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

Just Go Grind

Release Date: 05/24/2025

How Delphi Raised $16M from Sequoia to Build Digital Minds with Dara Ladjevardian (Just Go Grind Episode #369) show art How Delphi Raised $16M from Sequoia to Build Digital Minds with Dara Ladjevardian (Just Go Grind Episode #369)

Just Go Grind

Episode 369: Justin Gordon interviews Dara Ladjevardian, Founder and CEO of Delphi, a company that creates a digital you - available 24/7 for coaching, Q&A, education, and more. Learn more about Delphi: Watch this episode and others on . Thank you to our sponsor, Relay Human Cloud! ​ Find your next team member in minutes with Relay Human Cloud. Offshore talent, in Relay Human Cloud's offices, dedicated to you. Save up to 75% on labor costs while improving the quality of life for your team. Use code LAGRIND for $500 off every resource every year. Learn more about Relay Human...

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Just Go Grind

Episode 368: Justin Gordon interviews Andrew D'Souza, Founder and CEO of Boardy, an AI Super Connector that helps you get the right introduction at the right time. Boardy raised an $8M seed round early in 2025, just months after announcing a $3M pre-seed round. Learn more about Boardy: Watch this episode and others on . Thank you to our sponsor, Relay Human Cloud! ​ Find your next team member in minutes with Relay Human Cloud. Offshore talent, in Relay Human Cloud's offices, dedicated to you. Save up to 75% on labor costs while improving the quality of life for your team. Use code...

info_outline 0 to $9.5M Series A: Inside Guidesly’s Journey with David Lord (Just Go Grind Episode #367) show art 0 to $9.5M Series A: Inside Guidesly’s Journey with David Lord (Just Go Grind Episode #367)

Just Go Grind

Episode 367: Justin Gordon interviews David Lord, Founder of Guidesly, the platform for booking the world's best outdoor trips and activities. Learn more about Guidesly: Applications now open for 43North, the accelerator David went through with Guidesly:  Watch this episode and others on . --- Connect with Justin:  Twitter:  Instagram:  LinkedIn:  --- What Justin is working on:  Just Go Grind Newsletter:  The LA Grind Local Newsletter:  Newsletter Founder Course & Community:  Running (Strava):  Hiring:  Scouting: 

info_outline How 43North Built a $5M-Per-Year Startup Accelerator in Buffalo (Just Go Grind, Episode #366) show art How 43North Built a $5M-Per-Year Startup Accelerator in Buffalo (Just Go Grind, Episode #366)

Just Go Grind

Episode 366: Justin Gordon interviews Colleen Heidinger, President of 43North, a pioneering startup competition and venture program focused on building Buffalo into a thriving center for innovation and entrepreneurship. invests $5 million annually in companies that relocate to Buffalo through its immersive accelerator program. Applications now open: Watch this episode and others on . --- Show Notes: 00:00 What’s coming in the episode… 00:23 Introduction 01:01 What is 43North? 03:27 The early days of 43North 07:08 Covid days at 43North 09:14 Admission process 16:02 Getting the...

info_outline How Mehul Nariyawala Built Matic, the Smartest Home Robot Vacuum (Just Go Grind, Episode #365) show art How Mehul Nariyawala Built Matic, the Smartest Home Robot Vacuum (Just Go Grind, Episode #365)

Just Go Grind

Episode 365: Justin Gordon interviews Mehul Nariyawala, Co-Founder of Matic Robots, about his experience building two successful venture-backed startups, Flutter and Matic.  Learn more about , the world’s most advanced floor cleaner.  Watch this episode and others on . --- This episode is brought to you by . 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...

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

Just Go Grind

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 . Watch this episode and others on . --- This episode is brought to you by . 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...

info_outline How Abdul Al-Asaad of Basic Capital is Building a New 401(k) (Just Go Grind, Episode #363) show art How Abdul Al-Asaad of Basic Capital is Building a New 401(k) (Just Go Grind, Episode #363)

Just Go Grind

Episode 363: Justin Gordon interviews Abdul Al-Assad, co-founder and CEO of Basic Capital, about how he created the startup solution to finance investments and close the American ownership gap.  Check out . Watch this episode and others on . --- This episode is brought to you by . 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...

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Just Go Grind

Episode 362: Justin Gordon interviews Jeremy Yamaguchi, founder of Lawn Love and Cabana Pools, about how he built and grew several “high-suck” companies in the home services industry. Check out Jeremy's company, .  Watch this episode and others on . --- This episode is brought to you by . 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...

info_outline Zero to $80M in 4 years with John Andrew Entwistle of Wander (Just Go Grind, Episode #361) show art Zero to $80M in 4 years with John Andrew Entwistle of Wander (Just Go Grind, Episode #361)

Just Go Grind

Episode 361: Justin Gordon interviews John Andrew Entwistle, Founder and CEO of Wander, about how he built a luxury travel business at the age of 23. Book a Wander with inspiring views, hotel-grade amenities, dreamy beds, top-tier cleaning, and 24/7 concierge service. It’s a vacation home, but better: Watch this episode and others on . --- This episode is brought to you by . 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...

info_outline How Nick Huber Built a $100M+ Empire with How Nick Huber Built a $100M+ Empire with "Unsexy" Businesses (Just Go Grind, Episode #360)

Just Go Grind

Episode 360: Justin Gordon interviews Nick Huber, entrepreneur, investor, and author of "The Sweaty Startup", about how he built three thriving companies and a well-known online brand. Link to buy Nick's book on Amazon: --- This episode is brought to you by . 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...

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More Episodes

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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