#MentalNote

Less Is More

I had an amazing 2021. There’s so much that’s happened to radically transform my life in 365 days. I’m super grateful but success begets new problems.

I’m constantly overwhelmed and feel like I don’t have time to get basic things done. I feel like weeks go by faster and faster but I have less time to do the things that are important to me.

I’ve tried to be more deliberate about my time toward the end of the year. I’ve started playing basketball again, taken time to jump into photography, and I took my ps4 back from my brother. (GTA 5 online)… Things that give me daily joy.

For 2022, I’m going to optimize for minimalism. Professionally, personally, and spiritually. I need more energy to focus on high-impact initiatives and relationships. What does this look like in practice? Here are some ideas:

  1. Selling some of my companies or hiring people to run full time.
  2. Getting rid of clothing
  3. Selling / consolidating my tech (apps/ hardware)
  4. Hiring people to deal with my complexity 🙂
  5. Elevating simplicity as a key factor for my decision making
  6. Decreasing social media footprint.

I’m going to reflect more on this as the year winds down. To be continued.

#MentalNote · Learning · Self-Revelation

Jesus Year

The Jesus Year is age 33, the year that scholars believe Jesus started a spiritual, political, and intellectual revolution. The Jesus Year is the age at which young people decide it is time to get serious about life, time to accomplish something.

I turned 33 at the beginning of April and to be honest, between COVID and some deaths in the family, there hasn’t been much to celebrate. My sister and Crystal mentioned they both do gratitude journals and I thought I’d share out 33 things I’m grateful for this year.

  1. I’m grateful for improving and overall good health
  2. I’m grateful for my parents and their health
  3. I’m grateful for my siblings.
  4. I’m grateful for Crystal.
  5. I’m grateful for my sister-in-law to be.
  6. I’m grateful for my extended family
  7. I’m grateful for my framily and family beyond blood.
  8. I’m grateful I get to do what I love every day at Google.
  9. I’m grateful for what I’ve built at tiphub
  10. I’m grateful for my past mistakes.
  11. I’m grateful for the time I enjoyed in Chicago.
  12. I’m grateful for my mentors that have guided me in this journey.
  13. I’m grateful for all the impromptu adventures around the world
  14. I’m grateful to be alive at this time.
  15. I’m grateful for having the opportunity to teach and share more about product management at General Assembly.
  16. I’m grateful for my car. It’s beautiful.
  17. I’m grateful for the pain and the joy in my life… It’s given everything more color.
  18. I’m grateful for the wisdom that comes with age
  19. I’m grateful Jay – Electronica actually came out with an album and I got to listen to it in my lifetime.
  20. I’m grateful for my time in DC. What a time.
  21. I’m grateful I had the chance to volunteer two years of my life for a greater cause.
  22. I’m grateful for my ability to continue to learn new things.
  23. I’m grateful for the luxury of watching all the bad movies on Netflix.
  24. I’m grateful for my youtube music subscription.
  25. I’m grateful I survived COVID-19
  26. I’m grateful for Jonathan Perrelli. He gave me my first shot at venture capital back in the day.
  27. I’m grateful for all the entrepreneurs I’ve had the chance to collaborate with.
  28. I’m grateful for Moderna.
  29. I’m grateful for Twitter.
  30. I’m grateful for Bollywood and Nollywood movies.
  31. I’m grateful for rainy days.
  32. I’m grateful for Cape Town’s beauty.
  33. I’m grateful for all my DM subscribers.

I’m grateful for all these things and more.

#MentalNote · Education · Politics

The Psychology of Cults

Like most of you, I watched the assault on the Capitol Building with disgust and sadness. For starters, the Capitol Building, when I lived in DC, was right down the street from my apartment. I could feel the enormity of the building every time that I passed it. You see, the Capitol Building is way more than just a building where the US Legislators pass laws. It’s a symbol of one of the three pillars of our government. It’s a standing testament to an enduring idea crafted by our forefathers and passed on from generation to generation.

