Creating

Recently, someone told me that he wanted to work in a different field. But doing what he wanted would require him to “start over” and work back up to a place of expertise.

I could feel and hear the resistance and fear.

Why wasn’t he pursuing his dream?

Because he would have to start as a beginner. Again.

I’ve felt that, too. It was when I first started graduate film school. I was in my 30s and I had just stopped being a VP at eBay to pursue this totally different track. Most of my classmates were in their 20s. We were all beginners. But I felt like I was even more of a beginner than they were. I hadn’t been steeped in creating art for years.

I was drinking from a firehose. Every day was filled with wonder, learning, curiosity. And often, frustration.

A lot of the frustration came from the beginner’s gap between taste and capability (Ira Glass). You have good taste. But your execution sucks. Your capability doesn’t rise to the standards of your own taste. I faced that constantly, starting with the first shooting exercise. I felt embarrassed when I screened it.

For my next effort, I asked one of my classmates to be my cinematographer. I explained how I wanted it to look and feel. And he just… did it! His simple choices created the visual effect I wanted. It was a big a-ha moment for me. I understood the visual language in a new way.

Fifteen years later, I still remember when I realized there was a way to get across the gap between my good taste and my bad execution. I had to learn the language of the camera. I had to be willing to admit I didn’t know—to myself (painful) and to others (also painful). I had to open myself to truly learning (freeing), and then absorb everything I could (exciting).

To get there, I had to detach from my previous know-how, credentials, and expertise. I had to acknowledge that I didn’t know, that I wasn’t good yet, and that I had to work hard to learn the skills to deliver the film I saw in my head.

My sense is that the same thing is true for startup CEOs. You need a fresh perspective on the industry to be able to see how things can be done better. And you also need to have the humility of a beginner in building the business to find the things that will close the gap between your taste and your execution. It requires you to be humble and detach yourself from all of the things you’ve accomplished so far.

This is especially true when you are doing things no one has ever done — with no experts to consult and no roadmap to follow.

For example, Andre Haddad joined Turo (then known as RelayRides) as their CEO in 2012. He came to Turo with deep marketplace expertise — he was a founder of iBazaar which was acquired by eBay, ran design and then product at eBay, and was CEO of Shopping.com. But Turo was different in some key ways.

Turo had a completely new concept: monetizing your car by allowing others to use it while you were not using it. This meant that Turo was unlike other marketplaces where finding supply isn’t a huge issue. At Turo, it took fresh thinking to find a supply of cars and teach the hosts new behaviors.

Turo also needed insurance. No insurer had ever insured a marketplace for car sharing before. That required data. But in order to get the data, Turo needed insurance. Chicken and egg.

Andre’s previous marketplace experience wasn’t that useful to Turo’s specific problems. He had to get creative. He ended up radically over-paying for insurance in the short term—paying more in insurance premiums than Turo’s whole marketplace gross booking value (GBV). But he knew that he would only have to do this until they collected enough data to allow the actuaries to price the risk correctly.

Both of these were new problems that Andre encountered at the frontier. There was no playbook. There was no previous mastery to lean on. He had to accept the reality of being a beginner.

Andre tries to learn a new skill every decade. He uses this as a forcing function to put himself into a beginner’s mindset and grapple with what that entails. I love this concept. Here’s what beginner’s mind means to me:

• Unafraid of failure.
• Willing to appear (and be considered) incompetent.
• Eager to learn from others, and seek advice and help.
• Comfortable measuring your performance against own personal best, not based on an external metric.
• Excited when you discover you don’t know something (because now, you will learn).
• Low/no ego to maximize learning and growth.

Painful at the start, but useful.

My friend Sanjay Subrahmanyan is one of the top classical vocalists of India. Before Covid, he regularly performed at South India’s equivalent of Lincoln Center, for crowds of almost 2,000. After countless delayed and cancelled concerts, Sanjay eventually decided to go rogue. In January 2021, he launched a YouTube channel membership—a direct-to-consumer plan.

I thought this was a fascinating move, especially for someone whose audience consists predominantly of Baby Boomers, in the relatively conservative industry of Carnatic music

Sanjay described the change to me like this:

“In the past, the Music Academy and 10-15 other organizations would come together to produce one huge music festival. It’s a 30-day extravaganza with 5 concerts per venue per day. This was like being one flower in a bouquet. People are used to paying for the bouquet. Now, I’m asking them to pay for just one flower.”

Sanjay has three tiers of subscribers, using YouTube memberships. The basic tier is free, and everyone receives access to hundreds of archived recordings that Sanjay and his wife Aarthi have been collecting since the early 2000s. There are thousands of hours of these, and he releases more regularly. The second tier ($1 per month) gets a preview of the new uploads before they’re released to everyone else. The top tier ($10 per month) gets a brand-new concert every month, released to them exclusively. Sanjay gets together his accompanists, heads to a recording studio with a video and audio team, and performs and records a 90 minute concert each month.

