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

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/