Nathan Barry: The Founder Creator Building a Movement of Creators

Nathan Barry

When it comes to Nathan Barry, the lines between founder, creator, and colleague blur, as he is not a conventional founder.

With everything he does with ConvertKit and with its projects, he shapes an entire movement for creators seeking to make a living.

Who is Nathan Barry?

Nathan started out as a freelancer, then designed iPhone apps, then started a blog and built up an audience which later led him to write books on design.

After, in 2013 he created ConvertKit – an email marketing company for creators.

His mission with ConvertKit and everything he does is to help creators earn a living mostly because saw the impact that money had on relationships and stress from a young age.

Besides ConverKit where, he has other side projects such as newsletters, podcasts and a newsletter agency which are all around helping others grow.

But, I think it’s better to talk in detail about everything he does and why he is an incredible B2B creator, so let’s get started.

Nathan Barry’s Successful B2B Journey

  • Built a movement for creators
  • Nathan knows how to build and maintain an audience
  • He’s not your typical founder
  • Creates small projects for a bigger cause

1. Built a movement for creators

This movement for creators can be traced back to several key moments in Nathan’s journey.

1.a. Starting ConvertKit

He, as a writer and blogger, saw that he needed a way to reach his audience better to sell his books and courses.

So ConvertKit started its mission on the idea of helping creators make a living.

For creators, by creators” – the motto ConvertKit recently used in their videos.

He started ConvertKit in public on his blog as a project hoping to go from zero to $5,000/month in 6 months.

Sharing the whole story of ConvertKit was a way to show creators what are the struggles of creating a product, what skills you need, and how you can eventually make it profitable.

1.b. Bootstrapping ConvertKit

Nathan talked in different blog and podcast interviews about how he bootstrapped ConvertKit.

Even though he wanted to generate $5K in MRR, by the end of 2013 he was not there and faced sales decline.

Hiten Shah, the former co-founder of KISSmetrics, told him he should either shut the whole product down or focus on it to make it successful.

Nathan used to focus on the app online half of his time, using the rest to create ebooks and courses.

So now, he needed to make a decision.

He decided to give his 100% and put his $50,000 savings into ConvertKit.

This is what made this company grow.

Plus the sales and excellent customer service.

Nathan went into one on one sales calls and talked to people about their frustrations telling them about his product and realized people didn’t want to switch to another email provider because it was a lot of work.

What did he do? The thing I always say as well.

Doing the things no one is willing to do.

He spent his time helping his clients switch from other providers to ConvertKit.

A long and tedious work, but which eventually paid off as ConvertKit saw increase in sales and obviously in its MRR.

From hoping to obtain $5K monthly recurring revenue, with consistent work he managed to grow ConvertKit’s monthly recurring revenue at $3 million in 2023, hoping to end the year at $4 million.

Nathan’s choice to bootstrap ConvertKit demonstrates a hands-on approach to building a business.

Talking publicly about how he needed to make a decision, what advice he followed, it helped others see and understand the hard process of creating a product.

He constantly teaches others about everything he does while creating ConvertKit.

Moreover, he openly talks about everything he does over the course of a year in his annual reviews you can find on his blog.

Everything about what they do at ConvertKit, about his family, hobbies, adventures, investments, and more.

1.c. Educating on frameworks

Another key moment that contributed to the creator movement was when he started to educate people on mental frameworks.

The Creator Flywheels

Nathan was inspired to create the flywheel framework when he was working at an orphanage in South Africa. 

They wanted to provide a reliable water source, but because electricity was unreliable, they mounted a hand-powered pump.

The pump where you drive up and down to bring water to the surface was not ideal because it would take far too much effort to operate so they used a flywheel.

The large metal disk used a rotational force to pump and it was hard to get it started, but it got easier with every rotation.

The same framework can be applied from physics to everything we do online.

You can work hard on scattered things where you can pump everyday up and down for a long time. 

You’ll get results, but it’s gonna cost you a lot, you’ll even fall into burnout.

Or you can apply the flywheel and try to make things as easy as possible.

The rules of a flywheel as he wrote in his blog post are:

  1. Activities flow smoothly from one into the next
  2. Each rotation is easier than the previous rotation
  3. Each rotation produces more than the previous rotation.

With each rotation it has to be smoother, easier, and more effective.

In a podcast he talked about how this flywheel method helped Sahil Bloom

To make a flywheel work you have to focus on one goal.

Sahil’s goal was to reach 1 million subscribers.

Starts with content on social media, driving those into his email list.

Then he takes them to the Creator Network which is a ConvertKit offering where they pair you up with creators and recommend each other after the sign up. 

In email flows he sends two emails a week and uses ConvertKit’s Sponsor Network because they’re selling advertising on his emails.

The money he makes on advertising he invests in ConvertKit’s Recommendation Network.

