Pointypress Live is entering its third season, and I’m thrilled to be leading the events again this year. The first event is on February 1, 2023, and will feature a timely discussion on what to do if your company can’t raise a Series A. We have Cambly’s Sameer Shariff and Benchmark’s Sarah Tavel speaking at the first event.
Of course, Pointypress Live is free to attend. This weekly event/episode records live each Wednesday at 12:00/3:00 PST/EST. Register on Hopin to ask questions and network with guests and other attendees. The event also streams to Facebook Live and YouTube and will also be on Twitter Spaces.
TCL’s mission is still to help founders build better venture-backed businesses. But going into 2023, there’s new urgency behind this mission. Pointypress Live started in the heady days of 2021, and now in early 2023, the startup world is experiencing radical changes. It’s harder to fundraise, sales cycles are much longer, and investors (and their LPs) have different expectations that are affecting all industries.
A few updates for 2023
- Pointypress Live is back on Hopin. Each event will have a dedicated Hopin room, allowing you, the viewer, to ask the guests questions. You have to register, and sign up for each event. But it’s worth the hassle. Trust me.
- I’m also turning to Twitter to help source some questions for each week’s guest. It’s critical to me that you get to ask the questions you find most interesting, so if you can’t log in to Hopin, send me questions over Twitter at @mjburnsy.
- The TCL Podcast! I got a producer, and the lackluster TCL Podcast is getting some serious love. Each Monday, we’ll upload an edited and condensed version of TCL. And the logo is changing thanks to @dicebourbon.
- Pitch Practice is back! Apply to present your company using this form.
Sarah Tavel (Benchmark) and Sameer Shariff (Cambly) — 2/1/2023
Cambly looks like a sure bet right now, but as you’ll hear from Sameer, it was a struggle to get to this point. After failing to raise a Series A, the company had to change its model overnight. When VC after VC said no, Cambly had to find a way to make a profit to keep the doors open. Since then, the company went on to raise a $20 million Series A and a $60 million Series B, but only because the company took the hard steps to seek profitability earlier than expected.
Christina Ross (Cube) and Rajeev Batra (Mayfield) — 2/8/2023
Christina Ross and her company, Cube, are on a mission to improve financial planning and analysis. Unlike competitors, Cube is not trying to replace internal spreadsheets, but rather live alongside these beloved sheets. Cube’s strategy is meeting its customers where they’re at. Hear how this novel approach was developed and how it attracted investments from major firms, including Rajeev Batra at Mayfield Fund.
Christina Cacioppo (Vanta) and Andrew Reed (Sequoia) — 2/15/2023
Christina Cacioppo co-founded Vanta to help companies stay up-to-date with ever-changing compliances. And the industry responded enthusiastically. The company quickly raised over $200 million in venture capital, becoming a unicorn with its $150 million Series B in October 2022. Hear from Cacioppo and Sequoia Capital general partner Andrew Reed on Vanta’s growth trajectory and fundraising strategy.
Sagi Eliyahu (Tonkean) and Joanne Chen (Foundation Capital) — 2/22/2023
David Blumberg (Blumberg Capital) and Tanis Jorge (Trulioo) — 3/1/2023
Mark Goldberg (Index Ventures) and Rick Song (Persona) — 3/8/2023
Mamoon Hamid (Kleiner Perkins) and Arianna Huffington (Thrive Global) — 3/15/2023
Eric Tarczynski (Contrary) and Harshita Arora (AtoB) — 3/22/2023