Scaling Ship 30 for 30: Nicolas Cole and Dickie Bush's Success

Writing is one of the most fundamental and transferable skills in any business, and Ship 30 for 30 will transform you into a better writer in just 30 days.

Ship 30 for 30 believes anyone can be a data-driven writer.

No matter what you do for work or in your personal life or whether you have five minutes or five hours to spare, there's space for you to write better pieces and get them in front of your audience.

Co-founders Dickie Bush and Nicolas Cole created Ship 30 for 30 in late 2020. Since then, they've worked with an astounding (over) 4,000 members across monthly cohorts. Within their 30-day coursetime, members create and publish at least one piece of digital writing each per day alongside a group of other budding and seasoned writers.

By acknowledging frequent shared blockers amongst all writers like overthinking, over-editing, and falling out of practice, the Ship 30 for 30 team will break you of bad habits and help you gain new inspiration. When you can create rather than stagnate, you'll create thought-provoking articles and understand ways to make written content to reach new audiences to grow your publishing platform and build authority.

During the course materials their rapid rise to success, Dickie and Nicolas have gained a ton of insight around course design, marketing, and alumni nurture that other founders and operators of virtual learning businesses can and should draw inspiration and lessons from. Let's dive into their story and learnings.

11 insights from Dickie Bush and Nicolas Cole, Ship 30 for 30 co-founders, on creating and scaling a virtual learning business

Don't give up before trying to make something a habit

In an effort to create new potential career opportunities and have an outlet from his gig on Wall Street, co-founder Dickie Bush turned to writing.

For months, he published his work to an audience of (basically) zero; nobody was enjoying the fruits of his writing labor. Dickie turned his sights to Twitter and made a pact to himself that every day for 30 days, he'd share an article or his musings on the channel. If after 30 days Twitter didn't take off, he knew writing wouldn't be for him.

As any good origin story goes, it worked. Tweets went viral, newsletter subscribership grew 10x overnight, and Dickie quickly learned just how powerful it is to be consistent. But with consistency, you need accountability, which is when he opened up Ship 30 for 30's first unofficial cohort to a community Slack group. For $50, you could start the 30-day challenge. You got your money back if you completed it. From there, the challenge became a more formal course and the cohorts scaled from there.

Today, Ship 30 for 30 is a full cohort-based learning experience including live calls, a kindred community and a curriculum based around the fundamentals of publishing daily what it means to write digitally.

The lesson here? To be successful in business, there are actions that need to become habits: Things like learning consistently, documenting your ideas and findings, and taking specific care to curate your community should all become habitual rituals as your virtual learning business takes off.

Harness the power of accountability to recruit prospective members

“If you trace that problem all the way through, the problem that most people have isn a writing habit is't actually ‘I want to write better.' The problem is ‘I can't get myself to write for more than three days in a row.' Having clarity around what that problem is is what makes Ship 30 for 30 so compelling,” shares co-founder Cole.

Dickie was connected to Cole during his 30-day Twitter writing trial and they bonded over the same journey and the shared experience of needing accountability. They teamed up for the preceding cohorts of Ship 30 in an effort to bring folks together for a 30-day writing challenge, noting other aspiring writers' desire to have some camaraderie and a place to check in on progress.

“Where Dickie and I really connected was that we both experienced the same thing. We both came to the same conclusion and realized it's a whole lot easier if you do [writing] with other people,” says Cole. “So the first evolution of Ship 30 was accountability.”

Now established writers themselves (Cole quite literally wrote the book on The Art of Online Business Writing), Cole and Dickie acknowledged that they could do more to educate members and create opportunities to help them expand their writing capabilities.

“But over time, with each cohort, we've basically incorporated how you can master the fundamentals. You're going to write headlines that go viral, and you're going to learn how to write not just on Twitter, not just essays, but also LinkedIn. Also, blog posts. Also, these other formats, but the core of it is still accountability. That is what makes Ship 30 work.”

