investor stories

Why Experienced Investors Can Benefit From Angel Squad

Even for folks with a wealth of angel investing experience, Angel Squad can help take your game to the next level. That was the case for Andy Louis-Charles, Chief Strategy Officer at Custom Ink

Andy is a seasoned angel investor and an early member of the Angel Squad network. With over a decade of investing experience behind him, he was amped to join the Squad, further elevate his toolkit, and share his experience with newer angels. 

We sat down with Andy to dive into his Squad experience, including: 

  1. Angel Squad’s multiplier effect on your deal flow
  2. Why experienced angels can still benefit from Angel Squad
  3. How a tight-knit investor community will change your outlook

“I came for the deal flow and stayed for the community. I’ve just been super impressed by the community that Angel Squad has been able to build up.” 

Why experienced angels can benefit from Angel Squad

Andy first heard about Angel Squad back in 2020. 

At that point, he was already a fan of the Hustle Fund investment thesis, which centers around: 

  1. Getting checks to founders of all types extremely early on
  2. Following through with the companies you invest in
  3. Adding on with breakouts and scalable data points

He had also been angel investing for over a decade then—mostly by sourcing his own deals and lightly participating in different angel groups. 

That approach helped him close anywhere from 6–12 deals per year. 

By the time Hustle Fund launched the Angel Squad program, Andy was game for three reasons: 

  1. Stellar track records — The Squad is run by the impressive people behind Hustle Fund. 
  2. Investor alignment — Angel Squad is generally oriented toward early-stage index investors — the exact style of investing Andy was already actively moving toward. 
  3. Deal flow — Most importantly, Andy wanted to ramp up his investing dramatically to close 100 deals per year. To do that, he needed a community for deal flow. 

“I liked the number and the velocity of deals that Hustle Fund was doing. Plus, I was looking to really amp up my angel investing to build a much broader portfolio.” 

What sets Angel Squad apart as an investor community? 

Andy admits he loves a well-done interview process. 

As an interviewee, it can give you a glimpse into the funnel and major priorities behind the interviewer. For instance, during his interview with Brian, Co-Founder & GM of Angel Squad, Andy learned a ton about the Squad’s unique value-adds. 

It also hit home for Andy that a rigorous interview and cohort curation process was necessary to build a thoughtful, dedicated group of diverse investors. 

Squad members enjoy top-tier investor content

As for what it’s like to participate in Angel Squad, Andy was (and continues to be) impressed by the top-tier content Squad members are exposed to. 

By “content,” he means both: 

  1. Hustle Fund’s content creation — This includes the firm’s publications and social media content, which are equally entertaining and genuinely informative. 
  2. Educational content for cohorts — The Squad meets weekly for tutorials by the Hustle Fund GPs, sessions to debate new deals, etc. In Andy’s words, they leverage their community to line up the best content available, from deal flow to founder partnerships. 

Come for the deal flow, stay for the community

Ultimately, the combination of the interview process and Hustle Fund’s consistently impressive content meant a winning experience for Andy. 

He joined for the deal flow—but wound up sticking around for the truly unique community. In his opinion, the environment cultivated by Angel Squad, compared to other angel communities, is in a league of its own. 

“Unlike other angel groups, Hustle Fund can leverage their one-of-a-kind community to secure the best content out there for Angel Squad: the best deals out there, the best founders out there.” 

The power of communal learning as an investor

Since Andy’s been an active angel investor for years, he has experience with jumping on calls with founders and having the right conversations. 

However, with Angel Squad, it’s as if you take those calls as a community. 

You get to follow up your one-on-ones with 30 other engaged people, which yields a ton of varying, unexpected viewpoints. After all, everyone in Angel Squad tends to come from diverse personal and professional walks of life. 

With that, Andy was impressed by the wide scope this brought to his learning experience. 

He’s grown to love participating in these live group sessions because every question—whether it’s his own or someone else’s that he never would’ve thought to ask—develops into a substantial, informative conversation. 

In Andy’s words, these live pitches provide, at minimum, as many insights as he could have gained independently. But he usually walks away with double the insights due to the community. 

The outsized value of having an investor community

Ultimately, having a like-minded community of other investors you can turn to is powerful for a couple of reasons. 

  1. A built-in knowledge network — Within Angel Squad, Andy benefits from hearing other folks’ smart questions and the knowledge they hold about other industries. 
  2. Opinions you can trust — Feedback from your peers in angel investing can and should affect whether you cut checks and for how much. That extra layer of vetting from trusted sources further hones your investment game. 

“You have community members offering their unique expertises on a deal in real time. I’ve been impressed by how much I’ve been able to learn with Angel Squad.”