Choose Your Own Writing Adventure

Benjamin Perrin
12 min readJan 21, 2021

My interview with Max Nussenbaum, Program Director @ On Deck

The interview below was first published in Plumes With Attitude (🇫🇷), my personal newsletter on the benefits of writing.

Max Nussenbaum is the Program Director of the Writer Fellowship at the hottest accelerator/school/tech mafia of the Internet : On Deck. I had a great time talking about the future of writing with such a charismatic polymath.

Here is our interview. Enjoy the read!

Max Nussenbaum created the On Deck Writer Fellowship from scratch

Nice to meet you Max, and a huge thank you for accepting this interview! Let’s start with your background: you’ve been alternatively a startup operator, a founder and a freelancer in product, design and software engineering. You’ve also been the coauthor of a business book, Oversubscribed. So I was wondering: why writing? And how did it come to your life among so many interests?

I’ve been interested in writing for as long as I can remember, even before I have conscious memories. I still have stories I wrote when I was in second grade. Then I went to school for writing and I was a creative writing major. I also wrote a musical in college, and later a book of short stories. So I really thought I was going to be a writer.

But when I graduated, I realized that becoming a full-time writer didn’t necessarily look the way I’d have imagined. The fact is, I didn’t want to work alone and I wanted my job to be as collaborative as possible. So I ended up making a really sort of unexpected jump into startups. I worked in the tech industry and I started a real estate company that had a classic Silicon Valley rise and fall. But writing was still a big part of my life, mainly through side projects.

I also found that a lot of the skills I was drawing on as a founder were, in some way or another, related to writing. A lot of what I was doing was telling stories, whether it was telling our customers the story of our product, selling our vision to investors or crafting the story of our company. Eventually, I was offered the opportunity to join On Deck and build out the Writer Fellowship last year.

Such a dream job for you! How did this opportunity happen?

This actually ties to my practice of writing. I’ve been friends with Erik Torenberg, the founder of On Deck, for almost a decade. We both started our careers in Detroit and we bonded over writing. We did a little bit of a writing group together and we both attended a book club that was infamous for only lasting one meeting (laughs). We stayed friends over the years and kept in touch through writing online. When he was thinking about launching the Writer Fellowship, he asked if I wanted to be involved and I eventually said yes.

This perfectly illustrates one of the reasons why I think that ambitious people should write online. Thanks to my writing, Erik was still able to sort of follow my journey from afar. And when he reached out to me, it wasn’t like we had to spend hours catching up on all the stuff that had happened.

I agree with you: writing creates a special bond with your readers, which can definitely bring serendipity into your life. And I have the feeling that this is exactly what On Deck is about. So let’s talk about it further! I tend to consider On Deck as an elite program since the endgame is to train the next generation of world-class talents in areas like entrepreneurship, angel investing, content creation, along with healthcare and climate. However, you seem committed to the idea of making your programs accessible to all, as initiatives like your Access Fund show it. But beyond that, how do you balance selectivity and diversity?

We have two missions that could seem contradictory at first. One is broadening access and believing that talent can come from anywhere. And as you mentioned, the second is to build a community of world-class talent.

So the first layer of what we’re doing to expand access is to create a global remote-first community — what some people call the “Silicon Valley in the cloud”. Our goal is to move away from the days when you needed to be living in a specific place to be part of a certain community.

The second angle is about the journey at On Deck. Every program may be competitive, some are definitely harder to get into than others. For instance, the Founder Fellowship is one of the most difficult to get into. But there’s more than one path to join On Deck. Suppose you might want to start a company someday but don’t necessarily have an idea yet. Well, the Writer or Podcaster Fellowships are more accessible programs that will help you start honing and developing your ideas in the public sphere. And since you’ll be an On Deck Fellow for the rest of your life, it’ll likely be easier to join the Founder Fellowship when you’re ready. If your company takes off, you’ll then have the opportunity to send your employees into other programs such as the First 50 or the Chief of Staff Fellowships.

