Revolutionizing Last-Mile Logistics: How Rich Pleeth’s Finmile Is Reshaping Delivery Through AI Innovation

Rich Pleeth, a former Google executive who spearheaded Chrome’s European launch and led market expansion at Bolt, is now revolutionizing the logistics industry with his AI-powered venture, Finmile. With a track record of successful startups and exits, Pleeth’s latest endeavor tackles one of e-commerce’s most pressing challenges: last-mile delivery optimization. As co-founder and CEO, he’s leveraging artificial intelligence to help retailers and carriers slash delivery costs by up to 42% through intelligent route optimization.

In an exclusive interview with Entrepreneur Loop, Pleeth shares his journey from tech giant executive to logistics innovator, revealing how his hands-on experience in delivery operations led to the creation of Finmile. The platform’s transformation from a practical solution to a pure SaaS model now scaling globally reflects his deep understanding of the industry’s pain points and his commitment to solving them through technology.

1. Please provide a brief introduction of yourself and your professional background.I’m Rich Pleeth, co-founder and CEO of Finmile, an AI-powered delivery software company focused on intelligent route optimization. Before starting Finmile, I launched Chrome across Europe at Google and led market expansion across Europe at Bolt. I’ve since built and exited startups, and now I’m focused on transforming logistics through software and AI.
2. Please tell us a bit more about your startup – what does it offer, what problem does it solve, and who is your target audience?Finmile is an AI-powered delivery software platform that helps retailers and carriers dramatically cut costs and emissions through smarter route optimization. Most logistics systems are outdated, wasteful, and built around static planning. We replace that with real-time, parcel-level decision making that adapts to changing conditions – from weather to customer availability and finds the most efficient route, every time. We built Finmile from the ground up after running our own delivery operations, so we know the pain firsthand. Our platform now serves national retailers, fast-growing e-commerce brands, and third-party logistics providers who want to increase delivery efficiency, reduce fuel use, and scale without ballooning operational overhead.
3. What inspired you to start your own business? What was the “aha” moment?
   I’ve always been obsessed with efficiency, not just finding the fastest way to do things, but spotting where things are breaking down and asking why no one’s fixed it yet. The “aha” moment came when we were running our own delivery operations and saw just how broken the last-mile really was. Drivers were being routed like it was 2005, static plans, no context, huge waste. I knew there had to be a smarter way. That’s when we decided to stop patching the system and start rebuilding it from the inside out with AI.
4. What were some of the biggest initial challenges you faced in getting your business off the ground? How did you overcome them?
   One of the biggest early challenges was getting people to believe. Logistics is a slow-to-change industry, built on relationships, legacy systems, and a deep resistance to risk. Convincing customers to trust a new platform, especially one driven by AI, wasn’t easy. It’s a compounding game: trust builds slowly, but once it starts, it accelerates. Fundraising was another uphill battle. Investors are cautious around logistics, especially when it’s not consumer-facing. We had to show not just the tech, but the traction, real savings, real clients, real operational depth. We overcame it by staying relentless, proving value parcel by parcel, and winning early believers who became our best advocates.
5. How did you identify a gap in the market or need that your business fulfills?We identified the gap by living it. While running our own delivery operations, we were constantly frustrated by the limitations of existing delivery software, clunky systems, static route planning, and zero adaptability. Route optimization tools on the market were either outdated or built by people who’d never actually worked in logistics. The turning point was realising that no one was offering parcel-level, real-time route optimization with true intelligence, software that could actually respond to on-the-ground conditions and make smart decisions at scale. That’s the gap Finmile fills. We built delivery software that’s not just about drawing routes, but about optimising every mile, every parcel, every shift, dynamically, and with purpose.
6. What has been your approach to funding your startup? Did you use your own savings, seek investors, crowdfund?
   From the outset, we knew we’d need the right partners to scale, so we started fundraising early. We were fortunate to secure MaC Venture Capital as our lead investor. They saw the opportunity, backed us when it was still early, and have supported us ever since. It’s made a huge difference having investors who believe in the long game and the impact of AI in logistics.
7. How did you go about building your team and attracting talent in the early days?
   It was really tough in the early days, especially without the perks of a big company behind us. We had to rely on vision, energy, and a lot of one-on-one conversations. We spoke to people directly, pulled them into the mission, and got them genuinely excited about what we were building. It wasn’t about hiring resumes, it was about finding people who cared about solving real problems and wanted to build something meaningful from the ground up. That’s how we attracted our earliest team, believers, not just employees.
8. What have been some of the toughest decisions you’ve had to make as a founder? Any stand out as pivotal?
   The toughest decisions, without question, have been letting people go. It’s the part of being a founder that no one prepares you for. These are people who believed in the vision, who gave their time and energy to build with you, and sometimes, as the business evolves, the structure has to change. You know it’s the right call for the company, but that doesn’t make it any less painful. Every time we’ve had to make that decision, it’s felt heavy. But in hindsight, those moments have often been pivotal, not because of who left, but because of how we handled it and what came next.
9. What have been your key strategies for growth and gaining traction/users?
   One of our key strategies has been good old-fashioned hustle, cold emails. I’ve become a professional cold emailer. It’s not glamorous, but it works. I reach out, follow up, and follow up again. Most of our early traction came from being relentless. We didn’t wait for users to find us. We went out, knocked on virtual doors, and made the case, one prospect at a time. Pair that with strong results from early pilots and word of mouth started to kick in. But the foundation was persistence. Relentless follow-up is underrated.
10. How do you stand out from the competition in your space? What sets your product/service apart?
    What sets us apart is that we’ve lived the pain, we ran our own delivery ops before building Finmile Ai. Most route optimization software is built in a vacuum, by teams who’ve never touched the last mile. We’ve been on the ground, in the vans, solving real problems in real time. Finmile isn’t just another delivery software. It’s parcel-level, real-time route optimization that adapts dynamically, not just at the start of the day, but throughout the shift. That means better efficiency, lower costs, and fewer missed deliveries. And unlike others, we’re a pure SaaS platform, no vehicles, no warehouses, just smart, scalable software that delivers results.
11. What have been some mistakes or failures you’ve made along the way as an entrepreneur? How did you recover and learn from them?I’ve made more mistakes than I can count, sometimes I’ve waited too long to make a decision, other times I’ve moved too fast. Both can hurt. The real learning has been about how we make decisions, not just which ones we make. One of the biggest shifts was recognising that I don’t have to carry it all myself. I rely heavily on my co-founder now. We talk things through, challenge each other, and make the call together. That’s been a massive unlock, moving from reactive decisions to shared, deliberate ones. Staying curious, staying humble, and learning from every hit. That’s how we move forward.
12. What do you know now that you wish you knew when you were first starting out?
    