While we all can agree on some of the main drivers that led to what we saw last week, there’s an underlying belief system / mental state that allowed people to be driven to insurrection. I’m going all the way back to my undergrad for this analysis… One of the toughest but most satisfying classes I’ve ever taken – Advanced Political Theory.

During the class, we studied less about politics and more about psychology, geography, sociology, and history. My professor loved using the analogy of cooking. “Most of your education has been focused on the meal, but if you want to become a chef that makes these meals, you have to respect the ingredients and techniques that put the food on the table.” he’d say. It felt like a defense against the dark arts class… for the Harry Potter fans out there.

We spent a lot of time talking about the psychology of the electorate and what drives people into a tribe-like mentality. We also spent time discussing how tribes can sometimes resemble cults. I had to dig to find my notes but my professor mentioned five truths we should be aware of when structuring in and out-groups and how they can easily turn into cults. For our use, we should be aware of these five truths if we are going to repair The United States and come out better on the other side of this.

* I’m in no way excusing what extreme Trump supporters are doing. I’m just highlighting five truths we should think about if we want to break people free of cults. Also, this isn’t just a US problem. “Radicalization” can happen within religion, politics, socially, etc. These truths tend to hold in all areas.

  1. Life is inherently comfortable and human being’s existence (specifically in the west) is focused on chasing comfort. Cults/Tribes provide comfort in an uncertain world. The world has changed so quickly in such a short time due to globalization, liberalization, and economic shifts. People are being left behind in this changing world and that can be leveraged to drive discomfort. Think about the rhetoric that has been used and what a lot of supporters mention. “Trump hears us.” “We feel forgotten but we now feel seen” Being listened to and remembered creates a level of comfort that can be manipulated if it’s not coming with the best intentions.
  2. Democrats vs Republicans created an in and out-group which that leads to us vs them framing. For some reason, our political affiliation has become one of the most salient parts of our identity, specifically for those who find themselves on the MAGA side of the spectrum. My hypothesis is social media has stripped away location, skin color, economic background and its become the great equalizer for the delivery of ideas. This isn’t to say that these attributes aren’t there, based on social saliency theory, specific attributes just rise to the top. As a result, it’s easier for people to create their own reality because they are talking with people that view their life through the same lens which also reinforces the idea of being heard and a sense of comfort.
  3. Cults tend to deal in absolutes. They provide an absolute way of looking at the world which helps create a more stable foundation. Think about it this way, the world is super complicated with many moving pieces. Some would say it’s even more complicated with the rapid change we’ve seen in the last twenty years. Cults tend to abstract complexity and provide simple explanations of why things are the way they are. This is normally easier to digest and manage for the person who wants to sort through an ever-changing reality. Now abstracting complexities is not all that bad but the process tends to make irrational jumps in logic and truth to create a more simple reality. This is why conspiracy theories and “fake news” is so essential to an absolute perspective. Conspiracy theories provide the framework for abstracted complexities and the fake news defense serves as a moat for any facts that may refute the conspiracy theories and the larger abstracted truth.
  4. Cult leaders are black belts in mind control. Let’s be frank. Trump is a master seller. He used this skill to catapult himself into the real estate industry and several of his other ventures. He leveraged his master skill to get the right people to vote for him back in 2016 and then brought out even more people in 2020. By reinforcing everything we’ve mentioned above, he’s used tactics like brainwashing (reinforcing lies by constantly saying them) and driving paranoia throughout his ranks. Trump did a great job of convincing people that the other (Everyone against him) and/or the government is out to get them, but his rallies and his group can provide safety. Once someone concludes that the “other” and country cannot keep them safe, they begin to worship and put all of their faith in the person who provides comfort and protection.
  5. Cults tend to focus on total control and less on optionality. If you’re controlling a person’s reality, allegiances, perspectives, and mobility, you might be leading a cult. Seems like control was an under-current for MAGA and a lot of Trump rhetoric. As a result, a subgroup of people answered the call to storm the Capitol Building in DC and other legislative buildings throughout the United States.

