Most people at 25 are just getting their feet under them at their first job out of college. At 25, Chase Spenst was getting flown out to Chicago and picked up in limousines so hospital managers could wine and dine him.
Chase had become a financial “fixer” for the hospital industry. He was part of the teams hired to help them engineer financial turnarounds. He was on a hot streak while most of his classmates were jobless from the 2008 recession. It seemed like nothing could stop his good fortune.
Then without warning, his boss, the hospital CEO retired and his new boss promptly fired him.
This experience, among others, pushed Chase to create his startup, Good Operator, a business helping bootstrapped startup founders manage their books. To Chase, financial freedom doesn’t come from a number in the bank, but from the ability to bootstrap cash flow on your own, unbeholden to any boss or investor. In short, owning your own business is the best way to control your own fortunes.
Today, Chase’s agency makes high six-figure annual revenues and serves as the back office for dozens of bootstrapped startups. But Chase’s entrepreneurial journey wasn’t as simple as walking out that hospital door and making a profitable agency.
After leaving hospitals, Chase joined the ground floor of a healthcare startup and rode it to IPO but struggled to fit in at the company. He built a bicycle shop and cafe that closed after two years. He also traveled throughout Asia as an operator for private equity but left when the opportunities he was promised for his service never materialized.
Buffeted by the winds of fortune for almost a decade, Chase had a realization: if he ever wanted the control he desired in life, he had to create for himself the cash-flowing, stable business that he dreamed of.
Read on to learn about Chase’s meteoric rises and falls and what they taught him about being an entrepreneur.
If You Want it, You Need to Work For it
As a child, Chase recalls he was never simply handed money. His parents made it clear that if he wanted things, he would need to work for them.
“By the time I was six, my father would say, ‘If you want that baseball glove then my shoes need shining.’ Once I could push the lawnmower I was doing that.”
Chase always wanted to run a business, but to him, there were only two ways to be your own boss. “I felt I could run a big interesting company as CFO or CEO or run a cute small business like a coffee shop,” he says.
Ironically, he would go on to do both. But that’s getting ahead of the story.
Chase took a shine to finance as an undergrad in business school. He wanted to work on deals for investment banks and climb the corporate ladder. Unfortunately, while Chase had all the skills to be a top accountant, he’d graduated in 2006, the year leading up to the American financial crisis. While few spoke of it, most financial firms secretly knew it was about to happen and were hiring accordingly.
“People were not calling fire yet, but they were pulling back on unfilled positions,” says Chase. “The job would get removed while I was interviewing.”
However, Chase had done a fortunate internship at a hospital company while he was in college. They loved his work and regularly called him to see if he wanted to continue as a full-time employee. Out of options in the financial world, Chase decided to work in the hospital’s back office while he got his master’s degree.
He ended up being in the perfect industry at the perfect time.
The Hospital Doctor
Working in healthcare when most other young analysts wanted to work on Wall Street made Chase stand out like neon paint on tarmac. He was young, energetic, and smart in an industry where most of his colleagues were in their 40s and coasting.
“If you were young and ambitious in healthcare at that time you were belle of the ball,” he says.
Chase would go on to be promoted every few months for the first couple years of his career. Barely 25, he found himself reporting directly to the CEO of one hospital group and tasked with business development, strategy, and Decision Support for a $100 million company.
However, not everyone was impressed with Chase and his ascent. Following the CEO’s retirement, he found himself temporarily reporting to a VP who fired him after their second meeting.
But the experience taught Chase that he was onto something in the healthcare industry, something that hospitals were too old and entrenched to address. He joined a startup called Evolent Health working on exactly the type of solution he’d wanted to implement at his previous employer.
“I realized these startups are doing things the way they should be,” he says. “These startups were fun, wild, and fast-paced; there was always something exciting.”
Chase joined as one of the first 100 employees at Evolent in 2012 and he loved every minute of the scrappy startup experience. However, by the time he left in 2015, it had over 1,000 employees and an IPO under its belt. It had become a large ponderous organization much like the hospitals he’d worked at.
Feeling for the second time that his company had changed dramatically, in 2015 Chase decided that, going forward, he would never be anyone’s employee again.
