The vast and intricate tapestry of investments is punctuated by numerous intriguing sectors, each with its own unique charm and potential. Yet, there’s one realm that often stands out, drawing curious glances and ambitious dives: Angel Investing. Named not for its ethereal essence but rather for the nurturing and often critical role its players take on, angel investing is a captivating blend of risk, mentorship, and potential vast rewards.

To the uninitiated, the term ‘angel investor’ might evoke images of celestial beings bestowing startups with golden gifts. In reality, these angels are seasoned individuals or groups who infuse early-stage companies with much-needed capital. They bridge the precarious gap between a startup’s initial idea phase, often funded by friends and family, and the more substantial investments from venture capitalists. Beyond just finances, angel investors often also impart startups with their wisdom, expertise, and a network of influential connections.

The lure of angel investing isn’t just about potentially striking gold with the next tech unicorn or groundbreaking innovation. It’s also about being part of a journey, guiding and nurturing fledgling businesses as they strive to find their footing, scale, and eventually soar. For those with an entrepreneurial spirit, the world of angel investing offers an opportunity to be intimately involved in the early stages of potential industry game-changers.

Note: This is my sixth blog post of ten over the next ten weeks or so, in my current series called “Advanced Financial Insights For The Entrepreneur.”

What qualifies me to write this series? After getting my MBA in Finance in 1997, I worked for several top-tier investment banks over the next 15 years. These included stints of increasing responsibilities at Goldman Sachs, Bank of America, Citigroup, and JP Morgan. Additionally, I am the founder of Sugarloaf Capital Group, a hedge fund with advanced quantitative strategies for wealthy families.

Both Sugarloaf Capital Group and Memory Fortress (my current company) received angel investor funding to get them started.

I have fairly deep knowledge and experience in all of the blog topics in this current series. Let’s dive in and learn about angel investing!

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What is Angel Investing?

In the vast realm of investment strategies and options, angel investing occupies a special niche that’s both alluring and mystifying to many. At its essence, angel investing is the act of providing capital to early-stage startups in exchange for ownership equity or convertible debt. However, this rudimentary definition hardly captures the full spectrum of relationships, risks, and rewards that encapsulate the angel investment ecosystem.

The Basics of Angel Investing

Angel investors are typically affluent individuals who provide funding for a startup, often in its nascent stages, in return for a stake in the company. The term “angel” originates from Broadway, where wealthy patrons generously funded theatrical productions. In the world of startups, these “angels” provide the financial lifeline needed to transform innovative ideas into viable businesses.

The critical distinction between angel investors and venture capitalists lies in the stage of investment and the amount involved. While venture capitalists manage pooled funds from various investors to invest in startups and small businesses, angel investors use their personal funds. Angel investments typically precede venture capital funding and follow the initial “friends and family” round, making them a crucial bridge in the funding lifecycle of a startup.

The Relationship Dynamics

The allure of angel investing isn’t merely about financial returns. Angel investors often take an active role in the startup, offering mentorship, guidance, and access to their networks. This symbiotic relationship can be invaluable for startups, as the expertise and connections brought by an angel can often be as crucial as the financial investment itself.

A Real-world Example: WhatsApp and Brian Acton

To understand the transformative power of angel investing, one need not look further than the story of WhatsApp and one of its co-founders, Brian Acton. Before WhatsApp became a global sensation and was acquired by Facebook for a staggering $19 billion, it was a fledgling startup in need of funds.

In 2009, when WhatsApp was in its infancy, five ex-Yahoo! friends invested $250,000 in seed funding. This group of friends, led by Brian Acton, didn’t just provide capital. They also became early users, promoters, and advisors for the app. Their belief in the potential of the platform and their willingness to invest at such an early stage is a textbook example of angel investing.

The initial boost provided by this angel investment helped WhatsApp navigate its early challenges, refine its offering, and scale to a point where it caught the attention of larger investors and eventually tech giants like Facebook. Those initial angel investors saw a return that was exponentially higher than their initial investment, illustrating the potential high-reward nature of angel investing.