When selecting our future fellows among applicants, we’re asking ourselves two things. First, can we help this person succeed according to their own goals? Second, would this person be a great community member according to our guiding values? Beyond the programs, On Deck is about giving back, whether it’s with time, knowledge or support. This is why community is a core part of what we’re building.

I love this “choose your own adventure” approach between the different programs! Can you tell me more about how the different Fellowships communicate with each other?

We’re very intentional about making sure that every fellowship has a connection to the others so that they overall make the whole network stronger. Our vision has always been about enabling entrepreneurship. And we view entrepreneurship as something that’s defined much more broadly than this very narrow slice of Silicon Valley that too many people often focus on.

We tend to forget that writers and podcasters do build products, connect with an audience and create communities. They’re entrepreneurs too! Having a successful writing practice actually involves a lot of skills other than just putting words together. Beyond writing, you need to understand the basics of growth, branding and distribution for instance. And I think it’s much more stimulating to learn all these things within a community of peers than on your own. This is a big part of the thesis behind the Writer Fellowship.

Also, we are building one global community, not just siloed fellowships. And so we do a number of things to enable the fellows from different programs to interact. In February, we’ll have our first ever Global Build Weekend. The goal is to make people from different fellowships collaborate on teams. For instance, I’m looking forward to seeing the next cohort of writers learn the fundamentals of visual branding from the design fellows. In return, they will have the opportunity to teach them some storytelling and copywriting techniques.

I assume that a program such as the Writer Fellowship must be very tied to your own personality. How did you bring it to the curriculum?

That’s a great question! The Writer Fellowship was basically the first program launched after the Founder Fellowship. So I’ve helped a lot of the other program directors who have been launching new fellowships after me.

One of the things I’d really emphasize is that your program just inevitably takes on your own personality. When your product is an interactive experience within a community, there’s such a direct emotional connection between you and the “customers”. As program directors, we are lucky to have a lot of freedom to shape our curriculum as we wish. And my personal belief is that it’s all about the small things, from the music I choose when introducing a speaker to the dumb jokes I make in my presentations.

Our approach is very bottom-up and not “one size fits all”. It’s not a ten-step writing course where everyone has to do the exact same things in the exact same order. You don’t have to write a specific essay during the program or anything like that. We aim at independent and entrepreneurial people who already have specific goals and ambitions. And we want to be in a position where we have a broad curriculum that can support all of that.

Plus, having a “one size fits all” program would result in growing an army of clones writing about the same things with the same style. Can you tell me more about how you ensure to adapt to each person’s personality and authenticity?

The truth is, a big part of the program is about psychology. Like most creators, our fellows face common issues such as procrastination, lack of motivation, imposter syndrome or being scared to show their work publicly. Some of them don’t really need to be taught how to write as they are already great at this, even though there’s always room for improvement. Their most urgent need is support, so that they can get over their fears and have the courage to write about that topic that scares them.

I like to draw the comparison with the Founder Fellowship, as it’s very uncommon for an entrepreneur to start a company and then the startup fails because they just procrastinate and don’t get any work done. But that’s comparatively a very common failure mode among creators, even for experienced writers. A huge part of what we’re doing at On Deck is to create a comfortable environment for people to do what they’re good at.

We also want the program to be a really exploratory space. The fact that we’re not pushing everyone towards one defined outcome is actually a great opportunity to explore. I love nothing more than seeing someone who comes into the program to develop their blog, let’s say about the great economic competition between the US and China, and eventually decides to start an essay about their experience raising a family after seeing some other fellows writing very personal stuff. It doesn’t mean they’re going to stop writing about economics, but it’s a way to be able to stretch their wings and kind of get their creative juices going.

At the moment, the curriculum is mainly designed for people who are building an audience. But I guess that you could extend it to a lot of areas such as publishing, screenwriting, journalism, or even music. How would you personally want to see the Writer Fellowship evolve?

It’s definitely something that we think about. The good news is that we’ve attracted people working on several of these areas among our fellows. It’s very likely that within a year or two we’ll have dedicated programs for some of these topics.

