Why Scout Programs Improve Your Deal Filter
Maya Caddle is a Product Manager connecting global users across emerging and developed markets, from London to Nigeria to Hong Kong. She recently built a crypto company at Nestcoin and now is a Manager for Strategic Projects and Investments.
She’s also a Venture Scout for SHL Capital, Microtraction, and Hustle Fund, sharing deal flow in Africa. We sat down with Maya to dive into her Angel Squad experience, covering:
- How Angel Squad tactically improved her scouting success rate
- Learning to assess companies across cultures and continents
- The value of having your network actively advocate for you
"Before joining Hustle Fund, I'd successfully scouted one venture. My track record has since improved dramatically. Angel Squad was a huge driver of that growth."
Build investment literacy through a diverse angel community
Angel Squad's emphasis on communal learning and investing has been a core benefit of Maya's experience. She attributes this to two intertwined realities of the industry:
- Scouting and angel investing, especially for newcomers, can be isolating pursuits
- Angel investors have historically been left to struggle, fail, and learn by themselves
In Maya’s experience, angel investing can be a lonely, isolated path. Not every fund cares to establish support systems or centralized communities for their scouts.
And those communities that do exist can often ice out newer investors by basing the value of your insights on the number of large firms on your resumé.
Joining the Angel Squad community was a game-changer.
Aside from the fortune of having a fund to substantially support her work, she describes her fellow Angel Squad members as individually wonderful.
Everyone is willing to reach out to both learn and teach, even as Angel Squad comprises countless experience levels and personal and professional backgrounds.
For instance, Maya recently received a LinkedIn message from someone with many more years of industry experience — but still looking to learn from a younger scout’s unique perspective.
That kind of acceptance is an unfortunate rarity in the space, says Maya, but easily one of the best aspects of Angel Squad.
How to expand your angel investing knowledge network
If someone started angel investing half a decade ago, they'd have a slim chance of finding a modern community like Angel Squad.
There were no live feedback loops or dialogues with experts unless you networked like hell. You learned everything through reading articles or books — plus tons of trial and error.
While both are still critical, Maya affirms that having a network to expand or push back on your potentially flawed or narrow investment theories and opinions is essential.
The companies you fund and the audiences they serve don't exist in bubbles, which is why prolific VCs emphasize diverse knowledge networks on top of diverse research.
Vocalizing ideas and complexifying them through debate — with fellow Angel Squad members as well as Hustle Fund partners — challenge her fundamental ideas of investing in the best way.
As she tells it: “At Angel Squad, there aren’t any silly questions about investing.”
“Dialoguing with people from different backgrounds leads to more nuanced, holistic investment debates. It’s an invaluable thing that Angel Squad provides.”
Angel Squad: a community that will truly advocate for you
Since starting to scout with Angel Squad, Maya highlights the unparalleled experience of having a fund believe in your skills and go to bat for you.
- Mutual respect — If the team is unsure of a startup but Maya believes in its potential, they’ll take her word for it and, at the very least, stage an intro call.
- Genuine investment — Even if she’s not actively seeking support, Hustle Fund advocates for her capabilities and character. They’re invested in Maya’s growth and opportunities.
This level of support has also been her experience across the board with the Hustle Fund team, regardless of the individual partner’s seniority.
It's been rewarding and, quite simply, a regular confidence boost for her.
After all: “If I tell you about an amazing startup and you won’t even value that opinion, why should I commit my time to you as a scout?”
“I love that Hustle Fund always advocates for me, even if I’m not outwardly asking for it. That creates a sense of authentic care. You’re not just another number.”
Maya’s playbook: understand cultural contexts and geographies
Angel Squad has provided Maya with a great deal of investment skills, theory, and concepts.
One piece of advice, which she took from Elizabeth, a Hustle Fund co-founder and GP, has been particularly crucial to her development as a global investor
It's obvious but overlooked: An investment's performance, distribution, and scalability are deeply linked to the unique cultural contexts and geographies in which it functions.
For example, when deciding early sales tactics for a social commerce venture:
- In the U.S., it’d be costly and difficult to hire a team to go door to door and encourage businesses to sign up for your platform.
- Meanwhile, in the context of an emerging market, that approach is far cheaper.
How you evaluate and strategize for that startup shifts dramatically based on global context.
And it demands deliberate cross-cultural efforts — far more than just creating a new division and giving it a throwaway label like “Hustle Fund for Asia” or “Angel Squad in Africa.”
Again, it’s a basic principle, but one many VCs failed to account for in the last investing bubble.
"In assessing deals, you're missing many cultural nuances and contexts as a VC in Silicon Valley. I'm really appreciative to have learned that through Angel Squad."
Why scouting programs help drive hands-on expertise
Ultimately, the pinnacle of Maya’s Angel Squad experience has been the opportunity to actually scout for Hustle Fund. She outlines three reasons why:
- Access — If you lack the personal capital or the entry points to the industry, it’s nearly impossible to get practical experience as an angel investor.
- Name recognition — Founders are eager to engage with Maya due to Hustle Fund’s reputation. Being in Angel Squad has opened up deal flow and accelerated her ability to find the best deals as a scout.
- Tactical learning — You learn mainly by doing, not by reading theory. Plain and simple. Maya has gotten to put resources like the Hustle Fund Deal Assessment Framework into practice in her frequent meetings with founders and the deal memos she writes.
Before discovering the Hustle Fund community, Maya had successfully scouted one startup among a long line of pitches. She was doing a ton of work without seeing the fruits of her labor.
Like many investors when they first start out, she was heavily influenced by founders’ abilities to spin or sell the project, as opposed to anchoring her assessments in data, market viability, etc.
Then, after joining Angel Squad, her progress accelerated 10X.
Her track record of one evolved into active scouting for roughly 6–7 months, with at least one pitch per month resulting in an actual investment by a fund.
Eche, CEO at Afropolitan, adds: “During our fundraise for Afropolitan, Maya was a great resource for us. She scouted us for Sahil and Elizabeth Yin and spent multiple hours prepping us for the investor pitch. I credit her with helping me become better at fundraising as a founder.” Afropolitan went on to raise from the likes of Balaji Srinivasan and SyndicateDAO.
Neto, CEO at WellaHealth, makes a point that: “Maya was an excellent help in connecting us to Hustlefund, she helped us refine our pitch to ensure we stood a good chance of success. The best thing about Maya is her amiable personality and infectious optimism. she brought her full self to all our interactions and always left us feeling pumped and energized.”
Maya names Angel Squad as a key driver of that learning curve and progress, having learned to analyze and filter through decks and meetings with nuance, sharpness, and efficiency.
“You don’t learn solely through theory. You learn through doing — and actually scouting for Hustle Fund has brought me significantly closer to my end goals.”
