Lessons Building Five Unicorns + Building Pathlight Ventures | Charley Ma & Mahdi Raza
The Peel with Turner Novak
Turner Novak
4.6 • 11 Ratings
🗓️ 27 September 2024
⏱️ 143 minutes
🧾️ Download transcript
Summary
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/
Transcript
Click on a timestamp to play from that location
| 0:00.0 | And it'd gone all the way up to Jamie Diamond that Plad was kind of doing that. |
| 0:03.6 | This is seed stage. |
| 0:04.9 | We were really worried about Venmo. |
| 0:06.2 | It's disaggregating the relationship that we have with our banking customers. |
| 0:09.6 | Jamie Morgan internally, we're like, oh, we've shut down Platt. |
| 0:12.2 | They don't work. |
| 0:12.9 | But this is what I was also interviewing at Plaid. |
| 0:15.2 | I remember I linked up my bank account to Venmo. |
| 0:17.5 | I was like, Plad still works. |
| 0:19.1 | Like, don't worry. If you do join, we will tell you |
| 0:20.9 | how. Welcome to the PEO. Hi, I'm your host, Turner Novak, founder of Nanda Capital. I'm excited |
| 0:25.9 | for this conversation with Charlie Ma and Madi Raza, founders of Pathlight Ventures, and more |
| 0:31.1 | importantly, early employees at five uniforms, including Plaid, Ramp, Alloy, Robin Hood, and Stitch. |
| 0:38.3 | Nearly all the companies we helped build, we're not popular at the C round, |
| 0:42.3 | probably not even popular at the Series A round. |
| 0:44.3 | And all my BC friends were, no, we passed on that company. |
| 0:47.3 | There's all these red flags. |
| 0:48.3 | We talk about the best first startup job if you're not an engineer. |
| 0:52.3 | If you want to have a great career doing business things in a |
| 0:54.9 | startup go be an sDR meeting when charlie sold plaid to robin hood the funny thing is robin hood |
| 1:01.0 | we churn off of plaid yeah that was yeah that could have been that was tough but the important thing is |
| 1:06.0 | we we came back and how'd you win them back uh how Ramp got its very first customers. |
... |
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