Ripple and the Imperfect Art of Decision Making

A few years ago; mid-2013 to be exact, we found ourselves in a bit of a dilemma. We were introduced to a new startup named Ripple who, at the time, needed to do quite a bit of hiring. Our time working with them has since turned into one of our most amazing client stories, in fact, it’s one of my personal favorites. But in the beginning, the choice to work with them wasn’t quite so obvious.

Malcolm Gladwell says that everybody makes decisions in the blink of a moment and then spends the rest of their time either validating or overturning them.

While normally taking on a great new client is a no-brainer for a company, for us it has heightened implications almost akin to that of a whole new job change. Because our team gets embedded in this new client environment for 6-12 month timeframes, pick right and the world is bright for our team and company. Pick wrong and we face unnecessary adversity and oftentimes regret and loss.

Over the years, we’ve had the incredible fortune to work with some of the top technology companies in our industry, and at unique periods of time that were meaningful inflection points in their growth and future:

  • Pinterest in 2012/13 at the onset of their growth boom

  • Reddit in 2015/16 when their original founder re-joined

  • Airbnb in 2015 after deciding to up-level its talent brand

We’ve also worked with a number of others that didn’t pan out the way we expected. For example, trust me when I tell you that you didn’t want to be a recruiter at Groupon in 2014 during its 6-month skid from being at a market high to being at a market low.

Colin Powell says the optimal time to make a decision is when you have 40-70% of the necessary information. Make it with less information and you take on unnecessary risk. Make it with too much information and you risk missing the opportunity altogether.

In order to increase our odds of making the best decision for our team and company when taking on a new client, we use the following criteria and make it our goal to uncover the answers to as many of these questions throughout our consideration process:

  • Bincer experience: Will our team enjoy their time working with the company? Will we be treated as partners and not vendors? Will we be embraced as part of the team and respected in our efforts to recruit top talent for the team and company?

  • Client impact: Will we leave a positive impact on the company and the market they serve? Are we coming in at a meaningful time and to work on a critical set of hiring needs and priorities?

  • Candidate representation: Will candidates be excited to hear about this opportunity? Is the company distinguished, is the team impressive, is the culture attractive, and can we be successful in attracting the desired talent?

  • Strategic value: Is there a strategic benefit to us taking on this opportunity? Will we extend our network, establish new relationships, expand into new geographies, new practices, and new domains?

Let’s get back to Ripple.

Ripple had an impressive set of startup vitals:

  • Impressive founder & early-stage team

  • Funding from leading VC firms

  • Moonshot story & vision, that we were really excited about

  • Sizeable hiring needs

  • Great hiring leaders, which we thought our team would enjoy working with

We also had our concerns:

  • The office was fairly empty with a majority of the team either working remotely or in the process of relocating

  • A contrarian vision that didn’t fully align with popular market consensus

  • Hiring leaders that had just recently joined so there was not a lot of hiring continuity to build upon

When mapped against our decision-making criteria, Ripple came out strong enough to proceed. Well so did the other company we were considering. We could only pick one (based on limited team bandwidth and availability) and we were at a crossroads.

So what’s a decision maker to do?

  • Forced stack ranking

  • Pros & cons lists

  • Alignment against principles & values

  • Identify new criteria

  • Consult with trusted partners, friends & family

  • Follow the white rabbit (hey it worked for Neo!)

All great tools and all have their place in any good decision making process.

It’s near impossible to predict a winning experience and the quality of a decision is only obvious in hindsight.

I vividly remember that day like it was yesterday. I was driving with my family on the 5 Freeway from the Bay Area to Los Angeles. Both Ripple and the other company were ready to sign contracts but we could only pick one. I had spoken with my partners, they weighed in with their input and the decision was ready to be made.

Insert a new piece of information. I happen to be a closet Deadhead. Not too hardcore, but I may or may not have owned a few tie-dye shirts and a truck full of stickers at one point in my life.

Insert more information. My favorite song of theirs happens to be a little-known one named Ripple. I half-jokingly mentioned this during one of our Business Development meetings with the company and they half-jokingly mentioned that they had purchased the Ripple website URL from a Grateful Dead fan site. Coincidence, I think not!

I decided to look to the song for an answer:

“There is a road, no simple highway
Between the dawn and the dark of night
And if you go no one may follow
That path is for your steps alone

Ripple in still water
When there is no pebble tossed
Nor wind to blow

You who choose to lead must follow
But if you fall you fall alone
If you should stand then who's to guide you?
If I knew the way I would take you home”

Every decision has that “fuck it moment”. That point of no return where you’ve collected enough information, you’ve consulted enough partners, you’re written enough pros/cons lists and the decision needs to be made. That moment to throw caution to the wind (or make that ripple in the water) and go with the unknown in pursuit of whatever decision you just made.

Both exhilarating and scary, it’s this moment that needs to be embraced, recognized, and then honed. For its the cumulative of your decisions in these moments that define your today and those moments of today that will define your tomorrow.

Ripple had a moonshot vision to build the internet of money. Their CEO was a Fintech legend and their team made up of early crypto-pioneers. Bitcoin was growing in its notoriety and candidates were excited about the potential. There was a growing buzz in the space and we wanted in.

Today, Ripple employs almost 400 people, it’s valued at well over 1 Billion (some estimate as high as 5B) and is considered a leader in the banking revolution. They also happen to be an incredibly great group of people who were very kind, engaging and who always treated our team well.

In closing, there are many frameworks to follow when making a decision. Go with Malcolm and you’re blinking your way to a spontaneous future. Go with Colin and you’re collecting information to create the most informed future possible. Regardless of framework, all paths lead to that ‘fuck it moment’ for you to embrace in all its imperfection and glory.

For as Jerry Garcia so brilliantly put it, ‘your path is for your steps alone”.

Boris Epstein