Startups – improv and all that jazz

I’ve been a clumsy, enthusiastic saxophone player for several years now, able to knock out a few recognisable tunes and get folks’ toes tapping. They say ‘don’t play the saxophone, let it play you’ – but sometimes I just can’t get a decent sound out and it sounds like a deranged parrot. As Miles Davis said, ‘Anybody can play. The note is only 20%; the attitude of the person who plays it is 80%’ – so I continue to give it a go.

As part of learning the sax, you have to be able to improvise, playing jamming ‘free flow’ sessions to stretch your style, and speed of thought, playing chord progressions as spontaneous practice. Alas my concrete fingers constrain my dexterity, but playing sax is fun, relaxing and energises me.

My favourite saxophonist is the late American John Coltrane, also known as Trane. Coltrane pioneered the use of modes in jazz and was at the forefront of free jazz. He played with some of the greatest jazz exponents, including trumpeter Miles Davis and pianist Thelonious Monk.

Growing up in North Carolina, in the 1930s, he benefited from a musically family: his mother sang and played piano; his father played clarinet and violin. But during his seventh grade, Coltrane’s fortunes took a tragic turn. Within six months, his maternal grandfather, father, and maternal grandmother all passed away. John became tortured by his inability to remember what his father looked like. In this emotional vacuum, Coltrane threw himself into the alto sax.

When his family moved to Philadelphia in 1943, Coltrane found himself in a cauldron of jazz and a breeding ground of the hard bop style. He soon began a journeyman’s life, gigging with cocktail trios and R&B combos. At the Granoff Studios in Philadelphia, he took a course of music theory and lessons. Coltrane arrived early in the morning and remained through the evening.

Practicing at home, as the night wore on, he would finger but not blow into the instrument so that he could quicken his reflexes without waking his neighbours. Coltrane’s perfectionism was legendary. Borrowing exercises from a pianist, he stunned fellow musicians by forcing his fingers to navigate arpeggios, trills, and wide leaps in melody.

In 1955 his career took off. Miles Davis hired Coltrane into his quintet, gambling on a 29 year-old with a jagged style and a heroin habit. The quintet’s albums Round About Midnight and Cookin’ were landmarks, but Davis grew aggravated with Coltrane’s unreliability. In 1957 Davis fired him.

The dismissal was a shock. In its aftermath, he experienced what he called “a spiritual awakening” and quit drugs and alcohol. Under the influence of pianist Thelonious Monk, Coltrane started obsessing over harmonic variation. “I would go as far as possible on one phrase,” he said, “until I ran out of ideas.” His style was dubbed “sheets of sound”.

With modal forms, Coltrane found a way to combine side-slipping chromatic movement with more lyrical lines. The end result was the sound of a saxophone flitting, hovering, baiting the rhythm section, then colliding with it head-on in a moment of harmonic convergence.

His greatest recording success, A Love Supreme (1964), was a jazz blockbuster with over a million copies sold. It solidified Coltrane’s innovator status. In one of jazz’s defining moments, Coltrane conjugated its leading four-note motive through every register and key, then gravitated back to the original key to chant the four-syllable mantra, “a love supreme.”

After A Love Supreme, Coltrane went further with his experimentation. His music became even more exploratory, dropping the rhythmic pulse that had structured even his most wayward previous ventures. Coltrane began bridging out to a new generation of free jazzers. And then, on July 17, 1967, he died of liver cancer.

To truly know Coltrane’s work is to hear every note in context, my favourites being his chord substitution cycles known as ‘Coltrane changes’, heard on Giant Steps, generally considered to have the most complex and difficult chord progression of any jazz composition. His development of these altered chord progression cycles led to further experimentation with improvised melody and harmony that he continued throughout his career.

Coltrane’s rich productivity of releases left behind a considerable body in unreleased work that has been posthumously issued. He won the 1981 Grammy for Best Jazz Performance for Bye Bye Blackbirds, a live recording made in 1962, and he was given the Grammy Lifetime Achievement Award in 1992, twenty five years after his death. Coltrane lives on, in 100 albums on iTunes.

Coltrane was a jazz entrepreneur, he did what any startup leader does: he improvised, inventing novel responses and taking calculated risks without a scripted plan or a safety net on any guaranteed outcomes. Coltrane didn’t dwell on mistakes or stifle ideas – like entrepreneurs in today’s hurried, harried, innovative and fertile world of startups, he made it happen.

Coltrane believed that musical creativity was an act of discovery. He knew that spontaneous creativity was the business of jazz. With less than 1% of the notes on the written page, he made up the rest on the fly – no going back to correct mistakes or rethink a passage.

In his revelatory book, Yes to the Mess, jazz pianist and management student Frank Barrett shows how this improvisational ‘jazz mind-set’ and the skills that go along with it are essential for effective startup leadership. He describes how like skilled jazz players, startup leaders need to master the art of unlearning, perform and experiment simultaneously, and take turns soloing and supporting each other.