For every subscriber that comes through recommendation he pays a small amount.

This led him to have more subscribers and grew his list to 500,000. 

By using the flywheel he created a snowball effect.

Nathan mentioned that he applies flywheels to everything in his life using FigJam trying to find the best solutions.

The Ladder of Wealth

This mental framework helps others think about how wealth is made and how it can be a repeatable process.

And it answers the question of why people have small wins moving through different stages, than when making a direct jump on the ladder.

The principle it relies on is that making money is a skill (more skills combined actually) which is something that Nathan learned from Jason Fried from BaseCamp.

So on the ladder you find different environments in which you learn skills on how to make money gradually.

You start from being an employee where you learn skills such as showing up on time, listening to feedback, or being reliable, and money is directly tied to your time.

Then the next step is the freelancing stage where you learn about how to create files for the government, how to collect payment, send invoices, and all.

The next ladder step is about charging by the project which is a disconnection point between what you charge and how much time you spend.

Then you move on to hiring a team and after to creating a product-type service where you learn new skills about money.

Nathan says that you don’t have to climb the ladder in this order, you can jump higher from the start, but that means you’ll have more things to learn in a longer time period so you have to learn to be patient.

It might take you 3 years to go from employee, to freelancing and then starting a business, but if you go from employee to business owner it might take you just as long or more as you have to learn all the skills of the things in between.

On a podcast with Callum McDonell, he gave an interesting insight.

He said when you’re about to start a new business venture you should think about two things: money and skills.

Separate these into two columns and compare what you’re getting from the new venture and think how much value it brings on both columns.

Besides money, you can learn a set of new skills and gain new relationships which are things that can help you later on new projects.

Creating the “Billion Dollar Creator” mindset

Another thing which contributed to the movement of creators is the creation of the “Billion Dollar Creator” podcast.

Nathan and Rachel Rodgers, his co-host, want to instill creators the idea that they can be a billion dollar creator.

“Billion Dollar Creator” is an educational series and live evenets designed to guide creators in capturing attention and transforming it into wealth.

Delving into the success stories of brands, celebrities, and entrepreneurs who have mastered this art, the show provides practical insights on applying these strategies to everyday creator ventures.

The key idea is that to become a billion dollar creator you need to build an audience, just like Nathan did, or any other successful B2B creators.

So, in his blog post he states there are four rules to building a billion dollar audience:

  1. Build more than a personal brand

You can start with a personal brand, but as things evolve you need to move beyond that.

  1. Sell products, not attention

Creators understand that you capture attention and redirect it towards products through advertising and sponsorships.

  1. Drive higher customer value through recurring or repeated purchases

You need to think about “How often can your best customers buy from you?”. Create a product they can buy over and over to increase the CLV (customer lifetime value).

  1. Choose a better business model

I go again into the example with Andrew Wilkinson which I also mentioned in a previous article.

Andrew leveraged the proceeds generated by MetaLab, his design agency, to acquire a portfolio of companies under his investment firm, Tiny Capital. Services revenue isn’t highly valued by the broader market (because long-term cash flow is capped), so Andrew used the profits to buy and invest in businesses that are highly valued (software, communities, etc).

So Wilkinson engaged in a strategic financial maneuver, trading up the revenue quality by investing in businesses that are more favorably valued in the market.

2. Nathan knows how to build and maintain an audience

Because he knew how to build an audience he became so successful as a B2B creator.

Nathan’s Barry has:

  • 28,778 followers on LinkedIn which is not his main channel
  • 13,000 followers on Twitter
  • 4.330 followers on YouTube
  • 10,000 subscribers to The Billion Dollar Creator
  • Plus his own personal newsletter subscribers.

How those he do that?

He wrote a newsletter post a few months back about how to grow your audience if you’re just starting out or your audience is small.

Interestingly enough, the three things he wrote are actually his mantras that guided him all along.

  1. Create every day

By creating something every day you learn to be consistent, and consistency is the key. Why? Because people want to know what to expect from you and when.

  1. Work in public

Some creators are afraid that if they share what they do, their competition will follow right away. This can be true, but sometimes we forget we are already ahead of others.

Or even more, people are hard to take out of their comfort zone and even if they have everything in their face, they won’t always do it. 

ConvertKit valuation is $200 million in 2023 and Nathan Barry and his team managed to hit this number due to working in public: sharing their struggles and their progress.

  1. Teach everything you know

People think they need to know everything before they can start teaching.

But the audience is formed by people who are, as previously mentioned, one step behind you and can find something new in what you say.

People don’t teach because they’re experts; they’re seen as experts because they teach.

  1. Default to generosity

Nathan thinks of “default to generosity” as a life philosophy. Instead of wasting his time wondering how much he should charge or offer refunds, he often thinks the best solution is to give for free.