As co-founders Cole and Dickie learned quickly, creating a touchpoint of accountability and giving your members a place to convene for support is oftentimes more of a selling point than the actual subject you're teaching. Because they have created such a positive touchpoint of accountability, word of mouth generates the majority of Ship 30's business:

“Right now, about 35% of all new students come from someone in Ship 30 telling them to bring a friend along for a future cohort. That's an indicator that we started to track very closely, because I think a lot of courses have word of mouth either working for them or against them.”

Accountability is a core trait that has made virtual learning communities like ChairmanMe so successful. Read why that is and how they cultivate accountability through frequent touchpoints and cohort-based learning opportunities.

Help members create momentum

Sometimes, you'll find folks want to join your cohort-based course not because they need to learn anything additional, but because they're stagnant and need a good push. They need the tools, resources, and accountability to keep going even if they're in a rut. They need to build habits.

“You're gonna have some days where you wake up thrilled to write; the words just flow from your fingertips. It's like you're writing something that was meant to be written. And then there are some days that you're going to struggle and you don't want to write. You're going to procrastinate, you're going to put it off, you're going to miss a day,” Dickie shares.

“And then you have to learn how to get back on track when I fall off my daily writing habit. You're going to put something out there that you think everyone's gonna love, then no one really gives it any attention, right? [We teach] the highs and lows of emotion that most people have to deal with on their own. Those are what causes them to quit. Instead, when you do that all with a community, you have them with you the whole time.”

Create distinctions to hone in on your core audience

In determining who their main audience was and what types of people they wanted to recruit for Ship 30 cohorts, Dickie and Cole started by operating off assumptions. Those assumptions only helped lead them to important conclusions and rather, a very key distinction.

“Our biggest realization was that Ship 30 is in the business of inventing net new writers. If you've been doing other writing courses for ten years and you want to know how to incrementally improve as a writer, Ship 30 is probably not the best thing for you,” shares Cole. “Ship 30 is specifically designed for the person who goes ‘I've been thinking about writing online for a long time, but I've never taken the first step.' That distinction is everything.”

In their mastermind group, Cole and Dickie acknowledge that a lot of folks who want to launch online writing courses will find themselves in the middle of this distinction. Cole shares, “Your job is to get more and more specific to the point where it's like, is it for people who start or people who accelerate? You know, and that difference in itself is two different horses.”

While creating your target audience involves a ton of data and customer research, starting with that key distinction can help steer you in the right direction.

Enable members to learn their own way

In just over a year, Dickie and Cole were able to scale to their biggest live cohort yet of 1,300 learners. Through fostering a community and creating an actionable curriculum, they've been able to design a course that helps thousands of learners at a time.

‍But how?

‍By enabling people to learn in their own way rather than dictating how their experience will go.

Dickie shares, “Our biggest framework for this is enabling instead of dictating. I think a lot of courses go wrong when they try to make everyone do the same thing. ‘We're going to tell you where to go and what to do.' The truth is, when you have big cohorts like this, everyone's in it for a different reason. Some people sign up and they're not going to watch a single live session. They're not going to come to any of the events. They're going to just try and write every day for 30 days.”

“Then you have others that are going to soak in every second, they're going to be on every second of the various live sessions and calls, they're going to be answering questions, asking questions, all that. Our goal is always to make it available to every student to get as much out of it as they possibly want. We don't say, ‘Hey, you need to be on this call at this time in this way.'

Dickie also goes on to credit software enablement to achieve more personalized outreach and understand how learners are progressing.

“We have a very intricate learning design system of gamification that allows students to track their own progress throughout the course. It allows us to see from the very top who is stuck, who's crushing it, who's continuing. I know at any given time the last time someone attended a call, the last time they wrote an essay, or the last time they completed one of our assignments. We have daily or weekly interventions via email based on each student's progress.”

