How to Balance Financial Risk & Reward as an Angel Investor

Trond Wuellner is a Director of Product Management at YouTube focused on creator empowerment. Previously, he spent 13+ years at Google, leading new tech development for global products like Google Wifi and Chrome OS. 

In the first piece of this two-part series, we sat down with Trond to hear why his Angel Squad experience was crucial to becoming a prolific investor today. We dive into: 

  1. How the Angel Squad network will keep you well-connected for life
  2. Getting to handle legitimate Hustle Fund deals from day one
  3. Learning to dive into angel investing as a tech operator
“My first step into angel investing was really based around advising startups, providing hands-on support, and helping build their businesses.” 

How can an operator break into angel investing? 

Trond’s journey to angel investing was fortuitous.

As an MIT grad, he was classmates with Elizabeth Yin, one of Hustle Fund’s GPs and Co-Founders, who’s prolifically invested in 500+ startups. In short: She’s the real deal. 

While Trond has technically been in the angel investing ecosystem for about five years, most of the deals he’s done came directly through Elizabeth. “She’s actually a big part of why I got involved in investing and how I got started.” 

Naturally, when she began developing Angel Squad, she clued him in on it. 

When he first heard about it, all he thought was: “Brilliant. I should totally do this.” 

To pass up the opportunity — an angel club with unlimited networking opportunities and almost nonexistent barriers to entry — would be ridiculous. 

Angel Squad’s edge: learning by doing

Upon joining Angel Squad, Trond realized that everyone — from his fellow cohort members to the Hustle Fund team — was more than willing to share their personal investment strategies, frameworks, etc. 

He valued this deeply, since, outside of his Squad, he’d likely never converse with these experts. 

His main goals for the experience were “learning [everything about] the ecosystem and the players involved in creating great businesses.” 

And, of course, there’s no better way to learn than by doing. 

Trond started providing his services as an informal advisor to startups that were eager to expand their capabilities as small teams. Soon enough, after collaborating closely with these groups, he realized he was falling in love with the work. 

Angel Squad was clearly the right place for him then. The next inevitable step was more concrete (i.e., financial) involvement. 

“As I got involved with the companies I was advising, I fell in love with the businesses and their people. I wanted to start making direct investments.” 

The outsized ROI on reviewing live Hustle Fund deals

Every Angel Squad member gets to work directly with a selection of Hustle Fund’s legitimate deal flow. Trond was immediately struck by the pure quality of these businesses. 

After all, each investment has already made it past round one with a Hustle Fund team member. It sets a standard that’s uncommon among other angel clubs. 

This is especially valuable considering many Squad participants, like Trond, are still full-time operators. Instead of filtering through mountains of deal flow, they can effectively utilize their time in Angel Squad to practice real assessments, due diligence, etc. 

Even more, they can evaluate these startups confidently, knowing they’re real opportunities to strengthen their portfolios and perhaps turn a profit. 

“When something is passed through Hustle Fund’s filter and brought to the Squad, there’s a high level of confidence among us — and in the businesses themselves.” 

For Trond, that dedication to creating the best possible learning experience for new angels is close to his heart, because it’s so difficult to find elsewhere. 

“Hustle Fund has a very clear vision of the types of entrepreneurs, the types of businesses, and the phases of growth that they invest in.” 

The Angel Squad difference: a network engineered for growth

According to Trond, Angel Squad equips its members with two things — both of which are critical to successful investments: 

  1. The access to and ability to invest in early-stage startups
  2. The knowledge and network required to avoid catastrophic mistakes

Aspiring angels can both learn directly from industry leaders at Hustle Fund and practice with investment opportunities in a constructive learning environment. 

In Trond’s opinion, this is the kind of space that breeds driven, capable angel investors. 

Learning from Hustle Fund’s extended, diverse network

Perhaps the most important element of Angel Squad is its diverse community and industry network — in which no two people are quite the same in terms of career paths, investment frameworks, demographic backgrounds, etc. 

In Trond’s experience, “This community has an expert on every topic you can come up with.” 

What makes it even better is that Squad members can connect with these experts so easily. 

Having these knowledge networks within reach has been crucial for accelerating his growth as an investor while minimizing growing pains. 

“You don’t have to go through the painful learning process of seeing things go wrong firsthand.” 

An investment community that leads to (genuine) friendships

Today, Trond could be considered a seasoned and prolific angel investor. 

And he knows Angel Squad is the main reason for his large, diversified network that’s helped him get where he is. 

Beyond this, he affirms that the value of Angel Squad’s extended community is the high caliber of every single person in it. As he puts it: “The class of individuals that’s joining the Squad are people that I believe in.” 

That can likely be attributed to the thorough process that Hustle Fund puts applicants through. 

No prior portfolio or MBA is required, but every Squad member must: 

  • Have an intense desire to learn about investing
  • Be willing to get their hands dirty and learn from mistakes
  • Prioritize community-building with their cohort and fellow angels

By putting tons of individuals like this in one room, you get a cohort where every person has something unique (experience with a sector, a user demographic, etc.) to bring to the table. 

With that, the genuine connections Trond has formed have far exceeded his expectations — and also made him want to stay engaged for as long as possible. He doesn’t take it for granted. 

Participating in Angel Squad has given him an equally challenging, nurturing, and passionate group of people to learn alongside. 

Your Squad network will never stop growing

Finally, Trond highlights the fact that Angel Squad’s community keeps growing at an impressive rate — not just in quantity, but also quality. 

In his words, “My Squad has continually gotten stronger and stronger and stronger.” 

It’s not only enriched his individual growth trajectory as an angel, it’s also afforded him more interesting opportunities for networking and deal flow. 

Critically, the cycle feeds itself. With a larger network, an angel investor has more access to deal flow. With more deal flows and more investments come a larger network. 

“The reality is I love the people in my Squad. It’s just fun to hang out with them, in addition to learning and growing as angel investors alongside each other.”

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