Once again, this isn’t to excuse. To use my professor’s analogy, we need to understand the key ingredients that led to the food we’re forced to serve. Even in this explanation, I’m sure you can see some areas where the private sector and the US government can drive reform to ensure this doesn’t happen again.

Education · Leadership · Politics

The Montgomery Bus Boycotts: Evaluating Social Change With A Change Management Framework

While I was in business school, I wrote this analysis on the Montgomery Bus Boycotts for our Change Management class. After reading it again, I thought it was really pertinent to thinking sustainability of social movements in the age of #BLM #ENDSARS and similar movements all throughout the world.

Introduction

The Montgomery Bus Boycott was one of the largest and longest mobilizations of a community in the history of the civil rights movement. It set the standard for how major players like Martin Luther King, the NAACP and other organizations would mobilize, and effectively communicate and coordinate civil disobedience protest strategies all across the country. However, there are many questions and underlying topics that surround the Montgomery Bus Boycotts. Why Rosa Parks? What was the Montgomery Bus Boycotts looking to achieve? Was the Montgomery Bus Boycotts successful? In the following essay, I will explore many of these questions through the lens of change management theory.

Background

Late in the afternoon of Thursday, December 1st, 1955, Rosa Parks leaves work at the Montgomery Fair department store and boards a bus home. The bus fills up. A white man boards — but with no seats available he has to stand in the aisle. The bus driver orders the four front-most Blacks to surrender their seats so he can sit. Mrs. Parks recalls:

At his first request, didn’t any of us move. Then he spoke again and said, “You’d better make it light on yourselves and let me have those seats.” … When the [other] three people … stood up and moved into the aisle, I remained where I was. When the driver saw that I was still sitting there, he asked if I was going to stand up. I told him, no, I wasn’t. He said, “Well, if you don’t stand up, I’m going to have you arrested.” I told him to go on and have me arrested. He got off the bus and came back shortly. A few minutes later, two policemen got on the bus, and they approached me and asked if the driver had asked me to stand up, and I said yes, and they wanted to know why I didn’t. I told them I didn’t think I should have to stand up. After I had paid my fare and occupied a seat, I didn’t think I should have to give it up. They placed me under arrest then and had me to get in the police car, and I was taken to jail… — Rosa Parks. [1]

Rosa parks is then taken to jail and through a network of well connected friends, her bail is paid and the news of her arrest spreads like wildfire throughout the Montgomery community.

That night, students from the college nearby started making fliers that called for a one day bus boycott the next Monday. Friends of Rosa Parks start to build coalitions and develop the Montgomery Improvement Association (MIA) to lead the charge against Montgomery. Nixon, Rosa Parks friend and community leader within the NAACP, appoint a young pastor, Martin Luther King, as head MIA because he’s a young outsider who is not entrenched in the politics of the church establishment.

On Monday, December 5th, 1955 the bus boycott began. People walked to work, carpooled where they could and took taxis. That same day, Rosa Parks was charged with violating the segregation law and faced a $14 dollar fine. Due to the verdict and a successful one day boycott, the leadership decided to continue the boycott. For the next year, MIA coordinated with Montgomery community organizations to sustain the bus boycott through facilitating carpool routes, leveraging taxi services and coordinating other resistance strategies. When Montgomery didn’t change their segregation policy, lawyers associated with the MIA and NAACP chose to file a federal lawsuit challenging the constitutionality of the Montgomery segregation laws.

In June 1956, the federal court in Montgomery ruled in Browder v. Gayle that Alabama’s bus segregation laws, both city and state, violated the Fourteenth Amendment and were unconstitutional. The U.S supreme court upheld the decision later that year. In December, after an estimated $250,000 in lost bus revenue and millions in lost tax revenue and retail, the Montgomery Bus Boycott finally came to an end. 

Analysis

As a result of the Montgomery Bus Boycott, civil rights leaders are finally given a tangible model on how to facilitate change in society. While many of the concepts of nonviolence and civil disobedience are based in the teachings of Gandhi and Jesus Christ, there was no real macro model which mobilized institutions and coordinated people in the way that would amount to change. Ultimately, change in the civil rights movement was three fold. For the sake of simplicity, I’ll focus particularly on the Montgomery Bus Boycott. The three major changes include

  1. Transition from individual to community action
  2. Economic concept of equality
  3. Change in the laws that perpetuated segregation

Transition from individual to community action

Rosa Parks wasn’t the first person to be arrested for not giving up their seat on a bus in Montgomery. Based on our reading in The Power of Habit, there are three things that lead to the full out bus boycott.

“A movement starts because of the social habits of friendship and the strong ties between

close acquaintances. It grows because of the habits of a community, and the weak ties that hold neighborhoods and clans together. And it endures because a movements’ leaders give participants new habits that create a fresh sense of identity and a feeling of ownership.” -Power of Habit pg 155

Duhigg argues that the reason Rosa Parks sparks the Montgomery Bus Boycotts is because of her close varied connections throughout the community of Montgomery. She has a diverse group of close friends that vary in profession, social status and interests. Once they hear about how their friend had been arrested, they are more likely to act and bring other close friends to action.

We see this play out in how easily accessible organizations like the NAACP, college professors and church members became throughout her story. This doesn’t play out the same way for others who were arrested. The power of Rosa Parks network galvanizes friends to feel directly offended as if they were the ones that were arrested. “If it happened to Rosa, it could happen to us.” This energy is leveraged to facilitate the actions steps that mobilize the whole community for the boycott.

Another spark that helps facilitate larger community action is the emergence of the Montgomery Improvement Association and of Martin Luther King’s leadership. Unless E.D Nixon was reading change management strategy 20 years into the future, he was ahead of his time when he suggested that Martin Luther King head the newly formed Montgomery Improvement Association. There were three very important characteristics that Martin Luther King possessed that made him an ideal candidate. Most importantly, he was a new member of the Montgomery community that was just starting to establish his identity and his church. He was younger than most of the ministers, so he had the energy and electric emotion to lead a group of people. Lastly, he was minister, which gave him the language to speak to a mass audience that was predominately Christian in belief.

Martin Luther King uses his newly appointed role to rally people around the concepts of civil disobedience and brotherhood. He unites people by consolidating the message and making it appeal to everyone. While MLK is effectively communicating for the bus boycott, MIA is developing the infrastructure to support the logistics for a yearlong battle. MLK brings people together through integrating non-violence into Christian doctrine and ties a people to a larger cause than themselves. The MIA creates new habit for the Black community in Montgomery that include walking to work, carpooling and taxi services. The organization and higher calling are what ultimately sustains the Montgomery bus boycotts for a year.    

Economic concept of equality

The Montgomery Bus Boycott was one of the largest mobilizations of a particular group in history of the United States. While there was segregation was at the center of the Montgomery bus boycotts, there was a more basic fundamental that one person’s 10 cents are worth the same amount as the next persons. The Black population in Montgomery was about 40,000 people. Blacks represented more than 75% of the ridership on the bus system. Imagine losing almost 75% of your ridership for a year. For a long time, there was a racial hierarchy/value given to money from whites versus blacks. The bus boycott was the first major example of how much economic power a community could have if they came together. Anyone with that large of a purchasing power cannot be ignored. Thurgood Marshall has been quoted saying that the Montgomery bus boycotts were won through the courts and not through the boycott in which he is technically correct. However, the hearts, minds and pockets of merchants, drivers and administration had already been pushed to the edge. The financial implications of the boycott were too enormous not to ignore but ultimately, for the first time, people became aware of how much spending power the black community had. The black community saw this as well and quickly replicated similar strategies all around the country.

