Lessons Building Five Unicorns + Building Pathlight Ventures | Charley Ma & Mahdi Raza

The Peel with Turner Novak

Charley Ma and Mahdi Raza are the Co-founders of Pathlight Ventures, and were early employees at five unicorns, Plaid, Ramp, Alloy, Robinhood, and Stytch.

They share tactical advice for early stage startup employees, lessons getting Plaid and Ramp their first customers, and deciding to build Pathlight together.

Timestamps
(00:00) Intro
(02:30) Growing up in basements
(05:15) Charley’s journey to first biz hire at Plaid
(15:01) Advice on being a good startup employee
(19:34) Mahdi’s path to Robinhood
(26:33) Deciding between joining an early or late stage startup
(32:39) Why Charley joined Plaid despite VCs telling him not to
(38:52) Benefits of case studies in hiring
(39:58) Why every hyper growth company is a shit show
(44:24) Startup comp: equity, QSBS, early exercise, vesting
(49:59) Joining Ramp as the first Head of Growth
(58:35) How Ramp got its first customers
(01:02:06) Advice and common traps on early GTM strategies
(01:05:04) Why $1M ARR does not mean you have PMF
(01:06:51) Meeting when Robinhood bought, churned, then returned to Plaid
(01:09:54) Deciding to build Pathlight together
(01:23:06) Raising Fund 1 in 2021 and how bad timing almost killed it
(01:29:55) Reasons founders work with Pathlight
(01:32:04) Why most investors add no value and give bad advice
(01:36:44) Founders Pathlight invests in + Artie case study
(01:44:44) Competing with incumbent funds
(01:53:57) Raising a $75m Fund 2 in 2023
(02:02:22) Are Seed extensions good investments?
(02:07:45) Discussing startup valuations
(02:09:09) Mahdi’s 10-minute market outlook (as of 8/8/24)

Referenced
https://www.pathlight.vc/
https://plaid.com/
https://robinhood.com/us/en/
https://ramp.com/
https://stytch.com/
https://www.alloy.com/
https://www.artie.com/

Follow Charley
Twitter: https://twitter.com/charleyma
LinkedIn: https://www.linkedin.com/in/charleyma

Follow Mahdi
Twitter: https://twitter.com/mahdirazamr
LinkedIn: https://www.linkedin.com/in/mahdirazany

Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Newsletter: https://www.thespl.it/