Shawn Sheikh: From Y Combinator Founder to Cash Flowing Empire (Just Go Grind, Episode #354)


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Mar 10 2025 53 mins  

Episode 354: Justin Gordon interviews Shawn Sheikh, Co-Founder and Managing Partner of Adly, about how he builds, acquires, and invests in companies.

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Show Notes:

00:00 What’s coming in the episode…

01:14 Introduction

02:55 Shawn Sheikh’s background

04:45 Starting Solve

09:15 Starting PivotCMO

11:29 Meeting Adly’s co-founder, Fred Chiang

13:38 Selling PivotCMO

17:14 Moving on to company investment and acquisition

22:04 Raising capital

25:10 Shawn’s goals and motivations

27:26 Adly’s deal flow

29:30 What to look for in a deal

31:46 Red flags in a deal

34:21 Why is Adly winning the deals?

36:32 Next steps after the deal

38:45 Building Adly’s team

40:06 Shawn’s day to day at Adly

42:33 Adly’s portfolio companies

44:17 Adly’s purchase of Smodin AI

48:57 Shawn’s approach to starting something new

50:50 What’s next?

52:26 How to reach out to Shawn

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