September 30, 2021 | 4 minutes read

Contrarian Investments — The Road Less Traveled

  • #Startup
  • #investment
Avi Eyal
Managing Partner, Entrée Capital

In 1915, Robert Frost, a famous poet wrote: 

“Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.”

The poem inspires readers to take the path less traveled, to be a daredevil, and to feel confident that it will make “all the difference”. 

Entrée’s mission is to “Partner with the Exceptional to Build the Impossible”- and much like the road less traveled, it is not often one comes across both exceptional people and great ideas in one package. Exceptional founders challenge the status quo and seek to find disruptive solutions to challenges that are either incredibly hard to solve or that have been overlooked for decades (and accepted as the norm). 

Exceptional founders take the road less traveled.

Entrée’s 4T formula of early-stage investing is made up of TAM (Total addressable market), Team, Technology (Product), and Timing. Cyber, marketing SaaS, etc are often oversold sectors – they’re the road that is traveled.  

We are constantly looking for category killers, such as Breezometer that solves the need for hyper-accurate environmental pollution, pollen, fire hazard, and other data. Or Broadlume, a company rebuilding the flooring industry, and now we’ve invested in Empathy, a startup that deals holistically, psychologically, and practically with bereavement at every touchpoint along this difficult journey. 

We’ve known the Empathy founders for 8 years or so. Ron, Empathy’s CEO, invested with us in pre-seed opportunities over the past decade. On that journey, we found that we both had a similar eye for disruptive opportunities rather than startups offering an incremental improvement of a product or service. When it came to their new business, the Empathy founders didn’t send us a deck, but rather a 37-page overview memo that really explained why they wanted to go after this market. It was deeply researched and full of insights and showed us that the opportunity was tough, fragmented, hadn’t innovated in decades, and incredibly large. These founders had what it takes to run down that road less traveled and succeed. 

And it is starting to pay off.

In just a few months after launching their app, the Empathy team has succeeded in reaching families through both B2B and B2C channels, is in use in 50 states, and has closed partnerships with multiple organizations. 

There are hundreds of founders like this. From Elon Musk (SpaceX, Tesla) to Steve Jobs (Apple) and more accessible everyday folks like Shai Winneger (Lemonade), TJ Parker (PillPack), Babs Ogundeyi (Kuda), Boaz Vinogradov (Magnus Metal)), and many more. 

In virtually every country you will find local and global innovators that break the mold. 


The Road Less-Traveled Has Potholes 

It takes courage. There are great challenges in taking that road less traveled. There will always be the naysayers, the ones who ask “who are these crazy people, don’t they know how this is done?” They’re the gatekeepers trying to keep to the old ways for two main reasons: a) a presumed loss of economic benefit and b) a lack of innovation and psychology associated with being the lazy incumbent i.e. it’s easier to stay as you are.  

A critical mass of early adopters is necessary to overcome the chasm, and a few lucky breaks can’t hurt either ?. The overarching commonality of all the exceptional founders, like those at Empathy, is that they “refuse to go into the night without a fight”. They have unparalleled conviction and are patient and tough enough to persevere. 


Some Advice for the True Disruptors

To those brave enough to take that road less traveled, here’s some simple advice that can be learned from the rest of the poem:

  • “Two roads diverged in a yellow wood, and sorry I could not travel both…”
    Ideally, you should have a deep history and understanding from within the space you’re tackling, so you’ve experienced firsthand the challenges and intricacies. You can’t be one foot in, one foot out to hedge your bets.

  • “And be one traveler, long I stood…And looked down one as far as I could”
    Stand there long enough and look. Conduct deep research on the topic and have a clear understanding of what you can offer and if it can make a difference. But don’t get caught up in analysis:paralysis.

  • “I shall be telling this with a sigh somewhere ages and ages hence…”
    Be consistent, and be patient – it may be a very long time before you see success.

So founders, if you’re up for it, take that road less traveled, it may just make all the difference.