Jess Mah on Building 10+ Companies and What It Really Cost Her

When Jessica Mah joined 10 other women CEOs for dinner in San Francisco, she expected another ordinary night of conversation with friends who understood the demands of leadership. Instead, the gathering turned into an intervention.

On the surface, she seemed to be living a founder’s dream. Her first company, inDinero — an accounting software and services business — had reached profitability and grown to more than 200 employees while she was CEO.

It was the kind of success most entrepreneurs only hope to achieve, but for Mah, it came at a cost. She felt like she was trapped by the business, and to her friends at the dinner table, it was obvious that her professional life was taking too much from her.

Wanting to help, they offered to help her find a new CEO to replace her. Mah agreed, vowing to continue her work, but never at the expense of her own well-being. Today, she’s determined to become the most authentic version of herself, not just as a founder, but as a human being. 

Finding the Thrill in Building 

Mah discovered her entrepreneurial side early on. When she was a middle schooler, she started her first business, putting together custom gaming computers for her classmates. In the process, she made six figures in revenue.

While at a summer camp for programming at 12 years old, she won a contest for assembling a computer in less than three minutes. Her love of technology took her to UC Berkeley, where she studied computer science.

By 2010, at only nineteen, she became among the youngest women accepted into Y Combinator. Then, three years later, she joined YPO as its youngest member at the time.

Since then, Mah has helped start and grow more than 10 companies, with multiple valued at over $100 million. She has raised tens of millions of dollars, led teams of hundreds, and earned recognition from Forbes 30 Under 30, Inc. Magazine, and Fast Company’s Most Creative People in Business.

Those milestones painted a picture of progress, but the reality was more complicated. When the COVID-19 pandemic hit, the weight of running a company intensified. Customers began closing their doors, layoffs became unavoidable, and in the midst of it all, her boyfriend passed away.

She credits her persistence during that time to a deep sense of responsibility. Customers who stayed open, employees who counted on her, and investors who believed in her all kept her in the fight.

“I knew we were going to create a world changing business, but we had to land the plane,” she said.

Finding Balance After Burnout

 After years of being consumed by her work, Mah was determined to change how she lived. She promised herself she would never again allow her work to take so much from her.

From then on, the real measure of success wouldn’t be bigger company valuations or business milestones, but whether she could maintain a fulfilling career and life at the same time.

“As a leader, I hope to leave a legacy around the companies we build, but as a person, I hope to leave a legacy as an example for others that you can and should have a great personal life alongside a great career,” she explained.

Now she divides her time between New York and San Francisco, surrounded by her favorite people and her puppy.

“It’s all about my friends, family, and boyfriend,” she shared. “They keep me grounded.”

Sharing the Mahway Method With the World

Out of Mah’s experience with inDinero came Mahway, a venture creation company designed to build businesses from the ground up. The goal is not to chase every idea, but to focus on a few and build them into strong companies.

“Being leaner and focusing on fewer projects is better,” Mahway explained. “I made the critical mistake of trying to go too wide and too broad too soon and since then dramatically narrowed in on only a few things where I have more conviction of where I can win.”

The company runs on systems Mah has developed throughout years of trial and error. She has even shared many of them publicly through the Billion-Dollar Startup Bundle on HubSpot. The bundle covers her methods for hiring talent, recruiting executives, scaling operations, and setting up companies for long-term growth.

Sharing these playbooks openly is rare in the startup world, but it’s proof of Mah’s belief that strong systems matter more than luck when it comes to being successful.

Making a Case for Encouragement

Aside from leading Mahway, Mah also serves on multiple startup boards, where she’s learned valuable lessons about what it looks like to be an effective leader.

“My leadership has changed where I am much more supportive and encouraging,” she said.

She describes her style as closer to a softball coach for third graders — someone who cheers people on, reminds them she believes in them, and offers feedback from a place of care instead of frustration.

As her perspective on leadership has changed, so has her idea of what it means to make an impact. Company performance remains important, but what truly excites her now is watching the people she works with grow into bigger, more meaningful roles that they genuinely enjoy.

The Secret Strengths Every Founder Needs

Having lived through the pressures of scaling companies, Mah has come to believe that self-reflection and the ability to self-critique are among the most underestimated qualities an entrepreneur can have.

Challenges and mistakes multiply as businesses expand, and the confidence that once carried a founder through the early stages can suddenly give way to doubt. She refers to these moments as “growth edges,” the points where the only way forward is to pause, look inward, and adapt.

The same concept applies to team building and company culture, where Mah finds value in being honest about challenges and working through them together. To her, admitting weaknesses or lessons learned is not a flaw but a way to bring people together to solve problems.

“You don’t need to shield team members,” she explained. “Don’t brush problems under the rug for the team, but inspire them to fix the problems.”

She also takes the time to ask her team about their long-term personal goals, not just their work ambitions, helping them connect their careers to the broader lives they want to create.

Inspired by the Unknown

Even with so much already behind her, Jessica Mah feels energized by what lies ahead. Artificial intelligence is the field that excites her most, with opportunities appearing at record pace.

“I am looking at business ideas every week,” she said. “I am excited about how there is so much new stuff coming out with AI on a weekly basis, that the coolest opportunities none of us have even begun to think about! Imagine that!”

Her curiosity extends across industries, from women’s health to insuretech, fintech, and the future of work itself. One of the aspects she finds most powerful about AI is its ability to help small teams move faster and operate more effectively than ever before.

In her next ventures, Mah wants to carry forward positive, uplifting energy and build with an AI-first mindset, where innovation is woven into every part of the company from the start.

She also hopes to influence how founders themselves are supported, especially when it comes to mental health. While entrepreneurship is often described as grueling, she sees it as a gift because it challenges people to grow into their full potential.

Human First, Founder Second

Despite everything she has accomplished, Jess Mah points to her personal life as her greatest success.

“I have loyal and committed friends and family who have my back through the ups and downs of life,” she reflected.

Mah is known for being transparent and bold, a trait she calls “extreme authenticity.” Her openness has not always worked in her favor, but she embraces it, believing that sharing both the highs and the lows builds a more genuine connection with her audience than any polished version ever could.

While many founders emphasize hustle over everything else, Mah brings a different kind of energy — one that mixes seriousness with play. She’s intent on rewriting the rules of venture in her own way, building companies while making room for creativity and fun along the way.

At the center of it all is a deep sense of humility, which she reminds young founders to practice even when things seem to be going well.

“If you don’t proactively humble yourself, the universe will do it for you in ways you won’t actively like,” she noted.