For budding founders and operators of live learning communities or virtual learning businesses, understand what it means for someone to successfully navigate your course and enable them to succeed by giving them the freedom to learn their own way.

A combination of synchronous and asynchronous work is what helped Dr. Mike Barger scale CorpU to 160,000+ learners. Read why this model is so successful in building audiences and creating transformative learning experiences.

Use software to scale, not problem solve

“The first few cohorts of Ship 30, Dickie and I were maniacal about talking to individual people. We would finish a cohort and send surveys, do individual calls with people, we'd talk to people in DMS — we were constantly trying to understand in a very small way ‘What is engaging to you versus what's engaging to the next person? What questions do you have that are different from a different archetype?'” shares Cole. “You have to go through that process with a small group of people.”

Both co-founders credit this early feedback as a major catalyst in designing a learning system that today supports thousands of members. Again, software enablement is critical to accepting and utilizing this feedback.

“Software is what allows you to leverage those learnings to more people. Whereas, I think a lot of times, course creators have it backwards. They go, ‘Okay, day one, I need to pick all the software that's going to allow me to manage a cohort of 3000 people. Software is not the problem. Your problem is you don't actually know the 10 different problems that people are experiencing. Once you go do that homework and you pinpoint the problems you're solving, then you add on software to scale the solution. But software in itself is not the solution.”

Software like ours at Disco has enabled virtual learning businesses like BatteryMBA carve out a niche and upskill thousands of professionals in their vertical. Learn how.

Use free tools to expand your category, not just to convert new members

We mentioned last week that co-founder Cole wrote the book on The Art and Business of Online Writing. Having that as an asset allowed him to seed legitimacy from the very beginning.

He also quickly realized it could be a great lead magnet if he made the book available online for free to provide information and inspiration from the jump. This is the same strategy that other courses take when they create a free trial or another no-cost offering in addition to their main business. Where operators and founders of virtual learning businesses get caught up, though, is not wanting to give the enchilada away for free. On the contrary, sharing your expertise and giving people that information is more important for expanding the category you exist in so more people might seek out that information and find your business.

Cole shares, “I can't tell you how many people download [the book] and they don't take Ship 30. That's great. Mission accomplished. You're another person that's going to start writing on the Internet, which is going to make the whole published writing category bigger. Everyone's default is ‘I have my information and I don't share it. You have to buy my course in order to have it.' That's a mistake. Because the reality is, most people are not buying your course 100% for the information. What they're buying is the personal relationship with you. They're buying the accountability. They're not just buying the information.”

By creating free courses, free downloadables or e-books, a trial of your course or some other sticky lead magnet, you're expanding the likelihood that someone will find your course serendipitously and become an integral member of your community and alumni network.

Because Dribbble led with a free taste of their successful Product Design Course, they were able to scale membership and generated impressive WOM. Read how.

You can always increase your price, but it's not a good look to decrease

Pricing will always be one of the most uncomfortable topics for founders and operators of bootcamps and academies to discuss and determine. But one helpful framework the founders of Ship 30 share is that you should be extremely cautious when raising your prices, but even more so if you choose to bring prices back down (as it may cheapen your experience.

Cole shares, “You come out guns swinging and you launch your course at $3,000 bucks. And then six months later, it's $300 bucks. You don't want to do that. If you just take the time — maybe do your first one for free — see if what you're doing is even compelling, right? There's no point worrying, should I charge $500 or $700, when you don't even know if what you're doing is what people need. Start at the very bottom and then inch your way up.”

With this framework, Ship 30 has been able to steadily increase the price of their course by $50 or so at a time, currently costing $750 a pop. But with every price increase, there's a corresponding discussion of how to increase the value exponentially.

“Every single time we increase the price by $100, we say how can we add $1,000 more value to this,” says Dickie. “Price increase is a lagging indicator of things we've added along the way: more curriculum, more content, better accountability, better systems, better student experience, better customer support, and better student success.”

