, and less fun than it looks on TV. The complexity isn’t just in finding money. It’s navigating all that comes with it. The costs, consequences, and contortions of taking on outside capital can leave even the best founders tied up in knots. In this episode, we unpack how these “pretzel problems” get made and the consequences that come with them.

2024 was a wild ride. Packed with surprises, challenges, and more than a few moments where we had to ask, ‘Did that really just happen?’ In this episode, we look back on the big themes of 2024—the moments that shaped us, the lessons that surprised us, and how it might set the stage for a stronger, more intentional 2025.

Usually I try to come up with a light hearted, clever title for each episode. But this topic is so viscerally important that every time I tried to be clever or cute I just got more enraged that this even has to be a topic. In this episode, Jennifer Jordan—who has earned her stripes as an innovator, an investor and one of the most respected mentors on the planet—shares her experience, a little of her rage, but mostly her hopes for a future where women aren't punished for all the amazing things that come with age.

Kim Folsom has been blazing her own trail for a long time, First as a founder, as a black female engineer, as an investor and now as one of the fiercest advocates for innovation in startup funding on the map today. In this episode we look back (why did it take so long??) and forward (how do we not repeat the mistakes of the past) to take a look at the changing landscape in early stage investing.