Six Lessons Entrepreneurs can learn from the six championships of the 90’s Bulls

As a kid growing up in the Chicago area in the 90’s, the Bulls weren’t just a huge part of my childhood — they were my childhood. Going to the Chicago Stadium, and later the United Center, to watch the Bulls was better than Christmas and Birthdays combined. I spent hours in my driveway working on the MJ fadeaway and the ‘switching hands’ lay-up, dreaming of someday playing in the NBA.

Unfortunately, due to my height and overall skill level, the NBA never called. Years later, however, I was given the gift of re-living these ‘glory days’ of my childhood vis-a-vis the ‘Last Dance’ documentary. In diving into the documentary, with the benefit of having worked with startups and in VC for a number of years, I couldn’t help but notice the parallels in the journey that the Bulls took to build a dynasty and the journey that many startups embark on when building successful companies.

I used this as an excuse to write about two of my favorite topics — the 1990’s Chicago Bulls and building startups. Here are 6 lessons from the 6 championships of the Bulls that startups can use when building their companies:

1) Sometimes, a new leader may need to come in to take the group to the promised land

When Michael Jordan was drafted in 1984, the Bulls were cellar-dwellers of the NBA. They were outdrawn in attendance at the Chicago Stadium by an indoor soccer team. Two years into Jordan’s career, the Bulls brought in Doug Collins to coach a young MJ and the Bulls. Collins ran an offense centered around MJ — allowing Jordan to grow into one of the game’s most prolific scorers, a feared defenders, and gain the confidence that he was one of the game’s best players; however, the Bulls could never get past the Pistons in the playoffs.

In 1989, the Bulls hired first-time coach Phil Jackson. He brought a different perspective to the game, instilled a Zen-like culture and implemented the Triangle offense — in which any one of the 5 players on the floor could be a threat to score — thus, empowering Jordan’s teammates. Jordan’s scoring numbers took a step back, but the rest of his game flourished. In 1991, the Bulls finally got over the hump and won the first of six championships.

In the startup world, leadership changes are not uncommon. Different stages of a startup’s life cycle requires different skill sets. In the early days, the CEO has to wear multiple hats. Perhaps most importantly, they are always selling — whether it be to customers, new hires, partners or investors.

Once a company gains traction, an additional set of skills is required, including: scaling sales and operations, hiring, managing investors, employees and a board, and driving the company to an exit, to name a few. It’s a tall task to find someone who is skilled in all areas of all stages of a business, so often times, a leader will either need to find others to augment the management team, or sometimes step aside altogether for the best long-term interests of the company.

2) Understanding what motivates people on an individual level is key to getting maximum performance

Coach Phil Jackson was a master at connecting with every member of the Bulls on a personal level. He knew what each individual needed in order to maximize their performance.

When Dennis Rodman came to the Bulls in 1996, he was coming off of a relatively unsuccessful stint with San Antonio. Rodman made a splash early in his career with Detroit Pistons under the late Chuck Daly. Daly took Rodman under his wing and had a ‘father-like’ love for Rodman. After Daly left the team, Rodman became despondent. In San Antonio, there was little love or compassion shown to Rodman from the coaching staff or players; however, when he came to the Bulls, he fit in ‘like a glove’ according to Scottie Pippen. He was embraced by coaches and his teammates. Phil Jackson gave Rodman the love, respect and leash that he needed, so much so that — against conventional coaching wisdom — he allowed Rodman a one-week hiatus from the team in the middle of the 1997–98 season to go on a multi-day trip to Vegas. This change in culture maximized Rodman’s motivation and passion — he again became one of the league’s best defenders and rebounders.

For Michael Jordan, what motivated him was his insane competitiveness, desire to destroy his competition and a hatred for losing. During scrimmages, Phil would often stop midway and move Jordan to the losing team. This would light a fire under Jordan, who lit a fire under his teammates to maximize their performance.

In the early-stage startup world, cash is often a big constraint. It is important for leaders of the companies to dig deeper with their employees and understand them as people. Why are they working for your company? What incentives will enable them to go above and beyond?

Employees are usually working for startups for reasons beyond just a salary. It could be the Company’s mission, the ability to learn a variety of skills, the flexibility in schedules, equity ownership, the ability for one’s work to make a visible impact. Understanding at the individual level, what motivates an employee, will help you, as a leader, craft experiences and perks that keep employees loyal.

3) You have to constantly adapt to stay ahead of the game and the competition

The Bulls struggled in the late 1980’s to get past the Pistons in the Eastern Conference playoffs. Year after year, the Bulls would meet the Pistons in the playoffs, get physically dominated and abused, and go home early. Ahead of the 1990–91 season, Jordan and the Bulls committed to weight training — something they hadn’t focused on before. At the time, the NBA was more physical than it is today, so the Bulls had to adapt. And it worked — they beat the Pistons in 4 games in the Eastern Conference Finals and never looked back.

During the second three-peat, MJ began to wear down physically. It was more difficult to beat younger, faster players to the basket and hang in the air for hours on end. MJ had to adapt. Enter: the fadeaway. MJ developed his patented post-up fadeaway that was unblockable at the time and probably still is today.

