Tactical Lessons from Founding 3 Companies - Ryan Denehy (CEO, Electric AI)

For any founders or managers navigating go-to-market, strategy and org structure, this is the episode for you.

Ryan Denehy is Founder & CEO of Electric AI, a leading SMB IT management platform. He previously founded two companies: Royalty Media (sold to USA Today) and Swarm (sold to Groupon). Ryan is never afraid to share detailed advice from his own journey and also from advising/investing in other founders. This episode is rich with insights on how to identify and execute pivots, matching product and go-to-market, and why company building relies on manual hard work at every stage. Ryan also shares lessons on hiring, layoffs, and changing company strategy even at scale. You can see why Ryan is one of my favorite people to talk with and connect founders to for advice from this episode!

Where to Find Ryan:

* Twitter: https://x.com/DenehyXXL

* LinkedIn: https://www.linkedin.com/in/ryandenehy/

Where to Find Shomik:

* Twitter: https://twitter.com/shomikghosh21

* LinkedIn: https://www.linkedin.com/in/shomik-ghosh-a5a71319/

* Software Snack Bites Podcast: Apple Podcasts, Spotify, Google.

In this episode, we cover:

(00:58) – Ryan’s Entrepreneurship Background

(04:00) – Pivoting & Selling Royalty Media to USA Today

(07:45) – Industry Dynamics Around AdTech

(10:03) – Selling Swarm to Groupon and Experiencing Peak of Growth

(13:46) – Starting Electric AI Targeting SMBs

(18:02) – Matching Go-To-Market to SMB ACVs & Velocity

(20:12) – Why You Can’t Rely on Customer Referrals and Need to Cold Email / Call

(22:25) – Lessons Brought from First 2 Companies to Starting Electric AI

(26:15) – Founder Awareness Knowing How to Hire to Augment Weaknesses

(29:12) – Hiring Player Coaches Early

(30:40) – Changing the Business Model and Leadership at ~$50M ARR

(33:26) – How to Prepare For and Manage Large Team & Strategy Changes

(35:47) – Diagnosing Changes to Make in the R&D Org

(38:37) – Managing Culture Through Team & Strategy Changes

(41:37) – Applying AI to IT Ticket Comprehension & Process Automation

(43:11) – Internal Vendor Consolidation and Diagnosing Real AI Use Cases

(44:36) – Shadow IT Data Access & Controls

(47:00) – Wrap Up

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