How to turn your ideas into currency - ft. Sahil Bloom, Justin Mikolay, Li Jin, Packy McCormick and Janel Loi.

Deep dives into the business models and approaches of the people who have made a living from their ideas online. (Part 2)

Welcome to part two of a mini series to the question Can you make money online as a thought leader?

If you didn’t catch it yet click here for part one, to get my take on this exciting and viable career path as I explored the business models of successful creators Anne-Laure Le CunffDavid Perell,Codie SanchezSteph Smith,George Mack and Josh Spector.


Image Credit TylerDale

If you’ve been following you’ll know that lately I’ve been talking about the nuts and bolts of having an online presence as a founder, from my own perspective as founder of The Ask and what I learn coaching other founders and creators.

I draw the distinction between people who own businesses where they are the product and those with a business whose products/services benefit from their personal brand (ie. because of who they are, people are more inclined to buy from them).

This post explores a certain breed of business owner who sits somewhere in the middle — the creator/thought leader — who makes a living from their ideas. This living is then compounded by their large public profile which creates revenue either directly or indirectly.


New here? Join me if you’re building your entrepreneurial career and want to succeed faster every other Wednesday.

Today, we are profiling more successful creators and their business models: Sahil BloomJustin MikolayLi JinPacky McCormick and Janel Loi.


Sahil Bloom

Website|Newsletter |Twitter

Why I’ve included Sahil:

It’s fair to say that Sahil’s made a bit of a splash online lately. In a matter of months he has acquired tens of thousands of Twitter followers thanks to his ability to tell relatable stories designed to demystify topics that can be intimidating to novices (investing, personal finance, economics).

He started writing his newsletter in June 2020 (around the same time as this newsletter!) but unlike me in this time Sahil has reached 28,500+ subscribers. Sahil teach me your tricks!

Sahil’s content was borne from a genuine problem and need in the world that he saw as a result of the covid-19 pandemic where millions of peoples’ livelihoods felt threatened they sought more financial advice and understanding to support themselves. He says “I couldn’t see why such smart people were unable to apply the concepts they were taught in their everyday lives” — it was out of this determination to demystify these concepts that he moved into financial education as a pursuit online via Twitter and his newsletter.

He feels that a society that lacks financial education creates structural inequalities and knows that for young people today they are unlikely to learn this information in their own homes, but are likely to turn to social media. He believes that better education in finances is a pathway to opportunity becoming more evenly distributed around the world and that this has been held back by financial institutions who insulate themselves from disruption by overcomplicating topics which, in reality, are not so complex.

Sahil felt that people who were writing about money on Twitter were doing it an unnecessarily complicated way. He became determined to break these concepts down through anecdotes and stories to the everyday person in a relatable manner.

Sahil takes his learnings from his day job which he applies directly to his content. On his LinkedIn profile he shares “I have built a media platform related to business, finance, and decision-making.”

He quickly saw how much value the Twittersphere took from his content as they followed in their droves.

Ideas Sahil covers:

Finance, money, business, economics, and history education and mental models

How Sahil makes money

Sahil is not a full time creator as his day job as Vice President at a PE firm keeps him comfortable. He leads Altamont’s consumer products and services sector with active board roles in their portfolio companies.

His content does make him money though. He creates what he describes as ‘High-signal curiosity inducing content’ with his newsletter.

Sponsors pay Sahil for features in the posts, and he also captures a selection of curated job openings using Pallet, where Sahil is a partner to the company.

How much does he get paid to feature a job? See below.

Sahil is also a course creator for Maven where he gets paid a % of the overall course revenue, his latest one you can join is on audience building.

What we can learn from Sahil:

On this podcast he described himself as being just another ‘30 year old finance guy’ who, with some trial and error, has created side projects that have allowed him to capture a sizeable niche and influence in the online space as a financial literacy influencer.

You could argue that he became an influencer by accident, as a result of his genuine desire to help, powered by a knack for story telling.

His personal brand skyrocketed in short space of time thanks to consistent and regular posting, a twice weekly newsletter and being proactive with media coverage.

But above all Sahil has a mission. To make financial knowledge consumable by demystifying concepts and making them accessible to everyone.


Justin Mikolay

Website| Newsletter | Twitter |

Why I’ve included Justin:
Justin’s path to becoming a creator in this space is one of the most interesting journeys yet. With degrees in political science and international relations he worked for the US Navy as a nuclear submariner(!) before moving into more managerial roles that later transitioned to speechwriting for senior US government officials including Mattis, Petraeus and Panetta. This period taught him how to listen effectively and channel people’s voices and opinions in written form.

