Nick Telson-Sillett on Trumpet, Angel Investing, and Finding Purpose - Part 2

This episode is proudly sponsored by FounderCatalyst.Get 5% off their services by clicking this link:https://2ly.link/1zDIJ-------------------------------------------------------------------Nick Telson-Sillett on Trumpet, Angel Investing, and Finding Purpose | Founders UnpluggedAfter exiting DesignMyNight, Nick Telson-Sillett found himself at a crossroads—what comes next after a successful startup exit? In this episode, he sits down with Greg McCallum to discuss the journey from selling his first company to building Trumpet, a SaaS tool reshaping sales engagement.Nick shares his real take on life after an exit, the unexpected challenges of finding purpose, and why angel investing wasn’t as fulfilling as he first thought. He also breaks down:🔹 The strategic process behind Trumpet’s ideation (and how it almost had a terrible name)🔹 Why branding & user experience matter more than most founders think🔹 The truth about raising VC funding and managing investor expectations🔹 How hiring a non-founder CEO changed everything🔹 His biggest lessons from investing in 50+ startupsThis is a must-watch for founders, investors, and anyone scaling a business. If you enjoyed Part One, you won’t want to miss this!Chapters00:00 The Transition from Design My Night to Trumpet02:46 Finding Purpose After Success06:07 The Ideation Process for Trumpet09:12 Branding and Positioning Trumpet11:52 Creating a Unique User Experience14:59 Feedback and Iteration in Product Development18:01 The Evolution of Trumpet's Concept21:08 Fundraising Strategies and Lessons Learned23:59 Navigating the Challenges of Rapid Growth30:08 Building Internal Structures for Growth31:44 Navigating the Pressure of VC Expectations35:06 Long-Term Vision vs. Short-Term Metrics38:12 Finding the Right CEO: The Hiring Process39:54 The Journey into Angel Investing44:47 Finding Purpose Beyond Financial SuccessFollow Nick on LinkedIn here: https://www.linkedin.com/in/nicktelson/Check out Trumpet here:https://www.sendtrumpet.com/Want a 1-hour free advisory session with our host, Greg McCallum? 👇👇👇👇👇👇👇https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c8f5cecd-0222-4c6e-92d1-ea9f224a60fd#FoundersUnplugged #NickTelson #StartupLessons #AngelInvesting #ScalingStartups #VCFunding