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

Just Go Grind

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

--

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.

--

This episode is also brought to you by TRIBE. TRIBE is a community for fast growing early to mid-stage entrepreneurs. It includes facilitated peer groups of 6, retreats, guest speakers, book club, forums, and more. Qualifications: Entrepreneurs generally doing between $500k and $15 million per year in revenue. Apply to TRIBE today and save $300 off the yearly membership price when you mention Just Go Grind!

--

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

Referenced:

• Adly

• Solve (acquired by Blacklane)

• Pivot CMO (acquired by Conspiracy Theory and Unfold)

• DoubleList

• Smodin

• Guthy Renker

Connect with Justin:

• Twitter: https://x.com/justingordon212
• Instagram: https://www.instagram.com/justingordon8/
• LinkedIn: https://www.linkedin.com/in/justincharlesgordon/

What Justin is working on:

• Just Go Grind Newsletter: https://www.justgogrind.com/subscribe
• Running (Strava): https://www.strava.com/athletes/52394979
• Hiring: https://partnerslink.athyna.com/pod
• Scouting: https://headline.com/