So let’s look at the lessons startup entrepreneurs can take from Coltrane:

Playing it safe gets you nowhere If you don’t take risks you’ll never excel. Playing it safe all the time becomes the most dangerous move of all. Rote activity doesn’t lead to the path of innovation for disruptive technology.

Jazz follows a basic chord progression with a simple beginning, middle and end. In startups, we also start with minimal structures. Iterations begin as prototypes progress and then final aesthetics, allowing us to identify what works and what doesn’t throughout the iterative phases of product innovation.

Make it matter in live performances A favourite saying of jazz trumpet legend Miles Davis was: If you’re not making a mistake, it’s a mistake. Jazz musicians assume that you can take any bad situation and make it into a good situation. It’s what you do with the notes that counts. Reach beyond your comfort zone.

Listening to those around you is more important than what you play yourself If you’re the one talking, you’re not learning anything. Listen, absorb what you hear, and use the information to make a conscious choice about whatever you’re facing.

In jazz, performers vary their sounds and provoke others to respond, creating new music through collaboration. Similarly in startups, there is constant ideation and creation to disrupt, to simplify the complicated and generate new ideas. This collaboration happens best when everyone is working and listening together.

A jazz player listens in two special ways. Firstly, they ‘listen with generosity’, listening for the beauty, brilliance and ingenuity of their band mates, encouraging the expression of their virtuoso talents. Secondly, they ‘listen to the silence’ between the notes. In business, listening rather than talking is a key skill. In your startup, listen closely so you can move as one.

There’s a time to stand out as a soloist and a time to be a team player You rocked a project. However, it’s more likely the case that your team rocked a project, together. Katie was on top of the customer pitch, Sue got the product demo sorted, James nailed the process map. The best startup leaders are those that make others sound and look good.

In jazz, it is common for individual performers to alternate between lead and supporting roles in a single performance. Startups should employ a similar approach to develop the team and bring new thinking to the fore.

Expect surprises and adversity, since jazz (and startup life) is about how you respond If running a startup was always smooth sailing, and it followed the notes on the score, everyone would do it. The old adage applies, that ‘a smooth sea never made a skilled sailor’, so anticipate hurdles and maximise learning from them.

Jazz has its roots form being–in the-moment collaborative innovation, just like the act of starting and growing ventures. If you’re not actively seeking new challenges and ways to expand your horizons, living the ups and downs, you are falling behind.

Don’t seek growth alone There is no such thing as a mistake in jazz – come and listen to me play! Coltrane built a constant change of pace to create new sounds. Startups should also embrace errors and accept new possibilities as they adapt, solve problems and learn.

Jazz musicians feed off of each other to inspire. Startups should foster similar innovation by embracing chance encounters and conversations. A microcosm of spontaneous moments nurtures an aesthetic of openness and surprise.

Jazz, like a startup, is about pitting your wits in the heat of the moment. Just watch the different solos and see how the other members support the soloist and you will be surprised on the amount of dynamic emotion that is created. If you’re a startup founder, grow your business by growing your team.

Find your own sound: rely on minimal structure and maximum autonomy Jazz musicians prepare themselves to be spontaneous. Startups must do the same. To the uninitiated, jazz seems like chaos, whereas the reality is an underpinning structure to the apparent randomness is a long tradition of education and practice.

Coltrane played jazz as smooth and cool, and as a rage; his solos never seemed to begin or end. Coltrane wasn’t methodical, but wasn’t messy either. His saxophone playing was a conversation, a give and take, a connection and a dialogue between himself, his instrument and his audience. Coltrane knew this instinctively, he used innovation to find his own sound.

Coltrane teaches us that you have to find what’s right for you, leading to finding your own place of uniqueness. Trying to be what others want you to be will lead ultimately to failure. You have to find what you do best, and find what is best about you, for you.

What Coltrane and entrepreneurs share is the ability to address complexity and thrive while playing in the messy, fertile space of uncertainty, ambiguity and promise. He said, I start in the middle of a musical sentence, and move in both directions at once.

His spirit of adventure, desire for improvisation and innovation captures the essence of an entrepreneur: don’t play what’s there, play what’s not there. Improv makes you present in the moment. You listen, you’re attentive. You’re not acting, so much as reacting, which is what you’re doing in startup life all the time.

John Coltrane: startups and all that jazz

I’ve been a clumsy, enthusiastic saxophone player for several years, someway off Malcolm Gladwell’s 10,000 hours of deliberate practice to become anything close to consistently good, but I’m able to knock out a few recognisable tunes and get folks’ toes tapping.

