I was once in a Robert Greene "Reality Group"

Working at Wonolo changed my life and perspective forever.

Even to this day, I have yet to experience the same level of camaraderie, drive, raw talent, and enthusiasm in any other work environment. It was such a unique culture, and I commend the leadership for crafting that environment.

It taught me about the importance of defining your core values, writing them down, living by them, repeating them, and assembling people who align with them.

It was a place that encouraged humanism and empathy while also expecting maximum effort and a growth mindset. Additionally, it was a culture based in realism. We made calculated decisions using data and open debate to grow rapidly and derisk certain existential crises throughout the growth phase.

Most importantly, it was a place that valued trust above all else.

Robert Greene talks about a concept called the “Reality Group”. This is defined as a team with an excellent working culture: effective, empathetic, grounded in reality, and making good decisions.

He says that what creates a functional, healthy dynamic is the ability of the group to maintain a tight relationship to reality.

The healthy group puts primary emphasis on the work itself, on getting the most out of its resources and adapting to all of the inevitable changes. Not wasting time on endless political games, such a group can accomplish 10X more than the dysfunctional variety.

The following are five key strategies for achieving this, all of which should be put into practice.

Instill a collective sense of purpose.

• This purpose is not vague or implied but clearly stated and publicized.

The founders, Yong Kim, Jeremy Burton, and AJ Brustein would constantly talk about the company’s purpose and use our value system, which we called the TAO of Wonolo, to create a framework on which all decisions were made. This unified the team and focused our energy in a collective singular direction.

Assemble the right team of lieutenants.

• Do not base your selection on people’s charm and be reluctant to hire friends.
• Select for this team people who have skills that you lack, each individual with their particular strengths.
• You also want this team of lieutenants to be diverse in temperament, background, and ideas.

Two traits were consistent across the entire company at Wonolo, a high degree of morality and undeniable, in-your-face raw talent. There was not a single person in the company who I didn’t admire in some way and where I didn’t welcome their opinion and perspective. It was why, even to this day, I am still very close to many of those people.

Let information and ideas flow freely.

• To achieve this, you want to encourage frank discussion up and down the line, with members trusting that they can do so. You listen to your foot soldiers.
• Extend this open communication to the ability for the group to criticize itself and its performance, particularly after any mistakes or failures.

There were many times at the company where junior PMs would lead the team through the feature they envisioned and willed it into creation. Many of these ideas caused a step change improvement in the product and user experience. It was a place that valued the quality of the ideas and not the seniority of the idea, and it helped the product evolve rapidly. I have yet to be at a company that had such a rapid feature release or bug fix schedule.

Infect the group with productive emotions.

• As part of this strategy, always keep the group focused on completing concrete tasks, which will naturally ground and calm them.
• Infect the group with a sense of resolution that emanates from you. You are not upset by setbacks; you keep advancing and working on problems. You are persistent.
• Periodically change up routines, surprise the group with something new or challenging.
• Most important, showing a lack of fear and an overall openness to new ideas will have the most therapeutic effect of all.

One of the more interesting things is that I rarely experienced excessive pontification at the company. It was universal that our actions were geared toward productivity. This created speed and clarity in our workflow.

Forge a battle-tested group.

• Give various members some relatively challenging tasks or shorter deadlines than usual, and see how they respond.
• In the end, you want a group that has been through a few wars, dealt with them reasonably well, and now is battle-tested. They do not wilt at the sign of new obstacles and in fact welcome them.

Whether it was planning a market expansion, battling existential legislative changes, capital raising, or exploring new business models, everyone was expected to tackle challenges they had never encountered, decide the best and most rational path forward, and work as a team.

I will never forget the TAO of Wonolo and how these values unified us.

1. We put users first.
2. We make calculated risks and prioritize high impact projects.
3. We act as owners and work as teams.
4. We value hard work, and we celebrate results.
5. We take our work seriously, but not ourselves.
6. We hold the 5Ps (Polite, Professional, Punctual, Positive, and Prepared) to be self-evident.

I am forever grateful for that experience and for the leaders who taught me how to be one.