Gain CEO Reid Zeising Shares Entrepreneurial Journey and Advice

Zeising discusses overcoming failures, leveraging AI, and building high-performing teams

Apr. 6, 2026 at 3:34am

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In a recent interview, Reid Zeising, founder and CEO of Gain, opened up about his entrepreneurial journey, sharing how past failures and challenges ultimately led to the creation of his successful fintech startup. Zeising discussed the importance of adapting quickly to new technologies, building strong teams, and maintaining a service-oriented mindset as keys to driving business growth.

Why it matters

Zeising's story provides valuable insights for aspiring entrepreneurs and business leaders looking to navigate the ups and downs of building a company. His willingness to be transparent about his own missteps and learnings can inspire others to approach challenges with resilience and an openness to growth.

The details

Zeising's path to founding Gain was marked by a series of setbacks, including a failed hedge fund and an overleveraged acquisition during the Great Recession. These experiences taught him the importance of planning for downside scenarios and getting brutally honest with himself, ultimately leading him to Alcoholics Anonymous and a new beginning. When two trial lawyers approached Zeising to help with the plaintiff funding business, he saw an opportunity to apply his financial expertise to a new market need, eventually developing systems to manage medical receivables that solved a broader problem.

  • Zeising started in investment banking, which he says taught him valuable lessons about capital markets and business success and failure.
  • In 2009, Zeising walked into Alcoholics Anonymous, a pivotal moment that changed how he leads and lives.
  • Two investors asked Zeising to build a company to serve a new market need, which became the genesis of Gain.

The players

Reid Zeising

Founder and CEO of Gain, a fintech startup providing financial services to the legal industry.

Adam Mendler

Entrepreneur and author who interviewed Zeising for his blog.

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What they’re saying

“Entrepreneurs often convince themselves their idea is a good one before the market ever weighs in. But that's not reliable. In our case, we did not assume anything. We tested, responded, adjusted, and let customers validate what we were building.”

— Reid Zeising, Founder and CEO, Gain

“The biggest technology trend leaders need to understand is not a specific tool. It is the urgency of direct engagement. Too many leaders are still deflecting. They are hoping the perfect product will arrive, or waiting for a vendor to customize something for their company, or assuming someone will handle it behind the scenes.”

— Reid Zeising, Founder and CEO, Gain

What’s next

Zeising plans to continue expanding Gain's use of AI and other technologies to drive greater productivity and efficiency across the company's operations and service delivery.

The takeaway

Zeising's entrepreneurial journey underscores the importance of resilience, adaptability, and a customer-centric mindset in building a successful business. His willingness to learn from failures and embrace new technologies provides a roadmap for other leaders looking to take their companies to the next level.