WhatsApp’s story is an inspiring one, but it’s essential to note that the world of startups is fraught with risks. Many startups fail to gain traction and fold before they can return any investment. This inherent risk makes angel investing a high-stakes game, where due diligence, patience, and a keen understanding of the market are paramount.


Angel investing is a fascinating blend of finance, mentorship, and entrepreneurship. It’s about believing in a vision when it’s just a spark and providing not only the capital but also the wind to fan that spark into a flame. While the potential rewards can be immense, as the WhatsApp example illustrates, the risks are also significant. However, for those with the passion, insight, and resources to support the next generation of innovators and disruptors, angel investing offers an unmatched journey into the heart of entrepreneurship.

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Who Can Become an Angel Investor?

In the intricate web of startup ecosystems, angel investors play a pivotal role, often serving as the lifeline for fledgling companies on the cusp of explosive growth. Their strategic investments can mean the difference between a startup’s failure and its ascension to industry stardom. But who exactly are these angels, and can anyone join their ranks? The answer is both simple and nuanced.

Criteria for Angel Investors

While anyone with spare capital might theoretically be able to make an investment in a startup, there are legal and practical criteria that define an angel investor.

In many countries, including the U.S., regulatory bodies set certain financial benchmarks to qualify as an “accredited investor.” In the context of the U.S., the Securities and Exchange Commission (SEC) outlines that an accredited investor should have:

  • An annual income exceeding $200,000 (or $300,000 combined with a spouse) for the last two years, with the expectation of the same or higher income in the upcoming year.
  • A net worth surpassing $1 million, either individually or jointly with a spouse, excluding the primary residence’s value.

These benchmarks are set to ensure that the investor has the financial resilience to withstand potential losses, given that startups, by their very nature, are high-risk endeavors.

The Power of Crowdfunding

While the traditional angel investor might be an affluent individual with substantial financial clout, the advent of crowdfunding platforms has democratized the process, allowing a broader demographic to get involved in startup investments. Websites like Kickstarter, SeedInvest, and Indiegogo have provided avenues for everyday individuals to support and invest in startups, often for as little as a few hundred dollars.

For instance, Oculus VR, the company behind the Oculus Rift virtual reality headset, initially sought crowdfunding on Kickstarter. Backers could pledge varying amounts, and while these early supporters weren’t traditional angel investors, they played a pivotal role in the company’s initial success. When Facebook acquired Oculus VR for about $2 billion, those early supporters witnessed firsthand the power of backing early-stage companies.

Beyond Financial Criteria: The Intangibles

While financial benchmarks are critical, successful angel investing isn’t solely about having deep pockets. A true angel investor brings more to the table:

  1. Experience & Expertise: Many angel investors have entrepreneurial backgrounds themselves. Their experiences, successes, and even failures can offer invaluable guidance to startups. For example, Peter Thiel, co-founder of PayPal, made an early angel investment of $500,000 in Facebook. His background in fintech and his entrepreneurial journey brought more than just money to the young social media company.

  2. Network & Connections: The right introduction can catapult a startup to new heights. Seasoned angel investors often have extensive networks, and their endorsement can open doors that might otherwise remain closed.

  3. Passion & Belief: Angel investing isn’t a passive act. The most impactful angel investors are those who genuinely believe in the vision and mission of the startups they support. They’re not just investing in a potential financial return but in a future they want to see realized.


So, who can become an angel investor? While financial criteria provide a baseline, the world of angel investing is evolving, with platforms and opportunities allowing a wider swath of people to engage with and support early-stage companies. At its heart, angel investing is about more than capital; it’s about vision, mentorship, and the unwavering belief in the potential of nascent ideas. Whether you’re an accredited investor with millions to spare or an enthusiast with a few hundred dollars and a dream, there’s a place for you in the exciting realm of angel investing.

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Why Become an Angel Investor?

The journey of entrepreneurship, with its promise of innovation and disruption, has a magnetic allure that draws many. But for those who wish to engage with this world without founding a startup themselves, angel investing offers a unique vantage point. By becoming angel investors, individuals have the chance to be part of the entrepreneurial narrative, playing a crucial role in shaping the future of industries and even societies. So, why exactly should one consider stepping into the shoes of an angel investor?

