investor stories

How to Effectively Transition From Operator to Angel Investor

Angel investing doesn’t have to deliver a binary outcome accompanied by a hit-or-miss mentality. Instead, view it as a lifelong skill and learn to set yourself up for smart outcomes. 

As a newcomer to investing from the e-commerce realm, Tess Frugé — a seasoned strategy exec and fractional COO — leveraged her Angel Squad experience to learn to do exactly that. 

In Part 2 of our interview, we sat down with Tess to learn how Hustle Fund broadened her knowledge, prospects, and success in angel investing. We covers topics like: 

  1. Riding the learning curve of angel investing
  2. Juggling a family, full-time career, and investments
  3. How to treat investing like a lifelong skill set

“My worldview had been limited to eCommerce and DTC products. That’s where I’d spent most of my career. I joined Angel Squad with the intention of learning way more about other industries.” 

Tess’s journey — from eCom operator to up-and-coming angel

Earlier this year, Tess left full-time employment to work as an independent consultant and fractional COO. She soon realized her worldview had been limited to eCom and DTC; that’s where she’d spent most of her career. 

As someone dedicated to lifelong learning, that realization drove her to join Angel Squad. 

Tess had always wanted to dive into other industries and their commercial trends. Approaching them from the investor’s angle seemed like the ideal way to do it. 

Right off the bat, she was drawn to two aspects of Angel Squad’s method. 

  1. A “conscious education” — Plenty of syndicates send out updates on deal opportunities, but Angel Squad builds this into their curriculum and gives members direct access to Hustle Fund’s seasoned GPs. 
  2. Work with legit deal flow — Squad members get access to deals curated by the Hustle Fund team. They participate in legitimate, promising investments while gaining insights and expertise from high-level investors at work. 

How operators can find their way to the investor’s seat

As a fractional COO, Tess jumps in with early-stage companies on whatever tasks need completing. For instance: 

  • She brings the high-value knowledge and execution that founders don’t have in order to kick company projects into high gear. 
  • She’s a strategic voice in the room. When companies need to think tactically about their ops, execution, and path forward, she’s their go-to. 

While her professional experience was impressive, Tess didn’t have any investing background. 

Any money she made as her career progressed just went to index funds. 

After working in eCom for over a decade, she realized her worldview had been limited to that industry and DTC businesses. 

Tess joined Angel Squad with the intention of changing that. 

When to make the jump toward investing

This career shift has enabled more work-life flexibility than she’s had in 16 years. 

Tess is raising two little kids. But, through Angel Squad, she still felt she had the bandwidth to become a more educated investor and start writing checks. 

It also made sense to make moves in her investing career now because once she’s learned the ropes, it’ll be that much easier to keep growing. 

That’s why she was so determined to kick off with Angel Squad this past year and learn as much as possible from the pros and her fellow up-and-coming angels. 

“With a compounding process, the sooner you start, the exponentially greater your learnings and results as an investor will be.” 

Approach angel investing as a lifelong skill set

As a self-described lifelong learner, Tess views investing as a 10-year (or longer) learning curve. 

That’s in large part because Hustle Fund is an early-stage investment firm. The companies she’s invested in so far likely won’t play out as failures or success stories for at least three, five, or even ten years to come. 

With every check, Tess is bound to learn lessons. She may just have to wait for them to vest. 

That’s become a core part of her framework: 

By investing today, she’s not just aiming for potential downstream returns. She’s also sharpening her mental models and investing instincts right away. 

“I figure now is the time to start investing in gaining those lessons. Once you start, it’s easier to continue.”