Her mom used to say that she was really confident when she was a kid, and she felt she lost her confidence along the way.
But I say only an ambitious person could do what she does.
She definitely regained her confidence when she realized she likes marketing and stopped living her life on inertia.
Who is Stephanie Smith?
Before joining the marketing path, Stephanie was on a different path finishing Engineering Chemistry at Queen’s University in Canada and later working as a researcher and analyst.
But since she felt she’s not on the right path, she rapidly switched departments and got involved in marketing.
She scaled Toptal‘s hyper growth design function, then led Toptal’s Publications team and enabled millions of readers worldwide to access expert-level content across 6 publications: engineering, design, finance, project management, product management, and the future of work.
There she ended up leading the product and growing it to 15k+ paying subscribers, before the company got acquired by HubSpot. That’s how she became Marketing Director at HubSpot, spearheading their work with creators.
She constantly worked on side hustles since she went into marketing and code-learning because she loves making products, coding, and hopping across the globe.
She learned to code from a Udemy course she bought for $20 in 2018 and since then she created multiple projects that went to #1 on Product Hunt, including winning an award for Inclusion and was nominated for the Maker of the Year.
She also maintains updated her personal blog where she writes about remote work, productivity, and women in tech.
What does Stephanie do that makes her great?
1. Working on side hustle projects
In 2018 she had a huge desire to learn to code, and due to that she managed to create several side projects.
- Nomad – which is an exploration tool for coworking retreats
- Make Yourself Great Again – which is a calculator that shows you the time you waste each week and year and encourages you to do more activities that bring you joy and new skills
- Eunoia – a website with a list of words that cannot be fully translated from one language to another
- And lastly, FeMake an incredible data provider about the female representation in the maker community on Product Hunt. With this project she won the Inclusion award on Product Hunt 2018.
In 2019 she started to write on her blog about remote work, about learning to code, and women in tech, and reached 400k+ pageviews and thousands of subscribers in its first year.
As she gained more confidence in her skills, in 2020 she wrote a book called Doing Content Right.
By the end of the year Steph made $60K selling the book and by 2022 she wrote on Kernel that she made more than $220K.
In total she sold 4,842 books, but unfortunately we cannot really estimate the correct total price of the book.
Why? Because just like everybody else who starts something, she had her insecurities about money.
In a podcast she mentioned she asked her network on X/Twitter if people would pay $10 for her book and she obviously got mixed feedback.
There were people saying they would pay even more, and others who were not interested at all.
Her advice is to find a mechanic to get the answers you need.
She started to sell the book for $10 on Gumroad and with every batch of 30 books sold she increased the price by $5.
Once she had enough data she looked to see at what price did more people buy the book at set the price at $30.
Over time she increased the price since more and more people liked the book and had the joy to receive social proofs from industry leaders such as Harry Dry, founder of Marketing Examples who said
I’m jealous of how good this is. The best stuff I’ve read on content marketing by A. LONG. WAY.Harry Dry, Founder MarketingExamples.com
So the thing you need to remember is that the price you set is not permanent and you can adjust it once you have data.
But you should charge before you’re comfortable because when you charge more people tend to trust that what you’re giving them is valuable.
Now you can find Steph’s book for $150.
There is one more important thing I want to point out about the way she wrote this book and I believe it’s something most of us struggle with when creating something.
She wrote the book in 7 weeks.
How? She realized that if she is excited about something she should put herself to work and not let go until she finishes the project.
This is because of procrastination – something we are all facing.
And she’s very aware that if more creators would put themselves to work when they are at their highest enthusiastic moments they would finish their projects faster than they could imagine.
After Steph’s book success, in 2021 she created a course called Unlocking Hidden Hours: Doing Time Right.
The course is focused on optimizing time management and productivity and was written in Notion.
The imagery is very similar to her book and she offers frameworks, actionable exercises to create more time, different templates, and more.
This course also sells for $150 on Gumroad and was made in… 20 days.
Also the year 2021 was the year she started her podcast together with her husband Calvin Rosser called “Shit You Don’t Learn in School”.
In this podcast they share stories and insights to help others improve the quality of their personal and professional life.
Their hope with this podcast is to make people at least 1% better at navigating the waters.
2. From The Hustle to leading HubSpot Creator Program
How did she get to The Hustle?
When she worked at Toptal leading their publication she started to write on her personal blog.
Sam Parr saw one of her tweets where she wrote about one of her best blog posts How to Be Great? Just Be Good, Repeatedly and reached out to her saying he wants to hire her for this thing called Trends.
Trends didn’t even exist at the time, but once it launched Sam hired Steph.
In Nathan Barry’s podcast she tells him that she was anxious not knowing if she’ll be good at her new job since she had no professional writing background.
After almost a year writing the Trends she ended up leading the product to millions in ARR at 15k+ paying subscribers.
Once The Hustle was acquired by HubSpot, she led their creator program being the Director of Marketing.
She did not talk a lot about her role on HubSpot, but while there, she continues to balance her full-time job with her side projects.
She finds it freeing to have side projects separated from her day to day job.
The reason for that is because many people quit their job to follow their “passion” and it ends up destroying them.
So her side projects are strongly connected to her productivity.
She likes to work in sprints only when she is excited and not pressured to work.
She describes her workflow based on Naval Ravikant’s analogy “work like a lion not like a cow“, referring to the fact that lions rest most of the day, but sprint when they need to as opposed to cows that constantly graze.
