Startup culture loves a good myth: work hard enough, believe big enough, and success will follow. But the truth behind a fintech founder journey is rarely so clean. Building a company in this space means navigating shifting markets, personal sacrifices, and decisions that carry real emotional weight—often with no playbook.
Cokie Hasiotis, a serial entrepreneur with deep fintech roots, offers a raw and revealing look at what happens after the pitch decks are shelved, the products sunsetted, and the founder identity begins to fray. Her evolution—from a crypto startup to a content-tech pivot and finally, a soft landing through acquisition—is a masterclass in emotional resilience, hard-earned insight, and the high-stakes decisions that define a founder’s arc.
The Emotional Aftershock of Shutting Down
Cokie’s startup story isn’t just about market timing or investor strategy—it’s about identity. After shutting down her company Drippy, a pivot from her original crypto startup Twally, she described feeling “a little broken.” The confidence she once carried into rooms—sharp, bold, commanding—had faded. What replaced it was a sense of being lost.
But here’s where her story diverges from the cliché of founder burnout. Rather than wallow in ambiguity, she questioned the language around being lost. What if, she mused, we just gave it bad PR? What if “lost” is just another word for “in mystery,” a precursor to discovery?
That shift in perspective became one of the first signs of her rebuilding process.
When Timing Is Everything—and You’re on the Wrong Side of It
Twali was a crypto business with strong fundamentals, solid customer acquisition, and investor interest. But market crashes—Luna, FTX—shook the foundations just as the team was preparing for launch. Overnight, potential customers disappeared or turned into “the guy in the basement,” as she put it.
Faced with those realities, Cokie made the difficult decision to pivot. But that came with its own costs. She left behind what she still believes may have been her best idea. She also inherited a cap table optimized for crypto, not for a pivot into creator monetization tech. The financial strain of trying to raise a new round under old terms made it unsustainable.
In her words, “the math wasn’t mathing.”
The Danger of the “Beautiful Round”
The allure of early-stage capital—especially in a bull market—is intoxicating. But Cokie warns that those big, beautiful rounds can be traps. They seem like a blessing in the moment but can quietly set the stage for collapse later. High valuations restrict flexibility and can make future funding rounds nearly impossible without painful dilution.
For first-time founders especially, there’s often little education about how that plays out down the road. In retrospect, Cokie realizes that her fundraising terms played a major role in the company’s inability to pivot and grow sustainably.
Finding the Exit—and the Aftermath
Despite the challenges, Cokie pulled off something rare: a soft landing. Drippy was acquired by an InsureTech company interested in the startup’s payment flow. While it wasn’t a blockbuster financial outcome, it was a strategic and professional win.
Still, it didn’t feel like a win. Cokie kept the acquisition quiet for months. Imposter syndrome, emotional exhaustion, and lingering self-doubt clouded what should have been a celebratory moment. She even confessed to feeling like a fraud.
These feelings aren’t uncommon. The gap between what others see as success and how it feels internally can be massive. Her honesty around that experience is both refreshing and vital.
Reflecting on the Decision to Build in the First Place
One of the most striking parts of Cokie’s story is her openness about questioning whether she should have launched a company at all. Before founding Twali, she was running Lasagna, a fintech media property that generated strong revenue and influence. She had financial stability, control, and a lifestyle she enjoyed.
But public criticism—and an internal desire to prove herself—pushed her into startup life. She admits that ego, a longing for validation, and the pressure of being a visible woman in fintech all played roles in her decision to launch a venture-backed company.
In hindsight, she wonders if she was searching for something she didn’t truly want. And that’s a question more founders should ask themselves before diving in.
Emotional Labor and the Role of Support Systems
Running a startup demands every ounce of energy. When personal life collapses at the same time, the weight can be unbearable. For Cokie, the unraveling of a long-term relationship during the most intense months of building Drippy added layers of emotional strain.
She points to the importance of having real support—people who show up not just with encouragement but with action. She also acknowledges that if she had exited the relationship earlier, she might have preserved more of her own energy for the company.
It’s a reminder that emotional health isn’t separate from startup success. It’s central.
Advice for Aspiring Entrepreneurs
If you’re considering founding a startup, Cokie offers several points of advice:
- Know your superpower. Be honest about what you’re good at and double down on it. For her, it was people management and storytelling—skills that helped her raise capital and build momentum.
- Get out of your head. Emotional regulation is critical. Founders often operate from their brains and forget to check in with their bodies. Reconnecting with your intuition can make the difference between a reckless decision and a wise one.
- Be a master of filters. The startup world is full of noise. Investors, friends, advisors—everyone has advice. Your job is to filter it, take what’s useful, and discard the rest.
- Follow incentives. When working with partners, funders, or acquirers, always track their motivations. Understanding what drives the people around you is key to making smart, strategic decisions.
What Comes Next?
Right now, Cokie is still decompressing. She’s engaged, planning a wedding, and beginning a transitional program for high-achieving professionals reevaluating their paths. She’s also exploring creative and cash-generating ventures, rediscovering her love for writing and content.
Her next move might not be in tech. It might not involve raising venture capital. And that’s okay. The journey of an entrepreneur doesn’t have to end with an IPO or a unicorn. Sometimes, the real success lies in knowing when to stop, reflect, and choose differently the next time.
