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.

Most venture capitalists follow the same playbook: raise money from wealthy individuals and institutions, then invest in companies that look like previous winners. Alexis Ohanian threw that playbook out the window.

After co-founding Reddit and selling it 18 months later, Ohanian could have taken the traditional path into venture capital. Instead, he built something completely different: Seven Seven Six (776), a "technology company that deploys venture capital" with nearly $1 billion under management and an investor base that's 50% women and 15% Black and Indigenous people.

Here's how the guy who helped create "the front page of the internet" is now rebuilding venture capital from the ground up.

From Reddit to Venture Capital: The Unlikely Journey

Let's start with the foundation. Ohanian co-founded Reddit in 2005 with Steve Huffman as part of Y Combinator's first batch. The idea was simple: create a platform where people could share and discuss the most interesting content on the internet.

Reddit sold to Condé Nast in 2006 for somewhere between $10-20 million. For most people, that would be the end of the story. But Ohanian's relationship with Reddit was just beginning.

He returned as Executive Chairman in 2014 to help lead the turnaround of the business. Under his leadership, Reddit grew from a niche platform to one of the most popular websites in the world, eventually reaching over 50 million daily active users.

Initialized Capital: The First Act

Before Seven Seven Six, Ohanian co-founded Initialized Capital with Garry Tan. This was more traditional venture capital - identify promising startups, write checks, help them grow.

The results speak for themselves. During Ohanian's time at Initialized, the firm's portfolio grew to represent over $200 billion in market value. Portfolio companies included some of the biggest names in tech: Instacart, Coinbase, Cruise, and dozens of others.

But by 2020, Ohanian was ready for something bigger. He wanted to build a venture firm that reflected his values around diversity and inclusion, not just his investment thesis.

Seven Seven Six: Rebuilding Venture Capital

In July 2020, Ohanian left his role as Managing Partner at Initialized to build Seven Seven Six from scratch. The vision was ambitious: create a tech startup that deploys venture capital, with an investor community that reflects our country's diversity.

The numbers are staggering:

• $750 million AUM after just one year (now approaching $1 billion)
• 50% women and 15% Black & Indigenous people in their LP base
• 38+ portfolio companies that have cumulatively raised over $800 million in follow-on capital
• Multiple unicorns including Axie Infinity (valued at $3 billion) and Pipe (valued at $2 billion)

But what really sets 776 apart isn't the numbers - it's the operating system.

Cerebro: The Secret Weapon

Here's where Ohanian's technology background becomes crucial. Instead of managing their portfolio with spreadsheets and email like most VCs, 776 built their own operating system called Cerebro.

Cerebro gives founders a way to search 776's network of 44,000 contacts and request an introduction with one click. Need a machine learning engineer? Looking for someone at Twitter? Instead of asking humans to remember connections, founders can query a database.

But it goes deeper than just contact management. All of 776's work lives in Cerebro, creating transparency and accountability not just within their team, but with their founders and investors.

As Ohanian puts it: "The goal is to scale the most valuable and most productizable parts of our work first, so that when we spend time with our founders it's the kind of work only humans can do well (empathy, strategy, creativity)."

This isn't just cool technology - it's a competitive advantage. While other VCs are still manually tracking their portfolios, 776 can provide real-time insights and connections at scale.

The Investment Portfolio: Betting on the Future

776's investment approach focuses on the "earliest possible" stage, with typical investments ranging from $100K to $10M. They almost always lead the rounds they participate in, which means they're not just following other investors - they're making independent decisions about which founders to back.

Current Portfolio Highlights:

Alt: Alternative asset trading platform that makes collectibles and alternative investments more accessible

Pipe: Global trading platform that makes recurring revenue streams tradable for their annual value (valued at $2 billion)

Axie Infinity: Web3 play-to-earn gaming universe that saw over 200x growth (valued at $3 billion at its peak)

Metafy: Video game education platform providing one-on-one access to champion-level gaming coaches

Notable Pattern: About 40% of 776's portfolio consists of crypto-related companies, reflecting Ohanian's early belief in blockchain technology's potential.

Crypto and Web3: The Contrarian Bet

While many VCs got burned by crypto investments in 2022-2023, Ohanian doubled down. In a 2022 interview with The Wall Street Journal, he said 776 planned to invest "primarily in crypto startups" out of their new fund.

This wasn't just following trends - it was contrarian thinking based on deep conviction. Ohanian saw the potential for blockchain technology to create new kinds of network effects and platform businesses, similar to what he experienced building Reddit.