3. Being a podcast host at A16Z
She is now the face of The a16z Podcast.
a16z is a private American venture capital firm, founded in 2009 by Marc Andreessen and Ben Horowitz and created their podcast in 2014.
Fun fact: The reason it’s called a16z is because there are 16 letters in Andreessen Horowitz full name, between the A of Andreessen and the final Z in Horowitz.
The a16z team approached Steph and wanted to hire her.
She believes that the reason for their decision was that she was the right combination of someone who had experience with podcasting, who was helping HubSpot build their Podcast Network at the time, and maybe her track record of working towards interesting things had to do something about her hiring.
She describes what the a16z team did as hiring someone for slope not y-intercept where you hire someone who you believe can learn quickly and deliver good results they can get rather than where they are today.
Steph is employed full time at a16z podcast as she does almost everything: preparing, researching, recording, working with editors, publishing it, and promoting it.
She says it’s the hardest job she ever had, but the easiest if she thinks that she’s not grinding her mind away in an Excel spreadsheet.
She says it’s difficult to be a host to know what questions to ask, what parts of your personality to share, how to keep people engaged.
Everyone can say they can host a podcast because it sounds easier than it is.
But the hard part is about the psychology, the human interaction, besides the way you speak, the voice level.
She works better if she has feedback or some data she can rely on, but the feedback she receives for podcasting is conflicting (why do you interrupt, why don’t you kind of feedback), which makes it harder to know how to be better.
I perfectly understand her.
When I started working on my podcast, I had a lot of emotions every time I began to speak with someone.
I didn’t know how prepared I was, and I was unsure of my readiness. I also had concerns about asking the right questions or bringing out a compelling story from the interview.
However, over time, I learned that if I made the guest feel comfortable, at ease, and, more importantly, if they felt that the focus was on them rather than me wanting to do a podcast with them, then the guest would feel good, comfortable, and speak freely.
But every time I hit a record, I still had emotions.
And it’s so normal to have emotions because you are a channel for delivering the message, and you want everything to be perfect.
When Steph joined the podcast she did longer and shorter podcast episodes (1h 30m vs 15m) but now most episodes don’t go that deep, having around 40 minutes.
One more important thing I noticed is that the podcast has more consistency with around 5 episodes per month, whereas before Steph they had months when they did not post anything.
Another thing that has improved on the podcasts is that besides the episode summary and notes, there are two new sections.
One about the topics covered with the timestamps so you could jump to the topic of your liking similar to what you can do on YouTube.
And another one about resources where you can find information about the guests and all social links to a16z podcast and to Steph’s X/Twitter account.
What can B2B creators learn from Stephanie
1. Having a side hustle even when you have a full-time job
“But I don’t have time”.
It’s something most of us say to ourselves and sometimes out loud to others.
It’s time for us to view “me time” differently than as a break from work and view it as an opportunity to focus on personal growth and align with our long-term goals.
Steph has an entire article about not needing to quit your job to work on side projects where she encourages readers to use “me time” more intentionally.
Invest this time in endeavors that contribute to personal development, so we could harness the power of consistent effort over time.
Make “me time” purposeful and aligned with your aspirations.
It may sound hard to take action, but just think about how much time you spend on distractions each day that could go into creating or learning something?
Take Steph’s calculator and see how much time you could actually have on hand if you’d focus on things that matter.
So you can definitely become a part-time creator from 5 to 9 or work on weekends, or do what Steph’s doing, work on your side projects when you’re really excited about them.
You can still keep your day to day job where you can learn from people smarter than you and get paid for it and work on other projects that bring you joy and maybe open the doors to new professional opportunities.
2. Read the signals before they become a trend
Steph talks about her journey of acquiring tactical skills in Danny Miranda’s podcast.
She says that she learned a lot navigating various websites and utilizing tools such as Ahrefs and SimilarWeb to understand the world we live in and how others build their own online businesses.
But contrary to what you would expect, she emphasizes that these tools did not generate her ideas.
They were just validating her concepts.
So how do you spot signals?
By having a curious eye, paying attention to what happens in your day-to-day life, and asking the right questions, you get new ideas.
That’s when Steph uses a tool like Google Trends to validate what people actually find interesting.
To her everything is an interplay between observation, inquiry, and data validation, and that’s how you can come up with innovative concepts.
I say the best way to test your idea is to write a post about it on your favorite platform such as LinkedIn, Twitter or write a blog post, and hit the publish button.
You’ll immediately receive the data that Steph searches for on Google Trends through your audience, through the way they will engage.
This will also give you a hint if you’re on a good track with your ideas and if you should focus your attention in the same direction to gain more attention.
3. Don’t just create content – Create experiences
Each of Steph’s side projects served a practical purpose, contributing to the overall user experience.
Like Nomad, which is an exploration tool designed for coworkers, or Make Yourself Great Again, which urges people to reflect on their habits.
These websites deliver more than information, they create an interactive and participative experience which is why Steph is so successful with what she does.
By prioritizing the needs and aspirations of her audience, Steph goes beyond the surface level of content creation. She designs experiences that resonate with users on a personal level.
So you should identify the needs of your target audience and create your content, solutions, tools, or insights that directly contribute to overcoming those challenges.
And then actively seek and embrace feedback from your audience and iterate improvements to ensure that the content continually evolves to meet the changing needs and expectations of your audience similar to what Steph has done with her book.
What does Steph want to do in the future?
She wants to be better and earn more because having an amount of wealth can help you make a higher impact on others, work on whatever you want, hire people if you need help, and you can just think bigger.
I think the best ending for this article is a powerful message from Steph that we should all keep in mind: