Angel Investing and Taxes [Video]

Welcome to our workshop on Angels and Taxes, a kind of “How to Make a Million Dollars and Pay No Taxes: The Angel Investor’s Guide.” This session will unravel some complexities of angel investing, showing how smart financial strategies can turn a modest investment into substantial tax-free returns. Inspired by Steve Martin’s timeless comedy, this workshop reveals how modern tax laws can actually make the dream of earning a million dollars without paying taxes a reality.
Angel investing is more than just funding startups; it’s about nurturing innovation and being part of the next big thing. We’ll start by exploring the basics of angel investing, from identifying promising startups to understanding the critical role angel investors play in the growth of these ventures. This foundation will set the stage for deeper insights into the significant tax benefits that make angel investing not just rewarding, but also highly efficient from a financial standpoint.
One of the highlights of the workshop is a deep dive into Rule 1202 and Qualified Small Business Stock (QSBS). Imagine investing $50,000 in a startup that skyrockets to a 22x return, resulting in a million-dollar gain. With QSBS, you can exclude up to 100% of your capital gains from taxes, provided you meet certain criteria. This session will guide you through these requirements, using real-world examples to illustrate how you can benefit from this incredible tax provision.
We’ll also compare the benefits of QSBS with those of investing through a Roth IRA, another powerful tool for tax-free growth. While QSBS offers significant advantages for specific types of investments, Roth IRAs provide flexibility and ease of use for a broad range of assets. We’ll break down the pros and cons of each approach, helping you decide which strategy best aligns with your financial goals.
Finally, managing your angel investment portfolio requires a thoughtful approach to risk and return. We’ll share insights for selecting startups, diversifying your investments, and planning your exit strategies. By the end of this workshop, you’ll be equipped with practical knowledge and strategies to maximize your returns while minimizing your tax liabilities. Join us to learn how to make the most of your investments and potentially “make a million dollars and pay no taxes.”

Speakers:

Joseph Tempelberg, Managing Director at Tempelberg & Associates, Ltd., is a distinguished financial executive known for his transformative leadership and expertise in regulatory compliance, including Sarbanes-Oxley (SOX) and the PCAOB Framework. With a focus on startups, private equity, investors, and non-profits, Joseph provides strategic, ethical guidance to navigate complex regulatory landscapes and enhance governance practices. His proven track record at firms like MR Weiser & Co, KPMG, and Healthcare Portfolio and Holdings underscores his ability to simplify intricate problems and deliver pragmatic solutions, making him a trusted partner for fostering long-term success and growth.

Adam Matherly, leader of the Emerging Company & Venture Capital practice at Karr Tuttle Campbell, specializes in transactional business and finance. He represents companies, angel investors, and venture capital funds in private securities offerings. Serving as outside general counsel for emerging companies, Adam assists with business structuring, equity incentive plans, corporate governance, commercial agreements, and M&A. He also advises on intellectual property, including licensing and technology transfer. Formerly, Adam managed his own law firm and served as Vice-President and COO of a client aerospace tooling company, bringing a wealth of practical and legal expertise to his clients.

Peter Weiss brings over forty-five years of finance and managerial experience, including twenty-five years as an investor or owner of growing companies. With a focus on corporate finance and general management, he has served as CFO and advisor to CEOs and Boards of Directors. Peter tailors capital structures and financing plans to match business needs, addressing strategic issues like marketing, sales, and capacity planning. His diverse background as a business owner, professional manager, and investor enables him to align stakeholder goals effectively. A Princeton and Harvard Business School graduate, Peter’s career began on Wall Street and includes consulting for technology, retail, and manufacturing companies. Currently, he advises rapidly growing companies and manages several investment funds and partnerships.