The only thing is that we want to create programs that can legitimately help a lot of people succeed. I’ll take an example from my background as an aspiring fiction writer to illustrate what we wouldn’t do. So I’ve taken a lot of writing workshops in my life. Last summer, I was attending one in New York. Everyone in this workshop was trying to become a novelist. But when I looked around, I couldn’t help but think that no one here was ever going to be a published author. I’m not making any judgments but I’ve had the feeling that what these workshops are really selling is the opportunity to believe in the dream for a few hours a week.

So, would we ever start an On Deck fellowship to help people try to get a publishing deal? Well, almost certainly not since publishing is kind of a dying industry. Actually, one of the best ways to get published these days is to grow an audience and then leverage that into a book deal. But having a program focused on succeeding in traditional publishing would be like selling a pipe dream that the vast majority of people couldn’t achieve. It would be unethical taking people’s money knowing that the vast majority of them are never going to get there.

One interesting fact about our fellows is that they haven’t joined On Deck because they think that we’ll help them build a paid publication that will provide them 100% of their income. Rather, they see the fellowship as an opportunity to explore, to supercharge their career by writing about the topics they’re interested in, to connect with a broader network to boost their personal brand, and sometimes to make some money on the side. But those are all very achievable goals we can help them with.

That’s a very honest approach. I was simply curious about this possible evolution when I’ve noticed that you have someone in the first cohort who writes poetry.

You’re referencing Alysia Harris, a fellow who’s an award-winning poet and an incredible artist. She helped us learn a fantastic lesson during the first cohort. The vast majority of people in the program are primarily writing nonfiction. Yet we had several creative workshops, one or two about poetry, and what we actually realized was that even if you’re primarily writing nonfiction, you can get a ton of value out of doing a poetry workshop. You’re probably not going to just start being a poet. But they can be a great way to think more creatively and kind of get out of your rut. And the responses we got to these creative workshops have been very enthusiastic!

You’re preaching to the converted (laughs). I’m personally convinced that diversifying what you read and write on is key to find and sharpen your own style. Your ideas made me think of another interview I had with Li Jin last October. Her thesis on the passion economy is essential to figure out what’s to come for creators. So I was wondering: how do you envision the future of writing?

I think we’re at a really interesting inflection point for writing. While many of the traditional industries and mediums are suffering, people read and write today more than ever before. This is really exciting, with both a lot of opportunity and peril.

First, I think that people are too often too quick to view writing or other forms of creation with a binary viewpoint: either they’re trying to make it a full-time job or it’ll just be a hobby. But there’s a lot of space in between. For instance, I know someone who works in grocery logistics and writes a blog about the industry, which helped him get better career opportunities that he couldn’t have had otherwise.

Also, I’m a huge believer in Li’s approach of the passion economy. But like most things on the Internet, I think it’s going to end up forming a power law distribution. Substack is a great opportunity for independent writers, yet most people are never going to be able to support themselves entirely through a paid publication. I believe that many writers will follow the trajectory a lot of musicians have taken. The latter have started to think of themselves as products and monetized features like live touring, merchandising, private events, crowdfunding, etc. What I’d advise writers is to take a holistic view and figure out how they can bundle or unbundle what they have to offer. So the question is not about whether going full-time but about having multiple sources of income.

In some ways, that can be a depressing vision when you think that there was a much larger group of people making a living as full-time writers in 1960 than there is now. But let’s not forget that these people were pretty much all white men who came from elite universities.

And this is a very important point. But the new platforms have yet to prove that they can reverse this situation. To end up on a more personal touch: what are your writing projects right now?

I write a weekly email newsletter called My Super Secret Diary. I present it as a publication about “startups, literature, philosophy, American history, sex & drugs, and how to be alive,” but it’s really just about whatever I feel like writing about. It keeps me practicing and sharing my thoughts with what I like to call my “minimum viable audience”. I’m positive that it won’t be my only writing project for long, but for now running the On Deck Writer Fellowship is a pretty busy dream job (laughs).

5 resources on writing curated by Max:

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