Change in the laws that perpetuated segregation

Social norms play a significant role in determining legal structures. In the common law perspective, most laws are derived out of a set of common norms (core Christian values) Social norms that are normally entrenched in society for an extended period of time eventually convert into legal frameworks to sustain the social norms past societal changes. When Black leaders in Montgomery county started discourse to prepare a legal case against the city of Montgomery and Alabama segregation laws, they were battling a legacy of social hierarchy, through and policies were relics of southern society pre- civil war. These laws were put in place to institutionalize a mindset that decreased the rights of blacks positioned whites as the hegemonic power in the south. Ultimately, this was the long term, sustainable change that the Black community in Montgomery, AL mobilized and fought to reach.

Montgomery Bus Boycott through a change management perspective

After research on the Montgomery Bus Boycott and applying some of the change management theories we’ve learned in class, I found that the Montgomery bus boycott is not only an exact fit within the Kotter model, but a more integrated application. In this next section, I will break down the Kotter model and explain for each section how the Montgomery bus boycott applies.

Establish a sense of urgency

Upon Rosa Parks arrest, her mother quickly calls all of her friends and from there the sense of urgency is born. Imagine hearing that one of your friends was in jail for a crime that might have landed you in jail as well. Many of Rosa Parks friends mobilize the resources and people needed to not only get her out of jail but facilitate the boycott. This is an example of perfect place and perfect timing. Civil rights leaders are more equipped to establish a sense of urgency here because of Rosa Parks role in the community. She is very connected and helps to bring a diverse group of people together that normally wouldn’t be in the same group at any other time. By leveraging a perfect opportunity, the sense of urgency is timing. Its an opportunity to get back at Montgomery bus system for disrespecting “one of our own” .

Create a Guiding Coalition

During the development of the Montgomery Improvement Association, Nixon pushes for Martin Luther King to be the face, leader, and voice of the organization, thus making him the head leader of the Montgomery bus boycott. The creation of the Montgomery Improvement Association is the first step in building a guiding coalition, but the most important move was placing Martin Luther King as head of the organization. As I mentioned previously, MLK’s position in the community, in all facets, makes him an ideal candidate to lead the Montgomery Improvement Association. He’s an outsider, young and a minister. These three characteristics play an intricate role in his ability to reach the masses and made him one of the most effective leaders in the civil rights era.

Develop a Vision and a Strategy

The MIA was the operational tool of the Montgomery bus boycott. They developed a message and strategy that MLK stated:

“I want it to be known that we’re going to work with grim and bold determination – to gain justice on the buses in this city. And we are not wrong. We are not wrong in what we are doing. If we are wrong – the Supreme Court of this nation is wrong. If we are wrong – God Almighty is wrong! And, we are determined here in Montgomery to work and fight until justice rolls down like water and righteousness like a mighty stream!” [3]

MIA developed a goal that eventually stalled negotiations they were:

  1. Treat Negroes with greater courtesy
  2. Hire Negro drivers for Negro routes
  3. Desegregate bus seating.

The overall strategy was two prong. Blacks would boycott the bus system until demands were met and Black leaders would look for ways to challenge the legality of the policy in higher courts.

Communicate the Change Vision

I believe that this is the true differentiator that takes the Montgomery bus boycott and makes it sustainable. It all goes back to the selection of Martin Luther King as the head of MIA. There were major pieces of social change entangled in the boycott but King’s knowledge in Christianity and his ability to mold the conversation and the message makes it palpable and translatable to audiences outside of the black community. Even within the black community in the south, the church is the cornerstone of society and appeals to the masses. King takes many of the ideals and messaging and integrates in into his sermons and applies scripture as arguments for equality. It’s the equivalent to some of gummy vitamins, masked in something you know and enjoy but inside is something that’s really good for your body. In my opinion, this is what gives the civil right movement the legs it needs to be replicable and appeal to those that are who are not black but share Christian values.

