Jim Kolchin started iWallet because he knew the problem from the inside. Before he was building fintech software for contractors, he was a contractor himself. He started his first business in 2003, spent 15 years working in the field, and grew that business from nothing into an eight-figure company. That is where he saw the pain around checks, credit cards, receivables, and all the little financial tasks that slow down home service businesses. Kolchin describes iWallet as a new way for contractors to take payments, saving time and money on check processing and credit card processing. But the company is now growing into something bigger: a financial operating system for the home service industry, serving contractors, distributors, and manufacturers. That matters because home service businesses are still full of old payment workflows. Contractors mail checks, wait on lockboxes, process card payments, chase invoices, and deal with back-office systems that were not really built for the way field service companies operate. iWallet is trying to pull those pieces together in a way that fits how contractors actually work. Kolchin’s path into software was not straight. He came to the United States in 2002 and started with odd jobs: selling ice cream, washing cars, sweeping the boardwalk in New Jersey, and saving enough money to move to California. A year later, he started his first business. He liked contracting, but he eventually saw the limits. A contractor can build a good business, but labour does not scale like software. He had already learned that lesson through another startup, a hardware company that built an automated knife-sharpening machine and was later sold. Before that, he had tried a mailbox sensor, manufactured 100 units, launched a Kickstarter, and discovered that having a clever invention was not the same thing as having a market.That failure taught him one of the oldest startup lessons, but one that still has to be learned the hard way: make something people want. Kolchin said he originally thought like an inventor. If you had a patent, he believed, people would come looking for it. That was not how it worked. Over time, he learned that the customer matters more than the idea, and that the only way to know what people want is to talk to them directly. Surveys and gated forms are not enough. Real conversations are what count. For iWallet, that has meant trade shows. Kolchin said trade shows are one of the best places to meet contractors, talk to customers, test messaging, and understand whether the product is solving a real problem. But it only works if you work the room. You cannot sit behind the table and wait. You have to get up, talk to people, explain what you do, and push through the awkward first half hour until the conversations start to flow. That kind of direct selling is also how you find product-market fit. Kolchin pointed to the idea of the “unaffiliated dollar,” a dollar paid by someone who did not know you six months earlier and bought the product because you convinced them it solved a problem. For him, that was the real test. One unaffiliated customer can become another, and that is where momentum begins. After years of trying different ideas, Kolchin said iWallet found product-market fit about three years ago, became profitable, and began growing quickly. The company is now expanding beyond payments. Kolchin said iWallet is working on Repair AI, which he described as something like Harvey for legal or OpenEvidence for medical, but built for the home service space. The company has filed several patents around the idea and sees it as a major opportunity. At the same time, iWallet is building out more traditional financial products. Accounts receivable is core today, but the roadmap includes accounts payable, checking accounts, credit, and extended warranties. The goal is to give contractors a financial layer that understands their business instead of forcing them to stitch together tools built for everyone else. There is a simple founder lesson in Kolchin’s story. The first idea may not work. The second may work better. The third may reveal the market. What matters is learning fast enough to stop building only what interests you and start building what people will pay for. That is what iWallet is doing now. It began with contractor payments. It is becoming a larger financial system for an industry that still runs on too much paper, too many checks, and too many disconnected workflows. Kolchin built iWallet because he lived the problem. That is often where the best companies start. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe
