How a High School Dropout Now Runs 10+ Companies Worth $955M

From starting a 6-figure server business in middle school, to high school dropout and building several successful businesses that have culiminated in a $952M net worth at just 33 - Jessica Mah’s entrepreneurial journey is nothing short of impressive.

Meet Jessica Mah

Jess Mah's origin story kicks off in Westchester, New York, where growing up with entrepreneurial Hong Kong immigrant parents set her on the path to business. Dinner conversations weren’t just about the day's events; they were impromptu strategy sessions for her mom’s business, sparking Jess's knack for solving real-world problems.

By the age of 10, Jess wasn't just playing around; she was teaching herself to code. By 11, she had already launched her first venture: a server space business on eBay. Her edge? Stellar customer service that kept her up to the early hours of the morning.

Before she even hit her teens, Jess was running a business that raked in six figures and employed four part-time workers. She was out-earning her teachers and learning the art of hustle. Juggling a burgeoning business and school proved too much. At 14, cash flow issues and the impact on her schooling forced her to shut it down, selling off the assets for next to nothing.

Teenage Hustle

Enter her teenage years. At 16, Jess was armed with raw ambition and a fearless attitude, she cold emailed the likes of Steve Huffman of Reddit and Emmett Shear of Justin.tv/Twitch. With self-deprecating charm, she called herself an “idiot” 16-year-old who just wanted to shadow them. Her audacity paid off—she ended up driving Emmett around San Francisco, even tagging along to a poker game. Even Marc Benioff of Salesforce couldn't ignore her hustle and shot her a reply.

These encounters weren't just meet-and-greets; they sparked a realization in Jess that waiting was overrated. The big lesson? The right mindset trumps a ready-made career path. This revelation came just as she was grappling with subpar grades and a gnawing fear of a lackluster future. So, she made a bold move: dropping out of high school at 16 to dive into college early at Bard College at Simon’s Rock, where exceptionally young students get a jumpstart on higher education.

At Simon’s Rock, Jess didn’t just accelerate her education; she earned her Associate’s degree in record time and made her way to UC Berkeley to tackle a degree in computer science.

She didn’t just study either, she led the computer science undergrad club as president, a role she used to connect with industry influencers. Among the speakers she brought in was a notably sharp young guy—Sam Altman. This connection would one day pay major dividends.

It was at Berkeley that she crossed paths with Andy Su. The pair didn’t waste time; they threw together InternshipIN, a platform linking students with internships. The startup wasn’t a blockbuster hit, but for a mere $500 launch cost, the lessons were priceless. Jess and Andy were cutting their teeth in the real business world, gearing up for bigger plays.

inDinero

The real turning point came during a lunch at Gypsy’s, an Italian restaurant near Berkeley, where Jess and Andy conceived their next idea.

In 2010, they started inDinero - a business to show owners their financials online in real-time.

Sam Altman (yep, that guy) dropped a tip for Jess: "Hit up Y Combinator." They did, nailed the pitch, and bam!—inDinero took off. With YC’s support and guidance, Jess and Andy fine-tuned the startup into a money magnet, pulling in a cool $1.2 million from big guns like YouTube's Jawed Karim and the sharpshooters at 500 Startups.

Fast forward to the end of 2010, and inDinero was on fire—seven employees, 6,000 customers, and managing a whopping $2 billion in transactions. Everyone thought inDinero was the next big thing.

Then, the tide turned—hard. By 2011, cash was bleeding. Customers were bailing, and inDinero’s cash reserves were drying up faster than a puddle in the Sahara. Jess faced the music: it was time for some hardcore decisions. She had to lay off almost everyone just to keep the ship from sinking. Brutal, yes, but Jess was playing the long game to save inDinero.

The Great Pivot

That crunch time was a game-changer for Jess. When one client dangled the carrot of thousands for a comprehensive service, the light bulb went off. Jess swerved inDinero from just software to a full-service accounting firm, throwing in the much-needed human touch to help out small businesses with consulting services. This pivot wasn’t just smart—it was a lifesaver, stabilizing the business and nudging it towards profitability by 2014.

The momentum helped them bag an additional $7 million in funding in 2015.

But Jess wasn’t splurging on herself; she kept her salary lean to keep the finances tight—$30k a year for the first few years, then bumping up to $80k around the time they started to show profits, and later, $120k.

During all of this rollercoaster, Jess had her eyes on the skies—literally. Every spare dollar went into flying lessons, not just as a hobby but as a tool she would later use to expand her network and business.

Pivot #2

When COVID-19 hit, Jess transformed into a business lifeline. She hustled with her team at inDinero to help clients navigate the storm—securing PPP loans, slicing costs, and pivoting business models. Jess felt like the business world's frontline worker, crucial in steering others through the crisis. However, inDinero was bleeding from financial overreach, high churn, and dismal monthly reports, dragging Jess down.

In a twist of fate, while partying in Las Vegas in July 2020 with a DJ friend hit hard by the pandemic, Jess sparked up a legal tech venture aimed at democratizing legal victories. They planned to split court winnings among clients, lawyers, and themselves, bootstrapping the project with her savings and some funds from inDinero. Stealth mode didn’t stop them; they launched with substantial litigation funds and began turning a profit in the millions. It still operates profitably and quietly in the background.

It felt like Jess was starting to rediscover her entrepreneurial spark again, until tradegy struck that changed the trajectory of her life forever.

Jess’s ex-marine boyfriend tragically took his own life during her business trip, plunging her into deep depression. For six months, Jess disconnected from the world, letting her team keep inDinero afloat while her friend ran the legal business. During this dark time, she contemplated her fears and failures, working on herself and figuring out where she wanted to spend her team moving forward.

It led to the radical decision: she didn't want to be CEO anymore.

Emerging from her sabbatical with a new perspective, Jess dove deep into the entrepreneurial scene. She shifted her focus to funding bold, innovative startups, particularly in biotech, where she could support new CEOs rather than being one herself.

Pivot #3 - Welcome to Mahway

Think of Mahway as her “manifestation studio” where her ideas can morph into reality.

Here's the lowdown: Mahway isn't just an investment firm; it's Jess's personal startup machine. With a team of 12, they're the support crew behind the brains, helping CEOs whip up prototypes, craft marketing strategies, and drum up fundraising. Jess is in the trenches with the CEOs, steering the ship on strategy and vision.

Mahway’s got a roster of 10 companies, spanning from the tried and true inDinero that is generating tens of millions in top line, to fresh ventures like the ambitious Astonishing Labs. There’s also AlphaLit shaking up fintech, Precognito redefining tenant predictions with AI, and StemAI, not to mention a few more under wraps.

Astonishing Labs is Mahway’s dive into the biotech ocean, despite her own self-professed C- in Biology. Her secret? Hiring a tutor, snagging top-tier science talent, and teaming up with seasoned biotech entrepreneurs.

Through all this, Jess has reportedly skyrocketed to a net worth of $952M, not just mastering entrepreneurship but also becoming a wizard of finance and taxes.

Here’s a pro tip straight from Jess:

Also she shared her self development arsenal on a recent MFM Podcast:

1. Dual Coaching: Jess syncs with two high-caliber coaches monthly to keep her level on and on point.

2. CEO Support Group: Monthly meet-ups, think AA for CEOs.

3. Young Presidents’ Organization (YPO): Networking with fellow young leaders.

4. Health Optimization: Collaborates with five doctors to tailor her nutrition, nootropics, and longevity plans, dropping about $20k annually for peak performance.

Looking ahead, Jess doesn't have a fixed target but envisions launching at least 20 startups over the next decade.

Her advice for aspiring entrepreneurs? Stay true to yourself and never stop asking questions.

Got an entrepreneur you want us deep dive into for an upcoming issue? Reply and let us know.

Check your inboxes next week for our next instalment of The Entrepreneur Chronicles.