Nick Telson-Sillett: Angel Investing, Being Creative and Getting Wiser

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.

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Timestamps: 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