investor stories

4 ways to easily upgrade your angel investing toolkit

To improve equity in VC, investors need to come from all backgrounds and walks of life.

But how can non-traditional investors build the necessary networks for angel investing without abandoning the full-time careers that make them so unique? 

Take Karin Dillie, VP of Partnerships at Recurate, who’s made an entire career out of digital resale. She joined Angel Squad in 2021, gaining access to a network of both seasoned investors and fellow newbies — all with a passion for learning about and diversifying the ecosystem. 

We sat down with Karin to dive into her Squad experience, covering topics like: 

  1. The unmatched diversity of professional backgrounds in Squad cohorts
  2. How working with legit deal flow elevates your investing perspectives
  3. Why aspiring early-stage investors should look into Angel Squad
“I love the accessibility of Angel Squad — how they see so many deals and put such interesting, curated opportunities in front of the angels. They really allow you to ask questions and build a community.” 

How Angel Squad Tactically Supports Full-Time Operators

Karin spent most of her career deeply embedded in the operations side of tech. 

By the time she started exploring VC, she was surprised by how opaque the field is and how insular deal flow groups are. 

She’d taken plenty of capital while working at The RealReal (she’d joined in its early stages), but angel investing was a totally different undertaking. 

Down the line, Karin would make her first angel investment in mid-2021. After a friend from business school tweeted about the deal, the tweet went viral — and Karin’s story was picked up by the New York Times in an article about accessible angel investing

Karin was featured alongside Elizabeth Yin, Co-Founder & General Partner at Hustle Fund, which spurred her to learn more about our firm. 

She liked what she saw, discovered Angel Squad, and applied to start investing with us. 

Finding Truly Diverse Cohorts in the Industry

The kickoff with her Squad cohort was valuable in and of itself. 

Karin found herself surrounded by both business school peers she hadn’t seen in years and people on career paths she knew nothing about. 

This exposure to so many different points of view was educational and reinforced her foundational understandings of angel investing. 

She was getting that direct, one-on-one exposure to both founders and investing leaders that’s impossible to come across on Twitter, where she’d first explored the VC world. 

“Hustle Fund showed up in a very insightful way for all of us — and for the founders that came on every week. Founders are just fantastic, dynamic people. I underestimated how much I would love hearing from them.” 

4 Ways to Upgrade Your Investing at Angel Squad

For Karin, her Squad experience provided experiences and insights that would’ve been unattainable otherwise. 

She outlines four of those essential gains below. 

1. Hands-On, Real-Time Deal Flow

Parsing through deal flow in real-time is far more impactful than just working on case studies. 

The main insight from case studies is that hindsight is 20/20. This doesn’t address the issue that in the here and now, the future is unknowable. 

In real-time boardrooms, different questions are asked and different ideas are floated, which has strengthened the lens through which Karin evaluates deals. She now approaches them holistically, rather than simply looking to her own background. 

2. Understanding Business Benchmarks

At Angel Squad, reading multiple decks to build out mental frameworks and formulate questions is a vital learning process. It assesses how comfortable Karin is with evaluating deals after being presented with different information. 

For instance, when she first joined Recurate, the company had just raised a seed round. 

While her operating experience has heavily influenced her investing, the reverse also applies. 

Karin’s experience with Angel Squad has made her far more comfortable in understanding Recurate and the benchmarks they should be hitting. 

3. Openness to Different Investment Areas

After experiencing her cohort’s kickoff, Karin realized that investment decisions are frequently constrained by personal experiences and comfort levels. 

Now, she’s intentionally open to investing in deals outside of the world she knows. 

4. The Diversity of Experiences at Angel Squad

The previous point ties directly into the fact that Karin’s cohort comprised people of all kinds of personal and professional backgrounds. 

Like her, a handful worked at early-stage startups and were breaking into investments. 

But many also came from later-stage startups and public tech companies — or they worked as doctors, lawyers, and in other fields outside of traditional tech and VC ecosystems. 

Unifying those different perspectives within a cohort encouraged constant rich discussions. It challenged many of Karin’s own notions, especially when it came to assessing and problem-solving with deal flow. 

Every member’s questions and input validated her own and affirmed that everyone had joined Angel Squad for a space to learn.

The Outsized ROI in an Inclusive Investment Ecosystem

Karin found the partners at Hustle Fund collegial, good-natured, and hilarious at every turn. 

She calls Angel Squad and the larger Fund alike an excellent place to feel connected to people who are all intent on creating a more expansive, inclusive investment ecosystem. 

It’s also not a huge time suck. Angel Squad can be as time-consuming as you allow it to — and the ROI is ultimately very high. 

If you want to practice flexing your investment and analysis muscles, Karin emphasizes that Angel Squad is a unique and unmatched opportunity to do so. 

“You get comfortable with giving your money to a space that you don't fully understand but has the potential for high returns. So, I’d say my aperture has expanded through what I learned with Angel Squad.” 

Learn, network, support founders and invest alongside Hustle Fund.