    From the outside, logistics, looks simple, you order, something shows up. But under the hood, it’s chaos. And the kicker? It’s completely thankless. No one gives you a five-star review for a parcel arriving on time anymore, it’s just expected. Delivery has become a commodity. People only notice when it goes wrong. That makes the margin for error razor-thin and the pressure relentless. Now I know: in logistics, silence is the highest form of praise.
13. What are the most important skills someone needs to be a successful founder, in your opinion?In my view, the two most important skills are determination and relentless drive. You don’t need to be the smartest person in the room, but you do need to be the one who doesn’t quit. Building a company is a marathon of rejection, setbacks, and constant uncertainty and the only way through is to keep going when everyone else would stop. Skills can be learned, markets can shift, but if you don’t have that internal engine, that drive to keep pushing no matter what, you won’t last. Determination isn’t optional. It’s the job.
14. What does a typical day or week look like for you? How do you manage work-life balance?
    There’s really no such thing as a typical day, but here’s how it often looks: I’m up early, on emails by 7am. I make a coffee for my wife, kiss my two little girls goodbye, and tell them to learn as much as possible at nursery. Then it’s straight into team check-ins, investor calls, customer updates, and often a visit to a warehouse or logistics site, I still like seeing things on the ground. I do an ice bath everyday for 5 minutes, I don’t see a health benefit, just the fact that I can get into water that is 0.5 degrees centigrade (32 Farenheit) makes me feel stronger. I try to be fully present from 6pm to 8pm for dinner and bedtime with the girls, obviously I am not always successful. Then it’s back on for US calls in the evening. Work-life balance is more like a daily juggling act, but I’ve learned that being intentional, even for a couple of hours, can make all the difference.
15. What do you find most rewarding and most challenging about being an entrepreneur?The thing that really keeps me up at night is fundraising. I know our team relies on me, for their salaries, their families, in some cases even their visas. That weight is real, and it never leaves you. On the flip side, the most rewarding moments are the wins. When we land a big contract, get a yes from an investor, or finally crack a hard problem, those moments remind you why you’re doing this. You feel like you’re pushing the boulder up the mountain, and suddenly it moves. That’s everything.
16. What are some future goals or plans you have for your business in the next few years?Over the next few years, our focus is simple: scale smart and build a sustainable, profitable business. We want to grow our revenue and profit by 10x, but not by burning cash, by delivering real value through better, faster, more intelligent delivery software. We’re also pushing to 10x our tech. That means more automation, smarter routing, and deeper integrations so our platform becomes the invisible engine powering efficient deliveries across the globe. Profitability isn’t just a milestone, it’s the foundation for longevity, and we’re building for the long haul.
17. What advice would you give to aspiring entrepreneurs who want to start their own company?
    My advice? Just do it. Don’t wait for the perfect moment, it doesn’t exist. Start small, stay curious, ask for advice constantly, and surround yourself with people who challenge you. And most importantly, don’t let the no’s break your momentum. You’ll hear no a lot. From investors, customers, even people close to you. But if you believe in what you’re building, keep going. That persistence is what separates those who make it from those who don’t.

As Finmile continues to expand its global footprint, Pleeth’s vision for the future of logistics remains clear: build a sustainable, profitable business that transforms delivery efficiency through intelligent automation. With ambitious plans to 10x both revenue and technological capabilities, Finmile is poised to become the invisible engine powering smart deliveries worldwide. Through Pleeth’s leadership and unwavering determination, the company stands as a testament to how persistence and innovation can reshape an entire industry, one delivery at a time.