He encourages people to give a way for free some of their best advice or work because people will instantly notice and will grow on you.

But why does Nathan continue to create content?

Growing an audience is not enough.

You need to nurture it and offer it valuable insights.

By sharing his vision about his company but also about the industry he became one of the most influential thought leaders in the creator economy.

By writing he evangelizes what ConvertKit is doing and being transparent about the company roadmap increases his audience’s trust.

By being involved in creating content he collects feedback from ConvertKit’s community and it’s not just for the product, but for generating ideas to better understand his audience needs.

Besides ConvertKit’s community, or his personal audience, there are also the employees who are looking at him, are analyzing every step he makes and want him to be their guidance on how to make the product even better.

Plus, you cannot ask your employees to promote the company or trust the product if you don’t have an opinion about the industry you activate on. 

Why Nathan is not your typical founder?

Since he’s a creator himself he knows how important it is to encourage others to be one.

And he does just that through everything he does, but most importantly he doesn’t forget about his employees.

ConvertKit stands out in the corporate landscape by actively encouraging and supporting its employees’ engagement in side projects.

It encourages them to develop themselves outside ConvertKit and use the product in their creator tool kit. 

At ConvertKit they believe that creative endeavors outside the workplace can enhance an individual’s performance within the workplace.

But the truth is that to have a company that supports inhouse creators, it must cultivate a culture of creativity and values.

This type of culture helps you create a workplace where every team member feels inspired to bring their unique perspectives to the table knowing that their creativity is integral to the company’s identity.

Because when the company cares for them, they feel a genuine sense of ownership in shaping the company’s narrative and trajectory.

Nurturing this culture isn’t just about ping pong tables and colorful bean bags. It’s about establishing a foundation built on shared values that resonate with every team member. 

And when creativity and values intertwine, it creates a dynamic synergy that attracts top talent and retains it.

To balance the side hustles, ConvertKit created a primary and fair condition: the side hustles should not compete directly with the company’s interests or negatively impact the individual’s contributions to the team.

Other than this, employees can share and discuss their side projects on the company’s designated Slack channel, #side-hustles.

To support this culture of creating creators, ConvertKit recognizes the potential of turning their side projects into full-time pursuits and expresses support for team members who choose to transition their side hustles into their main career focus.

Does all these sound too good to be true?

A while back, Nathan invited ConvertKit’s Creative Director in his podcast.

Besides working for ConvertKit, Charli Marie produces her own podcast, writes a newsletter, conducts marketing site audits, holds 1:1 consultations, and sells digital products for designers.

In the interview, they openly talk about design, about her side hustles, and how you balance that with a full-time job.

I mentioned earlier that ConvertKit believes that having a side project can positively impact an employee’s effectiveness within the workplace.

Well, Kyle Adams is an example.

His side project is about how people can create better newsletters and build incredible experiences for subscribers.

By writing this newsletter and tweeting tips about newsletters he builds his audience, but at the same time he helps ConvertKit top creators to grow their audiences.

Another great example is when you celebrate your employee side hustle, and you can invite them to talk openely about it. For example, here’s the interview Nathan had with his collegue, Isa Adney, that is also a Senior Storyteller at ConvertKit and she is also an author of The Little Book of Big Dreams.

ConvertKit’s incredible culture can be seen in the employees benefits as well.

What striked out was profit sharing bonus, free registration and travel expenses for one conference per year, 401k match of up to 5% of your salary to help you save for the future, plus learning budget, equipment allowance, team retreats, and vacation bonus, vacation days, etc.

Everything is right there public on their website, no need to look on review websites to find something about them.

Oh, and let’s not forget about the fact that Nathan refused to sell ConvertKit to Spotify in 2021.

Nathan wrote an article a while back about the 15 lessons he learned building his company and one of the things was sharing the profit.

He said that sharing 50% of the profit with the company made everyone spend money efficiently.

He is also very transparent when collaborating with other creators and helping others to succeed.

In a LinkedIn post he talks about the partnership between him and Sahil where they created a playbook for clients who want to scale their newsletter and need strategy and operational support.

Creates small projects for a bigger cause

The Secret Money Newsletter

The reason he created The Secret Money Newsletter is because he talked a lot about how to make money but little about what to do with them once you have it.

His passive newsletter is a 12 email sequence now and is sent out every Friday. 

Before buying it for $149 one-time payment, Nathan tells his audience that it’s for creators who are already earning over $200,000 per year.

So don’t buy it if you’re early in your career.

Or do it if you’re curious, it’s up to you.

In this newsletter he talks about what he invests in, how to splurge money, about how to raise kids when you have money, and more.

It currently has 500 subscribers and an impressive 87% open rate, and made Nathan $50,000.

