Bing Crosby and The Intimacy of Crooning: Creative People Can Make Great Entrepreneurs


Bing Crosby was a revolutionary. 

Born in Takoma, Washington in 1903 and raised in Spokane in the same state, he embarked on a musical career in the 1920s when the convention amongst singers was to deploy a loud ‘belting’ sound. Performers like Al Jolson from the vaudeville tradition were ever mindful of the need to project their big, booming voices to the back seats of the theatre. 

Crosby was one of a new generation who embraced the recent technology of the condenser microphone. He regarded the microphone as his instrument. He leaned into it, caressed his notes and purred his lyrics. With the microphone he could bend melodies and twist phrases. He could be laid back and conversational, pleading and emotional. He could be intimate.

Though Crosby didn’t like the term, the new singing style was called ‘crooning.’ Some were critical of this fashionable approach. Cardinal O’Connell of Boston complained: 

‘Crooning is a degenerate form of singing…. No true American would practice this base art. I cannot turn the dial without getting these whiners and bleaters defiling the air and crying vapid words to impossible tunes.’

Nonetheless, crooning was a hugely popular phenomenon. Ten of the Top 50 records of 1931 featured Crosby’s mellifluous bass-baritone. Crooning was informal, easygoing, casual. It seemed quintessentially modern and American. The key to its appeal resided in its intimacy. The crooner came across as someone who was in the room with you, sharing a joke or confiding a secret; as someone you knew. Fellow singer Dinah Shore observed: 

‘Bing Crosby sings like all people think they sing in the shower.’ 

Perhaps there’s something we in the field of commercial creativity could learn from Crosby. We tend to concentrate on the functional benefits of digital technology: we think of it in terms of enhanced data, distribution and targeting; of superior user interfaces, connectivity and customer journeys. Of course, technology delivers all these things. But we should not forget its considerable emotive power: technology can demolish distance and time; it can create closeness; it can make things more personal and private. Technology enables human intimacy. This is a precious thing.

Crosby went on to become the world’s first multi-media star. His success extended from live performance, to radio and recordings. He had an Oscar-winning film career and he later evolved into TV. 

‘Listen a lot and talk less. You can’t learn anything when you’re talking.’

Throughout his life Crosby was a natural innovator. When the record market was hit by the Depression of the 1930s, he agreed to take a royalty rather than the customary flat fee. In the 1940s he embraced magnetic tape and was the first major performer to pre-record his radio shows. With pre-recording he could control performance conditions and times; he could ad lib and edit out mistakes. And by pre-recording four shows in a week, he could also spend more time on the golf course. 

As his fortune increased, Crosby bought TV stations and recording studios. He financed the development of the video-tape. He invested in fast-freezing technology and became Chairman and lead promoter of Minute Maid orange juice.

We can learn a great deal from Crosby. He demonstrated that creative people should view technology, not as an enemy, but as an ally - something that inspires new approaches and opportunities; something that enables them to take control of their work and how it is received. And critically he demonstrated that creative people should regard entrepreneurism, not as an alien craft, but as a natural extension of their talents. Creatives should be at the heart of a thriving business, not at the margins of it.

Bing Crosby passed away in 1977, having completed a round of golf on a course outside Madrid. His last words were:

‘That was a great game of golf, fellas.’


‘Oh, what eyes you have.
Oh, what lips you have.
Oh, what lovely features.
Talk about adorable creatures.
You have so many thrillables,
That I’m all out of syllables.
From the top of your head,
To the tip of your toes,
You’re marvellous.
Glorious, you are simply divine.
Top to tip, you’re tip top,
But to top it all, you’re mine.’

Bing Crosby, From the Top of Your Head (Mack Gordon, Harry Revel) from the film Two for Tonight (1935)

No. 249

Baitless Fishing: Beware the Seductions of the Quiet Life

‘We’re busy doin’ nothin’
Working the whole day through,
Tryin’ to find lots of things not to do.

We’re busy goin’ nowhere.
Isn’t it just a crime?
We’d like to be unhappy, but
We never do have the time.’

Bing Crosby, Busy Doing Nothing (Johnnie Burke/Jimmy van Heusen)


When I was a kid I used to go fishing at South Weald with my schoolmate Neil. I loved the peace and tranquility; sitting by the water’s edge, chatting about our packed lunches, polo neck sweaters and Prog Rock. But I didn’t like messing around with maggots and removing hooks from gurning roach. I determined secretly to fish without bait, thereby retaining the peace and tranquility but missing out on the muck. For a time this strategy went very well and it worked for the unknowing Neil too: he celebrated landing one fish after another whilst my tally remained resolutely on zero. But eventually Neil tired of the lack of competition and confronted me. When I revealed what I’d been up to, he refused to go fishing with me ever again.

I think many people in business are engaged in Baitless Fishing: keeping our heads down, avoiding conflict, choosing the safe option; never challenging the boss, rarely offering a point of view, always toeing the line. Doing things without getting things done.

Just as it’s a natural human emotion to seek credit, reward and recognition, it’s equally natural to avoid attention and opt for the quiet life.

We can fill our working day with status meetings, updates and catch-ups. We can write lists, file contact reports, adjust Gantt charts. We can attend courses, conferences and multi-disciplinary awaydays. We can meet random people for coffee in the name of networking. We can walk around the office a bit in the name of management. We can jump on a plane and visit some ‘key local markets.’ We can do all of these things without really progressing the Client’s or the Agency’s core agenda.

Of course these activities have some value. They are the stuff of business, the necessary everyday tasks that keep wheels turning and plates spinning. They sustain momentum. But in the digital era momentum may not be enough.

There are two senses of the word inertia. On the one hand it means doing nothing; on the other it means repeating an action or movement over and over again. Nowadays both amount to the same thing. Inertia can be a dominant force in all our lives and we must fight it.

The most common excuse for not tackling the bigger, tougher business decisions is the pressure of the imminent and the immediate. ‘We’ve got to get through this current crisis; see out this week, this day, this meeting.’ ‘We’ve not got the time, the resource or the energy to address the future right now.’

The greatest enemy of the long-term is the short-term. But the short-term and long-term are intimately related. As the Strategist Cathy Reid once observed:

‘The long term is just a series of short terms. You have to decide which short term your long term starts with.’

 Of course, ultimately Baitless Fishing is unsuccessful and unfulfilling. Within a business the metabolism slows, appetite wanes, morale dips; and then the competition outflanks you, the Clients leave you, the numbers condemn you. For the individual, work becomes a job, not a career; an occupation, not a vocation. And, as I learned to my cost, the Baitless Fisherman is always found out.

‘I have wasted time and now doth time waste me.’

 William Shakespeare, Richard II

So we all have to set aside excuses, re-order our priorities and resist the forces of inertia. We must take a deep breath and reach into the seething maggot box of business; bait that hook and cast our line into the deep blue ponds of the future.


This piece originally appeared on on 11 May 2016.

No. 82