1. Financial Returns

At its core, investing is about realizing a return on one’s capital. Angel investing, when done right, can offer substantial returns. Early-stage startups, by their nature, come with high risks. However, the potential rewards can be just as high, if not higher. A strategic investment in a startup that eventually goes on to be a major success can yield returns multiple times the initial investment. Consider Chris Sacca’s early investment in Twitter, which helped him amass a fortune, or the early backers of companies like Uber and Airbnb, who saw exponential growth in their stakes.

2. Diversifying Investment Portfolio

The investment mantra of not putting all one’s eggs in a single basket holds. While stocks, bonds, and real estate are standard avenues for many investors, startups provide a unique asset class. They offer diversification, which can be particularly valuable in volatile economic conditions. A balanced portfolio that includes high-risk, high-reward assets like startups, alongside more stable investments, can optimize returns and mitigate overall risks.

3. Fostering Innovation and Driving Change

Angel investors often get a front-row seat to innovation. By funding startups, they’re not just placing bets on companies but on ideas, technologies, and visions that have the potential to revolutionize industries. For those passionate about particular fields or societal challenges, angel investing allows them to directly support and accelerate solutions. For instance, an individual passionate about sustainable energy might choose to back startups working on cutting-edge renewable technologies, driving both sectoral growth and societal change.

4. Mentorship and Personal Growth

Many angel investors are seasoned professionals or entrepreneurs themselves. Their journey into angel investing offers a dual benefit. On one hand, startups gain from the investor’s experience, mentorship, and network. On the other, investors often find that guiding startups becomes a source of personal and professional growth. Engaging with young, dynamic teams, grappling with market challenges, and navigating the startup landscape can offer fresh perspectives and refine one’s entrepreneurial acumen.

5. Building a Legacy

Beyond the immediate financial gains, angel investing offers individuals a chance to build a lasting legacy. By supporting and nurturing startups, investors contribute to job creation, industry growth, and potentially even societal shifts. Their early backing of game-changing companies ensures their place in the annals of business history. Think of the early backers of Apple or Google – today, they’re not just remembered for their foresight in recognizing potential but also for their role in creating tech behemoths that have defined a generation.

6. Expanding Networks and Horizons

The startup ecosystem is vibrant, diverse, and global. Engaging as an angel investor allows individuals to expand their networks, connecting with other investors, industry leaders, and innovators from varied fields. These interactions can lead to new investment opportunities, partnerships, and even business ventures, making the investment landscape much more dynamic.


To become an angel investor is to embrace risk with the hope of reward, to engage deeply with the tapestry of innovation, and to play a tangible role in sculpting the future. It’s not just about capital but about curiosity, vision, and the thrill of the entrepreneurial journey. While the risks are undeniable, the potential rewards – both tangible and intangible – make angel investing a compelling avenue for those looking to merge finance with passion.

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Risks in Angel Investing

Angel investing, with its tales of massive returns and game-changing startups, paints an enticing picture. However, the world of startup investing is not just glittering successes; it’s also riddled with complexities and potential pitfalls. Every aspiring angel investor should approach this arena with eyes wide open, fully aware of the risks involved. Let’s delve deeper into the primary risks and considerations in angel investing, punctuated with illustrative examples.

1. High Failure Rate

The most daunting risk in angel investing is the inherent unpredictability of startups. The sobering reality is that many startups, even those with promising beginnings, don’t reach maturity.

Example: Juicero, a tech-driven juicing machine startup, serves as a classic cautionary tale. Despite securing over $100 million from investors amid substantial hype, the company shuttered within 16 months of launching its product. This story underlines that ample funding doesn’t necessarily equate to long-term success.

2. Illiquidity

A crucial aspect of angel investments is their illiquid nature. Once committed, your funds are generally tied up in the startup, accessible only through specific exit events like acquisitions or IPOs.

Example: Consider the trajectory of Airbnb. Angel investors in the platform were locked into their investments for over a decade before the company’s eventual IPO in 2020. Although many early backers reaped considerable returns, this case underscores the importance of a long-term perspective in angel investing.

3. Dilution

As startups progress through funding rounds, the stakes of early investors can get diluted if they don’t invest additional funds to maintain their shares.