The Axie Infinity investment exemplifies this thesis. The game created a new economic model where players could earn real money by playing, essentially turning gaming into work. At its peak, some players in the Philippines were earning more from Axie than from traditional jobs.

Diversity as Competitive Advantage

Here's where 776 differs most dramatically from traditional VC firms. While most firms talk about diversity, 776 made it central to their strategy from day one.

Their LP base is:

• 51% female-identifying (vs industry average of ~15%)
• 13% Black or Indigenous (vs industry average of ~3%)
• 10% Latino/a/e (vs industry average of ~2%)

But this isn't just about doing good - Ohanian argues it's about investing better. Different perspectives lead to different deal flow, which leads to different investment opportunities.

When your LP base and network looks different from everyone else's, you see companies that other VCs miss. That's potentially massive competitive advantage in a business where finding the best deals first is everything.

The Technology-First Approach

What makes 776 truly different is their approach to venture capital as a technology problem. Instead of just writing checks and providing advice, they've built software to systematically improve how they work with founders.

Cerebro Features:

• Real-time portfolio tracking and analytics
• Automated introduction matching
• Performance reporting for LPs
• Founder communication tools
• Deal flow management

This technology focus extends to how they evaluate investments. Rather than relying purely on gut feeling or pattern matching, they use data to identify trends and opportunities.

Investment Philosophy: People and Communities

Despite all the technology, Ohanian's investment philosophy remains fundamentally about people. His approach centers on three key factors:

1. Founder-Market Fit: Does this founder have unique insight into this problem? Ohanian looks for founders who have lived the problem they're trying to solve.

2. Community Potential: Can this company build a passionate community around their product? Reddit's success came from community, and Ohanian looks for that potential in every investment.

3. Platform Scalability: Can this business become infrastructure that other businesses depend on? This reflects his experience building Reddit into a platform that powered much of internet culture.

Recent Investments: Following the Pattern

776's recent investments reveal consistent themes:

Creator Economy: Companies that help creators monetize their audiences and build sustainable businesses

Future of Work: Tools that help remote and distributed teams collaborate more effectively

Financial Infrastructure: Platforms that make financial services more accessible and efficient

Gaming and Entertainment: Interactive experiences that build communities and create new economic models

The Accountability Innovation

One area where 776 particularly stands out is accountability. They provide "actual receipts" - monthly accountability reviews for the work they do for founders.

Most VCs promise to be helpful but rarely quantify what that means. 776 tracks metrics like:

• Number of introductions made
• Follow-up conversations facilitated
• Strategic advice sessions conducted
• Resources provided

This level of transparency is almost unheard of in venture capital, where most relationships are based on informal promises and good intentions.

Lessons for Emerging Fund Managers

Ohanian's approach offers several lessons for emerging fund managers:

1. Technology Can Be a Differentiator: While most VCs compete on brand and network, technology can provide real competitive advantages in portfolio management and founder support.

2. Diversity Drives Deal Flow: Building a diverse network creates access to different deal flow, potentially leading to better investment opportunities.

3. Accountability Builds Trust: Tracking and reporting on the value you provide builds stronger relationships with founders and LPs.

4. Think Platform, Not Product: Look for businesses that can become infrastructure for entire ecosystems, not just point solutions.

5. Community Matters: The best businesses build passionate communities, not just customer bases.

The Future Bet: AI and Communities

As we look ahead, Ohanian's investments suggest he's betting on the intersection of AI and community building. Many of 776's recent investments focus on tools that help creators and communities leverage AI to build stronger, more sustainable businesses.

This reflects his core thesis: technology is most powerful when it enhances human connections and communities, not when it replaces them.

The Anti-VC VC

Perhaps what's most interesting about Ohanian's approach is how it challenges traditional venture capital assumptions. While most VCs focus on individual returns, Ohanian focuses on ecosystem impact. While most VCs guard their deal flow jealously, 776 builds tools to share connections openly.

The results suggest this approach works. With nearly $1 billion under management and multiple unicorns in just a few years, 776 has proven that doing well and doing good aren't mutually exclusive.

The Bottom Line

Alexis Ohanian's journey from Reddit co-founder to venture capital innovator shows what's possible when you combine technical expertise, community insight, and a willingness to challenge industry norms.

With 776, he's not just investing in startups - he's rebuilding the venture capital industry itself. The firm's focus on diversity, technology, and accountability could become the template for the next generation of venture capital firms.

For founders, the lesson is clear: look for investors who are building for the future, not just investing in it. For other VCs, the message is even clearer: adapt or become irrelevant.

The venture capital industry is changing, and Alexis Ohanian is leading the way.