How to Filter Deal Flow

Ian Logan is VP of Engineering at Rose Rocket, the YC-backed, SaaS-based Transportation Management System helping transport companies of all sizes automate their workflows. 

He’s also actively angel investing and leading his syndicate, I & Z Investment Club. We sat down with Ian to dive into his best practices and unique journey as an investor. We cover topics like: 

  1. Carving out a space for diverse operator-investors
  2. Tips for efficiently filtering inbound deal flow
  3. The process of scaling an angel syndicate
“I love actively engaging with other founders and thinking about different domains and problem sets. I angel invest because it brings me a lot of joy.” 

Why you should invest in community as an angel-operator

Ian got his start as an operator at Airbnb, which proved to be a crucial launching point for building a network. He invested in a few colleagues' startups, met other founders through them, and began to form genuine, mutually beneficial relationships. 

He kept building this community once he arrived at Angel Squad. (In fact, this was one of his main reasons for joining his cohort in the first place.) 

Beyond this, he joined the Squad to grow more tactical in his investments and active in the angel investing ecosystem. 

Since then, he’s grown into a prolific investor and begun to diversify his projects. These include: 

Investing 101: how to efficiently filter inbound deal flow

When it comes to choosing what and whom to invest in, Ian has found it’s best to set some hard and fast rules to follow. 

As a prolific investor, he gets countless messages from founders in his Twitter DMs and email inbox — all asking him to consider their product. There are tons of potential choices to make. 

So, he breaks down his guidelines for easily filtering through this potential deal flow. 

1. Set rules for what not to invest in

With so many opportunities, things can progress far more quickly and simply when you set rules for companies that are off the table — under all circumstances. 

In Ian’s case, for instance, he’s decided to never get involved with any vices: companies whose products center gambling, alcohol, weed, etc. He’s not against these spaces, but in terms of accelerating assessments, removing those players from his stack just makes sense. 

Drawing strict rules on criteria, verticals, and stages will ultimately save time. It also enables Ian to focus on projects that genuinely spark passion and align with him as an individual. 

2. Pursue the companies you’re passionate about

Along those lines, choosing the best companies for you to invest in entails considering just how passionate you are about the product. Ian will ask himself: 

  1. Can I see myself actually using the product? 
  2. Do I believe there’s a good cause behind it? 
  3. Does this company align with my values?

Of course, this can also go beyond the product and encompass the values or mission of the founder and their founding team. 

In the end, angel investors are putting up more than just money. They’re setting aside time and energy for the companies and teams they decide to involve themselves with, so actually caring about the product and feeling fueled by its mission matters tremendously to Ian. 

After all, he dedicated himself to Angel Squad because angel investing is one space that brings him pure joy. 

3. Assess the basic viability of the company

If a company aligns with his passions and broader investment interests, Ian will evaluate the founder, the market, and the product or service itself. 

As an engineering operator, he often gets involved with dev tools and productivity projects, which are easier for him to judge through his familiarity with these markets. Generally, however, he’s open to any startup that meets his guidelines and investment thesis. 

This is also where Angel Squad comes into play. 

Our team and programming have equipped Ian with frameworks and relevant experience to make his assessment process far sharper and speedier. 

He also highlights the impact of access to Hustle Fund’s network and early-stage portfolio. 

“If I’m going to invest my time in something, it ought to align with things I care about or values I have. That matters a lot to me.” 

Designing and scaling a high-powered angel syndicate

After reinforcing his thesis, expertise, and experience as an investor through Angel Squad, Ian was ready to broaden his horizons. 

On top of cutting personal checks, he runs the aforementioned syndicate with his investment partner Zach, whom he met through mutual investor circles. The two realized they shared very similar investment interests and goals, leading them to partner up. 

They opted for a syndicate since they didn’t want the commitment of a fund — at least, not yet. 

A syndicate would also be a way to build a brand for themselves, which is how I & Z was born. 

Fast forward and I & Z has successfully raised a couple of SPVs. They were also able to take notes from other syndicate leads to avoid typical growing pains. 

“We really had to be proactive,” Ian recounts. “We definitely hustled.” 

He describes their recipe for early success as spending ample time with founders, being hands-on and learning about their projects, as well as consistently calling up their LPs and being ready to be evaluated each time. 

“Syndicates are a very interesting experience. There’s the founder side of pitches and helping them raise, and then there’s the LP side. I really enjoy doing both.”

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