Example: Imagine an investor who acquires a 10% stake in a budding startup. As the company undergoes subsequent funding rounds, and if the angel chooses not to reinvest, their stake might diminish to a mere 2-3%.

4. Lack of Control

Holding equity doesn’t necessarily grant control. Angel investors often have minimal influence over daily operations or significant company decisions, which can become problematic if the company’s trajectory deviates from initial projections.

Example: When Yahoo decided to acquire in 1999, the early investors had minimal influence over this pivotal decision. While they enjoyed a lucrative payout, the long-term aspirations for were sidelined as Yahoo eventually discontinued the service.

5. Market Volatility and External Factors

External market dynamics, including economic fluctuations, regulatory upheavals, or global crises, can dramatically alter a startup’s prospects.

Example: The repercussions of the COVID-19 pandemic serve as a stark reminder. Even promising startups in travel and hospitality, such as Oyo Rooms, grappled with unprecedented challenges due to collapsing demand.

6. Overvaluation

In dynamic startup ecosystems, there’s an ever-present danger of overvaluation, leading investors to pay more than a company’s intrinsic worth.

Example: Theranos, once lauded as a revolutionary force in medical testing and boasting a valuation of $9 billion, faced a catastrophic fall from grace. When revelations emerged that its acclaimed technology was flawed, the company’s valuation tanked, leaving investors with massive losses.

7. Emotional Decision-making

Objective analysis is the bedrock of angel investing. Yet, there’s a looming risk of decisions being clouded by emotions or personal ties.

Example: An investor might feel compelled to support a startup due to close ties with the founding team. If due diligence is sidestepped in favor of personal connections, and the startup falters, the fallout could extend beyond financial losses, potentially straining personal relationships.

8. Competitive Landscape Changes

The business landscape is ever-evolving, with new competitors and technologies emerging constantly. A startup that seems unique today might face stiff competition tomorrow.

Example: Remember the rise of Blockbuster? At its peak, it seemed invincible. However, with the advent of digital streaming services like Netflix, Blockbuster’s traditional model became obsolete, leading to its eventual decline.

9. Technological Redundancy

In a rapidly advancing technological age, there’s always a risk of a startup’s product or service becoming redundant or outdated.

Example: Think of early social media platforms like MySpace, which, despite its initial popularity, was overshadowed by more advanced platforms like Facebook.

10. Regulatory and Legal Hurdles

Startups, especially those in cutting-edge sectors, might face unforeseen regulatory challenges.

Example: Uber, the ride-sharing giant, has faced regulatory hurdles in numerous cities worldwide. These challenges, often unforeseen during initial investments, can impact a company’s growth trajectory and profitability.

11. Prolonged Time to Exit

The exit strategy for an angel investor, be it through an acquisition, merger, or Initial Public Offering (IPO), can take longer than anticipated. Startups, in their nascent stages, might face numerous roadblocks before achieving a state conducive for a profitable exit.

Example: The well-known messaging app, WhatsApp, founded in 2009, was acquired by Facebook only in 2014. While this five-year period might seem swift in the startup world, for many investors, especially those used to liquid markets, this can feel like an eternity.

12. Evolving Business Models

A startup may pivot from its original business model, leading to an entirely different trajectory than what was initially pitched to investors.

Example: Slack, today known as a leading workplace communication tool, started as a gaming company called Tiny Speck. Investors who initially backed Tiny Speck had to adapt their expectations and trust the company’s pivot into the communication realm.

13. Dependence on Key Personnel

Startups often depend heavily on their founding team or key personnel. A change in this core team can impact the direction and success of the company.

Example: When Steve Jobs initially left Apple in 1985, the company struggled in his absence. His return in 1997 was pivotal in driving Apple to the tech giant status it enjoys today. Angel investors need to be aware of the impact that such key figures can have on their investments.

14. Market Size Overestimation

Startups can sometimes overestimate their target market size, leading to over-optimistic projections and potential future disappointments.

Example: The Segway, while revolutionary in its design, had limited market appeal, mainly due to its price point and regulations surrounding its use in public spaces. The initial buzz and high expectations were tempered by the realization of its niche appeal.