He was soon tapped up to join leading software company Palantir as an Evangelist, where they created a joint venture, a tech company for consumer content management. Justin became enraptured by digital ‘commonplacing’; tagging and categorizing information online. Whilst tools like Roam research are now popularising the concept of storing your digital brain, at this time Justin’s company never quite made it and he moved into sales.

His foray into Twitter began as his new sales role demanded he had a greater online presence. This time spent in Twittosphere soon took Justin down wormholes where he unlocked a deep curiosity for how other people think.

His two worlds of speech writing and digital commonplacing then came together as he began distilling Twitter timelines of prominent people to understand their worldviews. Justin created multiple ‘Big Idea Summaries’ which took him to internet famous status. Examples below (you’ll recognise the names from this series :))


Ideas Justin covers:
Writing, the creative process, digital entrepreneurship, online course creation.

How Justin makes money:

His Twitter exposure landed him a role at Gumroad (where creators sell digital products) as a Senior Writer and podcast host, where he learns about creators and entrepreneurs at the top of their field. This role has not only covered the bills since Justin quit his job but also leaves him room to explore his own creative ventures, all of which focus on helping creators to build information products and courses.

He has been supporting Eric Jorgenson build the Leverage Course as his business partner and was then selected for the inaugural cohort for Maven instructors. This has allowed Justin to teach his own course, The 10x Creator Course from Maven (notice a theme here) which helps people turn big ideas into digital products. He said this course has changed his life and he’s had a blast teaching it, with three new cohorts coming up. I’m very interested 👀 

More recently Justin has launched a passion project, The Creator Manifesto, in the form of an NFT — bidding is ending today if you’re interested!

What we can learn from Justin:

Throughout his pursuits Justin has been led by his intellectual curiosity. He’s befriended people on Twitter he admires and gained great exposure as a result. Channeling other creators work as a creator seems to be a theme of this series, and Justin showcases a best in class version of it.

He’s a collaborative and supportive presence on the internet, and he was also kind enough to support this post he shared his entire story with me in the DMs of Twitter.

He said his hope is that his “presence and participation online is positive and inspires more people to create and pursue their creative dreams”.

I feel that passion and energy from him and know others do too.


Li Jin

Website | Newsletter | Twitter

Why I’ve included Li:

Much like others in this series Li is a creator for creators and very much a leading voice in this space.

She has been described as:

Passion Economy pioneer” “The authoritative voice in the space”

“Essential reading for anyone building a community in the next 10 years”

“The best thinker out there on the future of being a creator on the internet.”

“The Queen-maker of passion economy startups”

Li stands for a mission greater than herself, which is to grant more worker control and ownership to those participating in the sharing/gig/creator economy. She sees the answer to these problems of ownership as being solved with co-ops, DAOs, better distributed capital and ownership. She sees decentralization as extremely important to the health and longevity of the creator economy as captured in her recent post The creator economy is in crisis. This was written before the OnlyFans debaucle which Li Jin said has had her ‘blood boiling’ since CEO Tim Stokely has captured billions of dollars of value from the creators who are now left in the lurch since adult content has been banned.

Ideas Li covers:

In her own words Li’s work explores two broad themes.

i) The Passion EconomyHow people can make a living from their passions and creative skills
ii) Consumer trends & analysis: How macro trends are impacting consumers’ lives and work

How Li makes money:

Li makes money through her content, investing in companies and digital platforms and products.

Means of Creation, Li Jin’s talk show with cohost Nathan Baschez, is a part of Every, the collaborative content studio. Every hand picks writers and content creators to produce what are essentially columns, and Li Jin’s is focused on trends and updates from the passion economy. Every is a subscription based media platform that has some free content but mostly gated, charged at $20 per month. Subscribers get full access to all Every content for this price however, and Li Jin and other creators get a cut of overall sales.

With a YouTube channel and podcast for Means of Creation, opportunities for advertising and sponsor based income are endless.

As Managing Partner at early stage VC firm Atelier focused on the Passion Economy, Li has made investments in the likes of Substack, Patreon and Icebreaker, where outsized future returns seem likely.

