Adam Mendler, creator and host of 30 Minute Mentors, spoke with Gain CEO and founder, Reid Zeising, about failure, recovery, leadership, AI, and what it takes to build a strong company. Here are six pieces of advice.
1. Learn from failure and plan harder for downside
Zeising said his path was shaped by “a long series of failures, lessons, resets, and a few opportunities.” Early in his career, he learned being too focused on himself made him effective in some ways but also isolated. Later, after acquiring Backyard Burgers, the Great Recession hit, the business suffered far beyond what he had modeled, and he was left facing roughly $22 million in contingent liabilities. He described that chapter as the most painful of his life, but also the most important. It forced him to become more honest, make amends, and rethink how he lived and led. He said one of the biggest lessons from that period was to spend more time asking what happens if things do not go right.
2. Solve a real customer problem before chasing certainty
One of Zeising’s clearest points was that entrepreneurs rarely know for sure that an idea will work. “You test, you respond, you adjust,” he said, and customers ultimately tell you whether something has value. In his case, the business began when two trial lawyers he trusted asked him to enter the plaintiff funding business. From there, the model expanded logically. His advice? Go after a big market, solve a real problem, and look at every question from the customer’s perspective. If the friction you are removing is not obvious, the idea is probably not ready.
3. Use technology to remove bottlenecks, not to chase hype
Zeising said one of the company’s biggest growth levers has been adapting quickly to technology. He pointed to years of quantitative work around case values and said that, today, many people would call that AI. For him, the label matters less than the result: using better tools to make better decisions, move faster, and eliminate bottlenecks. He said that mindset now extends across marketing, operations, and service, where AI agents and related tools help increase leverage and improve productivity.
4. Get hands-on with AI instead of waiting from the sidelines
Zeising’s message to leaders is to engage now. He warned too many leaders are still waiting for the perfect product, the ideal vendor, or someone else on the team to figure it out. His view is that leaders need firsthand experience. “Roll up your sleeves. Build something. Use the tools. Make mistakes. Watch it fail. Improve it.” He also drew a sharp distinction between workers who adapt and those who refuse to evolve, saying he is not seeing people lose jobs to AI itself so much as to their unwillingness to use it.
5. Warm up leads with marketing, then let sales close through trust
Zeising said technology can automate much of the early sales process, from lead generation to outreach sequencing and campaign testing. But he was clear that “you still cannot automate the last mile.” When it is time to close important business, trust still matters. Buyers want to know who they are working with. His advice: let marketing create leverage, warm up leads as much as possible, and let sales convert trust.
6. Hire strong people, set clear standards, and lead by example
Zeising said the hardest balance in leadership is empowering people without lowering standards. He believes in giving capable people room to act, experiment, and sometimes fail, but only if they are the right people for the role. He emphasized manageable teams, clear expectations, measurable accountability, and hiring people who are better than you in their areas of responsibility. The best advice he said he ever received was to “be of service,” a lesson that reshaped how he thinks about success, contribution, and leadership.
This interview was summarized from a conversation with Gain Servicing and Adam Mendler, creator and host of 30 Minute Mentors.