Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups.

When most people think about Oprah Winfrey investments, they picture her famous Weight Watchers deal. But here's what they miss: that investment wasn't luck. It was the result of a systematic approach to investing that most early-stage investors completely ignore.

I've been digging into Oprah's investment strategy, and there are some lessons here that every angel investor needs to understand. Because while we're all chasing the next AI unicorn, Oprah has been quietly building a portfolio that actually makes sense.

The Weight Watchers Masterclass (And What It Really Teaches Us)

Let's start with the obvious one. In October 2015, Oprah bought 6.4 million shares at $6.79 a share, investing $43.2 million for a 10% stake in Weight Watchers.

The stock more than doubled immediately after the announcement. By 2018, her investment was worth more than $400 million. She eventually cashed out $221 million in net profits before stepping down from the board in 2024.

But here's what most people miss about this deal: Oprah didn't just write a check. She became the face of the brand. She joined the board. She made Weight Watchers her personal mission.

This wasn't passive investing. This was active partnership.

The lesson: Stop thinking like a check writer. Start thinking like a business partner.

The Real Pattern: Mission-Driven Investments

Looking at Oprah's broader portfolio, there's a clear pattern that most investors completely overlook. Through her family office OW Management (established in 2010), she's made strategic investments in True Food Kitchen, Apeel Sciences, Oatly, Maven Clinic, and Guild Education.

Notice something? These aren't random bets on hot sectors. They're all aligned with causes she actually cares about: health, sustainability, education, and equity.

True Food Kitchen: The Health Play: In 2018, Oprah led True Food Kitchen's venture round after being introduced to the healthy restaurant chain by her fitness expert Bob Greene. She didn't just invest - she joined the board and actively collaborated with leadership on business and marketing strategy.

The result? A restaurant chain that's now expanding nationwide, with Oprah's endorsement driving both brand credibility and customer acquisition.

Apeel Sciences: The Sustainability Bet: Here's where it gets interesting. In 2020, Oprah and Katy Perry invested in Apeel Sciences' $250 million round, which creates edible coatings that extend the shelf life of produce by 2-3x.

"I hate to see food wasted, when there are so many people in the world who are going without," Winfrey said about the investment.

This wasn't about riding a climate tech wave. This was about solving a problem she genuinely cared about. Food waste costs the United States $218 billion annually, and Apeel's solution directly addresses that.

Maven Clinic: The Equity Investment: Oprah backed Maven Clinic's $110 million Series D in 2020, helping the women's health startup reach unicorn status at a $1.7 billion valuation.

Again, this wasn't about chasing the hot healthtech sector. Maven covers about 17 million lives through its contracts with health plans and employers, including companies like Amazon, Microsoft and AT&T.

The pattern holds: mission-driven investment in a space she understands and cares about.

The Family Office Approach Most Angels Ignore

Here's what separates Oprah from typical angel investors: she treats investing like a business, not a hobby.

Her family office, OW Management, is a 10-employee organization based in West Hollywood with a dedicated managing director and investment committee. They don't spray and pray. They don't chase trends.

Instead, they focus on three core areas:

1. Media and Entertainment (her core expertise)

‍2. Health and Wellness (personal passion)

‍3. Education and Social Impact (mission alignment)

About 20% of their time is spent handling existing investment-portfolio matters, including overseeing fund managers, reviewing asset exposures, and evaluating the drivers of investment returns.

This is professional-grade wealth management, not weekend angel investing.

The Oatly Lesson: Brand Power Creates Returns

In July 2020, Oprah joined Natalie Portman, Jay-Z, and former Starbucks CEO Howard Schultz in investing in Oatly's $200 million private equity round, valuing the Swedish oat milk company at $2 billion.

But here's the key insight: Oprah promotes veganism and has shown particular interest in the health and wellness sector. This wasn't a random food tech bet. It was strategic alignment with her personal brand and values.

When Oatly went public in 2021, it had an initial valuation of $10 billion. Not bad for a company that makes milk from oats.

What Early-Stage Investors Get Wrong

Most angels approach investing backwards. They start with what's hot, then try to find deals in that space. Oprah does the opposite: she starts with what she knows and cares about, then finds the best companies in those areas.

Here's how to think about it:

Wrong Approach:

• AI is hot → Find AI companies to invest in → Hope for returns

Right Approach:

• I understand this problem → Find companies solving it well → Use my expertise to help them succeed

The difference is expertise-driven investing vs. trend-driven investing.

The Guild Education Play: Long-Term Thinking

In 2022, Oprah participated in Guild Education's $175 million Series F at a $4.4 billion valuation. Guild focuses on upskilling frontline employees through online education.

"I believe deeply in the power of education to change the trajectory of a person's life, and Guild is creating a more equitable path to quality education," Oprah said.

This investment perfectly illustrates her approach: find companies that align with your values AND have massive market potential.

Guild isn't just an edtech company. It's addressing the fundamental challenge of workforce development in America. That's a problem Oprah understands deeply, and one she's uniquely positioned to help solve.

The Portfolio Construction Strategy

Looking at Oprah's approach, there are three key principles:

1. Stay in Your LaneEvery investment connects to media, health, education, or social impact. She doesn't chase crypto or fintech because those aren't her areas of expertise.

2. Add Value Beyond CapitalWhether it's brand endorsement, board participation, or strategic advice, Oprah brings more than money to every deal.

3. Think in Decades, Not YearsHer CIO describes her as having "a lower risk tolerance" compared to more aggressive investors. She's building generational wealth, not looking for quick flips.

The Real Lesson for Angel Investors

Here's what Oprah's investment strategy teaches us: the best returns come from investing in what you know, with companies you can actually help.

Most early-stage investors treat angel investing like playing the lottery. Write small checks across dozens of companies and hope something hits big.

Oprah treats it like building a business. Make fewer, larger bets in areas where you have unfair advantages. Then actively work to make those companies successful.

The tactical takeaways:

1. Define your thesis early. What sectors do you understand? What problems do you care about solving?
2. Build real relationships. Don't just write checks. Join boards. Make introductions. Use your expertise.
3. Stay disciplined. It's easier to chase hot deals than to stick to your strategy. Do the harder thing.
4. Think long-term. The best returns come from companies you help build over decades, not quick exits.

The Oprah approach isn't glamorous. It doesn't involve AI or crypto or whatever's trending on Twitter. But it works.

If you're looking to connect with other early-stage investors who share this philosophy of being genuinely helpful to founders rather than just writing checks, Angel Squad brings together operators-turned-angels who understand that the best returns come from building real relationships with the companies you back.

And in a world where most angels lose money, "it works" is exactly what we should be optimizing for.