What if you had to pivot after your Series C?

This weeks posts include a stomach wrenching experience from CircleUp founder Ryan Caldbeck who writes, “I remember sweating a lot. I remember feeling a pit. I remember for the first few months after the start of the downturn always- *always* – feeling terrified. Imagine feeling like that for an entire day. I felt that way for months.”


But first we owe our readers an apology.

Last week, we featured a section on great interviewers with Charlie Rose as an example. Several of our readers were quick to point out that in November 2017 Charlie Rose was accused of harassing female co-workers throughout his career. We were completely unaware of this when we cited him, and apologize for picking such a terrible example. Rose has since apologized, acknowledging some of the claims and denying others, and upon review of the facts we believe his behavior is reprehensible. We are so disappointed to be let down by our former hero, and have completely removed him from last week’s post, and noted the change there.

Tyler Cowen, who we featured next to him, is a great interviewer. I feel bad to have put him next to the discredited Rose.

Our readers were also quick to point out there are several awesome female interviewers worth exploring: Mary Lousie Kelly, Soledan O’Brien, and Terry Gross.


From the Operators

Ryan Caldbeck of CircleUp expresses the dramatic ups and downs of pivoting his company in this tweetstorm.

Avni Patel Thompson of Poppy grapples with the question of how to start a startup without funding in Finding the space to take the risk and build as a parent with bills..

Jasper Diamond Nathaniel of formerly of Revere tells a cautionary tail for co-founders making compromises to mix their ideas together. 18 months later, he was left running the company without them, and figuring out what to do in When Your Startup Fails.

Danielle Morrill of GitLab (also co-editor of BuriedReads) continues to process the loss of her former startup, and the physical space it inhabited, as if it were a relationship in 564 Pacific Ave..

The Mattermark team inside 564 Pacific. (Thank you René, Samiur, Beau, Sarah, Josh, Evion, and Bryan)

From the Investors

Naval Ravikant of AngelList is on a roll this week with his podcast Labor and Capital Are Older Forms of Leverage. A huge reason I’ve always been interested in software as a career is because it has zero marginal cost to reproduce, and so it huge impact in the economy. Naval lays out how capital has similar power, but labor is counter intuitively one you have to be careful with.

Albert Wenger of Union Square Ventures writes this week about the “asymmetry of limited upside, unlimited downside” in Learning from Notre Dame.

Seth Levine of Foundry Group along with Brad Feld encouraged us to get audited fairly early on at Mattermark. Having 3 years of audited financials helps immesurably with M&A and other options you want to keep open. This week he covers How much should you be paying your auditor?.

Om Malik of True Ventures is getting skeptical of Amazon’s dominance in e-commerece. I’m skeptical from a different angle. Everyone in Silicon Valley seems to beelieve Amazon has taken the cloud computing market and will never be unseated. If you’ve used their console as a developer, you know they are confusing, have poor documentation, and can be difficult to use. Someone is going to eat their lunch, and if you think it could be your startup, we’d love to talk as potential angel investors.