The world of angel investing is as challenging as it is rewarding. Potential pitfalls lurk at every corner, but so do opportunities for remarkable success stories. By acknowledging the risks, conducting comprehensive due diligence, and maintaining a balanced perspective, angel investors can not only mitigate potential setbacks but also identify and seize the most promising opportunities. After all, in the words of Peter Drucker, “Whenever you see a successful business, someone once made a courageous decision.” The same can be said for successful investments. The path to success in angel investing is paved with informed decisions, unwavering patience, and, sometimes, a touch of daring courage.

Attracting Capital from Angel Investors

As an entrepreneur, securing the right funding can be the difference between scaling your business dream or watching it languish in obscurity. Angel investors, often affluent individuals keen on backing promising startups, can offer not just capital but also experience, mentorship, and access to a broader network. So, how do you attract these crucial backers to fuel your vision? Here’s a roadmap to help you make an indelible impression on potential angel investors:

1. Craft a Compelling Narrative

Your startup isn’t just a business; it’s a story. A unique narrative, articulated clearly and passionately, can resonate deeply with potential investors. It’s about painting a vivid picture of the problem you’re solving, how your solution stands out, and where you see yourself in the future.

Example: Airbnb’s narrative revolved around the idea of not just finding a place to stay, but ‘belonging’ anywhere in the world. This emotional connection amplified its business proposition.

2. Build a Solid Business Model

While ideas are crucial, a tangible business model is imperative. Angel investors seek assurance that your startup can generate returns. This means showcasing clear paths to revenue, viable customer acquisition strategies, and a sustainable competitive advantage.

Example: Dropbox initially used a freemium model, offering free storage space but charging users for additional capacity. This straightforward model demonstrated clear revenue potential.

3. Demonstrate Traction

Nothing speaks louder than results. Whether it’s a growing user base, increasing sales, or notable partnerships, demonstrating traction can instill confidence in potential investors. It’s evidence that there’s genuine demand for your offering.

Example: If your mobile app has achieved 50,000 downloads in its first three months with minimal marketing spend, it’s a potent indicator of its organic appeal.

4. Assemble a Stellar Team

Startups are as much about people as they are about ideas. Showcasing a team that has the right blend of skills, experience, and passion can be a major draw for investors. They’re investing in your collective ability to execute the vision.

Example: If you’re building a fintech startup and your team comprises individuals with deep experience in finance, tech, and regulatory compliance, it reinforces your startup’s credibility.

5. Be Transparent About Risks

While highlighting your achievements and potential is vital, being candid about the challenges and risks you foresee can enhance your trustworthiness. It shows you’re realistic, and it allows potential investors to assess if they’re the right fit to help you navigate those challenges.

Example: A health tech startup might acknowledge regulatory challenges in different markets but can position this as an opportunity for investors with the right connections to add value.

6. Cultivate a Network

Before seeking capital, invest time in cultivating relationships within the startup and investor community. Attend events, seek mentorships, and engage on platforms tailored for startups and investors, like AngelList or SeedInvest.

Example: Through platforms like Meetup, entrepreneurs can find local events where they can pitch their startups, practice their pitch, and get feedback.

7. Personalize Your Pitch

Every angel investor is different, with varying interests, expertise, and investment philosophies. Tailoring your pitch to resonate with a specific investor’s interests can set you apart. Do your research. Understand their past investments, sectors of interest, and investment criteria.

Example: If pitching to an angel who has extensively invested in sustainable enterprises, emphasize your startup’s environmental impact and sustainability goals.

8. Clearly Define the Use of Funds

When seeking investment, be crystal clear about how you intend to use the capital. Whether it’s for product development, marketing, hiring, or expansion, providing a detailed breakdown assures investors of your strategic intent.

Example: If seeking $500,000, provide a detailed allocation, like $200,000 for product development, $150,000 for marketing, and so on.


Attracting angel investment is as much an art as it is a science. It’s about building genuine relationships, exuding credibility, and showcasing both your vision and pragmatism. As you embark on this journey, remember that every rejection, every piece of feedback is a step closer to refining your proposition and aligning with the perfect investor who shares your dream.