She has also co-created Side Hustle Stack, a Fiverr alternative where companies can find freelancers for gig work and vice versa which takes advertising sponsors. Side Hustle Stack is the largest resource of its kind for flexible work opportunities, and sponsors can feature their products and services to an audience of gig works for $400 per week or $1500 per month. This makes sense that she’s building a tool to help people monetise their passions and skills


What we can learn from Li:

Li was somewhat of a first-mover in the creator economy space. She was able to spot the tide turning having been an investor at a16z for a number of years before setting up shop as a self employed creator and investor. Now, writing and sharing about the trends from a macro perspective Li is also putting her money where her mouth is with investments into companies and people evolving the creator economy landscape towards more equally distributed ownership.

Li pays attention, she challenges and she sees around the corner. Li has amassed a loyal following who take her lead on the important issues, which is she not one to shy away from.


Packy McCormick

Website | Newsletter | Twitter

Why I’ve included Packy:

Packy began with 300 Twitter followers in April 2019 and is close to 60k today. How?

He turned to the content creation business as a result of the pandemic, before which point he had been planning an IRL social community which hit a standstill for obvious reasons.

Looking for a new income source, he turned to writing. Remember David Perrel from the previous post? Packy learnt from David and went from a guy with a few unfinished draft posts on Medium, took the Write of Passage course and today has 70k email subscribers for Not Boring. You read that right.

He started out writing about sleep and community, and through iterations now covers topics around business and finance in a fun way where he gets to learn and so does his audience alongside him.

Packy grew by focusing on writing well and Tweeting his work to grow his subscriber base. It was posting on Product Hunt which grew his subs from 1000 to 2000 almost instantaneously and from there on it has been rocket ship growth.

By building in public and sharing stats like the one below with his audience, Packy has been able to bring others along for the ride who enjoy being a part of his trajectory and contribute through sharing his work along the way. His goal in sharing?

“To show that this [newsletter] is not some like mystical thing that happens. It’s just about putting in the work over time and having fun with it and finding something that you really like doing.”

Ps thanks to Nathan Barry who is the source for much of this post on Packy. Watch here.

Ideas Packy covers:

“Fresh essays combining strategy and pop culture” which covers topics such as business strategy, community, tech, and real estate, striking a balance between fun and educational. It’s been described as “your best alternative to Business School”.

How Packy makes money:

With that subscriber base, Packy could have put his content behind a paywall and made money with ease. However in the talk with Nathan he explains his decision not to… The typical subscriber to paid conversion metric on Substack is 10% but he doesn’t know many people who exceed 5%. So even with a healthy 5k subscribers paying $10 a month he would make $2,500 a month, which for a father in NYC trying to pay rent from the newsletter would not quite cut it. You have to keep increasing the volume of content to make this viable, which is hard to do when you’re only one person.

Packy instead chose sponsorship but realised he’d still need more content so started posting twice a week and offered slots to his network - which soon filled up.

The three kinds of sponsorship include both Monday top of newsletter sponsorship (for $5000), Thursday ($3000) and the Thursday deep dives which are investment memos for companies Packy is interested in and doing investment due diligence on. These are charged at a whopping $20,000 per piece. Companies are still lining up to be covered, as $20k to them can feel like a bargain for all the exposure in the form of customers, hires and investors.

With these three pieces he says he is making more than he was as an executive of a startup that had raised a hundred million dollars and can make investments in startups. He says “I’m pretty nakedly commercial about the whole thing” in the way he’s designed the business model to reinforce each of his efforts.

Alongside the newsletter Packy invests for Not Boring Capital — you can see his portfolio here and is on attempt two to build his IRL social club (for NYC based folks for now) learn more and apply here.


What we can learn from Packy:

Start before you’re ready, and keep iterating to find what works.

At the start of 2020 he had 350 subscribers and aimed for 1k that year. Seeing the growth he was able to quickly adjust his goals and strategy for monetisation.

He has been open with his audience about his journey, what is going well and what isn’t.

Importantly, he puts in the hours. Writing is a lot of work. 10k words per week to be precise.

But the returns are sure there.

When he was at 33k subscribers he was at $40k revenue per month, so at 70k subscribers today who knows where this goes…


Janel Loi

Website | Newsletter |Twitter

Why I’ve included Janel:
A voracious reader, curator and creator, Janel is among one of the most curious minds online. She reads 150+ articles weekly and brings her learnings together for her newsletter BrainPint which curates what she’s learning to provide readers with tools to sharpen their minds. With 3,600 subscribers and counting, her archives provide a wealth of resources for creators such as 'How I curate’, ‘How to spot trends’ and ‘Work on what matters’.

In nine months she went from fewer than 50 followers on Twitter to launching two successful Gumroad products and getting hired by On Deck, and has earned tens of thousands of dollars from her Notion "Operating Systems." She also has weekly digest for investors in publicly listed SaaS companies here.

