Sriram Gollapalli: Exited Tech Founder Who Loves Investing

Mar 28, 2024

Sriram Gollapalli, an exited tech founder turned investor, reflects on his post-exit journey, including estate planning and angel investing. He shares insights on life after selling his business, managing time, and the challenges of transitioning from founder to employee. Sriram also discusses his motivation for starting a new business and the growth of his Longangle community.

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Introduction

00:00 • 2min

Navigating Post-Exit Emotional and Financial Realities

01:46 • 5min

Exploring Creativity and Motivation in Entrepreneurship

07:11 • 2min

Entrepreneurial Journey: From Diamonds to Diapers

09:06 • 2min

From Corporate to Personal Finance to Angel Investing: A Journey of Financial Exploration

11:05 • 12min

Exploring Diversified Investment Strategies

23:17 • 16min

Reflections on Post-Exit Experience

39:32 • 18min

Sriram Gollapalli. After selling his software as a service business 8 years ago, he spent 6 years working with an acquirer before embracing his new found freedom. His calling? Investing and fostering a community of like minded investors. This episode delves into Sriram’s post exit journey. Including an introspection retreat, angel investing and the challenges of estate planning.

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Timestamps: 00:00:00: Intro 00:01:10: Welcome 00:01:19: Discussion about the sale of ILab's operation system 00:01:37: Discussion about the treatment of staff post-sale 00:01:46: Discussion about the bootstrapping process 00:01:56: Discussion about life post-exit 00:02:09: Reflection on change post-exit 00:03:01: Discussion about the financial aspects post-exit 00:03:12: Discussion about managing time after selling the business 00:03:57: Discussion about how the exit was structured 00:05:10: Discussion about joining the buyer 00:05:34: Reflection on being an employee post-exit 00:06:28: Discussion about running operations for iLabs 00:07:10: Discussion about being a creative person 00:07:39: Discussion about motivations for starting a new business 00:09:14: Reflection on the entrepreneurial journey 00:09:19: Discussion about the creation of the Longangle community 00:10:31: Discussion about the growth of the Longangle community 00:11:01: Reflection on what Longangle gives to the founder 00:13:00: Discussion on angel investing 00:18:33: Reflection on angel investing as a financial strategy 00:19:46: Reflection on time spent on angel investing 00:20:09: The Balance of Time: Mentoring, Deal Flow Sourcing, and Personal Life 00:20:29: After Exit Stage: Opportunities and Challenges 00:21:46: The Unexpected Time Investment in Startups 00:22:04: The Impact and Limitations of Being an Angel Investor 00:22:25: The Long Game of Angel Investing and the Consequences of Fundraising 00:23:16: Investment Outside of Angel Investing 00:24:37: Diversification of Portfolio: Real Estate and Broad-based Indices 00:25:11: The Desire for Simplification in Investments 00:28:19: Community Involvement: Engaging in the DC Tech Scene 00:28:58: Entrepreneurship Education for the Younger Generation 00:29:20: The Concept of "Ikigai": Defining Purpose and Intention 00:30:48: Aspirations for the Future: The Drive for Building 00:33:04: The Influence of Wealth on Time Allocation 00:34:17: Reflective and Introspective Retreats 00:36:36: The Impact and Responsibility of Wealth 00:38:17: Regrets and Reflections on Selling a Business 00:39:37: Post-Exit Mental Health: The Need for Therapy 00:41:31: Consequences of quitting and firing 00:42:32: Thoughts on Spirituality and Culture 00:44:06: Personal Growth Strategy 00:45:16: Advice for business sellers 00:49:36: Importance of Health 00:50:35: How fulfilled are you? 00:52:43: Surrounding oneself with the right people 00:55:26: Recreational activities and building networks 00:55:57: Legacy and How to be remembered