Good courses create new problems

Once members have completed your micro-school, bootcamp, or academy, they should leave with an entire new set of (good) problems to have around career improvement, personal development, and implementing all of their learnings. If you've done your job, they're ready to tackle these new problems.

Dickie shares “I think any good course creates new problems for their students by the end. Those are good problems to have — problems that they would have begged to have had at the beginning of the course. You write every day for 30 days, what are your next biggest problems? You've got to figure out what it is you want to write about long-term, so finding your niche. You might want to go down the route of becoming a ghostwriter or freelance writer. You might want to launch a digital product based on what you've created. There are a bunch of different paths you can take.”

Good writing courses always create good problems to solve because you'll have so many opportunities that open up for you upon completion. Where founders and operators can contribute to that is by fostering an alumni program for continued learning and networking.

Empower alumni to participate and continue learning

Over 4,000 alumni later, Cole and Dickie have fostered an alumni community “that allows for that continued learning with our expertise (kind of) sprinkled in while using the same challenge-based, time-based, and accountability-based models that work so well for the original Ship 30 course,” says Dickie.

At Ship 30, this effort is known as The Captain's Table.

Dickie shares, “It's basically a membership community where we share weekly calls, weekly accountability, and other one-off challenges that are like Ship 30. You're gonna create your own blog or niche, you might launch a newsletter, you might launch a digital product, you might figure out how to light up different platforms. We put all those different mini challenges together, and kind of a ‘choose your own adventure'. It's very fun, because you end up getting so many different people taking all these certain paths. We're seeing those start to compound now and that's only about a year old. Every single day, someone has some kind of new, big successful way in which they went viral on a platform or where they landed a new job or new clients. And so seeing that grow has been the most fun part of 2022 so far.”

With The Captain's Table, the Ship 30 team is able to keep alumni close to the mission and continue cultivating transformative experiences for them. This model creates a low-effort way for alumni to keep the momentum, the accountability aspect, and foster important networking connections that founders of other virtual learning experiences can replicate.

The Future of Virtual Learning Means Everyone Can Be a Teacher

“What the internet allows for is for people to make decisions. The only information I need is the thing that's gonna get me from where I am right now to the next thing I want to do right now. If you remove the concept and idea of needing to learn from someone who's a professor and instead, all you need to spend time to learn is from the person who's one step ahead of you, then the entire learning process changes,” shares Cole.

‍“You don't need to learn from a gold medalist or you don't need to learn from the guru at the top of their industry. You can literally learn from anyone.”

Because the digital age and the virtual learning industry is exploding, this will also change the way we determine our career path and personal development. Learning, rather, will become cyclical over linear.

On Deck's former Head of Education Eliot Gattegno believes everyone is a teacher as well as a reader digital writer and student, and it's important to acknowledge that so transformative learning can happen. Learn about this philosophy here.

Cole shares, “You're going to learn the next piece of information just in time to unlock that next piece. Then, when you're there, you're going to decide the next thing that you want to learn. And then you're going to find the next person who knows that just in time, and so on, and so on and so on. And you already see that happening. You have 11 year olds launching Shopify stores. What are they doing? They're like, ‘I want to do this. I need this information just in time.' And then they go do it and they unlock the outcome they need.”

“The amount of wasted learning — it was all “just in case” learning. The classes that I really enjoyed were all about building things,” says Dickie. “It was computer science or classes where you left with a tangible result. It's results driven: I want to learn a skill, accumulate that skill, then move on to the next thing. That's where the future of education is going: The ability to do and create, instead of just feeling like you're learning for the sake of learning, which really, I think turns into procrastination. It isn't really moving you towards something. I think the most actionable courses in educational businesses are the ones that are going to deliver tangible outcomes versus just information.”

It's because of incredible minds like Cole and Dickie's that we have courses like Ship 30 for 30 to use as a point of reference and inspiration for any other writers and budding founders interested in the space. Check out their Free Digital Writing Course to get started on your own writing journey today.