As part of learning the instrument, you have to be able to improvise, playing with my teacher in a jazz jamming ‘free flow’ session to stretch your style, and speed of thought, playing chord progressions as spontaneous practice. Alas my concrete fingers constrain my dexterity, but playing jazz is fun and a chance to energise yourself.

My favourite saxophonist is the late American John Coltrane, also known as ‘Trane’. Coltrane pioneered the use of modes in jazz and was later at the forefront of free jazz. He played with some of the greatest jazz exponents, including trumpeter Miles Davis and pianist Thelonious Monk.

Despite a relatively brief career – his solo career wasn’t launched until aged 33 in 1960 and he was dead by 1967 – Coltrane is among the most important figures in jazz. With a wealth of posthumously released material, Coltrane was a protean player who changed his style radically over his career.

Whilst taking jobs outside music, Coltrane attended the Ornstein School of Music and began playing in local clubs. In 1946 he switched from alto to tenor sax having met the iconic Charlie Parker, and in 1951 joined a big band led by Dizzy Gillespie, a septet, and on March 1 1951 he took his first solo on record during a performance of We Love to Boogie with Gillespie.

In 1955 he was hired by Miles Davis and began to record profusely, but he failed to kick his heroin habit and Davis fired him in 1956, only to reunite in 1957. Coltrane also joined the Thelonious Monk Quartet and during this period he developed a technique of playing several notes at once.

Coltrane’s second album was cut for Blue Note Records. This was Blue Train. From here on, his recording were noted for the ‘sheets of sound’ playing style. He also developed a ‘modal’ playing style, improvisations based on scales rather than chords, heard best on the album Kind of Blue, released in 1959, which became one of the best-selling and most acclaimed recordings in the history of jazz.

To truly know Coltrane’s work is to hear every note in every context, my favourites being his chord substitution cycles known as ‘Coltrane changes’, heard on Giant Steps (1959), generally considered to have the most complex and difficult chord progression of any widely played jazz composition. His development of these altered chord progression cycles led to further experimentation with improvised melody and harmony that he continued throughout his career.

In April 1960 he formally launched his solo career, increasingly playing soprano sax as well as tenor. In the wake of commercial success, his style was frequently dubbed ‘avant-garde’ or ‘free’, noted in a 16-minue improvisation of Chasin’ the Trane in 1961. Thereafter, he continued to play a middle ground between traditional and free playing.

Coltrane’s rich productivity of releases in 1966 were the last recordings during his lifetime, as he died suddenly in July 1967 of liver cancer. He left behind a considerable body in unreleased work that has been posthumously issued. He won the 1981 Grammy for Best Jazz Performance for Bye Bye Blackbirds, a live recording made in 1962, and he was given the Grammy Lifetime Achievement Award in 1992, 25 years after his death.

Coltrane is one of jazz’s most influential musicians, stemming from an appetite for experimentation, taking chances and devoting himself to innovation in his craft. His name lives on, his 100 albums on iTunes each a compositional realisation, execution and recording from the mind, mouth and flurrying digits of the late, exponentially great Trane.

Coltrane was a jazz entrepreneur, he did what any startup leader does: he improvised. They invent novel responses and take calculated risks without a scripted plan or a safety net that guarantees specific outcomes. They don’t dwell on mistakes or stifle ideas. In short, they say ‘yes to the mess’ that is today’s hurried, harried, innovative and fertile world of startups. This is exactly what great jazz musicians do.

In his revelatory book, Yes to the Mess, jazz pianist and management student Frank Barrett shows how this improvisational ‘jazz mind-set’ and the skills that go along with it are essential for effective startup leadership. He describes how like skilled jazz players, startup leaders need to master the art of unlearning, perform and experiment simultaneously, and take turns soloing and supporting each other.

Yes to the Mess vividly shows how the principles of jazz thinking and performance can help startup leaders to develop these critical skills. Indeed, Coltrane believed that musical creativity was an act of discovery. He thought that the music already existed, and it was his role as an artist to explore, to look for a sound that lay outside traditional boundaries. He knew that spontaneous creativity was the business of jazz. With less than 1% of the notes on the written page, he made up the rest on the fly – no going back to correct mistakes or rethink a passage.

So let’s look at the lessons startup entrepreneurs can learn from jazz greats like Coltrane:

Playing it safe gets you nowhere If you don’t take risks you’ll never excel. Playing it safe all the time becomes the most dangerous move of all. Deviate from routines. Rote activity doesn’t lead to the path of innovation or disruptive technology.

Jazz follows a basic chord progression with a simple beginning, middle and end. In startups, we also start with minimal structures. Iterations begin as prototypes progress and then final aesthetics, allowing us to identify what works and what doesn’t throughout the iterative phases of product innovation.

There are no do-overs in live performances For every hour in a performance setting, you should spend five hours practicing. Athletes do this, musicians do this – muscle memory is no different to being in front of a new potential investor or client. So why aren’t you doing this?