At One Deck she’s become a pillar in the no code community, as Program Manager for their No Code cohort. (For anyone new to the term, no code tools can be used to create the same scale from software as coding can but without, well coding). Essential for hacking growth as a solo maker or creator. I’m a big Zapier user in my own business.

Ideas Janel covers:

Her work sits at the intersection of tech and the creator economy and covers topics relating to thinking well.

How Janel makes money:

Alongside her day job with On Deck (which she secured thanks to building an online presence) Janel makes money as a maker via her newsletter which right now is free but has potential to go behind a paywall or receive sponsors like the others. Janel accepts coffee donations from those who enjoyed her work via ‘Buy me a coffee’ links and she also curates jobs for her readers again posted on her own Jobs board on Pallet.

As a maker Janel has of course created a product on Gumroad, her comprehensive Newsletter operating system promises buyers with all the tools to launch, manage and grow their own newsletter. Its $49 or $130 including a consultation with Janel herself. These figures soon amount to some good money, she exceeds $35,000 so far. Source.

What we can learn from Janel:

Janel started out playing with no-code tools and writing BrainPint without which, her products wouldn’t exist. The newsletter OS was built out of seeing a gap in the market for products that supported other newsletter writers, as a newsletter writer herself.

Self-described marketer Janel knows that not only does success in the creator space rely on quality work but also on a successful marketing and distribution strategy. Janel has driven demand for new Newsletter OS with a successful newsletter, and vice versa.

She’s also carved a fairly tight niche in topic that creators are always hungry to learn more on, as evidenced by her huge growth in a short time span (she had 57 followers on Twitter in Jan this year.. today 11k).

I have a feeling Janel has many exciting developments up her sleeve we’ll discover soon.


Concluding thoughts

Soo we’ve come to the end (for now)! I hope you enjoyed the deep dives into the business models and approaches of successful online creator, thought leaders and makers. I sure enjoyed compiling them.

The is much we can learn but one thing stands out for me — there are so many ways to make money online from your ideas today.

You are not limited to a particular monetisation strategy or even needing to start with a big audience.

My key takeaways?

Collaboration is king. Sharing and promoting others’ work supports your own.

Find a business model that suits you. Your temperament, time availability and strengths

(if you need help figuring this out for yourself my piece below could help)

The Ask.
How to decide what to work on so you can actually enjoy your business
Hi all Back in your inbox with more advice for your entrepreneurial career path. Today we’ll continue to get granular on the question of whether you are creating the right business for you. This is a problem I’ve doubled down on: supporting entrepreneurial people to build the right business for their unique talent and find conviction in their idea in the……
Read more

Test and iterate ideas and assumptions. Where you start is unlikely where you’ll end up, but if you listen to your audience, try new things and build in public you’ll figure out the perfect fit for both your content and your monetisation strategy.

Make use of the tools built for creators. Substack, Maven, Twitter, Gumroad, Pallet, Product Hunt…. the tools are out there to build a living online from your ideas so go use them to your advantage.

Follow your curiosity over trends. Its clear a lot of work goes into the successful newsletters, courses and communities we’ve learned about. Pursue only topics you would write about for free (as you will start off here for a long time!)

Stay in your own lane. Whilst we’ve heard about themes here there is no one size fits all approach so trying to copy others is not going to give you the unique vantage point and perspective audiences crave. Find your own thing and keep at it — growth is inevitable if you keep showing up.


What about the other creators?

There are wayyy too many interesting prolific creators to mention, but a short list of the people who I would have loved to have covered given more time: Sari Azout, Tiago Forte, Nat Eliason, Tae’lur Alexis and Jad Esber.

Another piece in the pipeline perhaps….


What’s happening at The Ask HQ.


Event with General Assembly for new and aspiring entrepreneurs — Wed 15th Sept.

TICKETS AND INFO HERE.

I’ll be moderating a panel with other entrepreneurs for General Assembly —Started from the bottom now they’re here — to dissect founders’ starting stories.

Join us to hear about starting a business, topics such as mental health, pressures of the industry and how founders have got to where they are today. If you want to be inspired in your own business building journey then do grab a ticket - they are free!


1-1 Coaching with Ellen for Founders and Creators this September

I support founders + creators to move forward with their businesses, get clear on what they are building, their vision mission and purpose and take the right action to make it happen. Book a free discovery call now to explore working with me on your business this September, I have two slots available.


As always thank you for reading, until next time ✌️

Ellen Donnelly, Founder + Chief Coach, The Ask.