Sam DeBrule Profile picture
Aug 23, 2021 13 tweets 6 min read Read on X
In 4 years, Jamila Souffrant took @JourneyToLaunch from nothing to a six-figure personal finance business.

Her podcast has over 2 million downloads.

This is the story of how a bootstrapped entrepreneur is building the media empire she wants to see. Image
Jamila had no plans to make Journey to Launch (JTL) a business until a regular commute brought on an existential realization.

She and her husband Woody saved $169,000 in 2 years, with a growing family, so that she could leave her corporate job and focus on JTL full time. Image
Jamila first got into personal finance through the #financialindependence movement.

She set a goal of aggressively saving money and retiring at 40.

In 2016, she and Woody saved $85,000.
In 2017, they saved $84,000. (h/t @RyanDerous for Forbes). Image
During this period, Jamila tried several side hustles, from digital magazines to a vending machine business to real estate.

They failed, but she was learning.

“I could fail and I would be ok,” says Jamila (h/t @behindherempire for @dotLA)
Jamila’s ‘big idea’ for JTL came in 2017.

She’d seen from experience how the personal finance space lacked diversity at the time.

She wanted to create a space that shared successful Black and female financial stories.

She began JTL as a blog that year.
JTL stayed on the side until 2018, when Jamila was pregnant with her third child.

During one long commute, she realized how burned out she was from juggling her job and her passions.

She decided to form an exit strategy and focus on JTL full-time.

Image
Jamila and Woody created a fund to bridge the gap until JTL brought in revenue.

They stopped adding to retirement accounts, built cash savings, and got a home equity line of credit for emergencies.

It covered JTL’s first 2 years of operations.
Jamila made JTL official quickly. She...

• Created an LLC and filed her trademark.
• Opened up business bank accounts.
• Read @MikeMichalowicz’s Profit First for guidance.

Then, she got down to making the best personal finance-driven podcast she could. Image
How did Jamila grow JTL to 2 million downloads in 4 years?

1. Great content - “At the end of the day, you need your audience to like what you say.”
2. Consistency → she’s posted every week since she began
3. Collaboration with other creators, like Bola Sokunbi of @CleverGirlCGF Image
In those four years building her business, Jamila has created multiple income streams for @JourneyToLaunch.

Here’s the breakdown of her 2020 revenue:

• Affiliate income - 42%
• Brand collaborations - 35%
• Products - 18%
• Speaking + Writing - 4%
• Sponsorships - 4%
Journey to Launch has experienced its challenges.

On JTL’s 4th birthday, Jamila announced the end of her membership product.

The challenge of bringing in members and battling subscription churn was out of alignment with Jamila’s priorities.

It had to go.
Now, Jamila is focused on launching high-quality products, including a book she’s pitching to publishers.

Jamila’s advice for people looking to make the leap into solopreneurship?

“Find something you want to see and create it.” Image
Enjoyed the Jamila's story?

Working on an idea of your own?

Join the Heyday Creator community.

Every week experts like Jamila share how they got their independent businesses off the ground: links.heyday.xyz/slack-community

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More from @SamDeBrule

Jun 28, 2022
I’m fired up to share that Heyday raised a $6.5M Seed led by @kevinthau @sparkcapital

We’re sharing our pitch deck as a resource for founders trying to raise in this environment 👇
@kevinthau @sparkcapital A deck alone isn’t enough to raise money

But it does determine whether or not investors meet with you

And it all starts with an often-overlooked slide...
@kevinthau @sparkcapital The Title

Investors see god knows how many decks each day

Grab their attention immediately.

(huge thanks to our friends @order for designing our deck!) Image
Read 21 tweets
Apr 4, 2022
Heyday is live on @ProductHunt today!

In just 6 months we went from:

Idea > beta > @FastCompany feature > 150 paying subscribers > launch

Here’s how we did it: 🧵
First, we are not an overnight success story

We struggled for 4 years with our previous company (Journal) before @samiur1204 and I shut it down to start Heyday.

50,000+ people tried it, few stuck around

It was a worse version of more popular, better-funded tools
We started by setting ground rules

• If it’s not differentiated, it’s not worth building
• Only work on what we're uniquely capable of making
• Fun is mandatory
Read 11 tweets
Oct 12, 2021
Melanie Perkins co-founded Canva when she was 19 years old and still in college.

Last month, the company hit a $40 billion valuation.

This is a story of how two gutsy Australian entrepreneurs convinced Silicon Valley to fund their dream and change the world of design forever.👇
.@melaniecanva's journey to get @canva built wasn't easy.

She had:
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• No technical background
• 100+ investor rejections

What she did have was product market fit and an ambitious vision.

(photo h/t: @zachkitschke)
Melanie's original idea for @canva was to enable anyone in the world to design.

When she taught design @uwa in 2006, she found design software clunky and difficult to use.

"Students would take a whole semester just learning where the buttons were and how to design something."
Read 22 tweets
Aug 30, 2021
Ruben Harris started Career Karma, a platform that helps people break into the tech industry, in 2018.

Career Karma raised a $10 million Series A led by Garry Tan @Initialized in 2020.

This is a story of an outsider breaking into the Valley with sheer determination and hustle👇 Image
.@rubenharris’ story is all about overcoming long odds:

• Broke into investment banking with no connections.
• Linked with VCs like @balajis through Twitter.
• Landed a job in SF 3 weeks after booking a one-way ticket.
• Built an audience for CK before building a product. Image
Ruben went to college wanting to be a professional musician.

He’s been playing the cello for 30 years.

His cello teacher told him to understand business to help him become a professional musician.

To do that quickly, he chose to get into investment banking. Image
Read 16 tweets
Aug 11, 2021
I chatted with some of the top writers on Substack recently.

Here’s their advice on growing a newsletter:

[thread]
Rusty Foster (@fka_tabs), @TodayinTabs

Get people with a bigger audience to mention you.
Will Lawrence, Product Life

Remix content for social channels.
Read 8 tweets
May 24, 2021
Sam Udotong is one of the scrappiest founders in tech

In 2016, he moved to San Francisco with $100 in his pocket.

Today his startup Fireflies raised $14 million from top investors.

This is the story of his "overnight" success 👇👇👇
Sam's journey has been far from easy

• He moved to San Francisco with $100 in his pocket
• For years his daily diet consisted of a bottle of Soylent and three slices of pizza
• He and his co-founder pivoted the company *7 times*
Sam & co-founder @krish_ramineni started @firefliesai at an MIT hackathon

After graduation many of Sam's classmates took jobs at companies like Facebook and Google.

Sam bet on himself and decided to bootstrap his company.
Read 8 tweets

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