Twin Peaks Wealth Advisors Disclaimer:
Investment advisory services are offered through Twin Peaks Wealth Advisors, a registered investment advisor. The information presented in this article is for general informational and illustrative purposes only and does not constitute personalized investment advice. All opinions expressed are current as of the date of publication and are subject to change. Any references to market or economic conditions are based on information believed to be reliable but are not guaranteed to be accurate or complete. Past performance is not a guarantee of future results.
Additional Disclaimer for Small Exits & Angel Investing and Preparing for Acquisition:
Private placements are for eligible investors. Access to certain venture funds may be available at minimums as mentioned, but this is subject to manager terms. Such investments are illiquid, speculative, and may result in loss of principal.
On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week.
On this episode, Gregory and Paul welcome Tushar Kumar, private wealth advisor and co-founder of Twin Peaks Wealth Advisors. Tushar shares his founder journey, lessons from scaling to $500M AUM, and practical advice for tech professionals navigating equity compensation, IPOs, and acquisitions. The crew also dives (delves) into the hotly debated MIT report claiming 95% of enterprise AI pilots fail, and explores whether AI is creating efficiency—or killing jobs.
️ Episode 012 – Highlights
☕ Cold Brew & Espresso Kicks (0:00)
Gregory and Paul set the Friday vibe, catching up from Brooklyn and talking coffee rituals.
Guest Intro: Tushar Kumar (0:35)
Private wealth advisor and co-founder of Twin Peaks Wealth Advisors, helping tech founders and employees navigate equity, taxes, and wealth strategy.
From Cold Calls to $500M AUM (3:00)
Tushar recounts his entrepreneurial journey—launching during the 2009 financial crisis, cold-calling Cisco engineers, and the grind of building a wealth practice from scratch.
Founders & Concentrated Equity (9:00)
What to do when your net worth is tied up in your startup stock. Tushar breaks down strategies for every stage—from early exercising ISOs to navigating tender offers and IPOs.
Estate Planning & CPA Partnerships (11:30)
The underrated essentials: why every founder needs an estate plan and a sharp CPA long before an exit.
The Biggest Myth in Tech Wealth (14:30)
Tushar debunks the idea that you can “wait until after the exit” to plan. He explains why proactive planning saves millions in taxes and stress.
Quitting Big Tech to Launch a Startup (18:00)
Advice for employees at Google, Meta, or Microsoft who want to take the leap: building guardrails, saving runway, and investing for cash flow.
Small Exits & Angel Investing (22:30)
How to balance reinvesting in your next startup versus diversifying, and why angel bets should be capped at 1–2% of your liquid net worth.
Preparing for Acquisition (31:00)
Five steps every founder should take before selling: option exercise plans, defining “enough,” hiring CPAs, estate docs, and mapping post-exit wealth goals.
MIT Report: 95% of AI Pilots Fail (35:00)
The panel unpacks why AI pilots flop—unwillingness to adopt, fear of job loss, and lack of change management—and whether AI is really displacing jobs.
AI, Jobs & The Future of Work (39:00)
From robots in eldercare to vibe coding at hackathons, the crew debates whether AI is a job killer or the next great productivity unlock.
️ AI Agents & Security Patches (50:00)
Paul explains how parallel AI agents can orchestrate tasks like patching vulnerabilities—radically boosting efficiency in software development.
Meme of the Week (53:40)
“New Jobs AI Will Create in 2025” — Meme lords, deepfake detectives, and automation overlords. The crew agrees: some of these roles are already real.
