As a product builder, she’s delivered nearly $1B in V1 products to market. As a founder, she’s raised $20M in VC for her own companies and worked 1:1 with 200 other early-stage entrepreneurs. As a funder, she’s a loud and proud baby-check writer who has invested in nearly 50 startups using the funds in her IRA. Now, she is bringing all of these experiences together and Taylor-Swifting the angel economy with her latest venture, Play Money.
Now, she's focused on angel investing which she believes in undergoing a revolution. Once perceived as the exclusive playground of ultra-wealthy individuals and venture capital insiders, the barriers to entry are now lower than ever. And, Cheryl is at the forefront of this movement, advocating for a more inclusive and accessible approach. Her perspective challenges outdated notions and provides a roadmap for individuals eager to fund innovation and make a difference. Here’s how aspiring angels can start small, diversify smartly, and use accessible strategies to build meaningful portfolios.
The mystique surrounding angel investing often deters newcomers, but Kellond is determined to dispel the myths. Many believe they need to write six-figure checks or possess intricate knowledge of venture finance to participate. Kellond, however, emphasizes that "baby checks" — investments ranging from $1,500 to $25,000 — are not only acceptable but can also be transformative.
Intuition plays a key role, especially in early-stage investing. At this level, startups often lack extensive data, which means angels are on relatively equal footing with institutional investors. The most critical factors to evaluate are the size of the problem being addressed and the resilience of the team tackling it. "You’re already a better angel than you know," Kellond assures, pointing to decades of lived experience that give potential investors an edge.
For those intimidated by industry jargon such as "SAFE notes" or "SPVs," she offers reassurance. The resources to learn are abundant, from AI tools to platforms like hers that provide educational support. The real key is starting, even with a small investment, and letting experience build confidence over time.
Angel investing is a numbers game. Success lies in diversification, not in finding a single unicorn. According to Kellond, the best strategy is to build a portfolio of at least 30 startups over several years. This approach minimizes risk while maximizing the chance of discovering outliers—the rare companies that deliver extraordinary returns.
Data backs up this philosophy. Studies of early-stage portfolios reveal that 50% of startups fail entirely, while only a small fraction deliver returns of 10x or more. However, a well-diversified portfolio significantly increases the likelihood of capturing these outliers. Kellond likens this strategy to investing in index funds: "It’s less about picking winners and more about taking enough shots on goal."
She also encourages patience. Early losses in angel investing—known as the J-curve effect—are common, as failures typically surface within three to five years, while big winners take much longer to mature. Maintaining a long-term perspective is essential.
Kellond’s philosophy centers on making angel investing accessible to more people, particularly women and underrepresented groups. She emphasizes that you don’t need millions in disposable income to get started; you just need to think creatively about your resources.
One of her favorite strategies is tapping into overlooked sources of capital, such as Individual Retirement Accounts (IRAs). Many investors are unaware that specialized custodians can allow IRA funds to be used for startup investments. For individuals who are self-employed or have solo 401(k)s, this can unlock significant capital without affecting day-to-day budgets.
Additionally, she encourages leveraging syndicates or Special Purpose Vehicles (SPVs). These structures pool smaller checks from multiple investors, allowing them to collectively fund startups without overloading the founder’s cap table. For those hesitant to go it alone, platforms like Kellond’s Play Money offer curated deal flows and community-driven support, making it easier to start and learn without turning investing into a full-time job.
Finally, Kellond suggests reframing angel investing as more than just financial participation. She often draws from personal development, philanthropy, and activism budgets to support startups she’s passionate about. This approach not only diversifies her financial portfolio but also aligns with her values and interests.
Angel investing isn’t just about potential financial returns; it’s about shaping the future of innovation and wealth creation. Kellond challenges those who are accredited investors to set aside even modest sums annually. If more individuals take this step, the collective impact could unlock billions in capital for entrepreneurs who are solving critical problems.
The barriers to angel investing are lower than ever. Whether through small checks, diversified portfolios, or creative funding strategies, this new era of angel investing empowers more people to join the game—and change it. As Kellond puts it, "You don’t get the chance to be a great angel unless you write the first check."
