Angel Investing, Being Creative and Getting Wiser [Video]

Nick Telson-Sillett. He isn’t just the famous host of “Pitch Deck,” a go-to podcast for angel investing insights; he’s a real-deal entrepreneur who, after selling his own company five years ago, decided to give back. Through Horseplay Ventures, he supports up-and-coming startups, and with his new software company, Trumpet, he’s still in the game. Eloquent and open-hearted, Nick’s here to share with us his personal wisdom and the lessons he’s picked up from his numerous podcast guests.

Nick Telson-Sillett: https://www.linkedin.com/in/nicktelson/

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TIME STAMPS:

00:00:00: Intro
00:01:07: Nick’s life post business sale
00:01:18: The impact of money on happiness
00:01:27: Future plans for Nick
00:01:45: Thoughts on Angel investing
00:02:06: Lessons learned from business
00:02:53: How Nick wants to be remembered
00:03:05: Reflecting on the moment of selling the company
00:04:07: Personal crisis post-sale
00:05:13: Shift in idea of purpose after business sale
00:06:47: Self-discovery and ideation post-sale
00:07:44: Beginning of angel investing and new approach to stress
00:08:42: Motivations for continuing in business and advisory roles
00:09:14: Continuing desire to succeed and win
00:10:33: Discussion on the motivation for starting the first business
00:12:17: Exercise for financial freedom
00:13:36: Reflection on accomplishment of achieveing financial goal
00:16:02: Thoughts on selling the company
00:16:35: Recollections of relief post-sale
00:18:12: Comparing past business motivation with current Trumpet business
00:19:10: Adjusting to new founder’s financial objectives
00:20:07: Current motivation – learning and challenging self
00:20:41: Identity crisis post-business sale
00:21:56: Adjusting to new identity as a “startup guy”.
00:22:36: Discussion about identity and starting of Podcast
00:23:13: Benefits of raising money from angel investors for early-stage businesses
00:24:06: Different formats for Podcast and its live nature
00:24:43: Purpose of starting the Podcast – Making angel investing less secretive
00:25:13: Success rate of the Podcast
00:26:02: Networking and forming friendships via the Podcast
00:27:32: Relation of Podcast and personal purpose post-business exit
00:28:57: Future plans post-trumpet days
00:29:24: Current Fulfillment rating
00:31:01: Changes in views towards money and wealth after exit
00:33:16: Importance of taking time for joy and presence
00:34:02: Discovering joy in walking
00:35:15: Health restoration post-exit during Covid-
00:36:38: Thoughts on imposter syndrome
00:39:10: Candidness about making mistakes and continuous learning
00:41:39: Mental health struggle during ‘my night’ and post-exit realization
00:43:40: Discussions on Purpose and Joy
00:44:51: Thoughts on Growing Up and Impacting the Community
00:46:56: Experience in Angel Investing
00:51:04: Current Position in Angel Investing
00:52:48: Thoughts on Why Founders don’t Ask for Help
00:55:10: Reason Why Founders Become Angel Investors
00:59:44: Effect of Exit on Relationships with Friends and Family
01:01:06: Parents’ Influence on Becoming an Entrepreneur
01:02:25: Choosing Who to Surround with
01:05:09: Friendship and energy
01:06:10: Thoughts on spirituality
01:09:07: Spirituality and mysticism separation
01:09:33: Contribution and purpose
01:10:42: Resolving the self-interest paradox
01:11:51: Closing remarks