Before the pandemic, the online world and business was a hobby for him. From discovering usenets in 1995 on a trip to the US to releasing songs on mp3s in the late nineties, he’s been personally fascinated with using and discovering new technology and exploring what was out there for his profession. But he considers it just dabbling. He never looked at online as a full-time business proposition because he was busy performing 50 to 60 concerts a year, all through inbound invitations. He was an early user of Gumroad and had also been releasing albums on Spotify and making a lot of his performances free on YouTube.

“But over the last three or four years,” Sanjay told me, “I realized the trend was more toward video: people want to see you, especially during the pandemic. I picked YouTube partly for that reason, and partly because it was very simple for subscribers. Most of my fans are in their 60s, so they need something simpler than Patreon or Gumroad. That’s why I use YouTube, even though their cut is 30%.”

A few takeaways from this:

First, ease is important; fans will be more open to paying if it’s really easy for them to sign up and access their stuff, so a platform where they already spend time has an added benefit.

Second, existing networks compound; YouTube is a compounding engine for Sanjay’s subscriber base. He has ~30,000 basic subscribers on YouTube. Converting a few of these people to paying subscribers and providing the rest with fresh content will reap dividends over time.

Third, it’s so important to keep a record of everything, so you have plenty of content to share and choose from. For a performer, it’s obvious how to do so – record everything. But for a visual artist, don’t discard “work in process” or little day-to-day projects. For a writer, even snippets that show how you work can be valuable. It’s not a big, fully wrapped deliverable, but it’s work you still created.

Sanjay realized that he had to share his performances with his audiences to stay relevant. He also realized he deeply missed performing. Performers have to perform!

To go from singing 60 concerts a year—which included planning and preparing, coordinating with accompanists, experiencing the joy of the performance and the gratitude of having an audience appreciate it—down to zero concerts in three months is very hard for someone who performs at the highest levels. And to lose a year of performance revenue in his prime was not easy. But it was a forcing function that made him take the leap into developing a direct relationship with his audience.

Sanjay has had to evolve from a performer focused on his craft to someone who has to focus on the business side of the equation. To use his creativity and apply it to areas like logistics and business operations, to marketing and branding.

This has unlocked new forms of creativity for him. While he’s primarily a performer of existing compositions, he has on occasion arranged new compositions. But these were all still vocal arrangements that were delivered during live concerts. In the past couple of months, he’s explored how to use video more creatively. He recently created a new arrangement of a beautiful poem called “Tamizhan endroru inamundu,” which means “Tamilians are a tribe.” His collaborators filmed it and developed a visual treatment for the poem.

For creators, will the hybrid model will become the default? Will more artists go rogue like Sanjay? Who are the kinds of creators who will be able to do this? Sanjay is typically a performer of music that other people have composed, so it’s been a relatively low-lift for him to produce new content. What about filmmakers, who have to bring a much bigger team together with (almost always) a bigger expenditure/budget? What about writers or composers, where each piece may take months and many drafts before it’s ready to share?

The “creator” economy is a very broad term that covers creators who are so different from each other in terms of frequency of creation, complexity of creation, ability to share work in progress, and so many other dimensions. It’s in the nuance of the differences that opportunities exist for both creators and for the tech solutions that serve them. Where will we go next?

In 2009, my writing professor, Ira Sachs, suggested we all read Twyla Tharp’s The Creative Habit as part of our class. His reasoning was that the purpose of writing class is to eventually create something. And the sooner we realized that was our focus, the better. Ira used the class as a forcing function to make a short film, Last Address, which screened at Sundance and Berlin.

I chanced upon the book recently and it made me go into the rabbit hole on Twyla. What an amazing and talented person. This video interview of her captures her essence, which is all about carpe diem, or “shut up and do what you love.”

She’s still creating at a world-class level.

So should we all. So, let’s do it.

I’m proposing that to end this year with panache, we read The Creative Habit, talk about it, and form our own creative habits.

I’m committed to doing this with my friend and poet, Ellen. Let me know if you can join us. Would love to have you.

Here’s how you can join:

1. Buy the book. You can buy it in Kindle or paperback. The paperback is beautifully designed.
2. Sign up: DM me on Twitter to get the calendar invites!
3. Read 4 of the (super quick) chapters by November 19th and join our Zoom call that day at 9am PST. We’ll share our takeaways and prompt a discussion in the group.
4. Read 4 chapters by December 3rd and join our Zoom call that day at 9am PST.
5. Read the final 4 chapters by December 17th and join our Zoom call that day at 9am PST.

DM me on Twitter to get the calendar invites!