📺 Watch the full episode on Substack or 🎧 listen now on Apple Podcasts, Spotify, and YouTube
Millennial Masters is brought to you by:
This week’s Millennial Master is Nick Telson, an entrepreneur, angel investor, and podcaster who’s rewriting the rulebook for startup success. After scaling Design My Night to a $30m+ exit, Nick has continued to make waves, backing 54+ startups globally and co-founding Trumpet, a sales SaaS transforming the buyer journey.
In this episode, Nick unpacks his playbook for scaling businesses, investing wisely, and finding the grit to succeed. Plus, he shares what makes a startup worth betting on and the traits every founder needs to thrive.
🔗 Find Nick on LinkedIn, his website, and on X (Twitter)
Takeaways from Nick Telson’s interview:
1️⃣ Build sustainably, not just fast
Nick believes in smart growth, balancing ambition with a foundation that lasts.
2️⃣ Invest in people, not just ideas
As an angel investor, Nick looks for founders who bring vision, resilience, and execution power.
3️⃣ Understand your exit strategy
Nick shares how thinking long-term helped him maximise Design My Night’s acquisition.
4️⃣ Know your customer journey
Trumpet’s success stems from solving real pain points in sales processes and buyer experiences.
5️⃣ Hard work beats glamour
Nick reminds us that behind every success story is relentless effort and determination.
📖 Nick’s book recommendations
Shoe Dog by Phil Knight – The inspiring memoir of Nike’s co-founder, packed with lessons on perseverance and vision.
Losing My Virginity by Richard Branson – A candid look at the ups and downs of building the Virgin empire.
Steve Jobs by Walter Isaacson – A deep dive into the life and mind of one of the most iconic entrepreneurs of our time.
Too busy to read? Try this quick fix ⚡
Here’s how to fit more books into your life, even when you’re short on time.
In this episode we cover:
00:00 Introduction to Nick Telson
03:00 The Birth of Design My Night
05:51 Navigating the Early Challenges
08:21 Scaling the Business
10:53 Hiring for Culture and Fit
13:07 The Shift to Remote Work
17:35 The Exit Strategy and Earn-Out
23:48 Transitioning to Trumpet
28:31 The Importance of Sales in Startups
31:02 Finding the Right Co-Founder
34:08 Bootstrapping vs. VC Funding
37:32 Revenue Generation vs. Growth Potential
40:32 The Role of AI in Business
44:40 Investing in Startups: What Matters Most
48:16 The Hands-On Investor
50:03 Lessons from Pitch Deck Podcast
53:42 The Habits and Routines for Success
56:38 Sacrifices on the Entrepreneurial Journey
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