A favourite saying of jazz trumpet legend Miles Davis was: If you’re not making a mistake, it’s a mistake. Endemic to jazz, errors push musicians to reach beyond their comfort zones. Jazz musicians assume that you can take any bad situation and make it into a good situation. It’s what you do with the notes that counts, but practice is key to developing your skills and style.

Listening to those around you is more important than what you play yourself If you’re the one talking all the time, you’re not learning anything. Listen, absorb what you hear, and use the information to make a conscious choice about whatever you’re facing.

In jazz performances, members vary their sounds and provoke others to respond, creating new music through collaboration. Similarly in startups, there is constant ideation and creation to disrupt, efforts to simplify the complicated and generate new ideas, but this collaboration happens best when everyone is working and listening together.

There’s a time to stand out as a soloist and a time to be a team player You rocked a project. However, it’s more likely the case that your team rocked a project, together. Katie was on top of the customer pitch, Susie got the product demo sorted, James nailed the process map. The best startup leaders are those that make others sound and look good.

In jazz, it is common for individual performers to alternate between lead and supporting roles in a single performance. Startups should employ a similar approach to develop the team and bring new thinking to the forefront.

Expect surprises and adversity, since jazz (and startup life) is about how you respond and adapt If running a startup was always smooth sailing, and it followed the notes on the score, everyone would do it. That being said, the old adage applies, that ‘a smooth sea never made a skilled sailor’, so anticipate hurdles and maximise your team’s effort to jump over them.

Jazz has its roots in real-time, collaborative innovation, just like the act of starting and growing ventures. If you’re not actively seeking new challenges and ways to expand your horizons, living the ups and downs, you are falling behind.

Jazz musicians often borrow from the past to create new music in the present. In startups, every past project acts as a library of inspiration and fuel for future work.

Don’t seek linear growth alone A jazz-driven approach requires the constant revision of assumptions and lessons learned from failure. There is no such thing as a mistake in jazz – come along and listen to me play! Coltrane built off of a constant change of pace to create new sounds. Startups should also embrace errors and accept new possibilities as they adapt, solve problems and improve inefficiencies.

Equally when developing their own technique and style, jazz musicians practice together, feeding off of each other to inspire creativity. Startups should foster similar innovation by designing their workspace in a way that encourages chance encounters and conversations between functional teams. A microcosm of a provocative learning nurtures an aesthetic of openness and surprise.

Rely on minimal structure and maximum autonomy A key lesson is that startup founders, like jazz musicians, need to, in Barrett’s words, interpret vague cues, face unstructured tasks, process incomplete knowledge and take action anyway. Musicians prepare themselves to be spontaneous. Startups can and must do the same.

To the uninitiated, jazz seems like chaos, whereas the reality is that it’s very ordered, underpinning the structure of apparent randomness is a long tradition of education and practice.

You can see a jam session as an effort to break down hierarchy. In a jam session, rank doesn’t matter. What matters is your ability, your willingness to take a risk, your spirit of both camaraderie and good-natured com-petition, and your wits in the heat of the moment. The jam session addresses a problem: How do you learn from other talented professionals that you don’t ordinarily get an opportunity to work with?

Listen closely to move as one As in business, communication is a crucial element of jazz. If you watch closely what’s happening between the musicians, you will see that without timely communication among the members they would never perform at their highest level. Just watch the different solos and see how the other members support the soloist and you will be surprised on the amount of dynamic emotion that is created.

Sometimes you’ll see jazz musicians performing in complete sync, changing tempos, ending the piece together, yet with no visible cues among them. Are they communicating by telepathy? No, they’re actually listening very closely to one another.

A jazz player listens in two special ways. Firstly, they ‘listen with generosity’, listening for the beauty, brilliance and ingenuity of their band mates, encouraging the expression of their virtuoso talents. Secondly, they listen to the silence between the notes. In business, listening rather than talking is a key skill. Whether you are listening upwards, listening downwards, or listening sideways in your startup, listen closely so you can move as one.

Find your own sound In today’s competitive environment it’s vital you differentiate yourself from the competition, to stand out from the undifferentiated greys of the pack and in living colour, show your uniqueness.

John Coltrane knew this instinctively, he pulled to the head of the pack by finding his own sound. Coltrane teaches us that you have to be authentically yourself, to find what’s right for you, leading from your own place of uniqueness. Trying to be what others want you to be will lead ultimately to failure. You have to find what you do best, and find what is best about you.

Coltrane played jazz as smooth and cool, as a rage, his solos never seemed to begin or end. Coltrane wasn’t methodical, but wasn’t messy either. His sax playing was a conversation, a give and take, a connection and a conversation between himself, his instrument and his audience. He said, I start in the middle of a sentence, and move in both directions at once – his spirit of adventure, improvisation and uniqueness captures the essence of an entrepreneur and their startup bravura.