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How to Get Started in Angel Investing

Venturing into the realm of angel investing is a thrilling prospect, filled with opportunities to fund the next big thing and potentially reap significant returns. But like any investment, it requires careful planning, research, and a strategic approach. If you’re contemplating dipping your toes into the world of angel investing, here’s a step-by-step guide to ensure you embark on this journey equipped with the knowledge and insight needed for success.

1. Understand Your Motivation

Why do you want to become an angel investor? This introspection is vital. Some are driven by a desire to contribute to the entrepreneurial ecosystem, while others see it as a financial opportunity. It could also be a mix of both. Define your motivations as this will shape your investment strategy.

Example: If you’re an entrepreneur at heart, passionate about green energy, you might specifically look for startups in the renewable sector, aligning your investment with your personal passions.

2. Educate Yourself

Knowledge is power, especially in the intricate world of startup investing. Several courses, webinars, and workshops are available on platforms like Udemy, Coursera, and even specialized institutions. Reading books about venture capital and angel investing, or following prominent angel investors’ blogs, can also provide valuable insights.

Example: “Angel: How to Invest in Technology Startups” by Jason Calacanis provides a firsthand perspective of the nuances of angel investing.

3. Determine Your Investment Budget

Decide on how much capital you’re willing to invest and the portion of that sum you’re willing to risk on each startup. Given the high-risk nature of startups, it’s advised that angel investments should only be a fraction of your overall investment portfolio.

Example: If you have a total investment budget of $200,000, you might allocate 10% ($20,000) to angel investing, and further divide this sum across multiple startups to diversify risk.

4. Network Actively

The best deals often come through referrals and trusted networks. Joining angel investing groups, attending startup events, or engaging with incubators can expose you to promising opportunities. Platforms like AngelList also facilitate connections between startups and potential investors.

Example: Techstars, a renowned startup accelerator, regularly hosts demo days where investors can interact with emerging startups from its cohorts.

5. Conduct Thorough Due Diligence

Before committing to any investment, delve deep into the startup’s business model, market potential, competitive landscape, financials, and the founding team’s credentials. Engaging with the founders to understand their vision and strategy can provide invaluable insights.

Example: When considering an investment in a health tech startup, explore the regulatory environment, potential patent issues, and the scientific validity of the technology they’re promoting.

6. Scrutinize Before You Commit

Once a potential investment opportunity is on the horizon, conduct thorough due diligence. Examine the startup’s business model, market potential, competitive landscape, team, and financial projections. Meeting founders and understanding their vision and strategy is crucial.

Example: If evaluating an e-commerce startup, assess market trends, understand their unique value proposition, and examine customer reviews and feedback.

7. Understand Terms and Valuations

The world of angel investing has its language. Familiarize yourself with terms like equity, convertible notes, valuation caps, and liquidation preferences. Ensure that the terms are fair and that you’re comfortable with the startup’s valuation.

Example: If a tech startup is valued at $5 million and you invest $50,000, you’ll own 1% of the company. Ensure this valuation aligns with market norms and the startup’s potential.

8. Mentoring Matters

Angel investing isn’t just about funding. Offering your expertise, mentorship, or industry connections can be invaluable for startups. This active involvement can also provide you with deeper insights into the company’s operations and progress.

Example: If you have a background in digital marketing, guiding a startup in their marketing strategy can not only enhance their growth but also protect and grow your investment.


Angel investing offers an exhilarating blend of high risks and potentially high rewards. While it’s not suitable for everyone, for those willing to put in the time, effort, and capital, it offers a unique opportunity to be a part of groundbreaking innovations and the next big thing in the world of business.

Remember, as with all investments, it’s essential to do your due diligence and understand that past success is not indicative of future results. The world of angel investing is not just about capital; it’s about passion, vision, and the thrilling journey of entrepreneurship. Welcome to the celestial world of angels!

In a previous life, Keith Osbon worked for 14 years on Wall Street with Goldman Sachs, JP Morgan, and Morgan Stanley. He has been involved with angel investing since the early 2000s, and his current company Memory Fortress received an angel round of funding in 2014.

Keith is currently raising additional capital for SANAS and Memory Fortress at the time of this writing.

Keith Osbon
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