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How to Actually Scale a Startup, From a Founder Who Did It 3x (Just Go Grind, Episode #364)

May 24, 2025

Episode 364: Justin Gordon interviews Waseem Daher, Co-Founder of Pilot, about his experience as a 3x founder building a startup that's raised $150M+ in venture capital. 

Check out the founder salary report.

Watch this episode and others on YouTube.

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This episode is brought to you by Rho. With Rho, founders get:

  • A single pane of glass they can use to run and scale their business from Day 1: Bank account, corporate cards to start running – and expense management, bill pay automation, and accounting to help you move fast as you scale.
  • Rho is trusted by thousands of companies ranging from two-person YC companies to brands like Perplexity, Cal.com, Splitwise and more.
  • The big thing with Rho: Every customer has a "person" at Rho. 24/7 customer support - phone, text, email - we will be there at every critical milestone in your startup's journey.

To learn why startups choose Rho, visit www.rho.co today.

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Show Notes:

00:00 What’s coming in the episode…
00:27 Introduction
01:36 Waseem’s passion for startups 
03:58 Starting Pilot 
05:43 Why was it the right time to start Pilot 
13:30 Early days at Pilot
19:27 Raising capital for Pilot
22:32 Waseem’s mentality on fundraising
26:36 The story behind Pilot’s Series A round
30:22 Pilot’s first sales 
34:09 Pilot’s ICP 
36:44 Growth strategies back then 
40:09 Growth strategies today
48:34 The evolution of Waseem’s role as a founder
54:25 Be a part of Pilot

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