Empower Broad Based Action

Montgomery Improvement Association was the central hub of logistics during the early periods of the Montgomery bus boycotts. However, the boycott is sustained once people start taking ownership and start to own that they are individually boycotting the bus system. This is when you start to see weekly block meetings setting up logistics for how people will get to work, and other people start to move into management/leadership roles within the organization. The ultimate goal of empowering broad-based action is that the change agent doesn’t have to be the person enacting or facilitating the change vision and strategy. MIA achieved this by getting buy in early in the process and through the effective messaging by Martin Luther King that pressed a message of long-term benefit and endurance. (Most of the time, embalmed in Christian doctrine.)

Plan and Generate Short-Term Wins

The most effective short-term win was the one-day boycott developed by MIA and Black leaders. Once people saw how feasible it could be to continue the boycott, it almost seemed logical to continue until demands were met. This is also another interesting step that was altered due to the selection of MLK. As a minister in Christianity, it is easy to preach postponing immediate gain for long term wins as long as people are constantly aware of the long-term goal. I also believe that the belief in delayed gratification is what also sustained the Montgomery bus boycott for as long as it did. There were still short-term victories, but MIA and MLK did a great job of celebrating the small victories that did occur and managing expectations for the long term.

Consolidate Wins and Produce More Change

For all intents and purposes, the black community in Montgomery was winning the boycott. The bus system was losing thousands of dollars a day, retailers were losing out on income and Montgomery was losing out on tax income. However, in order to truly win and produce the maximum amount of change, MIA negotiated with the city of Montgomery to alter their segregation policies. After stalled negotiations, MIA and the NAACP decided to make a legal case for the unconstitutionality of Montgomery and Alabama’s policies.

Anchor the New Approaches in the Culture

The supreme court ultimately rules that Montgomery and Alabama’s laws are unconstitutional under the 14th amendment. As previously stated in the paper, laws are social norms that have been agreed upon as the common actions/ policies toward citizens. By challenging and having the segregation laws overturned, the law sets a whole new precedence by which other laws can be exploited and changed. Ultimately, the supreme court ruling ensures the longevity of the essence of the Montgomery bus boycott.

Conclusion

While the Kotter model is a great fit to the Montgomery bus boycott, there are great lessons to be learned from one of the most pivotal boycotts in the history of our country. Most importantly, your change thesis has to be palatable to your champions but eventually has to get through to the enemies of change. MLK was great at taking civil rights arguments and integrating concepts into Christianity. By doing that, it disarms most of the arguments the opposing side uses. It’s important when facilitating change, you pick leaders in the change coalition that speak the language of the masses and effectively know how to communicate a streamlined message. Secondly, momentum is significantly important in establishing a sense of urgency. The effectiveness of Rosa Park’s network is only utilized in the moment. If the boycott started a week after, it wouldn’t have had the same adoption rate. Building of a momentous occasion builds a larger case for the sense of urgency. Lastly, change isn’t just a change in habit or beliefs, but it needs to be founded in policy and governance. The Montgomery bus boycott is successful because it changes the hearts and minds of a majority of the people involved but the defining and sustaining success lies in the policies being declared as unconstitutional. In organizational change management, its important to facilitate change but sometime the best way to facilitate change and sustain it is through policy and governance interventions. The Montgomery bus boycott would serve as model for future civil rights battles all across the country. While certain elements couldn’t be replicated, the core served as a great model for leaders to apply.

Bibliography

Berg, Allison,“Trauma and Testimony in Black Women’s Civil Rights Memoirs: The Montgomery Bus Boycott and the Women Who Started It, Warriors Don’t Cry, and From the Mississippi

Boycott. DVD, directed by Clark Johnson. Los Angeles: Home Box Office, Inc., 2001.

Burns, Stewart, ed. Daybreak of Freedom: The Montgomery Bus Boycott. Chapel Hill: University of North Carolina Press, 1997.

Duhigg, Charles The Power of Habit Random House LLC, Feb 28, 2012

Eyes on the Prize: Awakenings (1954-1956 ). DVD, directed by Henry Hampton. Boston: Blackside, 1987.

Gray, Fred D. Bus Ride to Justice. Montgomery: Black Belt Press, 1994.

King, Martin Luther, Jr. Stride Toward Freedom. New York: Harper, 1958.

Robinson, Jo Ann Gibson. The Montgomery Bus Boycott and the Women Who Started It. Knoxville: University of Tennessee Press, 1987.

Thornton, J. Mills III. Dividing Lines. Tuscaloosa: University of Alabama Press, 2002.

#MentalNote · communication · History · Leadership · Movies · Technology · venture capital

Overcoming Collaboration Trauma

I try to write and post by Friday but this topic had a lot of angles and research involved so I thought I’d take the weekend. Here we goooo.

Collabo

Earlier this week, I was on a call with a group of black founders thinking of collaborating in a major way. (More details to come) During the meeting, one of the founders said something that I’d never heard before. “ As we work together, we have to understand that many of us have “collaboration trauma” and we need to be cognizant of that as we find new ways to collaborate.”

After the meeting, I went down a rabbit hole trying to figure out if there was any information out there on collaboration trauma and I used my google-fu to find research or articles mentioning collaboration trauma. I couldn’t find anything significantly substantial.

Taking a step back, I walked through my experiences with collaboration to better understand what they meant….Some background for those who still wonder what I do for a living.

  1. I work at Kohactive as a product manager. I help companies build software products for internal and external usage. Yes, that is me on the first page.
  2. I teach at General Assembly as a part-time instructor – I teach product management twice a year.
  3. I invest and advise early-stage startups at the intersection of technology and impact at tiphub.vc
  4. I assist my father with his ventures in Sierra Leone, Nigeria, and Kenya.

Collaboration, in most of my work, is essential to unlocking significant value for the parties involved. But with certain areas, there’s a lot of structures that are repeatable and trustworthy which makes collaboration easier.

For example, as a product manager at Kohactive, there are processes and methodologies in place for me to leverage to ensure I’m working well with designers, engineers, users, customers, etc. I rely heavily on those processes to make sure there’s maximum collaboration.

As an instructor, there’s a standard norm of teacher/instructor to student. I spend most of my time navigating that predefined role in order to create a positive experience for students. On my end, I look at it as getting paid to learn about different industries.

With tiphub, there’s a lot of collaboration opportunities but this is where most opportunities fall through. Most of the time, I’m caught taking meetings / having conversations that make me feel like I’m stuck in a power struggle. I feel like there’s someone who is trying to finesse me or I’m getting the better end of the transaction.

Working with my father is a total crapshoot. Sometimes it hits and sometimes we get burned. But over time, there are wins.

Epiphany: The Prisoner’s Dilemma

The Prisoner’s Dilemma came to mind as a great mental model to think through strategies of collaboration. (I finally get to show I learned something in econ class.) Here’s a quick rundown:

The Prisoner’s Dilemma is a subset of Game Theory that explores the incentives for collaboration between two actors. It was originally framed in the 1950s with this scenario:

Two members of a criminal gang are arrested and imprisoned. Each prisoner is in solitary confinement with no means of communicating with the other. The prosecutors lack sufficient evidence to convict the pair on the principal charge, but they have enough to convict both on a lesser charge. Simultaneously, the prosecutors offer each prisoner a bargain. Each prisoner is given the opportunity either to betray the other by testifying that the other committed the crime, or to cooperate with the other by remaining silent. The possible outcomes are:

  • If A and B each betray the other, each of them serves two years in prison
  • If A betrays B but B remains silent, A will be set free and B will serve three years in prison
  • If A remains silent but B betrays A, A will serve three years in prison and B will be set free
  • If A and B both remain silent, both of them will serve only one year in prison (on the lesser charge).

There’s a ton of research on this but one of the best examples of the prisoner’s dilemma is in the movie Dark Knight. Just to give a little more context, during the movie, activities facilitated by the Joker cause two ferries, one full of prisoners that Harvey Dent and Commissioner Gordon locked up and the other full of other people, to escape the city on a boat.

While sailing off, the two ferries lose all power and their engines die. Both ships realize there are explosives all about the boat, and they both find detonators. It is at this time that the Joker’s voice is heard over the loudspeaker of both ferries, and he informs them that they are part of a social experiment. The detonator on each boat is for the other boat.

One ferry must press the button and destroy the other boat by midnight, or else the Joker will destroy both boats. This drags out for a while, but eventually, people in the ferry decide not to blow the other boat up.

If you’re interested- here’s the scene in how it plays out at the end:

Probably on the top 10 list for best movies of all time, this scene encompasses so much.

The Joker, as he’s swinging back and forth, said, “Until their spirit breaks completely.” (keep this in mind, we’ll need it later)

One of the major areas of research in the prisoner’s dilemma is focused on incentives for collaboration. This is best evaluated in a matrix.

The dominant strategy for a player is one that produces the best payoff for that player regardless of the strategies employed by other players. The dominant strategy here is for each player to defect (i.e., confess) since confessing would minimize the average length of time spent in prison.

The payoffs make sense in different scenarios. For example, imagine playing 100 rounds and you don’t know how the person will interact. Tit for tat might become the more effective route.

In reality, there are ways to skew outcomes for effective collaboration. For example, #nosnitching law in the streets ensures you understand what to do if you end up in a cooperate/ defect scenario. Standards and norms, in certain scenarios, set up the way we should play the game. In my work life, instructors vs students roles encompass norms that help us understand the best way to collaborate. Even in product management, agile sprints, user stories, wireframes…etc, all of that are tools to engage in more cooperative outcomes for stakeholders.

As I start to look in other areas, specifically in finance and business development, there’s a lot of tailwinds to effective collaboration. For example, there are fewer norms around cooperation when you’re figuring out how to create untapped value. There’s less trust. And in low trust environments, people tend to operate in their own best interest and have no real incentive to collaborate.

This takes me back to what the Joker said in the clip; “Until their spirit breaks completely.” He was responding to Batman’s assertion that people are inherently good and will choose to cooperate over and over again. I believe Joker was onto something, at a certain point people would get fatigued from cooperating and not getting the same incentive as they should. They lose trust in the game and eventually decide to set up a new game with better players, or they play a whole different game.

Collaboration Trauma

Often times black founders who are building startups in the tech space are operating in low trust environments for several reasons:

  • A smaller amount of resources: Less than 1% of venture capital goes to Black founders. (To give you perspective, there was 34 billion USD of venture capital investments done in 2020 Q1) Most founders are in hyper-competition for resources. So the incentive for collaboration might be misaligned.
  • Knowledge/ information asymmetry: Black founders in tech are operating in spaces where they have been systematically shut out. As a result, the knowledge of the processes or communities that help facilitate trust and increased likelihood of cooperation is not available. Ultimately, black founders in tech end up in less cooperative scenarios.

I’m sure there are other industries where this happens. I’m sure there are other groups that are shut off from opportunities in way that leads to, as the Joker described, a broken spirit. This is the trauma that many disenfranchised groups carry with them when they think about collaboration.

So how do we fix it? Well at tiphub, we’ve definitely identified this problem and we’ve started to realize transparency is one of the largest impediments to collaboration. So we’ve really been focused on how we can work on exposing things we normally wouldn’t think to share. For example, we have a playbook where we walk through every process about our company and how and why we make decisions. If you want to read more – read here .

We made our playbook open source. We’re also going to start releasing data on our programs and benchmarks to everyone. A lack of transparency and process is the best way to ensure collaboration is difficult. We’re on a mission at tiphub to increase our success rate by sharing already existing frameworks and making sure everyone has the information needed to increase trust and collaboration.

If we’re going to increase the likelihood of more equitable collaboration in our organizations and interactions, we have to look for those spaces where there’s gray area and work to bring process and transparency as much as we can. If we don’t, we’ll continue to stifle collaboration and perpetuate less optimal outcomes.