Angel Investing: Masterclass

I recently had the pleasure of interviewing David S. Rose, a pioneer angel investor and author of the book "Angel Investing: The Gust Guide to Making Money and Having Fun Investing in Startups" for my podcast. David shared fascinating insights from his decades of experience as an angel investor and entrepreneur.

Here are some of the key takeaways from our discussion:

The Best Way to Get Started in Angel Investing

David believes joining an established angel group is by far the optimal way to begin angel investing. The benefits include:

• Learning from the experience of other angels who can provide mentorship
• Ability to pool checks with other members to make larger, more impactful investments
• Access to vetted deal flow
• Drawing on the expertise of the group for due diligence and company support

While angel groups have some limitations compared to solo angels or VC funds in terms of speed and agility, the advantages they provide in getting an angel career off the ground are substantial.

Business Plans vs. Pitch Decks - What Really Matters

The role of the business plan has evolved. Lengthy written plans are no longer financing documents to secure funding. Instead, they serve as internal roadmaps for the founding team. What investors need to see is proof of execution and traction.

Well-crafted pitch decks of 10-20 slides are usually sufficient for angels to determine if a startup fits their investment thesis and merits a deeper look. The deck should clearly convey what the company does, the problem they solve, their business model, and early progress.

"The biggest problem with new angel investors is they don't have that context. They don't understand really what they're doing. They may understand one particular product, but they don't understand the idea of a company and a startup and how that works." — David S. Rose

Relying on Intuition vs. Data in Early Stage Investing

With very early stage startups, picking winners is extremely difficult, even for the most skilled investors. David believes most angel investors, despite what they may claim, rely heavily on intuition and gut instinct rather than pure data-driven analysis.

The key is to build a large, diverse portfolio in sectors you understand, with founders you believe in. Look for big market opportunities, strong teams, and capital-efficient business models. While most startups will fail, the wins should more than compensate.

The Future of Accelerators and Emerging Tech in Venture Investing

David sees the traditional startup accelerator model pioneered by Y Combinator evolving, with programs like Gust's Mission Control arising as scalable alternatives providing virtual support and access to resources and expertise.

He predicts the emergence of powerful new AI-driven innovations to help investors discover, analyze and manage global startup portfolios. The convergence of AI, blockchain and IoT will be transformative.

"With most angels, despite what they say, despite all the numbers and stuff they give you, it's really intuitive. And so what you can try and do if you're not one of the pickers who has this sort of perfect sense of, and even they still miss 80% of the time, but the question is the other 20%, they get unicorns, right?" —David S. Rose

I hope you found David's hard-earned wisdom and predictions about the future of angel investing as fascinating as I did! You can hear our complete conversation in the latest episode of Startup Istanbul. And I highly recommend picking up a copy of his book, Angel Investing, for a comprehensive guide to succeeding in this challenging but hugely rewarding field.

David S. Rose is a highly accomplished entrepreneur, investor, and author with an impressive track record of founding and funding over 100 pioneering companies. He has been recognized by various media outlets as a key figure in the New York startup scene, earning titles such as "New York's Archangel" (Forbes), "the father of angel investing in New York" (Crain's New York Business), and "patriarch of Silicon Alley" (Red Herring magazine). Rose is also a bestselling author, having written "Angel Investing: The Gust Guide to Making Money & Having Fun Investing in Startups" and "The Startup Checklist: 25 Steps to a Scalable, High-Growth Business."

Throughout his career, Rose has been at the forefront of innovation in various fields, including real estate technology, wireless data information networks, global angel investing platforms, and real estate capital market platforms. He has served as an executive, board member, or investor in numerous companies across diverse sectors such as proptech, fintech, wireless communications, consumer electronics, and many others. Rose is well-known for his ability to discover and mentor high-potential entrepreneurs and is a sought-after speaker, having delivered a popular TEDtalk on pitching to venture capitalists. He is also a frequent lecturer at prestigious business schools and has been recognized as a Top Writer on Quora for his insights on entrepreneurship and investing.