Don’t Open a Cafe Right After Your Honeymoon
Chase experienced two more punishing, yet instructive, failures before starting Good Operator. His first was running that cute cafe in Los Angeles he’d thought about as a student.
It all began while honeymooning with his newlywedded wife in South Africa. Chase and his wife fell in love with the idea of owning a cafe in Los Angeles after frequently a few on their trip. Theirs would be a bicycle cafe in a large warehouse called The Wheelhouse.
“I do not recommend opening a cafe right after your honeymoon,” says Chase.
The Wheelhouse lasted for two years (2015-2017) before money problems caused the couple to close the doors. While Chase calls it a heartbreaking failure, it taught him a lot about running a business. Specifically, how to manage its cash flow.
“Early on, a contractor took off with 120,000 dollars,” he says. “That took all of our working capital in an industry where normally it takes two years to be profitable. Cash flow became our number one focus and we survived for two years purely because we learned how to stretch every dollar.”
After the café, Chase took on consulting work for a private equity firm managing special projects worldwide. Through 2019, he helped them launch and manage their businesses in Asia.
“One day, I was in Shanghai trying to figure out where the cool neighborhoods were for a new concept,” Chase recalls. “The next, I was in Japan running a ski resort and bar.”
While exciting, the work was still too dependent on others. The deals were constantly changing, the scope was always creeping. He knew he needed a more stable and scalable business model. Fortunately, he had a couple of skills that never went out of style: Bookkeeping and Excel.
Where Else Do Clients Stick With a Contractor They Hate?
Chase was pretty much out of money at this point, but he still didn’t want to throw in the towel and go back to corporate life.
Instead, like many finance people trying to make ends meet, Chase set up a small consulting business helping startup founders (mostly of VC-backed startups) with accounting. While he initially resisted including the most common accounting service, bookkeeping, he eventually added it in when he realized it was just too high-demand.
“I never wanted to be a bookkeeper,” he admits. “But I kept hearing the same complaints—people were unhappy with their accountants, it took weeks to get replies, and they just wanted someone responsive.”
Realizing the opportunity in bookkeeping, Chase leaned into customer service, treating his firm like a hospitality business rather than a traditional accounting practice. His team became known for responding to emails within hours instead of weeks and he pushed them to go the extra mile for clients.
“At one point, a client joked that if we weren’t busy, we could help him paint his house. The next morning, my team had researched and sent him a list of top-rated painters in his area,” Chase says. “That’s the level of service we bring.”
The real turning point came when Chase decided to focus exclusively on bootstrapped businesses. Previously, much of his work came from venture-backed startups raising capital. However, he became disillusioned with the venture capital model and started speaking openly about it on social media.
“It was terrifying because I’d built the business on doing cap tables for VC-backed companies,” he says. “Then I publicly went on social media and began trashing the venture capital ecosystem. But I believed in helping founders build profitable, self-sustaining companies, not just chase fundraising rounds.”
After a few heart-wrenching months, Good Operator suddenly started getting clicks. Founders who shared Chase’s philosophy flocked to his firm. Today, he’s created a team specialized in helping bootstrapped businesses optimize their cash flow, maximize profitability, and scale sustainably—without outside investment.
Chase’s Advice for Bootstrapped Founders
Looking back, Chase sees every setback as a stepping stone to his success. His advice to other bootstrapped founders is to get started faster than you think.
“Don’t overcomplicate things,” he says. “Don’t build systems before you have a single paying customer. Don’t create a Notion, don’t automate, and don’t do AI for a very long time. Do one version completely manually and do it slightly less badly the next time. Just get in, do the work, and iterate as you go.”
He also thinks the hard experiences were all necessary for him to reach where he is today.
“I needed these things to all fall apart to see where my limits were,” he says. “I look back on that guy getting driven around in the limo and I think he was soft. I’m ten times the operator I used to be.”
Now, as Chase’s firm continues to grow, he remains committed to the bootstrapped mindset: focusing on cash flow, prioritizing service, and helping founders succeed on their own terms.
“I don’t want to run the biggest accounting firm,” he says. “I want to build the best one for people like me.”
