Sam DeBrule Profile picture
Aug 30, 2021 16 tweets 13 min read Read on X
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
Ruben’s university didn’t have an alumni network in investment banking.

So, Ruben found his own path:

1. Consumed @briand_mi’s blog + course
2. Sent 300 emails to @SEOScholarsNYC and @MLTOrg
3. Set up an SEO booth @Morehouse, where he met @BMO recruiters. ImageImage
Ruben joined BMO as an analyst in Summer 2011.

In 2013, he moved to Atlanta, where he met his @Career_Karma co-founders @ArturMeyster and @timurmeyster.

All three began to climb the investment banking hill.

The problem was that it was the wrong hill for them. Image
They saw their future in tech.

The Meyster brothers went the bootcamp route @appacademyio and @HackReactor.

Ruben took the biz dev route, but his path was less straightforward.

He got the attention of @balajis on Twitter, right around the time Balaji joined @a16z in 2013. Image
He continued networking with Balaji + more VCs on Twitter.

He arranged to meet @balajis, @geofflewis, and @km in May 2014 on an exploratory trip to SF.

During his May trip, he stayed at Agape, a living space founded by @JordanGrader and @justinrosenstein (co-founder of Asana). Image
But building relationships with VCs and engineers alone wasn't enough to break in.

Ruben took Stanford's CS 101 class since he didn't have a technical background.

He organized Atlanta's first Healthcare Hackathon and raised $40,000 with the leadership team. Image
In Sep 2014, Ruben went back to SF on a one-way ticket.

He continued to build relationships in the Valley and found mentors like @NaithanJones.

He leveraged one such friendly meeting to meet with Jane Yu, Head of Partnerships & Philanthropy at AltSchool. Image
.@janestweets didn’t have any open roles on her team, but she did have a contract role for a 6-week project.

3 weeks after Ruben moved to SF, he joined AltSchool for the project.

He eventually earned a full-time role on the growth strategy team. Image
The Meysters joined Ruben in SF in 2015.

They landed software engineering jobs @blippar and @FundingCircleUS.

All three had an atypical journey into tech, but they felt like the media didn’t cover stories like theirs.

They changed that by starting the @everest10x podcast. Image
The @everest10x podcast blew up.

Listeners reached out to the team to talk to guests and learn how they could break into tech.

Schools reached out to them for access to their audience.

Here’s how that led to the business model for @Career_Karma (h/t @garrytan):
This is where the idea for @Career_Karma was born.

Career Karma helps people break into tech by pairing them with bootcamps, mentors, and communities to help them get there.

@rubenharris & the Meysters launched CK in 2018. Image
In 2019, the three co-founders quit their jobs and joined @ycombinator.

In June 2020, they crossed 100,000 users.

The Series A raise led by @Initialized happened soon after. Image
Ruben’s story offers a playbook for people interested in getting into tech who are outside the Bay Area bubble.

And who knows?

With the hundreds of thousands of people he’s empowering to break into tech, his story might end up being a Silicon Valley classic too. Image
Trying to break into tech?

Want to get your own idea off the ground?

Join the Heyday community to get support from 1,000+ creators:

heyday.xyz/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:
• Zero Silicon Valley connections
• 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 23, 2021
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
Read 13 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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