This constant adaptation was key to the Bulls’ dominance in the 90’s — and it is also key for startups when competing in crowded markets. The best companies talk to their customers every day and are always looking for an edge. They are constantly defining and redefining customer needs and personas, exploring new ways to reach customers and developing innovative ways to leverage the Company’s strengths to solve their customers’ biggest pain points.

As the old saying goes, ‘evolve or die.’ The Bulls were never complacent despite their success, and startups that employ the same mentality are often destined for greatness.

4) A) For every great Batman, there is a Robin

The Bulls wouldn’t be the Bulls without Scottie Pippen. He was the Robin to Jordan’s Batman. The two fed off of each other. Like MJ, Pippen could do it all — score, pass, rebound, play the point guard position, and, most importantly, he could man up the opposition’s best player. The problem before Pippen was that Jordan was asked to do it all — score, rebound and guard the opposing team’s best player — and doing this for 82 regular season games took a physical toll on MJ. Having a strong #2 to lean on allowed Jordan to maximize his strengths that the Bulls needed in order to defeat the opponent at hand.

A good founder and CEO knows that they need a strong Pippen-like performer — and sometimes even two. For technical founders/CEO’s, it may be a business-minded co-founder who can direct go-to-market strategy and land sales. For non-technical CEO’s, it may mean a strong technical co-founder who can execute on a product vision.

As a startup progresses beyond a seed stage, while the CEO is often great at mapping the vision, setting the strategy and executing on big sales and partnerships, they need someone to manage operations, help with hiring, be a wingman on sales calls or be a sounding for strategic decisions.

As CEO, you might be the best at a variety of different aspects of the business, but in order to use your time wisely and maximize the value of your company, you need to be skilled at off-loading some of the tasks to other team members.

It’s hard to go all the way as a one-person show.

B) A successful team is well-rounded and everyone understands their roles

Sure Jordan received much of the accolades during the Bulls run in the 90’s (and deservedly so!), but he is the first to tell you that he didn’t reach the heights of a champion alone. In fact, it wasn’t until Jordan’s seventh season in the NBA that he won a championship.

What changed? In addition to his own improvement, the team around him improved drastically — and were extremely well-rounded. Throughout their dynasty, in addition to the GOAT, the Bulls had: the best #2 of all time in Scottie Pippen; strong rebounders and defenders like Dennis Rodman and Horace Grant; three-point specialists like John Paxson, BJ Armstrong and Steve Kerr, and one of the most well-rounded 6th men of all time, Toni Kukoc.

Just like every member of the Bulls roster had a role and a purpose, startup teams should be built in a similar fashion. Every hire is crucial at the early stage, and it is important to complement the skills that the company already has.

In an often cash-constrained environment (similar to a salary cap), the first step is to take a radical inventory of the Company’s strengths and weaknesses and then match them up to the Company’s needs given its stage, its place in the market and the highest priorities over the next year. Sometimes this may mean outsourcing certain functions vs. hiring internally, but filling gaps where a startup is weak is one of the keys to success.

5) A leader needs to empower his or her teammates and embrace ‘letting go’

In Game 5 of the 1991 finals, the Lakers led 93–90 in the fourth quarter. Jordan was trying to take control of the game by scoring every time down the floor. During a timeout, Phil Jackson pointed out that the Lakers were double-teaming MJ and leaving 3-point guru John Paxson wide open. Coming out of that timeout, Jordan began to look for Paxson. The Bulls went on a 9–0 run. Paxson scored 10 points in the final 3:24 of Game 5, leading the Bulls to their first NBA championship.

Jordan was used to putting the Bulls on his shoulders and willing them to victory. In this case, in the most important time for the Bulls, he became the facilitator and empowered his teammate to help the Bulls win.

It is very easy for founders and CEO’s to want to take over and do things ‘their way’ — especially when times are stressful or time sensitive. However, for founders and CEO’s, their time should be spent on the highest value tasks. Getting bogged down in the weeds or minutia eats into the time that could be spent on things like talking to customers, selling and fundraising.

6) Beware of egos and politics

Arguably, the downfall of the Bulls can be tied to ego and politics. Whether it was the late GM of the 90’s Bulls, Jerry Krause, threatening to trade key players and forcing Phil Jackson out as head coach, or Scottie Pippen delaying surgery because he was the most underpaid player in the NBA — there was always drama surrounding this team.

The root cause of these issues was that the Bulls were so successful, that key people in the organization felt like they were not getting as much credit as they should have. Krause, who put the team together, was famously mocked by Jordan and Pippen and booed by fans. Pippen harbored anger and resentment that the Bulls would not renegotiate his contract, despite the fact that he was one of the top players in the NBA.

One of the benefits of a startup is that you don’t have to deal with the politics that reign in a large corporation. As startups and teams grow, however, it is easy to lose control of the ‘startup culture.’ It is vital that as the company grows and becomes more successful, the early employees who helped get it there are rewarded properly (see #2).

In many cases, it should be a top priority for fast-growing startups to make the ‘Head of People/HR’ a top priority hire before going on a hiring spree. This person can be charged not only with hiring, but making sure that everyone feels appreciated and that politics are left at the door.

The Bulls of the 1990’s were the greatest team of all time. Many of the underlying principles that made them successful — a strong culture, a well-rounded team, adaptation and skillful leadership — can be applied to startups trying to build their own dynasty.