The Billion Dollar Creator 

We talked about “Billion Dollar Creator” earlier, which is this podcast about teaching creators to capture attention, build an audience, and transform it into wealth.

On this podcast he had an impressive list of guests, such as Sahil Bloom, Codie Sanchez, and Sam Parr.

He and Rachel even launched a podcast tour for the “Billion Dollar Creator” show. 

The tour involves recording podcast episodes in front of a live audience and offers attendees the opportunity to meet and network with fellow listeners, as well as the hosts.

The ticket, priced at $39, includes access to the live podcast recording, a meet-and-greet networking event, and an exclusive “Billion Dollar Creator” t-shirt. 

The tour aims to engage with the audience, create a sense of community among listeners, and provide a unique and interactive experience beyond traditional podcast consumption.

The Art of Newsletters

He started his podcast back in 2020.

It’s a podcast where he talks about newsletters and how to make money as a creator with different guests such as Kate Bourgoin, Ali Abdaal, Cody Sanchez, Sahil Bloom, Alex Lieberman, and a lot more.

The reason why he started the podcast was to have a voice in this creator industry and to help others grow.

But his favorite part is turning successful online creators into his friends.

“My favorite part is how many new friends I’ve made. There’s nothing better than a podcast (okay, maybe a conference) for turning people you follow on the internet into friends.”

The Founder Creator Era

We are living in the era where founders can be the creators and build audiences.

Starting from PeeP Laja, Rand Fishkin, Alex Lieberman, Codie Sanchez, Peter Caputa, obviously Nathan Barry, and so many others.

Peter Caputa, the Databox CEO, says that he posts daily on LinkedIn to share the company’s vision, validate plans, and evangelize them to a broad audience.

But there is more than just that.

He gathers insights and iterates on the company’s initiatives. Unlike traditional methods, LinkedIn allows for a quick exchange of ideas and opinions, facilitating rapid adjustments as needed.

He can collect instant feedback that helps confirm that the company is on the right track and allows for adjustments as needed.

Codie Sanchez went from journalist to investor to partner in a fund, and she also runs a 500,000-subscriber newsletter called Contrarian Thinking where she teaches unconventional ways to make money.

Besides being the CEO of Sparktoro, Rand Fishkin is also helping people do better marketing creating the 5-minute whiteboard videos.

And Nathan who is not just a B2B Creator, but one of the best examples on how to leverage B2B Creator as a founder.

So, founders need to find their voice to shake up their industry and share their thoughts and insights.

This is why Nathan is doing his podcast tour, writing his newsletter, and going as a guest to different podcasts.

Founders need to create a bridge between their company, their beliefs, and their community.

Nathan is doing this by creating regular content about what they do at ConvertKit, what he believes in, and what he creates.

Plus, a published content for a founder can be like an ad that promotes his company.

It doesn’t cost anything, it’s evergreen. It doesn’t just boost a team’s confidence, but it can get new clients or new partnerships.

Also, the whole purpose of the Craft + Commerce event created by ConvertKit is to get closer to their community. 

For ConvertKit it’s a great opportunity to connect with their customers and the guests get the chance to talk to ConvertKit’s employees, to take inspiring keynotes, and participate in workshops and creator meetups.

What B2B Creators can learn from Nathan

1. The founder mindset

One of Nathan’s mantras “teach everything you know” reflects the founder’s responsibility to share insights, offer guidance for others and help the others grow.

He built a platform that helps others create wealth telling ConvertKit’s whole story, supporting his employees, creating podcasts, newsletter, and events.

2. The creator behavior

The Billion Dollar Creator podcast, the Art of Newsletter Podcast, and various blog posts exemplify his dedication to building content projects that educate and inspire others. 

This approach aligns with the idea that creators don’t wait to become experts before sharing knowledge; rather, they become recognized as experts by virtue of teaching and contributing to the community.

Nathan’s emphasis on daily creation, working in public, teaching everything you know, underscores the importance of consistency, transparency, and a giving mentality in nurturing a successful creator mindset.

3. The colleague mindset

Being a founder and a creator, Nathan knows how hard it is to make products work and the hard work and consistency that goes into that.

His colleague mindset is clearly visible as he invites his colleagues to his podcast to discuss their side hustles offering them support like he did with Charli Marie and Isa Adney.

Plus, the same mindset is applied to ConvertKit in its unique approach to support employees’ development outside work.

Having a company where employees feel that they’re encouraged to grow will make them want to be better and stick around in your company giving their best.

Final Thoughts

I want to end this article talking about Nathan’s unique blend of mindsets, from founder to creator to colleague, which has profound implications for ConvertKit’s company culture.

It’s incredible how all of them challenge the traditional corporate structures showing the true potential of aligning personal, professional growth, and employees growth. 

This is something companies should keep in mind if they want to be successful.